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| Address | Bed / Bath | Listing Price |
|---|---|---|
100 List Street
Islamorada Bayfront Estate with Dockage & Open Bay Views... all in downtown Islamorada within walking distance of your favorite spots! Custom built by the current owner in 2014, this concrete fortress is storm-resilient and also offers a host of sustainability features including a whole-house solar
Living Area:
3019 Sqft.
|
3
Beds,
3
Baths
|
$5,900,000 |
82719 Old Hwy
The Chateau on the Ocean is a private oceanfront estate in Islamorada, where world-class design meets unmatched amenities. Completely renovated in 2022, this gated estate spans 10,182 sqft & offers 7 bedrooms & 9.5 baths. Set along a pristine private coastline, it features a 100-ft private dock & an
Living Area:
10182 Sqft.
|
7
Beds,
10
Baths
|
$24,995,000 |
191 Carroll Street
Newly Remodeled 3-Bed, 3-Bath Home in the Heart of IslamoradaThis newly remodeled 3-bedroom, 3-bath home is located on Upper Matecumbe in the heart of Islamorada, offering the perfect blend of modern comfort and island living. The unique layout features 1 bedroom and 1 bathroom downstairs, and 2 bed
Living Area:
1550 Sqft.
|
3
Beds,
3
Baths
|
$1,250,000 |
189 Carroll Street
Newly Remodeled 3-Bed, 3-Bath Home in the Heart of IslamoradaThis beautifully remodeled 3-bedroom, 3-bath home is located on Upper Matecumbe in the heart of Islamorada, offering the perfect combination of luxury, comfort, and island style--all on one level. The open-concept floor plan features a spa
Living Area:
1525 Sqft.
|
3
Beds,
3
Baths
|
$1,250,000 |
91 Iroquois Dr
Experience the ultimate Keys lifestyle in this luxurious Islamorada retreat on Lower Matecumbe Key. Enjoy breathtaking ocean views, protected boat dockage with two lifts, and resort-style amenities. This 4BR/5BA home showcases solid concrete construction, impact windows & doors, Interlock aluminum r
Living Area:
4048 Sqft.
|
4
Beds,
5
Baths
|
$7,995,000 |
82749 Old Highway
Welcome to a one-of-a-kind oceanfront estate located along the iconic Old Highway in Islamorada -- a rare offering with 200 feet of oceanfront shoreline, a private jetty with dockage, and breathtaking panoramic views of the Atlantic Ocean. This elegant coastal retreat blends indoor-outdoor living w
Living Area:
1485 Sqft.
|
3
Beds,
3
Baths
|
$7,750,000 |
129 S 129 Hammock Road
Tucked away behind lush tropical vegetation, this charming ground-level CBS home with plenty space to park your boat offers the ultimate in privacy while placing you right in the heart of Upper Matecumbe - Islamorada's most coveted island. The 2-bedroom, 1-bath layout is cozy yet solid, with a spaci
Living Area:
882 Sqft.
|
2
Beds,
1
Bath
|
$699,000 |
33 Pen Key Drive
Legacy Retreat in Islamorada - Gated Waterfront Estate with Marina, Pool & Sunset Point in Exclusive Private Bayfront Club Community. Discover the pinnacle of tropical living in Islamorada, where privacy, elegance, and world-class amenities converge. This expansive Key West-style residence is nestl
Living Area:
4537 Sqft.
|
3
Beds,
3
Baths
|
$2,495,000 |
81250 Overseas Highway 5
Only sophistication and class represented in Islamorada's most exclusive development, Tarpon Flats. This rare offering has underwent a full high-end renovation to satisfy the most distinguished buyer. The elegant paver driveway leads up to pristine grounds showing off it's manicured landscaping. One
Living Area:
2336 Sqft.
|
4
Beds,
3
Baths
|
$2,850,000 |
130 N Hammock Road
Island Life in the Heart of Islamorada, a ground-level, 3 bed, 2 bath home with all the charm and comfort you need to enjoy life in the Keys. Solid CBS construction with Bahama shutters, central air, and an updated kitchen ready for entertaining. The yard is fully fenced plus there's a large bonus s
Living Area:
1376 Sqft.
|
3
Beds,
2
Baths
|
$739,000 |
82260 Overseas Highway
This renovated treehouse retreat is your picture-perfect getaway or forever island home! Discover a rare opportunity to own a beautifully reimagined Keys haven in the heart of Islamorada. Nestled among lush tropical foliage on an expansive 15,000+ sq ft lot, this fully renovated CBS residence offers
Living Area:
2314 Sqft.
|
3
Beds,
3
Baths
|
$899,000 |
81250 Overseas Highway 2
Experience refined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront enclave. This intimate, gated community consists of just 12 luxury residences spread across four beautifully landscaped acres. A stately paver driveway welcomes you to impeccably manicured grounds, where the char
Living Area:
2072 Sqft.
|
3
Beds,
3
Baths
|
$2,850,000 |
82762 Overseas Highway 3
Open Bay Views, Boat Dockage, Pool and more... all in the Heart of Downtown Islamorada! Have you been dreaming of living downtown, but can't find a home with dedicated boat dockage and open water views? If so, this custom 4/4 home in Madeira Bay is your dream come true! Enjoy open water views from t
Living Area:
2728 Sqft.
|
4
Beds,
4
Baths
|
$2,195,000 |
82768 Overseas Highway
Welcome to Serenity Cay, an exquisite Balinese-inspired estate where tranquility and luxury meet the endless beauty on the Florida Bay. A true masterpiece of engineering and design, this sprawling waterfront residence on nearly 4 acres offers an unparalleled blend of tropical elegance, sophisticated
Living Area:
6935 Sqft.
|
7
Beds,
10
Baths
|
$25,000,000 |
105 Carroll Street 6
NEWEST DEVELOPMENT IN DOWNTOWN ISLAMORADA!! Come preview finished units NOW. Only ONE HOUSE LEFT. An exclusive, gated enclave on the Atlantic Ocean, Oceanside is nestled between the Cheeca Lodge and the Caribbean Resort, offering the very best of location, privacy and island living. Low maintenan
Living Area:
2576 Sqft.
|
4
Beds,
5
Baths
|
$3,150,000 |