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

Total Listings 18
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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: 56
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.

79901  Overseas Highway 504 For Sale, MLS 585179
$399,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
2 Bed, 2 Baths, 981 SqFt Days Listed: 161
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Top floor, Ocean front condo in Islamorada! 2Bedrooms/ 2Bath unit with 981sf of living space. Covered, open porch with views of the Atlantic Ocean and Alligator Lighthouse in the distance. Complex is gated, has elevator, tiki hut, heated pool, hot tub, kayak / paddle board storage racks adjacent to ramp. Walking distance to dining at Lazy Days & Amara Cay. Marinas close by for charters, boat rentals and boat storage. Monthly rentals allowed.

79901  Overseas Highway 209 For Sale, MLS 585174
$457,500
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
2 Bed, 2 Baths, 981 SqFt Days Listed: 162
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat RampConcrete

Oceanfront 2/2 condo with open ocean views and updated kitchen and baths in a great location in Downtown Islamorada. Relax on your ocean view porch (on the shady afternoon side) overlooking the pool and spa, or use the boat launch to enjoy kayaking or stand-up paddling. Hungry for a nice meal? Lazy Days Islamorada and Amara Cay Resorts Reel Burger are both right next door, or there are endless dining options just a mile away in downtown Islamorada. Love to go diving, fishing or boating? Bud N Marys Marina is also next door! The Palms Condominium is also popular as a monthly vacation rental if you are interested in seasonal rental income. This really is THE location in Islamorada! Call today!

80450  Overseas Highway 301 For Sale, MLS 586366
$495,000
Upper Matecumbe Key Islamorada
Sand Pebbles   - MM: 80.50
2 Bed, 2 Baths, 1,290 SqFt Days Listed: 80
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

SAND PEBBLES in ISLAMORADA! Last unit available! Very Nice single level end unit with views of the Bay. No stairs here, 2 spacious bedrooms and 2 updated baths, Large Screened Lanai. Open kitchen with bar, Large master bath with jetted garden tub and walk in showers make this a place to relax and enjoy the Keys Life! Much pride is given here with Tropical plants and landscaping, including Key lime trees. Marinas and Restaurants nearby. Impact windows, extra parking for boats and trailers. Trail to kayak and enjoy the natural setting. Sparkling pool and tiki hut for BBQs. Additional storage room. Close to Bud n Marys and Lazy Days Restaurant and more popular Islamorada locations. You need to see this unit!

79901  Overseas Highway 205 For Sale, MLS 578165
$649,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
2 Bed, 2 Baths, 981 SqFt Days Listed: 618
+30.06% ($150,000) 1 Price Change : Last Change 575 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Beautifully renovated 2 bedroom condominium in the Palms of Islamorada, walk to fine dining, great fishing boats, both offshore and back country, and a great diving/snorkeling operation. Total restoration down to the studs including new wiring, plumbing, walls, flooring, and ceilings. Offered completely furnished with all amenities TVs, new appliances including washer/dryer. Ready to enjoy starting the day of closing.

83201  Old Highway 221 For Sale, MLS 584344
$775,000
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
2 Bed, 2 Baths, 1,275 SqFt Days Listed: 216
-4.91% ($40,000) 1 Price Change : Last Change 153 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock36ft.

Exquisite direct oceanfront condo in the luxury community of Beacon Reef and located directly on the beach. Walk down your private exterior stairs and you are right on the most beautiful sandy beach in Islamorada. This is the Florida Keys condo with the ocean views and beach you have been dreaming of. The condo offers 2 bedrooms, 2 baths, renovated kitchen and bathrooms, gorgeous balcony, Jacuzzi tub, plenty of closet space, and new appliances. 5 star community amenities include sandy beach, boat dockage, zero-entry pool and hot tub, pier with seating and fishing stations, clubhouse and fitness center with ocean views & poolside tiki hut with grills.

83201  Old Highway 422 For Sale, MLS 585352
$850,000
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
2 Bed, 2 Baths, 1,275 SqFt Days Listed: 149
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock,Boat S

What a View! Rare 2/2 condo with an expansive full ocean view from the minute you open the door! This direct oceanfront residence in beautiful Beacon Reef offers a front row view of the deep blue Atlantic, Alligator Lighthouse and Beacon Reefs one-of-a-kind dock complete with tiki hut and lovely evening lighting. Move-in ready with updated kitchen and baths PLUS a coveted covered parking spot to tandem park two cars or keep your boat/trailer onsite. Beacon Reef is located in downtown Islamorada near everything by land or sea. By boat, the Islamorada sandbar is minutes away along with great fishing and diving. By land, the new Publix is across the street and downtown is less than a mile away with fine dining, shopping, events and local nightlife. Resort-style pool, spa, gym & more!

82762  Overseas Highway 4 For Sale, MLS 582266
$925,000
Upper Matecumbe Key Islamorada
Madeira Bay   - MM: 82.50
3 Bed, 3 Baths, 1,956 SqFt Days Listed: 343
-2.63% ($25,000) 1 Price Change : Last Change 122 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp,

BAY VIEWS & BOAT SLIP IN ISLAMORADA! Waterfront gated enclave of 8 single family homes in Madeira Bay centrally located in the heart of Upper Matecumbe Key. Tri-level 3B/2B residence just one home off the bay, nice water views plus dedicated boat slip w/boat lift directly on Florida Bay. Open floor plan, vaulted ceilings, tiled floors, 2 central ac units, multiple sliding glass doors to bayside patios on both living levels. Ground floor offers carport, above flood guest quarters of 304 SqFt, large sundeck, low maintenance yard with lots of native foliage. Common areas include gated entry, pool, boat ramp & dock. Enjoy this unique peaceful location/setting in the Village of Islands.

81801  Overseas Highway U-416 For Sale, MLS 572769
$960,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 840 SqFt Days Listed: 1039
-10.70% ($115,000) 1 Price Change : Last Change 766 Days Ago
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges525ft

Own one of the most highly sought after units in the main lodge of Cheeca Lodge and Spa. This beachfront property is located in the Heart of Islamorada and is walking distance to great shops and restaurants. Room 416 is an Oceanfront, top floor, corner unit, King Bedroom Suite. *Income Producing (Financials Available)*1031 Exchange*Owners can occupy room up to 28 days per year

81906  Overseas Highway  4 For Sale, MLS 580099
$1,050,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 1,852 SqFt Days Listed: 500
+5.00% ($50,000) 1 Price Change : Last Change 107 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

NEW CONSTRUCTION. CORAL COVE an intimate gated community of 9 site-built homes in the heart of downtown Islamorada. Bayfront with boat basin and dock, each home has its own private pool, state of the art amenities and details plus light and bright natural stone and wood finishes and just steps away from all that Islamorada has to offer.Developers are FL licensed real estate agents.

81906  Overseas Highway  5 For Sale, MLS 580100
$1,150,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 1,852 SqFt Days Listed: 500
+4.55% ($50,000) 1 Price Change : Last Change 107 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

NEW CONSTRUCTION. CORAL COVE an intimate gated community of 9 site-built homes in the heart of downtown Islamorada. Bayfront with boat basin and dock, each home has its own private pool, state of the art amenities and details plus light and bright natural stone and wood finishes and just steps away from all that Islamorada has to offer.Developers are FL licensed real estate agents.

81906  Overseas Highway  6 For Sale, MLS 580101
$1,250,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 1,852 SqFt Days Listed: 500
+4.17% ($50,000) 1 Price Change : Last Change 107 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

NEW CONSTRUCTION. CORAL COVE an intimate gated community of 9 site-built homes in the heart of downtown Islamorada. Bayfront with boat basin and dock, each home has its own private pool, state of the art amenities and details plus light and bright natural stone and wood finishes and just steps away from all that Islamorada has to offer.Developers are FL licensed real estate agents.

80639  Old Highway 302 For Sale, MLS 581214
$1,275,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
3 Bed, 3 Baths, 1,946 SqFt Days Listed: 422
-8.60% ($120,000) 1 Price Change : Last Change 267 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.

79901  Overseas Highway 515 For Sale, MLS 578881
$1,395,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
3 Bed, 3 Baths, 1,484 SqFt Days Listed: 575
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.

82994  Overseas Highway 23 For Sale, MLS 579971
$2,895,000
Upper Matecumbe Key Islamorada
Penn Key Club   - MM: 83.00
3 Bed, 3 Baths, 1,812 SqFt Days Listed: 507
-17.29% ($605,000) 3 Price Changes : Last Change 265 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!

80531  Old Highway  For Sale, MLS 584600
$3,650,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
3 Bed, 3 Baths, 2,044 SqFt Days Listed: 200
-5.66% ($219,000) 1 Price Change : Last Change 136 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None,Other DockageCo

A one-of-a-kind 4.33-acre estate on Upper Matecumbe Key. Enter the gate and follow the classic brick driveway to one of Islamoradas most private settings. The main house, which is above the flood zone, offers two bedrooms and two-and-a-half bathrooms, featuring high beamed ceilings, tile floors, and ocean views. A guest cottage offers one bedroom, one bathroom, and a large sitting room. Watch the colors of beautiful sunrises and incredible sunsets reflect off Alligator Lighthouse from all rooms. Look for tailing bonefish and wading birds, or just sit by the pool and relax--Mother Nature is your living room. A caretakers cottage as well as a guest cottage can be added to the property as of right. Two additional lots have the possibility to be rezoned.

200  Atlantic Street  For Sale, MLS 579361
$7,900,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
8 Bed, 8 Baths, 4,744 SqFt Days Listed: 548
-1.25% ($100,000) 1 Price Change : Last Change 352 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Bunny Key, a premiere historic Islamorada oceanfront plantation. It has been over two decades since this property has been available. Known by its provenance that starts as the LaBranche Fishing Camp in 1937, where it is said the owner and author penned many a fishing tale with the ocean as his muse and passion for fly fishing as his motivation. 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. 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

79775  Overseas Highway  For Sale, MLS 585835
$17,000,000
Upper Matecumbe Key Islamorada
Tea Table   - MM: 79.50
5 Bed, 5 Baths, 3,104 SqFt Days Listed: 119
Single Family - 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 09-19-2019.

Shoreline Properties
92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
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