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

Total Listings 154
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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: 3
  • 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: 160
  • 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.

$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: 361
  • 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: 336
  • 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.

$6,500,000 - 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: 400
  • 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...

$6,250,000 - 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: 228
  • 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!

$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: 140
  • 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.

$5,400,000 - 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: 1944
  • 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!

$4,500,000 - Islamorada (Plantation Key) , FL

  • Beds: 2 Baths: 1
    Type: Single Family Home - MM: 88
  • MLS ID 566047
    Sq Ft: 3,093
  • Community: Plantation Beach Days on Market: 11
  • Waterfront: Yes - Waterview: Bay Front,Gulf Front,Open Water
  • Side of Island: Bay/Gulf Dockage: Davits

Exquisite Tri Level 4 BR/ 5 BA Beach Estate features unobstructed panoramic Gulf views from almost every room! The Ground floor features foyer, master bedroom room suite, and full bathroom. The second floor consists of 2 bedrooms, 2 Baths, den, great room, laundry, room, and kitchen. Third story there is a second master suite. Open Concept dream kitchen with granite and stainless steel appliances.

$4,500,000 - Islamorada (Windley Key) , FL

  • Beds: 10 Baths: 8
    Type: Single Family Home - MM: 85
  • MLS ID 561920
    Sq Ft: 6,262
  • Community: Windley Key Mobile Home Park Condominiums Days on Market: 486
  • 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.

$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: 98
  • 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.

$4,250,000 - 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: 142
  • 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.

$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: 107
  • 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: 3 Baths: 3
    Type: Single Family Home - MM: 89
  • MLS ID 565763
    Sq Ft: 2,488
  • Community: Trop Coral Reef Days on Market: 41
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage:

Exquisite private beachfront estate surrounded by tall, lush palms with zero entry oasis pool, and dockage! Located on beautiful Plantation Key, an hour from Miami, but a world away!

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

  • Beds: 3 Baths: 3
    Type: Single Family Home - MM: 89
  • MLS ID 564216
    Sq Ft: 2,313
  • Community: Trop Coral Reef Days on Market: 230
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage:

The Gardens is located on 1.53 acresof mature tropical foliage, with expansive sandy beach, long dock, decorative columns, gated entry and winding Chicago Brick drive. Upstairs, this exquisite home features two bedrooms, two baths, two large glass front porches, kitchen with bar, dining and living room. Double glass doors and windows provide breathtaking ocean views. A wrap around porch

$3,300,000 - Islamorada (Plantation Key) , FL

  • Beds: 4 Baths: 3
    Type: Single Family Home - MM: 89
  • MLS ID 558232
    Sq Ft: 5,023
  • Community: Key Heights Days on Market: 922
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Boat Lift,Davit Pads,Davits,Other Dockage 400ft. Concrete

OCEANFRONT ESTATE on MILLIONAIRES ROW..Plantation Key..Islamoradas premier address. Privately gated 4bd/3ba concrete home offers deep water Boat Dockage,400ft.Pier, 2 boat lifts & davits.The sparkling in-ground pool& Open OCEAN VIEWS makes this elegant custom home great for entertaining with soaring central atrium ceiling surrounding by walls of sunlit windows.Wet bar, high end kitchen & mo

$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: 318
  • 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.

$2,850,000 - Islamorada (Lower Matecumbe) , FL

  • Beds: 4 Baths: 4
    Type: Single Family Home - MM: 75
  • MLS ID 563863
    Sq Ft: 5,126
  • Community: Port Antigua Days on Market: 273
  • Waterfront: Yes - Waterview: Canal Front
  • Side of Island: Bay/Gulf Dockage: Boat Lift,Davits 161ft.

Waterfront Perfection!Custom-built 4 bedroom, 4.5 bath concrete home in a desirable bayside community. Under an elegant archway, tropically-themed iron and glass doors invite you in to a large foyer. Ascend the decorative stairway or take the elevator to living levels. On 2nd level you will find a great room with wet bar containing SUB-ZERO refrigerated drawers and a SUB-ZERO ice maker...

$2,795,000 - Islamorada (Lower Matecumbe) , FL

  • Beds: 3 Baths: 3
    Type: Single Family Home - MM: 74
  • MLS ID 566002
    Sq Ft: 4,004
  • Community: Lower Mat Beach Days on Market: 17
  • Waterfront: Yes - Waterview: Canal Front,Oceanfront
  • Side of Island: Ocean Dockage: 42ft.

OCEAN VIEW GATED ESTATE WITH BEACH & DOCKAGE! This beautiful ocean view home is situated on a point lot with over a half an acre of land offering over 4,000 square feet of living space, 3 bdrms & 3 bthrms w/2 ocean front master stes, open floor plan w/soaring ceilings, oceanfront porch,6 car garage, lush tropical landscaping surrounding a flowing pond, deep water dockage, elevator & so much more!

$2,750,000 - Islamorada (Plantation Key) , FL

  • Beds: 4 Baths: 3
    Type: Single Family Home - MM: 87
  • MLS ID 565985
    Sq Ft: 3,692
  • Community: Plantation Lake Estates Days on Market: 18
  • Waterfront: Yes - Waterview: Oceanfront
  • Side of Island: Ocean Dockage: Davits 38ft.

ELEGANT OCEANFRONT ESTATE LOCATED IN GATED PRIVATE SURROUNDINGS OVERLOOKING THE ATLANTIC OCEAN. BUILT IN 2004, THIS CUSTOM RESIDENCE OFFERS FOUR BEDROOMS, EXPANSIVE MASTER SUITE, PRIVATE GUEST SUITE, AND IMPRESSIVE GREAT ROOM ENCOMPASSING A CHEFS KITCHEN, DINING, AND LIVING AREA. ENCOMPASSED BY THE OCEAN ON ONE SIDE AND PROTECTED HARBOR ON THE OTHER FOR DOCKAGE, THIS IS A RARE FIND.

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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 12-21-2014.