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 938
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$19,000,000 - Islamorada (Lower Matecumbe) , FL

  • Beds: 2 Baths: 2
    Type: Single Family Home - MM: 76
  • MLS ID 566119
    Sq Ft: 1,500
  • Community: Mat Sandy Beach Days on Market: 99
  • Waterfront: Yes - Waterview: Bay Front,Gulf Front,Open Water
  • 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

$16,000,000 - Islamorada (Upper Matecumbe Key) , FL

  • Beds: 6 Baths: 7
    Type: Single Family Home - MM: 82
  • MLS ID 564784
    Sq Ft: 7,522
  • Community: Palm Harbor Days on Market: 256
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Basin,Boat Lift,Boat Ramp,Davits 500ft.

Ultra private and secluded waterfront estate on 6.5 acres with expansive dockage, private boat basin, ramp, lifts and davits. Principal house with 4BR/5.5BA and separate 2/2 guest house. Multiple indoor/outdoor entertaining areas and true chefs kitchen with Carrara marble countertops. Hardwood floors throughout. Lush tropical gardens designed by Raymond Jungles with oversized pool and spa.

$12,500,000 - Key West, FL

  • Beds: 5 Baths: 5
    Type: Single Family Home - MM: 0
  • MLS ID 120731
    Sq Ft: 17,500
  • Community: Old Town Unlisted Days on Market: 110
  • Waterfront: No
  • 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

$10,900,000 - Other (Little Torch Key) , FL

  • Beds: 4 Baths: 3
    Type: Single Family Home - MM: 27
  • MLS ID 120182
    Sq Ft: 1,920
  • Community: Misc Little Torch Ke Days on Market: 235
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Basin

Just 25 minutes from Key West and Marathon awaits Hopkins 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.

$9,900,000 - Marathon, FL

  • Beds: 4 Baths: 3
    Type: Off Shore Island - MM: 50
  • MLS ID 566094
    Sq Ft: 2,304
  • Community: Misc Sombrero Area Days on Market: 102
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage:

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.

$9,600,000 - Key West, FL

  • Beds: 5 Baths: 4
    Type: Single Family Home - MM: 1
  • MLS ID 121099
    Sq Ft: 10,822
  • Community: Old Town Unrecord Days on Market: 50
  • Waterfront: No
  • 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.

$9,000,000 - Islamorada (Plantation Key) , FL

  • Beds: 9 Baths: 9
    Type: Single Family Home - MM: 89
  • MLS ID 562950
    Sq Ft: 5,633
  • Community: Trop Coral Reef Days on Market: 457
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Other Dockage

Schooner Bay EstatesOverlooking the clear blue waters surrounding Islamorada in the Florida Keys is this 2.87 acre gated beachfront estate. This stunning private residence features lush tropical foliage with 3 oceanfront homes, 2 pools, and 3 docks. Boasting 394 feet of private white sand beach it offers 8 bedrooms/6.5 baths with expansive private balconies and amazing ocean views.

$9,000,000 - Islamorada (Plantation Key) , FL

  • Beds: 9 Baths: 9
    Type: Single Family Home - MM: 88
  • MLS ID 119169
    Sq Ft: 7,855
  • Community: Plantation Beach Days on Market: 432
  • Waterfront: Yes - Waterview: Canal Front,Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Basin,Boat Lift Other

Rare opportunity!Oceanfront estate with 6.5 acres and over 300 ft of ocean frontage in the fishing capital of the world.The estate has 9 bedroom and 9 baths with a indoor and outdoor pool.Theres is a boat basin with two boat lifts and a concrete sea wall for all the toys.The property has a tiki hut on the open water and a light house.The main house has a open floor plan with open water views from every room .There is also a guest house with a great sun deck overlooking the open water .The house is easy to show and comes fully furnished.Sale includes adjacent property, 87963 Old Hwy.

$7,950,000 - Islamorada (Plantation Key) , FL

  • Beds: 3 Baths: 3
    Type: Single Family Home - MM: 89
  • MLS ID 566146
    Sq Ft: 1,243
  • Community: Trop Coral Reef Days on Market: 96
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Boat Lift,Davits 200ft.

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.

$7,500,000 - Islamorada (Upper Matecumbe Key) , FL

  • Beds: 4 Baths: 3
    Type: Single Family Home - MM: 83
  • MLS ID 566504
    Sq Ft: 3,443
  • Community: Strattons Days on Market: 60
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • 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.

$6,498,000 - Islamorada (Plantation Key) , FL

  • Beds: 5 Baths: 3
    Type: Multi-units - MM: 89
  • MLS ID 562582
    Sq Ft: 3,640
  • Community: Pearl City Days on Market: 496
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • 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...

$6,000,000 - Islamorada (Plantation Key) , FL

  • Beds: 6 Baths: 7
    Type: Single Family Home - MM: 88
  • MLS ID 120169
    Sq Ft: 7,855
  • Community: Plantation Beach Days on Market: 236
  • Waterfront: Yes - Waterview: Canal Front,Oceanfront,Open Water
  • 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.

$5,950,000 - Islamorada (Upper Matecumbe Key) , FL

  • Beds: 2 Baths: 2
    Type: Single Family Home - MM: 83
  • MLS ID 564240
    Sq Ft: 959
  • Community: Strattons Days on Market: 324
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • 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!

$5,950,000 - Islamorada (Upper Matecumbe Key) , FL

  • Beds: 4 Baths: 5
    Type: Single Family Home - MM: 82
  • MLS ID 566231
    Sq Ft: 6,422
  • Community: Misc Upper Matacumbe Days on Market: 85
  • Waterfront: Yes - Waterview: Bay Front,Gulf Front,Open Water
  • Side of Island: Bay/Gulf Dockage: Basin,Davits Concrete

The finest of the bay front parcels in the heart of Islamorada! Peaceful, private, gated estate situated on 1.5+ acres with expansive bay views and gorgeous sunsets. Featuring 4 BR/5 BA, office, media room, exercise room, 2 elevators, impact windows and doors, all marble floors, tall ceilings and doors, swimming pool, and a deep water boat basin to accommodate several large boats. A separate

$5,900,000 - Marathon (Grassy Key) , FL

  • Beds: 10 Baths: 12
    Type: Single Family Home - MM: 58
  • MLS ID 566864
    Sq Ft: 12,378
  • Community: Crains Subdivision Days on Market: 25
  • Waterfront: Yes - Waterview: Oceanfront
  • Side of Island: Ocean Dockage: None

Unparalleled and unique, this stunning Florida Keys estate is remarkable in every way. Like butterflies, the beautiful creatures they are named for, Mariposa and Papillion comprise twin Contemporary residences on a 2-acre + estate-sized parcel with over 240 feet of sandy beachfront on the glorious multi-hued waters of the Atlantic Ocean. Designed and built by the owner/architect,

$5,900,000 - Other (Sugarloaf Key) , FL

  • Beds: 7 Baths: 6
    Type: - MM: 16
  • MLS ID 121103
    Sq Ft: 3,340
  • Community: Sugarloaf Shores Days on Market: 50
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • 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.

$5,900,000 - Other (Sugarloaf Key) , FL

  • Beds: 7 Baths: 6
    Type: - MM: 16
  • MLS ID 121129
    Sq Ft: 3,340
  • Community: Sugarloaf Shores Days on Market: 46
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • 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.

$5,749,000 - Key West, FL

  • Beds: 4 Baths: 4
    Type: Single Family Home - MM: 0
  • MLS ID 119748
    Sq Ft: 3,416
  • Community: Sunset Key Days on Market: 331
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • 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.

$5,500,000 - Key West, FL

  • Beds: 3 Baths: 2
    Type: Single Family Home - MM: 0
  • MLS ID 119858
    Sq Ft: 2,987
  • Community: Sunset Key Days on Market: 304
  • Waterfront: Yes - Waterview: Gulf Front,Oceanfront,Open Water
  • Side of Island: Bay/Gulf Dockage: Dock Privileges,First Come Dock,Other Dockage

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.

$5,400,000 - Islamorada (Windley Key) , FL

  • Beds: 3 Baths: 2
    Type: Single Family Home - MM: 85
  • MLS ID 549574
    Sq Ft: 1,839
  • Community: Windley Key Mobile Home Park Condominiums Days on Market: 2040
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Basin,Boat Ramp

HUGE OCEANFRONT PARCEL IN ISLAMORADA offering a deep water basin...rare for oceanfront! 200 on the ocean! You will enjoy this gated compound with a remodeled 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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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 03-27-2015.