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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

$4,300,000

**31 photos have been virtually staged and enhanced to assist buyers in visualizing design and decor options for this home.** Casa Sapodilla introduces itself with the kind of presence that feels both storied and serene. Built in 1996 and set at 13' elevation on Solares Hill, the residence pays homage to the architectural romance of Old Town's most celebrated homes.. broad verandas, intricate trim work, and Brazilian Cherry hardwood floors that recall a bygone era of island craftsmanship. Inside, the home unfolds in layers of refinement. Sunlit rooms connect gracefully to the outdoors through French doors and deep porches. The main house's split-level design elevates the primary suite with its own private staircase, while two additional bedrooms ascend another, creating a sense of calm seclusion. A separate pool suite, complete with private entrance, extends the home's versatility. The kitchen is anchored by a suite of premier appliances.. including a new SubZero refrigerator and a refurbished Viking gas range, and framed by custom cabinetry and built-ins. Recent upgrades such as the 2025 metal roof, updated HVAC systems, and a 24 kW Generac whole-house generator reflect meticulous stewardship. Outside, the grounds rise to the level of a private resort. Tropical gardens wind around stone pathways, illuminated at night by soft landscape lighting. A heated saltwater lagoon-style pool, resurfaced in 2025, curves around natural rock formations, a spa, and three cascading waterfalls. Every vista offers a moment of stillness.. from the shaded verandas to the courtyard designed for open-air dining. A one-car air-conditioned garage, currently serving as an art studio, and a two-car driveway complete the thoughtful layout. Just blocks from Duval Street and the Key West Historic Seaport, Casa Sapodilla is both connected and deeply private.. a luxury retreat rooted in island elegance.. Inquire within for details on the low insurance costs available for this home

4 Beds ⋅ 6 Baths ⋅ 617513 MLS

**31 photos have been virtually staged and enhanced to assist buyers in visualizing design and decor options for this home.** Casa Sapodilla introduces itself with the kind of presence that feels both storied and serene. Built in 1996 and set at 13' elevation on Solares Hill, the residence pays homage to the architectural romance of Old Town's most celebrated homes.. broad verandas, intricate trim work, and Brazilian Cherry hardwood floors that recall a bygone era of island craftsmanship. Inside, the home unfolds in layers of refinement. Sunlit rooms connect gracefully to the outdoors through French doors and deep porches. The main house's split-level design elevates the primary suite with its own private staircase, while two additional bedrooms ascend another, creating a sense of calm seclusion. A separate pool suite, complete with private entrance, extends the home's versatility. The kitchen is anchored by a suite of premier appliances.. including a new SubZero refrigerator and a refurbished Viking gas range, and framed by custom cabinetry and built-ins. Recent upgrades such as the 2025 metal roof, updated HVAC systems, and a 24 kW Generac whole-house generator reflect meticulous stewardship. Outside, the grounds rise to the level of a private resort. Tropical gardens wind around stone pathways, illuminated at night by soft landscape lighting. A heated saltwater lagoon-style pool, resurfaced in 2025, curves around natural rock formations, a spa, and three cascading waterfalls. Every vista offers a moment of stillness.. from the shaded verandas to the courtyard designed for open-air dining. A one-car air-conditioned garage, currently serving as an art studio, and a two-car driveway complete the thoughtful layout. Just blocks from Duval Street and the Key West Historic Seaport, Casa Sapodilla is both connected and deeply private.. a luxury retreat rooted in island elegance.. Inquire within for details on the low insurance costs available for this home

600 Elizabeth St, Key West

$3,375,000

Buy a Bar & Liquor Store in Key West! Dons' Place is the opportunity to purchase an Iconic and Landmark Indoor and Outdoor Bar & a Liquor Store with a Drive Through! This package is rarely available in Key West or anywhere in the Keys. Big bonus is that is includes a very valuable, full, unrestricted & transferrable 5-COP Liquor License that includes Tobacco & Retail Beverage with no food requirement! BEV 5400161. Monroe County Liquor Licenses are valued well over $1 Million and 2025 County Appraised Value of the two real estate parcels is over $2.7Million. Total Asset value alone is over $3.8 Million, not including business value. Two parcels of land total 11,836 sf. at corner of Truman & Grinnell Streets. The Indoor Bar and adjoining Liquor Store are in the main corner, CBS 2,396 sf. building along with men's and women's restrooms, office & storage. The building also operates maybe the only drive through, pick up window for Beer, Wine and Liquor left in the Keys! Several major repairs include new AC unit, new Bar, all new water lines and plumbing upgrades. New roof in 2022. There is an existing backup propane Generac Generator with automatic transfer not working. All Furniture, Fixtures and Equipment included. Outside is another 1,588 sf. covered outdoor Bar for entertaining, weddings, special events and parties. There is bar and table seating and a separate small office/storage building. The Bar and Liquor store are popular with both tourists and locals. The business is family managed with absentee owners and a few long time employees. Current Bar hours are 7am until 4am, 7 days per week. The Bar and Liquor Store are a money making operation with so many opportunities for growth for a new owner. Currently there is no food service on site, only pre-packaged snacks sold, but HNC -1 Zoning allows many commercial and residential uses & likely Food Trucks for added income. Same absentee owners since 1998 and first time listed for sale.

2 Baths ⋅ 614149 MLS

Buy a Bar & Liquor Store in Key West! Dons' Place is the opportunity to purchase an Iconic and Landmark Indoor and Outdoor Bar & a Liquor Store with a Drive Through! This package is rarely available in Key West or anywhere in the Keys. Big bonus is that is includes a very valuable, full, unrestricted & transferrable 5-COP Liquor License that includes Tobacco & Retail Beverage with no food requirement! BEV 5400161. Monroe County Liquor Licenses are valued well over $1 Million and 2025 County Appraised Value of the two real estate parcels is over $2.7Million. Total Asset value alone is over $3.8 Million, not including business value. Two parcels of land total 11,836 sf. at corner of Truman & Grinnell Streets. The Indoor Bar and adjoining Liquor Store are in the main corner, CBS 2,396 sf. building along with men's and women's restrooms, office & storage. The building also operates maybe the only drive through, pick up window for Beer, Wine and Liquor left in the Keys! Several major repairs include new AC unit, new Bar, all new water lines and plumbing upgrades. New roof in 2022. There is an existing backup propane Generac Generator with automatic transfer not working. All Furniture, Fixtures and Equipment included. Outside is another 1,588 sf. covered outdoor Bar for entertaining, weddings, special events and parties. There is bar and table seating and a separate small office/storage building. The Bar and Liquor store are popular with both tourists and locals. The business is family managed with absentee owners and a few long time employees. Current Bar hours are 7am until 4am, 7 days per week. The Bar and Liquor Store are a money making operation with so many opportunities for growth for a new owner. Currently there is no food service on site, only pre-packaged snacks sold, but HNC -1 Zoning allows many commercial and residential uses & likely Food Trucks for added income. Same absentee owners since 1998 and first time listed for sale.

1000-1006 Truman Ave, Key West

$2,895,000

Built in 2008, this expansive 3,220 sq ft residence sits on a nearly 5,000 sq ft lot and offers the perfect blend of comfort, style, and location. Centrally situated, you're just moments from beautiful beaches, top-tier dining, vibrant bars, museums, and all the attractions the area has to offer.Upstairs features three generously sized bedrooms, each with its own en suite bathroom and walk-in closet, providing privacy and convenience for family and guests alike. The main level is designed for living and entertaining, large open floor plan. An additional bedroom and bath on main floor with a door to the pool/deck area. The chef's kitchen is a standout, equipped with high-end stainless steel appliances including a 48-inch Viking gas range, refrigerator, ice maker, dishwasher, built-in steamer, wine cooler, and rich cherry cabinetry. Additional highlights include: Efficient 2-zone HVAC system, Impact windows and sliding glass doors, Beautiful Tigerwood flooring throughout. The exterior is equally impressive, featuring durable Hardi plank siding for low maintenance, Ipe wood decking, and a private pool surrounded by lush tropical landscaping. The fully fenced yard creates a serene and secluded outdoor retreat. The house also offers two off-street parking spaces, plus ample street parking for guests. A rare opportunity to own a spacious, well-appointed home in a prime location--this one truly has it all.

4 Beds ⋅ 5 Baths ⋅ 619665 MLS

Built in 2008, this expansive 3,220 sq ft residence sits on a nearly 5,000 sq ft lot and offers the perfect blend of comfort, style, and location. Centrally situated, you're just moments from beautiful beaches, top-tier dining, vibrant bars, museums, and all the attractions the area has to offer.Upstairs features three generously sized bedrooms, each with its own en suite bathroom and walk-in closet, providing privacy and convenience for family and guests alike. The main level is designed for living and entertaining, large open floor plan. An additional bedroom and bath on main floor with a door to the pool/deck area. The chef's kitchen is a standout, equipped with high-end stainless steel appliances including a 48-inch Viking gas range, refrigerator, ice maker, dishwasher, built-in steamer, wine cooler, and rich cherry cabinetry. Additional highlights include: Efficient 2-zone HVAC system, Impact windows and sliding glass doors, Beautiful Tigerwood flooring throughout. The exterior is equally impressive, featuring durable Hardi plank siding for low maintenance, Ipe wood decking, and a private pool surrounded by lush tropical landscaping. The fully fenced yard creates a serene and secluded outdoor retreat. The house also offers two off-street parking spaces, plus ample street parking for guests. A rare opportunity to own a spacious, well-appointed home in a prime location--this one truly has it all.

1320 South Street, Key West

$2,699,000

Real Estate offering only, business and liquor license not included. Prime corner location with great visibility on Truman Ave. HNC -1 Zoning allows many Commercial Uses including Transient Residential, Hotels, Multi Family Residential, Single Family Residential, Business & Professional Offices, Parking Lots, Medical Services, Food Trucks and more. Restaurants are a Conditional use. There are Two parcels of real estate, 1000 and 1006 Truman Ave. total of 104.75' on Truman Ave and 113' Deep. 2025 County Appraised Values of the two real estate parcels is over $2.7 Million! The existing corner CBS building is 2,396 sf. with indoor bar, men's and women's restrooms, office & storage, plus drive through liquor store. The existing drive through may be grandfathered for another potential use. The current Bar business may also be considered grandfathered. Several major repairs include new AC unit, new Bar, all new water lines and plumbing upgrades. New roof to the corner building in 2022. There is an additional 1,588 sf. of covered outdoor Bar with outdoor entertainment area. Same absentee owners since 1998 and first time listed for sale without the business or liquor license.

2 Baths ⋅ 617611 MLS

Real Estate offering only, business and liquor license not included. Prime corner location with great visibility on Truman Ave. HNC -1 Zoning allows many Commercial Uses including Transient Residential, Hotels, Multi Family Residential, Single Family Residential, Business & Professional Offices, Parking Lots, Medical Services, Food Trucks and more. Restaurants are a Conditional use. There are Two parcels of real estate, 1000 and 1006 Truman Ave. total of 104.75' on Truman Ave and 113' Deep. 2025 County Appraised Values of the two real estate parcels is over $2.7 Million! The existing corner CBS building is 2,396 sf. with indoor bar, men's and women's restrooms, office & storage, plus drive through liquor store. The existing drive through may be grandfathered for another potential use. The current Bar business may also be considered grandfathered. Several major repairs include new AC unit, new Bar, all new water lines and plumbing upgrades. New roof to the corner building in 2022. There is an additional 1,588 sf. of covered outdoor Bar with outdoor entertainment area. Same absentee owners since 1998 and first time listed for sale without the business or liquor license.

1000 Truman Ave, Key West

$2,550,000

Welcome to 1202 Royal Street, a beautifully reimagined and rebuilt Key West residence where thoughtful design, modern construction, and exceptional Old Town location come together. Featuring four (4) bedrooms and three-and-a-half (3.5) bathrooms, this property has been rebuilt from the ground up with meticulous attention to detail. Located in coveted Historic Old Town and the highly desirable X Flood Zone, 1202 Royal Street places you in the heart of everything that makes Key West special. Step through the stunning mahogany hurricane-impact front door into a bright interior with soaring ceilings, natural light, and a striking floating staircase leading to the second floor. The home flows effortlessly into an expansive open-concept kitchen and living area designed for both everyday living and entertaining. Open the home to your private backyard, where IPE decking, a heated and chilled pool, and separate hot tub create the perfect indoor/outdoor lifestyle and an ideal setting for entertaining family and friends. The ground-floor primary suite offers privacy from the rest of the home and features a beautiful ensuite bath. Upstairs, two additional bedrooms share a thoughtfully designed Jack-and-Jill bathroom, providing comfortable accommodations for family and guests. The detached guest house, configured as a legal duplex with separate water and electric meters, adds tremendous versatility. Use it as a luxurious pool house, private guest quarters, additional primary suite, or completely separate living space. Additional features include impact windows and doors, spray-foam insulation, IPE decking, two A/C zones in the main residence, ductless climate control in the guest house, fire sprinkler systems in both residences, and numerous additional upgrades throughout. Come experience 1202 Royal Street and discover what it means to live like royalty in Key West!

4 Beds ⋅ 4 Baths ⋅ 620994 MLS

Welcome to 1202 Royal Street, a beautifully reimagined and rebuilt Key West residence where thoughtful design, modern construction, and exceptional Old Town location come together. Featuring four (4) bedrooms and three-and-a-half (3.5) bathrooms, this property has been rebuilt from the ground up with meticulous attention to detail. Located in coveted Historic Old Town and the highly desirable X Flood Zone, 1202 Royal Street places you in the heart of everything that makes Key West special. Step through the stunning mahogany hurricane-impact front door into a bright interior with soaring ceilings, natural light, and a striking floating staircase leading to the second floor. The home flows effortlessly into an expansive open-concept kitchen and living area designed for both everyday living and entertaining. Open the home to your private backyard, where IPE decking, a heated and chilled pool, and separate hot tub create the perfect indoor/outdoor lifestyle and an ideal setting for entertaining family and friends. The ground-floor primary suite offers privacy from the rest of the home and features a beautiful ensuite bath. Upstairs, two additional bedrooms share a thoughtfully designed Jack-and-Jill bathroom, providing comfortable accommodations for family and guests. The detached guest house, configured as a legal duplex with separate water and electric meters, adds tremendous versatility. Use it as a luxurious pool house, private guest quarters, additional primary suite, or completely separate living space. Additional features include impact windows and doors, spray-foam insulation, IPE decking, two A/C zones in the main residence, ductless climate control in the guest house, fire sprinkler systems in both residences, and numerous additional upgrades throughout. Come experience 1202 Royal Street and discover what it means to live like royalty in Key West!

1202 Royal St, Key West

$2,550,000

Step into a residence that has captured the national spotlight. Recently honored as a Wall Street Journal ''House of the Week,'' 1017 Angela Street is a 118-year-old Old Town cottage masterfully reimagined for the modern connoisseur. Tucked away on a tranquil lane, yet moments from the Historic Seaport and Duval Street, this three bedroom, three and a half bath home is the ultimate blend of calm island style and sophisticated Key West living. From the quintessential front porch to the vibrant, playful interiors, every inch of this home radiates personality. The heart of the residence features rare, historic Dade County Pine walls and floors bathed in natural light, creating a warm, textured backdrop for the home's contemporary finishes. The thoughtfully designed L-shaped layout effortlessly connects the chef's kitchen-complete with granite countertops and stainless appliances-to the bar and living areas. This social heart of the home seamlessly merges with an expansive dining area, where impact-rated French doors invite the island breeze, creating a natural environment for entertaining. The floor plan includes a coveted first-floor primary suite for ultimate convenience. The home's artistic soul is further defined by a series of custom murals by artist Haley Leeper, most notably the hand-painted staircase, which creates an artistic transition to the second floor. Upstairs features a second primary bedroom with a spa-inspired bath and an intimate reading nook and an additional guest suite. The backyard is a secluded oasis, boasting a heated pool and spa with an upgraded system, outdoor shower, and Trex decking. Framed by lush tropical foliage and a magnificent, mature mango tree, this space offers a level of privacy and shade. Complete with off-street parking and a distinguished track record as a top-performing monthly rental, 1017 Angela Street is a ''turnkey'' treasure that perfectly balances historic architectural significance with lucrative investment potenti

3 Beds ⋅ 4 Baths ⋅ 619579 MLS

Step into a residence that has captured the national spotlight. Recently honored as a Wall Street Journal ''House of the Week,'' 1017 Angela Street is a 118-year-old Old Town cottage masterfully reimagined for the modern connoisseur. Tucked away on a tranquil lane, yet moments from the Historic Seaport and Duval Street, this three bedroom, three and a half bath home is the ultimate blend of calm island style and sophisticated Key West living. From the quintessential front porch to the vibrant, playful interiors, every inch of this home radiates personality. The heart of the residence features rare, historic Dade County Pine walls and floors bathed in natural light, creating a warm, textured backdrop for the home's contemporary finishes. The thoughtfully designed L-shaped layout effortlessly connects the chef's kitchen-complete with granite countertops and stainless appliances-to the bar and living areas. This social heart of the home seamlessly merges with an expansive dining area, where impact-rated French doors invite the island breeze, creating a natural environment for entertaining. The floor plan includes a coveted first-floor primary suite for ultimate convenience. The home's artistic soul is further defined by a series of custom murals by artist Haley Leeper, most notably the hand-painted staircase, which creates an artistic transition to the second floor. Upstairs features a second primary bedroom with a spa-inspired bath and an intimate reading nook and an additional guest suite. The backyard is a secluded oasis, boasting a heated pool and spa with an upgraded system, outdoor shower, and Trex decking. Framed by lush tropical foliage and a magnificent, mature mango tree, this space offers a level of privacy and shade. Complete with off-street parking and a distinguished track record as a top-performing monthly rental, 1017 Angela Street is a ''turnkey'' treasure that perfectly balances historic architectural significance with lucrative investment potenti

1017 Angela St, Key West

$2,500,000

Completely remodeled from top to bottom, this turnkey restaurant in the heart of Old Town Key West offers a rare opportunity to own a fully updated and licensed 150-seat dining destination. Every inch of the property has been thoughtfully renovated, including brand-new electrical, plumbing, HVAC, flooring, lighting, and fixtures, creating a fresh, modern space that still captures the charm and character of historic Key West. The layout features expansive indoor-outdoor dining areas, a stylish full-service bar, and newly designed restrooms, all tailored for comfort, ambiance, and efficient flow. The commercial-grade kitchen is fully equipped with state-of-the-art appliances, ample prep space, and storage, making it ideal for high-volume service across a wide range of culinary concepts. Adding to its versatility, the property also includes a beautifully updated 1-bedroom, 1-bathroom apartment upstairs—perfect for on-site living, staff housing, or additional rental income.

1 Beds ⋅ 3 Baths ⋅ 615015 MLS

Completely remodeled from top to bottom, this turnkey restaurant in the heart of Old Town Key West offers a rare opportunity to own a fully updated and licensed 150-seat dining destination. Every inch of the property has been thoughtfully renovated, including brand-new electrical, plumbing, HVAC, flooring, lighting, and fixtures, creating a fresh, modern space that still captures the charm and character of historic Key West. The layout features expansive indoor-outdoor dining areas, a stylish full-service bar, and newly designed restrooms, all tailored for comfort, ambiance, and efficient flow. The commercial-grade kitchen is fully equipped with state-of-the-art appliances, ample prep space, and storage, making it ideal for high-volume service across a wide range of culinary concepts. Adding to its versatility, the property also includes a beautifully updated 1-bedroom, 1-bathroom apartment upstairs—perfect for on-site living, staff housing, or additional rental income.

532 Margaret St, Key West

$2,400,000

Welcome to your waterfront escape in Key West. Located within a gated community, Gulfview Pointe offers the perfect blend of island charm, comfort, and an exceptional waterfront lifestyle and just minutes from world-famous Duval Street and all that Key West has to offer. This move-in-ready 3-bedroom, 2.5-bath home welcomes you with classic Key West architecture, lush tropical surroundings, and inviting indoor and outdoor living spaces. The kitchen features granite countertops, stainless steel appliances, and ample cabinetry. Step outside to your own private tropical retreat, where a sparkling pool surrounded by composite decking creates the perfect setting for relaxing, entertaining, and enjoying the year-round Florida Keys sunshine. Beyond the pool, your private dock opens the door to endless adventures. Spend the afternoon fishing, set out on your personal watercraft, paddleboard or kayak, or simply unwind and watch another spectacular Key West sunset from your own backyard. A covered carport and the privacy of a gated community complete this island home. Whether you're searching for a full-time residence, your own Key West getaway, or investment opportunity with luxury vacation rental potential in this highly sought-after community, Gulfview Pointe offers an exceptional opportunity. Opportunities like this don't come around often--invest in your dream home and start living the Key West waterfront lifestyle you've been dreaming of. Call today to schedule your private showing!

3 Beds ⋅ 3 Baths ⋅ 621218 MLS

Welcome to your waterfront escape in Key West. Located within a gated community, Gulfview Pointe offers the perfect blend of island charm, comfort, and an exceptional waterfront lifestyle and just minutes from world-famous Duval Street and all that Key West has to offer. This move-in-ready 3-bedroom, 2.5-bath home welcomes you with classic Key West architecture, lush tropical surroundings, and inviting indoor and outdoor living spaces. The kitchen features granite countertops, stainless steel appliances, and ample cabinetry. Step outside to your own private tropical retreat, where a sparkling pool surrounded by composite decking creates the perfect setting for relaxing, entertaining, and enjoying the year-round Florida Keys sunshine. Beyond the pool, your private dock opens the door to endless adventures. Spend the afternoon fishing, set out on your personal watercraft, paddleboard or kayak, or simply unwind and watch another spectacular Key West sunset from your own backyard. A covered carport and the privacy of a gated community complete this island home. Whether you're searching for a full-time residence, your own Key West getaway, or investment opportunity with luxury vacation rental potential in this highly sought-after community, Gulfview Pointe offers an exceptional opportunity. Opportunities like this don't come around often--invest in your dream home and start living the Key West waterfront lifestyle you've been dreaming of. Call today to schedule your private showing!

2623 Gulfview Dr, Key West

$2,350,000

Set within the exclusive enclave of The Sanctuary at Key West Golf Club, this rare offering presents two distinct residences united as one extraordinary parcel -- a configuration unlike anything currently available on the Key West market. Verandas and porches wrap the property, framing sweeping views of the lake and the emerald fairways of the 17th hole, while tiled floors flow throughout both residences, blurring the line between the two homes and the tropical air outside. At the heart of it all, a resort-caliber pool measuring an impressive 12 x 30 feet anchors a 1,500 square foot outdoor terrace, where long tables are set for twelve or more, indoors and out, beneath the Key West sky. With 6 bedrooms and 5.5 bathrooms spread across 2,840 square feet, this dual-residence estate is purpose-built for the multigenerational family, offering the rare gift of togetherness paired with independence -- separate structures for separate households, united by a single spectacular pool deck built for gathering. For the discerning second-home buyer or investor, the dual-dwelling design opens the door to flexible living arrangements or income-generating potential, a configuration increasingly coveted in today's Key West market. This is more than a home -- it is a once-in-a-lifetime opportunity to establish a family legacy on one of Key West's most coveted golf course settings. Here, generations will gather beneath the verandas, celebrate over long tables set for twelve, and watch the sun set over the 17th green. This is Key West living, reimagined for the modern family -- and passed down for generations to come.

6 Beds ⋅ 6 Baths ⋅ 620852 MLS

Set within the exclusive enclave of The Sanctuary at Key West Golf Club, this rare offering presents two distinct residences united as one extraordinary parcel -- a configuration unlike anything currently available on the Key West market. Verandas and porches wrap the property, framing sweeping views of the lake and the emerald fairways of the 17th hole, while tiled floors flow throughout both residences, blurring the line between the two homes and the tropical air outside. At the heart of it all, a resort-caliber pool measuring an impressive 12 x 30 feet anchors a 1,500 square foot outdoor terrace, where long tables are set for twelve or more, indoors and out, beneath the Key West sky. With 6 bedrooms and 5.5 bathrooms spread across 2,840 square feet, this dual-residence estate is purpose-built for the multigenerational family, offering the rare gift of togetherness paired with independence -- separate structures for separate households, united by a single spectacular pool deck built for gathering. For the discerning second-home buyer or investor, the dual-dwelling design opens the door to flexible living arrangements or income-generating potential, a configuration increasingly coveted in today's Key West market. This is more than a home -- it is a once-in-a-lifetime opportunity to establish a family legacy on one of Key West's most coveted golf course settings. Here, generations will gather beneath the verandas, celebrate over long tables set for twelve, and watch the sun set over the 17th green. This is Key West living, reimagined for the modern family -- and passed down for generations to come.

287 & 289 Golf Club Dr, Key West

$2,250,000

Prime Multi Unit property in Old Town. Six legal apartments with 6 off street parking spaces is rarely available. There is a total of 10 bedrooms and 6 baths, divided into Three 1bd/1ba units, Two 2 bd/1ba units and one 3bd/1ba unit. Two story CBS & Frame building has total of 3,876 sf. Building sits on good size 3,598 sf. lot that runs from Pohalski St. to Havana Lane giving each tenant easy access to their apartment and off street parking spot. Each apartment has it's own separate Electric and Water meter. Lot sits in a BFE flood zone, former X flood zone, and is high and dry. Gross rents total $14,500 per month with limited expenses. Property has been in the family for generations and ready to pass on to a new owner. Perfect for a long term investor, 1031 Exchange Replacement Property or Employee Housing!

10 Beds ⋅ 6 Baths ⋅ 620102 MLS

Prime Multi Unit property in Old Town. Six legal apartments with 6 off street parking spaces is rarely available. There is a total of 10 bedrooms and 6 baths, divided into Three 1bd/1ba units, Two 2 bd/1ba units and one 3bd/1ba unit. Two story CBS & Frame building has total of 3,876 sf. Building sits on good size 3,598 sf. lot that runs from Pohalski St. to Havana Lane giving each tenant easy access to their apartment and off street parking spot. Each apartment has it's own separate Electric and Water meter. Lot sits in a BFE flood zone, former X flood zone, and is high and dry. Gross rents total $14,500 per month with limited expenses. Property has been in the family for generations and ready to pass on to a new owner. Perfect for a long term investor, 1031 Exchange Replacement Property or Employee Housing!

912 Pohalski St, Key West

$2,250,000

Prime Multi Unit property in Old Town. Six legal apartments with 6 off street parking spaces is rarely available. There is a total of 10 bedrooms and 6 baths, divided into Three 1bd/1ba units, Two 2 bd/1ba units and one 3bd/1ba unit. Two story CBS & Frame building has total of 3,876 sf. Building sits on good size 3,598 sf. lot that runs from Pohalski St. to Havana Lane giving each tenant easy access to their apartment and off street parking spot. Each apartment has it's own separate Electric and Water meter. Lot sits in a BFE flood zone, former X flood zone, and is high and dry. Gross rents total $14,500 per month with limited expenses. Property has been in the family for generations and ready to pass on to a new owner. Perfect for a long term investor, 1031 Exchange Replacement Property or Employee Housing!

10 Beds ⋅ 6 Baths ⋅ 620101 MLS

Prime Multi Unit property in Old Town. Six legal apartments with 6 off street parking spaces is rarely available. There is a total of 10 bedrooms and 6 baths, divided into Three 1bd/1ba units, Two 2 bd/1ba units and one 3bd/1ba unit. Two story CBS & Frame building has total of 3,876 sf. Building sits on good size 3,598 sf. lot that runs from Pohalski St. to Havana Lane giving each tenant easy access to their apartment and off street parking spot. Each apartment has it's own separate Electric and Water meter. Lot sits in a BFE flood zone, former X flood zone, and is high and dry. Gross rents total $14,500 per month with limited expenses. Property has been in the family for generations and ready to pass on to a new owner. Perfect for a long term investor, 1031 Exchange Replacement Property or Employee Housing!

912 Pohalski St, Key West

$1,995,000

1202 Simonton Street sits in the heart of Old Town, South of Truman, four blocks from the Southernmost Point. This corner has been home to some of Key West's most recognized restaurants & the bones know what this building is capable of. If you're looking for a commercial building in Old Town Key West that offers: a 4,366-square-foot CBS building on a 4,700-square-foot corner lot, zoned Historic Neighborhood Commercial, on one of the island's most walkable and high-traffic corridors, delivered in shell condition and ready for a buyer who knows exactly what they want to build. Look no further.

619755 MLS

1202 Simonton Street sits in the heart of Old Town, South of Truman, four blocks from the Southernmost Point. This corner has been home to some of Key West's most recognized restaurants & the bones know what this building is capable of. If you're looking for a commercial building in Old Town Key West that offers: a 4,366-square-foot CBS building on a 4,700-square-foot corner lot, zoned Historic Neighborhood Commercial, on one of the island's most walkable and high-traffic corridors, delivered in shell condition and ready for a buyer who knows exactly what they want to build. Look no further.

1202 Simonton St, Key West

$1,899,000

Some homes invite you in, and others make you want to stay. 1220 Georgia Street does both. Tucked into a quiet pocket of Old Town on a corner lot, the home feels peaceful and removed, yet everything you need is just moments away. A short walk takes you to neighborhood cafes, the beach, or a quick bike ride into the heart of town, while at home, the pace feels slower and more relaxed. The approach sets the tone. A marble and Coralina pathway leads through lush landscaping to a welcoming front porch and a striking antique front door that hints at the character inside. Step through and the space opens up with high ceilings and large windows that fill the home with natural light. The living areas flow easily together and draw you toward the outdoors, where a private backyard retreat awaits. Surrounded by mature tropical foliage, the cocktail pool and IPE deck create a setting that feels both secluded and inviting, perfect for entertaining or unwinding. The main house offers 3 bedrooms and 2 bathrooms, complemented by a separate 1 bedroom and 1 bathroom guest cottage that provides flexibility for visitors or a quiet escape. This is a home that feels well cared for, loved, and ready for its next chapter. A place where the details matter, but the feeling matters even more.

4 Beds ⋅ 3 Baths ⋅ 619619 MLS

Some homes invite you in, and others make you want to stay. 1220 Georgia Street does both. Tucked into a quiet pocket of Old Town on a corner lot, the home feels peaceful and removed, yet everything you need is just moments away. A short walk takes you to neighborhood cafes, the beach, or a quick bike ride into the heart of town, while at home, the pace feels slower and more relaxed. The approach sets the tone. A marble and Coralina pathway leads through lush landscaping to a welcoming front porch and a striking antique front door that hints at the character inside. Step through and the space opens up with high ceilings and large windows that fill the home with natural light. The living areas flow easily together and draw you toward the outdoors, where a private backyard retreat awaits. Surrounded by mature tropical foliage, the cocktail pool and IPE deck create a setting that feels both secluded and inviting, perfect for entertaining or unwinding. The main house offers 3 bedrooms and 2 bathrooms, complemented by a separate 1 bedroom and 1 bathroom guest cottage that provides flexibility for visitors or a quiet escape. This is a home that feels well cared for, loved, and ready for its next chapter. A place where the details matter, but the feeling matters even more.

1220 Georgia 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

$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

$1,675,000

Welcome to 606 Grinnell Street located in the heart of Old Town Key West, this charming duplex offers the perfect blend of classic Key West character and flexible living opportunities. The first-floor unit features 2 nice sized bedrooms and 1.5 baths, while the spacious second-floor unit offers 3 bedrooms and 1 bath, complete with a private rear balcony overlooking the backyard oasis. Both units feature full sized kitchens with great dining spaces, as well as living rooms too. A welcoming front porch adds to the home's island charm, creating the perfect spot to relax and enjoy the neighborhood atmosphere. Step outside to your private backyard retreat featuring a sparkling pool for your relaxation, ideal for entertaining, time off, or enjoying the Key West lifestyle year-round. Whether you're looking for an investment property, multi-generational living, or the option to live in one unit while renting the other, this versatile Old Town property offers endless potential. There's a convenient side door entrance for the 2nd unit upstairs, while having a lockout door in the first unit if you wanted access to upstairs. Nice thought for Indoor or Outdoor Access to upstairs. Just moments from world-famous Duval Street with lots of dining options, historical seaport, shopping, and nightlife experiences.

5 Beds ⋅ 3 Baths ⋅ 619947 MLS

Welcome to 606 Grinnell Street located in the heart of Old Town Key West, this charming duplex offers the perfect blend of classic Key West character and flexible living opportunities. The first-floor unit features 2 nice sized bedrooms and 1.5 baths, while the spacious second-floor unit offers 3 bedrooms and 1 bath, complete with a private rear balcony overlooking the backyard oasis. Both units feature full sized kitchens with great dining spaces, as well as living rooms too. A welcoming front porch adds to the home's island charm, creating the perfect spot to relax and enjoy the neighborhood atmosphere. Step outside to your private backyard retreat featuring a sparkling pool for your relaxation, ideal for entertaining, time off, or enjoying the Key West lifestyle year-round. Whether you're looking for an investment property, multi-generational living, or the option to live in one unit while renting the other, this versatile Old Town property offers endless potential. There's a convenient side door entrance for the 2nd unit upstairs, while having a lockout door in the first unit if you wanted access to upstairs. Nice thought for Indoor or Outdoor Access to upstairs. Just moments from world-famous Duval Street with lots of dining options, historical seaport, shopping, and nightlife experiences.

606 Grinnell St, Key West

$1,499,000

Beautifully renovated corner-lot home in the heart of Casa Marina. This 2-bedroom, 2.5-bath residence sits on a 4,331 sq. ft. lot with room for a pool and offers a seamless blend of modern updates and classic Key West charm. Highlights include wide-plank wood floors, a bright all-white interior, and a designer kitchen featuring custom cabinetry, La Cornue gas range, paneled dishwasher, wine cooler, Quartz island, and subway-tile backsplash. The living room boasts built-in bookshelves and flows into a flexible study/home office. Multiple sets of French doors open to a covered front porch, outdoor dining area, and private wraparound porch. The primary suite offers custom wardrobes and a luxurious marble ensuite with soaking tub, glass-enclosed shower, and nickel fixtures. Guest bedroom with ensuite bath, dedicated laundry area, and stylish powder room complete the layout. Steps to Duval Street, Higgs Beach, Edward B. Knight Pier, waterfront dining, dog parks, and tennis/pickleball courts. A rare offering in one of Key West's most desirable neighborhoods.

2 Beds ⋅ 3 Baths ⋅ 620047 MLS

Beautifully renovated corner-lot home in the heart of Casa Marina. This 2-bedroom, 2.5-bath residence sits on a 4,331 sq. ft. lot with room for a pool and offers a seamless blend of modern updates and classic Key West charm. Highlights include wide-plank wood floors, a bright all-white interior, and a designer kitchen featuring custom cabinetry, La Cornue gas range, paneled dishwasher, wine cooler, Quartz island, and subway-tile backsplash. The living room boasts built-in bookshelves and flows into a flexible study/home office. Multiple sets of French doors open to a covered front porch, outdoor dining area, and private wraparound porch. The primary suite offers custom wardrobes and a luxurious marble ensuite with soaking tub, glass-enclosed shower, and nickel fixtures. Guest bedroom with ensuite bath, dedicated laundry area, and stylish powder room complete the layout. Steps to Duval Street, Higgs Beach, Edward B. Knight Pier, waterfront dining, dog parks, and tennis/pickleball courts. A rare offering in one of Key West's most desirable neighborhoods.

1401 Grinnell St, Key West

$1,200,000

Transient receiver site - Truly a diamond in the rough. Great location, behind the Hemingway House between Duval and Whitehead Street. Lot backs up to Whalton Lane (off Duval) with room for parking and a pool. Bring your contractor and a transient license to the property and she will truly shine like the Hope Diamond with happiness and prosperity. Buyers should do their own due diligence to determine transient license receivership requirements prior to making an offer. Probate is required.

3 Beds ⋅ 1 Baths ⋅ 617022 MLS

Transient receiver site - Truly a diamond in the rough. Great location, behind the Hemingway House between Duval and Whitehead Street. Lot backs up to Whalton Lane (off Duval) with room for parking and a pool. Bring your contractor and a transient license to the property and she will truly shine like the Hope Diamond with happiness and prosperity. Buyers should do their own due diligence to determine transient license receivership requirements prior to making an offer. Probate is required.

418 Olivia St, Key West

$1,175,000

This show-stopping luxury condo delivers a rare blend of historic charm with a fully renovated interior that was just completed a few years ago. The first level features an open living and dining plan with 10' ceilings, an abundance of natural light, restored Dade County Pine accent walls, plantation shutters, modern lighting, and tile flooring throughout. The kitchen was built to impress and features a large quartz island, Cafe Collection appliances, a gas range, designer tile backsplash, and a separate coffee and cocktail bar. Practical touches include an entry way storage closet, built-in closet systems, and a full-size GE washer and dryer tucked neatly under the stairs. The upstairs primary suite feels like a private retreat.. it features a sitting area with double French doors that open to the balcony perch where you'll enjoy views of beautiful sunsets through the treetops. The en suite bath is finished with gorgeous Onyx Style slab tile, a double vanity, designer fixtures and a glass shower with statement detailing. This luxury condo is offered fully furnished and turnkey, with local Key West history woven throughout. 30-day rentals are allowed with restrictions, it's in the X Flood Zone, and from here it's always an easy stroll to Fort Zach Beach, Truman Waterfront Park, and the Duval Street corridor for fine dining, shopping, and live entertainment, capturing the ease and energy of Key West living..

2 Beds ⋅ 2 Baths ⋅ 618511 MLS

This show-stopping luxury condo delivers a rare blend of historic charm with a fully renovated interior that was just completed a few years ago. The first level features an open living and dining plan with 10' ceilings, an abundance of natural light, restored Dade County Pine accent walls, plantation shutters, modern lighting, and tile flooring throughout. The kitchen was built to impress and features a large quartz island, Cafe Collection appliances, a gas range, designer tile backsplash, and a separate coffee and cocktail bar. Practical touches include an entry way storage closet, built-in closet systems, and a full-size GE washer and dryer tucked neatly under the stairs. The upstairs primary suite feels like a private retreat.. it features a sitting area with double French doors that open to the balcony perch where you'll enjoy views of beautiful sunsets through the treetops. The en suite bath is finished with gorgeous Onyx Style slab tile, a double vanity, designer fixtures and a glass shower with statement detailing. This luxury condo is offered fully furnished and turnkey, with local Key West history woven throughout. 30-day rentals are allowed with restrictions, it's in the X Flood Zone, and from here it's always an easy stroll to Fort Zach Beach, Truman Waterfront Park, and the Duval Street corridor for fine dining, shopping, and live entertainment, capturing the ease and energy of Key West living..

927 Thomas St Unit #2, Key West

$1,175,000

Elegant, peaceful and turn-key, this light-filled, Old Town condo is just one block to Duval Street! This home shines with 23 windows on two levels and relaxes with its easy, breezy, tropical vibe, landscaped grounds and pool. Turn-key, renovated and furnished, this condo resides in the historic Campbell Building on Fleming Street, one of Old Town's most coveted. Enjoy a gorgeous interior with pine floors throughout, new ac mini splits in every room, plentiful storage and a spacious, modern kitchen. The hefty project of converting all 23 windows to impact glass has been done for you, ensuring superior wind protection, an extremely quiet inside space and low energy costs. This unit exudes charm and easy living and feels like a true home all with immediate access to the best of Key West. In a moment you can be dining at your favorite restaurant, watching the sunset at Mallory, listening to live music or hitting Fausto's market for those last minute grocery items. And you will love the balcony where you can take in the hustle and bustle of passer-byers from above, laze away the morning while sipping on your Cuban Coffee, enjoy cocktails under the stars or watch the Fantasy Fest Local's Parade from the best seat in the house! Unit 4 has been fully renovated and needs nothing but you! A custom designed kitchen with ample storage, stainless steel appliances, quartz counters and a white Kohler, porcelain farmer's sink overlooking Fleming below make cooking and entertaining a breeze and a joy. Only 9 units reside in the Campbell Building, all nestled on a beautifully landscaped compound with a large pool. This is a great place to live and will also make for a lucrative vacation rental. Enjoy living on Millionaire's Row with access to all that makes Key West the best place to live the island lifestyle.

2 Beds ⋅ 2 Baths ⋅ 618827 MLS

Elegant, peaceful and turn-key, this light-filled, Old Town condo is just one block to Duval Street! This home shines with 23 windows on two levels and relaxes with its easy, breezy, tropical vibe, landscaped grounds and pool. Turn-key, renovated and furnished, this condo resides in the historic Campbell Building on Fleming Street, one of Old Town's most coveted. Enjoy a gorgeous interior with pine floors throughout, new ac mini splits in every room, plentiful storage and a spacious, modern kitchen. The hefty project of converting all 23 windows to impact glass has been done for you, ensuring superior wind protection, an extremely quiet inside space and low energy costs. This unit exudes charm and easy living and feels like a true home all with immediate access to the best of Key West. In a moment you can be dining at your favorite restaurant, watching the sunset at Mallory, listening to live music or hitting Fausto's market for those last minute grocery items. And you will love the balcony where you can take in the hustle and bustle of passer-byers from above, laze away the morning while sipping on your Cuban Coffee, enjoy cocktails under the stars or watch the Fantasy Fest Local's Parade from the best seat in the house! Unit 4 has been fully renovated and needs nothing but you! A custom designed kitchen with ample storage, stainless steel appliances, quartz counters and a white Kohler, porcelain farmer's sink overlooking Fleming below make cooking and entertaining a breeze and a joy. Only 9 units reside in the Campbell Building, all nestled on a beautifully landscaped compound with a large pool. This is a great place to live and will also make for a lucrative vacation rental. Enjoy living on Millionaire's Row with access to all that makes Key West the best place to live the island lifestyle.

617 Fleming St Unit APT 4, Key West

$1,150,000

Tucked away on a quiet lane in Old Town Key West, this historic island home offers a rare combination of architectural character, elevated location, and walkable convenience. Positioned in the desirable X-flood zone near the highest natural elevation on the island, the property sits just steps from the energy of Duval Street while maintaining a peaceful residential feel. Originally constructed during the Henry Flagler railroad era, the home has been thoughtfully updated while preserving the warmth and authenticity that make Key West architecture so iconic. Inside, rich Dade County pine walls, hardwood flooring, and tall ceilings create an inviting atmosphere filled with natural texture and timeless charm. Impact windows and curated high-end finishes blend seamlessly with the home's historic roots. The kitchen was designed with both style and function in mind, featuring dade county pine countertops and a collection of premium appliances including a Sub-Zero refrigerator and Big Chill gas range. Flexible living areas allow the home to function as either a spacious two-bedroom retreat or a three-bedroom layout depending on your needs. Outdoor living is equally special. A lush backyard filled with mature tropical landscaping and fruit trees creates a private island setting that feels worlds away from the bustle of town, with space to potentially add a pool in the future. The welcoming front porch serves as a timeless gathering space, perfectly suited for morning coffee, evening cocktails, and enjoying the laid-back rhythm of Old Town living. Just a short stroll from Truman Waterfront Park, Fort Zachary Taylor Beach, galleries, restaurants, and marinas, this property captures the essence of classic Old Town living -- historic, relaxed, and unmistakably Key West.

2 Beds ⋅ 2 Baths ⋅ 620012 MLS

Tucked away on a quiet lane in Old Town Key West, this historic island home offers a rare combination of architectural character, elevated location, and walkable convenience. Positioned in the desirable X-flood zone near the highest natural elevation on the island, the property sits just steps from the energy of Duval Street while maintaining a peaceful residential feel. Originally constructed during the Henry Flagler railroad era, the home has been thoughtfully updated while preserving the warmth and authenticity that make Key West architecture so iconic. Inside, rich Dade County pine walls, hardwood flooring, and tall ceilings create an inviting atmosphere filled with natural texture and timeless charm. Impact windows and curated high-end finishes blend seamlessly with the home's historic roots. The kitchen was designed with both style and function in mind, featuring dade county pine countertops and a collection of premium appliances including a Sub-Zero refrigerator and Big Chill gas range. Flexible living areas allow the home to function as either a spacious two-bedroom retreat or a three-bedroom layout depending on your needs. Outdoor living is equally special. A lush backyard filled with mature tropical landscaping and fruit trees creates a private island setting that feels worlds away from the bustle of town, with space to potentially add a pool in the future. The welcoming front porch serves as a timeless gathering space, perfectly suited for morning coffee, evening cocktails, and enjoying the laid-back rhythm of Old Town living. Just a short stroll from Truman Waterfront Park, Fort Zachary Taylor Beach, galleries, restaurants, and marinas, this property captures the essence of classic Old Town living -- historic, relaxed, and unmistakably Key West.

709 Chapman Ln, Key West

$1,060,000

At the end of wide, quiet cul-de-sac, life naturally slows, sunsets linger, 20 Kingfisher reveals itself as a private island retreat @ KW Golf Club. Inviting brick walkway, lush tropical landscaping, river rock, lead to freshly painted front steps, welcoming front veranda that set the tone, refined, thoughtfully cared for. This home feels loved the moment you arrive. Inside, warmth & craftsmanship take center stage. Rich heart pine flooring grounds the main level, continuing up the staircase. Elegant, functional fully remodeled kitchen features custom cottage-style wooden cabinetry, soft-close drawers, luxurious granite countertops, beautiful built-in storage beneath the breakfast bar. All upgraded stainless appliances complete the space: new dishwasher, radiant cooktop range w/double ovens/convection, microwave, French-door refrigerator/freezer, every detail chosen for beauty & performance. From the living area, the home opens to a captivating, expanded screened rear veranda overlooking the lake, the #2 tee box & S.W. sky that delivers breathtaking sunsets. When the Royal Poinciana bursts into bloom, its fiery canopy becomes a work of art, reflected in the water, glowing at dusk, unforgettable! Upstairs, the home transforms into a tranquil private retreat. High-end luxury vinyl plank flooring w/padded underlayment provides a cushioned ''walking on air'' feel, waterproof, elegant, designed for long-term comfort. 2 spacious en-suite bedrooms anchor the 2nd level, defined by cozy architectural charm w/gentle eaved rooflines, adding character & intimate cottage feel. The primary suite is inviting w/a generous double closet & large built-in storage. En-suite bath is a true showpiece, featuring new pendant lighting, fully tiled walk-in shower w/built-in bench, wrapped in vibrant royal blue/burgundy ceramic tile. Guest bdrm. is mirrored image w/lg. extended closet. 3rd bdrm. is office/study. Private heated resurfaced pool upgraded w/steps/railing is divine. So much more!

3 Beds ⋅ 3 Baths ⋅ 618186 MLS

At the end of wide, quiet cul-de-sac, life naturally slows, sunsets linger, 20 Kingfisher reveals itself as a private island retreat @ KW Golf Club. Inviting brick walkway, lush tropical landscaping, river rock, lead to freshly painted front steps, welcoming front veranda that set the tone, refined, thoughtfully cared for. This home feels loved the moment you arrive. Inside, warmth & craftsmanship take center stage. Rich heart pine flooring grounds the main level, continuing up the staircase. Elegant, functional fully remodeled kitchen features custom cottage-style wooden cabinetry, soft-close drawers, luxurious granite countertops, beautiful built-in storage beneath the breakfast bar. All upgraded stainless appliances complete the space: new dishwasher, radiant cooktop range w/double ovens/convection, microwave, French-door refrigerator/freezer, every detail chosen for beauty & performance. From the living area, the home opens to a captivating, expanded screened rear veranda overlooking the lake, the #2 tee box & S.W. sky that delivers breathtaking sunsets. When the Royal Poinciana bursts into bloom, its fiery canopy becomes a work of art, reflected in the water, glowing at dusk, unforgettable! Upstairs, the home transforms into a tranquil private retreat. High-end luxury vinyl plank flooring w/padded underlayment provides a cushioned ''walking on air'' feel, waterproof, elegant, designed for long-term comfort. 2 spacious en-suite bedrooms anchor the 2nd level, defined by cozy architectural charm w/gentle eaved rooflines, adding character & intimate cottage feel. The primary suite is inviting w/a generous double closet & large built-in storage. En-suite bath is a true showpiece, featuring new pendant lighting, fully tiled walk-in shower w/built-in bench, wrapped in vibrant royal blue/burgundy ceramic tile. Guest bdrm. is mirrored image w/lg. extended closet. 3rd bdrm. is office/study. Private heated resurfaced pool upgraded w/steps/railing is divine. So much more!

20 Kingfisher Ln, Key West

$1,025,000

This spacious two-bedroom, two-bath penthouse condo boasts a stunning balcony with ocean views, making it the perfect place to relax and enjoy the breathtaking scenery. The beautifully designed kitchen features a breakfast bar, granite countertops, and stainless steel appliances, making it a chef's dream come true. The stunning living room and dining room are flooded with natural light, creating a bright, inviting space perfect for entertaining guests. The floor-to-ceiling windows allow the natural light to pour in and are complemented by the soaring cathedral ceilings, which add an extra layer of grandeur and elegance to the space. Ample storage throughout ensures you'll have plenty of space to store all your belongings and keep your new home tidy and organized. The best feature of this penthouse is the breathtaking sunrises you'll enjoy over the Atlantic Ocean. Whether you're sipping your morning coffee or simply taking in the view, this condo will provide the perfect setting for relaxation and rejuvenation. The complex: One of the best parts of 1800 Atlantic is its private beach. You can soak up the sun, enjoy the stunning ocean views, or dip in the Olympic-sized heated pool while relaxing within this gated and secured oceanside community. For those who love staying active, three lighted tennis courts are perfect for a friendly game with friends or a competitive match, and the fitness center is fully equipped with everything you need to stay in shape and achieve your health goals. With storage and covered garage parking, you'll have plenty of space to keep all your belongings safe and secure. With its tropical resort-style setting and luxurious amenities, 1800 Atlantic is the perfect place to call home.

2 Beds ⋅ 2 Baths ⋅ 619778 MLS

This spacious two-bedroom, two-bath penthouse condo boasts a stunning balcony with ocean views, making it the perfect place to relax and enjoy the breathtaking scenery. The beautifully designed kitchen features a breakfast bar, granite countertops, and stainless steel appliances, making it a chef's dream come true. The stunning living room and dining room are flooded with natural light, creating a bright, inviting space perfect for entertaining guests. The floor-to-ceiling windows allow the natural light to pour in and are complemented by the soaring cathedral ceilings, which add an extra layer of grandeur and elegance to the space. Ample storage throughout ensures you'll have plenty of space to store all your belongings and keep your new home tidy and organized. The best feature of this penthouse is the breathtaking sunrises you'll enjoy over the Atlantic Ocean. Whether you're sipping your morning coffee or simply taking in the view, this condo will provide the perfect setting for relaxation and rejuvenation. The complex: One of the best parts of 1800 Atlantic is its private beach. You can soak up the sun, enjoy the stunning ocean views, or dip in the Olympic-sized heated pool while relaxing within this gated and secured oceanside community. For those who love staying active, three lighted tennis courts are perfect for a friendly game with friends or a competitive match, and the fitness center is fully equipped with everything you need to stay in shape and achieve your health goals. With storage and covered garage parking, you'll have plenty of space to keep all your belongings safe and secure. With its tropical resort-style setting and luxurious amenities, 1800 Atlantic is the perfect place to call home.

1800 Atlantic Blvd Unit 427C, 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

$875,000

Stylish ''Spa'' home within the enclave of The Sanctuary of the Key West Golf Club. An open floor plan greets you to this light filled home that overlooks a private backyard oasis with dip pool, covered brick patio and maintenance free yard. Thoughtful kitchen updates including sleek quartz countertops with waterfall edge, stainless appliance package and new island lighting. The upstairs enjoys 2 spacious bedrooms each with renovated ensuite bathrooms. Spacious covered porches off of 1st and 2nd floor and deeded carport complete this carefree tropical retreat!

2 Beds ⋅ 3 Baths ⋅ 619444 MLS

Stylish ''Spa'' home within the enclave of The Sanctuary of the Key West Golf Club. An open floor plan greets you to this light filled home that overlooks a private backyard oasis with dip pool, covered brick patio and maintenance free yard. Thoughtful kitchen updates including sleek quartz countertops with waterfall edge, stainless appliance package and new island lighting. The upstairs enjoys 2 spacious bedrooms each with renovated ensuite bathrooms. Spacious covered porches off of 1st and 2nd floor and deeded carport complete this carefree tropical retreat!

224 Golf Club Dr, Key West

$799,000

This elegant historic Old Town cottage is a rare offering paired with a highly competitive price. Completely turnkey and perfectly suited as a winter home or seasonal Key West escape, it offers the opportunity to simply arrive, settle in, and enjoy island life from day one. Sparkling, gallery-like, and filled with natural light, this beautifully renovated Old Town Key West cottage offers the perfect blend of charm, privacy, and modern comfort. Ideally situated on a quiet one-way street, this tropical retreat is just a short stroll from some of Key West's best boutiques, bakeries, art galleries, restaurants, and gourmet food markets. Renovated down to the studs, the home features vaulted ceilings and an open-concept layout where the gourmet kitchen, entertainment bar, and living area come together to create a bright, welcoming gathering space. True to the Key West lifestyle, an expansive sliding glass door opens to a serene tropical oasis framed by lush fig vines, Spanish lime trees, swaying palms, and a majestic Royal Poinciana tree, where morning coffee, afternoon cocktails, and evenings under the stars become part of everyday life. The property also offers dedicated off-street golf cart parking, potential for a small pool, and no HOA fees, further enhancing its appeal as a private sanctuary. Thoughtfully selected upscale finishes include solid teak flooring, granite countertops, and a beautifully appointed Calacatta marble shower tub. The renovation includes all-new electrical and plumbing systems, an efficient tankless hot water heater, a metal roof, impact-rated windows and opening protections, and stylish finishes throughout. Situated in the desirable X Flood Zone, the property offers an added layer of peace of mind with reduced flood risk concerns. Steeped in Key West history, this charming cottage was once home to a local cigar maker, offering a connection to the island's rich cultural heritage while embracing the pleasures of contemporary living.

1 Beds ⋅ 1 Baths ⋅ 621059 MLS

This elegant historic Old Town cottage is a rare offering paired with a highly competitive price. Completely turnkey and perfectly suited as a winter home or seasonal Key West escape, it offers the opportunity to simply arrive, settle in, and enjoy island life from day one. Sparkling, gallery-like, and filled with natural light, this beautifully renovated Old Town Key West cottage offers the perfect blend of charm, privacy, and modern comfort. Ideally situated on a quiet one-way street, this tropical retreat is just a short stroll from some of Key West's best boutiques, bakeries, art galleries, restaurants, and gourmet food markets. Renovated down to the studs, the home features vaulted ceilings and an open-concept layout where the gourmet kitchen, entertainment bar, and living area come together to create a bright, welcoming gathering space. True to the Key West lifestyle, an expansive sliding glass door opens to a serene tropical oasis framed by lush fig vines, Spanish lime trees, swaying palms, and a majestic Royal Poinciana tree, where morning coffee, afternoon cocktails, and evenings under the stars become part of everyday life. The property also offers dedicated off-street golf cart parking, potential for a small pool, and no HOA fees, further enhancing its appeal as a private sanctuary. Thoughtfully selected upscale finishes include solid teak flooring, granite countertops, and a beautifully appointed Calacatta marble shower tub. The renovation includes all-new electrical and plumbing systems, an efficient tankless hot water heater, a metal roof, impact-rated windows and opening protections, and stylish finishes throughout. Situated in the desirable X Flood Zone, the property offers an added layer of peace of mind with reduced flood risk concerns. Steeped in Key West history, this charming cottage was once home to a local cigar maker, offering a connection to the island's rich cultural heritage while embracing the pleasures of contemporary living.

1105 Olivia St, Key West

$759,000

Opportunity in the desirable Lime Grove neighborhood of New Town Key West! Situated on an oversized corner lot, this CBS home offers 1,242 sq. ft. of living area, an expansive yard and plenty of possibilities for its next owner. Owned by the same family for decades, the property has been lovingly maintained and is ready for its next chapter. Originally designed as a three-bedroom home, two of the bedrooms were opened into one another by removing the dividing wall, creating one oversized bedroom. The third bedroom remains separate, and the original three-bedroom configuration could potentially be restored by a new owner by adding the dividing wall. The generous corner lot provides abundant outdoor space with plenty of room to create a tropical outdoor living area and potential for a pool. The property also includes a detached 483 sq. ft. CBS garage/workshop in need of significant repair and rehabilitation, offering the potential to restore and repurpose the structure. Attached to the rear of the garage is a 228 sq. ft. utility/laundry/storage space. Inside, the home retains much of its original character with ample potential for updating and personalization. Whether envisioned as a primary residence, long-term rental investment or renovation project, the spacious lot, CBS construction, flexible layout and New Town location provide a great foundation for its next chapter. Just steps from Lake McKillip, take an evening stroll along the public wooden walkway over the water and enjoy beautiful Key West sunsets. Conveniently located in New Town near shopping centers, schools, the senior center, beaches and everything the island has to offer. Bring your vision and discover the possibilities at 2804 Harris Avenue.

2 Beds ⋅ 1 Baths ⋅ 620989 MLS

Opportunity in the desirable Lime Grove neighborhood of New Town Key West! Situated on an oversized corner lot, this CBS home offers 1,242 sq. ft. of living area, an expansive yard and plenty of possibilities for its next owner. Owned by the same family for decades, the property has been lovingly maintained and is ready for its next chapter. Originally designed as a three-bedroom home, two of the bedrooms were opened into one another by removing the dividing wall, creating one oversized bedroom. The third bedroom remains separate, and the original three-bedroom configuration could potentially be restored by a new owner by adding the dividing wall. The generous corner lot provides abundant outdoor space with plenty of room to create a tropical outdoor living area and potential for a pool. The property also includes a detached 483 sq. ft. CBS garage/workshop in need of significant repair and rehabilitation, offering the potential to restore and repurpose the structure. Attached to the rear of the garage is a 228 sq. ft. utility/laundry/storage space. Inside, the home retains much of its original character with ample potential for updating and personalization. Whether envisioned as a primary residence, long-term rental investment or renovation project, the spacious lot, CBS construction, flexible layout and New Town location provide a great foundation for its next chapter. Just steps from Lake McKillip, take an evening stroll along the public wooden walkway over the water and enjoy beautiful Key West sunsets. Conveniently located in New Town near shopping centers, schools, the senior center, beaches and everything the island has to offer. Bring your vision and discover the possibilities at 2804 Harris Avenue.

2804 Harris Ave, Key West

$750,000

TRANSIENT LICENCE RECEIVERSHIP ZONE! Welcome to your slice of paradise in Key West! This charming 2-bedroom, 2-bathroom condo located just steps from Duval Street offers an incredible opportunity. Currently utilized as an income-producing vacation rental, this home presents the perfect blend of comfort and convenience. Nestled in the heart of Key West, this condo boasts proximity to renowned attractions, vibrant restaurants, and the lively energy of Duval Street, ensuring endless entertainment options for residents and guests alike. Just a few blocks away lies Key West's South Beach, where sun-soaked days and breathtaking sunrises await. The interior of this inviting condo features two spacious bedrooms, providing ample room for relaxation and rejuvenation after a day of exploring the island. The well-appointed bathrooms offer both style and functionality, catering to the needs of residents and visitors. Whether you're lounging on the private balcony, enjoying the tropical breeze, or venturing out to experience the vibrant culture of Key West, this condo offers the quintessential island lifestyle. Don't miss your chance to own a piece of paradise and capitalize on the flourishing vacation rental market in this coveted location. Seize this opportunity to invest in Key West living at its finest. Schedule your showing today and envision the endless possibilities that await in this delightful condo just steps from Duval Street!

2 Beds ⋅ 2 Baths ⋅ 620157 MLS

TRANSIENT LICENCE RECEIVERSHIP ZONE! Welcome to your slice of paradise in Key West! This charming 2-bedroom, 2-bathroom condo located just steps from Duval Street offers an incredible opportunity. Currently utilized as an income-producing vacation rental, this home presents the perfect blend of comfort and convenience. Nestled in the heart of Key West, this condo boasts proximity to renowned attractions, vibrant restaurants, and the lively energy of Duval Street, ensuring endless entertainment options for residents and guests alike. Just a few blocks away lies Key West's South Beach, where sun-soaked days and breathtaking sunrises await. The interior of this inviting condo features two spacious bedrooms, providing ample room for relaxation and rejuvenation after a day of exploring the island. The well-appointed bathrooms offer both style and functionality, catering to the needs of residents and visitors. Whether you're lounging on the private balcony, enjoying the tropical breeze, or venturing out to experience the vibrant culture of Key West, this condo offers the quintessential island lifestyle. Don't miss your chance to own a piece of paradise and capitalize on the flourishing vacation rental market in this coveted location. Seize this opportunity to invest in Key West living at its finest. Schedule your showing today and envision the endless possibilities that await in this delightful condo just steps from Duval Street!

508 Louisa St Unit 3, Key West

$650,000

3 bedroom single-family home offering the opportunity to add a second bathroom within the existing roofline. Relax on the covered front porch and enjoy the Key West lifestyle. The private backyard provides space for a pool or outdoor entertaining. A great chance to renovate and make this home your own.

3 Beds ⋅ 1 Baths ⋅ 618808 MLS

3 bedroom single-family home offering the opportunity to add a second bathroom within the existing roofline. Relax on the covered front porch and enjoy the Key West lifestyle. The private backyard provides space for a pool or outdoor entertaining. A great chance to renovate and make this home your own.

1425 Eliza St, Key West