Divider
Content Divider

Lower Keys Homes for Sale, Single Family Houses, MLS Home Listings

Total Listings 414
Order By:

$3,900,000
Key Haven
Key Haven 3rd Add   - MM: 5.00
4 Bed, 4 Baths, 2,057 SqFt Days Listed: 57
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Ramp,Boa

Spectacular open water Key Haven residence with stunning panoramic views of the turquoise Gulf waters located just minutes from Key West. Spanning a large spacious 15,000 sq ft. corner lot where the two wide canals meet, with over 200 linear ft. of concrete seawall, accommodating multiple boats and sea faring toys. Private boat ramp, boat lift, and excellent easy access for all your boating needs.Features 4BD/3.5BA CBS two story home, with stunning vistas of the Gulf from every room. Newly remodeled kitchen features a unique three paneled window opening to pool and ocean allowing the gorgeous Gulf Breezes to flow through the house. All new cabinets and stainless steel appliances, newly tiled floors, and three sets of impact sliders opening up the property to the enviable outdoors.Pool, Jacuzzi, and covered living pavilion are a spectacular addition to the property with new Tiki, outdoor bar, and entertaining area offering the ideal spot for the family BBQ and weekend gathering. The spacious lot offers so much flexibility for entertaining and while the vista views are spectacular, the seawall position is perfectly positioned to protect your boat.Two car garage with storage for rods and reels, off street parking for an RV, boat trailers, multiple vehicles, and a wide selection of stunning palms and tropical landscaping are just some additional features of this exquisite home. Being offered turn-key with all furnishings to ensure a seamless transition for the new owners.

$3,975,000
Key West
Tropical Bldt & Investment Co   - MM: 2.00
4 Bed, 4 Baths, 1,802 SqFt Days Listed: 458
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

If you are looking for Key West Luxury Island living at its best, then here it is 1235 Washington St. Island modernization with ultra-luxury high end finishes. This newly renovated residence is built above the current base flood elevation and designed to the latest building codes. Home features 4bedrooms/4 bathrooms of unparalleled style & sophistication. Complete with designer kitchen, build in cabinetry from Italy, quartz counter tops, and high end appliances. Home is built with CBS construction, spray foam insulation, hurricane impact windows & doors, and V-crimp metal roof which will help lower insurances and provide low maintenance. Interior has 10 ft. ceilings throughout and a grand vaulted ceiling in the living room area. Brand new salt water pool with water feature and separate pool house/guest quarters designed with carefree life style adds to the exceptional value of this amazing home. Home is furnished with new modern furniture inside and out and is available for purchase but not included in purchase price. Sit on your super beautiful front porch with tiger wood finishes and enjoy all Key West has to offer. Home is located on a 5,348 S.F. corner lot in one of the most prestigious and desirable areas of Key West. Lush tropical landscaping, irrigation, outdoor lighting, and off St. Parking completes this very desirable luxury property. Just a short distance too many of Key West fine restaurants, galleries, museums, White St. pier, & beaches. Dont miss out on this excellent opportunity to own this impressive and newly renovated luxury residence at 1235 Washington St.

$3,995,000
Cudjoe Key
Cudjoe Acres   - MM: 21.50
6 Bed, 6 Baths, 4,976 SqFt Days Listed: 775
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp80ft.

Welcome to your dream Florida Keys oasis! This stunning open water home is a luxurious waterfront retreat, offering the epitome of elegance and comfort. With 6 bedrooms and 6 bathrooms, this spacious estate is perfect for accommodating family and friends or hosting extravagant gatherings.Upon entering the property, youll be greeted by a sense of exclusivity and security, as it is gated and walled, ensuring your utmost privacy and serenity. The lush landscaping surrounding the home adds to its allure, creating a tranquil and inviting ambiance.The interior boasts an impeccable design with meticulous attention to detail. The custom kitchen is a chefs delight, featuring top-of-the-line appliances, premium finishes, and ample counter space for preparing gourmet meals. As you explore the residence, youll be captivated by the panoramic water views from every room, seamlessly blending the indoors with the breathtaking outdoors. One of the highlights of this exceptional property is its rooftop swimming pool and bar, where you can soak up the Florida sun while savoring refreshing cocktails and enjoying unobstructed vistas of the sparkling waters. Imagine entertaining guests under the stars, with the gentle ocean breeze as your companion. Additionally, this estate comes with a guest house for extended family or visitors who will be enchanted by the beauty of the Florida Keys. Sitting on over an acre of pristine Florida Keys property, this home offers an abundance of space for various outdoor activities and potential additions, should you desire to further customize your slice of paradise. As a waterfront haven, this property provides direct access to the water, allowing you to indulge in water sports, fishing, and boating whenever your heart desires. In conclusion, this exceptional Florida Keys estate combines the allure of open water living with exquisite design.

$3,999,000
Key West
Old Town Unlisted   - MM: 1.00
7 Bed, 7 Baths, 3,015 SqFt Days Listed: 10
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This property has a glamourous three bedroom, three and a half bath owners unit with private pool and hot tub, plus three lucrative long-term rentals. It is the entire Lighthouse View Condominium Association, currently inactive. Enter thru the electric gate to a bricked courtyard with parking for several cars and many bicycles and access to a covered carport. The main residence with its heated pool and hot tub is secluded in the rear with a pretty garden and brick terrace. A free-standing two story building contains a great room, splendid kitchen and half bath downstairs. Above is a bright and breezy master suite with cathedral ceilings and skylight. In addition, there are two guest cottages, each with one bedroom, one bath and a pretty front porch. On the deck between the cottages is an outdoor wet bar and there is an outdoor shower by the pool. The other apartments are in a building at the front of the property. Downstairs are two one bedroom-one bath units. Upstairs is a glamorous two bedroom-one bath with a big, wonderful deck under the trees.

$3,999,999
Key West
Key West Investment Co Subdiv   - MM: 1.00
3 Bed, 3 Baths, 2,262 SqFt Days Listed: 79
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Discover the epitome of refined Key West living in this beautifully renovated single-level home, situated in the desirable Casa Marina area. Sunlight floods the spacious interiors through oversized impact windows and doors, creating a seamless connection to the lush landscaping outside. Thoughtfully transformed into an island oasis, this home offers tranquil views of the salt generated heated pool and its cascading waterfall from the dining and living rooms. Designed for effortless entertaining, the expansive kitchen flows naturally into both the dining and living areas. Outfitted with new quartz countertops, Viking stainless-steel appliances, a 2 zone wine fridge, island & bar, the kitchen is a delight for culinary enthusiasts. Sold fully furnished, complete with new furniture and televisions, making it truly move-in ready--just bring your swimsuit and flip-flops. Other features include new designer porcelain tile floors throughout, freshly renovated bathrooms with custom vanities, in the primary suite a new soaking tub has also been added as well as custom closets. Practical amenities include a gated double carport, generator, landscape lighting, irrigation system, and full privacy walls. Freshly painted inside and out, this large 6,890sf corner property is a rare find, balancing luxury, comfort, and convenience in an idyllic location walkable to the beach & downtown.

$4,250,000
Key West
Old Town Unrecord   - MM: 1.00
6 Bed, 6 Baths, 3,171 SqFt Days Listed: 21
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Situated directly across from the iconic Ernest Hemingway House, this exceptional family compound combines the rich history of Old Town Key West with modern luxury and island charm. From the famous six-toed cats that roam next door to the vibrant energy of Duval Street just steps away, this location is as legendary as it is convenient. Spanning two addresses at 407 and 415 Olivia Street, this versatile property is situated in the X flood zone and offers four off-street parking spaces. The main house, a meticulously renovated mid-century modern gem, welcomes you with a grand entrance foyer that flows into a spacious living, dining, and media area. Perfect for entertaining, the space features a working fireplace and a 76-inch TV. The gourmet kitchen boasts solid wood cabinetry, Bosch and Thermador appliances, an induction cooktop, column fridge/freezer, wine cooler, and an impressive 13-foot quartz waterfall island. Impact sliding doors open to a stunning saltwater pool complete with a sun ledge, slide, and waterfall. Surrounded by tropical landscaping, this backyard oasis also features an outdoor shower, fully equipped kitchen, and plenty of space for entertaining. The main house offers four bedrooms, each with generous closet space and outdoor access. The primary bedroom includes a new custom walk-in closet with solid maple built-ins. Another ensuite bedroom has been transformed into a stylish home office with a built-in Murphy bed. The two additional bedrooms share an elegant bathroom featuring a luxurious soaking tub and shower. Adjacent to the main house is a charming two bedroom, two bath Conch-style cottage that provides the perfect guest retreat or mother-in-law suite. This home features a fully equipped kitchen, Dade County pine accent walls, and a tranquil outdoor space to relax under the shade of swaying palm trees. Dont miss the chance to see this unique compound that provides the perfect blend of history, luxury, and the ultimate Key West lifestyle!

$4,300,000
Key Haven
Key Haven 5th Add   - MM: 5.00
4 Bed, 4 Baths, 3,204 SqFt Days Listed: 30
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift60ft

This 4b/4.5ba luxurious home boasts Gulf of Mexico & deep canal waterfront living in Key West. It includes hurricane shutters, impact windows, metal roof with solar panels, and automated blinds. Ample parking with 2 large garages & driveway for 3 cars. 1st floor has a Chefs kitchen, a dining room perfect for hosting parties, a luxurious master suite with walk-in custom closets and the en-suite bath is a sanctuary of relaxation, with adjustable color lighting, his/hers vanity sinks on opposite walls, & full-size stacked washer/dryer with lots of storage. A half bath is also available for guests. Kitchen appliances include; induction cooktop with downdraft, D/W, Bev. cooler, convection wall oven & M/W, warming drawer & a fridge with TV. Abundant storage and appliance garages. Wood ceilings in the living room add to the charm, while the dining area has seating for 8 with a coffee/wine nook. On the 2nd floor, youll find 3 more bedrooms and a washer/dryer. One bedrm is a 2nd master with en-suite bath and large balcony overlooking the Gulf. Another bedrm is repurposed into a lounge, though it can easily be reverted back. This area shares access to a Jack n Jill bathroom equipped with his/hers sinks, connecting to the 4th bedroom featuring side-by-side closets and private porch overlooking the canal. Downstairs is an outdoor area, complete with a workshop and a full bath. Elevator runs from ground to 2nd floor. The kitchen has a sink, fridge, and gas grill. Also, an electric smoker and wood-burning pizza oven complete the outdoor cooking facilities. There are multiple gas grills. An outdoor TV swivels for viewing from the couch for 8, dining table for 6, the hot tub or a round table for 4. There is a splash pool w/ sail shade, a hot tub, shuffleboard, ping pong and outdoor wireless speakers. A private dock sits on the canal including 2 boat lifts with direct access to the Gulf and Atlantic. A fish cleaning station is on the dock, with water and electric.

$4,395,000
Key West
Monroe Investement Co Subdivi   - MM: 2.00
4 Bed, 4 Baths, 2,773 SqFt Days Listed: 107
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Inspired by a deep commitment to environmental stewardship, award-winning local architect Matthew Stratton presents his latest masterpiece at 1614 Washington. This custom home marries sustainable luxury with modern design, perfectly embodying the islands bright, eco-conscious future. Spanning 2,773 square feet, this four-bedroom, 4.5-bathroom residence exudes sophistication from the moment you arrive. Its elevated, contemporary island aesthetic is a testament to exceptional quality and craftsmanship. Setting it apart is the innovative suite of energy-saving features, including a solar grid infrastructure, Tesla energy storage batteries for uninterrupted clean energy, and ENERGY STAR(r) certified appliances. High-performance impact aluminum windows, fortified concrete block walls, spray foam insulation, and a reflective metal cool roof ensure optimal energy efficiency and comfort. An off-streel car charging station further highlights the homes green design, making eco-friendly living as seamless as it is stylish. Every detail of the home reflects a deep commitment to sustainability and craftsmanship. Environmentally friendly porcelain tile floors, quartz countertops, and custom cabinetry and wardrobes by local artisans Hansen and Bringle blend form and function beautifully. Hand-blown glass light fixtures, a backlit blue agate backsplash, and high ceilings elevate the homes refined atmosphere, while a centralized media closet ensures all electronics are conveniently organized in one user-friendly space.Outside, the lush tropical landscaping frames a two-tiered pool complete with a splash deck and waterfalls, creating an enchanting private oasis. More than just a residence, 1614 Washington is a sanctuary where sustainability and luxury harmoniously converge. This is the pinnacle of modern island living, where thoughtful design meets the future of eco-conscious luxury.

$4,500,000
Key West
Key West Fwdn Subdivision   - MM: 4.00
3 Bed, 3 Baths, 2,744 SqFt Days Listed: 44
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

3741 Eagle Avenue - A Masterpiece of Coastal Luxury This stunning 3 bedroom, 3.5 bath fully furnished residence on a generous 10,800 SF lot offers unparalleled coastal elegance at an impressive elevation of 10.5ft. The new concrete construction features an open concept with cathedral ceilings and large impact sliding doors throughout. Premium materials, high-end appliances, and thoughtful layout create both functionality and sophistication.Two en-suite primary bedrooms, both upstairs and downstairs, open to the outdoors. The property includes a fully equipped guest cottage featuring sliding doors that offer stunning views. The grounds, masterfully designed by Craig Reynolds, showcase lush tropical landscaping, covered patios all surrounding a heated/chilled pool with shelf seating and a distinctive coral rock outdoor shower which adds a luxurious touch. The garage provides 481 square foot for parking and ample storage.Security and comfort are ensured with a whole-house Generac generator, standing seam metal roof, impact windows and doors. Every detail of this turnkey residence has been executed to perfection, creating an extraordinary Keys retreat.

$4,500,000
Key West
Gg Watson Subdivision   - MM: 1.00
5 Bed, 5 Baths, 2,721 SqFt Days Listed: 6
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Luxurious Old Town Key West Oasis with separate Guest House! Nestled in the heart of Key Wests historic district, this impeccably remodeled property redefines island elegance. Situated in the coveted X Flood Zone, this home boasts an unparalleled location just steps from iconic Duval Street, world-class dining, vibrant galleries, and pristine beaches. Step inside to discover a light-filled sanctuary where 14-foot cathedral ceilings crown an expansive open-plan living, dining, and chefs kitchen area. French doors seamlessly blend indoor and outdoor living, inviting you to a private paradise. The spacious kitchen features Caesarstone Quartz countertops, a Sub-Zero refrigerator, a Wolf gas range, Fisher & Paykel double-drawer dishwasher, beverage drawers, and a microwave drawer. Outdoors, indulge in Key West living at its finest with a sparkling heated swimming pool, a large deck for entertaining and sunbathing, a serene waterfall, and lush tropical landscaping. A covered sitting area offers the perfect spot to unwind. There is a Sonos sound with Focal low-profile speakers to fill the air with your favorite tunes throughout the main house. The main house features two guest rooms, a shared bathroom and a washer and dryer conveniently located between them, and a luxurious primary suite with its own washer and dryer. Impact windows and doors ensure peace of mind, while privacy fencing and off-street parking for two cars provide unmatched convenience. A super cute, separate guest house completes this property, offering two ensuite bedrooms, a kitchenette, a dining area, and a loft sitting space--perfectly positioned at the back for ultimate guest privacy. A storage shed for pool toys and tools ensures everything has its place. This Key West masterpiece is a rare gem, blending timeless charm with modern luxury. Dont miss the chance to own your own slice of paradise in this superb location! Easy to show! Video link https://n9.cl/1114packer

$4,695,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
3 Bed, 3 Baths, 2,295 SqFt Days Listed: 235
-21.09% ($1,255,000) 13 Price Changes : Last Change 16 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Davit Pads25f

Perched on the oceanfront, this extraordinary Cudjoe Key estate boasts breathtaking views from every vantage point, including the rooftop deck. The solid concrete construction, complete with impact-resistant doors and windows, concrete dock, and poolside cabana featuring a bar, sink, and ice machine, ensures a luxurious haven. Lush landscaping, meticulously maintained on a weekly basis, adds to the propertys allure. Upon entering the coded-entry home, a stunning living, dining, and kitchen area unfolds, complete with quartz countertops, stainless steel appliances, and a convenient laundry room. The kitchens center island is spacious and includes refrigerator and freezer drawers, a cooktop and barstools, making it a great entertaining area. The main levels ensuite bedroom, featuring double beds and a jack-and-jill bathroom, offers direct access to the oceanfront patio and a spiral staircase leading down to the pool. Ascend to the master suite, where a lavish bathroom awaits, complete with a jetted tub, double sinks, programmable commode, and walk-in shower, all set against the backdrop of dazzling ocean views. A third ensuite bedroom, features a walk-in shower, single sink, and expansive mirror, with the king-size bed positioned to maximize the stunning vistas. The private outdoor area, complete with a mermaid-adorned pool, large BBQ area, and cabana room, is perfect for outdoor entertaining. World-class fishing and diving opportunities are minutes away, with the Gulf and Atlantic within easy reach. This idyllic location also offers a front-row seat to the marine life of Cudjoe Bay, including porpoise, ospreys, sharks, stingrays, and manatees. Situated in a highly sought-after area of Cudjoe Key, this estate is surrounded by excellent restaurants and boasts wonderful views of the American Shoals Lighthouse.

$4,699,999
Key West
Webb Realty Co Subdivision   - MM: 1.00
5 Bed, 5 Baths, 2,681 SqFt Days Listed: 18
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This stunning home in Casa Marina is a complete restoration of the original historic structure. Just 5 blocks from Higgs Beach and 6 blocks from Duval Street this property has a large master bedroom and two guest bedrooms on the main floor all with private baths and their own entrances opening to over 900 square feet of wraparound porches. The wide entrance hallway has an additional 1/2 bath and opens up into the great room showcasing living, dining and kitchen space with soaring 20 foot ceiling and skylights. The hallway, kitchen and dining room walls are finished with Shiplap and all the floors throughout the home are a stunning custom stained Heart Pine reminiscent of the historic floors of Key West homes. The kitchen boasts a large island with sink & electrical connections as well as seating for 6; a wet bar, two pantries and a full Viking professional package round out the space. There is also a laundry room with a 1/2 bath that opens onto the back deck right next to the 15X8 pool with water feature. The Shiplap continues up the stairs to the interior balcony overlooking the great room and there are 2 additional bedrooms each with their own private baths and walk-in closets as well as a massive storage area that wraps an entire half of the second floor and is a finished and fully air conditioned space. All exterior doors are Mahogany impact with impact transoms and all windows are impact as well. Also, a 250 gallon propane tank is buried, hooked up to the gas stove & on demand water heater and is generator ready. There is 1 off street parking spot with electric gate. The home has been professionally landscaped and professionally furnished.

$4,700,000
Key Haven
Key Haven 10th Add   - MM: 5.00
5 Bed, 5 Baths, 4,480 SqFt Days Listed: 219
-17.47% ($995,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift60ft.

Fully renovated in the last 4 years, this 5-bed, 5-bath, exquisite gated estate with its brand new resort-style pool, and Chefs kitchen boasting new Sub-zero, Wolf, and Miele appliances, offers 2 master suites on the 3rd floor with a private balcony and new interior 3-story elevator! This waterfront Key Haven estate offers a full length concrete dock and 15K lift, while the stunning indoor/outdoor integration invites you to savor the idyllic surroundings. The 4,500 SF of luxurious living space harmonizes with the tranquil beauty of its environment, featuring breezy outdoor spaces and light-filled interiors. Every detail has been thoughtfully designed for refined living, from the Hubbardton Forge lighting to the expansive walls of impact windows that frame breathtaking views of the turquoise Gulf waters. Enter through a grand entryway with a sweeping staircase and elevator into a spacious Great Room perfect for entertaining. The Chefs kitchen is a culinary masterpiece, equipped with high-end, stainless appliances, striking quartz countertops with a waterfall edge, and a breakfast area offering picturesque canal views. Dine in the elegant dining room or al fresco on the sprawling waterfront covered veranda. Guests will revel in the comfort of three well-appointed en suite guest bedrooms, one equipped with a steam shower, while you retreat to one of two third-floor primary suites, featuring spa-inspired bathrooms complete with Hansen & Bringle cabinetry, expansive walk-in showers, and terrace perfect for soaking in Keys famous sunsets. For added convenience each floor includes a laundry area and kitchenette, making lifes conveniences just steps away. After a day on the water, dock your boat, take a refreshing dip in the brand new custom pool, or cook your fresh catch in the outdoor kitchen. Situated within a peaceful, established neighborhood yet just minutes from the magic of Key West, this one-of-a-kind Caribbean masterpiece has it all.

$4,799,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
4 Bed, 4 Baths, 3,817 SqFt Days Listed: 39
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift150ft.Concr

Exquisite LUXURY Waterfront Estate in the exclusive Cudjoe Gardens. A STUNNING TURNKEY PARADISE, PRICE INCLUDES, 2021 PATHFINDER 2400 TRS BOAT WITH YAMAHA 300HP, 2 NEW HOBIE CAT KAYAKS, HIGH END DESIGNER FURNISHINGS & DECOR. Step right into the island lifestyle with these included! This Custom Built Home is a masterpiece blending luxurious design with the serene beauty of the Florida Keys. Built on a sprawling waterfront elevated corner lot of 16,500sf with 260 feet of water frontage offering deep draft. This gorgeous property offers an unparalleled tropical lifestyle, perfect for those who demand the best in comfort and elegance.Property Highlights4 Bedrooms + Office/Studio: Spacious, sunlit rooms designed for relaxation and productivity, including a versatile office or creative studio space which could be a 5th Bedroom.4 Full Bathrooms: Impeccably designed with high-end fixtures and finishes.Gourmet Kitchen: A chefs dream, featuring state-of-the-art appliances, custom cabinetry, and expansive Quartz countertops ideal for entertaining.Imported Italian Flooring: Stunning, high-quality flooring that enhances the luxurious ambiance throughout.12-16 Ft Ceilings: Create an open, airy feel while showcasing architectural sophistication.Saltwater Pool: Dive into the generously sized, chilled & heated concrete pool with water feature and lounging platformOutdoor Kitchen: Stainless Steel Appliances, Spacious layout, Perfect for entertaining.2 Boat Lifts, 20k and 10kAdditional Amenities3 A/C Units: Individually climate-controlled zones, including the 3-car garage for comfort and convenience.Full Property GeneratorThis meticulously designed property combines sophisticated interiors with exceptional outdoor living spaces. Located in a prime area of Cudjoe Key, this home offers privacy, stunning water views, and direct access to the pristine waters of the Lower Keys.Dont miss the opportunity to own this extraordinary piece of paradise

$4,850,000
Key West
Old Town Unrecord   - MM: 1.00
5 Bed, 5 Baths, 3,148 SqFt Days Listed: 44
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Investment opportunity! Weekly rentals are allowed! Nestled within the highly sought-after Truman Annex in Old Town Key West, 202 Admirals Lane exudes coastal charm and luxury living at its finest. Boasting 5 bedrooms and 4 full bathrooms, this meticulously maintained residence showcases beautifully renovated bathrooms and a private pool oasis, offering an idyllic retreat for residents and vacationers alike. Situated nearby the iconic Duval Street and the tranquil expanse of Fort Zachary Taylor State Park, this home epitomizes the quintessential Key West lifestyle. Upon entering, youre greeted by an inviting main living area, adorned with French doors that effortlessly blur the lines between indoor and outdoor living. A sun-drenched sunroom, encased in glass doors, is the perfect setting for relaxation or entertainment year-round. Additional living spaces abound, including a bright and airy sitting room. The main floor is thoughtfully appointed with a convenient full bathroom, ensuring comfort and convenience for guests. The 2nd level offers 4 bedrooms and 3 full baths and the ensuite 3rd floor is great for guest . Included is a Truman Annex transient rental license allowing for weekly rentals, 202 Admirals Lane presents a lucrative investment opportunity as a successful vacation rental. Rare for Key West, this home features a coveted 2-car garage, providing secure parking and storage, a coveted amenity for sure. Offered turnkey, the residence comes complete with all furnishings and future reservations, promising a seamless transition for discerning buyers or investors seeking the ultimate Key West retreat.

$4,995,000
Big Pine Key
Pine Channel Estates   - MM: 29.50
4 Bed, 4 Baths, 3,727 SqFt Days Listed: 8
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits332ft.Concrete

Experience the Pinnacle of Coastal Elegance in Big Pine Key!This openwater masterpiece designed by noted architect Glen Gray, is where modern luxury meets tropical serenity. This luxurious 4-bedroom, 4 1/2 -bathroom estate is a testament to impeccable design and indulgent living. Step inside and be greeted by soaring cathedral ceilings, walls of glass, and an open floorplan that flows seamlessly through grand living spaces. A chefs kitchen, outfitted with Viking appliances, custom hickory cabinetry, and granite countertops, is both a culinary haven and a design showpiece. Two spacious ensuite bedrooms and a private study or media room grace the main level, while the second-floor primary suite is a sanctuary of its own, featuring a spa-inspired bathroom, a loft sitting area, and a private balcony with sweeping open water views. A personal elevator connects all levels, ensuring effortless access, while the detached 936 sq. ft. guest cottage--connected by a covered breezeway--offers a private retreat complete with a kitchenette, wraparound balcony, and great room. The outdoor oasis is nothing short of breathtaking. A sparkling custom concrete pool and hot tub, controlled by Aqualink remote systems, sit amid lush tropical landscaping, providing a resort-like setting for relaxation or entertaining. The estates extensive 332-ft concrete seawall includes two sets of boat davits, a fish-cleaning station, and swimming access, making it a boaters paradise with direct access to pristine waters. No luxury has been overlooked--impact windows and doors, a whole-house generator, and ADT remote security provide peace of mind, while the three-zone A/C system ensures comfort year-round. Situated just 30 miles from Key West and mere minutes from Looe Key Reef, this waterfront estate is your gateway to the best of the Florida Keys lifestyle. Immerse yourself in unrivaled luxury and coastal living-schedule your private tour today.Video: https://n9.cl/flythrough-29433-enterpris

$4,995,000
Key West
Old Town Unrecord   - MM: 1.00
4 Bed, 4 Baths, 3,015 SqFt Days Listed: 223
-3.94% ($205,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Welcome to 524 Frances Street, where sophisticated style meets Old Town charm. Rarely does an architectural gem such as this property become available for purchase. This iconic home has been completely and professionally updated, including impact windows and doors. Enter the property through a white picket fence and ascend the front porch steps with views of Frances Street. Just beyond the historic, glass-etched front door is a welcoming foyer; prepare to be awestruck by the style and craftsmanship of the home. Situated on a double lot, this 4 bedroom/3.5 bathroom property is the ultimate Key West escape, with Brazilian Cherry wood floors, crown moulding and top of the line finishes. The first floor offers three bedrooms. Two spacious guest bedrooms, each with Queen-sized bed and custom closets, are adjoined by a shared bathroom with standup shower. Opposite side of these guest bedrooms is a formal living room with double sliding pocket doors leading into a formal dining room with access to a side porch. Beyond the dining room is a gourmet kitchen that overlooks an additional living room with wall-to-wall glass doors. A hallway leads to a separate wing inviting you to one of two Primary Suites at this property (the second Primary Suite is upstairs). With a King-sized four-posted bed, and ensuite bathroom with dual headed shower and soaking tub. Upstairs is the second Primary Suite with open-concept layout, no need to ever leave this room, as the second floor is only for this room. A beautiful soaking tub to just let all your trouble slip away, with a double stand-up shower. A wet bar with wine fridge serves as the perfect coffee bar for your morning cup, or an evening drink on your private sundeck overlooking the backyard. The private backyard offers a huge in-ground lap pool, outdoor shower, Ipe wood decking, & outdoor dining gazebo with built-in Wolf grill. This home comes with two brick-paved, gated driveways. Offered turn key with a very small exclusion list.

$4,999,500
Big Pine Key
Pine Channel Estates   - MM: 29.50
4 Bed, 4 Baths, 2,812 SqFt Days Listed: 52
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift50ft.

LUXURY LIVING IN THE LOWER KEYS where the pace of life is a bit slower, and the fishing and diving are exceptional. The 16,875 sq. ft. property features 150 ft. of frontage along a 46 ft. wide canal, a 50 ft. concrete dock, and two boat lifts (the larger lift is 21,000 lbs.) Its a private, tropical setting where one can relax under the tiki or in the heated, salt system pool, enjoy down time in the hot tub, and entertain on the primary canal-side porch overlooking protected lands across the canal to the north. This impressive home offers 2812 sq. ft. of living area and an open floor plan with cathedral ceilings, wall-to-wall glass doors and windows in the great room, a formal dining area, a study that can easily be a fourth bedroom, and a master suite with water views. For guests theres a two-bedroom, one-bath wing boasting its own laundry room and canal-side porches. 3-zone central air and heat. Spacious two-car garage and ample ground level storage; plenty of space for guest parking and room to park your motor home and boat trailer. Fly privately into the Marathon International Airport or commercially into Key West International Airport.

$5,250,000
Key West
Old Town Unlisted   - MM: 1.00
5 Bed, 5 Baths, 3,434 SqFt Days Listed: 28
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Discover the charm of Casa Grande, a stunning TRANSIENT residence with a strong rental history. Nestled on a tranquil dead-end street, just one block from the vibrant Duval Street in Key West, this exceptional home offers off-street parking for two vehicles.Designed for entertaining, Casa Grande features an expansive open floor plan that seamlessly connects the spacious living room to the kitchen, creating the perfect setting for gatherings. Step outside to enjoy one of the largest private pools on the island, surrounded by a beautifully landscaped backyard that includes a half bath and outdoor shower--ideal for lounging, dining, or barbecuing in complete privacy.This remarkable home boasts five well-appointed bedrooms and six bathrooms. One suite includes a kitchenette and separate living area. You can walk or bike to local attractions, dining, shopping, and beaches.Dont miss out on this incredible opportunity to own a transient rental property in Key West!

$5,399,000
Key West
Old Town Unlisted   - MM: 1.00
4 Bed, 4 Baths, 3,026 SqFt Days Listed: 413
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Nestled in the storied heart of Old Town Key West, this grand estate is a masterpiece of luxury & history. Spanning a majestic 8,397 sq. ft. lot, the property at 1014 Southard St. Invites you into a world where classic charm meets modern elegance.With 4 bedrooms and 3.5 Baths and over 3,000 sq. ft. of interior space across two separate structures, enjoy an unparalleled gem in one of Key Wests most coveted neighborhoods. Constructed in 1899 by renowned William Cash, this estate radiates a colonial grandeur, enriched with a cranberry cut -glass transom sophisticated dark green shutters & classic french doors.The current owners have meticulously restored the property using only the finest selection of materials, from river reclaimed old growth hardwood floors in living room and hallways, to stunning Blue Castle Limestone in master suite and kitchen and continued through the magnificent garden and pool to the separate guest quarters. Smarthome features have been introduced, including Zigbee Lights integrated with Home assistant, sensor mixs, Ecobee Thermostats, 6 Node Eero Mesh Network, Abode Alarm Systems & Nest protect Sensors.The master suite located on the ground level is a peaceful sanctuary with private library & den, exceptional ensuite, three sets of French doors and opens out to the magnificent saltwater pool and tropical landscaped garden. Two additional bedrooms on second floor in main house share a bath and private veranda.Separate cottage provides exceptional guest quarters and can be accessed from Roberts Lane for additional convenience. Stunning post & beam cathedral ceilings, Limestone floor, built-in bar and kitchenette and spacious living room offers excellent space for entertaining with deck and pool access.Additional features include, One off-street parking spot, equipped with Tesla charging station & new 2023 generator powered by dual propane tanks.Welcome to Key West Living at its finest.

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 01-15-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA