Ianslistings.com Search Results

New construction, Elevated 3BD/3.5BA with heated pool and gated off-street parking on coveted Olivia Street. The Twins on Olivia is a Key West landmark reborn. The original structures, known locally as 'Olivia's Twins' and documented on the 1892 Sanborn maps, were condemned by the city and demolished. In their place, Kanga Construction has built an all-new 2,421 sq ft home on a 2,773 sq ft lot, designed with extensive guidance from Key West's HARC to honor the original twins in form and spirit. That history lives on in two separate staircases, a nod to the original pair of homes that also gives guests or family their own side of the house. All three bedrooms have ensuite baths and built-in closets, and dual-zone A/C with two whole-house dehumidifiers keeps every room comfortable year-round. French oak floors run throughout bright, open living spaces. The kitchen pairs Viking appliances, including a gas range and ice maker, with custom Hansel & Bringle cabinetry and quartz countertops. Impact-rated windows and doors, among them a custom mahogany front door with matching mahogany entry and lattice details, combine island craftsmanship with hurricane protection. Outside, ipe decking surrounds a heated pool with waterfall, set within private tropical landscaping. Off-street parking sits behind an electric gate. The home is offered fully turnkey, with a curated furniture package by local designer David Smith valued at over $150,000 plus plantation shutters throughout, all steps from Old Town's best restaurants, galleries and landmarks. Historic Key West character, built new.

3 Beds ⋅ 4 Baths ⋅ 621485 MLS

New construction, Elevated 3BD/3.5BA with heated pool and gated off-street parking on coveted Olivia Street. The Twins on Olivia is a Key West landmark reborn. The original structures, known locally as 'Olivia's Twins' and documented on the 1892 Sanborn maps, were condemned by the city and demolished. In their place, Kanga Construction has built an all-new 2,421 sq ft home on a 2,773 sq ft lot, designed with extensive guidance from Key West's HARC to honor the original twins in form and spirit. That history lives on in two separate staircases, a nod to the original pair of homes that also gives guests or family their own side of the house. All three bedrooms have ensuite baths and built-in closets, and dual-zone A/C with two whole-house dehumidifiers keeps every room comfortable year-round. French oak floors run throughout bright, open living spaces. The kitchen pairs Viking appliances, including a gas range and ice maker, with custom Hansel & Bringle cabinetry and quartz countertops. Impact-rated windows and doors, among them a custom mahogany front door with matching mahogany entry and lattice details, combine island craftsmanship with hurricane protection. Outside, ipe decking surrounds a heated pool with waterfall, set within private tropical landscaping. Off-street parking sits behind an electric gate. The home is offered fully turnkey, with a curated furniture package by local designer David Smith valued at over $150,000 plus plantation shutters throughout, all steps from Old Town's best restaurants, galleries and landmarks. Historic Key West character, built new.

1010 Olivia St, Key West

1901 S Roosevelt Blvd Unit 208E, Key West

$1,349,000

Direct ocean views await at this rarely available 3-bedroom, 2-bath condominium in Key West's gated La Brisa community, directly across from Smathers Beach. Whether you're seeking a full-time residence or a seasonal escape, Unit 208E offers bright living spaces, an updated kitchen, and resort-style amenities. The open floor plan connects the kitchen, dining, and living areas, creating an inviting space for everyday living and entertaining. Sliding glass doors open to a private balcony overlooking the ocean--an ideal setting for morning coffee and enjoying the sea breeze. The updated kitchen features modern cabinetry and ample counter space. The primary suite features ocean views through a large picture window, direct balcony access, generous closet space, and an en-suite bath. Two additional bedrooms offer comfortable accommodations for family and guests or space for a home office. La Brisa's amenities include a heated pool, hot tub, tennis and pickleball court, clubhouse, BBQ area, EV charging stations, and gated entry. Enjoy convenient access to the beach, bike paths, airport, and Key West's dining and attractions. Seller is a family member of the listing agent.

3 Beds ⋅ 2 Baths ⋅ 621474 MLS

Direct ocean views await at this rarely available 3-bedroom, 2-bath condominium in Key West's gated La Brisa community, directly across from Smathers Beach. Whether you're seeking a full-time residence or a seasonal escape, Unit 208E offers bright living spaces, an updated kitchen, and resort-style amenities. The open floor plan connects the kitchen, dining, and living areas, creating an inviting space for everyday living and entertaining. Sliding glass doors open to a private balcony overlooking the ocean--an ideal setting for morning coffee and enjoying the sea breeze. The updated kitchen features modern cabinetry and ample counter space. The primary suite features ocean views through a large picture window, direct balcony access, generous closet space, and an en-suite bath. Two additional bedrooms offer comfortable accommodations for family and guests or space for a home office. La Brisa's amenities include a heated pool, hot tub, tennis and pickleball court, clubhouse, BBQ area, EV charging stations, and gated entry. Enjoy convenient access to the beach, bike paths, airport, and Key West's dining and attractions. Seller is a family member of the listing agent.

1901 S Roosevelt Blvd Unit 208E, Key West

$4,300,000

There is a certain rhythm to life in Key West. Mornings begin outside, friends have a way of staying longer than planned, and some of the best evenings never make it past the backyard. 1614 Washington Street was designed for exactly that kind of life. Natural light, high ceilings, and an easy connection to the outdoors give the home an immediate sense of openness. The main living spaces flow naturally toward the pool and tropical garden, creating a setting that works just as well for a quiet morning at home as it does for dinner with friends that stretches late into the evening. The heated and chilled pool features two distinct levels--a shallow splash deck and a deeper swimming area--connected by cascading water features and surrounded by mature tropical landscaping that feels remarkably private. The floor plan understands that guests are part of island life, but privacy still matters. The first-floor primary suite creates a comfortable retreat for the owners, while upstairs, three en-suite bedrooms surround their own den and lounge. Family and friends can settle in, unpack, and have a space of their own rather than simply occupying yours. Behind that relaxed lifestyle is a house designed to make living here easier. Award-winning local architect Matthew Stratton brought together solid masonry construction, impact-rated windows and doors, solar power with Tesla battery storage, an EV charger, custom cabinetry, quartz surfaces, and thoughtful systems chosen for the realities of coastal living. The technology is there when you need it and nearly invisible when you don't. Morning walks, bike rides, the beach, neighborhood restaurants, galleries, and everything that makes Key West unlike anywhere else are simply part of the day. 1614 Washington invites you to open the doors, gather the people you love, jump in the pool, stay for dinner, and make yourself at home. Because ultimately, the best luxury isn't about having more. It's having a home that lets you live well.

4 Beds ⋅ 5 Baths ⋅ 621463 MLS

There is a certain rhythm to life in Key West. Mornings begin outside, friends have a way of staying longer than planned, and some of the best evenings never make it past the backyard. 1614 Washington Street was designed for exactly that kind of life. Natural light, high ceilings, and an easy connection to the outdoors give the home an immediate sense of openness. The main living spaces flow naturally toward the pool and tropical garden, creating a setting that works just as well for a quiet morning at home as it does for dinner with friends that stretches late into the evening. The heated and chilled pool features two distinct levels--a shallow splash deck and a deeper swimming area--connected by cascading water features and surrounded by mature tropical landscaping that feels remarkably private. The floor plan understands that guests are part of island life, but privacy still matters. The first-floor primary suite creates a comfortable retreat for the owners, while upstairs, three en-suite bedrooms surround their own den and lounge. Family and friends can settle in, unpack, and have a space of their own rather than simply occupying yours. Behind that relaxed lifestyle is a house designed to make living here easier. Award-winning local architect Matthew Stratton brought together solid masonry construction, impact-rated windows and doors, solar power with Tesla battery storage, an EV charger, custom cabinetry, quartz surfaces, and thoughtful systems chosen for the realities of coastal living. The technology is there when you need it and nearly invisible when you don't. Morning walks, bike rides, the beach, neighborhood restaurants, galleries, and everything that makes Key West unlike anywhere else are simply part of the day. 1614 Washington invites you to open the doors, gather the people you love, jump in the pool, stay for dinner, and make yourself at home. Because ultimately, the best luxury isn't about having more. It's having a home that lets you live well.

1614 Washington St, Key West

$2,195,000

Completed in 2025, this brand-new, elevated two-story home rises above the surrounding homes and is built above flood level. Excellent location close to the beach. Category 5 hurricane-rated construction, impact windows and doors, and Hardie board siding combine coastal style with storm protection. The home offers 3 bedrooms and 3 bathrooms, plus an office currently set up with bunk beds as a fourth sleeping space. Separate laundry room. The backyard is a gorgeous tropical retreat. A large heated pool and spa are surrounded by a gorgeous stone deck, lush landscaping and dramatic evening lighting. A huge poolside Tiki hut creates a spectacular setting for shaded dining, lounging and entertaining, while a putting green adds to the fun. Generous gathering areas and a completely fenced yard make this outdoor oasis perfect for sunny afternoons and unforgettable evenings beneath the palms. Inside, bright, open living and dining spaces flow into a beautiful kitchen with white cabinetry, stainless steel appliances, a blue tile backsplash and a generous island with seating. Balconies extend the living space outdoors. Beneath the home, a large covered area offers room to watch sports, relax and entertain, or serve as a carport. A permitted downstairs enclosure provides valuable storage and pool cabana. New construction, an elevated setting and an exceptional backyard come together in one remarkable property. Don't miss your opportunity to make this tropical escape your own!

3 Beds ⋅ 2 Baths ⋅ 621461 MLS

Completed in 2025, this brand-new, elevated two-story home rises above the surrounding homes and is built above flood level. Excellent location close to the beach. Category 5 hurricane-rated construction, impact windows and doors, and Hardie board siding combine coastal style with storm protection. The home offers 3 bedrooms and 3 bathrooms, plus an office currently set up with bunk beds as a fourth sleeping space. Separate laundry room. The backyard is a gorgeous tropical retreat. A large heated pool and spa are surrounded by a gorgeous stone deck, lush landscaping and dramatic evening lighting. A huge poolside Tiki hut creates a spectacular setting for shaded dining, lounging and entertaining, while a putting green adds to the fun. Generous gathering areas and a completely fenced yard make this outdoor oasis perfect for sunny afternoons and unforgettable evenings beneath the palms. Inside, bright, open living and dining spaces flow into a beautiful kitchen with white cabinetry, stainless steel appliances, a blue tile backsplash and a generous island with seating. Balconies extend the living space outdoors. Beneath the home, a large covered area offers room to watch sports, relax and entertain, or serve as a carport. A permitted downstairs enclosure provides valuable storage and pool cabana. New construction, an elevated setting and an exceptional backyard come together in one remarkable property. Don't miss your opportunity to make this tropical escape your own!

1716 Laird St, Key West

$1,350,000

Welcome to the Sanctuary! This UPDATED/REMODELED gated single family POOL home is located on the 18th hole of the world famous Rees Jones designed Key West Golf Course. 1600 sq ft of living space with 3 bedrooms and 2.5 bathrooms. This 2 story home features an open floor plan with 9 ft ceilings and lots of windows allowing in natural light. An updated half bath is conveniently located on the first floor. The kitchen was updated with Calcutta Quartz countertops, ceramic plank tile backsplash resembling a weathered coastal wood and stainless steel Cafe appliances. Travel up the stairs with new Bamboo flooring to 3 bedrooms and 2 more updated baths. The Primary Suite features a Spa Like Escape bath with waterfall shower. French doors off the Primary Suite open to a screened balcony porch with views of tropical foliage and private pool. The pool was recently resurfaced and the pool pump and pool heater replaced. Sprinkler system also replaced. Freshly painted exterior. 24 hour security, fitness room, additional community pool are just a few of the amenities this property offers. You don't want to miss this beautiful turn key home in one of the most tranquil settings in Key West. It's a true Coastal Charmer!

3 Beds ⋅ 3 Baths ⋅ 621423 MLS

Welcome to the Sanctuary! This UPDATED/REMODELED gated single family POOL home is located on the 18th hole of the world famous Rees Jones designed Key West Golf Course. 1600 sq ft of living space with 3 bedrooms and 2.5 bathrooms. This 2 story home features an open floor plan with 9 ft ceilings and lots of windows allowing in natural light. An updated half bath is conveniently located on the first floor. The kitchen was updated with Calcutta Quartz countertops, ceramic plank tile backsplash resembling a weathered coastal wood and stainless steel Cafe appliances. Travel up the stairs with new Bamboo flooring to 3 bedrooms and 2 more updated baths. The Primary Suite features a Spa Like Escape bath with waterfall shower. French doors off the Primary Suite open to a screened balcony porch with views of tropical foliage and private pool. The pool was recently resurfaced and the pool pump and pool heater replaced. Sprinkler system also replaced. Freshly painted exterior. 24 hour security, fitness room, additional community pool are just a few of the amenities this property offers. You don't want to miss this beautiful turn key home in one of the most tranquil settings in Key West. It's a true Coastal Charmer!

197 Golf Club Dr, Key West

$989,000

Built in 1899, 418 Amelia Street is where Key West history, privacy, and the perfect location converge. Behind classic wood siding and Bahama shutters, this two-bedroom, two-bath residence with a bonus loft/finished attic makes thoughtful and intentional use of its 861 interior square feet, featuring an updated kitchen and an easy flow that extends naturally outdoors to the large covered deck and garden. A private, palm-shaded plunge pool anchors the garden, the privacy fence creating your own secluded retreat in the heart of the island. Traditional Conch architecture, mature tropical landscaping and intimate outdoor living endow the property with a sense of place that gives authentic Key West. Less than a block from Upper Duval, the home sits within easy reach of the Hemingway Home, Southernmost Point, art galleries, fine dining restaurants and the quieter residential streets of Old Town. This hidden gem offers the rare ability to step directly into the energy of Key West and return home to a private oasis steps away from it all. For the buyer seeking a 2-bedroom Old Town home with a private pool, tropical garden, and an exceptional walkable location, 418 Amelia Street is the one you've been waiting for.

2 Beds ⋅ 2 Baths ⋅ 621361 MLS

Built in 1899, 418 Amelia Street is where Key West history, privacy, and the perfect location converge. Behind classic wood siding and Bahama shutters, this two-bedroom, two-bath residence with a bonus loft/finished attic makes thoughtful and intentional use of its 861 interior square feet, featuring an updated kitchen and an easy flow that extends naturally outdoors to the large covered deck and garden. A private, palm-shaded plunge pool anchors the garden, the privacy fence creating your own secluded retreat in the heart of the island. Traditional Conch architecture, mature tropical landscaping and intimate outdoor living endow the property with a sense of place that gives authentic Key West. Less than a block from Upper Duval, the home sits within easy reach of the Hemingway Home, Southernmost Point, art galleries, fine dining restaurants and the quieter residential streets of Old Town. This hidden gem offers the rare ability to step directly into the energy of Key West and return home to a private oasis steps away from it all. For the buyer seeking a 2-bedroom Old Town home with a private pool, tropical garden, and an exceptional walkable location, 418 Amelia Street is the one you've been waiting for.

418 Amelia St, Key West

$2,919,000

Some homes in Key West give you a view. This one gives you an entire private world. Tucked behind its own gates on a lush 12,000-square-foot lot, 3615 Eagle Avenue is a custom-built retreat where a botanical garden isn't a backyard feature -- it's the whole point. Mature native palms, flowering tropical plants, and a resident population of birds and butterflies surround the home on every side, and nearly every room has been designed to keep that view in constant reach, with walls of impact-rated glass doors blurring the line between inside and out. Inside, cathedral ceilings and wide-plank tile floors set a calm, airy tone across sweeping one-level living space. The kitchen is built for people who actually cook and entertain -- Sub-Zero refrigeration, a gas range, dual dishwashers, a wine cooler, and an ice machine, all within reach of the garden views. The primary suite sits privately at the front of the home, paired with a fully renovated spa-style bath. A flexible office/den off the main living space easily converts to a fourth bedroom for guests, in-laws, or a work-from-home setup. Step outside to a covered pavilion overlooking a heated 33-foot pool and spa, connected by a sand pathway that winds through the garden -- an entertaining space that feels more resort than residential. A generator, oversized double-car garage with built-in storage, and covered parking for three additional vehicles round out the practical side of island living. This is a rare offering: real privacy, real green space, and real craftsmanship, minutes from everything that makes Key West Key West.

3 Beds ⋅ 4 Baths ⋅ 621305 MLS

Some homes in Key West give you a view. This one gives you an entire private world. Tucked behind its own gates on a lush 12,000-square-foot lot, 3615 Eagle Avenue is a custom-built retreat where a botanical garden isn't a backyard feature -- it's the whole point. Mature native palms, flowering tropical plants, and a resident population of birds and butterflies surround the home on every side, and nearly every room has been designed to keep that view in constant reach, with walls of impact-rated glass doors blurring the line between inside and out. Inside, cathedral ceilings and wide-plank tile floors set a calm, airy tone across sweeping one-level living space. The kitchen is built for people who actually cook and entertain -- Sub-Zero refrigeration, a gas range, dual dishwashers, a wine cooler, and an ice machine, all within reach of the garden views. The primary suite sits privately at the front of the home, paired with a fully renovated spa-style bath. A flexible office/den off the main living space easily converts to a fourth bedroom for guests, in-laws, or a work-from-home setup. Step outside to a covered pavilion overlooking a heated 33-foot pool and spa, connected by a sand pathway that winds through the garden -- an entertaining space that feels more resort than residential. A generator, oversized double-car garage with built-in storage, and covered parking for three additional vehicles round out the practical side of island living. This is a rare offering: real privacy, real green space, and real craftsmanship, minutes from everything that makes Key West Key West.

3615 Eagle Ave, Key West

$2,525,000

Set on a quiet, tree-lined block in one of Key West's most sought-after residential pockets, this thoughtfully reimagined 4BD/3BA residence offers just over 2,000 square feet of refined island living -- the result of a multi-year renovation where no detail was overlooked. The first floor opens to a flexible bedroom or private office alongside a full bath, newly converted and finished to the same standard as the rest of the home. Beyond, an all-new updated kitchen anchors the space with stainless appliances, custom built-in cabinetry, fresh countertops and designer lighting. French doors wrap the open living room, flooding the interior with natural light and dissolving the line between inside and out. Step through to your private tropical oasis: a heated pool, newly resurfaced and framed in travertine, with a new outdoor shower for rinsing off after a day at the beach. A setting built equally for quiet mornings and evenings. Upstairs, the primary suite delivers an ensuite bath, walk-in closet and a private balcony made for morning coffee above the palms. Two additional guest bedrooms and a full guest bath complete the second floor. Behind the finishes, the seller has invested in everything that matters: new HVAC, on-demand hot water, all-new pool equipment, new tile flooring, baseboards and lighting throughout, plus fresh interior and exterior paint. Renovated bathrooms and updated floors carry the same considered hand from room to room. A short bike ride delivers you to Key West's finest restaurants, beaches, galleries, museums and world-famous Duval Street -- yet the block itself stays wonderfully removed from it all. A neighborhood stunner not to be missed.

4 Beds ⋅ 3 Baths ⋅ 621162 MLS

Set on a quiet, tree-lined block in one of Key West's most sought-after residential pockets, this thoughtfully reimagined 4BD/3BA residence offers just over 2,000 square feet of refined island living -- the result of a multi-year renovation where no detail was overlooked. The first floor opens to a flexible bedroom or private office alongside a full bath, newly converted and finished to the same standard as the rest of the home. Beyond, an all-new updated kitchen anchors the space with stainless appliances, custom built-in cabinetry, fresh countertops and designer lighting. French doors wrap the open living room, flooding the interior with natural light and dissolving the line between inside and out. Step through to your private tropical oasis: a heated pool, newly resurfaced and framed in travertine, with a new outdoor shower for rinsing off after a day at the beach. A setting built equally for quiet mornings and evenings. Upstairs, the primary suite delivers an ensuite bath, walk-in closet and a private balcony made for morning coffee above the palms. Two additional guest bedrooms and a full guest bath complete the second floor. Behind the finishes, the seller has invested in everything that matters: new HVAC, on-demand hot water, all-new pool equipment, new tile flooring, baseboards and lighting throughout, plus fresh interior and exterior paint. Renovated bathrooms and updated floors carry the same considered hand from room to room. A short bike ride delivers you to Key West's finest restaurants, beaches, galleries, museums and world-famous Duval Street -- yet the block itself stays wonderfully removed from it all. A neighborhood stunner not to be missed.

1427 Washington St, Key West

$9,495,000

Rare Opportunity: The Only Home For Sale on Crescent Beach, Sunset Key Welcome to 11 Sunset Key Drive -- a fully renovated retreat on the most exclusive private island in the Florida Keys, and the only property currently available on Crescent Beach. Accessible exclusively by private ferry, Sunset Key offers a rare combination of true seclusion and effortless proximity to Old Town Key West, just minutes away. Completely renovated in 2018 with over $1.7 million invested, this 3-bedroom, 2.5-bath, close to 3,000-square-foot home was rebuilt for easy island living: hurricane-impact doors and windows, an updated roof, all-new electrical and white oak engineered wood flooring, a new interior fire suppression sprinkler system, and a full exterior and interior repaint. The kitchen centers on a Sub-Zero refrigerator, new stainless appliances, new countertops and custom cabinetry, while the private pool/spa was rebuilt down to the plumbing with new handcrafted and hand painted tile, equipment, heater, LED lighting and all app-controlled. Fully furnished by Restoration Hardware and ready to move into exactly as it is. Ownership here includes access to an oceanfront restaurant, full-service spa, fitness center, tennis courts, and private beaches -- all steps from the front door. Sunset Key holds only a handful of homes, and Crescent Beach holds fewer still. Schedule your private showing today. See you soon!!!

3 Beds ⋅ 3 Baths ⋅ 621128 MLS

Rare Opportunity: The Only Home For Sale on Crescent Beach, Sunset Key Welcome to 11 Sunset Key Drive -- a fully renovated retreat on the most exclusive private island in the Florida Keys, and the only property currently available on Crescent Beach. Accessible exclusively by private ferry, Sunset Key offers a rare combination of true seclusion and effortless proximity to Old Town Key West, just minutes away. Completely renovated in 2018 with over $1.7 million invested, this 3-bedroom, 2.5-bath, close to 3,000-square-foot home was rebuilt for easy island living: hurricane-impact doors and windows, an updated roof, all-new electrical and white oak engineered wood flooring, a new interior fire suppression sprinkler system, and a full exterior and interior repaint. The kitchen centers on a Sub-Zero refrigerator, new stainless appliances, new countertops and custom cabinetry, while the private pool/spa was rebuilt down to the plumbing with new handcrafted and hand painted tile, equipment, heater, LED lighting and all app-controlled. Fully furnished by Restoration Hardware and ready to move into exactly as it is. Ownership here includes access to an oceanfront restaurant, full-service spa, fitness center, tennis courts, and private beaches -- all steps from the front door. Sunset Key holds only a handful of homes, and Crescent Beach holds fewer still. Schedule your private showing today. See you soon!!!

11 Sunset, Key West

$649,000

There are homes that simply check the boxes--then there are homes that immediately feel like ''home.'' Tucked on a quiet, 1-way lane w/in Key West Golf Club, 19 Spoonbill enjoys a superbly tranquil setting overlooking the lush, colorful Butterfly Garden/pond. The pace seems to slow. From the newly built composite rear veranda/rear steps, the gentle trickle of water from the Butterfly Garden statue becomes part of the soundtrack. Tropical greenery creates a peaceful backdrop for morning coffee/afternoon relaxation/evening glass of wine. Exceptional Location. Community Center/Fitness Room/HOA Office are just steps away, while the spectacular lagoon-shaped community pool w/tropical waterfalls is only a short stroll through the garden or down the inviting lane. Everyday living feels a little more like a Key West escape. Inside/out, this pristine residence has been given an extraordinary level of care. Freshly painted throughout, the home is sparkling, warm & inviting! For the homeowner seeking a property where the hard work has already been done, this one is the answer. Impressive exterior renovation. The entire front fence/gate has been meticulously rebuilt, posts/pickets re-secured w/ stainless-steel fasteners, 5 new pressure-treated wood panels. Front lower veranda has been completely rebuilt, enhanced w/new composite picture framing, rich English Walnut composite decking/new stair stringers, posts wrapped in composite sleeves/new composite railings. Upper belt/trim on the front/rear replaced w/Azek, secured w/stainless fasteners. Side/rear fencing was carefully re-secured, new pickets/new gate added. Freshly painted white trim/soffits/gutters/rails/balusters complete the polished exterior presentation. 4 brand-new stainless Frigidaire Gallery Series appliances. Wainscoting accented stairwell/rich wooden stairs/flooring upstairs, 2 glorious upper verandas, new lighting fixtures, 2021 AC, tented in 2018/continued Orkin treatment plan, solar lighting. LOOK NO FURTHER

2 Beds ⋅ 2 Baths ⋅ 620820 MLS

There are homes that simply check the boxes--then there are homes that immediately feel like ''home.'' Tucked on a quiet, 1-way lane w/in Key West Golf Club, 19 Spoonbill enjoys a superbly tranquil setting overlooking the lush, colorful Butterfly Garden/pond. The pace seems to slow. From the newly built composite rear veranda/rear steps, the gentle trickle of water from the Butterfly Garden statue becomes part of the soundtrack. Tropical greenery creates a peaceful backdrop for morning coffee/afternoon relaxation/evening glass of wine. Exceptional Location. Community Center/Fitness Room/HOA Office are just steps away, while the spectacular lagoon-shaped community pool w/tropical waterfalls is only a short stroll through the garden or down the inviting lane. Everyday living feels a little more like a Key West escape. Inside/out, this pristine residence has been given an extraordinary level of care. Freshly painted throughout, the home is sparkling, warm & inviting! For the homeowner seeking a property where the hard work has already been done, this one is the answer. Impressive exterior renovation. The entire front fence/gate has been meticulously rebuilt, posts/pickets re-secured w/ stainless-steel fasteners, 5 new pressure-treated wood panels. Front lower veranda has been completely rebuilt, enhanced w/new composite picture framing, rich English Walnut composite decking/new stair stringers, posts wrapped in composite sleeves/new composite railings. Upper belt/trim on the front/rear replaced w/Azek, secured w/stainless fasteners. Side/rear fencing was carefully re-secured, new pickets/new gate added. Freshly painted white trim/soffits/gutters/rails/balusters complete the polished exterior presentation. 4 brand-new stainless Frigidaire Gallery Series appliances. Wainscoting accented stairwell/rich wooden stairs/flooring upstairs, 2 glorious upper verandas, new lighting fixtures, 2021 AC, tented in 2018/continued Orkin treatment plan, solar lighting. LOOK NO FURTHER

19 Spoonbill Way, Key West

$12,500,000

A distinguished offering on one of Key West's most coveted private island enclaves, 32 Sunset Key Drive embodies the ease, elegance, and exclusivity of waterfront living. One of the largest custom residences on Sunset Key, this 3,635-square-foot oceanfront estate was conceived by its original owners with an unwavering commitment to craftsmanship, comfort, and detail. Set beside its own private beach, the home features six ensuite bedrooms and seven full baths, creating a refined retreat designed for gracious hosting and effortless relaxation. Inside, coffered wood-paneled ceilings, tumbled marble, and solid oak floors lend depth, texture, and timeless coastal sophistication. Expansive living, dining, and kitchen spaces open naturally to the outdoors, blurring the line between interior comfort and the island's spectacular waterfront setting. Beyond, a custom rock pool with a hot tub and two-story slide evokes the atmosphere of a private resort, while a fully equipped outdoor kitchen, full bath, shower, and laundry facility elevate every gathering with ease and intention. Hop on the five minute ferry ride to your island paradise, enjoy the fabulous spa and dine at the acclaimed restaurant Latitudes. Truly, this is a one of a kind opportunity for the discerning buyer.

6 Beds ⋅ 7 Baths ⋅ 620770 MLS

A distinguished offering on one of Key West's most coveted private island enclaves, 32 Sunset Key Drive embodies the ease, elegance, and exclusivity of waterfront living. One of the largest custom residences on Sunset Key, this 3,635-square-foot oceanfront estate was conceived by its original owners with an unwavering commitment to craftsmanship, comfort, and detail. Set beside its own private beach, the home features six ensuite bedrooms and seven full baths, creating a refined retreat designed for gracious hosting and effortless relaxation. Inside, coffered wood-paneled ceilings, tumbled marble, and solid oak floors lend depth, texture, and timeless coastal sophistication. Expansive living, dining, and kitchen spaces open naturally to the outdoors, blurring the line between interior comfort and the island's spectacular waterfront setting. Beyond, a custom rock pool with a hot tub and two-story slide evokes the atmosphere of a private resort, while a fully equipped outdoor kitchen, full bath, shower, and laundry facility elevate every gathering with ease and intention. Hop on the five minute ferry ride to your island paradise, enjoy the fabulous spa and dine at the acclaimed restaurant Latitudes. Truly, this is a one of a kind opportunity for the discerning buyer.

32 Sunset, Key West

$599,000

Life feels a little slower in the Casa Marina neighborhood. Mornings begin with a walk to Higgs Beach, afternoons are spent by the pool, and evenings often end just down the street at Salute! on the Beach or Louie's Backyard. Tucked within the peaceful Southpark Condominium community, 816 South Street, Unit 4 places you in the heart of one of Key West's most desirable locations while offering the privacy and simplicity of low maintenance island living. Inside, this 1 bedroom, 1 bathroom condominium feels bright, comfortable, and welcoming. The open living spaces flow naturally to two private outdoor decks, one at the front of the home that is perfect for enjoying the neighborhood atmosphere and another tucked just off the bedroom, surrounded by mature tropical landscaping for a more private escape. The community itself offers the amenities that make everyday living feel like a vacation, including a beautifully maintained heated swimming pool set among lush tropical grounds. An assigned off street parking space and a spacious locked storage area provide conveniences that are increasingly valuable in Key West. Located just 4 blocks from Duval Street, you can easily walk or bike to beaches, restaurants, galleries, shopping, and everything that makes island life so special, while still returning home to one of the quieter residential pockets of Old Town. Whether you are searching for a full time residence, a seasonal retreat, or simply a place where life naturally slows down, 816 South Street, Unit 4 offers an opportunity to experience the very best of Casa Marina living.

1 Beds ⋅ 1 Baths ⋅ 620722 MLS

Life feels a little slower in the Casa Marina neighborhood. Mornings begin with a walk to Higgs Beach, afternoons are spent by the pool, and evenings often end just down the street at Salute! on the Beach or Louie's Backyard. Tucked within the peaceful Southpark Condominium community, 816 South Street, Unit 4 places you in the heart of one of Key West's most desirable locations while offering the privacy and simplicity of low maintenance island living. Inside, this 1 bedroom, 1 bathroom condominium feels bright, comfortable, and welcoming. The open living spaces flow naturally to two private outdoor decks, one at the front of the home that is perfect for enjoying the neighborhood atmosphere and another tucked just off the bedroom, surrounded by mature tropical landscaping for a more private escape. The community itself offers the amenities that make everyday living feel like a vacation, including a beautifully maintained heated swimming pool set among lush tropical grounds. An assigned off street parking space and a spacious locked storage area provide conveniences that are increasingly valuable in Key West. Located just 4 blocks from Duval Street, you can easily walk or bike to beaches, restaurants, galleries, shopping, and everything that makes island life so special, while still returning home to one of the quieter residential pockets of Old Town. Whether you are searching for a full time residence, a seasonal retreat, or simply a place where life naturally slows down, 816 South Street, Unit 4 offers an opportunity to experience the very best of Casa Marina living.

816 S St Unit 4, Key West

$1,695,000

Fully furnished, 2b/2b designer-complete home is close to the heart of Old Town Key West, yet far enough from the maddening crowd. Late-1800s Conch house with detached guest cottage were gutted, reconfigured and restored in 2021. New roof, infrastructure and new state-of-the-art chef's kitchen. Casement windows open to the back garden that has 8 varieties of bananas. And what a fine garden it is: Orchids & herbs & fruit, oh my. Salvaged Dade County pine walls light up with windows galore. A side yard connects the 1b/1b primary residence to the en-suite detached cottage. On-demand hot water heater. Outdoor shower. Hot tub. Off-street parking. Rear garden entrance to property from Havana Lane offers front and back access. Meticulous detail throughout makes this A MUST SEE. Low fee insurance costs available upon request.

2 Beds ⋅ 2 Baths ⋅ 620684 MLS

Fully furnished, 2b/2b designer-complete home is close to the heart of Old Town Key West, yet far enough from the maddening crowd. Late-1800s Conch house with detached guest cottage were gutted, reconfigured and restored in 2021. New roof, infrastructure and new state-of-the-art chef's kitchen. Casement windows open to the back garden that has 8 varieties of bananas. And what a fine garden it is: Orchids & herbs & fruit, oh my. Salvaged Dade County pine walls light up with windows galore. A side yard connects the 1b/1b primary residence to the en-suite detached cottage. On-demand hot water heater. Outdoor shower. Hot tub. Off-street parking. Rear garden entrance to property from Havana Lane offers front and back access. Meticulous detail throughout makes this A MUST SEE. Low fee insurance costs available upon request.

907 Frances St, Key West

$1,825,000

RARE OPPORTUNITY TO PURCHASE IN CASA MARINA FOR ONLY $835 PRICE PER SQUARE FOOT. (34% BELOW market value) Life feels a little different in Casa Marina. The streets are quieter, the homes are beautifully maintained, and everything from the beach to Old Town is just a short walk or bike ride away. Tucked within one of Key West's most desirable neighborhoods, 1115 South Street captures everything people love about living here. Step inside and the home immediately feels open and inviting. Ten foot ceilings, warm Brazilian cherry floors, and an abundance of natural light create spaces that feel both elegant and comfortable. The entire first floor is designed for gathering, anchored by an impressive kitchen with abundant cabinetry, expansive countertops, and high end appliances that make cooking and entertaining equally enjoyable. As beautiful as the interior is, your attention naturally shifts outdoors. French doors open to a private tropical backyard where a large swimming pool, separate hot tub, and coral stone patios with IPE decking create a peaceful setting for relaxing or entertaining. Surrounded by mature landscaping, the backyard feels like your own private retreat. With both bedrooms located upstairs, the home offers a thoughtful separation between everyday living and personal space. The primary suite even enjoys its own balcony overlooking the backyard, providing a quiet place to begin or end the day. Beautifully maintained and thoughtfully designed, this is a home where every detail encourages you to slow down, entertain often, and enjoy the best of Key West living.

2 Beds ⋅ 2 Baths ⋅ 620470 MLS

RARE OPPORTUNITY TO PURCHASE IN CASA MARINA FOR ONLY $835 PRICE PER SQUARE FOOT. (34% BELOW market value) Life feels a little different in Casa Marina. The streets are quieter, the homes are beautifully maintained, and everything from the beach to Old Town is just a short walk or bike ride away. Tucked within one of Key West's most desirable neighborhoods, 1115 South Street captures everything people love about living here. Step inside and the home immediately feels open and inviting. Ten foot ceilings, warm Brazilian cherry floors, and an abundance of natural light create spaces that feel both elegant and comfortable. The entire first floor is designed for gathering, anchored by an impressive kitchen with abundant cabinetry, expansive countertops, and high end appliances that make cooking and entertaining equally enjoyable. As beautiful as the interior is, your attention naturally shifts outdoors. French doors open to a private tropical backyard where a large swimming pool, separate hot tub, and coral stone patios with IPE decking create a peaceful setting for relaxing or entertaining. Surrounded by mature landscaping, the backyard feels like your own private retreat. With both bedrooms located upstairs, the home offers a thoughtful separation between everyday living and personal space. The primary suite even enjoys its own balcony overlooking the backyard, providing a quiet place to begin or end the day. Beautifully maintained and thoughtfully designed, this is a home where every detail encourages you to slow down, entertain often, and enjoy the best of Key West living.

1115 South Street, Key West

$950,000

Coastal Living at 1800 Atlantic - where everyday life is framed by ocean breezes and turquoise water. This highly sought-after oceanfront condominium community offers the rare privilege of walking distance to Smather's Beach on the Atlantic, minutes from the airport, and the effortless ease that makes Key West living so desirable. Stroll along the shoreline in the morning, watch boats drift along the horizon, and spend your afternoons relaxing beside the resort-style Olympic-size heated pool and spa, all set within lush tropical landscaping. Residents enjoy tennis and pickleball courts, an equipped fitness center, assigned covered parking, and professionally maintained grounds--delivering true comfort, simplicity, and peace of mind in a coastal setting. Recent upgrades include impact-rated doors and windows, enhancing storm protection, energy efficiency, and long-term ownership confidence while maintaining a clean, modern coastal aesthetic. Pet owners will appreciate the flexibility of 2 pets allowed (up to 50 lbs total). Monthly association fees include building insurance, exterior maintenance, professional management, water, high-speed internet - offering a truly turnkey lifestyle. Ideally located just minutes from Old Town Key West, you're close to world-class dining, galleries, marinas, and cultural events, yet tucked away in a quiet, oceanfront enclave that feels removed from it all. Whether by bike or a short drive, everything the island offers is within easy reach. Come experience why so many call this their Key West home away from home 🌴.

2 Beds ⋅ 2 Baths ⋅ 620451 MLS

Coastal Living at 1800 Atlantic - where everyday life is framed by ocean breezes and turquoise water. This highly sought-after oceanfront condominium community offers the rare privilege of walking distance to Smather's Beach on the Atlantic, minutes from the airport, and the effortless ease that makes Key West living so desirable. Stroll along the shoreline in the morning, watch boats drift along the horizon, and spend your afternoons relaxing beside the resort-style Olympic-size heated pool and spa, all set within lush tropical landscaping. Residents enjoy tennis and pickleball courts, an equipped fitness center, assigned covered parking, and professionally maintained grounds--delivering true comfort, simplicity, and peace of mind in a coastal setting. Recent upgrades include impact-rated doors and windows, enhancing storm protection, energy efficiency, and long-term ownership confidence while maintaining a clean, modern coastal aesthetic. Pet owners will appreciate the flexibility of 2 pets allowed (up to 50 lbs total). Monthly association fees include building insurance, exterior maintenance, professional management, water, high-speed internet - offering a truly turnkey lifestyle. Ideally located just minutes from Old Town Key West, you're close to world-class dining, galleries, marinas, and cultural events, yet tucked away in a quiet, oceanfront enclave that feels removed from it all. Whether by bike or a short drive, everything the island offers is within easy reach. Come experience why so many call this their Key West home away from home 🌴.

1800 Atlantic Blvd Unit 218B, Key West

$3,495,000

Caroline Street, steps from the Historic Seaport. This is the Key West people picture before they ever get here. Built in the late 1800s as a cigar factory, when Key West was the cigar capital of the country. That origin is why it lives so much larger than the cottages around it: the volume, the ceiling height, the proportions of a working building rather than a bungalow. The Dade County pine is original, refinished rather than replaced, and irreplaceable. What 2023 changed was everything behind it -- raised to modern flood elevation, impact-rated windows and doors, and finishes chosen by a designer who wasn't in a hurry. Native coral walls, Jerusalem limestone, terrazzo, and marble under high ceilings. Out front, double balconies span the facade -- the real living room here. Coffee on the upper, cocktails on the lower, and Caroline Street putting on its show below: the walk to the Seaport, the whole slow parade of Old Town. Out back, collapsing glass doors open to the garden: a heated and chilled plunge pool with waterfall, walled and private -- the kind of courtyard that makes 4pm the best hour of the day. Four bedrooms, four en-suite baths, plus a guest half bath. The oversized upstairs primary has walk-in closets and a spa-caliber bath with double shower, artist-made cabinetry, and coral detail you won't see twice. A second primary on the main floor adds flexibility, plus a loft/office upstairs. The kitchen was built for how people actually entertain here: a six-seat island, full JennAir appliance package, open flow to the living and dining rooms. And it earns from day one. Six-figures in booked rental revenue transfers with the sale, repeat guests already on the calendar. Residence, winter escape, or income property -- it does all three. Sold furnished. No HOA. Seller financing possible. Three minutes to Duval. One minute to the shrimp boats. Homes on this block rarely trade, and almost never finished like this.

4 Beds ⋅ 5 Baths ⋅ 620222 MLS

Caroline Street, steps from the Historic Seaport. This is the Key West people picture before they ever get here. Built in the late 1800s as a cigar factory, when Key West was the cigar capital of the country. That origin is why it lives so much larger than the cottages around it: the volume, the ceiling height, the proportions of a working building rather than a bungalow. The Dade County pine is original, refinished rather than replaced, and irreplaceable. What 2023 changed was everything behind it -- raised to modern flood elevation, impact-rated windows and doors, and finishes chosen by a designer who wasn't in a hurry. Native coral walls, Jerusalem limestone, terrazzo, and marble under high ceilings. Out front, double balconies span the facade -- the real living room here. Coffee on the upper, cocktails on the lower, and Caroline Street putting on its show below: the walk to the Seaport, the whole slow parade of Old Town. Out back, collapsing glass doors open to the garden: a heated and chilled plunge pool with waterfall, walled and private -- the kind of courtyard that makes 4pm the best hour of the day. Four bedrooms, four en-suite baths, plus a guest half bath. The oversized upstairs primary has walk-in closets and a spa-caliber bath with double shower, artist-made cabinetry, and coral detail you won't see twice. A second primary on the main floor adds flexibility, plus a loft/office upstairs. The kitchen was built for how people actually entertain here: a six-seat island, full JennAir appliance package, open flow to the living and dining rooms. And it earns from day one. Six-figures in booked rental revenue transfers with the sale, repeat guests already on the calendar. Residence, winter escape, or income property -- it does all three. Sold furnished. No HOA. Seller financing possible. Three minutes to Duval. One minute to the shrimp boats. Homes on this block rarely trade, and almost never finished like this.

710 Caroline St, Key West

$1,799,000

There is something special about a home where everything has already been done for you, and at 2101 Harris Avenue, all that is left is to move in and start enjoying it! Completely reimagined from top to bottom in 2025, this beautifully renovated Midtown East home feels fresh, welcoming, and ready for its next chapter. Set on a fully fenced corner lot with all new landscaping, the property offers both privacy and convenience, just minutes from schools, restaurants, shopping, and everything that makes Key West so special. Inside, sunlight fills the home through impact windows and doors, filling the home with a bright and airy feel. At the center of it all is a beautifully designed kitchen, where a large island with waterfall quartz counters comfortably seats 4 and naturally becomes the place where family and friends gather. From there, everything flows effortlessly outdoors. Large entertaining spaces connect beautifully to the covered rear porch and pool area, making the home feel bigger, brighter, and built for gathering. Whether it is dinner with friends, a lazy afternoon by the water, or simply enjoying the view from inside, the connection between indoor and outdoor living feels natural and easy. The heated pool, complete with a shallow sun shelf, becomes the centerpiece of the backyard, surrounded by generous space for lounging and outdoor dining. The 3 bedroom, 2.5 bathroom layout is equally inviting, highlighted by a spacious primary suite featuring a large walk in closet and private balcony. Beautifully renovated and thoughtfully designed, this is a home ready to be enjoyed from day one.

3 Beds ⋅ 3 Baths ⋅ 620176 MLS

There is something special about a home where everything has already been done for you, and at 2101 Harris Avenue, all that is left is to move in and start enjoying it! Completely reimagined from top to bottom in 2025, this beautifully renovated Midtown East home feels fresh, welcoming, and ready for its next chapter. Set on a fully fenced corner lot with all new landscaping, the property offers both privacy and convenience, just minutes from schools, restaurants, shopping, and everything that makes Key West so special. Inside, sunlight fills the home through impact windows and doors, filling the home with a bright and airy feel. At the center of it all is a beautifully designed kitchen, where a large island with waterfall quartz counters comfortably seats 4 and naturally becomes the place where family and friends gather. From there, everything flows effortlessly outdoors. Large entertaining spaces connect beautifully to the covered rear porch and pool area, making the home feel bigger, brighter, and built for gathering. Whether it is dinner with friends, a lazy afternoon by the water, or simply enjoying the view from inside, the connection between indoor and outdoor living feels natural and easy. The heated pool, complete with a shallow sun shelf, becomes the centerpiece of the backyard, surrounded by generous space for lounging and outdoor dining. The 3 bedroom, 2.5 bathroom layout is equally inviting, highlighted by a spacious primary suite featuring a large walk in closet and private balcony. Beautifully renovated and thoughtfully designed, this is a home ready to be enjoyed from day one.

2101 Harris Ave, Key West

$2,499,000

Stunning modern home in New Town offering 2,525 sq. ft. of beautifully designed living space on an 8,250 sq. ft. lot. This 3-bedroom, 2 full + 2 half bath home features a desirable split floor plan with a private primary suite, complete with a walk-through closet and spa-like ensuite bath, plus two guest bedrooms and a full bath. The open-concept living, dining, and kitchen area is ideal for entertaining, highlighted by a 15-ft island and high-end Viking stainless steel appliances. The chef's kitchen also includes a wine cooler, ice maker, warming drawer, dual beverage drawers, and a dedicated coffee/wine station. Additional features include a walk-in pantry with drop-down desk, separate laundry room, and convenient half bath. Outdoor living is just as impressive, with French doors opening to a private backyard oasis featuring an Ipe wood deck, outdoor kitchen, outdoor shower, and an air-conditioned half bath. Enjoy the large heated pool and spa surrounded by lush landscaping. The property also offers a covered dual carport with built-in storage and additional brick parking for guests. Located just down the road from a public boat ramp and perfect for sunrise and sunset walks.

3 Beds ⋅ 4 Baths ⋅ 620092 MLS

Stunning modern home in New Town offering 2,525 sq. ft. of beautifully designed living space on an 8,250 sq. ft. lot. This 3-bedroom, 2 full + 2 half bath home features a desirable split floor plan with a private primary suite, complete with a walk-through closet and spa-like ensuite bath, plus two guest bedrooms and a full bath. The open-concept living, dining, and kitchen area is ideal for entertaining, highlighted by a 15-ft island and high-end Viking stainless steel appliances. The chef's kitchen also includes a wine cooler, ice maker, warming drawer, dual beverage drawers, and a dedicated coffee/wine station. Additional features include a walk-in pantry with drop-down desk, separate laundry room, and convenient half bath. Outdoor living is just as impressive, with French doors opening to a private backyard oasis featuring an Ipe wood deck, outdoor kitchen, outdoor shower, and an air-conditioned half bath. Enjoy the large heated pool and spa surrounded by lush landscaping. The property also offers a covered dual carport with built-in storage and additional brick parking for guests. Located just down the road from a public boat ramp and perfect for sunrise and sunset walks.

1511 17th Ter, Key West

$2,100,000

Wake up in Key West and own your own piece of the island! Come enjoy a second-home outdoor living lifestyle on almost 1/4 acre private fenced-in landscaped tropical grounds corner lot with heated salt water pool, large porch and deck entertainment area and outdoor kitchen and BBQ area. The first floor is set to entertaining with French Saltillo (terracotta) floors throughout, a gourmet kitchen (with new appliances), dining room, open living room, bedroom and bath and a mother-in-law / guest bedroom/bath with private entrance. A dramatic flowing staircase leads to the second floor primary master ensuite bedroom with private balcony over-looking the large heated salt water swimming pool, private lush indigenous tropical exotic orchid gardens and gazebo. With private gated entrance, off-street parking, plenty of outside storage areas, and many on-site updates (automatic yard lights, timed irrigation system, Ring cameras throughout, Aquilink pool and fountain control, new roof and gutters, new A/C system, new water heater, new Kohler generator) to name a few. With close proximity to Old Town - Enjoy our local bars, restaurants, museums, art galleries and shops, beaches, and seaport activities (all within 10 minutes), then come home to a bit of peace and quiet. Comes furnished, this charming home available to purchase and close on at your earliest convenience

3 Beds ⋅ 3 Baths ⋅ 619190 MLS

Wake up in Key West and own your own piece of the island! Come enjoy a second-home outdoor living lifestyle on almost 1/4 acre private fenced-in landscaped tropical grounds corner lot with heated salt water pool, large porch and deck entertainment area and outdoor kitchen and BBQ area. The first floor is set to entertaining with French Saltillo (terracotta) floors throughout, a gourmet kitchen (with new appliances), dining room, open living room, bedroom and bath and a mother-in-law / guest bedroom/bath with private entrance. A dramatic flowing staircase leads to the second floor primary master ensuite bedroom with private balcony over-looking the large heated salt water swimming pool, private lush indigenous tropical exotic orchid gardens and gazebo. With private gated entrance, off-street parking, plenty of outside storage areas, and many on-site updates (automatic yard lights, timed irrigation system, Ring cameras throughout, Aquilink pool and fountain control, new roof and gutters, new A/C system, new water heater, new Kohler generator) to name a few. With close proximity to Old Town - Enjoy our local bars, restaurants, museums, art galleries and shops, beaches, and seaport activities (all within 10 minutes), then come home to a bit of peace and quiet. Comes furnished, this charming home available to purchase and close on at your earliest convenience

3513 Sunrise Dr, Key West

$1,799,000

Tucked within the charm of Old Town Key West, this historic Eyebrow home invites a lifestyle shaped by tropical surroundings, outdoor living, and close proximity to the island's most recognized destinations. Set on a deep 4200+ square foot lot stretching from Eaton Street to Thompson Lane, the property offers 3 bedrooms and 2 baths in a setting designed for both everyday living and relaxed entertaining. Recognized as a 2016 Preservation Award Winner, this lovely home reflects thoughtful preservation of its architectural style while incorporating modern updates. Inside, a light-filled living area, and a main-level primary bedroom create a comfortable and functional layout. The open design flows naturally to the outdoor spaces, while the updated kitchen features white cabinetry, quartz countertops, stainless steel appliances, tile backsplash, and dedicated prep space, along with additional storage and an interior laundry area. French doors extend the living space outward to a covered deck and courtyard. The outdoor setting is a defining element of the home, centered around a private heated pool, covered lounge area and outdoor bathroom. Gorgeous palms and lush plantings frame the backyard, creating a private garden atmosphere with brick walkways and a spacious courtyard for dining and gathering, while string lighting enhances the space for evening ambiance. The deep lot includes off-street parking with a brick-paved driveway accessed from Thompson Lane, a valuable feature in Old Town. Just moments from the Historic Seaport, Duval Street, and some of Key West's most loved local spots, this location provides convenient access to dining, shopping, and live entertainment. With its combination of location, outdoor living spaces, and off-street parking, this property presents a compelling opportunity for use as a primary residence or vacation home in Old Town Key West..

3 Beds ⋅ 2 Baths ⋅ 619235 MLS

Tucked within the charm of Old Town Key West, this historic Eyebrow home invites a lifestyle shaped by tropical surroundings, outdoor living, and close proximity to the island's most recognized destinations. Set on a deep 4200+ square foot lot stretching from Eaton Street to Thompson Lane, the property offers 3 bedrooms and 2 baths in a setting designed for both everyday living and relaxed entertaining. Recognized as a 2016 Preservation Award Winner, this lovely home reflects thoughtful preservation of its architectural style while incorporating modern updates. Inside, a light-filled living area, and a main-level primary bedroom create a comfortable and functional layout. The open design flows naturally to the outdoor spaces, while the updated kitchen features white cabinetry, quartz countertops, stainless steel appliances, tile backsplash, and dedicated prep space, along with additional storage and an interior laundry area. French doors extend the living space outward to a covered deck and courtyard. The outdoor setting is a defining element of the home, centered around a private heated pool, covered lounge area and outdoor bathroom. Gorgeous palms and lush plantings frame the backyard, creating a private garden atmosphere with brick walkways and a spacious courtyard for dining and gathering, while string lighting enhances the space for evening ambiance. The deep lot includes off-street parking with a brick-paved driveway accessed from Thompson Lane, a valuable feature in Old Town. Just moments from the Historic Seaport, Duval Street, and some of Key West's most loved local spots, this location provides convenient access to dining, shopping, and live entertainment. With its combination of location, outdoor living spaces, and off-street parking, this property presents a compelling opportunity for use as a primary residence or vacation home in Old Town Key West..

1019 Eaton St, Key West

$1,250,000

This two-bedroom, two-bathroom condominium residence at Santa Maria Suites Resort offers both personal use and strong rental income potential. One of the resort's limited single-level units, the property produces nearly $200,000 in annual gross rental income and allows for transient nightly rentals. The floor plan features a generous living and dining area, full kitchen, and two private bedroom suites. Located just steps from iconic Duval Street, the property provides convenient access to Old Town restaurants, shops, and nightlife while maintaining a quiet resort setting. Resort amenities include swimming pool, fitness center, and off-street parking. Planned improvements to the residences, pool, and fitness areas are scheduled for completion in 2027. The current owner has paid the majority of the special assessment associated with these upgrades. Owners may choose their own rental management company or participate in the on-site program. Suitable for buyers seeking an income-producing investment, second home, or a combination of both.

2 Beds ⋅ 2 Baths ⋅ 619022 MLS

This two-bedroom, two-bathroom condominium residence at Santa Maria Suites Resort offers both personal use and strong rental income potential. One of the resort's limited single-level units, the property produces nearly $200,000 in annual gross rental income and allows for transient nightly rentals. The floor plan features a generous living and dining area, full kitchen, and two private bedroom suites. Located just steps from iconic Duval Street, the property provides convenient access to Old Town restaurants, shops, and nightlife while maintaining a quiet resort setting. Resort amenities include swimming pool, fitness center, and off-street parking. Planned improvements to the residences, pool, and fitness areas are scheduled for completion in 2027. The current owner has paid the majority of the special assessment associated with these upgrades. Owners may choose their own rental management company or participate in the on-site program. Suitable for buyers seeking an income-producing investment, second home, or a combination of both.

1401 Simonton St Unit # 11, Key West

$2,595,000

Price Reduction. Excellent opportunity to purchase a luxurious, modern, and refined single-family home in one of the best neighborhoods in Key West. This 4bed/3bath completely renovated and modern home is being offered completely furnished with all new furniture and ready for new owners. Just over 1930 S.F. of beautiful living space and situated on a 5,896 S. F. corner lot. This CBS home has all hurricane impact rated windows & doors, flood panels for all doors, and 25 KW Generac stand by whole house generator. There is an abundance of windows & doors allowing for plenty of natural light throughout the home. True chefs kitchen features gorgeous cabinets & counter tops with all stainless steel appliances. Dual ovens, gas stove top range, and wine cooler make your kitchen complete. The kitchen opens up to your amazing living & dining room areas. From there you will find this opens up to a super nice covered outdoor patio area, in ground, salt water, and heated 27L X 9W Jacuzzi & pool with water fall. Ready to kick back and relax. Outdoor areas have travertine tiles throughout and have lush native tropical landscaping with lighting & irrigation systems. Property has a 1 car covered carport and CBS privacy fencing around entire property. This home is located within walking distance to Higgs Beach, White St. Pier, and a short distance to Key West Best restaurants, beaches, museums, and art galleries. This is truly a home where modern luxury meets Key West paradise. Listing agents are related to the sellers.

4 Beds ⋅ 3 Baths ⋅ 614088 MLS

Price Reduction. Excellent opportunity to purchase a luxurious, modern, and refined single-family home in one of the best neighborhoods in Key West. This 4bed/3bath completely renovated and modern home is being offered completely furnished with all new furniture and ready for new owners. Just over 1930 S.F. of beautiful living space and situated on a 5,896 S. F. corner lot. This CBS home has all hurricane impact rated windows & doors, flood panels for all doors, and 25 KW Generac stand by whole house generator. There is an abundance of windows & doors allowing for plenty of natural light throughout the home. True chefs kitchen features gorgeous cabinets & counter tops with all stainless steel appliances. Dual ovens, gas stove top range, and wine cooler make your kitchen complete. The kitchen opens up to your amazing living & dining room areas. From there you will find this opens up to a super nice covered outdoor patio area, in ground, salt water, and heated 27L X 9W Jacuzzi & pool with water fall. Ready to kick back and relax. Outdoor areas have travertine tiles throughout and have lush native tropical landscaping with lighting & irrigation systems. Property has a 1 car covered carport and CBS privacy fencing around entire property. This home is located within walking distance to Higgs Beach, White St. Pier, and a short distance to Key West Best restaurants, beaches, museums, and art galleries. This is truly a home where modern luxury meets Key West paradise. Listing agents are related to the sellers.

1501 Florida St, Key West

$6,850,000

103 Front Street is a one of a kind masterpiece of architectural design and modern aesthetic. Built in the early 1900s, this imposing structure has been thouroughly restored and updated into a stunning home. The interior features a large great room with soaring ceilings, custom beams and woodwork. This home is perfect for entertaining on a large scale or enjoying a quiet evening. A dramatic staircase leads to a second floor walkway which is open to the main level. The floor plan provides privacy for each bedroom with the primary suite at one end of the hallway and a guest bedroom suite at the other end. Another guest bedroom and bath are on the first floor creating an option for a first floor primary bedroom. Custom features throughout are evidence of the artistic ingenuity used in the design of this impressive home. The kitchen features custom wood cabinets and granite countertops and is open to the dining area. Tall windows and french doors flood the home with sunlight. This home is perfect for indoor/outdoor entertaining. A wet bar features custom built ins plus an icemaker and refrigerator. Fronted by a white picket fence, the home sits back from the street and is adorned by tropical foliage. This unique structure with thick brick walls and impressivly tall windows offers passers by a glimpse of the historic origins of the Truman Annex. Its location in the heart of old town Key West provides easy walkability to the waterfront promenade, Ft. Taylor beach, cultural venues, shops and restaurants. The property comprises two lots with a large swimming pool and spa plus an outdoor shower between the covered and open air loggia and parking. There's plenty of space for entertaining outdoors under the palm trees. This estate home is one of a kind was restored to the highest standards. One must see this home to appreciate the incredible design and attention to detail that went into this historic treasure.

3 Beds ⋅ 3 Baths ⋅ 617136 MLS

103 Front Street is a one of a kind masterpiece of architectural design and modern aesthetic. Built in the early 1900s, this imposing structure has been thouroughly restored and updated into a stunning home. The interior features a large great room with soaring ceilings, custom beams and woodwork. This home is perfect for entertaining on a large scale or enjoying a quiet evening. A dramatic staircase leads to a second floor walkway which is open to the main level. The floor plan provides privacy for each bedroom with the primary suite at one end of the hallway and a guest bedroom suite at the other end. Another guest bedroom and bath are on the first floor creating an option for a first floor primary bedroom. Custom features throughout are evidence of the artistic ingenuity used in the design of this impressive home. The kitchen features custom wood cabinets and granite countertops and is open to the dining area. Tall windows and french doors flood the home with sunlight. This home is perfect for indoor/outdoor entertaining. A wet bar features custom built ins plus an icemaker and refrigerator. Fronted by a white picket fence, the home sits back from the street and is adorned by tropical foliage. This unique structure with thick brick walls and impressivly tall windows offers passers by a glimpse of the historic origins of the Truman Annex. Its location in the heart of old town Key West provides easy walkability to the waterfront promenade, Ft. Taylor beach, cultural venues, shops and restaurants. The property comprises two lots with a large swimming pool and spa plus an outdoor shower between the covered and open air loggia and parking. There's plenty of space for entertaining outdoors under the palm trees. This estate home is one of a kind was restored to the highest standards. One must see this home to appreciate the incredible design and attention to detail that went into this historic treasure.

103 Front St, Key West

$5,500,000

Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front porch welcome you to this 3,751 square foot property on an expansive 10,750 square foot lot that embodies historic Key West architecture. The main residence features four bedrooms, three and half baths of elegant living spaces, including a first-floor mother-in-law suite. Timeless design is found throughout with abundance of natural light and views of the lush, exotic landscape out every window. The great room features 12' ceilings, a curved wall of windows and French doors that lead to the serene, covered porch and outdoor dining space. The kitchen is a chef's dream equipped with new Viking appliances, ample counter space, and a view that overlooks the gorgeous, azure pool. The second level includes a spacious primary suite and two additional guest rooms, one of which has a balcony with treetop views and the island's best spot to view the spectacular 4th of July firework show. Two charming detached guest cottages tucked amongst the gardens offer secluded retreats each with full baths and one offering a living room and kitchenette. The outdoor oasis is defined by the oversized L-shaped pool and outdoor kitchen with built-in Viking grill; the perfect space for entertaining. This property is an exceptional, private sanctuary at an unbeatable location just one block from the crystal-clear Atlantic, tennis and pickleball courts, the esteemed Casa Marina Hotel and iconic White Street Pier. Don't miss the opportunity to call this remarkable estate your home! Seller is a licensed real estate broker and related to the listing agent. Seller is a licensed real estate broker and related to the listing agent.

6 Beds ⋅ 6 Baths ⋅ 618573 MLS

Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front porch welcome you to this 3,751 square foot property on an expansive 10,750 square foot lot that embodies historic Key West architecture. The main residence features four bedrooms, three and half baths of elegant living spaces, including a first-floor mother-in-law suite. Timeless design is found throughout with abundance of natural light and views of the lush, exotic landscape out every window. The great room features 12' ceilings, a curved wall of windows and French doors that lead to the serene, covered porch and outdoor dining space. The kitchen is a chef's dream equipped with new Viking appliances, ample counter space, and a view that overlooks the gorgeous, azure pool. The second level includes a spacious primary suite and two additional guest rooms, one of which has a balcony with treetop views and the island's best spot to view the spectacular 4th of July firework show. Two charming detached guest cottages tucked amongst the gardens offer secluded retreats each with full baths and one offering a living room and kitchenette. The outdoor oasis is defined by the oversized L-shaped pool and outdoor kitchen with built-in Viking grill; the perfect space for entertaining. This property is an exceptional, private sanctuary at an unbeatable location just one block from the crystal-clear Atlantic, tennis and pickleball courts, the esteemed Casa Marina Hotel and iconic White Street Pier. Don't miss the opportunity to call this remarkable estate your home! Seller is a licensed real estate broker and related to the listing agent. Seller is a licensed real estate broker and related to the listing agent.

906 Johnson St, Key West

$4,700,000

A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by legendary Key West developer David Wolkowsky and set behind privacy walls on an exceptional 11,730-square-foot corner double lot. Some homes are built. Others are authored. At its center: 40 feet of pool, surrounded by mature tropical landscaping and hardscape by Craig Reynolds Landscape Architecture, creating the feel of a private compound hidden in plain sight. Inside, the scale shifts again with 22-foot ceilings, walls of glass, 10-foot doors and sliders, custom teak, and a dramatic floor-to-ceiling library. The main residence offers two bedrooms and two-and-a-half baths, anchored by a chef's kitchen and expansive indoor-outdoor living. Extensive updates include new systems and impact-rated windows and doors. A completely separate one-bedroom guest house adds its own kitchen, laundry and private garden. 3 bedrooms. 3.5 baths. 3,104 square feet. 11,730 square feet of land. 40 feet of pool. In a market full of beautiful houses, 1014 Flagler offers something harder to replicate: a point of view.

3 Beds ⋅ 4 Baths ⋅ 618577 MLS

A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by legendary Key West developer David Wolkowsky and set behind privacy walls on an exceptional 11,730-square-foot corner double lot. Some homes are built. Others are authored. At its center: 40 feet of pool, surrounded by mature tropical landscaping and hardscape by Craig Reynolds Landscape Architecture, creating the feel of a private compound hidden in plain sight. Inside, the scale shifts again with 22-foot ceilings, walls of glass, 10-foot doors and sliders, custom teak, and a dramatic floor-to-ceiling library. The main residence offers two bedrooms and two-and-a-half baths, anchored by a chef's kitchen and expansive indoor-outdoor living. Extensive updates include new systems and impact-rated windows and doors. A completely separate one-bedroom guest house adds its own kitchen, laundry and private garden. 3 bedrooms. 3.5 baths. 3,104 square feet. 11,730 square feet of land. 40 feet of pool. In a market full of beautiful houses, 1014 Flagler offers something harder to replicate: a point of view.

1014 Flagler Ave, Key West

$3,599,000

1501 Georgia Street is a masterclass in design. Conceived by local architect Rob Delaune and set within lush, museum worthy grounds by renowned landscape architect Raymond Jungles, this striking 2,810sf residence sits on an expansive 8,800sf lot and captures the essence of tropical modernism. Clean lines. Soaring ceilings. Walls of glass. A seamless and intentional dialogue between indoors and out. This is true Mid Century Modern, authentically executed. A single story design with 4 bedrooms and 4.5 baths, wrapped in glass and stone, where skylights, pocket doors, and oversized windows flood the interiors with natural light. Every room frames the landscape, transforming the gardens into living artwork. Designed for both refined entertaining & comfortable family living, the home features stone floors throughout and a modern floor plan with garden views in every direction. Natural light fills the interiors, blurring the boundary between architecture and nature and creating a seamless indoor outdoor lifestyle that defines island living. At the heart of the home, a newly renovated showpiece kitchen elevates everyday life and gatherings alike, featuring dramatic Cambria quartz countertops with a waterfall island, warm wood cabinetry, pendant lighting, and stainless steel appliances. A full wall opens directly to the 55 foot heated and chilled saltwater pool and stone terrace, creating effortless flow for events large or intimate. The primary suite offers privacy and tranquil garden views, while all four bedrooms provide generous proportions and high ceilings. Oversized glass highlights the extraordinary tropical landscaping surrounding the home. The grounds showcase native and exotic flora from around the world, tropical atriums, a water garden with koi, multiple water features, an outdoor shower, and exceptional privacy inside & out. Properties of this caliber and architectural significance rarely become available, so don't wait, schedule your private showing today!

4 Beds ⋅ 5 Baths ⋅ 618829 MLS

1501 Georgia Street is a masterclass in design. Conceived by local architect Rob Delaune and set within lush, museum worthy grounds by renowned landscape architect Raymond Jungles, this striking 2,810sf residence sits on an expansive 8,800sf lot and captures the essence of tropical modernism. Clean lines. Soaring ceilings. Walls of glass. A seamless and intentional dialogue between indoors and out. This is true Mid Century Modern, authentically executed. A single story design with 4 bedrooms and 4.5 baths, wrapped in glass and stone, where skylights, pocket doors, and oversized windows flood the interiors with natural light. Every room frames the landscape, transforming the gardens into living artwork. Designed for both refined entertaining & comfortable family living, the home features stone floors throughout and a modern floor plan with garden views in every direction. Natural light fills the interiors, blurring the boundary between architecture and nature and creating a seamless indoor outdoor lifestyle that defines island living. At the heart of the home, a newly renovated showpiece kitchen elevates everyday life and gatherings alike, featuring dramatic Cambria quartz countertops with a waterfall island, warm wood cabinetry, pendant lighting, and stainless steel appliances. A full wall opens directly to the 55 foot heated and chilled saltwater pool and stone terrace, creating effortless flow for events large or intimate. The primary suite offers privacy and tranquil garden views, while all four bedrooms provide generous proportions and high ceilings. Oversized glass highlights the extraordinary tropical landscaping surrounding the home. The grounds showcase native and exotic flora from around the world, tropical atriums, a water garden with koi, multiple water features, an outdoor shower, and exceptional privacy inside & out. Properties of this caliber and architectural significance rarely become available, so don't wait, schedule your private showing today!

1501 Georgia St, Key West

$3,750,000

Charming Single family home with multiple guest cottages in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic districts, this property is just minutes away from famous landmarks, restaurants, and local shops. Take advantage of nearby beaches, water sports, and lush parks, offering a vibrant lifestyle for outdoor enthusiasts. This multifamily compound not only serves as a wonderful family home but also presents a lucrative rental opportunity in one of the most sought-after destinations in Florida. Don't miss your chance to own a piece of Key West history. Schedule a viewing today. Owner financing is available.

7 Beds ⋅ 8 Baths ⋅ 618468 MLS

Charming Single family home with multiple guest cottages in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic districts, this property is just minutes away from famous landmarks, restaurants, and local shops. Take advantage of nearby beaches, water sports, and lush parks, offering a vibrant lifestyle for outdoor enthusiasts. This multifamily compound not only serves as a wonderful family home but also presents a lucrative rental opportunity in one of the most sought-after destinations in Florida. Don't miss your chance to own a piece of Key West history. Schedule a viewing today. Owner financing is available.

919-921 Thomas St, Key West

$3,750,000

Charming Multifamily Compound in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional multifamily compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic districts, this property is just minutes away from famous landmarks, restaurants, and local shops. Take advantage of nearby beaches, water sports, and lush parks, offering a vibrant lifestyle for outdoor enthusiasts. This multifamily compound not only serves as a wonderful family home but also presents a lucrative rental opportunity in one of the most sought-after destinations in Florida. Don't miss your chance to own a piece of Key West history. Schedule a viewing today. Owner financing is available.

7 Beds ⋅ 8 Baths ⋅ 617140 MLS

Charming Multifamily Compound in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional multifamily compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic districts, this property is just minutes away from famous landmarks, restaurants, and local shops. Take advantage of nearby beaches, water sports, and lush parks, offering a vibrant lifestyle for outdoor enthusiasts. This multifamily compound not only serves as a wonderful family home but also presents a lucrative rental opportunity in one of the most sought-after destinations in Florida. Don't miss your chance to own a piece of Key West history. Schedule a viewing today. Owner financing is available.

919-921 Thomas St, Key West