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

Luxury homes for sale in the Florida Keys are some of the most impressive pieces of real estate in the country.  These beautiful estates are often situated waterfront - directly on either the bay or the ocean, making for homes with stunning views and a peaceful tranquility that is unparalleled in other markets.  It is rare to find homes that exude a level of the highest luxury and sophistication mixed with the feeling of being located on a private oasis of paradise - yet this is exactly what you will find in the Florida Keys.  Luxury properties in the Keys often come equipped with the finest amenities, including boat docks and private beaches, allowing residents a superior lifestyle and quality of life.

Luxury houses in the Florida Keys can be found throughout the market - from Key Largo to Key West.  Properties often include multi-million dollar estates and private islands.  Those looking to purchase a luxury estate in the Keys have a wealth of choices in one of the most beautiful places in the country!

Total Listings 685
Summerland Key
$26,500,000 7,000 (SqFt)
  • 6
  • 6
  • Single Family

1300 Sunset Boulevard
Summerland, FL 33042

Snug Harbor Subdivision   Waterfront: Yes MM: 25
Side of Island: Ocean
Dockage: Boat Lift300ft.Concr

Summerland Key, glorious sunset views, unique architectural design, elegant and warm, tastefully decorated with the colors of the ocean,multiple living areas, chefs kitchen indoor and out, wine closet, 6 bedrooms/6 baths, guest house, infinity pool, hot tub and swim up bar, 100 ft of protected dockage with 2 boat lifts, private boat ramp, sandy beach, man cave, tackle room a and gym. More, more,
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Lower Matecumbe
$19,000,000 1,500 (SqFt)
  • 2
  • 2
  • Single Family

100 Sapodilla Drive
ISLAMORADA, FL 33036

Mat Sandy Beach   Waterfront: Yes MM: 76
Side of Island: Bay/Gulf
Dockage: Concrete

The Parmelee Estate is a well-maintained yet undeveloped Islamorada haven with an island at its center. The 40-acre property is situated on the bayside of Lower Matecumbe Key and is accessed by way of a private road. Owned by the same family since the 1950s , the parcel is ensconced in 4,000 Jamaica Tall and Maypan coconut palms, silver and green buttonwoods and other native plants that the
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Upper Matecumbe Key Islamorada
$14,500,000 6,519 (SqFt)
  • 13
  • 11
  • Single Family

82910 Overseas Highway
ISLAMORADA, FL 33036

Unplatted Upper Mate   Waterfront: Yes MM: 82
Side of Island: Bay/Gulf
Dockage: Basin

From the private picturesque setting, this 6.41 acre bay front estate offers over 12,400 square feet of living space including a main residence and two guest cottages. This estate features charming Key West style architecture, intimate garden courtyards, balconies and spacious patios overlooking a bay front pool/spa with cabana...
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Key West
$12,500,000 17,500 (SqFt)
  • 5
  • 5
  • Single Family

808 Southard Street
KEY WEST, FL 33040

Old Town Unlisted   Waterfront: No MM: 0
Side of Island: Median
Dockage: None

Historic Harris School plus 6 lots and 5 ROGO units for sale. 2 story Indian Block structure built as one of the first schools in Florida. Situated on a 2 acre lot in the center of Old Town in the Solares Hill area. 3 blocks to Duval St., 5 blocks to Historic Seaport District. This unique offering does not occur in Key West often. Original classrooms boast 14 ft. ceilings (both floors). Grand staircases, lots of wood on interior of building. HNC-2 Zoning allows for residential, multi-family, offices, light commercial use, group homes, medical facilities and more. There are 7 lots (6 along Carstens Lane) with 5 ROGO units. Possible private compound use or just single family construction. Will finance with 30% down & market rates
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Little Torch Key
$10,900,000 1,920 (SqFt)
  • 4
  • 3
  • Single Family

1 Hopkins Island Drive
OTHER, FL 33042

Misc Little Torch Ke   Waterfront: Yes MM: 27
Side of Island: Ocean
Dockage: Basin

Just 25 minutes from Key West and Marathon awaits Hopkins Island, a private offshore island with its lush 11.25 acres on the Atlantic with next door exclusive neighbor Little Palm Island, a gourmet meal is a boat ride away. Snorkeling in neighboring Looe Key National Marine Sanctuary could be your next hobby. With a grassy inland area to accommodate several helicopters or the interior hidden basin with extensive dock space provides a haven from waves, storms and wandering eyes just 2.5 miles offshore no one will know youre home relaxing and enjoying life to the fullest. Caribbean style furnishings and island equipment included. Rare private island.
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Marathon
$9,900,000 2,304 (SqFt)
  • 4
  • 3
  • Off Shore Isl

East Sister Rock
MARATHON, FL 33050

Misc Sombrero Area   Waterfront: Yes MM: 50
Side of Island: Ocean
Dockage: n/a

PRIVATE ISLAND in Hawk Channel off the coast of Marathon. Self sufficient with power supplied by Solar Panels, Wind Mill and back up Generator. Island surrounded by moat with boat docks. Guest house. Main house has wrap around porch/deck under roof, 10 ceilings, 3 bedrooms, pine floors, fireplace, granite & stainless kitchen. Has Heli-pad for the short hop from the Marathon Airport.
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Key West
$8,400,000 10,822 (SqFt)
  • 5
  • 4
  • Single Family

620 Southard Street
KEY WEST, FL 33040

Old Town Unrecord   Waterfront: No MM: 1
Side of Island: Median
Dockage: None

The Lowe Mansion has been relisted. It is a once in a lifetime opportunity. This home has not been offered for sale in over three decades. This majestic property stands alone in its beauty,historical significance,and quality of renovation. The privacy of this property is unparalleled. It sits on one of the largest parcels of land in Old Town amidst a magnificent tropical garden atop Solaris Hill, the highest point on the island. The estate includes the main house,private guest or caretakers house,large studio,conservatories,and numerous other structures. This opportunity is for those who desire the finest. Qualified individuals please request additional information on the home, and discuss scheduling of showings.
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Plantation Key
$7,950,000 1,243 (SqFt)
  • 3
  • 3
  • Single Family

89251 Old Highway
ISLAMORADA, FL 33070

Trop Coral Reef   Waterfront: Yes MM: 89
Side of Island: Ocean
Dockage: Boat Lift,Davits200f

Private and gated, this exquisite long-driveway Oceanfront Estate with over 450 waterfrontage & deep water dockage, set on over 6 acres including bay bottom is offered for the first time in decades. Pristine beachfront cabin with wide water views from the oceanfront porch built in the 1930s with additions in 2005-06. Three bedrooms, three baths, outside shower, garage, downstairs storage.
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Upper Matecumbe Key Islamorada
$7,500,000 3,443 (SqFt)
  • 4
  • 3
  • Single Family

82500 Old State Road
ISLAMORADA, FL 33036

Strattons   Waterfront: Yes MM: 83
Side of Island: Ocean
Dockage: Boat Ramp

Prime location in the heart of Islamorada. Oceanfront 4 bedroom, 3 bath completed residence with 7 additional building rights on this 2.65 acre property. Pool, spa, dock and tennis court. Create your own subdivision or family compound. Privacy and open water Atlantic Ocean views. Walk or bike to restaurants, art galleries, shopping. World-class sport fishing, diving, kayaking, paddle boarding.
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Key West
$7,400,000 5,717 (SqFt)
  • 7
  • 7
  • Single Family

1017 Southard Street
KEY WEST, FL 33040

Old Town Unlisted   Waterfront: No MM: 1
Side of Island: Median
Dockage: None

This is perhaps the finest luxury estate in Key West. It encompasses over 20,000 square feet of land and over 5,000 square feet of living space in the heart of the historic district. The spectacular Queen Anne mansion, circa 1890, is complimented by three additional buildings: a pool house with one bedroom and an indoor/outdoor bath, a garage with an upstairs apartment, and a two bedroom/two bath guest home. The historic residence features a master suite on each floor, a stunning octagonal living room, soaring ceilings, and custom painted Dade County pine walls and floors. In the center of the estate, the hand tiled pool sparkles among mature tropical landscaping with spectacular banyan and royal poinciana trees.
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Plantation Key
$6,498,000 3,640 (SqFt)
  • 5
  • 3
  • Multi-Units

88835 Old Highway
ISLAMORADA, FL 33070

Pearl City   Waterfront: Yes MM: 89
Side of Island: Ocean
Dockage: Basin,Boat Ramp

Stunning Millionaires Row estate consisting of 6.78 acres of prime oceanfront property with 1.16 acres submerged with 200 x 70 protect boat basin and boat ramp. With 5 permitted homes, this property is ideal for multi home development, corporate, or large family compound where guest privacy and pleasure are priority. More...
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Plantation Key
$6,000,000 7,855 (SqFt)
  • 6
  • 7
  • Single Family

87961 Old Highway
ISLAMORADA, FL 33036

Plantation Beach   Waterfront: Yes MM: 88
Side of Island: Ocean
Dockage: None

Rare opportunity!Oceanfront estate with 4 acre and over 300 ft of ocean frontage in the fishing capital of the world.The estate has 6 bedroom and 7 baths with a indoor pool and hot tub.The main house has a open floor plan with open water views from every room .The house is easy to show and comes fully furnished.Also the adjacent property 87963 is for sale for an additional price.
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Upper Matecumbe Key Islamorada
$5,950,000 959 (SqFt)
  • 2
  • 2
  • Single Family

101 CARROLL Street
ISLAMORADA, FL 33036

Strattons   Waterfront: Yes MM: 83
Side of Island: Ocean
Dockage: None

Located oceanfront in downtown Islamorada, the historical Gilmore Estate is locally known as the Bay Bourne Houseboat. Situated on 5+ acres, with 300 feet of beach, the Houseboat is an actual 60 foot 1948 Chris Craft with 1 stateroom, 2 baths, a galley kitchen, salon, on the first deck. Top deck consists of a 4-bunk stateroom and private upper deck with wide open ocean views!
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Sugarloaf Key
$5,900,000 3,340 (SqFt)
  • 7
  • 6

15620 Old State 4A Road
OTHER, FL 33042

Sugarloaf Shores   Waterfront: Yes MM: 16
Side of Island: Ocean
Dockage: Boat Lift

Remarkable gated and totally private 3.7 acre estate on 350 feet of natural white sandy beach on Atlantic Ocean. Nothing between you and Cuba except 90 miles of pristine ocean and American Shoal Lighthouse. Main house is a beautifully updated 1800 sq. ft., 3 bedroom, 2 bath modern island home with 2 guest cottages. Magnificent 500 ft. dock with a 45,000 lb. boat lift with 4.5 feet of water. Spectacular custom rock pool with waterfall grotto, complete with pool bar. Transient Licenses allow for exclusive vacation rentals which make this a great investment. International Airport nearby.
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Sugarloaf Key
$5,900,000 3,340 (SqFt)
  • 7
  • 6

15620 Old State 4A Road
OTHER, FL 33042

Sugarloaf Shores   Waterfront: Yes MM: 16
Side of Island: Ocean
Dockage: Boat Lift

3 Transient Homes - Remarkable gated and totally private 3.7 acre estate on 350 feet of natural white sandy beach on Atlantic Ocean. Nothing between you and Cuba except 90 miles of pristine ocean and American Shoal Lighthouse. Main house is a beautifully updated 1800 sq. ft., 3 bedroom, 2 bath modern island home with 2 guest cottages. Magnificent 500 ft. dock with a 45,000 lb. boat lift with 4.5 feet of water. Spectacular custom rock pool with waterfall grotto, complete with pool bar. Transient Licenses allow for exclusive vacation rentals which make this a great investment. International Airport nearby.
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Key West
$5,500,000 2,987 (SqFt)
  • 3
  • 2
  • Single Family

5 Sunset Key Drive
KEY WEST, FL 33040

Sunset Key   Waterfront: Yes MM: 0
Side of Island: Bay/Gulf
Dockage: Dock Privileges,Firs

Recently listed waterfront residence on world famous Sunset Key. This waterfront beach house makes for the perfect island getaway. Located directly on the Beach with an unbelievable view of the open ocean and surrounding keys. This residence has three bedrooms with two and a half baths. The downstairs master bedroom has doors leading out to the pool area and the beach. Imagine living on your own secluded island, but being only three minutes from historic downtown Key West accessible only by an island ferry which runs 24 hours a day. On Sunset Key Island, there are no cars and no parking problems, only quiet island living with plenty of beaches, tennis courts, and resort amenities. Come see this incredible beachfront residence.
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Key Largo
$5,500,000 2,590 (SqFt)
  • 4
  • 2
  • Single Family

11175 County Road 905
KEY LARGO, FL 33037

Cardsound Point 1   Waterfront: Yes MM: 905
Side of Island: Ocean
Dockage: Basin,Boat Ramp,Davi

Ocean Front Estate 2 story CBS home with Old Florida charm located between Key Largo and Ocean Reef on over 2 acres, has over 500 feet of direct ocean front, and panoramic ocean views from almost every room! Enjoy the private beach, pier, tarpon fishing and large boat basin with a boat lift for docking your boat. This spacious home has 4 BR including a master suite on the main living level.
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Windley Key
$5,400,000 1,839 (SqFt)
  • 3
  • 2
  • Single Family

85261 Old Highway
ISLAMORADA, FL 33036

Unplatted Windley Key   Waterfront: Yes MM: 88
Side of Island: Ocean
Dockage: Basin,Boat Ramp

HUGE OCEANFRONT PARCEL JUST UNDER 3 ACRES IN ISLAMORADA, large deep water basin! 200 on the ocean! You will enjoy this gated compound with a ground level home with many extras including fireplace and home theater screen. Large deck to enjoy the unobstructed oceanviews. This is a rare and unique property!
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Key West
$5,400,000 3,416 (SqFt)
  • 4
  • 4
  • Single Family

20 Sunset Key Drive
KEY WEST, FL 33040

Sunset Key   Waterfront: Yes MM: 0
Side of Island: Ocean
Dockage: None

Located on the prestigious private island of Sunset Key, just 5 minutes from Key West, by launch, sits a custom built ocean front 3,416 sq.ft. compound. In the main house, on the first level you are awed by incredible views of the Atlantic. Features include dramatically high coffered ceilings, custom moldings, wood flooring, and spacious open living areas. A second floor master suite includes a sitting room, spa-sized bath, and dressing room. A pergola connects the guest cottage with the main house accented by lush tropical landscaping, free form pool, water feature and spa. The private two story guest house includes 2 bedrooms and 2 baths with the same attention to detail. Beach, spa, gym and a gourmet restaurant are there for you.
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Key West
$5,300,000 2,804 (SqFt)
  • 3
  • 3
  • Single Family

33 Sunset Key Drive
KEY WEST, FL 33040

Sunset Key   Waterfront: Yes MM: 0
Side of Island: Bay/Gulf
Dockage: Dock Privileges,Firs

Unbelievable three bedroom Waterfront residence on an oversized lot. Incredible views of Key West Harbor from the private waterfront pool and open balcony. Attention to detail was not overlooked in the construction of this private island residence. Sip your favorite beverage while watching the tall ships sail past on their way to their Sunset Celebration cruises or Swim in the refreshing clear blue waters from any of the three beaches within walking distance to this home. Tennis Courts, a Gourmet Restaurant, and many more features give homeowners and their guests a remarkable living experience. City utilities and services, island ferry running 24 hours a day, and other conveniences make this place a modern island paradise
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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 07-30-2015.

Shoreline Properties
92300 Overseas Hwy Suite 303
Tavernier, Florida 33070

1(800) 692-3605
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