Upper Matecumbe Key Islamorada Waterfront Homes for Sale, Single Family Houses, Open Water, Ocean and Bay / Gulf Views

Waterfront properties in Upper Matecumbe Key are spectacular pieces of real estate for buyers looking for permanent residences or vacation homes.  Residents are able to take advantage of incredible off-shore water sports, great restaurants, and top Florida Keys attractions.  If you are looking for homes with boat dockage or deep water access, Upper Matecumbe Key oceanfront homes or Upper Matecumbe bayfront houses are great choices with some of the best views available in the Florida Keys.  Browse the MLS listings of waterfront real estate in Upper Matecumbe below.

Total Listings 8
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82762  Overseas Highway 4 For Sale, MLS 588011
$925,000
Upper Matecumbe Key Islamorada
Madeira Bay   - MM: 82.50
3 Bed, 3 Baths, 1,956 SqFt Days Listed: 43
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Boat Slip,

WATERFRONT GATED ENCLAVE IN ISLAMORADA! Enjoy partial bayviews and your own dedicated boat slip directly on Florida Bay. This tri-level 3B/2B home is located just one home off Florida Bay on Upper Matecumbe Key in Madeira Bay, a gated community of only 8 single family residences with shared pool & dock. Open floor plan with vaulted ceilings, tiled floors, multiple sliding glass doors to decks on both living levels. Ground level enclosure is above base flood and permitted living area w/plumbing for bathroom. Truly a must see property to appreciate this unique setting with a Bayview & Dockage!

81906  Overseas Highway  5 For Sale, MLS 580100
$1,150,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 1,852 SqFt Days Listed: 585
+4.55% ($50,000) 1 Price Change : Last Change 193 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

NEW CONSTRUCTION. CORAL COVE an intimate gated community of 9 site-built homes in the heart of downtown Islamorada. Bayfront with boat basin and dock, each home has its own private pool, state of the art amenities and details plus light and bright natural stone and wood finishes and just steps away from all that Islamorada has to offer.Developers are FL licensed real estate agents.

83257  Old Highway  For Sale, MLS 588229
$2,500,000
Upper Matecumbe Key Islamorada
The Russell Estates   - MM: 83.50
5 Bed, 5 Baths, 3,000 SqFt Days Listed: 30
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Natural Beach Oceanfront Estate - enjoy the barefoot elegance of this custom Poured Concrete GREEN island home. Featured in Fine Home Building & Natural Home magazines, historic Red Cross home lovingly remodeled plus 2 thoughtful, Eco friendly architect designed & built additions add modern, artistic feel. Custom Everything! Enjoy living on the best island, separate living spaces, high arched ceilings, private outdoor shower, spacious beachfront pottery studio & or huge drivethrough 3 car garage, fabulous views, orchard, solar panels, cistern, and so much more! If you long for brilliant design where indoor and outdoor living are seamlessly integrated, you will love this home. Please call to schedule your private tour- experience artistic excellence, unity with nature, & sheer bliss.

82994  Overseas Highway 23 For Sale, MLS 579971
$2,799,000
Upper Matecumbe Key Islamorada
Penn Key Club   - MM: 83.00
3 Bed, 3 Baths, 1,812 SqFt Days Listed: 592
-20.03% ($701,000) 4 Price Changes : Last Change 81 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Dock P

A classic Islamorada retreat. This private home is located in the exclusive bayfront gated community of Pen Key Club in the heart of Islamorada. The lovely one-story home offers three bedrooms and three bathrooms with panoramic views of the open water from every angle. Enjoy magnificent sunsets while relaxing in the living room or charming sitting areas on the open bay. In addition, the Pen Key Club offers a pool and boat dockage in a protected boat basin. This offering is Florida Keys living at its finest!

80531  Old Highway  For Sale, MLS 584600
$3,650,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
3 Bed, 3 Baths, 2,044 SqFt Days Listed: 285
-5.66% ($219,000) 1 Price Change : Last Change 222 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None,Other DockageCo

A one-of-a-kind 4.33-acre estate on Upper Matecumbe Key. Enter the gate and follow the classic brick driveway to one of Islamoradas most private settings. The main house, which is above the flood zone, offers two bedrooms and two-and-a-half bathrooms, featuring high beamed ceilings, tile floors, and ocean views. A guest cottage offers one bedroom, one bathroom, and a large sitting room. Watch the colors of beautiful sunrises and incredible sunsets reflect off Alligator Lighthouse from all rooms. Look for tailing bonefish and wading birds, or just sit by the pool and relax--Mother Nature is your living room. A caretakers cottage as well as a guest cottage can be added to the property as of right. Two additional lots have the possibility to be rezoned.

80639  Old Highway 101 For Sale, MLS 587835
$3,995,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
4 Bed, 4 Baths, 2,997 SqFt Days Listed: 54
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Welcome to Maison Residences, your private oceanfront retreat in Islamorada. Enjoy open ocean views as soon as you step inside the front door! The view widens as you walk through the kitchen and dining area to the living area and the open lanai. This same view can be enjoyed from the luxurious master bedroom and balcony. Nature lovers can watch the wading birds feeding in the shallows, the pelicans diving for breakfast and porpoises playing without leaving your porch. Views of the lawn, palm trees, beach, dock and ocean will fill our mind and entice you to come back often. This smart home was finished with great attention to detail and features 10 ft. ceilings, 9 ft. doors, 2 AC units with 3 zones, Wolf and SubZero appliances, privately keyed elevator, 86 ft. resort style pool,

80221  Overseas Highway  For Sale, MLS 588502
$5,700,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 81.20
4 Bed, 4 Baths, 3,195 SqFt Days Listed: 11
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

COCOMOS is a picturesque, and tropical, island retreat, on a beautiful 3-acre ocean-front estate, just a short walk away from the art district in Islamorada. This property is secluded with a private, electronically gated entry. Outdoor amenities include 250 of pristine sandy beach, pool with waterfall and ocean-front pool deck, outdoor shower, huge furnished Chickee with full summer kitchen, new dock, pond, great lawn and lush landscaping. The main house hosts 3 bedrooms and 3 baths with two living rooms and two kitchens. The guest house hosts 2 queen beds, a sleeper sofa, kitchen, bath and 2 ocean-front patios.

79775  Overseas Highway  For Sale, MLS 585835
$15,000,000
Upper Matecumbe Key Islamorada
Tea Table   - MM: 79.50
5 Bed, 5 Baths, 3,104 SqFt Days Listed: 204
-11.76% ($2,000,000) 1 Price Change : Last Change 72 Days Ago
Off Shore Isl - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits40ft.

An extremely rare and stunning private island, accessible by car, Terras Key is a gated Caribbean Island located at Mile Marker 79.7 in Islamorada. Jutting into the blue-green waters of the Atlantic Ocean, Terras Key features a 2,000+- driveway enabling you to reach restaurants and shopping easily.Enjoy the conveniences of the modern world, including all utilities, while surrounded with the privacy of your own +15.5 Acre Island with miles of open water views and views of Alligator Reef Light. The compound includes 5 bedrooms and 4 baths, pool, cabana, dockage, and a tennis court. This extraordinary private island is a landmark in Islamorada and the Florida Keys and has not been offered for sale for over 27 years.

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 12-13-2019.

Broker's Edge Realty
92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
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