Divider
Content Divider

Lower Matecumbe Waterfront Homes for Sale, Single Family Houses, Open Water, Ocean and Bay / Gulf Views

Total Listings 47
Order By:

$9,985,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
8 Bed, 8 Baths, 5,392 SqFt Days Listed: 126
-8.39% ($915,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat LiftConcrete

Nestled in the exclusive Safety Harbor enclave of Islamorada, this stunning Gulfside estate offers an unparalleled blend of luxury and tranquility. Situated on a prime point, the property boasts breathtaking open water views and the added advantage of protected dockage, making it a boaters paradise. With a concrete seawall, two boat lifts equipped with power and water, and a fish cleaning station, this home is perfectly appointed for waterfront living. Easy ocean access through the nearby Channel 5 Bridge adds to its appeal for avid anglers and adventure seekers alike. Inside, the home features eight spacious bedrooms, each with its own ensuite bath, plus two additional half baths for convenience. The master suite is a private sanctuary with a spa-inspired bath, while the open layout showcases spectacular water views through impact windows and sliding glass doors. An elevator ensures effortless access to all levels, and the wraparound balcony invites you to savor unobstructed panoramas. The gourmet kitchen, complete with high-end stainless steel appliances and gas cooktop, is a chefs delight, complemented by an outdoor kitchen for alfresco entertaining. With its seamless indoor-outdoor design and unmatched location, this property is the epitome of luxurious Keys living. Owner/Agent

$10,900,000
Lower Matecumbe
Mat Sandy Beach   - MM: 75.00
4 Bed, 4 Baths, 4,512 SqFt Days Listed: 153
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip,

Discover the unparalleled beauty and tranquility of this Bayfront Estate, nestled on the pristine shores of Lower Matecumbe in the Florida Keys. Surrounded by lush, meticulously landscaped grounds, this exceptional property offers direct waterfront on the crystal clear waters of the Gulf. Experience breathtaking sunsets over the horizon, world-class tarpon fishing just steps away, and private dockage with ample space for multiple boats.Unwind in the stunning infinity pool, blending seamlessly with the serene surroundings. This is a rare opportunity where every moment feels like a dream!Developed with two buildings, splitting the living between the two making this unique design quite special. Embrace this exciting design or modify and create your own design. Blending the two buildings brings all living together. Other treasures of this estate property include a 2 car garage, separate guest suite, expansive indoor outdoor entertaining overlooking the bay, separate concrete building for versatile use, boat lift, boat ramp, German inspired fireplace, electric gate, sprawling green space, and so much more.Owner is ready to sell. What an opportunity!

$12,900,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
6 Bed, 6 Baths, 4,394 SqFt Days Listed: 169
-13.42% ($2,000,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift220ft.

Welcome to BAYVIEW HIDEAWAY a generously sized, COMPLETELY RENOVATED home with top-tier finishes showcasing stunning Florida bay views of calm waters and vibrant nightly sunsets, combining tropical charm with modern luxury--ideal for those in search of a tranquil getaway in an unforgettable PRIVATE setting. Situated on TWO SEPARATE LOTS-each with its own parcel ID--the buildable bayfront lot has endless potential. The price per square foot reflects this extraordinary opportunity. The property features 220+/- FT. OF CONCRETE DOCK, an additional 200+/-ft. of water frontage, THREE BOAT LIFTS, helicopter access, a NEW PRIVATE POOL, and SIX BEDROOMS EACH WITH WATER VIEWS. Ideally located in Islamorada just north of the Channel 5 Bridge with its 65 clearance and 30 minutes from Marathon executive airport, it offers nearly IMMEDIATE ACCESS to the ocean or Intracoastal Waterway, world-class offshore and backcountry fishing, reef diving, and an array of nearby attractions, outdoor activities, and dining--striking a perfect balance of seclusion and accessibility ideal for any boater, angler or water enthusiast!

$15,000,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
10 Bed, 10 Baths, 6,302 SqFt Days Listed: 148
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Lift,Dav

3 HOMES, OVER 100 PROTECTED DOCKAGE & OVER 550 NATURAL OCEANFRONT BEACH ~Fall in love at first sight as you step into this natural beauty with over a quarter mile of pristine white sand beach that kisses the edge of the Atlantic Ocean. Offered for the very first time, this one of a kind legacy property beckons you to bask in original elements of the Florida Keys way of life at Kids Cay. Three charming homes; 4 bedroom main house plus 4 bedroom guest house and 2 bedroom caretakers cottage. This tropical and tranquil estate offers ample and protected concrete dockage (104 feet and 34 feet) and oceanfront observation pier. Extra wide and spacious porches adorn every corner of the classic homes and are a seamless blend of indoor and outdoor living maximizing the infinite open water views and constant ocean breezes. Enjoy complete privacy lounging by the resort-style pool or stroll barefoot along your private beach, and nature preserve; a sanctuary for plethoras of beautiful native birds. This estate is the epitome of true island living and serenity and beautifully lends itself to photo shoots, movies, weddings and luxury weekly rentals. This offering is for the south side (over 4 acres upland plus ocean bottom parcel) of property and over 550 of beachfront. See MLS#604054 for entire offering.

$17,000,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
7 Bed, 7 Baths, 5,900 SqFt Days Listed: 36
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Welcome to Paradise Islamorada. New construction. 7 bedroom. 7 bathroom. Ready to move in. Make your dream a reality. Mile marker #75. Land 2 acres beachfront lot.

$20,000,000
Lower Matecumbe
Matecumbe Ocean Bay   - MM: 75.00
10 Bed, 10 Baths, 6,302 SqFt Days Listed: 866
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Lift,Dav

Fall in love at first sight as you step into this natural beauty with over a quarter mile of pristine white sand beach that kisses the edge of the Atlantic Ocean. Offered for the very first time, this one of a kind legacy property beckons you to bask in original elements of the Florida Keys way of life at Kids Cay. Three charming homes; 4 bedroom main house, separate 4 bedroom guest house and 2 bedroom caretakers cottage. This tropical and tranquil estate has nearly 8.5 acres of upland plus 7.98 acres of ocean bottom plus ample and protected concrete dockage (104 feet and 34 feet) and oceanfront observation pier. Extra wide and spacious porches adorn every corner of the classic homes and are a seamless blend of indoor and outdoor living maximizing the infinite open water views and constant ocean breezes. Enjoy complete privacy lounging by the resort-style pool or stroll barefoot along your private beach, and nature preserve; a sanctuary for plethoras of beautiful native birds. This estate is the epitome of true island living and serenity and beautifully lends itself to photo shoots, movies, weddings and luxury weekly rentals. Also being offered with south side only for $15m see listing #613236.

$31,200,000
Lower Matecumbe
Misc Lower Matacumbe   - MM: 76.00
8 Bed, 8 Baths, 10,228 SqFt Days Listed: 16
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp1

Spectacular 1.65-Acre Bayfront Estate in Islamorada, Florida Keys |
8 Bedrooms | 9.5 Bathrooms | 10,228 Total Sq Ft | 150 Waterfront | Dockage | Pool | BeachWelcome to a rare offering in the heart of the Florida Keys--this 1.65-acre gated bayfront compound in Islamorada combines timeless island luxury with modern amenities and endless water views. With 150 feet of private waterfront, dockage, boat ramp, private beach, two pools, and lush, mature tropical landscaping, this estate is a true Keys sanctuary.The 7,562 sq ft main residence boasts 5 spacious bedrooms, 5.5 bathrooms, an office, and exquisite finishes throughout. The gourmet kitchen features marble and dolomite countertops, a custom mosaic tile backsplash, built-in Miele coffee system, wine dispenser, 36 Wolf gas cooktop, four Sub-Zero refrigerators, and two laundry rooms. A stunning 180-bottle glass wine cellar, handmade wood bar with wood sink, Sonos sound system, and living room with blackout shades to enhance the entertaining potential.Additional highlights include an elevator, Lutron lighting system, Toto toilets, expansive covered porches with panoramic open bay views, an outdoor kitchen complete with Italian brick pizza oven, Evo flat grill, and smoker, as well as a tackle room and 4-car garage.The 2,666 sq ft guest house offers a private gated drive, 3 bedrooms, 4 bathrooms, a private pool, and a fully equipped kitchen with JennAir appliances, making it ideal for hosting guests or extended family in complete privacy.With two gated driveways, serene lawns, and a high-end tropical ambiance, this estate seamlessly blends privacy, prestige, and paradise.A one-of-a-kind legacy property - experience the ultimate Florida Keys lifestyle.

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 06-16-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA