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Dona Calabash - Located just a half a block from the upper end of Duval Street this charming Old Town beauty has it all! Three bedrooms including a luxurious master suite with spa bath, two guest bedrooms and two full baths. The gourmet kitchen features commercial grade stainless appliances, granite countertops and plenty of storage. Rear French doors open to a covered deck and the refreshing pool and surrounding lush gardens. The adjacent cabana house has a beautifully appointed bath and cozy sleeping/sitting area. Features here also include high ceilings, hardwood Brazilian cherry floors, Dade County pine feature walls, gorgeous grounds and a convenient electric gate for the off street parking for multiple vehicles. This property has been meticulously designed and maintained for the discerning new owners! Walking distance to the ocean, restaurants, shops and nightlife and still have privacy & quiet, this special fully appointed property is a must see.! Very easy to show!

3 Beds ⋅ 3 Baths ⋅ 616321 MLS

Dona Calabash - Located just a half a block from the upper end of Duval Street this charming Old Town beauty has it all! Three bedrooms including a luxurious master suite with spa bath, two guest bedrooms and two full baths. The gourmet kitchen features commercial grade stainless appliances, granite countertops and plenty of storage. Rear French doors open to a covered deck and the refreshing pool and surrounding lush gardens. The adjacent cabana house has a beautifully appointed bath and cozy sleeping/sitting area. Features here also include high ceilings, hardwood Brazilian cherry floors, Dade County pine feature walls, gorgeous grounds and a convenient electric gate for the off street parking for multiple vehicles. This property has been meticulously designed and maintained for the discerning new owners! Walking distance to the ocean, restaurants, shops and nightlife and still have privacy & quiet, this special fully appointed property is a must see.! Very easy to show!

410 Catherine St, Key West

$2,200,000

Epitome of Paradise! There is an enveloping comfort, an ease and repose, that beckons one away from the world's cares and invites one to lounge, drift away, and dream in this gorgeous waterfront condominium. Enjoy a single level open floor plan with two bedrooms, two full baths and a convenient powder room. Exquisitely decorated to reflect the local island flavor with all new furniture and furnishings, just bring your favorite book! There are several quiet places to sit back and enjoy which includes a breathtaking wrap around deck with views of the inner harbor, the Ocean, Sunset Key, and beyond. The adjacent covered dining area is perfect for those opportunities to sip, dine and dream while embracing the light, the climate, the trade winds, The waterfront heated pool complex boasts of breathtaking views from dawn to dusk! There is also a covered assigned parking space, #23, a full time security team and a true gated community experience with close proximity to the local park, Duval Street and the local nightlife!

2 Beds ⋅ 3 Baths ⋅ 614265 MLS

Epitome of Paradise! There is an enveloping comfort, an ease and repose, that beckons one away from the world's cares and invites one to lounge, drift away, and dream in this gorgeous waterfront condominium. Enjoy a single level open floor plan with two bedrooms, two full baths and a convenient powder room. Exquisitely decorated to reflect the local island flavor with all new furniture and furnishings, just bring your favorite book! There are several quiet places to sit back and enjoy which includes a breathtaking wrap around deck with views of the inner harbor, the Ocean, Sunset Key, and beyond. The adjacent covered dining area is perfect for those opportunities to sip, dine and dream while embracing the light, the climate, the trade winds, The waterfront heated pool complex boasts of breathtaking views from dawn to dusk! There is also a covered assigned parking space, #23, a full time security team and a true gated community experience with close proximity to the local park, Duval Street and the local nightlife!

105 Front St Unit 121, Key West

$2,200,000

Surprising water views combined with maximum privacy are the signature advantages of this luxurious & well positioned Overlook home on the exclusive private island of Sunset Key. The original owners bought pre-construction & added many thoughtful upgrades and architectural improvements. This three story, 2 bedroom, 2 & a half bath home has been well maintained & never rented. Years of planting & care have gone into creating maximum privacy with lush landscaping in all directions. The pure realization of a true tropical escape: quiet, serene & secure, with no automobiles, world class amenities including an oceanfront restaurant & bar, full service spa, beautiful sand beaches, community resort style pool, tennis courts & fitness center. Plus Overlook has its own separate heated swimming pool as well. All of this just a quick ferry ride available every half hour to connect to all the action that Key West has to offer. A truly unique island experience! Check it out.

2 Beds ⋅ 3 Baths ⋅ 618441 MLS

Surprising water views combined with maximum privacy are the signature advantages of this luxurious & well positioned Overlook home on the exclusive private island of Sunset Key. The original owners bought pre-construction & added many thoughtful upgrades and architectural improvements. This three story, 2 bedroom, 2 & a half bath home has been well maintained & never rented. Years of planting & care have gone into creating maximum privacy with lush landscaping in all directions. The pure realization of a true tropical escape: quiet, serene & secure, with no automobiles, world class amenities including an oceanfront restaurant & bar, full service spa, beautiful sand beaches, community resort style pool, tennis courts & fitness center. Plus Overlook has its own separate heated swimming pool as well. All of this just a quick ferry ride available every half hour to connect to all the action that Key West has to offer. A truly unique island experience! Check it out.

68 Sunset, Key West

$2,200,000

3605 Eagle Avenue | Key West Situated on one of Key West's most desirable streets, this private compound on Eagle Avenue offers a rare combination of space, privacy, and refined island living. Set on a double corner lot totaling 12,000 sq ft, the property is fully enclosed, offering enhanced privacy and a tranquil, resort-like setting. The main residence features 3 bedrooms, 2.5 baths, and approximately 1,765 sq ft of thoughtfully designed living space with a comfortable open floor plan ideal for entertaining. The spacious primary suite serves as a private retreat, complete with a large en suite bath featuring a walk-in shower and oversized Jacuzzi tub. A separate guest cottage offers 1 bedroom, 1 bath, and approximately 625 sq ft, providing excellent flexibility for guests, extended family, or additional living space. The professionally landscaped grounds are a standout feature, enhanced by landscape lighting and irrigation, and centered around a large pool set within an exceptionally private backyard. Outdoor amenities include a hammock and swing area, outdoor shower, and multiple areas for entertaining or quiet relaxation beneath the palms. Additional highlights include a whole-house generator, security system, one-car garage, and generous off-street parking. Surrounded by notable luxury homes, Eagle Avenue is known for its quiet atmosphere, large lots, and enduring desirability. A rare opportunity to own a private Key West compound offering privacy, flexibility, and presence on one of the island's most sought-after streets. Seller is a licensed real estate agent

4 Beds ⋅ 4 Baths ⋅ 618197 MLS

3605 Eagle Avenue | Key West Situated on one of Key West's most desirable streets, this private compound on Eagle Avenue offers a rare combination of space, privacy, and refined island living. Set on a double corner lot totaling 12,000 sq ft, the property is fully enclosed, offering enhanced privacy and a tranquil, resort-like setting. The main residence features 3 bedrooms, 2.5 baths, and approximately 1,765 sq ft of thoughtfully designed living space with a comfortable open floor plan ideal for entertaining. The spacious primary suite serves as a private retreat, complete with a large en suite bath featuring a walk-in shower and oversized Jacuzzi tub. A separate guest cottage offers 1 bedroom, 1 bath, and approximately 625 sq ft, providing excellent flexibility for guests, extended family, or additional living space. The professionally landscaped grounds are a standout feature, enhanced by landscape lighting and irrigation, and centered around a large pool set within an exceptionally private backyard. Outdoor amenities include a hammock and swing area, outdoor shower, and multiple areas for entertaining or quiet relaxation beneath the palms. Additional highlights include a whole-house generator, security system, one-car garage, and generous off-street parking. Surrounded by notable luxury homes, Eagle Avenue is known for its quiet atmosphere, large lots, and enduring desirability. A rare opportunity to own a private Key West compound offering privacy, flexibility, and presence on one of the island's most sought-after streets. Seller is a licensed real estate agent

3605 Eagle Ave, Key West

$2,200,000

There are streets in Old Town that everyone knows, and then there are streets like Elgin Lane that most people never even realize exist. Quiet, tucked away, and remarkably private, this hidden lane offers what buyers search for endlessly in Old Town privacy, off street parking, and a pool, all in one of the most desirable locations in Key West. 1116 Elgin Lane is a 3 bedroom, 2 bath home located in the Historic Seaport District, seamlessly blending authentic Key West history with thoughtful modern updates. The original structure dates back to the 1850s, and rich Dade County Pine walls and floors bring a warmth and character that simply cannot be replicated today. The kitchen serves as the heart of the home, featuring stainless steel appliances, granite countertops, and a wine cooler, all overlooking a dramatic vaulted living and dining area. Two sets of French doors open to an updated composite deck and covered porch, creating effortless indoor outdoor living. Beyond, a lush backyard centers around a 23 foot heated saltwater pool with waterfall feature and swim jets, complemented by a wet bar and outdoor shower, making the space equally suited for entertaining or quiet relaxation. On the main level, a spacious bedroom with beautiful Dade County Pine accents is paired with a full bathroom featuring a deep soaking tub and striking Brazilian slate floors. A generous office or den adds flexibility and can easily function as an additional bedroom if needed. Upstairs, the entire level is dedicated to the primary suite, complete with a full bathroom finished in Brazilian slate and two large closets offering ample storage. Recent improvements include new AC systems, updated windows, an on demand water heater, and storm shutters for all windows and doors. Quiet, central, and layered with history, 1116 Elgin Lane is one of Old Town's most compelling hidden opportunities and a rare chance to own a truly private retreat in the heart of Key West.

3 Beds ⋅ 2 Baths ⋅ 618303 MLS

There are streets in Old Town that everyone knows, and then there are streets like Elgin Lane that most people never even realize exist. Quiet, tucked away, and remarkably private, this hidden lane offers what buyers search for endlessly in Old Town privacy, off street parking, and a pool, all in one of the most desirable locations in Key West. 1116 Elgin Lane is a 3 bedroom, 2 bath home located in the Historic Seaport District, seamlessly blending authentic Key West history with thoughtful modern updates. The original structure dates back to the 1850s, and rich Dade County Pine walls and floors bring a warmth and character that simply cannot be replicated today. The kitchen serves as the heart of the home, featuring stainless steel appliances, granite countertops, and a wine cooler, all overlooking a dramatic vaulted living and dining area. Two sets of French doors open to an updated composite deck and covered porch, creating effortless indoor outdoor living. Beyond, a lush backyard centers around a 23 foot heated saltwater pool with waterfall feature and swim jets, complemented by a wet bar and outdoor shower, making the space equally suited for entertaining or quiet relaxation. On the main level, a spacious bedroom with beautiful Dade County Pine accents is paired with a full bathroom featuring a deep soaking tub and striking Brazilian slate floors. A generous office or den adds flexibility and can easily function as an additional bedroom if needed. Upstairs, the entire level is dedicated to the primary suite, complete with a full bathroom finished in Brazilian slate and two large closets offering ample storage. Recent improvements include new AC systems, updated windows, an on demand water heater, and storm shutters for all windows and doors. Quiet, central, and layered with history, 1116 Elgin Lane is one of Old Town's most compelling hidden opportunities and a rare chance to own a truly private retreat in the heart of Key West.

1116 Elgin Ln, Key West

$2,200,000

Beautiful home in the Casa Marina District. Completely remodeled in 2020 and the guest cottage is new construction. Main home has two bedrooms and two full bathrooms and one half bathroom , with one of the bedroom and bathroom located exclusively on the second floor. Living area and kitchen have vaulted ceilings with a beutiful open floor plan perfect for entertaining that opens up to the heated and chilled pool. The cottage has one bedroom and one bath with a separate living area off the pool, perfect for guests or a large home office space. The home is an active vacation rental. Perfect for an investor or someone wanting ot off-set the costs of a second home. Minutes away from the beaches, parks, bocce courts and still walking distance or a nice bike ride to downtown Key West's exciting activities. There is a driveway for parking and ample street parking as well. The landscaping has an irrigation system for worry free maintainence and the yard offers an amazing outdoor entertaining space. The entire property is secured away with a fence for privacy. This is a must see listing, dont miss out! We cant wait to show it to you.

3 Beds ⋅ 4 Baths ⋅ 614690 MLS

Beautiful home in the Casa Marina District. Completely remodeled in 2020 and the guest cottage is new construction. Main home has two bedrooms and two full bathrooms and one half bathroom , with one of the bedroom and bathroom located exclusively on the second floor. Living area and kitchen have vaulted ceilings with a beutiful open floor plan perfect for entertaining that opens up to the heated and chilled pool. The cottage has one bedroom and one bath with a separate living area off the pool, perfect for guests or a large home office space. The home is an active vacation rental. Perfect for an investor or someone wanting ot off-set the costs of a second home. Minutes away from the beaches, parks, bocce courts and still walking distance or a nice bike ride to downtown Key West's exciting activities. There is a driveway for parking and ample street parking as well. The landscaping has an irrigation system for worry free maintainence and the yard offers an amazing outdoor entertaining space. The entire property is secured away with a fence for privacy. This is a must see listing, dont miss out! We cant wait to show it to you.

1124 Seminary St, Key West

$2,180,000

This timeless home exudes historic charm while offering the comforts and finishes of modern island living. Step inside to discover a thoughtfully designed layout with soaring ceilings, rich hardwood floors, and natural light streaming through oversized windows and French doors. The open concept living area flows seamlessly to an outdoor tropical oasis complete with a heated pool, lush landscaping, and spacious sundeck, ideal for relaxing or entertaining, along with a 1 bed / 1 bath cottage, perfect for guests. Each bedroom offers ensuite privacy, and the kitchen is a chef's dream with propane stove and plenty of prep space. Enjoy cool island evenings from your wraparound porch or take a short stroll to the nearby white sands of the Atlantic Ocean, the galleries of Duval Street, or your favorite local café.

3 Beds ⋅ 4 Baths ⋅ 618044 MLS

This timeless home exudes historic charm while offering the comforts and finishes of modern island living. Step inside to discover a thoughtfully designed layout with soaring ceilings, rich hardwood floors, and natural light streaming through oversized windows and French doors. The open concept living area flows seamlessly to an outdoor tropical oasis complete with a heated pool, lush landscaping, and spacious sundeck, ideal for relaxing or entertaining, along with a 1 bed / 1 bath cottage, perfect for guests. Each bedroom offers ensuite privacy, and the kitchen is a chef's dream with propane stove and plenty of prep space. Enjoy cool island evenings from your wraparound porch or take a short stroll to the nearby white sands of the Atlantic Ocean, the galleries of Duval Street, or your favorite local café.

622 Louisa St, Key West

$2,170,000

The Triple C -- with the Two P's. Classic Conch Cottage. Plus Parking and a Pool. Ideally located in the highly sought-after Casa Marina neighborhood, arguably Key West's premier residential enclave, 1308 Reynolds Street offers 3 bedrooms and 3 baths just a few blocks from the sand and situated in the X-500 flood zone. The thoughtfully designed layout blends classic Key West architecture with distinctive design elements throughout, featuring a 2 bedroom, 2 bath main home plus office/library where artisan stonework and custom woodwork add warmth and craftsmanship. A detached studio guest cottage with its own bath provides ideal guest accommodations. Lush tropical landscaping frames the property, while coral stone hardscape surrounds the pool and a hardwood deck connects the home and studio, creating a cohesive and inviting outdoor environment. A covered loggia enhances the connection between structures, and pocket sliding glass doors open the living room seamlessly to the pool deck for effortless indoor-outdoor living. Well maintained and rich in architectural character, the home presents a compelling opportunity to elevate to today's standards--offering the perfect canvas to shape your own vision of island living in one of Key West's most desirable locations.

3 Beds ⋅ 3 Baths ⋅ 618735 MLS

The Triple C -- with the Two P's. Classic Conch Cottage. Plus Parking and a Pool. Ideally located in the highly sought-after Casa Marina neighborhood, arguably Key West's premier residential enclave, 1308 Reynolds Street offers 3 bedrooms and 3 baths just a few blocks from the sand and situated in the X-500 flood zone. The thoughtfully designed layout blends classic Key West architecture with distinctive design elements throughout, featuring a 2 bedroom, 2 bath main home plus office/library where artisan stonework and custom woodwork add warmth and craftsmanship. A detached studio guest cottage with its own bath provides ideal guest accommodations. Lush tropical landscaping frames the property, while coral stone hardscape surrounds the pool and a hardwood deck connects the home and studio, creating a cohesive and inviting outdoor environment. A covered loggia enhances the connection between structures, and pocket sliding glass doors open the living room seamlessly to the pool deck for effortless indoor-outdoor living. Well maintained and rich in architectural character, the home presents a compelling opportunity to elevate to today's standards--offering the perfect canvas to shape your own vision of island living in one of Key West's most desirable locations.

1308 Reynolds St, Key West

$2,150,000

A true Historic Gem, meticulously restored to its former glory with a complete, ground-up revitalization. Every detail has been thoughtfully preserved and reimagined, blending timeless character with modern craftsmanship to create a stunning masterpiece that honors the past while embracing the future. Experience the ease and elegance of one-level living in this Island Inspired Retreat. This tropical haven features two impeccably styled bedrooms, each with it's own Spa-like en-suite and spacious closets for effortless organization. Accent wood wall finishes add warmth and character while the hand selected tropical wallpaper, infuses each space with a vibrant, vacation-like ambiance. The Charming finished half-story on the second floor is a dream hideaway designed for fun, comfort and unforgettable memories. This inviting space features four built-in bunks, creating a cozy camp-like retreat that's perfect for grandkids, visiting family or extra guests. Each bunk is adorned with luxurious hand-selected linens, making it as stylish as it is comfortable. Whether it's laughter-filled sleepovers or quiet afternoon naps, this whimsical bunk room promises to be a favorite spots for guests of all ages. The Spacious, thoughtfully designed kitchen is a gathering place for making memories, perfect for hosting family, friends and special occasions. The oversized island offers plenty of space for meal prep, casual dining or simply enjoying a cup of coffee while chatting with loved ones. From the Kitchen, you'll enjoy the picturesque views of the beautifully appointed tropical living and dining area, featuring elegant wallpaper, a Featured Wood Finished Wall, gorgeous window covering, custom blinds and a stunning coordinated furniture package. The open layout also connects to the private new pool and patio area, perfect for relaxed get-togethers, holiday celebrations or quiet evenings under the stars. Addn features inc, 3 OSP, Turnkey, Above Flood, Storage, privacy.

3 Beds ⋅ 3 Baths ⋅ 620937 MLS

A true Historic Gem, meticulously restored to its former glory with a complete, ground-up revitalization. Every detail has been thoughtfully preserved and reimagined, blending timeless character with modern craftsmanship to create a stunning masterpiece that honors the past while embracing the future. Experience the ease and elegance of one-level living in this Island Inspired Retreat. This tropical haven features two impeccably styled bedrooms, each with it's own Spa-like en-suite and spacious closets for effortless organization. Accent wood wall finishes add warmth and character while the hand selected tropical wallpaper, infuses each space with a vibrant, vacation-like ambiance. The Charming finished half-story on the second floor is a dream hideaway designed for fun, comfort and unforgettable memories. This inviting space features four built-in bunks, creating a cozy camp-like retreat that's perfect for grandkids, visiting family or extra guests. Each bunk is adorned with luxurious hand-selected linens, making it as stylish as it is comfortable. Whether it's laughter-filled sleepovers or quiet afternoon naps, this whimsical bunk room promises to be a favorite spots for guests of all ages. The Spacious, thoughtfully designed kitchen is a gathering place for making memories, perfect for hosting family, friends and special occasions. The oversized island offers plenty of space for meal prep, casual dining or simply enjoying a cup of coffee while chatting with loved ones. From the Kitchen, you'll enjoy the picturesque views of the beautifully appointed tropical living and dining area, featuring elegant wallpaper, a Featured Wood Finished Wall, gorgeous window covering, custom blinds and a stunning coordinated furniture package. The open layout also connects to the private new pool and patio area, perfect for relaxed get-togethers, holiday celebrations or quiet evenings under the stars. Addn features inc, 3 OSP, Turnkey, Above Flood, Storage, privacy.

1328 Duncan St, Key West

$2,150,000

TRANSIENT LICENSE! Welcome to your perfect blend of comfort, style, and investment opportunity! This beautifully maintained 2-bedroom, 2-bathroom single-family home offers an ideal retreat for both personal enjoyment and income generation. Step inside to discover a thoughtfully renovated interior featuring a modern kitchen with updated finishes and appliances, along with fully remodeled bathrooms designed for both elegance and functionality. Both bedrooms are enhanced with brand-new carpeting, creating a cozy and inviting atmosphere. Outdoors, you'll find a true oasis--a spacious covered seating area perfect for entertaining or relaxing year-round, all overlooking a large heated pool that elevates the home's resort-style appeal. This property comes with a highly sought-after Transient License, making it an exceptional investment with strong, consistent annual rental income. Please note: the buyer must honor all existing reservations currently on the books, allowing for a seamless transition and immediate revenue. Offered fully furnished, turnkey, less personal effects & artwork. Whether you're searching for a private getaway or a turnkey income-producing property, this home delivers on every level.

2 Beds ⋅ 2 Baths ⋅ 619348 MLS

TRANSIENT LICENSE! Welcome to your perfect blend of comfort, style, and investment opportunity! This beautifully maintained 2-bedroom, 2-bathroom single-family home offers an ideal retreat for both personal enjoyment and income generation. Step inside to discover a thoughtfully renovated interior featuring a modern kitchen with updated finishes and appliances, along with fully remodeled bathrooms designed for both elegance and functionality. Both bedrooms are enhanced with brand-new carpeting, creating a cozy and inviting atmosphere. Outdoors, you'll find a true oasis--a spacious covered seating area perfect for entertaining or relaxing year-round, all overlooking a large heated pool that elevates the home's resort-style appeal. This property comes with a highly sought-after Transient License, making it an exceptional investment with strong, consistent annual rental income. Please note: the buyer must honor all existing reservations currently on the books, allowing for a seamless transition and immediate revenue. Offered fully furnished, turnkey, less personal effects & artwork. Whether you're searching for a private getaway or a turnkey income-producing property, this home delivers on every level.

641 United St, Key West

$2,100,000

This beautifully renovated conch home is a proud recipient of the 2024 Historic Florida Keys Foundation Preservation Award. Originally constructed in 1906, the house has been meticulously restored from the ground up, essentially transforming it into a brand-new property. The home features off-street parking and a heated and chilled pool. It comes fully furnished for a turnkey experience. Ideally situated within walking distance of restaurants, art galleries, and Duval Street, the location is perfect for enjoyment. A spacious porch adorned with classic painted Cuban tiles offers a serene outdoor retreat, while reclaimed heart pine flooring flows throughout the interior. The open floor plan provides a seamless view from the living room to the pool deck, making it an excellent space for both relaxation and entertaining. The original tongue-and-groove Dade County Pine has been carefully removed, refinished, and reinstalled, creating a warm and inviting ambiance. The L-shaped kitchen, overlooking the heated dip pool, features custom craftsman shaker cabinets and quartz countertops. The master suite, conveniently located on the first floor, includes an en-suite bathroom with a walk-in shower. Two guest bedrooms, each with en-suite baths and vaulted ceilings, are located on the second floor. This home has been completely rewired, replumbed, and foam-insulated to meet modern building codes. A new foundation and reinforced metal shingle roof have been added, along with fabric hurricane shutters for protection and insurance benefits. Smart switches, appliances, locks, and wired Ethernet connectivity enable remote home management via phone. Located in the desired X Flood Zone, this property retains its historic charm, making it a remarkable piece of Key West history. Off Street Parking! The owner is a licensed Florida Real Estate Agent.

3 Beds ⋅ 4 Baths ⋅ 619307 MLS

This beautifully renovated conch home is a proud recipient of the 2024 Historic Florida Keys Foundation Preservation Award. Originally constructed in 1906, the house has been meticulously restored from the ground up, essentially transforming it into a brand-new property. The home features off-street parking and a heated and chilled pool. It comes fully furnished for a turnkey experience. Ideally situated within walking distance of restaurants, art galleries, and Duval Street, the location is perfect for enjoyment. A spacious porch adorned with classic painted Cuban tiles offers a serene outdoor retreat, while reclaimed heart pine flooring flows throughout the interior. The open floor plan provides a seamless view from the living room to the pool deck, making it an excellent space for both relaxation and entertaining. The original tongue-and-groove Dade County Pine has been carefully removed, refinished, and reinstalled, creating a warm and inviting ambiance. The L-shaped kitchen, overlooking the heated dip pool, features custom craftsman shaker cabinets and quartz countertops. The master suite, conveniently located on the first floor, includes an en-suite bathroom with a walk-in shower. Two guest bedrooms, each with en-suite baths and vaulted ceilings, are located on the second floor. This home has been completely rewired, replumbed, and foam-insulated to meet modern building codes. A new foundation and reinforced metal shingle roof have been added, along with fabric hurricane shutters for protection and insurance benefits. Smart switches, appliances, locks, and wired Ethernet connectivity enable remote home management via phone. Located in the desired X Flood Zone, this property retains its historic charm, making it a remarkable piece of Key West history. Off Street Parking! The owner is a licensed Florida Real Estate Agent.

816 Ashe St, Key West

$2,100,000

This stunning Florida ranch-style home has been completely remodeled to offer a blend of modern luxury and comfortable living. From the moment you step inside, you'll be captivated by the expansive open floor plan, which creates a seamless flow between the living spaces, ideal for both everyday living and entertaining. The heart of the home is the chef's kitchen, featuring high-end Café appliances with elegant bronze finishes, ensuring both style and functionality for any culinary enthusiast. Whether you're preparing a gourmet meal or enjoying a casual breakfast, the spacious layout offers ample room and top-of-the-line finishes that elevate the entire space. With four generously-sized bedrooms and three and a half baths, this home offers the perfect balance of privacy and shared space. Each bathroom is meticulously updated, offering sleek, modern fixtures and luxurious finishes. The master suite is an oasis of tranquility, complete with a spa-like ensuite bath designed for relaxation. Every detail of this home has been thoughtfully updated, including all new electric and plumbing systems, ensuring both convenience and peace of mind. The entire property is protected with brand-new impact-resistant glass, adding security and energy efficiency to the already impressive home. The oversized corner lot offers privacy and plenty of room for outdoor activities. The new in-ground pool is an entertainer's dream, providing a private retreat where you can relax and soak in the Florida sunshine. The massive back porch is perfect for hosting gatherings, with ample seating under the cool breeze of ceiling fans. The space is designed with tropical landscaping, creating a lush, serene environment that enhances the home's connection to nature. This home combines the best of modern design with the timeless charm of its original style. With meticulous attention to detail and a perfect blend of indoor and outdoor living spaces.

4 Beds ⋅ 4 Baths ⋅ 614406 MLS

This stunning Florida ranch-style home has been completely remodeled to offer a blend of modern luxury and comfortable living. From the moment you step inside, you'll be captivated by the expansive open floor plan, which creates a seamless flow between the living spaces, ideal for both everyday living and entertaining. The heart of the home is the chef's kitchen, featuring high-end Café appliances with elegant bronze finishes, ensuring both style and functionality for any culinary enthusiast. Whether you're preparing a gourmet meal or enjoying a casual breakfast, the spacious layout offers ample room and top-of-the-line finishes that elevate the entire space. With four generously-sized bedrooms and three and a half baths, this home offers the perfect balance of privacy and shared space. Each bathroom is meticulously updated, offering sleek, modern fixtures and luxurious finishes. The master suite is an oasis of tranquility, complete with a spa-like ensuite bath designed for relaxation. Every detail of this home has been thoughtfully updated, including all new electric and plumbing systems, ensuring both convenience and peace of mind. The entire property is protected with brand-new impact-resistant glass, adding security and energy efficiency to the already impressive home. The oversized corner lot offers privacy and plenty of room for outdoor activities. The new in-ground pool is an entertainer's dream, providing a private retreat where you can relax and soak in the Florida sunshine. The massive back porch is perfect for hosting gatherings, with ample seating under the cool breeze of ceiling fans. The space is designed with tropical landscaping, creating a lush, serene environment that enhances the home's connection to nature. This home combines the best of modern design with the timeless charm of its original style. With meticulous attention to detail and a perfect blend of indoor and outdoor living spaces.

1341 Tropical St, Key West

$2,100,000

Offered on Iconic Johnson Street - one of Key West's most coveted one-way streets surrounded by multi million dollar residences - this 1959 mid-century modern home presents a rare opportunity in the heart of the prestigious Casa Marina area. Just two short blocks from the beach, this is location at its absolute finest. Set on an oversized 7500 sq. ft. lot, this concrete-constructed residence offers an exceptional canvas for transformation. Influenced by Danish mid-century architecture, the home currently features three bedroom and two bathrooms and an expansive covered porch that could easily be enclosed to significantly increase interior square footage. Architectural discussions have already explored the addition of a second story, creating the potential to dramatically expand living space while capitalizing on the strength of existing concrete construction. The generous lot allows ample room for a pool, lanai, jacuzzi or tropical outdoor retreat, with a beautifully landscaped front garden and privacy in the rear. Additional highlights include a carport plus off-street parking for up to three vehicles, a rarity in this prime location. The home is livable as is, yet unmistakably primed for renovation or redevelopment to match the caliber of the surrounding properties. 1110 Johnson St. offers single level living today with the flexibility to expand tomorrow, all within walking distance to the beach, fine dining and the very best Key West has to offer. Opportunities like this - On Johnson St. in this location, on a lot of this size - are exceptionally rare.

3 Beds ⋅ 2 Baths ⋅ 618278 MLS

Offered on Iconic Johnson Street - one of Key West's most coveted one-way streets surrounded by multi million dollar residences - this 1959 mid-century modern home presents a rare opportunity in the heart of the prestigious Casa Marina area. Just two short blocks from the beach, this is location at its absolute finest. Set on an oversized 7500 sq. ft. lot, this concrete-constructed residence offers an exceptional canvas for transformation. Influenced by Danish mid-century architecture, the home currently features three bedroom and two bathrooms and an expansive covered porch that could easily be enclosed to significantly increase interior square footage. Architectural discussions have already explored the addition of a second story, creating the potential to dramatically expand living space while capitalizing on the strength of existing concrete construction. The generous lot allows ample room for a pool, lanai, jacuzzi or tropical outdoor retreat, with a beautifully landscaped front garden and privacy in the rear. Additional highlights include a carport plus off-street parking for up to three vehicles, a rarity in this prime location. The home is livable as is, yet unmistakably primed for renovation or redevelopment to match the caliber of the surrounding properties. 1110 Johnson St. offers single level living today with the flexibility to expand tomorrow, all within walking distance to the beach, fine dining and the very best Key West has to offer. Opportunities like this - On Johnson St. in this location, on a lot of this size - are exceptionally rare.

1110 Johnson St, Key West

$2,035,000

Second floor Harbour Place condominium features 2 bedrooms and 2.5 baths. Relax on your private balcony and admire the beautiful sunsets and views of the ocean, gulf and all the activity in Key West harbor. Recently updated, this beautiful property is move-in ready and has spectacular views from the large windows and both bedrooms. Easily accessible by the conveniently located elevator. One of the few Harbour Place units with 2 parking spaces, #15 and 16. Video Tour: https://show.tours/v/4MqLYGD

2 Beds ⋅ 3 Baths ⋅ 614831 MLS

Second floor Harbour Place condominium features 2 bedrooms and 2.5 baths. Relax on your private balcony and admire the beautiful sunsets and views of the ocean, gulf and all the activity in Key West harbor. Recently updated, this beautiful property is move-in ready and has spectacular views from the large windows and both bedrooms. Easily accessible by the conveniently located elevator. One of the few Harbour Place units with 2 parking spaces, #15 and 16. Video Tour: https://show.tours/v/4MqLYGD

107 Front St Unit 215, Key West

$2,030,000

Your Private Tropical Oasis in Mid-Town Key West awaits. Welcome to this beautifully renovated and thoughtfully designed ground-level 3BR/2BA CBS home, perfectly situated on a double corner lot in the heart of Mid-Town Key West. Just minutes from Old Town, shopping, and the island's best beaches, this residence offers the ideal balance of convenience, privacy, and luxury. Enclosed by a full privacy wall, the property invites you through a gated entrance into lush tropical landscaping. A charming brick pathway winds its way to the expansive backyard, where a stunning saltwater pool and jacuzzi create a true island retreat, perfect for both relaxation and entertaining. Inside, natural light pours through numerous windows, filling the home with warmth and brightness. The seamless indoor-outdoor connection keeps the tropical gardens and sparkling pool within view, reminding you that paradise is just outside your door. The interior design blends coastal modern style with Scandinavian simplicity, creating a fresh yet cozy atmosphere. The spacious kitchen, crafted with entertaining in mind, features stainless steel appliances, a large pantry room, and generous counter space making it the perfect gathering place for friends and family. From its open, sun-filled living spaces to its lush outdoor retreat, this property embodies the essence of Key West living. A rare opportunity to own a private tropical sanctuary in one of the island's most desirable neighborhoods.

3 Beds ⋅ 2 Baths ⋅ 616325 MLS

Your Private Tropical Oasis in Mid-Town Key West awaits. Welcome to this beautifully renovated and thoughtfully designed ground-level 3BR/2BA CBS home, perfectly situated on a double corner lot in the heart of Mid-Town Key West. Just minutes from Old Town, shopping, and the island's best beaches, this residence offers the ideal balance of convenience, privacy, and luxury. Enclosed by a full privacy wall, the property invites you through a gated entrance into lush tropical landscaping. A charming brick pathway winds its way to the expansive backyard, where a stunning saltwater pool and jacuzzi create a true island retreat, perfect for both relaxation and entertaining. Inside, natural light pours through numerous windows, filling the home with warmth and brightness. The seamless indoor-outdoor connection keeps the tropical gardens and sparkling pool within view, reminding you that paradise is just outside your door. The interior design blends coastal modern style with Scandinavian simplicity, creating a fresh yet cozy atmosphere. The spacious kitchen, crafted with entertaining in mind, features stainless steel appliances, a large pantry room, and generous counter space making it the perfect gathering place for friends and family. From its open, sun-filled living spaces to its lush outdoor retreat, this property embodies the essence of Key West living. A rare opportunity to own a private tropical sanctuary in one of the island's most desirable neighborhoods.

1322 George St, Key West

$2,000,000

Situated in the heart of Old Town Key West, this exceptional multi-family property offers four well-maintained 2-bedroom, 2-bathroom apartments—perfectly positioned for strong, consistent rental income. Just a short stroll to Duval Street, renowned restaurants, the Truman Waterfront, and local attractions, this property is ideally located for long-term or monthly rentals. Each unit features a private entrance, full kitchen, and a bright, functional layout, making it a turnkey opportunity for investors. The property also includes a 3,898 sq ft vacant lot directly behind the main building, offering rare development or expansion potential. The lot benefits from a dedicated access strip that connects directly to the frontage road, providing valuable street access and enhancing its usability for future projects. Whether you're looking to expand your portfolio, develop additional units, or simply hold a high-demand rental asset with room to grow, this is a rare find in one of Key West's most desirable neighborhoods.

8 Beds ⋅ 8 Baths ⋅ 615878 MLS

Situated in the heart of Old Town Key West, this exceptional multi-family property offers four well-maintained 2-bedroom, 2-bathroom apartments—perfectly positioned for strong, consistent rental income. Just a short stroll to Duval Street, renowned restaurants, the Truman Waterfront, and local attractions, this property is ideally located for long-term or monthly rentals. Each unit features a private entrance, full kitchen, and a bright, functional layout, making it a turnkey opportunity for investors. The property also includes a 3,898 sq ft vacant lot directly behind the main building, offering rare development or expansion potential. The lot benefits from a dedicated access strip that connects directly to the frontage road, providing valuable street access and enhancing its usability for future projects. Whether you're looking to expand your portfolio, develop additional units, or simply hold a high-demand rental asset with room to grow, this is a rare find in one of Key West's most desirable neighborhoods.

909 & 913 Thomas St, Key West

$1,965,000

1706 Seminary Street delivers the space, flexibility, and outdoor lifestyle that can be surprisingly difficult to find in Key West. Set behind a new privacy fence on an expansive 7,480SF lot, the home is near an impressive collection of beautifully maintained and upscale residences, adding to the appeal of this desirable neighborhood. This completely renovated 3 bed, 3 bath home offers nearly 2,000SF of beautifully updated living space, including a versatile third bedroom with its own private entrance, ideal for visiting friends and family, a private home office, or potential rental use. At the heart of the home is a striking new kitchen featuring quartz waterfall countertops, custom cabinetry, new KitchenAid stainless steel appliances, and an open design that connects naturally to the surrounding living spaces. One of the home's most inviting spaces is the glass windows surrounding the family room, where abundant natural light and views of the tropical backyard create a connection to the outdoors. Outside is where this property truly comes into its own. Meandering pathways weave through lush tropical landscaping and connect multiple areas designed for enjoying the Key West lifestyle. A resort style L shaped lap pool anchors the backyard, complemented by 2 covered lounging areas, a Bahama inspired outdoor dining space, an outdoor shower, and a secure storage shed. Along the side of the property, another unique opportunity awaits. With a modification to the existing fence, there is potential for approximately 20ft of covered boat storage, an increasingly valuable feature for anyone looking to keep their boat protected from the Key West sun and weather. Private, beautifully renovated, and designed to make the most of its generous lot, the property offers a rare combination of indoor comfort, outdoor living, and everyday functionality. Whether enjoyed as a primary residence or an island retreat, everything is already in place to start living the Key West lifestyle.

3 Beds ⋅ 3 Baths ⋅ 620712 MLS

1706 Seminary Street delivers the space, flexibility, and outdoor lifestyle that can be surprisingly difficult to find in Key West. Set behind a new privacy fence on an expansive 7,480SF lot, the home is near an impressive collection of beautifully maintained and upscale residences, adding to the appeal of this desirable neighborhood. This completely renovated 3 bed, 3 bath home offers nearly 2,000SF of beautifully updated living space, including a versatile third bedroom with its own private entrance, ideal for visiting friends and family, a private home office, or potential rental use. At the heart of the home is a striking new kitchen featuring quartz waterfall countertops, custom cabinetry, new KitchenAid stainless steel appliances, and an open design that connects naturally to the surrounding living spaces. One of the home's most inviting spaces is the glass windows surrounding the family room, where abundant natural light and views of the tropical backyard create a connection to the outdoors. Outside is where this property truly comes into its own. Meandering pathways weave through lush tropical landscaping and connect multiple areas designed for enjoying the Key West lifestyle. A resort style L shaped lap pool anchors the backyard, complemented by 2 covered lounging areas, a Bahama inspired outdoor dining space, an outdoor shower, and a secure storage shed. Along the side of the property, another unique opportunity awaits. With a modification to the existing fence, there is potential for approximately 20ft of covered boat storage, an increasingly valuable feature for anyone looking to keep their boat protected from the Key West sun and weather. Private, beautifully renovated, and designed to make the most of its generous lot, the property offers a rare combination of indoor comfort, outdoor living, and everyday functionality. Whether enjoyed as a primary residence or an island retreat, everything is already in place to start living the Key West lifestyle.

1706 Seminary St, Key West

$1,950,000

Welcome to your dream island retreat at 1313 Atlantic Drive in sunny Key West! This beautifully updated single-family home offers the best of coastal living with peace of mind — built in 2014 to the latest building codes for better insurance rates, featuring impact glass windows and doors, concrete siding, and an elevated structure above base flood. The roof has even been upgraded with new screws for extra durability. Step inside and you'll find fresh paint throughout, a sleek updated kitchen and baths, high-end appliances, and new flooring on the main level. There's a full bedroom and bath on the first floor, plus two spacious en-suites upstairs — each with private decks to soak up the breeze. Outside, the lush tropical landscaping wraps around a heated pool and fenced yard, perfect for entertaining or just relaxing in paradise. A butler's pantry adds extra storage and function, the extra-wide staircase makes a statement, and a smartly designed desk nook keeps things practical. Off-street parking for two is the cherry on top. Don't miss your chance to own a modern, move-in ready Key West gem — come see what island living is all about!

3 Beds ⋅ 3 Baths ⋅ 617905 MLS

Welcome to your dream island retreat at 1313 Atlantic Drive in sunny Key West! This beautifully updated single-family home offers the best of coastal living with peace of mind — built in 2014 to the latest building codes for better insurance rates, featuring impact glass windows and doors, concrete siding, and an elevated structure above base flood. The roof has even been upgraded with new screws for extra durability. Step inside and you'll find fresh paint throughout, a sleek updated kitchen and baths, high-end appliances, and new flooring on the main level. There's a full bedroom and bath on the first floor, plus two spacious en-suites upstairs — each with private decks to soak up the breeze. Outside, the lush tropical landscaping wraps around a heated pool and fenced yard, perfect for entertaining or just relaxing in paradise. A butler's pantry adds extra storage and function, the extra-wide staircase makes a statement, and a smartly designed desk nook keeps things practical. Off-street parking for two is the cherry on top. Don't miss your chance to own a modern, move-in ready Key West gem — come see what island living is all about!

1313 Atlantic Dr, Key West

$1,925,000

ELEVATE YOUR QUALITY OF LIFE. Positioned within the highly sought-after Casa Marina district with unique design 1104 South St will appeal to those who demand the best in quality design, finishes, and lifestyle. The indoor-outdoor spaces are seamlessly connected by stack-away sliding-glass doors, promoting a flawless integration of outdoor/indoor living with architectural detailing that adds a romantic touch. The property is surrounded by landscaped gardens and a tranquil pool with a water feature that provides the soothing sound of the water throughout the home. The new kitchen has ample counter space, is equipped with stainless appliances, and adjoins the dining room for easy communication between hosts and guests. The lower level contains office space, a full bedroom, and 1.5 baths. On the second floor, you'll find an airy, light-filled master suite with a walk-in closet, ensuite bathroom with an oversized soaking tub and two adjoining balconies. A second guest suite is accessible from the circular exterior staircase, complete with a private balcony and bathroom. Garage and off-street parking, private entry, and courtyard designed for comfort and practicality while maintaining aesthetic excellence. This property presents an outstanding lifestyle or vacation rental investment opportunity. Schedule your private tour now.

3 Beds ⋅ 4 Baths ⋅ 613992 MLS

ELEVATE YOUR QUALITY OF LIFE. Positioned within the highly sought-after Casa Marina district with unique design 1104 South St will appeal to those who demand the best in quality design, finishes, and lifestyle. The indoor-outdoor spaces are seamlessly connected by stack-away sliding-glass doors, promoting a flawless integration of outdoor/indoor living with architectural detailing that adds a romantic touch. The property is surrounded by landscaped gardens and a tranquil pool with a water feature that provides the soothing sound of the water throughout the home. The new kitchen has ample counter space, is equipped with stainless appliances, and adjoins the dining room for easy communication between hosts and guests. The lower level contains office space, a full bedroom, and 1.5 baths. On the second floor, you'll find an airy, light-filled master suite with a walk-in closet, ensuite bathroom with an oversized soaking tub and two adjoining balconies. A second guest suite is accessible from the circular exterior staircase, complete with a private balcony and bathroom. Garage and off-street parking, private entry, and courtyard designed for comfort and practicality while maintaining aesthetic excellence. This property presents an outstanding lifestyle or vacation rental investment opportunity. Schedule your private tour now.

1104 South Street, Key West

$1,925,000

Bold design and thoughtful details set 3801 Flagler apart. This is not a copy-and-paste Key West home—it's the personal residence of an architect and a real estate broker, created to balance striking style with everyday comfort. Set on a generous 9,500 sq ft corner lot, the property features two distinct structures. The main residence showcases soaring 18-foot vaulted ceilings, a chef's kitchen with gas cooking and stainless appliances, a serene bedroom suite, and a spa-inspired bath. A sculptural concrete-and-metal stair leads to a versatile loft, perfect for reading, work, or creative retreat. The detached, oversized two-car garage, built in 2021 is rare for Key West—not just for storage but also climate-controlled, making it ideal as a gym, workshop, or (music) studio. Above, a 696 sq ft guest suite offers treetop privacy with flexible living space, bedroom, full bath, coffee bar, and a walk-in closet. Elevated above FEMA flood zone AE-8 and recently improved, the home is built for longevity and ease of ownership, with a whole-house generator for peace of mind during power outages. Outdoor spaces are just as intentional: a two-tier saltwater pool and deck framed by mature landscaping, coastal breezes, and custom corrugated metal and wood fencing that doubles as a design statement and privacy screen. For collectors, the restored 1974 Toyota Land Cruiser currently housed in the garage is available under separate negotiation. With its combination of architecture, flexibility, and outdoor living, 3801 Flagler delivers more than just a residence—it's a modern island compound with expansion potential, now priced to sell.

2 Beds ⋅ 2 Baths ⋅ 617124 MLS

Bold design and thoughtful details set 3801 Flagler apart. This is not a copy-and-paste Key West home—it's the personal residence of an architect and a real estate broker, created to balance striking style with everyday comfort. Set on a generous 9,500 sq ft corner lot, the property features two distinct structures. The main residence showcases soaring 18-foot vaulted ceilings, a chef's kitchen with gas cooking and stainless appliances, a serene bedroom suite, and a spa-inspired bath. A sculptural concrete-and-metal stair leads to a versatile loft, perfect for reading, work, or creative retreat. The detached, oversized two-car garage, built in 2021 is rare for Key West—not just for storage but also climate-controlled, making it ideal as a gym, workshop, or (music) studio. Above, a 696 sq ft guest suite offers treetop privacy with flexible living space, bedroom, full bath, coffee bar, and a walk-in closet. Elevated above FEMA flood zone AE-8 and recently improved, the home is built for longevity and ease of ownership, with a whole-house generator for peace of mind during power outages. Outdoor spaces are just as intentional: a two-tier saltwater pool and deck framed by mature landscaping, coastal breezes, and custom corrugated metal and wood fencing that doubles as a design statement and privacy screen. For collectors, the restored 1974 Toyota Land Cruiser currently housed in the garage is available under separate negotiation. With its combination of architecture, flexibility, and outdoor living, 3801 Flagler delivers more than just a residence—it's a modern island compound with expansion potential, now priced to sell.

3801 Flagler Ave, Key West

$1,920,000

X FLOOD ZONE! Exquisite retreat in the heart of Old Town Key West—an ideal private sanctuary with rental income. This remarkable home offers refined style, privacy, and a proven rental history, appealing to buyers who value luxury and the allure of a tropical lifestyle. Behind an unassuming facade lies a sophisticated residence filled with high-end details. Restored in 2017, this home features three spacious bedroom suites. The open floor plan flows seamlessly from a bright, inviting main living area to a gourmet kitchen equipped with vein-cut onyx and translucent Quartzite countertops that light up, Jenn Air stainless steel appliances, and a dedicated bar with a wine cooler—perfect for both entertaining and everyday indulgence. White oak flooring.The living area extends to a private backyard oasis with a covered outdoor lounge, a heated saltwater pool, outdoor shower surrounded by lush greenery. The second-floor suite boasts a private rooftop deck, an ideal space for sunbathing or stargazing. Set in the preferred X Flood Zone, with impact windows and doors, this home blends modern flair with classic Key West charm, featuring light-filled rooms, 14-foot tongue-and-groove ceilings, and white oak hardwood floors. The classic shotgun-style layout guides visitors from the welcoming hallway through to the tropical backyard, creating a tranquil escape perfect for relaxation or entertaining. In a prime location, the property is within walking or biking distance to Key West's best beaches, restaurants, and shops, allowing you to enjoy all that the area has to offer with no need for a car. Bonus is Off-street parking for a small car, a rare convenience in Old Town. This unique property, features an 8' x 4' Alan Maltz -a local artist- mural in the pool. Enjoy both seclusion and easy access to Key West's most popular spots. Don't miss your chance to own this luxurious home offering style, charm, and great rental income potential! Video https://tinyurl.com/1116Packer

3 Beds ⋅ 3 Baths ⋅ 612089 MLS

X FLOOD ZONE! Exquisite retreat in the heart of Old Town Key West—an ideal private sanctuary with rental income. This remarkable home offers refined style, privacy, and a proven rental history, appealing to buyers who value luxury and the allure of a tropical lifestyle. Behind an unassuming facade lies a sophisticated residence filled with high-end details. Restored in 2017, this home features three spacious bedroom suites. The open floor plan flows seamlessly from a bright, inviting main living area to a gourmet kitchen equipped with vein-cut onyx and translucent Quartzite countertops that light up, Jenn Air stainless steel appliances, and a dedicated bar with a wine cooler—perfect for both entertaining and everyday indulgence. White oak flooring.The living area extends to a private backyard oasis with a covered outdoor lounge, a heated saltwater pool, outdoor shower surrounded by lush greenery. The second-floor suite boasts a private rooftop deck, an ideal space for sunbathing or stargazing. Set in the preferred X Flood Zone, with impact windows and doors, this home blends modern flair with classic Key West charm, featuring light-filled rooms, 14-foot tongue-and-groove ceilings, and white oak hardwood floors. The classic shotgun-style layout guides visitors from the welcoming hallway through to the tropical backyard, creating a tranquil escape perfect for relaxation or entertaining. In a prime location, the property is within walking or biking distance to Key West's best beaches, restaurants, and shops, allowing you to enjoy all that the area has to offer with no need for a car. Bonus is Off-street parking for a small car, a rare convenience in Old Town. This unique property, features an 8' x 4' Alan Maltz -a local artist- mural in the pool. Enjoy both seclusion and easy access to Key West's most popular spots. Don't miss your chance to own this luxurious home offering style, charm, and great rental income potential! Video https://tinyurl.com/1116Packer

1116 Packer St, Key West

$1,900,000

Welcome to 413 Emma Street, Unit A - a rare opportunity to own a piece of Key West history in the prestigious Truman Annex. This elegant two-story, 2-bedroom, 2.5-bath villa is located in the exclusive Mills Place Condominiums, a unique enclave of just 20 residences, thoughtfully designed within charming bungalows and the original 1844 hospital by architect Robert Mills. This beautifully maintained home offers the perfect blend of historic character and modern comfort. The open-concept living and dining area features a cozy office nook and flows seamlessly to a covered porch—ideal for enjoying morning coffee, al fresco lunches, or evening cocktails in the tropical breeze. Upstairs, you'll find two spacious bedrooms, each with its own ensuite bath, while a convenient powder room and a fully equipped kitchen complete the main level. Bright, airy interiors and timeless architectural details capture the essence of relaxed island living. Step outside to your private garden oasis—perfect for entertaining, grilling, or simply unwinding amidst lush, tropical landscaping. Take a dip in your own private pool, or soak in sunset views over Truman Waterfront Park and the harbor from your balcony. This villa offers both privacy and convenience in one of Old Town's most desirable neighborhoods. Just a short stroll or bike ride brings you to Duval Street's dining and nightlife, boutique shopping, and Fort Zachary Taylor Beach. Whether you're searching for a primary residence, a vacation escape, or a high-value investment, this Mills Place villa is an exceptional find in the heart of Key West.

2 Beds ⋅ 3 Baths ⋅ 615666 MLS

Welcome to 413 Emma Street, Unit A - a rare opportunity to own a piece of Key West history in the prestigious Truman Annex. This elegant two-story, 2-bedroom, 2.5-bath villa is located in the exclusive Mills Place Condominiums, a unique enclave of just 20 residences, thoughtfully designed within charming bungalows and the original 1844 hospital by architect Robert Mills. This beautifully maintained home offers the perfect blend of historic character and modern comfort. The open-concept living and dining area features a cozy office nook and flows seamlessly to a covered porch—ideal for enjoying morning coffee, al fresco lunches, or evening cocktails in the tropical breeze. Upstairs, you'll find two spacious bedrooms, each with its own ensuite bath, while a convenient powder room and a fully equipped kitchen complete the main level. Bright, airy interiors and timeless architectural details capture the essence of relaxed island living. Step outside to your private garden oasis—perfect for entertaining, grilling, or simply unwinding amidst lush, tropical landscaping. Take a dip in your own private pool, or soak in sunset views over Truman Waterfront Park and the harbor from your balcony. This villa offers both privacy and convenience in one of Old Town's most desirable neighborhoods. Just a short stroll or bike ride brings you to Duval Street's dining and nightlife, boutique shopping, and Fort Zachary Taylor Beach. Whether you're searching for a primary residence, a vacation escape, or a high-value investment, this Mills Place villa is an exceptional find in the heart of Key West.

413 Emm St Unit A, Key West

$1,900,000

1015 Eaton Street, the art of island elegance, where historic soul meets modern sophistication. Four bedrooms. Updated baths. A new kitchen. Natural light everywhere. And a big, resort-style pool; a true rarity in Old Town! Positioned in the coveted heart of Old Key West, just steps from the Historic Seaport, 1015 Eaton Street is more than a home, it's a statement. A refined yet relaxed retreat that delivers space, style, and privacy in one of the most walkable neighborhoods in Key West. The home opens in a wash of natural light, with a crisp, effortless aesthetic that is polished and inviting. Living spaces connect seamlessly, creating a layout that lives as well as it entertains with equal parts elegance and island ease. At the center of the home, a newly updated kitchen anchors daily life. Sleek finishes, thoughtful design, and an intuitive flow make it ideal for quiet mornings or lively evenings with friends with impact glass sliders that open to the luxurious heated pool & spa. Four true bedrooms offer flexibility rarely found in this location. Perfect for full-time living, guests, or a dedicated home office. Three renovated designer bathrooms complete the experience with clean lines and a calm, spa-like feel. Lush, private, and centered around an extraordinary oversized pool, the outdoor space feels like a hidden resort designed for sun-soaked afternoons, evening swims, and unforgettable entertaining. World-class waterfront dining, marinas, galleries, and the vibrant energy of the Seaport are all moments from your door offering the quintessential Key West lifestyle without sacrificing peace or privacy. This is Old Town, elevated. A rare fusion of modern comfort, generous space, and timeless Key West allure crafted for those who want it all. Schedule your private showing today!

4 Beds ⋅ 3 Baths ⋅ 618172 MLS

1015 Eaton Street, the art of island elegance, where historic soul meets modern sophistication. Four bedrooms. Updated baths. A new kitchen. Natural light everywhere. And a big, resort-style pool; a true rarity in Old Town! Positioned in the coveted heart of Old Key West, just steps from the Historic Seaport, 1015 Eaton Street is more than a home, it's a statement. A refined yet relaxed retreat that delivers space, style, and privacy in one of the most walkable neighborhoods in Key West. The home opens in a wash of natural light, with a crisp, effortless aesthetic that is polished and inviting. Living spaces connect seamlessly, creating a layout that lives as well as it entertains with equal parts elegance and island ease. At the center of the home, a newly updated kitchen anchors daily life. Sleek finishes, thoughtful design, and an intuitive flow make it ideal for quiet mornings or lively evenings with friends with impact glass sliders that open to the luxurious heated pool & spa. Four true bedrooms offer flexibility rarely found in this location. Perfect for full-time living, guests, or a dedicated home office. Three renovated designer bathrooms complete the experience with clean lines and a calm, spa-like feel. Lush, private, and centered around an extraordinary oversized pool, the outdoor space feels like a hidden resort designed for sun-soaked afternoons, evening swims, and unforgettable entertaining. World-class waterfront dining, marinas, galleries, and the vibrant energy of the Seaport are all moments from your door offering the quintessential Key West lifestyle without sacrificing peace or privacy. This is Old Town, elevated. A rare fusion of modern comfort, generous space, and timeless Key West allure crafted for those who want it all. Schedule your private showing today!

1015 Eaton St, Key West

$1,875,000

This is the one you've been waiting for! Unlike any other 2 bed listing available in Casa Caselles, this exceptional oceanfront home has been completely reimagined from the concrete up—over $500,000 in premium upgrades make it the standout unit in this exclusive 19-home gated community. Price reduced by $100,000 for a swift sale—don't miss out! This stunning three-story concrete residence features 2 bedrooms, 3 full baths, and unmatched Atlantic Ocean views from every level. Enjoy four private balconies, a vaulted-ceiling living area, and a serene primary suite—all designed with luxurious, coastal living in mind. Every detail has been upgraded: impact windows & doors, new framing, electrical, plumbing, insulation, and soundproofing—bringing you peace of mind and modern efficiency. Designer touches include LED recessed lighting, whole-home surround sound with outdoor speakers, and custom stainless cable stair railings.The gourmet kitchen features granite counters, custom cabinetry, stainless steel KitchenAid appliances, and a wine cooler—perfect for entertaining. Spa-style bathrooms offer floor-to-ceiling tile, an oversized soaking tub, rainfall shower, and premium fixtures. Step outside to an outdoor entertainment space with a TV, bar and hot tub. A lush, low-maintenance backyard provides privacy, while a large storage room with built-ins keeps everything organized. Casa Caselles offers a resort-style beachfront pool, direct access to nature preserves, and a peaceful, owner-occupied environment with no rentals allowed—perfect for those seeking tranquility and exclusivity. Skip the renovations—move in and start living the Florida Keys lifestyle today. Schedule your private tour now and experience the best value in the community! Direct Ocean Views - Views - Views!! One owner is a licensed Florida Realtor, not the listing agent. Check out the video https://tinyurl.com/5n7xdn6s and 3D Floorplan for layout.

2 Beds ⋅ 3 Baths ⋅ 614182 MLS

This is the one you've been waiting for! Unlike any other 2 bed listing available in Casa Caselles, this exceptional oceanfront home has been completely reimagined from the concrete up—over $500,000 in premium upgrades make it the standout unit in this exclusive 19-home gated community. Price reduced by $100,000 for a swift sale—don't miss out! This stunning three-story concrete residence features 2 bedrooms, 3 full baths, and unmatched Atlantic Ocean views from every level. Enjoy four private balconies, a vaulted-ceiling living area, and a serene primary suite—all designed with luxurious, coastal living in mind. Every detail has been upgraded: impact windows & doors, new framing, electrical, plumbing, insulation, and soundproofing—bringing you peace of mind and modern efficiency. Designer touches include LED recessed lighting, whole-home surround sound with outdoor speakers, and custom stainless cable stair railings.The gourmet kitchen features granite counters, custom cabinetry, stainless steel KitchenAid appliances, and a wine cooler—perfect for entertaining. Spa-style bathrooms offer floor-to-ceiling tile, an oversized soaking tub, rainfall shower, and premium fixtures. Step outside to an outdoor entertainment space with a TV, bar and hot tub. A lush, low-maintenance backyard provides privacy, while a large storage room with built-ins keeps everything organized. Casa Caselles offers a resort-style beachfront pool, direct access to nature preserves, and a peaceful, owner-occupied environment with no rentals allowed—perfect for those seeking tranquility and exclusivity. Skip the renovations—move in and start living the Florida Keys lifestyle today. Schedule your private tour now and experience the best value in the community! Direct Ocean Views - Views - Views!! One owner is a licensed Florida Realtor, not the listing agent. Check out the video https://tinyurl.com/5n7xdn6s and 3D Floorplan for layout.

1616 Atlantic Blvd Unit 6, Key West

$1,875,000

Midtown West Retreat - Elevated Island Elegance with Pool & Privacy Discover island living at its finest in this elevated TURNKEY 3BD/3BA single-family home, perfectly positioned in the desirable Midtown West neighborhood. Built in 2014, the home offers a smart layout with one bedroom and full bath on the main level—ideal for guests or flexible living—and two upstairs bedrooms, each with its own en suite bath and treetop view porches. The light-filled open floor plan features a beautifully updated kitchen with granite countertops and freshly painted interiors. Designed for comfort and built to last, the home features plentiful storage and includes impact-rated doors and windows, Hardie board siding, a metal roof, and central A/C. Step outside to your private tropical oasis with lush foliage. An expansive composite deck surrounds the heated pool, offering plenty of space for outdoor dining and lounging. Additional highlights include off-street parking, two levels of thoughtfully designed living space, and a welcoming neighborhood vibe—just minutes from beaches, parks, the pier, and Key West's best dining and entertainment. Move-in ready and made to last—experience effortless island living today.

3 Beds ⋅ 3 Baths ⋅ 615856 MLS

Midtown West Retreat - Elevated Island Elegance with Pool & Privacy Discover island living at its finest in this elevated TURNKEY 3BD/3BA single-family home, perfectly positioned in the desirable Midtown West neighborhood. Built in 2014, the home offers a smart layout with one bedroom and full bath on the main level—ideal for guests or flexible living—and two upstairs bedrooms, each with its own en suite bath and treetop view porches. The light-filled open floor plan features a beautifully updated kitchen with granite countertops and freshly painted interiors. Designed for comfort and built to last, the home features plentiful storage and includes impact-rated doors and windows, Hardie board siding, a metal roof, and central A/C. Step outside to your private tropical oasis with lush foliage. An expansive composite deck surrounds the heated pool, offering plenty of space for outdoor dining and lounging. Additional highlights include off-street parking, two levels of thoughtfully designed living space, and a welcoming neighborhood vibe—just minutes from beaches, parks, the pier, and Key West's best dining and entertainment. Move-in ready and made to last—experience effortless island living today.

1311 Atlantic Dr, Key West

$1,870,000

Tucked into the heart of Midtown Key West, this striking 4 bedroom, 3 bathroom concrete home is where modern design meets island rhythm. Behind a private electric gate, you'll discover a home that feels like a quiet retreat lush landscaping, full irrigation, off street parking, and a sense of privacy that's rare and refreshing. Step inside and the tone changes... in the best way. Large windows and expansive doors invite natural light to pour in from every angle, blurring the lines between indoors and out. Three of the bedrooms open directly to outdoor spaces perfect for morning coffee, late night swims, or simply letting the island breeze drift through. The kitchen is effortlessly chic: Quartz countertops. Stainless steel appliances. Warm brass accents. Open cabinetry that feels curated and intentional. Every finish feels thoughtful. Elegant. Collected. And then there's the pool large, inviting, and designed for both sun drenched afternoons and candlelit evenings. It's the kind of space that makes gatherings feel intimate and weekends feel endless. This home carries a creative pulse. The spaces feel expressive yet refined modern yet soulful. There's a quiet rhythm to it. A sense that each room has something to say. Concrete construction for peace of mind. Privacy for tranquility. Style for inspiration. This isn't just a house it's a composition. And it plays beautifully in Key West.

4 Beds ⋅ 3 Baths ⋅ 618932 MLS

Tucked into the heart of Midtown Key West, this striking 4 bedroom, 3 bathroom concrete home is where modern design meets island rhythm. Behind a private electric gate, you'll discover a home that feels like a quiet retreat lush landscaping, full irrigation, off street parking, and a sense of privacy that's rare and refreshing. Step inside and the tone changes... in the best way. Large windows and expansive doors invite natural light to pour in from every angle, blurring the lines between indoors and out. Three of the bedrooms open directly to outdoor spaces perfect for morning coffee, late night swims, or simply letting the island breeze drift through. The kitchen is effortlessly chic: Quartz countertops. Stainless steel appliances. Warm brass accents. Open cabinetry that feels curated and intentional. Every finish feels thoughtful. Elegant. Collected. And then there's the pool large, inviting, and designed for both sun drenched afternoons and candlelit evenings. It's the kind of space that makes gatherings feel intimate and weekends feel endless. This home carries a creative pulse. The spaces feel expressive yet refined modern yet soulful. There's a quiet rhythm to it. A sense that each room has something to say. Concrete construction for peace of mind. Privacy for tranquility. Style for inspiration. This isn't just a house it's a composition. And it plays beautifully in Key West.

1708 Laird St, Key West

$1,850,000

FOR STATISTICAL PURPOSES ONLY

3 Beds ⋅ 2 Baths ⋅ 619009 MLS

FOR STATISTICAL PURPOSES ONLY

117 Key Haven, Key West

$1,850,000

Located in the coveted gated community of Truman Annex, this impeccably styled 2-bedroom, 2.5-bath single family home blends refined coastal elegance with effortless Old Town living, just steps from Duval Street and the Truman Waterfront. A private entrance opens to a turnkey interior highlighted by Serena & Lily accents and an airy open floor plan. The chef's kitchen boasts Bosch stainless-steel appliances, an induction range, farmhouse sink, and a waterfall-edge peninsula with bar seating. Flowing seamlessly from the kitchen, the dining and living areas offer striking furnishings, a large wall-mounted TV, and ample space for entertaining. A convenient first floor powder room completes the main level. Two sets of French doors lead to a fully fenced patio designed for al-fresco dining and relaxation. There is a small front and side yard, perfect for growing flowers, herbs or whatever makes your green thumb happy. Both upstairs bedrooms feature king beds and serene finishes. The primary suite opens through French doors to a covered balcony to capture the island breeze, while the spa-style ensuite offers dual sinks, waterfall faucets, and a beautifully tiled walk-in shower. The second bedroom includes generous closet space and access to a stylish hall bath with a walk-in shower. Enjoy a private paver patio with seating and a grill, or stroll over to the heated community pool with lounge chairs, shaded tables, and restrooms. A dedicated parking space sits just steps from the front door. Only blocks from world-class dining, shopping, and entertainment. This property is offered fully furnished, holds a Truman Annex transient license, and includes future rental bookings through the end of 2025. Ideal as a full-time residence, vacation getaway, or investment property.

2 Beds ⋅ 3 Baths ⋅ 616543 MLS

Located in the coveted gated community of Truman Annex, this impeccably styled 2-bedroom, 2.5-bath single family home blends refined coastal elegance with effortless Old Town living, just steps from Duval Street and the Truman Waterfront. A private entrance opens to a turnkey interior highlighted by Serena & Lily accents and an airy open floor plan. The chef's kitchen boasts Bosch stainless-steel appliances, an induction range, farmhouse sink, and a waterfall-edge peninsula with bar seating. Flowing seamlessly from the kitchen, the dining and living areas offer striking furnishings, a large wall-mounted TV, and ample space for entertaining. A convenient first floor powder room completes the main level. Two sets of French doors lead to a fully fenced patio designed for al-fresco dining and relaxation. There is a small front and side yard, perfect for growing flowers, herbs or whatever makes your green thumb happy. Both upstairs bedrooms feature king beds and serene finishes. The primary suite opens through French doors to a covered balcony to capture the island breeze, while the spa-style ensuite offers dual sinks, waterfall faucets, and a beautifully tiled walk-in shower. The second bedroom includes generous closet space and access to a stylish hall bath with a walk-in shower. Enjoy a private paver patio with seating and a grill, or stroll over to the heated community pool with lounge chairs, shaded tables, and restrooms. A dedicated parking space sits just steps from the front door. Only blocks from world-class dining, shopping, and entertainment. This property is offered fully furnished, holds a Truman Annex transient license, and includes future rental bookings through the end of 2025. Ideal as a full-time residence, vacation getaway, or investment property.

216 Fleming St, Key West

$1,850,000

Located in the heart of the Seaport Historic District, on two lots, this charming Conch home features a 2-bedroom main residence and a separate 1-bedroom guest cottage. The property offers exceptional outdoor living, highlighted by a large L-shaped, recently resurfaced heated pool and spa, surrounded by brick and wood decking. Inside, painted Dade County Pine accent walls add authentic character, while the marble-appointed bathrooms elevate the home's appeal. The spacious primary suite offers flexibility, with the option to be located either upstairs or in the downstairs bedroom. The kitchen and living area feature bar-top seating and a cozy cove dining space, flanked by French doors that open to the lush, tropical outdoor setting. The owners have completed extensive due diligence, including updated plumbing, electrical systems, and water heaters. The property offers off-street bricked parking.

3 Beds ⋅ 3 Baths ⋅ 618463 MLS

Located in the heart of the Seaport Historic District, on two lots, this charming Conch home features a 2-bedroom main residence and a separate 1-bedroom guest cottage. The property offers exceptional outdoor living, highlighted by a large L-shaped, recently resurfaced heated pool and spa, surrounded by brick and wood decking. Inside, painted Dade County Pine accent walls add authentic character, while the marble-appointed bathrooms elevate the home's appeal. The spacious primary suite offers flexibility, with the option to be located either upstairs or in the downstairs bedroom. The kitchen and living area feature bar-top seating and a cozy cove dining space, flanked by French doors that open to the lush, tropical outdoor setting. The owners have completed extensive due diligence, including updated plumbing, electrical systems, and water heaters. The property offers off-street bricked parking.

1110 Elgin Ln, Key West

$1,825,000

Discover an unrivaled Key West opportunity. If a third floor were added to this home, this property would offer ocean views that are truly one-of-a-kind for this island. This generously sized 7,775-square-foot lot provides a rare canvas for your architectural vision, delivering potential for a third floor or additional wings to capture even more panoramic ocean vistas while preserving the existing home's privacy and outdoor space. This 5 Bed 3 bath property stands apart with its dramatic ocean breezes and tropical ambiance, inviting a lifestyle of year-round outdoor living and sophisticated entertaining. A private driveway accommodates up to four cars. The oversized lot could accommodate an RV, large boat, or future expansions without compromising the current residence. The crown jewel of outdoor living is one of Key West's largest pools, complemented by an overflow spa and a tropical tiki hut that sets the stage for watching Sunday games, sunset gatherings, or simple tropical solace. Adjacent to the main residence sits a legally attached apartment, a versatile guest suite or in-law unit that also holds strong potential as a revenue stream, providing immediate income diversification as you plan further enhancements. Inside, the home presents a substantial footprint ripe for reimagining, with room to optimize layouts to maximize living space and ocean views. The attached apartment enhances the property's appeal by offering flexible guest accommodations or a dedicated income source while you pursue expansions. The property's footprint and scope are especially attractive to developers or buyers with a vision, enabling a second master suite, a separate guest house, or a thoughtfully integrated addition that complements the lush tropical landscaping and pool complex. The outdoor oasis is framed by tropical landscaping that creates lush privacy and a resort-like ambiance.

5 Beds ⋅ 3 Baths ⋅ 617775 MLS

Discover an unrivaled Key West opportunity. If a third floor were added to this home, this property would offer ocean views that are truly one-of-a-kind for this island. This generously sized 7,775-square-foot lot provides a rare canvas for your architectural vision, delivering potential for a third floor or additional wings to capture even more panoramic ocean vistas while preserving the existing home's privacy and outdoor space. This 5 Bed 3 bath property stands apart with its dramatic ocean breezes and tropical ambiance, inviting a lifestyle of year-round outdoor living and sophisticated entertaining. A private driveway accommodates up to four cars. The oversized lot could accommodate an RV, large boat, or future expansions without compromising the current residence. The crown jewel of outdoor living is one of Key West's largest pools, complemented by an overflow spa and a tropical tiki hut that sets the stage for watching Sunday games, sunset gatherings, or simple tropical solace. Adjacent to the main residence sits a legally attached apartment, a versatile guest suite or in-law unit that also holds strong potential as a revenue stream, providing immediate income diversification as you plan further enhancements. Inside, the home presents a substantial footprint ripe for reimagining, with room to optimize layouts to maximize living space and ocean views. The attached apartment enhances the property's appeal by offering flexible guest accommodations or a dedicated income source while you pursue expansions. The property's footprint and scope are especially attractive to developers or buyers with a vision, enabling a second master suite, a separate guest house, or a thoughtfully integrated addition that complements the lush tropical landscaping and pool complex. The outdoor oasis is framed by tropical landscaping that creates lush privacy and a resort-like ambiance.

1626 Sirugo Ave, Key West