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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 13
Order By:

$450,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
2 Bed, 2 Baths, 1,095 SqFt Days Listed: 201
-23.60% ($139,000) 2 Price Changes : Last Change 12 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

$595,000
Upper Matecumbe Key Islamorada
Grove Park   - MM: 81.50
3 Bed, 3 Baths, 1,344 SqFt Days Listed: 354
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.

$599,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
3 Bed, 3 Baths, 1,544 SqFt Days Listed: 235
-14.31% ($100,000) 3 Price Changes : Last Change 68 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.

$950,000
Upper Matecumbe Key Islamorada
Green Turtle Beach   - MM: 81.00
4 Bed, 4 Baths, 2,820 SqFt Days Listed: 58
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Excellent location in the heart of Islamorada within walking distance to the best restaurants, boutiques, spas, and art shows. Lushly landscaped, this property has the feel of island living. Open floor plan with the living area, dining/kitchen and guest bedroom opening up to the pool area through french doors. This 4 bedroom 2.5 bath has the master suite upstairs for complete privacy, with the other 3 bedrooms on the main level. Brand new A/C and new metal roof. A spacious 2 car garage with automated door, has plenty of room for all your water toys. Included and within walking distance, theres a private Homeowners Beach - this sits just down the street. An ideal spot to view the sunrise, enjoy an afternoon beverage, ocean breezes or just go for a swim.

$1,200,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
2 Bed, 2 Baths, 772 SqFt Days Listed: 112
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

$1,250,000
Upper Matecumbe Key Islamorada
The Key   - MM: 80.50
4 Bed, 4 Baths, 1,861 SqFt Days Listed: 17
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

~More photos coming soon~Imagine the immense possibilities for this gated, ocean-front estate! The +/-1.75 acre lot is loaded with lush native foliage, bougainvillea, and coconut palms. A trail leads to a small private Atlantic Ocean access and views.The existing structures on this parcel are in need of TLC, but may be a good shell. The main dwelling consists of a 3 bedroom, 3 bath plan and has a separate 1 bedroom, 1 bath guest quarters. New owners can either restore the estate or replace with their own personal dream beach house!

$2,250,000
Upper Matecumbe Key Islamorada
The Russell Estates   - MM: 83.50
4 Bed, 4 Baths, 1,987 SqFt Days Listed: 283
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.

$2,749,000
Upper Matecumbe Key Islamorada
Bay Hammock   - MM: 83.20
4 Bed, 4 Baths, 3,224 SqFt Days Listed: 100
-0.04% ($1,000) 1 Price Change : Last Change 28 Days Ago
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: 47
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.

$5,950,000
Upper Matecumbe Key Islamorada
Caribee Beach   - MM: 80.00
6 Bed, 6 Baths, 2,635 SqFt Days Listed: 35
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift100ft.

CARIBEE BEACH HOUSE is the perfect mix of old school Islamorada charm combined with present-day, stylish luxuries. One of the few oceanfront estates with a deep water basin and its own channel allowing access for larger vessels. 200 of shoreline with a sandy beach and fabulous views of Alligator Lighthouse. The 100 dock features a 24k lb boatlift and the irreplaceable concrete jetty has a boathouse and 4,500 lb lift for your skiff. The main house is 3 bedrooms / 3 bathrooms and is fully renovated. The new guesthouse is 3 bedrooms / 2 bathrooms and has a 3 bay garage on the first floor. Fully fenced-in and gated, a custom putting green, heated and chilled pool, zipline, and biking distance to everything Islamorada has to offer, makes for a perfect package! The property has the space and

$7,900,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
8 Bed, 8 Baths, 4,744 SqFt Days Listed: 264
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: 208
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

$13,500,000
Upper Matecumbe Key Islamorada
Tea Table   - MM: 79.50
5 Bed, 5 Baths, 3,104 SqFt Days Listed: 493
-20.59% ($3,500,000) 4 Price Changes : Last Change 8 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 09-27-2020.

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

1(800) 692-3605
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