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

Total Listings 129
82910  Overseas Highway  For Sale, MLS 567181
$14,500,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
13 Bed, 13 Baths, 6,519 SqFt Days Listed: 390
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  For Sale, MLS 566146
$7,950,000
Plantation Key
Trop Coral Reef   - MM: 89.00
3 Bed, 3 Baths, 1,243 SqFt Days Listed: 499
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  For Sale, MLS 566504
$7,500,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
4 Bed, 4 Baths, 3,443 SqFt Days Listed: 463
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  For Sale, MLS 562582
$6,497,000
Plantation Key
Pearl City   - MM: 89.00
5 Bed, 5 Baths, 3,640 SqFt Days Listed: 899
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  For Sale, MLS 120169
$6,000,000
Plantation Key
Plantation Beach   - MM: 88.00
6 Bed, 6 Baths, 5,791 SqFt Days Listed: 639
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 .

85261  Old Highway  For Sale, MLS 549574
$5,400,000
Windley Key
Unplatted Windley Key   - MM: 88.00
3 Bed, 3 Baths, 1,839 SqFt Days Listed: 2443
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!

210  Plantation Boulevard  For Sale, MLS 568088
$4,900,000
Plantation Key
Plantation Beach   - MM: 87.50
5 Bed, 5 Baths, 4,512 SqFt Days Listed: 279
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  For Sale, MLS 569116
$4,350,000
Plantation Key
Trop Coral Reef   - MM: 89.00
4 Bed, 4 Baths, 4,573 SqFt Days Listed: 154
-7.45% ($350,000) 1 Price Change : Last Change 1 Day Ago
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!

101  CARROLL Street  For Sale, MLS 564240
$4,250,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
2 Bed, 2 Baths, 959 SqFt Days Listed: 727
-14.14% ($700,000) 1 Price Change : Last Change 25 Days Ago
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!

75931  Overseas Highway  For Sale, MLS 569619
$3,899,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
5 Bed, 5 Baths, 4,770 SqFt Days Listed: 104
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!

84775  Old Highway  For Sale, MLS 561920
$3,750,000
Windley Key
Unplatted Windley Key   - MM: 85.00
10 Bed, 10 Baths, 6,262 SqFt Days Listed: 985
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.

88547  Old Highway  For Sale, MLS 567668
$3,500,000
Plantation Key
Key Heights   - MM: 88.50
4 Bed, 4 Baths, 3,438 SqFt Days Listed: 335
-6.67% ($250,000) 1 Price Change : Last Change 22 Days Ago
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!

424 S Coconut Palm Boulevard  For Sale, MLS 570250
$3,490,000
Plantation Key
Plantation Key Colony   - MM: 90.00
4 Bed, 4 Baths, 3,573 SqFt Days Listed: 57
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Boat Lift50ft.

Fabulous Bay Front Home. This home has it all ! Custom built w/ great attention to details. Open living concept w/ Great Room including living room, kitchen and dining area all opening up to a captivating screen porch over looking the Bay w/ spectacular views. Gorgeous sunsets! Top quality throughout. 4 bedrooms, 41/2 baths plus workout / office bonus room. Marble and wood floors. 3 stop elevator

75615  Overseas Highway  For Sale, MLS 570302
$2,995,000
Lower Matecumbe
Mat Ocean Beach   - MM: 75.00
3 Bed, 3 Baths, 3,063 SqFt Days Listed: 52
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

WOW, WOW, WOW. There is not another home like this in Islamorada. Contemporary modern 3063 sq ft home uniquely designed by well known Miami architect Reinaldo Borges who designed the home to mirror the curved shoreline of the beach for ocean view panorama from all rooms through the large hurricane impact floor to ceiling windows - no artwork needed as the ocean,

89701  Old Highway  For Sale, MLS 569117
$2,995,000
Plantation Key
Trop Coral Reef   - MM: 89.00
4 Bed, 4 Baths, 1,735 SqFt Days Listed: 154
-6.41% ($205,000) 1 Price Change : Last Change 1 Day Ago
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!

137  Sapodilla Drive  For Sale, MLS 568375
$2,995,000
Lower Matecumbe
Mat Sandy Beach   - MM: 75.00
5 Bed, 5 Baths, 5,456 SqFt Days Listed: 245
-6.41% ($205,000) 1 Price Change : Last Change 7 Days Ago
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

82703  OLD Highway  For Sale, MLS 563665
$2,995,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 1,825 SqFt Days Listed: 791
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

This unique large parcel in the heart of Islamorada is an outstanding oceanfront property. The original buildings have been lovingly refreshed creating an exquisite beachfront retreat! Price includes plans for additions. Plans for observation dock and swim platform have been drawn.Very popular as a vacation rental, appointments for showings are required.

228  Coral Road  For Sale, MLS 569770
$2,900,000
Plantation Key
Coral Shores   - MM: 86.50
1 Bed, 1 Baths, 608 SqFt Days Listed: 98
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

WATERFRONT ON THE OCEAN. This residential lot offers a 1 bedroom 1 bath home with spectacular ocean views. Ideal for development of your ultimate Keys getaway. This parcel includes the sale of adjoining waterfront vacant lot Alt Key # 9087972 ) Combined acreage of both parcels is approximately 1.87 acres at the end of a cul-de-sac.

157  Bayview Drive  For Sale, MLS 568563
$2,750,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
5 Bed, 5 Baths, 4,200 SqFt Days Listed: 220
-5.01% ($145,000) 1 Price Change : Last Change 6 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift100ft.

Nearing Completion! Brand new construction projected completion date early 2016 for this 6 bedroom 5.1 bath built home by highly respected custom builder. Vaulted ceilings, 3 stop elevator, tremendous living spaces, roof top observation deck, huge balconies & outdoor living areas, plans for large pool, dockage with lift already installed. Colors, cabinets, flooring and baths are being chosen now!

906  Venetian Boulevard  For Sale, MLS 568464
$2,700,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 3,366 SqFt Days Listed: 232
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 100ft.

Beautiful home in highly-coveted Venetian Shores. 100 Ft Deep water dockage. Amazing bay views. Enjoy both the bay and ocean side via snake creek. Great layout. Perfect for a large family. Lap pool, stainless steel appliances. All Third floor bedrooms have magnificent bay views

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 05-03-2016.

Shoreline Properties
92300 Overseas Hwy Suite 303
Tavernier, Florida 33070

1(800) 692-3605
Contact Us