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

Total Listings 147
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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: 121
  • 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: 278
  • 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.

$14,500,000 - Islamorada (Upper Matecumbe Key) , FL

  • Beds: 13 Baths: 11
    Type: Single Family Home - MM: 82
  • MLS ID 567181
    Sq Ft: 6,519
  • Community: Unplatted Upper Mate Days on Market: 9
  • Waterfront: Yes - Waterview: Bay Front,Gulf Front
  • 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.

$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: 454
  • 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: 118
  • 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: 82
  • 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: 518
  • 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: 258
  • 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: 346
  • 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: 107
  • 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

$5,400,000 - 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: 2062
  • 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!

$4,700,000 - Islamorada (Plantation Key) , FL

  • Beds: 4 Baths: 4
    Type: Single Family Home - MM: 90
  • MLS ID 566694
    Sq Ft: 5,311
  • Community: Sunshine Estates Days on Market: 63
  • Waterfront: Yes - Waterview: Bay Front,Gulf Front,Open Water
  • Side of Island: Bay/Gulf Dockage: Boat Lift,Boat Slip 100ft.

Situated on a corner parcel, nestled behind gates of lush tropical landscape is this grand bayfront home with a private guest house, two swimming pools, 100 of deep water dockage, boat house and a two car garage. The main home offers three magnificent en-suite bedrooms, spacious living, and dining area with a fireplace, marble & hand painted Cuban Tile floors. The exquisite kitchen features black

$4,499,000 - Islamorada (Plantation Key) , FL

  • Beds: 5 Baths: 5
    Type: Single Family Home - MM: 89
  • MLS ID 565257
    Sq Ft: 3,973
  • Community: Misc Plantation Key Days on Market: 216
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Basin,Boat Lift

Oceanfront estate on desired Old Highway. Great ocean views, and gracious, island-style home with 5 bedrooms & 5.5 baths. Sandy beach and Beautiful double slide pool with waterfall and spacious outdoor entertaining area. Gated entry, paver driveway. Grounds are in the finishing stages and will be a oceanfront beauty when completed.

$4,195,000 - Islamorada (Lower Matecumbe) , FL

  • Beds: 5 Baths: 5
    Type: Single Family Home - MM: 75
  • MLS ID 566261
    Sq Ft: 4,770
  • Community: Mat Ocean Bay Days on Market: 104
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: None

Magnificent Ocean front estate with 150 of beach frontage on almost an acre and a half! Newer construction featuring a wonderful floor plan with 4 bedrooms, 4.5 baths in the main house, tongue and groove wood ceilings, and 8doors. The functional chefs kitchen offers granite counters, 3 ovens, warming drawer and ice maker. The spacious dining room with tray ceilings is just off the kitchen and

$3,750,000 - Islamorada (Windley Key) , FL

  • Beds: 10 Baths: 8
    Type: Single Family Home - MM: 85
  • MLS ID 561920
    Sq Ft: 6,262
  • Community: Unplatted Windley Key Days on Market: 604
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Other Dockage

The Conch, Lobster, Pelican, & Egret at Alligator Reef Luxury Estate. Private, gated estate for corporate or family retreats. CBS homes consist of two 3/2 homes and two 2/2 homes. Enjoy fabulous sunrises & ocean breezes off the observation deck. 2 lrg heated pools, summer kitchens, & tons of privacy for memorable beach-side gatherings in a tropical paradise. EXCELLENT vacation rental history.

$3,585,000 - Islamorada (Lower Matecumbe) , FL

  • Beds: 3 Baths: 3
    Type: Single Family Home - MM: 75
  • MLS ID 565175
    Sq Ft: 3,187
  • Community: Port Antigua Days on Market: 225
  • Waterfront: Yes - Waterview: Bay Front
  • Side of Island: Bay/Gulf Dockage: Boat Lift 100ft. Concrete

ENJOY STUNNING SUNSETS AND 180 DEGREE BAYVIEWS! PROTECTED 100 FT CANAL FRONT DOCKAGE. IMPECCABLY MAINTAINED SPACIOUS 3 BEDROOM 3 BATH HOME WITH HIGH VAULTED CEILING IN LIVINGROOM, GOURMET KITCHEN, AND LOTS OF NATURAL LIGHT WITH VIEW FROM EVERY ROOM. PATIOS ON SECOND AND THIRD FLOOR AND A ROOFTOP SUNDECK. AMENITIES INCLUDE ELEVATOR, 15KW GENERATOR, TACKLE ROOM, GARAGE, CARPORT, OUTDOOR SHOWER, 2

$3,500,000 - Islamorada (Plantation Key) , FL

  • Beds: 5 Baths: 4
    Type: Single Family Home - MM: 86
  • MLS ID 564909
    Sq Ft: 3,900
  • Community: Venetian Shores Days on Market: 260
  • Waterfront: Yes - Waterview: Canal Front
  • Side of Island: Bay/Gulf Dockage: Concrete

This is a property many dream of but few can afford. Upon entering you will find an imposing foyer w. a soaring 2 story ceiling. The staircase leads up to an open concept living area w. Cathedral ceiling, a coral rock fire place & a balcony w. gorgeous views of the Creek. A large granite topped breakfast bar separates the kitchen. There is also a wet bar & a convenient powder room on this level.

$2,950,000 - Islamorada (Upper Matecumbe Key) , FL

  • Beds: 4 Baths: 2
    Type: Single Family Home - MM: 82
  • MLS ID 563387
    Sq Ft: 1,946
  • Community: Unplatted Upper Mate Days on Market: 436
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Davit Pads

End of Season Price Reduction! Located on the Atlantic Ocean in The Heart of Islamorada situated just above the beach for enjoying spectacular sunrises as each day begins. Gated Estate located on the quiet side of the Island .... the Old Highway. Main House features three bedrooms, three baths and expansive waterside patio surrounding the pool, tiki bar, breezy gazebo, and dock.

$2,900,000 - Islamorada (Plantation Key) , FL

  • Beds: 5 Baths: 4
    Type: Single Family Home - MM: 89
  • MLS ID 566990
    Sq Ft: 2,518
  • Community: Indian Harbor Days on Market: 32
  • Waterfront: Yes - Waterview: Bay Front,Open Water
  • Side of Island: Bay/Gulf Dockage:

Enjoy breathtaking sunset vistas and watch dolphins, birds, fish, and manatees play in the crystal clear waters just off the shore of this expansive bayfront property on Plantation Key. The strong concrete home with metal roof features 2 levels with 5 bedrooms, 4 bathrooms, and generous porches.

$2,700,000 - Islamorada (Plantation Key) , FL

  • Beds: 6 Baths: 6
    Type: Single Family Home - MM: 88
  • MLS ID 561497
    Sq Ft: 4,500
  • Community: Plantation Beach Days on Market: 659
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Basin,Boat Lift

REDEVELOPMENT OR FAMILY COMPOUND. 2.86 +/- acre gated estate with stunning open ocean views, boat basin with boat lift and four cottages in Islamorada, FL. This environmentally friendly property has a custom water desalination treatment system; underground utilities, propane for the cottages and two generators which can run all the homes.

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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 04-18-2015.