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

Total Listings 1,032
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$1,119,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
6 Bed, 6 Baths, 2,320 SqFt Days Listed: 151
-6.67% ($80,000) 5 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift60ft.Concre

Welcome to 184 Cutthroat Drive, a wonderful income producing waterfront home on the peaceful Cudjoe Key. This home is being sold fully furnished and with kayaks! Has a spacious open floor plan with lots of natural light.Main Level (Upstairs):4 bedrooms, split for plenty of privacy2 full bathroomsLarge living, dining area, and kitchen with an open layout and tons of counter space and cabinets, and stainless steel appliances.Large deck for relaxing and star gazing on clear nights.All new impact windows and doors on upper level.New AC 2020Lower Level (Legal Pre-FIRM Downstairs):2 additional bedrooms1 full bathroomSeparate living space, ideal for guests or extended familyDirect outdoor access for easy enjoyment of the waterfront. Separate set of washer and dryer for downstairs. Outdoor Features:Private canal frontage with quick access to open waterPartial fenced in front areaNew roof 2017New 10,000lb boat lift, and new composite dock.Ample storage for your water sports and fishing gearThis home is a great opportunity for those looking for a property to enjoy the natural beauty and recreational opportunities of the Florida Keys and large enough to bring all their friends and family along with them! With its prime location and in walking distance to the Square Grouper one of the best restaurant in the Keys, 184 Cutthroat Drive is a true gem!

$1,118,000
Cudjoe Key
Cudjoe Ocean Shores   - MM: 23.00
3 Bed, 3 Baths, 1,225 SqFt Days Listed: 57
+8.54% ($88,000) 2 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Wow New Price. Best value in the area!! Discover the ultimate lifestyle with this 3-bedroom, 2-bathroom waterfront canal home on Cudjoe Key, a prime location. This unique property offers the best of both worlds; fast, convenient access to the open waters of the Atlantic Ocean and the tranquil Gulf of Mexico, allowing you to reach prime fishing spots in no time, dive, snorkel and cruise to the Keys sand bars. NUTS & BOLTS1,225 finished living space, additional lower level enclosed storage, Newer Metal Roof, 7,500 sqft Lot, 75 Canal Front, Stainless Appliances, Renovated Kitchen & Baths, Ample off Street parking The homes open floor plan is tiled throughout, providing a dream coastal retreat. Step outside onto a spacious back porch that overlooks the serene canal, perfect for morning coffee or views. The expansive, fenced-in yard offers both privacy and potential for outdoor enhancements.Additional features include ample storage space with a downstairs storage enclosure, covered parking for up to three vehicles, and a quick commute to the vibrant scene in Key West or the relaxed charm of Big Pine Key. Whether youre a fishing enthusiast or simply looking for an escape, this property promises an unbeatable Keys lifestyle with quick access to blue water and endless opportunity.

$1,100,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
3 Bed, 3 Baths, 1,195 SqFt Days Listed: 77
-4.26% ($49,000) 1 Price Change : Last Change 41 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift40ft.Concre

Welcome to Blackbeard Lane on Cudjoe Key, a stunning stilted home that perfectly combines modern elegance with the charm of the Florida Keys. Built in 2012 and thoughtfully updated, this property boasts 3 bedrooms and 2 bathrooms across 1,195 sq. ft. of beautifully designed living space.The heart of the home is the expansive open-concept living area, seamlessly connecting to a chefs kitchen adorned with high-end appliances, custom cabinetry, a pot filler, and a striking Dade County Pine hood. The primary suite features an ensuite bathroom with custom finishes and generous walk-in closets, while two additional guest rooms share a stylish guest shower.Attention to detail is evident throughout, from the contemporary flooring to the Dade County Pine accents. The home is equipped with impact-resistant windows and a newer roof (2018), ensuring low insurances and peace of mind. Set on a spacious 6,000 sq. ft. lot, this property is a true boaters paradise, featuring a 40-foot seawall and a 10,000 lb boat lift, making it easy to explore nearby destinations like the American Shoal Lighthouse and Looe Key Sanctuary. Additional amenities include an outdoor shower, ample parking, and a downstairs enclosed garage for extra storage.Experience the best of Florida Keys living in this exceptional home!

$1,100,000
Summerland Key
Summerland Beach   - MM: 25.00
3 Bed, 3 Baths, 1,680 SqFt Days Listed: 267
-8.33% ($100,000) 1 Price Change : Last Change 11 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: First Come Dock

Exquisite Summerland Key Oasis...Unparalleled Privacy & Ocean Views with an expansive lot of16,860 sq ft, walled and landscaped for ultimate PRIVACY. Though not directly waterfront, enjoy exclusive access to the community dock at Bergen Park a few blocks away, which is allocated only for use by these Summerland Key Owners. Step into a luminous living space, graced by soaring cathedral ceilings, channeling abundant natural light throughout, offering 3 spacious bedrooms and 2 well-appointed baths, designed for both comfort and style. For Sunrise to Sunset magical moments, an easily accessible rooftop sanctuary offers panoramic Ocean Views, perfect for relaxation or entertaining. Retreat to the Outdoor Living Room, a large covered porch overlooking the pristine in-ground pool, complemented by flourishing fruit and majestic palm trees. OR relax poolside at the perfectly shaded Lobster Trap Bar. Generous 1,680 sq ft of living space is enhanced by a large 2-car garage and additional ground-level storage, ensuring ample room for all your needs. 2021 Renovation included new impact windows and doors, hardi-siding, and roof, plus a custom T&G ceiling. Experience the epitome of coastal living in this meticulously crafted Summerland Key home, where unparalleled privacy meets spacious comfort. As the owner is currently preparing the property and organizing for the move, live showings are extremely limited until June 1st, however other showing options are available, contact your agent for details.

$1,100,000
Key Largo
Calusa Campground   - MM: 101.50
3 Bed, 3 Baths, 1,575 SqFt Days Listed: 117
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Firs

Start living the Keys life in this recently built 3 Bedroom, 2 Bathroom custom concrete Unit that is light filled with modern upgraded features & has the most spectacular Sunset Views on the Bay.Set up as a successful Short Term Vacation Rental with 2-3 night minimums & can negotiate furniture.1 hr drive from Miami & close to everything the Keys has to offer.

$1,100,000
Upper Matecumbe Key Islamorada
Hammock   - MM: 83.50
3 Bed, 3 Baths, 1,518 SqFt Days Listed: 239
-15.38% ($200,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

This beautiful 4-year-old ground-level home features 3 bedrooms and 2 bathrooms. The kitchen boasts stunning all-wood cabinets, granite countertops, and stainless steel appliances. Marble tile floors extend throughout the house, creating a luxurious and cohesive feel.The home includes a large screened porch off the back two bedrooms, perfect for enjoying the surrounding tropical tree canopy. The house is well-lit with all LED lights and features ceiling fans inside and on the porches, providing comfort and energy efficiency.The bathrooms have been thoughtfully designed with backing that will allow for the installation of handicap bars, ensuring accessibility for all. The two-car garage with doors at the front and back provides easy access to the backyard. The low-maintenance landscaping is complemented by a sprinkler system, making upkeep a breeze.For those with a penchant for boating, the home is conveniently close to marinas. Additionally, it is near shopping facilities and some of the best restaurants in the Florida Keys, offering a blend of convenience and leisure.

$1,100,000
Big Pine Key
Cahill Pines & Palms   - MM: 30.00
2 Bed, 2 Baths, 1,464 SqFt Days Listed: 53
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: DavitsConcrete

This home is located on a beautiful 75 ft wide canal and has approximately 60 ft of seawall. Triton Seas Center is located on the same canal, just putt over and fill the boat up for a day of fishing and diving. Features a newer roof (2021), impact doors and windows, A/C (2022), fenced yard and appliances. This unique home plan and location make this home a must see.

$1,100,000
Key West
Old Town Unlisted   - MM: 1.00
2 Bed, 2 Baths, 756 SqFt Days Listed: 70
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Uncover the possibilities of this classic Old Town Key West conch cottage! Beneath the shade of a mature mango tree, the front porch welcomes you to a 2-bedroom, 1-bath renovation project providing the ideal canvas to make it your own. With coveted gated off-street parking and an expansive backyard with space for a pool and outdoor living, this property has room to create the ultimate island retreat.Located in the highly desirable X Flood Zone and Transient License Receivership Zone, this property is just a half block from Duval Street, offering easy access to all of the amenities of Old Town. HNC-1 zoning allows this property to become a transient license receiver property (it currently does not include a transient license).

$1,100,000
Little Torch Key
Jolly Roger Estates   - MM: 28.50
3 Bed, 3 Baths, 1,576 SqFt Days Listed: 27
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 60ft.Concrete

Discover Conch Cottage, a charmingly updated 3-bedroom, 2-bathroom single-family home designed with a thoughtful split floor plan. This inviting retreat showcases bright, spacious rooms adorned with crown molding, recessed lighting, and elegant tile flooring throughout. The kitchen is a chefs delight, featuring granite and quartz countertops, stainless steel appliances, and plenty of cabinet space.Step outside to your private oasis, complete with 60 feet of dockage along a 50-foot-wide canal--perfect for boating enthusiasts with easy access to the ocean and bayside. The fenced backyard is packed with amenities, including a 312-square-foot screened patio, a tiki hut, a permitted detached gear storage/utility room, an outdoor shower, and a convenient fish cleaning station.Blending coastal charm with modern sophistication, Conch Cottage offers the ultimate in luxury and comfort. Fully furnished and turn-key, this home is ready for you to embrace the paradise lifestyle today!

$1,100,000
Big Pine Key
Palm Villa   - MM: 30.50
4 Bed, 4 Baths, 2,493 SqFt Days Listed: 949
-26.67% ($400,000) 2 Price Changes : Last Change 415 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

ONE-OF-A-KIND! Custom-built home on a large 31,250 sqft lot. Built in 2010. 4bd/3bth plus office or bonus room for a total 2493 sqft. Perfect for 2 working professionals from home or a big family. Good size bedrooms; 2 are en suite. Rooms are large. Below the house, there is a concrete slab (3,014 sqft) with covered parking or patio, and a nice large bar that can seat 15 people for entertaining. 20 KW propane generator. Large kitchen with custom concrete counter tops, custom edges, and inlays. Doorways have nice bamboo trim. Walk in pantry. 2 on-demand water heaters. Jetted tubs in two of the bathrooms. Commercial grade bamboo flooring. Surround sound system, Impact windows & doors. Back and front patio decks. Metal roof. Paver driveway. Plenty of room for a pool, vehicles, and boat. Three entrances to the five lots for additions or parking. 2 other large concrete slabs on property. County owned property across whole street. Only 3 homes on the street. Beach within 10 mins, public boat ramps, and parks. Rented till 7/31/25 $5000. mo. util. not included.

$1,100,000
Plantation Key
Coral Harbour   - MM: 88.00
3 Bed, 3 Baths, 1,553 SqFt Days Listed: 240
-15.38% ($200,000) 2 Price Changes : Last Change 51 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Boat Slip3

Step into luxury with this unique top-floor condo at Coral Harbour Club. The kitchen stands out with its custom design, offering modern appliances and plenty of space for culinary adventures. The master bedroom features a bespoke layout with high-end finishes, providing a serene retreat with stunning ocean views.Enjoy the convenience of partial furnishings, allowing you to easily add your personal touch to this beautiful home. The spacious living area is perfect for entertaining guests or relaxing after a day on the water. Speaking of water, the included deeded 35 slip is a rare find and a boaters dream, making this condo an ideal choice for those who love the ocean.Coral Harbour Club offers a range of amenities for residents, including a sparkling pool, a welcoming clubhouse, and private beach access. Located in a prime area, youll enjoy easy access to local shops, dining, and recreational activities, all while being steps away from the beautiful coastline.

$1,100,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
2 Bed, 2 Baths, 1,312 SqFt Days Listed: 34
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 80ft.

Welcome to your perfect coastal retreat! This inviting 2-bedroom, 2-bath home plus office offers the ideal blend of comfort and convenience for boating enthusiasts. Nestled on the Oceanside with no bridges to navigate, it boasts a private 15,000 lb boatlift on 80 ft concrete dock a generous 4-ft draft making it a dream for those who love the water. Relax and unwind in the screened patio, perfect for enjoying the gentle sea breeze. adventures and serene waterfront living. Dont miss the chance to make this slice of paradise your own!

$1,100,000
Little Torch Key
Coral Shores Estates   - MM: 28.00
3 Bed, 3 Baths, 1,400 SqFt Days Listed: 80
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 40ft.

Open Water Views abound at this Little Torch Key retreat! Nestled in the peaceful Coral Shores Estates neighborhood, in proximity to an excellent community boat ramp and just one minute to Open Water, this canal front home is ideal for the avid boater! The open concept main living area is bright and inviting, with stunning Water Views and loads of natural light. The updated kitchen comes complete with granite countertops, ample storage, kitchen island with seating, and gas range. Two sizable guest bedrooms provide excellent accommodation for a family or guests, and the primary bedroom boasts Bay Views and a well-appointed en suite bathroom. An upstairs laundry closet provides added convenience, and additional upgrades include impact doors and impact windows and new composite decking upstairs. The spacious screened-in porch just off the main living area lends itself to entertaining with room for outdoor dining, and stunning views of Keys Famous Sunsets and the pristine canal below. Downstairs, enjoy abundant covered and open parking as well as a bonus storage space for keeping tools and equipment dry and secure. A full length concrete dock with step-down accommodates multiple vessels for easy and frequent fishing and diving within minutes. Just unpack and relax, this fantastic property is outfitted for effortless Keys living!

$1,100,000
Marathon
Key Colony Subdivision   - MM: 53.00
3 Bed, 3 Baths, 1,275 SqFt Days Listed: 69
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift75ft.Concre

Welcome to 11300-1st Avenue Gulf. This 3 bedroom 2 bathroom single family, ground level, canal front home offers open water access to both the Gulf and the Atlantic Ocean, and a screened in heat optional in ground pool. Open floor plan, master bedroom has ensuite bathroom, outdoor screened patio dining area next to pool. Conveniently located near great restaurants, post office, shopping. Call for more information and schedule a viewing of this home. Priced to sell!

$1,099,999
Marathon
Flamingo Island   - MM: 49.50
2 Bed, 2 Baths, 1,200 SqFt Days Listed: 140
-4.35% ($50,000) 1 Price Change : Last Change 77 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This impeccably maintained Flamingo Island Pool home has been beautifully updated to embrace the Keys Island lifestyle. Dont miss the opportunity to live in this highly sought-after neighborhood just steps from the Florida Keys Country Club, a 6,500-yard, Mark Mahannah-designed golf course that offers a challenge to golfers of all levels. Step into your well-appointed kitchen that boasts quartz countertops, large center island with custom double chandelier lighting and extra seating perfect for entertaining family and friends. Stainless steel appliances including a Whirlpool gas range, gorgeous, tropical custom tile backsplash, bright and spacious white cabinets, recessed lighting and a stylish dining banquette rounds off this well-designed kitchen. Large master suite with updated bathroom, large closet, crown molding and beautiful view from your porch overlooking the gorgeous 35-foot pool and mature landscaped fenced-in yard. Guest bedroom is spacious with a large closet and the same beautiful view! Guest bathroom, extra storage closets as well as front-load washer and dryer complete this gorgeous living space! Large 7,690 square foot lot with low-maintenance vinyl privacy fence, mature landscaping, 35-foot, heated pool with custom concrete surround and waterfall feature. Built-in gas grill, underground sprinklers, LED lighting, 4-car garage with plenty of storage in the downstairs with access from the garage and pool area. Oversized driveway for all your cars and toys! House comes turnkey, fully furnished, just bring your swimsuit and get ready to enjoy your new pool home on Flamingo Island!

$1,099,999
Key Largo
Key Largo Ocean Resorts   - MM: 94.50
4 Bed, 4 Baths, 1,584 SqFt Days Listed: 212
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Other Dock

Luxurious 4/3.5 in gated Key Largo Ocean Resort, a golf-cart friendly community featuring 24/7 security gate, clubhouse, fishing pier, marina, onsite boat ramp, basketball & tennis court, swimming pool, gym, kids park and so much more! And thats just the beginning! This home features an open floor plan with master suite on the main level, thick granite on all counters throughout. Kitchen is equipped with a wine cooler! Upper level has an additional master suite plus two more bedrooms. Every bedroom closet has upgraded build-in drawers and shelves. 2 AC units, metal roof, spray foam insulation, covered parking for multiple vehicles or even your boat, interior laundry, tankless hot water heater, outside shower, artificial turf, and lush landscaping. There is also a large storage room on the ground level for all your fishing & water toys. Electric box was also upgraded to include generator plug-in. It doesnt get any better than this. Dont miss this opportunity! Four bedroom homes in this community are rarely available. Picture yourself relaxing on the balcony after a long day of fishing and snorkeling in the crystal clear waters of the Florida Keys. Sit back and enjoy ocean breezes and a frozen cocktail! And bonus........Furniture is included! There are so many upgrades in this home! This is a great home for large families or even as an investment property! Additionally, owners can get on the wait list for a boat slip (additional fee for slip). However, a slip is not necessary as there is an on-site boat ramp and you can store your boat and trailer right under your stilt home! Competitively priced and will go FAST! Paradise is calling your name! Blink and it will be gone!

$1,099,999
Key Largo
Gulfstream Shores   - MM: 108.00
3 Bed, 3 Baths, 2,051 SqFt Days Listed: 15
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

GREAT VALUE in this 4 car garage, screened pool and CBS home in popular Gulfstream Shores. This remarkable ground-level home spans three lots in a coveted area of north Key Largo. The spacious residence features a layout designed for both comfort and entertainment. A split floorplan offers a primary suite on the West wing of the home and secondary bedrooms on the other side with the kitchen in the center as the heart of the home. The home is characterized by its solid concrete construction, offering durability and peace of mind. Conveniently attached is a 2 car garage, with an additional detached 4 car garage providing ample storage space for vehicles or vessels. For relaxation and recreation, a screened-in pool enhances the outdoor living experience with minimal upkeep.Located just a short stroll from the oceanfront homeowners park, residents can enjoy access to a private boat ramp and exceptional boating opportunities. Gulfstream Shores is ideally situated, offering a tranquil lifestyle just a short drive from Miami and the prestigious Ocean Reef Club.Discover the perfect blend of coastal living and modern comfort.

$1,099,000
Little Torch Key
Jolly Roger Estates   - MM: 28.50
4 Bed, 4 Baths, 1,638 SqFt Days Listed: 35
Duplex - Active - Waterfront Yes
Side of Island: Median - Dockage: Boat Lift70ft.

Stunning Legal Duplex with Unmatched Waterfront Views!Welcome to this exceptional legal duplex, a rare gem on a sprawling corner lot surrounded by water on both sides. Each spacious 2-bedroom, 2-bathroom unit offers its own private patio and dedicated storage--ensuring convenience and comfort for all residents.KEY HIGHLIGHTSPrime Location: End-of-canal setting with room for multiple boats and a pressure induced boat lift, providing direct boating access.Scenic Beauty: Overlooks a serene salt pond preserve, offering breathtaking sunset views from every bedroom. Expansive lot: Gated access for dry boat storage and ample space for all your toys.Built for Resilience: Elevated construction, impact windows, Hardy board siding and a metal roof ensure lasting quality and peace of mind.Investment Potential: Proven rental income history, perfect for savvy investors. In addition, the option for owner/tenant shared occupancy makes for the perfect island getaway by providing a guilt free investment resulting in offset expenses.Experience the ultimate Keys waterfront lifestyle in a property designed for affordability, relaxation, and adventure. Schedule your private tour today!

$1,099,000
Marathon
Flamingo Island   - MM: 49.50
4 Bed, 4 Baths, 2,532 SqFt Days Listed: 120
-8.42% ($101,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This move-in ready 2 story home is located in one of Marathons best neighborhoods. With over 2500 sq. feet, this expansive 4 bedroom 3 bath home is perfect for a large family. The main living area, kitchen, primary suite and 2nd bedroom and guest bath are located upstairs with an interior staircase that leads you downstairs to your den, 2 more bedrooms, bathroom and laundry room. Oversized fenced in yard is perfect for entertaining with lots of room for a pool.New roof, appliances, ADT security system and much more.

$1,095,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,028 SqFt Days Listed: 124
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

Discover the ultimate boaters retreat in beautiful Summerland Key! This stilted canal-front home features 3 bedrooms and 2 baths and easy access to the both the Atlantic Ocean and Gulf of Mexico After a day on the water unwind in the pool or relax under a palm tree in your hammock. The ground-level storage area is perfect for your boating gear and outdoor furniture. A commercial ice maker is ready to chill your catch of the day or beverages for your sandbar excursions.Enjoy the convenience of a Coast Guard-marked channel, providing a safe and enjoyable transit to and from your dock. The wide 60-foot canal makes maneuvering a breeze, and marine fuel is just 2 minutes away by boat--no more long trips to the fuel dock.Inside the home, youll find an open-concept design centered around the kitchen, dining room, and living area. Off the dining room is a screened-in porch, perfect for enjoying happy hour cocktails or taking in another incredible sunset in paradise.This home boasts three generously sized bedrooms and two baths along with a laundry room. Recent upgrades include a new AC system installed in 2022, a new hot water heater in summer 2024, and a new roof added in 2018. The furniture can be sold with the home, making it move-in or rental ready!The home is conveniently located near many stores, restaurants, and other conveniences. This location offers everything you need in tranquil Summerland Key. This home is truly a boaters dream!

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 01-09-2025.
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