Divider
Content Divider
Total Listings 281
Order By:

$3,399,000
Key West
George W Nichols Subdivision   - MM: 1.00
4 Bed, 4 Baths, 2,650 SqFt Days Listed: 152
-5.45% ($196,000) 3 Price Changes : Last Change 17 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Nestled within the sought-after Casa Marina neighborhood of Key West, this recently renovated home is a true tropical paradise. With 4 spacious bedrooms and 4.5 bathrooms, each offering its own en-suite for added comfort and luxury, this residence exudes both elegance and functionality. Step inside to discover a light-filled living area adorned with high ceilings, tasteful finishes and art work form local artist, creating an inviting atmosphere for both everyday living and entertaining. The gourmet kitchen is a chefs delight, featuring top-of-the-line appliances and sleek countertops that make preparing meals a breeze. Retreat to the lavish master suite, complete with a spa-like bathroom and ample closet space for all your storage needs. The remaining bedrooms are equally as impressive, offering cozy retreats for family members or guests. Outdoor living is a dream at this property, with a private pool beckoning for refreshing dips on sunny days. A charming cottage provides additional accommodation options, while multiple sitting areas dotted throughout the lush landscaping offer serene spots for relaxation or socializing.Combining modern amenities with classic Key West charm, this home is the epitome of luxury living in one of the islands most prestigious neighborhoods. Whether you seek a serene sanctuary or a stylish setting for hosting gatherings, this Casa Marina gem ticks all the boxes.

$3,398,000
Key West
Vista Del Mar   - MM: 4.00
4 Bed, 4 Baths, 2,426 SqFt Days Listed: 162
-2.89% ($101,000) 2 Price Changes : Last Change 34 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift80ft.Concre

Price reduced on this tranquil oasis with an unparalleled waterfront experience in one of the most coveted locations in Key West. where every day feels like a vacation! Located on the prestigious Riviera Canal, this one-of-a-kind four-bedroom, two-bath haven is more than just a home--its a boaters dream, a sunseekers paradise, and the ultimate in indoor-outdoor luxury living.Now offered fully furnished!Imagine waking up each morning in the heart of this island gem, with 80 feet of wide canal frontage just outside your door, complete with a 20,000 lb boat lift and davit ready for your larger vessel. Whether youre setting sail for a day on the water or simply soaking up the tropical vibes, this home puts you right where the action is.The split floor plan gives everyone their own space to unwind, while the open-concept living area beckons you to gather and celebrate the good life. With wall-to-wall sliding glass impact doors and travertine floors throughout, your living space seamlessly merges with the outdoors, bringing in natural light and the gentle breezes. Step into your own private oasis! A sparkling pool, surrounded by meticulously maintained landscaping, is the perfect spot for a lazy afternoon dip. Prefer a sunset barbecue? Your covered outdoor dining and lounge area sits on sleek travertine floors, with plenty of space to relax rain or shine.The kitchen is a showstopper, featuring quartz countertops, custom cabinetry, and stainless-steel appliances, perfect for whipping up fresh seafood feasts or hosting cocktails at the bar with a view of the pool. The primary bedroom is the ultimate retreat, with its own seating area and French doors that open right onto the pool deck. Additional features include a whole-house Generac generator, impact and soundproof windows and doors throughout, and a gated circular driveway that offers complete privacy.

$3,395,000
Key West
Old Town Unrecord   - MM: 1.00
4 Bed, 4 Baths, 2,488 SqFt Days Listed: 147
-14.05% ($555,000) 4 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Exquisite Key West Retreat in Truman Annex! Experience the best of Key West with this luxurious retreat in the exclusive gated community of Truman Annex. This Caribbean and British Colonial-inspired home blends sophistication and comfort, making it ideal as an upscale vacation home or investment with rental potential. The transient license allows weekly rentals. The residence spans three levels with 4 bedrooms, 3.5 baths, and high-end features, offering an oasis of elegance in the heart of Key WestStep inside and be in awe with the light-filled open floor plan where tall ceilings and plantation shutters highlight the living, dining and updated kitchen with quartz countertops, a breakfast bar, and premium finishes. The dining area features a stunning shell chandelier, and French doors open to a private back patio with lush landscaping, perfect for entertaining or unwinding under the stars. On the second floor, the primary suite exudes luxury with reeded wallpaper, seagrass wall-to-wall carpet, and a spa-like ensuite bath with gold fixtures, double vanities, and abundant natural light. A 2nd bedroom offers style and comfort, with a picturesque window in the separate bath. A stacked washer and dryer are located on the 2nd floor. The upper level provides privacy for guests with two additional bedrooms and a full shared bath. Throughout, the home showcases coastal sophistication with wood plank vinyl flooring, seagrass carpet in the bedrooms, reeded colonial-style wallpaper, and tasteful touches like gold bathroom fixtures and glass shower doors, embodying refined Key West charm. Enjoy a shared community pool, assigned covered parking, and walkable access to Duval Street, Mallory Squares sunset celebrations, Fort Zachary Taylor State Park, and Truman Waterfront Park. Whether a personal retreat or a smart investment, this property combines historic allure with modern luxury, providing an unparalleled Key West lifestyle. Video tour https://tinyurl.com/102-Admirals

$3,350,000
Key West
Old Town Unlisted   - MM: 1.00
5 Bed, 5 Baths, 2,550 SqFt Days Listed: 56
-9.46% ($350,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: Other Dockage

A rare opportunity to purchase a historically preserved Key West home! Welcome to 708 William Street, a unique HFKF Preservation Star Key West property that has been a cherished family home for 40 years. This 1880 residence offers a unique blend of historic charm and contemporary Key West living, making it a sanctuary for those who appreciate timeless elegance and modern comfort. The main house, with large rooms adorned with Dade County pine walls and high ceilings, is a testament to the award winning restoration done by local craftsmen. Attached to the main house is a studio apartment. Originally part of the main house this can easily be return as a grand bedroom suit. The property also features a detached one-bedroom cottage. This home is unique in the Key West market. It has been meticulously preserved in a near museum home state. The rooms are large and the ceilings high. The main house totals 2,200 sqft including the studio apartment space. The huge front wrap around porch preserves subtle gingerbread styling. Even the pool has historic roots as it originally was the water cistern. As part of an estate, this home will be sold. Dont miss out on this once in a decade opportunity.

$3,350,000
Key West
Monroe Investement Co Subdivi   - MM: 2.00
5 Bed, 5 Baths, 2,500 SqFt Days Listed: 35
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Discover an incredible opportunity in the heart of Key West! This 7,500 sq. ft. lot is cleared, ready for the new construction of this single-family home. Planned for a 5 bed, 5 1/2 bath, pool home. Buyer still has time to choose design materials and possible floor plan changes . Soaring ceilings on both levels, crown molding, and a full ensuite bath in every bedroom. The open-concept first floor is perfect for entertaining, with a spacious kitchen boasting a large island, white 42 cabinetry, and high-end appliances. The living area flows seamlessly into the kitchen and beautifully landscaped backyard with a pool w/hot tub. The second-floor laundry room includes ample cabinet storage, and the home is raised on piers above flood zone, with several private parking spaces. The first-floor primary suite features a walk-in closet and an ensuite with a 5 shower, double sinks, and a separate whirlpool tub. Built to the highest wind load and flood standards, this home is both a sanctuary and a fortress. Contact agent about this New Build home! Photos are not exact and just an estimated of the new build.

$3,311,000
Key West
Investment Co Subdivision   - MM: 1.00
4 Bed, 4 Baths, 2,928 SqFt Days Listed: 272
-16.18% ($639,000) 3 Price Changes : Last Change 5 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Welcome to your dream oasis in the heart of Key West! This stunning 4-bedroom, 4-bathroom home embodies luxury and entertainment, offering an unparalleled lifestyle in a prime, central location on the island.Stepping through Brazilian-Walnut Entry doors into this exquisitely updated residence, you are captivated by the lush courtyard and lured over the Pond bridge to the sounds of cascading waterfalls. Massive Custom-made entry leads to an expansive grand foyer and open-concept living area, perfect for hosting gatherings or relaxing in style. The gourmet kitchen is a chefs delight, featuring top-of-the-line Viking gas-fueled appliances, custom cabinetry, and a large island with seating for casual dining. Adjacent to the kitchen, the elegant dining area features a unique white slate gas fireplace and flows seamlessly to the spacious living room, creating an ideal space for entertaining guests.Each of the four bedrooms is a private retreat, boasting generous proportions, and high-end finishes and furnishings. The primary suite is a true sanctuary, offering a spa-like bathroom with a soaking tub, walk-in shower, and dual vanities, as well as 2 walk-in closets.Outside, the home is a paradise for outdoor living. The meticulously landscaped backyard features a sparkling pool, joined by a spacious patio with plenty of room for lounging and alfresco dining. The covered terrace and outdoor kitchen are perfect for year-round entertaining, while the tropical lounging lawn provides a serene sunbathing escape.This luxurious home also includes modern amenities such as a state-of-the-art home automation system, new energy-efficient HVAC, and ample storage with TWO garages. With its unbeatable location in the heart of Key West, youll enjoy easy access to the islands vibrant nightlife, world-class dining, and stunning beaches.Offered completely furnished, you will experience the epitome of luxury living in this exceptional Key West home.

$3,295,000
Key West
Key West Investment Co Subdiv   - MM: 1.00
3 Bed, 3 Baths, 2,100 SqFt Days Listed: 109
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Located in Old Town Key West, and on one of the most sought after tranquil lanes, sits this perfectly updated home in the X zone. Upon entering, the foyer seamlessly flows into an open-concept living room and kitchen. Youre welcomed by a breathtaking cathedral ceiling that enhances the sense of space, while large pocket doors draw your gaze to the outdoors. An expansive lanai extends the living space, featuring a dedicated dining area and alfresco kitchen. This home offers three spacious en suite bedrooms, each thoughtfully designed for comfort and privacy. The Sea Grass green kitchen features a glass backsplash, quartz countertops, and top of the line appliances including a Wolf Range. The open loft space, currently furnished with twin beds, can easily be transformed into a home office. Tucked away in the loft is a hidden, generously sized closet, perfect for additional storage. The master suite, located just off the pool, boasts elegant built-in cabinetry. A hallway leads to the laundry facility, and two additional en suite bedrooms, one of which has its own private porch. The exterior of this home is truly exceptional, featuring IPE decking that surrounds a stunning 20 x 10 pool with a sleek tiled water feature, an outdoor shower, and tropical landscaping with a privacy fence. Most importantly, there is an antique, bricked driveway enough for two cars.

$3,295,000
Key West
Old Town Unlisted   - MM: 1.00
4 Bed, 4 Baths, 1,801 SqFt Days Listed: 80
-12.13% ($455,000) 3 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Welcome to this newly renovated architectural gem in Old Town Key West. This historic home has been meticulously renovated to blend timeless charm with modern sophistication. The main house offers three bedrooms, 3.5 luxurious baths, all illuminated by natural light pouring through impact-resistant doors and windows. Throughout, the warmth of oak floors complements the clean, contemporary lines of the space. The gourmet kitchen, fitted with Bosch stainless steel appliances, is a dream for culinary enthusiasts, while the open-concept design makes it perfect for entertaining. Step outside to your private oasis, where a stunning waterfall pool is the centerpiece of a lushly landscaped garden. The outdoor kitchen and spacious dining area are perfect for hosting al fresco dinners, making the most of the tropical Key West climate. For guests, a separate one-bedroom, one-bath guest house ensures privacy and comfort. Additional features include off-street parking and an electric vehicle charging station. Just two blocks away, the iconic Duval Street invites you to explore world-class dining, art galleries, and nightlife, with historic stops like Sloppy Joes. A two-block stroll west brings you to the literary haven of the Ernest Hemingway Home and Museum, while the Key West Lighthouse, just one block farther, offers panoramic island views.For beachgoers, the tranquil shores of Fort Zachary Taylor Historic State Park await, only five blocks away. History lovers will appreciate being just*five blocks from the Truman Little White House, a symbol of presidential retreat. Each evening, Mallory Square, also five block away, offers a festive sunset celebration, a must-see experience. For waterfront dining and sailing excursions, the Key West Historic Seaport is within the same easy reach. 907 Whitehead Street isnt just a home--its a luxurious retreat in the heart of Key Wests most coveted neighborhood, offering a blend of history, elegance, and walkable island living.

$3,295,000
Key West
Martello Towers   - MM: 1.00
4 Bed, 4 Baths, 2,147 SqFt Days Listed: 46
-2.95% ($100,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

1522 Georgia St., a stunning retreat that captures the iconic charm of Key West with a modern twist, offering a lifestyle of unparalleled luxury. Located one block from the islands beaches and Casa Marina District, this newly built residence is a perfect combination of timeless island elegance & contemporary sophistication.Four exceptional bedrooms, each a private sanctuary of comfort and style, boast spa-like en-suite bathrooms and spacious walk-in closets. Wrapped in a palette of serene, calming hues, these retreats are adorned with elegant Eastern Accent Linens, gorgeous window treatments and handcrafted wood shutters that invite the Island breeze. Stunning wallpaper, worthy of an Architectural Digest spread, adds a touch of artistry to every space, creating bedrooms that feel less like rooms and more like luxurious personal havens.Open floor plan where indoor and outdoor living blend effortlessly, creating a space for relaxation and entertaining alike. The gourmet kitchen, elegant dining area and inviting living rooms flow together with ease, all offering panoramic views of the majestic saltwater pool. Outside a serene waterfall cascades into the crystal-clear waters, while the sun drenched patio, glass railing and mature landscaping provide a private, resort-like escape - a true oasis where every days feels like a vacation.The Kitchen is nothing short of breathtaking, a masterpiece of design and function where every details has been meticulously curated. The designers eye for perfection is evident in the harmonious blend of colors, textures and finishes, all layered with stunning precision. At its heart, a spacious, statement-making Island invites both conversation and culinary creativity. Overhead, brass-covered light fixtures cast a warm inviting glow, perfectly complementing the gorgeous artful backsplash that adds that final touch.Additional features include, impact windows/patio doors, & off street parking.

$3,275,000
Key West
Webb Realty Co Subdivision   - MM: 1.00
3 Bed, 3 Baths, 3,049 SqFt Days Listed: 355
-9.00% ($324,000) 1 Price Change : Last Change 68 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Wonderful 3BD/3.5BA home with just over 3,000 sf of living space situated in the desirable Casa Marina neighborhood. Centrally located & just a short walk to Duval Street, the beaches, museums, galleries & many of Key West fine dining that it has to offer. With a spacious open floor plan & lots of windows & French doors throughout allow for plenty of natural light to fill this spectacular home. The master bathroom was recently renovated, a whole home generator was installed, a commercial on demand hot water heater was installed, new copper gutters and downspouts, newer Central A/C systems, downstairs interior was re-painted, composite decking on the exterior & a new carport canopy are all just some of the many great features this property has to offer. The kitchen has stainless appliances and the flooring throughout the downstairs & patio was replaced. Located just off the kitchen through the French doors you will find a large loggia which is an incredible space for your outdoor living & dining room where you can host family or friends comfortably. Upstairs you will find the master bedroom w/ ensuite bath and the 2 additional guest bedrooms. Off the master bedroom is a gorgeous & private sundeck which also has access to the pool deck via a spiral staircase. Additionally you can find stained glass throughout the home and cathedral ceilings. Property is located in the X Flood Zone and is completely fenced adding for that extra privacy. Potential for a great monthly vacation rental!

$3,225,000
Key West
Monroe Investement Co Subdivi   - MM: 2.00
5 Bed, 5 Baths, 2,711 SqFt Days Listed: 119
-2.27% ($75,000) 2 Price Changes : Last Change 8 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Stately Key West home has undergone a stunning renovation but maintains classic Keys charm with a beautiful wood staircase, stained glass window and transom, Dade County pine walls, and wraparound porches on both levels. Centrally located in Key West this home is the perfect island residence with POOL! The main level offers plenty of room for entertaining with large spaces for conversation, dining, games, cooking, and more. Spacious chefs kitchen with breakfast bar and natural design elements throughout. Kitchen flows to the sitting area with designer bar space and wall of sliding glass doors opening to the pool and a pass-through window to covered porch area. Main level offers one bedroom with outdoor access and a full bath. The upper level boasts four additional bedrooms including primary suite. The primary bedroom is a resort like retreat with elegant spa tub, large walk-in shower with multi-jets, rain forest shower, linear drain and walk-in closet. The primary also features access to deck space perfect for morning coffee. Bedroom with en suite bath and deck access. The other upstairs two bedrooms share an en suite full bath. Perfect tree top views from upstairs on the wraparound porch. The third level is currently a music room and offers access to the widows walk for top of the island views! Lovely private outdoor areas with mature tropical landscape. Pool area with tiki hut offers covered space for reading or relaxing. Garage has room for parking or storing your island water toys. Laundry room on second floor and bonus washer & dryer in garage. Elevator to each floor. Central AC. This is the perfect island home!

$3,150,000
Key West
New Town Unrecord   - MM: 3.00
5 Bed, 5 Baths, 3,105 SqFt Days Listed: 7
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Expect the unexpected at 1400 1st Street, an exquisite retreat where unmatched craftsmanship meets island luxury. This custom-built 5-bedroom, 4-bathroom home offers a perfect balance of sophistication and quality. From the moment you step inside, the rich Brazilian cherry floors guide you through this elegant home, exuding warmth and elegance The chefs kitchen is a culinary dream, featuring polished granite countertops and top-of-the-line stainless steel appliances, including a Sub-Zero refrigerator and a six-burner Viking gas range. Custom tile work adorns each bathroom, elevating every space with exceptional detail.Soaring ceilings enhance the open-concept design, filling the home with natural light. Every poolside bedroom boasts its own private balcony, offering stunning views of the tropical surroundings. The expansive primary suite is a true retreat, featuring a private beverage center for added luxury and convenience. The spa-inspired primary bath includes a soaking tub and rain shower, creating an intimate oasis within your own home.Designed for effortless entertaining, the custom bar area is a true highlight. Equipped with a wine cooler, sink, and ice maker, its ideal for hosting memorable gatherings. Step outside into your private tropical oasis, where mature trees create a sense of serenity and two cascading waterfalls frame the serene swimming lagoon. A beautiful dining gazebo spans the water, perfect for outdoor dining and entertaining. Lush landscaping surrounds the entire property, providing privacy and an idyllic backdrop for relaxation.This home also includes a rare two-car garage, with secure parking for up to three additional vehicles or watercraft, offering unparalleled convenience. With its seamless blend of design, luxury, and functionality, this home is a true Key West gem.Just moments from the islands beaches, marinas, dining, and shopping, this property offers both tranquility and access to all that Key West has to offer!

$3,150,000
Key West
Webb Realty Co Subdivision   - MM: 1.00
4 Bed, 4 Baths, 2,880 SqFt Days Listed: 99
-4.40% ($145,000) 1 Price Change : Last Change 16 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Located in the highly regarded Casa Marina neighborhood, this exceptional property offers a unique opportunity to own a piece of Key West history. Ernest Hemingway the iconic literary figure once called this house his Winter retreat during 1928 -1929, where he penned the timeless classic, A FAREWELL TO ARMS. This sprawling single story property spans an impressive 8100 square feet, occupying a prominent corner lot, with a reimagined interior floor-plan. Constructed with white-painted Savannah brick over a wood frame, this residence exudes classic charm with a modern twist. Tall ceilings and a welcoming fireplace create an inviting atmosphere. Sliding glass doors seamlessly connect the interior to the outdoor patio, allowing for a harmonious blend of indoor and outdoor living spaces. The outdoor space is a tropical paradise, complete with a heated pool and soothing water feature. The main house features 3 bedrooms, 2 bathrooms, and a laundry area. Two of the bedrooms share a bathroom, while the primary suite offers a generously sized bathroom with a bath tub, double sinks, and an indoor and an outdoor shower. Enjoy the airy ambiance of the open floor plan, with a spacious living room and dining area that together span over approximately 1200 square feet. The modern kitchen is well-appointed, with easy access to the pool area and the charming conch-style 1/1 guesthouse. The main house has a semi-circular driveway and can accommodate 3-4 cars. The guesthouse also includes its own entrance on Walton Street and an off-street parking space.

$3,150,000
Key West
White & Pierce Diagram   - MM: 1.00
3 Bed, 3 Baths, 1,615 SqFt Days Listed: 71
-3.08% ($100,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Discover your dream Transient Vacation Rental in the heart of mid-town Key West! This beautifully refreshed home boasts a light and airy atmosphere and is sold fully furnished with rentals on the books and ready to go. Featuring three bedroooms, including a spacious primary suite and three baths, this property offers an inviting open living and kitchen area, highlighted by soft hues and vibrant tropical accents. Dine al fresco in the charming attached pavilion, perfect for enjoying the lush surroundings.Each bedroom provides direct access to different areas of the yard, enhancing the privacy and outdoor experience for every guest. The luxurious primary suite opens to the pool area through stunning French doors, while the primary bath features a spacious, tiled walk-in shower. The second bedroom, painted in serene green tones and decorated with inspiring Key West art, offers a tranquil retreat with two twins that may be turned into a king. The versatile third bedroom is on the opposite side of the house with remodeled bath ensuite.Nestled in a quiet residential neighborhood, this home is just a short bike ride from the beautiful beaches on the south side of the island and the vibrant Duval Street, with the Casa Marina area even closer. This home is the ultimate vacation getaway!

$3,099,000
Key West
Sunset Key   - MM: 0.00
3 Bed, 3 Baths, 1,920 SqFt Days Listed: 243
-16.13% ($596,000) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This is the ultimate living experience. You get all Historic Key West has to offer, but are tucked away on your own private island paradise. Access to Sunset Key is by the island ferry which runs 24 hours a day, but is only a 4 minute boat ride. Have all the fun you can stand in Key West, but then come home to absolute peace and quiet. Have your own Sunset Party from your covered roof top observation deck. The island has all the conveniences of a world class luxury resort, including three beaches within a minutes walk, a full service spa, golf cart parking, gourmet restaurant, tennis courts, and much more. Ample covered parking is available at discounted rates in the Opal Resort parking garage. For a truly unique and eye opening experience, call now and make an appointment for a private grand tour of the island. You will be glad you did!

$3,000,000
Key West
Prog Land Imp Co Diag   - MM: 0.00
4 Bed, 4 Baths, 2,276 SqFt Days Listed: 36
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

Experience the true essence of Tropical living in Key West with this exquisite mid-century estate, the perfect blend of a private sanctuary and a highly coveted transient license, making it a lucrative income-producing asset. Located on an expansive corner lot, this property is enveloped by lush foliage, ensuring the utmost privacy and a serene ambiance that feels worlds away yet remains just moments from the vibrant heart of Key West. As you enter through the winding brick pathways, you are greeted by mature landscaped gardens and multiple outdoor spaces designed for both relaxation and entertaining. The heart of this oasis is a stunning 35-foot heated pool accompanied by a covered pavilion, offering the ideal setting for leisurely afternoons or elegant gatherings. The main residence showcases nearly 2,000 square feet of thoughtfully designed living space, featuring a primary bedroom suite with a glass enclosure sitting area that invites natural light to cascade throughout. Two additional guest bedrooms and a spacious living/dining area open through multiple sets of French doors, seamlessly blending indoor and outdoor living. Adding to the propertys allure is a separate studio guest cottage. This flexibility allows you to enjoy a tropical getaway during your visits while maximizing rental potential from the main house offering the best of both worlds. Ideally situated just a short stroll from pristine beaches, the iconic White Street Pier, and premier tennis and pickleball courts, this estate provides an unmatched opportunity to own a private oasis in one of the most sought-after destinations.

$3,000,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 2,139 SqFt Days Listed: 4
Single Family - Contingent - Waterfront No
Side of Island: Median - Dockage: None

Introducing this beautifully renovated Eyebrow home, Winner of the Ceramic Star Award from the Historic FL Keys Foundation. An Old Town treasure that carries an inviting ambiance, instantly making you feel at ease. Lush landscaping and exterior lighting enhance the homes charming exterior. Step inside the foyer, where youll find the library on your right - A private and adaptable space with pocket doors, which could make for a productive office or an additional bedroom. To the left, the primary suite offers a walk-in closet and en-suite bath. Down the hall, youll find an additional full bath, a laundry room, and an open-concept living area that flows into a thoughtfully curated kitchen with high-end finishes - Six-burner propane stove, an expansive island, custom cabinetry (including glass-front accent lighting), a separate pantry, and french doors and pass-through windows that make for airy indoor-outdoor living. Upstairs, two guest bedrooms share a naturally lit bathroom. The expansive outdoor area features two levels--an upper terrace with a sitting area and dining space, and a lower level surrounding the pool, complete with a pool bath. Additional highlights include two off-street parking spaces with access from Canfield Lane and a whole-house generator.

$2,999,500
Key West
Mills Place   - MM: 1.00
2 Bed, 2 Baths, 1,770 SqFt Days Listed: 54
Townhouse - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Vacation rental Ocean and Harbor view unit in Truman Annex. Beautiful sunset vistas of the Atlantic and the Gulf while also overlooking the the tropical and lush grounds of Truman Waterfront Park and Truman Harbor. This residence features a large covered balcony right off the main living area with living room, dining room and kitchen. The second storys primary bedroom and bath opens out to its own private balcony. Highly desirable Old Town location in Mills Place condominiums in Truman Annex.

$2,999,000
Key West
Prog Land Imp Co Diag   - MM: 2.00
9 Bed, 9 Baths, 4,037 SqFt Days Listed: 39
Multi-Units - Contingent - Waterfront No
Side of Island: Ocean - Dockage: None

PRICED TO SELL - This is a rare and exceptional opportunity!Land is at premium in Key West, and this expansive nearly 12,000 sq. ft. lot with not one but essentially 3 houses and room to grow, is an extraordinary find. Discover a balanced blend of Key West character, mid-century charm, and modern updates with this one-of-a-kind multi family compound. This property could not be more well designed for seclusion and private entertainment. Whether youre looking for a spacious primary residence, an income-producing property, a redevelopment opportunity, or a combination of all three, this is your drawing board.Once home to a beloved local artist, this award-winning property--recognized by the Old Island Restoration Foundation--is a nostalgic tribute to its time period. The current owner has preserved and enhanced its retro artistic flair, creating a truly unique ambiance that transports you back in time.Property Highlights:✅ Three Separate units- Each with its own private access and gated tropical yard✅ Main House (4 BD | 3.5 BA) - An open combo entertainment area overlooks a resort-style outdoor space featuring a stunning collection of mature and rare plant species, creating a lush, tropical sanctuary. At its heart, a luxurious heated pool basks in the sunshine by day and transforms into a glowing oasis by night, illuminated by soft ambient lighting.✅ Second Unit (3 BD | 2 BA) - Exposed beam ceilings, skylights, and a serene outdoor shower.✅ Third Unit (2 BD | 2 BA) - A cozy retreat with an expansive patio space✅ Concrete Block Construction, Impact windows and doors for added security✅ Off-Street Parking & Endless Storage - A rare convenience in Key West✅ Only three blocks from the beach/pier and a short stroll to Old Town. This property is an entertainers dream that must be seen in person to truly understand and appreciate all it has to offer.

$2,999,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 1,620 SqFt Days Listed: 54
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

High style in a highly desirable location. Amidst the quaint lanes and the best restaurants on the island you will find this completely renovated, incredibly designed and decorated 1,620 square foot, three bedroom and three and one-half bathroom delightful Conch home. In arguably the best location in Old Town you are close enough to walk or bike to everywhere you want to go yet tucked away behind your white picket fence and in your own private sanctuary. The property is being sold turnkey-the renovations have been done, the furniture has been purchased and the closets are ready for your clothes! Finished in 2020 the home was completely rebuilt including the foundation and roof. A gorgeous pool with waterfall, impact windows, impact doors, air conditioning, Plantation shutters, Dade county pine, frosted interior doors and more were added. This thoughtfully restored home has a guest room with bath ensuite on the main living level as well as another bedroom/den/office and full bath in the hallway. The kitchen, dining and great room have a vaulted ceiling and open to a covered outdoor patio with dining area, heated pool, and the perfect place to lounge. Up the floating staircase you will find the primary bedroom with bath en-suite as well as an additional bonus space that can be used as an office, gym, or overflow sleeping quarters. There is also a laundry room with a half bath. You will love the generous rooms with vaulted ceilings, open kitchen with designer cabinets, stainless steel appliances, tile flooring, and Impact disappearing glass doors that bring the outside in. At the rear of the property on Griffin Lane is an area for parking a golf cart and bicycles. When you are not cooking in your gourmet kitchen you have Cafe Sole, Five Brothers, Bobs on Margaret, Azur, Mangia Mangia, and Date and Thyme right outside your door. As a full-time residence, vacation getaway, or investment property this one really does tick all the boxes.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 03-31-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA