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

Total Listings 130
82910  Overseas Highway
$14,500,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
13 Bed, 13 Baths, 6,519 SqFt
Single Family - Active - Waterfront Yes
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...

89251  Old Highway
$7,950,000
Plantation Key
Trop Coral Reef   - MM: 89.00
3 Bed, 3 Baths, 1,243 SqFt
Single Family - Active - Waterfront Yes
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.

82500  Old State Road
$7,500,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
4 Bed, 4 Baths, 3,443 SqFt
Single Family - Active - Waterfront Yes
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.

88835  Old Highway
$6,498,000
Plantation Key
Pearl City   - MM: 89.00
5 Bed, 5 Baths, 3,640 SqFt
Multi-Units - Active - Waterfront Yes
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...

87961  Old Highway
$6,000,000
Plantation Key
Plantation Beach   - MM: 88.00
6 Bed, 6 Baths, 7,855 SqFt
Single Family - Active - Waterfront Yes
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 . Please contract Danny Sanchez @ (305) 896-7253

85261  Old Highway
$5,400,000
Windley Key
Unplatted Windley Key   - MM: 88.00
3 Bed, 3 Baths, 1,839 SqFt
Single Family - Active - Waterfront Yes
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!

101  CARROLL Street
$4,950,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
2 Bed, 2 Baths, 959 SqFt
Single Family - Active - Waterfront Yes
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!

210  Plantation Boulevard
$4,900,000
Plantation Key
Plantation Beach   - MM: 87.50
5 Bed, 5 Baths, 4,512 SqFt
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Boat Lift

Newly Constructed Gated Bay Front Estate in Islamorada featuring amazing sunsets, 5 bdrms, 3 bths, 2 powder rms, gourmet kitchen over 4,500 sf of living space, expansive porches, elevator, outdoor kitchen, & dining make this luxury living at its finest. Beautiful bay front pool & spa, 100 ft. dock w/boat lift, cut in basin w/direct bay & easy ocean access. Truly an Island Lifestyle Experience!

89051  Old Highway
$4,700,000
Plantation Key
Misc Plantation Key   - MM: 85.00
4 Bed, 4 Baths, 4,573 SqFt
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift300ft.Concr

CASA EROICI ESTATE ON MILLIONAIRES ROW! Meander through the gate down the winding drive to this 4 bedroom, 4.5 bath, spectacular oceanfront home, offering fine interior amenities, soaring ceilings, gourmet kitchen, 3rd floor master ste w/a luxurious bath, 3 additional en-suites w/private patios, gorgeous ocean views, heated spa & pool,rare private sandy beach, elevator and more! truly a treasure!

89401  Old Highway
$4,600,000
Plantation Key
Misc Plantation Key   - MM: 89.40
5 Bed, 5 Baths, 4,622 SqFt
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin,Boat Lift

Oceanfront estate on desired Old Highway. Great ocean views, and gracious, island-style home currently has 5 bedrooms & 5.5 baths. Sandy beach and Beautiful double slide pool with waterfall and spacious outdoor entertaining area. Gated entry, paver driveway. Construction has just started on the addition of a new master suite, guest room. Price is for current phase of construction.

88547  Old Highway
$4,000,000
Plantation Key
Key Heights   - MM: 88.50
4 Bed, 4 Baths, 3,438 SqFt
Single Family - Active - Waterfront Yes
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!

150  Redwing Road
$3,999,999
Plantation Key
Sunshine Estates   - MM: 90.00
4 Bed, 4 Baths, 5,311 SqFt
Single Family - Active - Waterfront Yes
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.

75931  Overseas Highway
$3,899,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
5 Bed, 5 Baths, 4,770 SqFt
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Luxury and tranquility await you at this prestigious oceanfront estate on Lower Matecumbe in Islamorada. Relax on the +150 ft of sandy beach or watch incredible Keys sunrises from the second floor master suite porch. The stunning chefs kitchen offers 3 ovens, warming drawer, ice maker and wine cooler. Separate quest quarters provides 1 bedroom, 1 bath, kitchenette and private deck. A Must See!

161  Indian Mound Trail
$3,800,000
Plantation Key
Indian Harbor   - MM: 89.00
5 Bed, 5 Baths, 4,152 SqFt
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift70ft.Concre

Magnificent direct bay front home with deepwater dockage, swimming pool & spa. Professionally landscaped and offers maintenance free artificial grass. This stunning home has cathedral ceilings, large living area great for entertaining, magnificent open water views and a separate downstairs guest quarters that is conforming. This is an all concrete home with a concrete roof that has been

84775  Old Highway
$3,750,000
Windley Key
Unplatted Windley Key   - MM: 85.00
10 Bed, 10 Baths, 6,262 SqFt
Single Family - Active - Waterfront Yes
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.

137  Sapodilla Drive
$3,200,000
Lower Matecumbe
Mat Sandy Beach   - MM: 75.00
5 Bed, 5 Baths, 5,456 SqFt
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Davits

Stunning Home with protected dockage on a tranquil lagoon easy access to Bay and Ocean. Custom-designed 5 bedroom, 5 bath home constructed to withstand 155 mph winds...featuring over 100 feet of waterfront, concrete dock, 2 boat lifts, custom pool and spaMarble floors, gorgeous kitchen with granite countertops, top quality appliancesThis superior home has been meticulously planned and

89701  Old Highway
$3,200,000
Plantation Key
Misc Plantation Key   - MM: 85.00
4 Bed, 4 Baths, 1,735 SqFt
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

San Roc Estate is one of the last remaining parcels on the Atlantic offering a 4 bedroom 3 bath seaside retreat nestled on over 2 Acres of Land w/sandy beach. Exterior amenities include a keystone lanai for ultimate in/outdoor living, ample deep channel dockage, Lap pool,heated spa surrounded by coconut palms offering ultimate privacy,truly invokes a sense of laid back lifestyle we all dream of!

121  Columbus Drive
$3,190,000
Lower Matecumbe
Mat Ocean View   - MM: 76.50
6 Bed, 6 Baths, 3,900 SqFt
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Boat Ramp,

OCEAN FRONT ESTATEMagnificent panoramic views of open Atlantic from most rooms and pool, with total privacy. Enormous master suite and bath, huge his and hers walk-in closet with complete built-in storage. This home is ready for entertaining, 6 bedrooms and five baths, office, plus 3rd story bonus room. Newly up-dated kitchen. Including a sea walled boat dock on deep-water canal.

130  Aregood Lane
$2,995,000
Plantation Key
Pearl City   - MM: 89.00
4 Bed, 4 Baths, 3,092 SqFt
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Stroll 210 ft of private beach & shoreline or sip tea on the veranda while welcoming the sun over the Atlantic Ocean. The entrance to this Victorian estate home is a winding drive with a majestic tree canopy. The property offers an oceanview swimming pool, an expansive grassy yard. A charming brick path leads to a pier dock w boat lift.

82762  Overseas Highway 1
$2,900,000
Upper Matecumbe Key Islamorada
Madeira Bay   - MM: 82.50
4 Bed, 4 Baths, 3,291 SqFt
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Boat R

SUNNY DAYS BY THE BAY! Enjoy watching the sunsets over Florida Bay everyday of the year from this Islamorada Bayfront home in gated enclave of Madeira Bay. Tri-level, custom built, concrete, 4B/3.5B offering private Master Suite & guest quarters, French & sliding glass doors to covered patios, large sundeck, 2 car garage, Chicago brick driveway. Plus Boat slip & common pool for all 8 residences.

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 02-12-2016.

Shoreline Properties
92300 Overseas Hwy Suite 303
Tavernier, Florida 33070

1(800) 692-3605
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