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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 6
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$2,250,000
Upper Matecumbe Key Islamorada
The Russell Estates   - MM: 83.50
4 Bed, 4 Baths, 1,387 SqFt Days Listed: 239
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Experience Florida Keys charm in this Seaside cottage retreat in the heart of Islamorada. Offering an island-style main house with 2 bedrooms and 2 baths, wrapped by a gracious lanai leading to your private pristine beach and sparkling Atlantic Ocean. Guest quarters with 2 bedrooms/1bath atop a 2 car garage offer space for visitors and all your cars and toys. Gated private setting, this extensively remodeled beachfront estate on 3/4 acres is conveniently located near shopping, dining and world class fishing and diving.

$2,750,000
Upper Matecumbe Key Islamorada
Bay Hammock   - MM: 83.20
4 Bed, 4 Baths, 3,224 SqFt Days Listed: 56
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Boat R

On rare occasions a truly special home comes to market. One built with inspiration and imagination created to compliment & accentuate the land on which it was constructed. That opportunity has arrived. Located within an exclusive gated community, this brand new home offers 3224 ft of gorgeous design space with top of the line finishes and features for even the most discriminating buyer. Whether enjoying your boat slip at your private marina, your two expansive balconies overlooking the conservation area, the gorgeous pool or spectacular sunsets from the rooftop deck that overlooks the bay and offers 360 degree views of the island with an outdoor kitchen and jacuzzi, you will be swept away by the tranquil and luxurious Keys life this home offers you. Truly a once in a lifetime opportunity.

$2,994,000
Upper Matecumbe Key Islamorada
Bay Hammock   - MM: 83.20
4 Bed, 4 Baths, 3,474 SqFt Days Listed: 3
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Basin,

Bay Hammocks is a unique, secluded Hidden Paradise with 33 home sites in a gated boat access community. THE GREAT ESCAPE. Enjoy a modern Brand-New Coastal Design Home completed in 2020. This luxurious 4-bedrooms, 4 & 1/2 baths new 2-story residence invites you to feel like you are on vacation every day. The textures and materials were carefully chosen and no expense was spared. Attention to detail abounds when you enter this home. The main floor leads to the inviting, spacious living space with a large bar area (along with a built-in wine rack with all the frills) and one bedroom with luxurious bath makes this an ideal retreat for overnight guests. Beyond the living room are screened-in entertaining lanai area, Jacuzzi and pool.

$7,900,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
8 Bed, 8 Baths, 4,744 SqFt Days Listed: 220
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Introducing Bunny Key, an extraordinary historic Islamorada oceanfront plantation. Once you enter the gate you will be entranced by the prettiest beach on the island of Islamorada with an estimated 240 feet lining the Atlantic ocean and lovely new dock. The main home and guest wing of 3 bedrooms radiate character at every corner, reminiscent of a time gone by with the inviting Old Florida porch stepping out on to the beach. The Kitchen is lined in custom Pecky Cypress cabinets and stone counters which blends beautifully with the Dade County pine flooring throughout. There is a historic 3 bedroom guest home and a 2 bedroom caretakers cottage on the sprawling grounds each with beautiful verandas featuring ocean vistas. Detached garage and outdoor kitchen area can also be found.

$7,900,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
8 Bed, 8 Baths, 4,931 SqFt Days Listed: 164
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

FairWinds~A unique two acre oceanfront estate, discretely situated in downtown Islamorada on Upper Matecumbe Key. FairWinds reflects elegance, beauty, seclusion, along with many amenities. Inside the gates are enchantingly lush tropical gardens with carefully cultivated native specimens leading to the shimmering pastel blues of the Atlantic ocean, which gently caresses the 250+ feet of secluded sandy beach. This very special compound blends privacy with abundant recreational opportunities, ideally suited to create cherished memories with family and friends. FairWinds offers a grand main house, complete with a wrap-around porch, wide verandas and stunning ocean views, perfect for memorable gatherings of family and friends. Watch the sun rise beyond the historic Alligator Reef Lighthouse

$14,500,000
Upper Matecumbe Key Islamorada
Tea Table   - MM: 79.50
5 Bed, 5 Baths, 3,104 SqFt Days Listed: 449
-14.71% ($2,500,000) 2 Price Changes : Last Change 3 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 08-14-2020.

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

1(800) 692-3605
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