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

Total Listings 11
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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: 413
-11.76% ($2,000,000) 1 Price Change : Last Change 280 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.

209 E Carroll Street  For Sale, MLS 590112
$7,900,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
8 Bed, 8 Baths, 4,931 SqFt Days Listed: 128
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

200  Atlantic Street  For Sale, MLS 589035
$7,900,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
8 Bed, 8 Baths, 4,744 SqFt Days Listed: 184
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.

3  Flamingo Hammock Road  For Sale, MLS 591331
$2,750,000
Upper Matecumbe Key Islamorada
Bay Hammock   - MM: 83.20
4 Bed, 4 Baths, 3,224 SqFt Days Listed: 20
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.

12  Flamingo Hammock Road  For Sale, MLS 589658
$2,275,000
Upper Matecumbe Key Islamorada
Bay Hammock   - MM: 83.20
4 Bed, 4 Baths, 3,270 SqFt Days Listed: 154
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Basin,

ISLAMORADA SUNSETS IN BAY HAMMOCK! Enjoy bay & sunset views all year from all 3 levels of this custom built 4B/4.5B residence in a secluded gated community on Upper Matecumbe Key in the center of Islamorada with dedicated 12 Ft wide boat slip in protected marina directly on Florida Bay. Tri-level concrete home w/masonry siding, impact windows & doors offering an open floor plan, en suite baths, coastal theme, soaring vaulted ceilings, gourmet kitchen, French doors to covered & tiled patios, incredible bay views. 3rd level master suite, ground floor guest quarters, garage, fenced yard, native foliage. Gated community offers boat ramp, observation deck, fish cleaning tables, protected dockage in marina. Unique setting in the Village of Islands that must be seen to be appreciated!

83251  Old Highway  For Sale, MLS 588779
$2,250,000
Upper Matecumbe Key Islamorada
The Russell Estates   - MM: 83.50
4 Bed, 4 Baths, 1,387 SqFt Days Listed: 203
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.

83257  Old Highway  For Sale, MLS 588229
$1,998,000
Upper Matecumbe Key Islamorada
The Russell Estates   - MM: 83.50
5 Bed, 5 Baths, 3,000 SqFt Days Listed: 239
-20.08% ($502,000) 1 Price Change : Last Change 164 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Natural Beach Oceanfront Custom Artist Home - 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 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.

81120  Old High way Highway  For Sale, MLS 591169
$1,200,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
2 Bed, 2 Baths, 772 SqFt Days Listed: 32
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Located in the heart of Islamorada This home is one of the few original 1936 Red Cross houses or affectionately called the Hurricane house. One of 25 that remain today. Constructed with concrete dove-tailed footers deep into the coral bedrock never to move again by any storm. Walls 12 thick of steel reinforced concrete with equally strong concrete floors and roof. This home is meticulously cared for by its loving owners. Nestled on just over 1/2 acre on two lots with beautiful trees and plants. Sit on your porch and with your favorite refreshment and be entertained by the birds enjoying the most magnificent 90 year old Royal Poinciana you ever seen. Plenty of storage for the toys. Cant forget the cast iron claw ft. tub . So much more to this special home. Please : By appointment only

117  Seashore Drive  For Sale, MLS 591512
$889,000
Upper Matecumbe Key Islamorada
Green Turtle Beach   - MM: 81.00
3 Bed, 3 Baths, 2,624 SqFt Days Listed: 8
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Motivated Seller with a new and improved price!The Tamarind House... Youll enjoy this family style residence and the island life in this expansive Florida Keys home. Located in a quiet, serene area of Islamorada, just a few minutes to all the restaurants, galleries, and boutiques you might want to keep you entertained. Home is Built on concrete foundation and cement block walls. Finished with Hardie fiber cement siding and a brand new metal roof that meets todays wind resistant requirements for insurance. Accordion and panel shutters are included. With a double carport and workshop on the ground floor, youll have plenty of parking and storage. The second floor features a spacious, open floor plan kitchen, bar, dining and living room with soaring ceilings!

130  Palermo Drive  For Sale, MLS 589456
$695,000
Upper Matecumbe Key Islamorada
Venetian Shores   - MM: 86.00
2 Bed, 2 Baths, 929 SqFt Days Listed: 164
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 70ft.

Canal front Property in prestigious Venetian Shores! Large 7000 sqft Lot, seawall under 8 yrs old with 70 ft concrete dock and two 50 amp electrical outlets. Located on one of the widest canals in the Upper Keys, this property can accommodate large vessels, with deep water to ease the access to the Bay/Gulf and Atlantic. Listed property for sale is of lot value only. Buyer & Seller agree the vertical improvements are of no value. Close to shopping and schools.

105  Parker Drive  For Sale, MLS 589621
$649,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
3 Bed, 3 Baths, 1,544 SqFt Days Listed: 155
-7.15% ($50,000) 2 Price Changes : Last Change 22 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Prime Location in the Heart of Islamorada! This lovingly updated home offers 3 bedrooms and 3 bathrooms, including an amazing master suite, a gorgeous kitchen with a gas stove and vaulted Dade County pine ceilings. Much larger inside than it appears! Centrally located near the best that Islamorada has to offer in the way of restaurants, shopping, art galleries and more! Large fenced back yard has a 10x12 shed with electricity makes a great work shop.

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 07-09-2020.

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

1(800) 692-3605
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