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Florida Keys LUXURY Homes for Sale, Single Family Houses, Florida Keys Real Estate

Total Listings 1,188
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$1,350,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
3 Bed, 3 Baths, 960 SqFt Days Listed: 475
-3.57% ($50,000) 3 Price Changes : Last Change 99 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Beautiful Downtown Islamorada Cottage! This newly constructed home is located on an oversized lot with a pool, outdoor entertaining area, plenty of storage, parking, and handicap access. The home features 3 bedrooms & 3 bathrooms with two of the bedrooms ensuite. The home offers a great floor plan and has been tastefully decorated with a beautiful kitchen including stainless steel appliances. This is a great investment with rental history. Dont miss the opportunity to own where you can walk and ride your bike to all the places downtown Islamorada has to offer including shopping, restaurants, bars, and all the amenities The Sports Fishing Capital of the World has to offer!

$1,350,000
Little Torch Key
Jolly Roger Estates   - MM: 28.50
3 Bed, 3 Baths, 2,080 SqFt Days Listed: 90
-22.86% ($400,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat LiftConcrete

LIVE THE FLORIDA KEYS DREAM in beautiful Jolly Roger Estates where your favorite fishing and dive spots are within easy reach by boat. If youre here to play and relax, this newly (2020) constructed (mostly furnished) turn key home offers low-maintenance living with lovely in-ground heated pool and 220 sq. ft. Tiki Hut offers just that. Home is surrounded by a 4 foot high by 196 Linear feet of PVC fence for privacy and pets if desired. For your boat there is plenty of seawall with a 10,000 pound Boatlift. Home offers 2080 sq. ft. of living area upstairs plus two screened porches. Home is a 3 bedroom with 2 full bathrooms with tile floors and crown molding throughout. Master Bedroom is huge and all bedrooms have California closets. The homes ground level has an entertainment area adjacent to in-ground pool with garage space for a vehicle and a spacious storage room for fishing and diving gear, etc.. The lot has parking for 4 vehicles.

$1,350,000
Plantation Key
Fontaine Lake   - MM: 90.00
5 Bed, 5 Baths, 2,492 SqFt Days Listed: 59
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Live the dream in this elevated Plantation Key retreat, designed for ultimate comfort and island living! The freshly painted main home offers 3 bedrooms, 2 baths, an open coastal-style layout, and an upgraded kitchen with stainless appliances, gas cooktop, and wine bar. Enjoy updated LED lighting, new ceiling fans, and a refreshed guest bath.Downstairs, a finished storage area with bath adds extra flexibility.Outside, your private oasis awaits--a screened-in heated saltwater pool surrounded by lush landscaping, plus modern perks like a tankless propane water heater, whole-house generator, 500-gallon propane tank, and water softener.Need space for guests? The separate 2-story guest house (2018) features 1 bed/1 bath on each level, new quartz counters, fresh stainless appliances, impact windows, and LPV flooring throughout.All this in the heart of Plantation Key, minutes from world-class fishing, dining, and a nearby boat ramp--just 90 minutes from Miami and 2 hours from Key West.Buyer to verify all facts.

$1,349,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,520 SqFt Days Listed: 223
-3.30% ($46,000) 2 Price Changes : Last Change 122 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Unique opportunity to renovate this historic Old Town eyebrow home on a quiet, one-way, block of Elizabeth Street. Situated on a 2623 Sq.ft. lot there is ample space for off-street parking, a pool and 5 bedrooms with a renovation. Seller financing possible. Please note that advanced notice is required to arrange showings.

$1,349,000
Key West
Riviera Shr Amd Plat   - MM: 3.00
3 Bed, 3 Baths, 1,512 SqFt Days Listed: 54
-15.42% ($246,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat LiftConcrete

NEW PRICE!! CANAL HOME IN KEY WEST!! Fabulous Canal Home in Key West. Spacious CBS three bedroom, two bath home in Riviera Shores. Perfect island home is private and offers plenty of indoor and outdoor living areas including bricked courtyards, verandas, and deck spaces. This home has beautiful grounds and tropical landscape for relaxing in your hammock or enjoying the canal. The primary bedroom offers dressing area, en suite bath and access to the backyard. Detached cottage with storage, laundry or would make a perfect home office. Additional highlights of this elegant home include Saltillo tile flooring, central air conditioning, covered parking, and a seawall equipped with a boat lift, making it a perfect haven for those who love the water. This canal home is a unique opportunity to embrace the quintessential Key West lifestyle.

$1,349,000
Little Torch Key
Jolly Roger Estates   - MM: 28.50
3 Bed, 3 Baths, 1,400 SqFt Days Listed: 184
-9.77% ($146,000) 4 Price Changes : Last Change 5 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: BasinConcrete

Dream Home Alert in Little Torch Key!365 Pirates Rd, Jolly Rogers Estates.Escape to paradise in this stunning concrete gem nestled in the highly desirable neighborhood of Jolly Rogers Estates on the serene Little Torch Key! This charming house is your canvas, ready for your personal touch and stylish furnishings.Property Highlights include,* Modern Amenities: Enjoy all stainless steel appliances, impact doors and windows, and a durable metal roof that ensures peace of mind.* Breathtaking Views: Overlook the picturesque salt ponds to the west, where you can unwind with breathtaking sunsets that paint the sky.* Relaxing Oasis: Dive into your sparkling custom pool surrounded by lush landscaping and hand-selected palms, all accented by beautiful silver travertine that wraps the pool area.* Boaters Paradise: With solid concrete docking just steps away, your boat is ready for adventure! In just 3 minutes, you can be out in open water, exploring some of the cleanest waters teaming with wildlife in the Lower Keys.*Endless Outdoor Adventures: Fish offshore, explore the tranquil flats of the Gulf chain islands, or venture out to the Gulf wrecks and towers for some great fishing. Prefer a leisurely day? Relax on a sandbar, gaze at the clouds, and let the worries of daily life drift away.After a day on the water, treat yourself to a meal at a local restaurant, showcase your fresh catch, and enjoy live music--perfect for winding down and savoring the island lifestyle.This house is more than just a home; its a lifestyle waiting for you to embrace! Dont miss your chance to own a piece of paradise in Little Torch Key. Schedule your viewing today and start your journey to coastal living!

$1,345,000
Key West
Key West Golf Club Dev   - MM: 4.00
3 Bed, 3 Baths, 1,600 SqFt Days Listed: 62
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Discover your dream home in the prestigious Sanctuary at the Key West Golf Club. This 3-bedroom, 2.5-bath single-family residence overlooks the 18th fairway with a spacious private backyard.Inside, the open-concept floor plan offers bright and airy living spaces, including a flexible downstairs bedroom--ideal as a sitting area or office. The large kitchen includes a convenient half bath, while the generous living area opens through French doors to a large covered porch and private pool--perfect for entertaining and unwinding in a serene setting.Upstairs, two bedrooms share a covered balcony and full bath, while the expansive primary suite features a private en suite bath and its own large porch. Additional highlights include off-street parking for two vehicles and a carport.Located in a gated, private community, residents enjoy access to two resort-style pools, a fitness center, and 24-hour security.Dont miss this rare opportunity--schedule your private showing today!

$1,339,999
Long Key
Long Key Estates   - MM: 68.00
4 Bed, 4 Baths, 2,964 SqFt Days Listed: 80
-10.37% ($155,001) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 60ft.

This 4-bedroom, 4-bathroom concrete home w/ impact windows & doors offers the perfect blend of comfort and coastal living. Featuring a spacious living room, formal dining area, large bedrooms, walk-in pantry, separate vanity area in Primary bath, cedar-lined closets throughout and a massive game room for endless entertainment. Relax in the hot tub in the large, screened room overlooking the canal, watching tarpon roll and manatees visit. Pre-firm downstairs living space is perfect for live-in caretaker or supplemental income. 60 feet of concrete dockage, is a boaters dream offering easy access to the Ocean. The quaint neighborhood of Layton is nestled between Islamorada and Marathon and has much to offer! Post Office, fire department, restaurant & bar, community pickleball court, Long Key State Park with wonderful nature trails, all within walking & biking distance. Whether youre looking for a private retreat, a versatile compound for work or play with potential income, this property is ready for your vision to make your dream of paradise a reality.

$1,335,900
Key Largo
Key Largo Beach Addition   - MM: 100.00
5 Bed, 5 Baths, 2,157 SqFt Days Listed: 33
-6.25% ($89,100) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 36ft.

Experience waterfront living at its finest in beautiful Key Largo! As you step inside, youre greeted by stunning high vaulted ceilings that set the tone for this spacious home, offering five bedrooms and three bathrooms across 2,157 square feet of thoughtfully designed living space with convenient laundry access on both floors. Enjoy breathtaking ocean views from your living room, bedroom, or while relaxing on your pool deck. The upstairs features three bedrooms and two bathrooms, while the downstairs offers two additional bedrooms and a full bath, plus a versatile recreational space.The heart of this property is its exceptional outdoor area. A large, saltwater pool up to 8ft deep, invites you to bask in the Florida sun, surrounded by a generous pool deck perfect for entertaining or unwinding. Situated on an oversized corner lot with over 42 feet of canal frontage, the lush greenery and ample parking provide plenty of space for your vehicles, toys, and guests. Featuring a single-car garage, metal roof, modern impact windows, doors, and skylight. The modern kitchen, complete with stainless steel appliances, a wine cooler, granite countertops, and a sleek bar top, is perfect for any occasion. Located near Key Largo Park, youll be close to Key Largo Fisheries, schools, shopping, and just an hour to Miami. This is the ultimate Key Largo retreat!

$1,325,000
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,620 SqFt Days Listed: 12
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Welcome to your perfect getaway in the heart of the Florida Keys! This beautifully updated 2-bedroom, 2.5 bathroom townhouse is located in Islamorarda in a resort-style community with fantastic amenities. Whether youre looking for a vacation home, an investment property, or both, this tropical retreat offers everything you need.Enjoy an open-concept living space with abundant natural light, a fully equipped kitchen, and spacious bedrooms with en-suite bathrooms. Step outside to your private balcony or patio and soak in the island breeze. This townhome is the only property in association that is situated on two lotsThe community features a sparkling pool, a marina with boat dockage. With weekly rentals allowed, this property is a fantastic income opportunity in a high-demand tourist destination.Located just minutes from world-class fishing, boating, snorkeling, and dining, this townhouse offers the ultimate Florida Keys lifestyle. Dont miss out on this rare opportunity--schedule your private tour today!

$1,325,000
Key Largo
Pirates Cove   - MM: 98.50
3 Bed, 3 Baths, 1,350 SqFt Days Listed: 187
-9.68% ($142,000) 2 Price Changes : Last Change 41 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp6

Prestigious Pirates Cove - Secluded Lake/Front Basin Home - Direct Ocean & Bay access in just minutes - 3Bed/2 Baths - The Upper Level is a 2 Bedroom/ 1 Bathroom & Lower Unit is a **Grandfathered in designated 1Bedroom/1 Bathroom with a Full Kitchen. Solid Concrete Dock equipped with a 15000 LB boat lift & Separate Jet Ski lift -Also property is Secured by an Electric Gate & Fenced in Yard complete with Shaded Patio area with Pavers and Tropical Landscaping - fish cleaning station & storage. Centrally located near Shopping, Schools & Restaurants.

$1,318,800
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 1,109 SqFt Days Listed: 44
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Located in the heart of historic Key West in the X Flood Zone (no flood insurance required), this beautifully renovated conch cottage offers a perfect blend of classic charm and modern comfort. Just three blocks from Duval Street and half a block from the Truman Annex, it sits in a quiet yet walkable neighborhood close to top attractions. This flexible two- or three-bedroom home features tall ceilings, new impact windows, 3/4 inch wood flooring, and rich Dade County pine walls. The dining room flows into the well appointed kitchen, where Dade County pine counters complement high-end appliances, including a Sub-Zero refrigerator, Big Chill gas stove, and dishwasher. A rare oversized laundry and utility room provides extra space for projects or storage. Originally built between 1899 -1907, as a Henry Flagler Railroad home, this historic gem has a classic front porch where the song The Beautiful Isle of Key West by Ellen Sanchez was composed. The private backyard is filled with fruit trees--mango, avocado, and Key lime, its a butterflys haven and there is even room to add a small pool. With the Truman Water Park, Amphitheater, and Fort Zachary Taylor Beach just moments away, this is island living at its finest!

$1,300,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 2,240 SqFt Days Listed: 38
-7.14% ($100,000) 1 Price Change : Last Change 8 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Looking for a home to accommodate you and your guests? This concrete construction property features three bedrooms and two baths on the upper level. Lower level offers two bedrooms and one bath, plus a waterfront screen porch, open floor plan, legally permitted enclosure with a living area that includes a kitchenette, plus living room. Plenty of storage with attached workshop/garage. Located on a plugged canal in Venetian Shores, there is a marina available for lease dockage monthly depending on availability.

$1,300,000
Key Largo
Cross Key Waterways   - MM: 103.00
4 Bed, 4 Baths, 2,568 SqFt Days Listed: 32
-6.81% ($95,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits

NEW PRICE DROP! MULTI-GENERATION families, INVESTORS this is a must see! Prime waterfront location for fishing, diving, and boating enthusiasts. Featuring a concrete block home with incredible potential, it provides immediate access to both ocean and bay-side adventures via a concrete dock. Whether youre finishing your day with a sunset on the water or hosting friends, the Sound views from nearly every corner of the property create a stunning backdrop for any occasion. Unbeatable waterfront access, perfect for ocean and bay-side boating. Expansive two-story layout with 2,304 sqft of living space (1,152 sqft per floor). 3 Bedrooms, 2 Bathrooms--ideal for families or a lucrative investment. with a BONUS Building serving as as a Cozy 1 bed/1bath guest quarters for visitors. Opportunities for single family, a MULTI generational family, a peaceful vacation retreat, or a smart investment, this property offers endless possibilities. Enjoy breathtaking views, a tranquil environment, and the ultimate waterfront lifestyle. Dont let this extraordinary opportunity pass by!

$1,300,000
Key West
Lime Grove   - MM: 3.00
3 Bed, 3 Baths, 1,052 SqFt Days Listed: 157
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Welcome to your dream home in the heart of Key Wests New Town! This beautiful 3-bedroom, 2-bathroom residence offers the perfect blend of comfort and convenience. Step inside to discover a spacious and inviting interior, featuring an open-concept living area. The true highlight of this property is the private backyard oasis. Imagine spending your days lounging by the pool, hosting gatherings on the expansive deck, or simply enjoying the serene surroundings. The outdoor area is perfect for both entertaining guests and unwinding in your own private paradise. Parking will never be a hassle with off-street parking available, providing convenience and peace of mind. Recently renovated with new impact doors and windows and hardiboard siding! Located in the desirable New Town neighborhood, this home is just a short distance from an array of dining and shopping options, ensuring you are never far from the vibrant lifestyle Key West has to offer. Dont miss the opportunity to own this slice of paradise. Schedule a showing today and experience the best of Key West living! Great opportunity for investors or 1031 exchange buyers. Long term renters in place. Call for details.

$1,300,000
Key West
Pearlman Heights   - MM: 4.00
5 Bed, 5 Baths, 2,016 SqFt Days Listed: 13
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Welcome to 1006 16th Terrace, a charming two-story residence nestled in the New Town area of Key West, Florida. This well-maintained home boasts 5 bedrooms and 3 bathrooms offering a floorplan that will accommodate multiple situations. The exterior of the home is a testament to meticulous landscaping, creating a serene and inviting atmosphere. A detached storage unit provides additional space for a multitude of uses. The residence features a two-zone air conditioning system, ensuring optimal comfort throughout the year. The home has been recently painted, adding to its fresh and well-kept appearance. The original ground level home was built in 1965; however, the second story addition was built in 1993. The home is equipped with storm rated windows and doors for your added protection. Whether you are looking for a single-family home or a multi-family arrangement, this property at 1006 16th Terrace combines comfort, functionality and the charm of Key West living. Call today for your private showing.

$1,299,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
4 Bed, 4 Baths, 2,448 SqFt Days Listed: 136
-3.71% ($50,000) 1 Price Change : Last Change 22 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 50ft.Concrete

This stunning 4 bedroom, 3 bathroom canal front home offers the perfect blend of functionality and luxury. With 2,448 Sq. Ft. of living space this home is perfect for large familys, the property features an expansive covered balcony on both floors and a large kitchen / dining room for entertaining. The updated bathrooms and spacious master suite provide a comfortable retreat, while the exterior offers plenty of space for off-street parking and room for a pool. There is a downstairs enclosure for extra storage. Great water access to the Gulf and Atlantic. Awesome restaurants and bars within walking distance. Bring your boat and come enjoy the Florida Keys!

$1,299,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
3 Bed, 3 Baths, 1,361 SqFt Days Listed: 45
-4.42% ($60,000) 1 Price Change : Last Change 11 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Nestled in one of the Lower Keys most coveted boating communities, this meticulously renovated 3 bedroom 2 bathroom coastal retreat is more than just a home...its a gateway to endless aquatic adventures. Situated on a deep-draft, flow-through canal with direct access to both the Atlantic and Gulf, this property is a dream for fishing, diving, and island-hopping enthusiasts. The brand-new concrete dock is built for the serious boater, ensuring effortless departures for your next adventure. Step inside to find a seamless blend of modern elegance and island charm. The light-filled, open-concept living space is adorned with custom tile flooring throughout, sleek quartz countertops, and premium stainless steel appliances, creating an ambiance that is both stylish and functional. The spacious guest bedrooms offer plenty of room for family and friends, while the serene primary suite serves as a private retreat, complete with a spa-like ensuite bath. Designed for both beauty and resilience, this CBS-constructed home features impact windows and doors, giving you peace of mind during any season. Beyond your backyard paradise, Cudjoe Gardens Marina is just steps away, offering a full-service experience with a large boat ramp, fuel dock, convenience store, and the beloved Bent Prop Restaurant & Bar--perfect for enjoying a sunset cocktail after a day on the water.Whether youre seeking a full-time residence or the ultimate vacation getaway, this home delivers luxury, convenience, and some of the best boating access in the Lower Keys. Dont miss your chance to own this waterfront gem.

$1,299,000
Big Pine Key
Kyle Dyre   - MM: 28.00
3 Bed, 3 Baths, 1,440 SqFt Days Listed: 23
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Enjoy your morning coffee taking in views of the Bay, and watching the boat traffic go by on your large covered deck. In the evening, enjoy a cocktail while watching the sunset. There is approximately 210 feet of concrete seawall to park your boats and water toys. This meticulously maintained home has a metal roof, impact doors and windows, newer A/C, and many updates. Low flood insurance premium. Sellers prefer afternoon showing appointments. No pets allowed in the house on showings.

$1,299,000
Long Key
Long Key Estates   - MM: 68.00
3 Bed, 3 Baths, 1,607 SqFt Days Listed: 48
-5.53% ($76,000) 1 Price Change : Last Change 9 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift60ft.Concre

Experience this beautifully renovated waterfront residence, where modern coastal design meets functional elegance. Situated along a serene oceanside canal, this home offers a spacious terrace with partial Gulf views, creating an inviting outdoor living space. Inside, meticulous updates include quartz countertops, luxury vinyl plank flooring, recessed lighting, and Calacatta marble-tiled showers. The interior staircase leads to the main living area, which features an open-concept kitchen, living room, three bedrooms, a bonus office or guest room, and two full bathrooms. Step outside to the generous covered porch and take in the tranquil canal views with a backdrop of the picturesque bay. The property includes 60 feet of protected concrete dockage, complete with a 20,000 lb. boat lift, providing swift boating access to both the Atlantic Ocean and the Gulf of Mexico. New impact windows, doors and roof in 2018. Additionally, a versatile flex space on the lower level offers potential for a home gym, storage, anglers room or additional entertainment space. This refined coastal retreat seamlessly blends luxury and convenience, inviting you to make it your own.

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 04-05-2025.
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