Upper Matecumbe Key Islamorada Homes for Sale, Single Family Houses, MLS Home Listings

Homes for sale in Upper Matecumbe are highly in demand, greater still as a part of the larger area known as Islamorada.  Islamorada is known for its superior off-shore fishing, large assortment of restaurants, and great areas for shopping - and Florida Keys real estate buyers looking at Upper Matecumbe houses have access to all this and more.  Upper Matecumbe Key properties are often located waterfront, and are typically characterized by a unique Florida Keys charm.  See all MLS listings of houses for sale in Upper Matecumbe Key Islamorada below.

Total Listings 14
Order By:

82192  Old Highway  For Sale, MLS 589564
$249,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 1,082 SqFt Days Listed: 66
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Mixed-use Village Center (VC) Zoned property Located in the heart of Islamorada! This desirable mixed use property offers 100ft of frontage on the Old Hwy. Village recognizes one dwelling unit so a BPAS application is NOT required to rebuild. Existing structure hasIRMA damage and is being sold for the land value only. Seller is willing to pay for the demo! Great opportunity for so many different possible uses!

117 S Hammock Road  For Sale, MLS 590243
$520,000
Upper Matecumbe Key Islamorada
Hammock   - MM: 83.50
3 Bed, 3 Baths, 2,712 SqFt Days Listed: 28
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

VIRTUAL SHOWINGS AVAILABLE via FACETIME or VIDEO! Bring your creative vision to this one of a kind central Islamorada opportunity! This unique CBS home awaits your imagination and creative touches. Offering a very spacious 2700 plus square feet of living space and situated on two and one-half tropical lots with circular drive as well as plenty of off street parking for multiple vehicles including room for your RV. Envision entering the Keystone foyer, stepping up into the formal living area as you pass by the atrium that would make a lovely orchid or garden with water feature, and gazing through the French doors onto grounds with so much potential and room for a large pool and outdoor entertaining area.

100  Parker Drive  For Sale, MLS 590235
$589,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
2 Bed, 2 Baths, 1,095 SqFt Days Listed: 29
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

201  Jerome Avenue  For Sale, MLS 587676
$595,000
Upper Matecumbe Key Islamorada
Grove Park   - MM: 81.50
3 Bed, 3 Baths, 1,344 SqFt Days Listed: 182
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

nice ground level home on a quiet and shady lot in the heart of Islamorada, X flood zone, great neighborhood, walking distance to great restaurants and shopping, close to fishing and diving charters, double car garage gives plenty of storage, screened entertainment & relaxation area provides nice outdoor sitting space, tile throughout, fresh paint inside & outside, vaulted ceilings, indoor toilets, breakfast bar, washer & dryer in garage, low maintenance grounds.

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: 72
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
$699,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
3 Bed, 3 Baths, 1,544 SqFt Days Listed: 63
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.

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: 147
-20.08% ($502,000) 1 Price Change : Last Change 71 Days Ago
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 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.

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: 111
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.

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: 62
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!

82994  Overseas Highway 23 For Sale, MLS 579971
$2,499,000
Upper Matecumbe Key Islamorada
Penn Key Club   - MM: 83.00
3 Bed, 3 Baths, 1,812 SqFt Days Listed: 709
-28.60% ($1,001,000) 5 Price Changes : Last Change 89 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!

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: 128
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.

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: 92
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.

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: 36
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

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: 321
-11.76% ($2,000,000) 1 Price Change : Last Change 187 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 04-08-2020.

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

1(800) 692-3605
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