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This large home on an extra large 6300 sf corner lot is an excellent opportunity for a renovation project. The main home is just under 1600 sf and consists of 4 bedrooms and 2 bathrooms and there is also a good sized detached structure of almost 200 sf that could be turned in to, among other ideas, an extra bedroom, artist's studio or pool cabana. The home had the roof replaced in 2014 and has storm shutters. There are terrazzo floors. The extra large lot has sour orange, Spanish lime and banana trees, off street parking and plenty of room for a pool.

4 Beds ⋅ 2 Baths ⋅ 620315 MLS

This large home on an extra large 6300 sf corner lot is an excellent opportunity for a renovation project. The main home is just under 1600 sf and consists of 4 bedrooms and 2 bathrooms and there is also a good sized detached structure of almost 200 sf that could be turned in to, among other ideas, an extra bedroom, artist's studio or pool cabana. The home had the roof replaced in 2014 and has storm shutters. There are terrazzo floors. The extra large lot has sour orange, Spanish lime and banana trees, off street parking and plenty of room for a pool.

3746 Paula Ave, 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

$439,000

Lowest-Priced Commercial Retail Space in Old Town -- Offering an 8% CAP Rate. Positioned along high-visibility Truman Avenue, this commercial condominium delivers exceptional exposure in the heart of Key West, surrounded by a vibrant mix of shops, restaurants, residences, and historic attractions. The flexible space is well suited for retail, professional office, salon, studio, or gallery use. Recent improvements include new flooring, fresh interior paint, and a renovated bathroom, creating a clean, turnkey environment ready for immediate occupancy. Strong pedestrian and vehicle traffic add to the appeal of this established Old Town commercial corridor. HOA is $576/month and includes building insurance, exterior maintenance, and common-area care. An outstanding opportunity for an owner-user or investor seeking an accessible entry point into the Old Town commercial market. Schedule your private showing today.

1 Baths ⋅ 620196 MLS

Lowest-Priced Commercial Retail Space in Old Town -- Offering an 8% CAP Rate. Positioned along high-visibility Truman Avenue, this commercial condominium delivers exceptional exposure in the heart of Key West, surrounded by a vibrant mix of shops, restaurants, residences, and historic attractions. The flexible space is well suited for retail, professional office, salon, studio, or gallery use. Recent improvements include new flooring, fresh interior paint, and a renovated bathroom, creating a clean, turnkey environment ready for immediate occupancy. Strong pedestrian and vehicle traffic add to the appeal of this established Old Town commercial corridor. HOA is $576/month and includes building insurance, exterior maintenance, and common-area care. An outstanding opportunity for an owner-user or investor seeking an accessible entry point into the Old Town commercial market. Schedule your private showing today.

1012 Truman Ave Unit 6, Key West

$3,295,000

This large restaurant/bar in the heart of downtown Key West is presently rented for $18,000 NNN a month with over three years remaining on the lease. The location is excellent and the building has an effective rebuild date of 2005. The present tenant may be negotiable. Buy a piece of Key West. Call today.

2 Baths ⋅ 620183 MLS

This large restaurant/bar in the heart of downtown Key West is presently rented for $18,000 NNN a month with over three years remaining on the lease. The location is excellent and the building has an effective rebuild date of 2005. The present tenant may be negotiable. Buy a piece of Key West. Call today.

404 Southard St Unit 2, 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

$639,000

Discover your ideal pied-à-terre in the heart of Key West! This charming 1-bedroom, 1-bathroom apartment on Olivia Street offers a perfect blend of comfort and convenience. Featuring two balconies, you can enjoy your morning coffee or unwind in the evening while soaking up the tropical vibes. The cozy living space is adorned with modern finishes, complemented by a well-equipped kitchen that makes entertaining a breeze. Located just steps from local attractions, exquisite dining, and vibrant nightlife, this apartment is an excellent choice for those seeking the ultimate island lifestyle. Experience your perfect getaway in this Key West gem!

1 Beds ⋅ 1 Baths ⋅ 620158 MLS

Discover your ideal pied-à-terre in the heart of Key West! This charming 1-bedroom, 1-bathroom apartment on Olivia Street offers a perfect blend of comfort and convenience. Featuring two balconies, you can enjoy your morning coffee or unwind in the evening while soaking up the tropical vibes. The cozy living space is adorned with modern finishes, complemented by a well-equipped kitchen that makes entertaining a breeze. Located just steps from local attractions, exquisite dining, and vibrant nightlife, this apartment is an excellent choice for those seeking the ultimate island lifestyle. Experience your perfect getaway in this Key West gem!

1402 Olivia St Unit 2, 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

$1,300,000

Embrace the enchantment of Old Key West Charm in this Beautifully Updated Historic Conch 3 Bedroom-2 Bath Home, featuring a Tropical Landscaped community Pool creating ultimate relaxation. This timeless Conch Cottage is nestled in a secure gated compound of six Key West Style Cottages. Low HOA Fee $288 Monthly includes Pool and Landscaping maintenance. This home is in an X500 Flood Zone, Banks do not require Flood Insurance. Situated in the highly coveted Old Town North neighborhood, this home is in the heart of everything quintessentially Key West. Revel in the exquisite architecture, savor the diverse culinary delights, explore unique boutiques, and immerse yourself in the vibrant nightlife and rich cultural scene just a leisurely stroll from your doorstep. Just four blocks to the Historic Seaport and across from the iconic Five Brothers Coffee Shop. The renovated Living Room, Dining Room, and Kitchen features classic Vaulted Wood Ceilings, and Hard Wood Flooring. The renovated Modern Bathroom also features a Vaulted Wood Ceiling, and a spacious Glass and Tile Walk-In Shower, Custom Lighting, Custom Sink-Vanity, and Custom Mirrors. The lovely, renovated Kitchen features Stainless Steel Appliances, Custom Wood Cabinets, and a Custom Ceiling Fan-Light fixture. A spacious Covered and Screened Wood Accented Patio area connects the Main 2 Bedroom - 1 Bathroom Cottage to the adjoining Studio 1 Bedroom - 1 Bathroom separate living area. The Studio has a New AC Unit, Refrigerator, Microwave Oven, and an Air Fryer Oven. The Studio Bathroom has also been renovated with a Modern Glass and Tile Walk-In Shower, Custom Sink, Custom Lighted Mirror, and Custom Lighting. Both living areas have their own separate and private door entrances. Excellent Rental Income opportunity. This ideal 3BR-2BA floor plan can accommodate the owner living in one side, while renting the other side. Paradise Awaits in Old Town North Key West.

3 Beds ⋅ 2 Baths ⋅ 620150 MLS

Embrace the enchantment of Old Key West Charm in this Beautifully Updated Historic Conch 3 Bedroom-2 Bath Home, featuring a Tropical Landscaped community Pool creating ultimate relaxation. This timeless Conch Cottage is nestled in a secure gated compound of six Key West Style Cottages. Low HOA Fee $288 Monthly includes Pool and Landscaping maintenance. This home is in an X500 Flood Zone, Banks do not require Flood Insurance. Situated in the highly coveted Old Town North neighborhood, this home is in the heart of everything quintessentially Key West. Revel in the exquisite architecture, savor the diverse culinary delights, explore unique boutiques, and immerse yourself in the vibrant nightlife and rich cultural scene just a leisurely stroll from your doorstep. Just four blocks to the Historic Seaport and across from the iconic Five Brothers Coffee Shop. The renovated Living Room, Dining Room, and Kitchen features classic Vaulted Wood Ceilings, and Hard Wood Flooring. The renovated Modern Bathroom also features a Vaulted Wood Ceiling, and a spacious Glass and Tile Walk-In Shower, Custom Lighting, Custom Sink-Vanity, and Custom Mirrors. The lovely, renovated Kitchen features Stainless Steel Appliances, Custom Wood Cabinets, and a Custom Ceiling Fan-Light fixture. A spacious Covered and Screened Wood Accented Patio area connects the Main 2 Bedroom - 1 Bathroom Cottage to the adjoining Studio 1 Bedroom - 1 Bathroom separate living area. The Studio has a New AC Unit, Refrigerator, Microwave Oven, and an Air Fryer Oven. The Studio Bathroom has also been renovated with a Modern Glass and Tile Walk-In Shower, Custom Sink, Custom Lighted Mirror, and Custom Lighting. Both living areas have their own separate and private door entrances. Excellent Rental Income opportunity. This ideal 3BR-2BA floor plan can accommodate the owner living in one side, while renting the other side. Paradise Awaits in Old Town North Key West.

611 Grinnell St Unit 4, Key West

$1,239,000

OPEN HOUSE 09/19 from 11AM to 1PM Home has just been freshly painted and Is vacant easy to show. Owner also will give 5k credit towards buyers closing expenses Welcome to one of the most sought after gated communities in Key West Seaside Residences. This beautiful updated 2-bedroom 3.5 half bath offers 1824sq. ft of living space. It is a three-level townhouse with your own private elevator that accommodates all three levels. You have four private balconies on the top two floors which gives you a perfect view of the beautiful sunrises and sunsets. Not to mention that the roof deck has its private surroundings for beautiful views of the Atlantic Ocean and suntanning. On the first floor you will pull up to your private garage. There is also your laundry and half bath with Air conditioning. The rest of the first floor is your Bar/BBQ and ample space for entertaining your family and guests. This townhome comes with one of the few units with extra side yard which is turf with a putting green. Moving to the second floor there is your primary suite and ensuite bathroom with double vanities. There is a large shower for relaxing. Second bedroom also has its private full bath. Third floor opens to the main living room ocean view which flows to the dining room. The Kitchen features wood cabinetry with lots of storage. Granite countertops. Stainless Appliances and plenty of pantry storage, there is abundance of natural sunlight that flows across from large windows and doors. Townhouse comes with all impact hurricane windows and doors. Washer and dryer are fairly new (2023) and tankless water heater as well (2023). Air Condition replaced in September of 2023. (Priced to Sell). Included in your HOA fees are your insurances, pool and fitness center. Owner does hold a Florida Real Estate License

2 Beds ⋅ 4 Baths ⋅ 620140 MLS

OPEN HOUSE 09/19 from 11AM to 1PM Home has just been freshly painted and Is vacant easy to show. Owner also will give 5k credit towards buyers closing expenses Welcome to one of the most sought after gated communities in Key West Seaside Residences. This beautiful updated 2-bedroom 3.5 half bath offers 1824sq. ft of living space. It is a three-level townhouse with your own private elevator that accommodates all three levels. You have four private balconies on the top two floors which gives you a perfect view of the beautiful sunrises and sunsets. Not to mention that the roof deck has its private surroundings for beautiful views of the Atlantic Ocean and suntanning. On the first floor you will pull up to your private garage. There is also your laundry and half bath with Air conditioning. The rest of the first floor is your Bar/BBQ and ample space for entertaining your family and guests. This townhome comes with one of the few units with extra side yard which is turf with a putting green. Moving to the second floor there is your primary suite and ensuite bathroom with double vanities. There is a large shower for relaxing. Second bedroom also has its private full bath. Third floor opens to the main living room ocean view which flows to the dining room. The Kitchen features wood cabinetry with lots of storage. Granite countertops. Stainless Appliances and plenty of pantry storage, there is abundance of natural sunlight that flows across from large windows and doors. Townhouse comes with all impact hurricane windows and doors. Washer and dryer are fairly new (2023) and tankless water heater as well (2023). Air Condition replaced in September of 2023. (Priced to Sell). Included in your HOA fees are your insurances, pool and fitness center. Owner does hold a Florida Real Estate License

25 Seaside South Ct, Key West

$839,000

*** BEST PRICED 2/2 CONDO IN OLD TOWN *** Lionsgate community, heart of Old Town, one of Key West's most coveted small communities, known for its heated saltwater pool, lush tropical landscaping, and neighbors who actually know each other. Unit 321 sits on the second floor with vaulted ceilings, exposed beams, and an open layout that lives significantly larger than 944 sq ft. The kitchen and living room flow together naturally, good for cooking, entertaining, or simply unwinding. Quartz countertops, new laminate flooring, and fresh paint throughout make this move-in ready. Storage is genuinely rare here: a dedicated laundry room, an attic, and an assigned parking space at the unit. EV and golf-cart charging ready. X flood zone. This is a second home that actually feels like one.

2 Beds ⋅ 2 Baths ⋅ 620130 MLS

*** BEST PRICED 2/2 CONDO IN OLD TOWN *** Lionsgate community, heart of Old Town, one of Key West's most coveted small communities, known for its heated saltwater pool, lush tropical landscaping, and neighbors who actually know each other. Unit 321 sits on the second floor with vaulted ceilings, exposed beams, and an open layout that lives significantly larger than 944 sq ft. The kitchen and living room flow together naturally, good for cooking, entertaining, or simply unwinding. Quartz countertops, new laminate flooring, and fresh paint throughout make this move-in ready. Storage is genuinely rare here: a dedicated laundry room, an attic, and an assigned parking space at the unit. EV and golf-cart charging ready. X flood zone. This is a second home that actually feels like one.

1124 Olivia St Unit 321, Key West

$1,999,999

Tucked into the heart of Old Town, this beautifully restored residence pairs Key West's historic character with thoughtful modern updates--all just one block off Duval Street and three blocks from the iconic Southernmost Point. Taken down to the studs and fully renovated in 2018, the three-bedroom, two-bath home delivers high-end finishes throughout, plus the rare bonuses of a private gated courtyard and off-street parking. The layout is built for easy island living, blurring the line between indoors and out. Refined touches run throughout: impact-rated doors and windows, rich oak floors, custom tilework, and original Dade County Pine that's been carefully preserved. At the center of it all, the kitchen is made for entertaining, with stainless appliances, brushed marble counters, and eye-catching copper and bronze fixtures. The generously sized primary suite is a true retreat--vaulted cypress ceilings, a spa-inspired en suite, a showpiece copper soaking tub, and custom closets with room to spare. Add in abundant storage and easy-care landscaping, and the practical details are covered too. For buyers chasing style, comfort, and true walkability in one of Key West's most sought-after neighborhoods, this one belongs at the top of the list.

3 Beds ⋅ 2 Baths ⋅ 620106 MLS

Tucked into the heart of Old Town, this beautifully restored residence pairs Key West's historic character with thoughtful modern updates--all just one block off Duval Street and three blocks from the iconic Southernmost Point. Taken down to the studs and fully renovated in 2018, the three-bedroom, two-bath home delivers high-end finishes throughout, plus the rare bonuses of a private gated courtyard and off-street parking. The layout is built for easy island living, blurring the line between indoors and out. Refined touches run throughout: impact-rated doors and windows, rich oak floors, custom tilework, and original Dade County Pine that's been carefully preserved. At the center of it all, the kitchen is made for entertaining, with stainless appliances, brushed marble counters, and eye-catching copper and bronze fixtures. The generously sized primary suite is a true retreat--vaulted cypress ceilings, a spa-inspired en suite, a showpiece copper soaking tub, and custom closets with room to spare. Add in abundant storage and easy-care landscaping, and the practical details are covered too. For buyers chasing style, comfort, and true walkability in one of Key West's most sought-after neighborhoods, this one belongs at the top of the list.

1119 Whitehead St, Key West

$900,000

*Seller Motivated, told us to bring all reasonable Offers. 3/1 with a guest cottage/office space at rear of property with private full bath and kitchenette. 4/2 with cottage. All just awaiting a Buyers personal taste!. Huge lot with incredible area for big a beautiful pool! This is a perfect family 3/1 home in one of the best New Town neighborhoods. This fully gated home sits on a massive 7000 sf oversized lot and is completely move-in ready. The home boasts three bedrooms and one bath. The floor plan in the kitchen and living area flows perfectly for open living. Glass French doors open to the back patio (that could be enclosed for Florida room) and look out at the massive green lawn and native trees. The large back yard is perfect for expansion or creating your very own tropical oasis. Set back in complete privacy is a beautiful guest suite/office space with bath. The side yard with an additional privacy fence is perfect boat parking. This property is a must see! Occupied so must allow 24 hour notice.

3 Beds ⋅ 2 Baths ⋅ 620104 MLS

*Seller Motivated, told us to bring all reasonable Offers. 3/1 with a guest cottage/office space at rear of property with private full bath and kitchenette. 4/2 with cottage. All just awaiting a Buyers personal taste!. Huge lot with incredible area for big a beautiful pool! This is a perfect family 3/1 home in one of the best New Town neighborhoods. This fully gated home sits on a massive 7000 sf oversized lot and is completely move-in ready. The home boasts three bedrooms and one bath. The floor plan in the kitchen and living area flows perfectly for open living. Glass French doors open to the back patio (that could be enclosed for Florida room) and look out at the massive green lawn and native trees. The large back yard is perfect for expansion or creating your very own tropical oasis. Set back in complete privacy is a beautiful guest suite/office space with bath. The side yard with an additional privacy fence is perfect boat parking. This property is a must see! Occupied so must allow 24 hour notice.

1227 20th, 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

1901 S Roosevelt Blvd Unit 401S, Key West

$890,000

Major price improvement for an amazing full ocean view penthouse unit! Presumably the best view in the preferred South Wing of La Brisa Condominiums, enjoy a panoramic view of the Atlantic Ocean and all the activity and fun of Smather's Beach. Ready for your improvements, the condo has a modern open floor plan, spacious master suite with a large walk in closet, and a private balcony to enjoy the view. There is ultimate convenience from the condo unit to the assigned covered parking and storage. Meticulously maintained with professional on site management, La Brisa Condominiums feature superb amenities like a heated swimming pool, hot tub, saunas, a clubhouse, lighted tennis/pickleball court, car wash and grilling area. There is even a complimentary EV charging station. The home is available for your immediate occupancy, with no leases in place or follow on seller occupancy requirements. Centrally located on Key West, with bike paths and public transportation nearby, the Southmost City is yours to explore. Photos depicting furnishings have been virtually staged. Now priced for only $890,000!

2 Beds ⋅ 2 Baths ⋅ 620086 MLS

Major price improvement for an amazing full ocean view penthouse unit! Presumably the best view in the preferred South Wing of La Brisa Condominiums, enjoy a panoramic view of the Atlantic Ocean and all the activity and fun of Smather's Beach. Ready for your improvements, the condo has a modern open floor plan, spacious master suite with a large walk in closet, and a private balcony to enjoy the view. There is ultimate convenience from the condo unit to the assigned covered parking and storage. Meticulously maintained with professional on site management, La Brisa Condominiums feature superb amenities like a heated swimming pool, hot tub, saunas, a clubhouse, lighted tennis/pickleball court, car wash and grilling area. There is even a complimentary EV charging station. The home is available for your immediate occupancy, with no leases in place or follow on seller occupancy requirements. Centrally located on Key West, with bike paths and public transportation nearby, the Southmost City is yours to explore. Photos depicting furnishings have been virtually staged. Now priced for only $890,000!

1901 S Roosevelt Blvd Unit 401S, Key West

$1,250,000

With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

2 Beds ⋅ 2 Baths ⋅ 620075 MLS

With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

1911 Seidenberg Ave, 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

$1,249,000

Welcome to this beautifully renovated 3-bedroom, 2-bathroom home that perfectly blends modern finishes with warm, inviting living spaces. From the moment you arrive, you'll love the charming curb appeal, spacious covered front porch, and bright, airy interior filled with natural light. The heart of the home is the stunning chef's kitchen featuring an oversized quartz island, custom white shaker cabinetry, stainless steel appliances, abundant storage, and sleek designer finishes throughout. The open-concept layout flows seamlessly into the living and dining areas, making it ideal for entertaining and everyday living. The bedrooms offer comfort and flexibility, and both bathrooms have been thoughtfully updated with clean, modern touches. Located in a desirable neighborhood close to schools, shopping, dining, and local amenities, this move-in-ready home offers the perfect combination of style, comfort, and functionality.

3 Beds ⋅ 2 Baths ⋅ 620013 MLS

Welcome to this beautifully renovated 3-bedroom, 2-bathroom home that perfectly blends modern finishes with warm, inviting living spaces. From the moment you arrive, you'll love the charming curb appeal, spacious covered front porch, and bright, airy interior filled with natural light. The heart of the home is the stunning chef's kitchen featuring an oversized quartz island, custom white shaker cabinetry, stainless steel appliances, abundant storage, and sleek designer finishes throughout. The open-concept layout flows seamlessly into the living and dining areas, making it ideal for entertaining and everyday living. The bedrooms offer comfort and flexibility, and both bathrooms have been thoughtfully updated with clean, modern touches. Located in a desirable neighborhood close to schools, shopping, dining, and local amenities, this move-in-ready home offers the perfect combination of style, comfort, and functionality.

2116 Fogarty Ave, 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

$2,500,000

Discover an exceptional investment opportunity in the heart of the Florida Keys! Situated on a spacious lot just 3 minutes from the beach and world-famous Duval Street, this unique multi-unit property offers versatility, comfort, and island-style living at its finest. The main residence features 5 bedrooms and 3 bathrooms across 2,432 total s/f, designed for both relaxation and entertaining. Enjoy a private pool with pool heater, along with the convenience of two elevated A/C units, both less than 4 years old. The second unit offers 3 bedrooms and 1 bathroom with 1,504 total s/f of living space, plus a 2-car garage and its own elevated A/C unit, also less than 4 years old. Built for peace of mind and modern living, the property includes a durable metal roof, impact windows throughout, camera security system, preparation for an electric vehicle charger, and separate electric and water meters for each unit. Whether you're seeking a primary residence, vacation retreat, or income-producing property, this rare Florida Keys gem combines location, flexibility, and outstanding features in one incredible package.

8 Beds ⋅ 4 Baths ⋅ 619978 MLS

Discover an exceptional investment opportunity in the heart of the Florida Keys! Situated on a spacious lot just 3 minutes from the beach and world-famous Duval Street, this unique multi-unit property offers versatility, comfort, and island-style living at its finest. The main residence features 5 bedrooms and 3 bathrooms across 2,432 total s/f, designed for both relaxation and entertaining. Enjoy a private pool with pool heater, along with the convenience of two elevated A/C units, both less than 4 years old. The second unit offers 3 bedrooms and 1 bathroom with 1,504 total s/f of living space, plus a 2-car garage and its own elevated A/C unit, also less than 4 years old. Built for peace of mind and modern living, the property includes a durable metal roof, impact windows throughout, camera security system, preparation for an electric vehicle charger, and separate electric and water meters for each unit. Whether you're seeking a primary residence, vacation retreat, or income-producing property, this rare Florida Keys gem combines location, flexibility, and outstanding features in one incredible package.

1409 Whalton St, Key West

$3,400,000

Located within the quiet, gated security of Old Town Villas, this 3-bedroom, 3-bathroom townhome offers a sophisticated, low-maintenance island retreat just one block off of Duval St. Built in 2017, with solid concrete construction, this exceptional residence blends contemporary elegance with a thoughtfully designed layout that maximizes privacy, comfort, and functionality. Stepping inside, the interior is highlighted by beautiful tile flooring that runs seamlessly throughout. The main level features an open-concept layout with a spacious living room and chef's kitchen complete with stainless steel appliances and granite peninsula offering abundant prep space and casual seating. Just off the kitchen, a flexible-use room can serve as a dining area or private bedroom suite, complete with its own ensuite bathroom. A hallmark of this property is the extensive amount of premium, custom-built cabinetry and shelving installed throughout by the California Closets, offering unparalleled storage and organization. For effortless luxury, a private elevator services all four levels, transporting you from the two-car garage all the way to the rooftop terrace. The third floor hosts two spacious ensuite bedrooms, each featuring private balconies and large walk-in closets complete with custom organizational systems. The top floor is dedicated to an open living room and office area--a flexible bonus space filled with natural light. Step out from this upper lounge onto the spectacular rooftop terrace, equipped with custom awnings for comfortable shade, designed to capture both sunrise serenity and vibrant sunset views. For total peace of mind, the home features impact-rated windows and doors throughout. Beyond your front door, enjoy the exclusive community amenities, including a large pool and cabana. Conveniently situated near the very best dining and boutiques Key West has to offer, this home delivers the ultimate blend of privacy, location and the coveted Key West lifestyle.

3 Beds ⋅ 3 Baths ⋅ 619959 MLS

Located within the quiet, gated security of Old Town Villas, this 3-bedroom, 3-bathroom townhome offers a sophisticated, low-maintenance island retreat just one block off of Duval St. Built in 2017, with solid concrete construction, this exceptional residence blends contemporary elegance with a thoughtfully designed layout that maximizes privacy, comfort, and functionality. Stepping inside, the interior is highlighted by beautiful tile flooring that runs seamlessly throughout. The main level features an open-concept layout with a spacious living room and chef's kitchen complete with stainless steel appliances and granite peninsula offering abundant prep space and casual seating. Just off the kitchen, a flexible-use room can serve as a dining area or private bedroom suite, complete with its own ensuite bathroom. A hallmark of this property is the extensive amount of premium, custom-built cabinetry and shelving installed throughout by the California Closets, offering unparalleled storage and organization. For effortless luxury, a private elevator services all four levels, transporting you from the two-car garage all the way to the rooftop terrace. The third floor hosts two spacious ensuite bedrooms, each featuring private balconies and large walk-in closets complete with custom organizational systems. The top floor is dedicated to an open living room and office area--a flexible bonus space filled with natural light. Step out from this upper lounge onto the spectacular rooftop terrace, equipped with custom awnings for comfortable shade, designed to capture both sunrise serenity and vibrant sunset views. For total peace of mind, the home features impact-rated windows and doors throughout. Beyond your front door, enjoy the exclusive community amenities, including a large pool and cabana. Conveniently situated near the very best dining and boutiques Key West has to offer, this home delivers the ultimate blend of privacy, location and the coveted Key West lifestyle.

141 Simonton 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

$2,290,000

MOTIVATED SELLER! Prime Old Town Key West Location with 55 ft of Truman Avenue Frontage and Fantastic Off Street Parking. The property currently consists of four licensed rental apartments; one 2BR/1BA unit and three 1BR/1BA units. Flexible layout supports a variety of uses including long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with commercial use on the ground level and residential above. The property also offers the potential to be a duplex or reimagined as a spacious single-family residence. Property formerly configured for two business offices. Perfect for your business downstairs and reside upstairs. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. This is an extremely well-located property with multiple use possibilities. Buyer to verify any conversion from existing use.

5 Beds ⋅ 4 Baths ⋅ 619930 MLS

MOTIVATED SELLER! Prime Old Town Key West Location with 55 ft of Truman Avenue Frontage and Fantastic Off Street Parking. The property currently consists of four licensed rental apartments; one 2BR/1BA unit and three 1BR/1BA units. Flexible layout supports a variety of uses including long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with commercial use on the ground level and residential above. The property also offers the potential to be a duplex or reimagined as a spacious single-family residence. Property formerly configured for two business offices. Perfect for your business downstairs and reside upstairs. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. This is an extremely well-located property with multiple use possibilities. Buyer to verify any conversion from existing use.

1104 Truman Ave, Key West

$2,290,000

Four Apartment Property with Off Street Parking in a Prime Old Town Key West Location with LOTS of OPTIONS! 1104 Truman Avenue is a legal four-unit property with multiple use possibilities. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. The property currently consists of one 2BR/1BA unit and three 1BR/1BA units, all licensed rentals.. Flexible layout supports a variety of uses including long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with possible commercial use on the ground level and residential above. The property also offers the potential to be a duplex or reimagined as a spacious single-family residence. (Buyer to verify) This is an extremely well-located property with multiple use possibilities in a high-demand rental market.

5 Beds ⋅ 4 Baths ⋅ 619927 MLS

Four Apartment Property with Off Street Parking in a Prime Old Town Key West Location with LOTS of OPTIONS! 1104 Truman Avenue is a legal four-unit property with multiple use possibilities. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. The property currently consists of one 2BR/1BA unit and three 1BR/1BA units, all licensed rentals.. Flexible layout supports a variety of uses including long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with possible commercial use on the ground level and residential above. The property also offers the potential to be a duplex or reimagined as a spacious single-family residence. (Buyer to verify) This is an extremely well-located property with multiple use possibilities in a high-demand rental market.

1104 Truman Ave, Key West

$1,350,000

Real estate only. No business included. By appointment only, do not disturb business. This commercial building sits on over 1 acre of land at the entrance to the Key West Golf Club community, just off College Road. Currently configured with large showroom, 7 offices, two separate entrances one ADA compliant full bath and full reception area. Plenty of parking in adjoining parking lot, plus additional parking in rear. (Over 12 spaces) Close to Lower Keys Medical Center and quick access to US 1. The property will be delivered vacant at closing. Seller is a Florida real estate broker.

1 Baths ⋅ 619883 MLS

Real estate only. No business included. By appointment only, do not disturb business. This commercial building sits on over 1 acre of land at the entrance to the Key West Golf Club community, just off College Road. Currently configured with large showroom, 7 offices, two separate entrances one ADA compliant full bath and full reception area. Plenty of parking in adjoining parking lot, plus additional parking in rear. (Over 12 spaces) Close to Lower Keys Medical Center and quick access to US 1. The property will be delivered vacant at closing. Seller is a Florida real estate broker.

1 Golf Club Dr, Key West

$839,900

Welcome to island living in the highly sought-after Key West Golf Club community! This beautifully maintained home at 34 Golf Club Drive offers the perfect blend of comfort, upgrades, and convenience in a gated neighborhood just minutes from Old Town Key West. This light-filled home features an open-concept living area with soaring ceilings, luxury vinyl plank flooring, and sliding glass doors that bring the outdoors in. The updated kitchen offers quartz countertops, white cabinetry, stainless steel appliances, and a functional layout ideal for entertaining or everyday living. Thoughtful upgrades include impact windows on the front and back of the home, hurricane shutters for major entrances and side windows, spray foam insulation in the crawl space, and a newer air handler installed approximately five years ago. A new rear fence and gate provide direct access to the golf course, while peaceful views of the 5th and 6th holes and lagoon create a relaxing island atmosphere. The upstairs bedrooms feature beautiful vaulted ceilings, adding charm and an airy feel throughout the upper level. Outdoor spaces are surrounded by mature tropical landscaping, perfect for relaxing or entertaining. Additional highlights include a termite guarantee already in place for added peace of mind and an assumable VA loan for military buyers with an exceptionally low 1.99% interest rate. Subject to lender approval and VA guidelines. Non-military buyers may not assume the loan due to the fact, the seller wishes to keep his Entitlement. Residents of the Key West Golf Club community enjoy access to resort-style amenities including two pools, a fitness center, gated security, and beautifully maintained grounds. Whether you're searching for a primary residence, second home, or investment opportunity, this property captures the essence of easy Key West living.

3 Beds ⋅ 2 Baths ⋅ 619859 MLS

Welcome to island living in the highly sought-after Key West Golf Club community! This beautifully maintained home at 34 Golf Club Drive offers the perfect blend of comfort, upgrades, and convenience in a gated neighborhood just minutes from Old Town Key West. This light-filled home features an open-concept living area with soaring ceilings, luxury vinyl plank flooring, and sliding glass doors that bring the outdoors in. The updated kitchen offers quartz countertops, white cabinetry, stainless steel appliances, and a functional layout ideal for entertaining or everyday living. Thoughtful upgrades include impact windows on the front and back of the home, hurricane shutters for major entrances and side windows, spray foam insulation in the crawl space, and a newer air handler installed approximately five years ago. A new rear fence and gate provide direct access to the golf course, while peaceful views of the 5th and 6th holes and lagoon create a relaxing island atmosphere. The upstairs bedrooms feature beautiful vaulted ceilings, adding charm and an airy feel throughout the upper level. Outdoor spaces are surrounded by mature tropical landscaping, perfect for relaxing or entertaining. Additional highlights include a termite guarantee already in place for added peace of mind and an assumable VA loan for military buyers with an exceptionally low 1.99% interest rate. Subject to lender approval and VA guidelines. Non-military buyers may not assume the loan due to the fact, the seller wishes to keep his Entitlement. Residents of the Key West Golf Club community enjoy access to resort-style amenities including two pools, a fitness center, gated security, and beautifully maintained grounds. Whether you're searching for a primary residence, second home, or investment opportunity, this property captures the essence of easy Key West living.

34 Golf Club Dr, Key West

$1,250,000

With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

2 Beds ⋅ 2 Baths ⋅ 619758 MLS

With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

1911 Seidenberg Ave, Key West

$2,399,000

Discover a rare blend of history, artistry, and luxury in this extraordinary residence at the celebrated William Fleming House--one of Old Town Key West's most iconic and meticulously restored historic buildings. Originally constructed in the 1890s as Peacon's General Store, this architectural treasure has been transformed into an exclusive boutique condominium, exquisitely and entirely renovated. Inside, the first level condo rises to an unforgettable 16 feet, creating a sense of openness and serenity that feels both dramatic and inviting. Sunlight pours through impact-rated windows and doors, illuminating the vintage wood flooring and expansive walls that are ideal for showcasing meaningful art and personal collections. The thoughtfully designed layout includes two bedrooms, two full bathrooms, a half bath and a versatile loft space- accessed by a traditional staircase--offering remarkable flexibility for work, guests, creative pursuits, or quiet retreat. A private outdoor deck extends your living space and provides a peaceful spot for morning coffee or evening unwinding. The William Fleming House elevates daily living with its heated outdoor pool, lush tropical landscaping, and assigned off-street parking. Located in the desirable X-flood zone and directly across from Williams Hall, this residence places you in the heart of Old Town's cultural and architectural richness. With its unmatched scale, history, and character, this home invites you to bring your vision and transform it into a truly exceptional Key West sanctuary--one that reflects your style, your story, and your sense of place.

2 Beds ⋅ 3 Baths ⋅ 619742 MLS

Discover a rare blend of history, artistry, and luxury in this extraordinary residence at the celebrated William Fleming House--one of Old Town Key West's most iconic and meticulously restored historic buildings. Originally constructed in the 1890s as Peacon's General Store, this architectural treasure has been transformed into an exclusive boutique condominium, exquisitely and entirely renovated. Inside, the first level condo rises to an unforgettable 16 feet, creating a sense of openness and serenity that feels both dramatic and inviting. Sunlight pours through impact-rated windows and doors, illuminating the vintage wood flooring and expansive walls that are ideal for showcasing meaningful art and personal collections. The thoughtfully designed layout includes two bedrooms, two full bathrooms, a half bath and a versatile loft space- accessed by a traditional staircase--offering remarkable flexibility for work, guests, creative pursuits, or quiet retreat. A private outdoor deck extends your living space and provides a peaceful spot for morning coffee or evening unwinding. The William Fleming House elevates daily living with its heated outdoor pool, lush tropical landscaping, and assigned off-street parking. Located in the desirable X-flood zone and directly across from Williams Hall, this residence places you in the heart of Old Town's cultural and architectural richness. With its unmatched scale, history, and character, this home invites you to bring your vision and transform it into a truly exceptional Key West sanctuary--one that reflects your style, your story, and your sense of place.

800 Fleming St Unit Unit C1, Key West

$9,888,000

Fabulous Find on the Atlantic Side of Key West! Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing overhead, gentle breezes arriving at your lanai--it's an experience like nowhere else. This is island living at its finest! Permitted HCT uses include: Single-family and two-family residential dwellings, Multiple-family residential dwellings, Restaurant, Business and professional offices, Hotels, Motels, transient lodging, and more. This two-story home comes equipped with two separate electric meters. This exceptional property is truly one of a kind, with no identical or closely similar listings anywhere in Key West. The ideal circumstances are here and now-- an unparalleled combination of an oversized ocean-view lot, located just three blocks from Duval Street, the gateway to downtown. Spanning 8,700 square feet, this property offers ample space for your creative vision, whether you dream of building a luxurious residence, alongside a commercial venture boutique hotel, or restaurant, -- this and more are supported by HCT zoning. This property is all about the excitement of shaping a new vision for a future in paradise. Let your imagination run wild and transform this blank canvas into something extraordinary. Don't miss out on this once-in-lifetime opportunity--call today for your private tour and start envisioning your future in Key West!

3 Beds ⋅ 2 Baths ⋅ 619724 MLS

Fabulous Find on the Atlantic Side of Key West! Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing overhead, gentle breezes arriving at your lanai--it's an experience like nowhere else. This is island living at its finest! Permitted HCT uses include: Single-family and two-family residential dwellings, Multiple-family residential dwellings, Restaurant, Business and professional offices, Hotels, Motels, transient lodging, and more. This two-story home comes equipped with two separate electric meters. This exceptional property is truly one of a kind, with no identical or closely similar listings anywhere in Key West. The ideal circumstances are here and now-- an unparalleled combination of an oversized ocean-view lot, located just three blocks from Duval Street, the gateway to downtown. Spanning 8,700 square feet, this property offers ample space for your creative vision, whether you dream of building a luxurious residence, alongside a commercial venture boutique hotel, or restaurant, -- this and more are supported by HCT zoning. This property is all about the excitement of shaping a new vision for a future in paradise. Let your imagination run wild and transform this blank canvas into something extraordinary. Don't miss out on this once-in-lifetime opportunity--call today for your private tour and start envisioning your future in Key West!

1430 Vernon Ave, Key West

$1,875,000

DUPLEX! Discover the breathtaking corner property at Sunrise Shores, set on an expansive lot exceeding 13,000 square feet. POOL! The main residence offers over 1,750 square feet of living space, complemented by a detached guest cottage of 640 square feet. This meticulously maintained property has been cherished by its owners. The main home features three bedrooms and two bathrooms. It boasts a thoughtfully designed layout that includes a spacious family room and a large living room with a fireplace that opens up to the lanai. The primary bedroom provides direct access to the pool area and features an updated bathroom and a generous walk-in closet. The second bedroom also opens to the pool area, while the third bedroom is conveniently located next to the updated hall bath. There is also a laundry room with additional storage space. The detached guest cottage includes one bedroom and one bathroom. This property is perfect for owner-occupiers, investors, multi-generational living, and more.

4 Beds ⋅ 3 Baths ⋅ 619723 MLS

DUPLEX! Discover the breathtaking corner property at Sunrise Shores, set on an expansive lot exceeding 13,000 square feet. POOL! The main residence offers over 1,750 square feet of living space, complemented by a detached guest cottage of 640 square feet. This meticulously maintained property has been cherished by its owners. The main home features three bedrooms and two bathrooms. It boasts a thoughtfully designed layout that includes a spacious family room and a large living room with a fireplace that opens up to the lanai. The primary bedroom provides direct access to the pool area and features an updated bathroom and a generous walk-in closet. The second bedroom also opens to the pool area, while the third bedroom is conveniently located next to the updated hall bath. There is also a laundry room with additional storage space. The detached guest cottage includes one bedroom and one bathroom. This property is perfect for owner-occupiers, investors, multi-generational living, and more.

1516 17th Ter, Key West

$1,700,000

Strong value-add multifamily fourplex investment opportunity with major capital improvements already completed. The property offers four two-bedroom residences totaling approximately 3,000 square feet, with each unit comprising approximately 750 square feet. The lower level includes two residences, while the upper level features two additional residences with approximately 960 square feet of combined balcony space. Major improvements include a new standing-seam metal roof, new impact-resistant windows and doors throughout, and completed concrete, stucco, and exterior work. The property is ready for the next owner to complete the remaining work and execute their preferred investment strategy. Once completed and delivered furnished, the property is projected to have the potential to generate more than $200,000 in annual gross rental income across all four units. Additional potential may include condominium conversion, subject to all applicable approvals and requirements. A compelling opportunity to complete, stabilize, and maximize a well-positioned Key West income-producing asset.

4 Beds ⋅ 4 Baths ⋅ 619703 MLS

Strong value-add multifamily fourplex investment opportunity with major capital improvements already completed. The property offers four two-bedroom residences totaling approximately 3,000 square feet, with each unit comprising approximately 750 square feet. The lower level includes two residences, while the upper level features two additional residences with approximately 960 square feet of combined balcony space. Major improvements include a new standing-seam metal roof, new impact-resistant windows and doors throughout, and completed concrete, stucco, and exterior work. The property is ready for the next owner to complete the remaining work and execute their preferred investment strategy. Once completed and delivered furnished, the property is projected to have the potential to generate more than $200,000 in annual gross rental income across all four units. Additional potential may include condominium conversion, subject to all applicable approvals and requirements. A compelling opportunity to complete, stabilize, and maximize a well-positioned Key West income-producing asset.

1224 2nd St, Key West