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Upper Matecumbe Key Islamorada Waterfront Homes, Condos, and Properties for Sale, Florida Keys Real Estate

Total Listings 25
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$13,500,000
Upper Matecumbe Key Islamorada
Tea Table   - MM: 79.50
5 Bed, 5 Baths, 3,104 SqFt Days Listed: 494
-20.59% ($3,500,000) 4 Price Changes : Last Change 9 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.

$7,900,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
8 Bed, 8 Baths, 4,744 SqFt Days Listed: 265
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: 209
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

$5,950,000
Upper Matecumbe Key Islamorada
Caribee Beach   - MM: 80.00
6 Bed, 6 Baths, 2,635 SqFt Days Listed: 36
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

$2,995,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
3 Bed, 3 Baths, 3,274 SqFt Days Listed: 329
-7.85% ($255,000) 2 Price Changes : Last Change 265 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage155ft.

Nestled in tranquil bay overlooking Alligator Reef, in the heart of Islamorada, Maison Residences offers the only 4-bedroom condominiums in Islamorada. A rare opportunity to own in a luxurious community featuring its own private white sandy beach and a 155 Day Dock. At only a 90 minute drive from Miami, this remarkable paradise offers the perfect playscape for swimming, boating, fishing and more. Resort style pool and spa can be viewed from the oversized living terrace. Just a short distance from the islands finest restaurant, parks and marinas, this quiet, private and gated community brings a new standard of living to The Florida Keys. Pre-construction in final phase with expected date of delivery end of 2020. ADA Compliant, Smart home, 10 Ceilings and more.

$2,994,000
Upper Matecumbe Key Islamorada
Bay Hammock   - MM: 83.20
4 Bed, 4 Baths, 3,474 SqFt Days Listed: 48
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.

$2,749,000
Upper Matecumbe Key Islamorada
Bay Hammock   - MM: 83.20
4 Bed, 4 Baths, 3,224 SqFt Days Listed: 101
-0.04% ($1,000) 1 Price Change : Last Change 29 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.

$2,250,000
Upper Matecumbe Key Islamorada
The Russell Estates   - MM: 83.50
4 Bed, 4 Baths, 1,987 SqFt Days Listed: 284
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.

$1,859,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
3 Bed, 3 Baths, 2,275 SqFt Days Listed: 55
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Maison Matecumbe, Heart of the Village location in Islamorada on the ocean, an exclusive, gated enclave. This direct oceanfront townhouse affords panoramic views of the Atlantic Ocean from every room! Completely renovated, three bedroom, three bath, light-filled end unit with impact glass windows and doors; open kitchen featuring Italian cabinetry, quartz countertops & top-of-the-line Bosch appliances; sleek, modern baths and beachy wood-look tile floors throughout. From your ample covered parking spaces, an elevator whisks you to an open veranda, and your welcoming front door. Outside youll find a private, sprawling white sand beach, with 155 ft. pier, a fabulously large swimming pool, beachside chickee hut with outdoor grills, all in an intimate development, in this one of 9

$1,250,000
Upper Matecumbe Key Islamorada
The Key   - MM: 80.50
4 Bed, 4 Baths, 1,861 SqFt Days Listed: 18
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!

$1,185,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
3 Bed, 3 Baths, 1,946 SqFt Days Listed: 797
-15.05% ($210,000) 2 Price Changes : Last Change 369 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Exclusive gated oceanfront condo in the heart of Islamorada. This one-story residence offers three bedrooms and two bathrooms, and is in turnkey condition. The property also has covered parking and an excellent rental history. Amenities include a sandy beach, a beautiful new pool, and a convenient location near shops, dining, the Arts District, and marinas that will book fishing and diving excursions.

$1,125,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
3 Bed, 3 Baths, 2,251 SqFt Days Listed: 113
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

In the heart of Islamorada, this beachfront townhouse style three bedroom, three bath condo enjoys open ocean views, sandy beach, beautiful pool, privacy gate and covered parking. Only 9 units in the original building with 12 more underway for an intimate setting with only 21 units total. Elevator from covered parking to the welcoming breezeway entrance at your front door.Nearby amenities include Art District, breweries, restaurants, shopping, resorts and spas and free shuttle around the island

$979,900
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
3 Bed, 3 Baths, 1,484 SqFt Days Listed: 297
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Breathtaking Ocean views from this 3 bedroom 2 bath unit that is centrally located in Islamorada at The Palms of Islamorada. You have floor to ceiling windows that provide spectacular ocean views from the Livingroom, Kitchen, master bedroom and guest bedroom with panoramic ocean views from the large private open terrace. All 3 bedrooms have walk-in closets and closets throughout the condo for plenty of storage space. Kitchen has wood cabinets, granite countertops with stainless steel appliances and 2 ovens that come in handy when entertaining. Some of the many features of the gated complex are covered parking, ocean front pool and spa, tiki hut, gym, clubhouse with kitchen and a kayak launch with storage rack. Steps away from Bud and Marys for all of your boating needs.

$975,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
3 Bed, 3 Baths, 1,484 SqFt Days Listed: 950
-30.11% ($420,000) 3 Price Changes : Last Change 213 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Beautifully renovated 3 bedroom condominium in the Palms of Islamorada. Top floor end unit in southerly building with open ocean views. Walk to fine dining, great fishing boats, both offshore & back country, and a great diving/snorkeling operation. Large private balcony with view of Alligator Light. Unit has been converted to 2 bedroom but will be returned to 3 bedroom if Buyer desires.

$920,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
4 Bed, 4 Baths, 1,232 SqFt Days Listed: 81
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip

Unique Investment Property-WEEKLY RENTALS & BOAT DOCKAGE. Own a free standing building with 2 units out of the 7 units in this secluded bayside condo complex with vacation rental licenses and boat dockage for 2 boats. This concrete building w/concrete roof is comprised of two updated units, each having 2 bedrooms, 2 baths, living room, updated kitchen and stainless steel appliances, plus shared laundry room. (1 ground level unit and 1 upper level unit). The protected boat basin w/water & electricity is for boats up to 26 and boat ramp for launching boats up to 18. Enjoy year round spectacular sunsets from the jetty!

$740,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
2 Bed, 2 Baths, 908 SqFt Days Listed: 151
-2.50% ($19,000) 1 Price Change : Last Change 44 Days Ago
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges

Motivated Seller!!! World Famous Cheeca Lodge & Spa Resort. Premier Income Producing Unit , approximately 50k a year. Only One of four Luxurious 2/2 available. Cheeca handles all vacation rentals making your investment hassle free. 28 exquisite and exclusive days for owners use. Enjoy 5 star dining, beach, spa, pools, 9-hole par 3 golf course, Camp Cheeca for the kids, and so much more!

$739,000
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
2 Bed, 2 Baths, 1,275 SqFt Days Listed: 55
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Slip,Dock Privi

Beautifully updated Beacon Reef 2/2 condo with expansive views of the ocean in the very best location in downtown Islamorada. Close to all the most popular spots by land or sea! Jump in your boat and head straight out oceanside to the reef or Alligator Light for fishing, diving or snorkeling, or anchor up and relax on the famous Islamorada sandbar a mile away. You can also slip under the bridge to fish Florida Bay only minutes away. Take your boat or a quick car ride to enjoy the best waterfront bars and restaurants in downtown Islamorada. This condo was updated with a gorgeous custom kitchen and adjoining bar area perfect for entertaining. Both baths have been completely updated and the main bedroom door was even moved to maximize the ocean view from the living room. Must see!

$729,000
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
3 Bed, 3 Baths, 1,275 SqFt Days Listed: 74
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock,Dock P

This gorgeous completely updated unit has everything to offer for the meticulous buyer, its own storage for outside toys and/or owners closet underneath, a gym, lushly landscaped grounds with astonishing pool, chiki hut and a superb dock with slips, ice machines and fish cleaning stations....This property has it all....

$725,000
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
2 Bed, 2 Baths, 1,275 SqFt Days Listed: 102
-8.81% ($70,000) 2 Price Changes : Last Change 8 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock36ft.

Lets hit the beach! This outstanding direct oceanfront condo features two bedrooms and two baths, a renovated kitchen, and open water views. Located in the heart of Islamorada, Beacon Reef Condominium offers unparalleled amenities including a large sculptured pool, dockage, tiki, and amazing sunrises. A spiral exit staircase and a separate storage area for your gear complete this package.

$719,000
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
2 Bed, 2 Baths, 1,275 SqFt Days Listed: 44
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Slip,Dock Privi

Islamorada Beacon Reef Beauty! Expansive ocean views from this tastefully updated residence on the 4th floor of the south building. Tropical resort style pool, sand beach, full gym overlooking the ocean, and beautiful dock with slips for your boat. Beacon Reef has everything. The kitchen features granite counter tops, Maple cabinets, stainless appliances, and a breakfast bar. Youll fall in love the minute you enter the front door.

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 09-28-2020.

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Key Largo, Florida 33070

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