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

Total Listings 1,143
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$1,348,000
Marathon
Sheryl Subdivision   - MM: 50.50
3 Bed, 3 Baths, 1,808 SqFt Days Listed: 227
-8.92% ($132,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 38ft.Rip Rap

WELCOME to paradise in the sun located in the heart of Marathon! This stunning 3 bed / 2 bath, over 1800 sq ft. oasis will not disappoint. Located just 3 homes away from the open ocean, this beauty provides both indoor and outdoor entertainment. The gorgeous kitchen will satisfy the most talented chef. The open concept also provides a great space for family and friends. Updated throughout to satisfy your pickiest buyer. Enjoy the privacy of a master bedroom located on the 2nd floor. If youre looking for the LOWEST PRICE per sq ft waterfront property in Marathon, you are here. If your goal is to live mortgage free this one provides family living as well as income potential as it is a seasoned rental on AIRBNB. Private balcony on the 2nd and a private balcony on the 3rd floor as well. The porch area outside the main entrance provides for relaxing nights. The bonus room located at ground level with ample space is a huge plus, the private open space is perfect for relaxing after those long and beautiful days in that blue water. HURRY this is a MUST see, schedule your private showing before this one is gone!

$1,325,000
Key Largo
Pirates Cove   - MM: 98.50
3 Bed, 3 Baths, 1,350 SqFt Days Listed: 215
-9.68% ($142,000) 2 Price Changes : Last Change 76 Days Ago
Single Family - Contingent - 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: 72
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: 66
-7.14% ($100,000) 1 Price Change : Last Change 30 Days Ago
Single Family - Contingent - 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: 60
-6.81% ($95,000) 1 Price Change : Last Change 23 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits

MULTI FAMILY OPPORTUNITY! Water view from every floor! 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 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: 185
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
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
3 Bed, 3 Baths, 960 SqFt Days Listed: 2
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!

$1,300,000
Key West
Pearlman Heights   - MM: 4.00
5 Bed, 5 Baths, 2,016 SqFt Days Listed: 41
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.A Matterport virtual tour has just been added to be viewed

$1,299,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
4 Bed, 4 Baths, 2,448 SqFt Days Listed: 164
-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
Little Torch Key
Jolly Roger Estates   - MM: 28.50
3 Bed, 3 Baths, 2,392 SqFt Days Listed: 439
-25.77% ($451,000) 4 Price Changes : Last Change 112 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 80ft.

Spacious canal front home in desirable Jolly Roger Estates on Little Torch Key! No details were spared in the recent renovation transformation, resulting in impeccable design and comfort, and the result is a serene and comforting destination, perfect for family getaways or as an income generating investment property. Kitchen updates include stainless steel appliances and granite countertops, making for a wonderful culinary experience. The split floor plan allows for tranquil privacy in both lower bedrooms. The spacious loft overlooks the living area and adds versatility and extra space for family or guests. Structural features include impact doors and windows throughout, and sturdy metal roof. An 80 dock (newly renovated with swim ladder) ensures plenty of room for your boat and there are no bridges to open water, making for a quick trip to world class fishing, diving and Looe Key Reef. Relax and enjoy the clear, clean flow-through canal view from the covered porch or the tiki hut. Owner financing will be considered.

$1,299,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 943 SqFt Days Listed: 31
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Location, Location, Location! Old Town in X-Flood Zone on Solaris Hill with Off Street Parking! Quintessential conch cottage has a cozy front porch & has been in the same family for decades. All wood structure shows a glimpse of wood boards behind the existing interior paneling. This is believed to be the much-desired Dade County Pine. Roof and main electrical panel replaced (w/ permits) in 2014. House is currently configured as seven rooms in total (3 bed, 1 bath, den, dining & kitchen). Front yard provides the highly coveted Off-Street-Parking & the back yard is 31 Ft X 26 Ft (total 806 sq ft). House is a renovation project. This is an estate sale & there will be NO repair and NO clean up by the sellers. However, there will be NO waiting on Probate & NO court approvals needed. Make 719 Elizabeth St your Old Town Island Oasis!

$1,299,000
Key West
Riviera Shr Amd Plat   - MM: 3.00
5 Bed, 5 Baths, 2,005 SqFt Days Listed: 9
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

PRICED TO SELL! This expansive 5-bedroom, 3-bathroom home is situated on a giant lot and offers a host of premium features, including a huge pool, outdoor kitchen, detached studio/office, and a mother-in-law lockout suite. With a neutral palette that exudes elegance and serenity, this home combines aesthetic charm with durable construction. Built to last, this home is protected with impact windows and doors, a sturdy metal roof, and solid concrete block construction, offering you peace of mind.The main house consists of 3 bedroom and 2 baths. Directly off the kitchen, youll find the perfect space for entertaining or relaxation--- a covered lanai with an outdoor kitchen that overlooks a luxurious sizable pool. A convenient pool shower is nearby, and a mudroom is thoughtfully positioned just off the pool, making post-swim clean-up a breeze. The mother-in-law lockout suite which includes 2 bedrooms and 1 bath offers privacy for your guests or can serve as a fantastic rental income opportunity. In addition to the mother-in-law suite is a detached studio ideal for a home office, art studio, or yoga room.The fully fenced yard is lined with lush tropical fruit trees, adding to the island charm. With off-street parking, a large garage, and ample storage space, this home is equipped to store all your toys, tools and more. Centrally located, this home provides the perfect balance--insulated from the island commotion, yet just minutes from shopping, schools, beaches, and a short bike ride to Old Town Key West. Additionally, its situated next to one of the islands rare nature preserves, giving you direct access to peaceful trails and beautiful natural surroundings. Dont miss out on this extraordinary opportunity piece of paradise which has it all.

$1,299,000
Big Pine Key
Whispering Pines   - MM: 30.50
3 Bed, 3 Baths, 1,043 SqFt Days Listed: 9
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

This newly remodeled 2-bedroom, 1-bathroom home is perfectly positioned on two spacious lots in the heart of Big Pine Key, offering over 20,000 sq ft of land and an incredible 297 feet of waterfront. With 75 feet of concrete dockage and quick access to the ocean via Spanish Harbor Channel, this is a boaters dream come true.Inside, enjoy peace of mind with impact-rated windows and doors, a sturdy metal roof, and stylish modern finishes throughout. Outside, theres plenty of room to expand, entertain, or simply relax and soak in the serene Keys lifestyle.Located just minutes from shopping, dining, and Big Pine Community Park, this home combines privacy and convenience in one of the Lower Keys most desirable neighborhoods.

$1,299,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,380 SqFt Days Listed: 79
-7.21% ($100,900) 3 Price Changes : Last Change 11 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

The COPPER TOP - Solid construction with a metal roof located on a beautiful flow-through canal in Summerland Key Cove. This 3 bedroom, 2 bath home checks all the boxes. Youll love the modern remodeled kitchen with vaulted ceilings in the living area, tiled floors throughout and a screened in balcony that allows you to open up the house and enjoy the breezes. Furnished for your convenience so you can be fishing in no time.Downstairs the amenities include a tiki, boat lift and you even have your own boat ramp! Plenty of room for parking under the house or in the yard - room for an RV. 10,000 pound boat lift installed in 2024. Outdoor shower. A concrete block storage room holds your gear.Dont miss the boat on this one!

$1,299,000
Long Key
Long Key Estates   - MM: 68.00
3 Bed, 3 Baths, 1,607 SqFt Days Listed: 76
-5.53% ($76,000) 1 Price Change : Last Change 22 Days Ago
Single Family - Contingent - 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.

$1,299,000
Key West
Old Town Unlisted   - MM: 1.00
2 Bed, 2 Baths, 952 SqFt Days Listed: 34
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This beautifully renovated home greets you with a charming front porch perfect for enjoying the serenity of lane living. Step inside and you will find gorgeous vaulted ceilings and an open floor plan with top of the line finishes throughout. Custom cabinetry, quartz counters and stainless appliance package finish the open concept kitchen with bar seating. New electric, plumbing, impact windows/doors, ductless a/c, dehumifiers and a new metal roof ensure peace of mind for many years. The main level has a bedroom and full bath and the 2nd level is private to the primary suite. The backyard is an open canvas for your own ideas and currently finished in composite decking and covered by a custom awning complete with electrical for overhead ceiling fans. If you are seeking a no hassle Key West retreat the house is also available turnkey furnished. Stump Lane runs from Frances to White Street and you can both drive and park on this lane.

$1,299,000
Key West
Key West Realty Cos Subdivisi   - MM: 3.00
3 Bed, 3 Baths, 1,232 SqFt Days Listed: 15
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Wake up and smell the coffee! You should have bought ten years ago? You are going to say that again ten years from now! This is the house to buy because it has everything you want. Three bedroom two bathroom upstairs and ample useable space downstairs, plus a two car garage, plus off street parking, plus a huge privacy wall, plus a large pool, plus a pool house bar with a full kitchen in it! This is a very well built solid all concrete home that will continue to stand the tests of time and storms. It is located in an excellent neighborhood with a dog park just down the street. Stop saying you should have and say you are now. Call for a showing. More photos to come.

$1,299,000
Key West
New Town Unlisted   - MM: 2.00
3 Bed, 3 Baths, 1,850 SqFt Days Listed: 149
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Rare opportunity to purchase a stunning, only 7-year-old, 3 bedroom, 2 and 1/2 bath, 1,850 square foot, elevated home that is centrally located on the island. The Enclave on Riviera is a gated community that was built to the highest levels of the Florida Green building standards and includes a pool (complete with Tiki Hut!) and private access to kayaking and paddleboarding on the Riviera canal. The association is comprised of only 11 homeowners, yet the grounds are spacious as they include a protected conservation area that cannot ever be built upon. The home features an open floor plan with a gourmet kitchen, stainless steel appliances, quartz counter tops, center island and breakfast bar. There is also a large laundry room/pantry and half bath on the main living level. Upstairs you will find 2 guest rooms, guest bath, custom storage cabinets and the primary bedroom with bath ensuite, generous shower, commode room, and walk in closet. The elevated structure, impact windows and doors as well as impact Bahama shutters make for reasonable insurance costs. Most furniture is included, the air conditioning is brand new (2024) and upgrades include Toto toilets, Smart thermostat, Blink and Ring security systems, metal railings, completely screened in porches, garbage disposal (2022), and more.This home is unique in that it is away from the other homes in the community and laid out with two huge 300 square foot screened in porches that span the entire length of the home both upstairs and downstairs. Imagine yourself entertaining or unwinding as you take in the tranquil view overlooking the mangroves toward the Riviera Canal. There is also a garage and three car covered parking for all of your toys. This is stress-free living with a reasonable monthly association fee of $425 that covers the common area maintenance, security gates, landscaping, and pool service. This one really does tick all the boxes.

$1,299,000
Ramrod Key
Ramrod Shores Marina   - MM: 27.00
3 Bed, 3 Baths, 2,081 SqFt Days Listed: 139
-3.71% ($50,000) 1 Price Change : Last Change 90 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

**Stunning 3-Bedroom, 2-Bath Home on 15,000 Sq Ft Lot with Resort-Style Pool and Spa**Welcome to your dream home! This spacious 3-bedroom, 2-bathroom property offers everything you need for comfortable living and entertaining. Nestled on a generous 15,000 sq ft lot, youll enjoy plenty of space both indoors and outdoors. The centerpiece of this property is the luxurious resort-style pool with a large spa--perfect for relaxing or hosting guests. The expansive paver driveway leads to a massive storage area, providing ample room for all your toys, tools, and more. Whether youre enjoying the sunny outdoors or relaxing inside, this home offers the perfect balance of style, space, and convenience. Dont miss the opportunity to own this incredible property with plenty of room to grow and entertain!

$1,299,000
Big Pine Key
Kyle Dyre   - MM: 28.00
3 Bed, 3 Baths, 1,440 SqFt Days Listed: 51
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.

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 05-03-2025.
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