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

Total Listings 112
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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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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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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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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Plantation Key
$4,499,000 3,973 (SqFt)
  • 5
  • 5
  • Single Family

89401 Old Highway
ISLAMORADA, FL 33070

Misc Plantation Key   Waterfront: Yes MM: 89
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.
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Plantation Key
$4,000,000 4,103 (SqFt)
  • 4
  • 3
  • Single Family

88547 Old Highway
ISLAMORADA, FL 33070

Key Heights   Waterfront: Yes MM: 89
Side of Island: Ocean
Dockage: Boat Lift,Davits400f

Open Oceanfront Estate on coveted Millionaires Row! The 4BD/3BA home is tucked away on 1.5 acres of native landscaping down the long whimsical driveway, and one of the only Islamorada properties boasting a 400 pier which has been recently re-decked.The sandy backyard protected by new concrete seawall, pool is recast and inviting. This is definitely a play house not to be missed!
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Lower Matecumbe
$3,999,999 4,770 (SqFt)
  • 5
  • 5
  • Single Family

75931 Overseas Highway
ISLAMORADA, FL 33036

Mat Ocean Bay   Waterfront: Yes MM: 75
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
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Plantation Key
$3,999,999 5,311 (SqFt)
  • 4
  • 4
  • Single Family

150 Redwing Road
ISLAMORADA, FL 33070

Sunshine Estates   Waterfront: Yes MM: 90
Side of Island: Bay/Gulf
Dockage: Boat Lift,Boat Slip1

Situated on a corner parcel with over 480 of water frontage, nestled behind gates of lush tropical landscape is this grand bay front 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.
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Windley Key
$3,750,000 6,262 (SqFt)
  • 10
  • 8
  • Single Family

84775 Old Highway
ISLAMORADA, FL 33036

Unplatted Windley Key   Waterfront: Yes MM: 85
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.
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Lower Matecumbe
$3,585,000 3,187 (SqFt)
  • 3
  • 3
  • Single Family

248 COSTA BRAVO Drive
ISLAMORADA, FL 33036

Port Antigua   Waterfront: Yes MM: 75
Side of Island: Bay/Gulf
Dockage: Boat Lift100ft.Concr

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
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Plantation Key
$3,500,000 3,900 (SqFt)
  • 5
  • 4
  • Single Family

160 Stromboli Drive
ISLAMORADA, FL 33036

Venetian Shores   Waterfront: Yes MM: 86
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.
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Upper Matecumbe Key Islamorada
$2,950,000 1,946 (SqFt)
  • 4
  • 2
  • Single Family

81145 OLD Highway
ISLAMORADA, FL 33036

Unplatted Upper Mate   Waterfront: Yes MM: 82
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.
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Plantation Key
$2,700,000 3,366 (SqFt)
  • 4
  • 4
  • Single Family

906 VENETIAN Boulevard
ISLAMORADA, FL 33036

Venetian Shores   Waterfront: Yes MM: 86
Side of Island: Bay/Gulf
Dockage: Davits100ft.

Beautiful home in Venetian Shores. Amazing bay views. 100 ft. dock with deep-water dockage. 4 bedroom 4 bathroom. Large storage room. Large open kitchen with stainless steel appliances and granite counters.Video Link:https://youtu.be/xHq_ZNuvQ-E
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Plantation Key
$2,650,000 2,518 (SqFt)
  • 5
  • 4
  • Single Family

163 Indian Mound Trail
ISLAMORADA, FL 33070

Indian Harbor   Waterfront: Yes MM: 89
Side of Island: Bay/Gulf
Dockage: n/a

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.
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Lower Matecumbe
$2,600,000 3,382 (SqFt)
  • 4
  • 4
  • Single Family

77521 Overseas Highway Res-1
ISLAMORADA, FL 33036

Mat Ocean Beach   Waterfront: Yes MM: 75
Side of Island: Ocean
Dockage: None

Tarpon Point, an exclusive enclave of 12 oceanfront residences. Designed to meet the ultra-high standards of the developers, these exceptional homes allow for the most advanced building techniques to reside in harmony with one of the worlds few remaining untouched and fully protected marine habitats. The spacious four-bedroom, four-bath homes range from2,700 to 3,380 square feet of
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Upper Matecumbe Key Islamorada
$2,600,000 1,830 (SqFt)
  • 3
  • 2
  • Single Family

82230 Overseas Highway
ISLAMORADA, FL 33036

Strattons   Waterfront: Yes MM: 83
Side of Island: Bay/Gulf
Dockage: BasinCut/Natural

LOCATION! LOCATION! THIS IS IT! Deep water dockage, and endless views of Florida Bay with 100 ft. of water frontage and over 400 ft. from the road to the water. This family residence has been updated recently with granite gourmets kitchen and a covered porch that expands the width of the back deck for lounging or celebrating days end with another beautiful Islamorada
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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 07-28-2015.

Shoreline Properties
92300 Overseas Hwy Suite 303
Tavernier, Florida 33070

1(800) 692-3605
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