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

Total Listings 24
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80639  Old Highway  101 For Sale, MLS 590401
$3,495,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
4 Bed, 4 Baths, 2,997 SqFt Days Listed: 15
-0.14% ($5,000) 1 Price Change : Last Change 12 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Welcome to Maison Residences, your private oceanfront retreat in Islamorada. Enjoy open ocean views as soon as you step inside the front door! The view widens as you walk through the kitchen and dining area to the living area and the open lanai. This same view can be enjoyed from the luxurious master bedroom and balcony. Nature lovers can watch the wading birds feeding in the shallows, the pelicans diving for breakfast and porpoises playing without leaving your porch. Views of the lawn, palm trees, beach, dock and ocean will fill our mind and entice you to come back often. This smart home was finished with great attention to detail and features 10 ft. ceilings, 9 ft. doors, 2 AC units with 3 zones, Wolf and SubZero appliances, privately keyed elevator, 86 ft. resort style pool,

80639  Old Highway 307 For Sale, MLS 590135
$1,125,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
3 Bed, 3 Baths, 2,251 SqFt Days Listed: 35
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

In the heart of Islamorada, this beachfront townhouse style 3 bdrm/3bth 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 Cheeca Lodge and Spa, Art District, restaurants, shopping, free shuttle throughout the island.

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

83201  Old Highway 304 For Sale, MLS 590035
$549,000
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
2 Bed, 2 Baths, 1,275 SqFt Days Listed: 41
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock38ft.

Welcome to Beacon Reef! One of Islamoradas most sought after oceanfront communities featuring resort style pool, beach, and gorgeous custom dock beautifully lit at night; all surrounded by meticulously maintained landscaping. Perfect location to depart from for offshore or backcountry fishing, diving, snorkeling, enjoying a Sandbar cruise or a quick visit to Alligator Light. This unit boasts recently updated baths, as well as a detail oriented open kitchen with contrasting dark maple and white cabinets, all stainless appliances, large island area for culinary creations, pantry/storage, breakfast or cocktail bar, with many unique decorative touches. Enjoy the ocean breeze (and the sunrise if so inclined) from the covered balcony, as well as from the main bedroom. Hop on your bike, walk to,

79901  Overseas Highway 420 For Sale, MLS 589958
$335,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
1 Bed, 1 Baths, 827 SqFt Days Listed: 45
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp

This well priced condo at the Palms of Islamorada is being sold FURNISHED! Just bring your toothbrush to start enjoying the Florida Keys lifestyle. Tiled throughout with nicely updated kitchen and baths. Impact windows and doors are another upgrade to this lovely condo. There is one covered, assigned parking space and plenty of additional parking for friends. The complex amenities include an oceanfront heated pool and spa, his and hers exercise rooms, an oceanfront Tiki hut for outdoor entertaining and grilling and community room. Storage for Kayaks and Paddle Boards is on a first come basis.

82236  Overseas Highway 7 For Sale, MLS 589722
$491,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
2 Bed, 2 Baths, 616 SqFt Days Listed: 58
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip

WEEKLY RENTALS W/BOAT DOCKAGE-Great Investment Property with transient zoning license. This Bayside 2 Bedroom 2 Bath Updated Condo on 2nd Floor is located right in the Heart of Islamorada near great restaurants, entertainment, and shopping. Enjoy year round spectacular sunsets! HOA includes Boat Basin, 1 boat slip in Marina to accommodate up to 26 boat for each unit, boat ramp, and storage, plus laundry room in building.

82236  Overseas Highway 6 For Sale, MLS 589720
$491,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
2 Bed, 2 Baths, 616 SqFt Days Listed: 58
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Boat Slip,

WEEKLY RENTALS W/BOAT DOCKAGE-Great Investment Property with transient zoning license. This Bayside 2 Bedroom 2 Bath Updated Ground Level Condo is located right in the Heart of Islamorada near great restaurants, entertainment, and shopping. Enjoy year round spectacular sunsets! HOA includes Boat Basin, 1 boat slip in Marina to accommodate up to 26 boat for each unit, boat ramp, and storage, plus laundry room in building.

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!

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.

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.

79901  Overseas Highway 316 For Sale, MLS 588948
$799,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
3 Bed, 3 Baths, 1,484 SqFt Days Listed: 97
-5.99% ($50,900) 1 Price Change : Last Change 50 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Beauty, tranquility and paradise abound in this Direct Ocean Front Condo. Featuring almost 1500sf of living space, this spacious 3 bedroom, 2 full bathroom condo directly overlooks the breathtaking crystal blue waters of the Atlantic Ocean and has expansive views from every room. You cant beat the location in the Heart of Islamorada where you can walk, ride your bike or boat to all restaurants, art galleries and shopping that this top world destination has to offer. Open floor plan for your living and dining area which again has amazing views. Relax on the over sized and private balcony, also great for entertaining. Updated kitchen with granite counters, solid wood cabinetry and lots of storage. Superb amenities, which include pool, hot tub, kayak storage, gym, ocean front lounging.

79901  Overseas Highway 506 For Sale, MLS 588918
$469,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
2 Bed, 2 Baths, 981 SqFt Days Listed: 98
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Gorgeous Ocean View Condo with Newly Remodeled Kitchen and Bathrooms. Top Floor two bedroom two bathroom condo with a private covered balcony. All windows and doors are impact resistant, brand new AC and water heater. Palms of Isla features an oceanfront pool, hot tub, tiki bar/grill area, sandy beach, boat ramp, indoor gym facility, kayak/paddle board launch and storage area. Secured gate entrance, covered assigned parking and plenty of parking for your guests. Home away from home or use as an excellent vacation rental property.

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.

79901  Overseas Highway 416 For Sale, MLS 588574
$979,900
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
3 Bed, 3 Baths, 1,484 SqFt Days Listed: 124
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.

79901  Overseas Highway 507 For Sale, MLS 588507
$459,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
2 Bed, 2 Baths, 981 SqFt Days Listed: 127
-2.34% ($11,000) 1 Price Change : Last Change 70 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat RampConcrete

Oceanfront, Top Floor, Completely Renovated 2 Bedroom, 2 Bath Condo Unit at The Palms of Islamorada. All the work has been done, no need for the expensive and timely pain of a condo remodel. New kitchen and baths, new windows and shutters, new AC and hot water heater. The complex features an oceanfront pool and hot tub, a relaxing beach, his and hers gyms, an outdoor grill and tiki area, kayak/SUP launch ramp and gorgeous open-water views of Alligator Lighthouse and Terra Key. The Palms is conveniently located near Lazy Days Restaurant, Midway Cafe and Coffee Bar, Amara Cay Resort and Bud n Marys Marina. Downtown Islamorada, offers a wide array of restaurants and shops and is less than a mile away.

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.

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 72 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.

80639  Old Hwy Highway 403 For Sale, MLS 588059
$2,995,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
3 Bed, 3 Baths, 3,274 SqFt Days Listed: 156
-7.85% ($255,000) 2 Price Changes : Last Change 93 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.

81801  Overseas Highway 735 For Sale, MLS 586656
$339,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 358 SqFt Days Listed: 258
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Here is your chance to own a great, income-producing piece of the iconic Cheeca Lodge & Spa in the heart of Islamorada. This beautiful double queen bedded resort view room is a great investment and can be your vacation spot for up to 28 days per year! Cheeca has long been the resort of choice for families, romantic getaways and more than one President. You will have your choice of 3 great restaurants, 2 bars, 2 pools (with a 3rd coming soon), 6 lighted tennis courts, a 9-hole, par 3 golf course, a Spa and workout facility, along with Camp Cheeca for kids. This unit has experienced over 80% occupancy and offers a great return on investment.

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 188 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.

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Key Largo, Florida 33070

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