Browse All Matecumbe Ocean Bay (75.0) Properties for Sale

620931 MLS

Rare oceanfront Pristine parcel offering approximately 0.56 acres (100 x 244') with 100 feet of Pristine Atlantic Shoreline and active building permit for your dream home/estate. Features a new 80-plus foot dock with a tiki hut and direct access to world-class fishing, diving, snorkeling, and boating. Enjoy sweeping sunrise views over the beautiful Atlantic Ocean and sightlines to the iconic Alligator Reef Lighthouse. Situated on prestigious Millionaire's Row and adjacent to protected preserve land for privacy. Directly across to famous Robbie's Marina and market place ,dining, shopping, and local attractions. An exceptional setting to build a custom waterfront estate in one of Islamorada's most desirable location.'

77481 Overseas Hwy, Islamorada

$29,000,000

4 Beds ⋅ 6 Baths ⋅ 620394 MLS

Villa Lago is an Italian-inspired waterfront estate positioned along 220 feet of pristine Florida Bay frontage in Islamorada. Offering 8,194 SF of living space on 1 acre of bayfront property, a dramatic arrival unfolds beneath soaring 30ft ceilings, leading into a grand living space framed by turquoise bay views. An arcaded hallway with a hand-tiled barrel-vaulted ceiling connects interiors featuring Italian finishes, exquisite marble details, five fireplaces, hand-painted ceiling frescoes, and a one-of-a-kind imported tile roof. Florentine quatrefoil windows, Juliette balconies, wrought-iron railings, copper rain gutters, and hand-carved marble corbels enhance the home's architectural character. The floor plan includes four bedrooms, with three guest suites on the main level and a private third-floor primary retreat featuring two fireplaces, an office, tea room, sitting room, custom walk-in closet, private laundry room, spa-inspired bath, and balconies overlooking the living spaces below. The chef's kitchen is appointed with Viking, Miele, U-Line, and Sub-Zero appliances, a walk-in pantry, and dedicated prep kitchen. A pass-through window connects to the outdoor kitchen with a Viking grill, refrigeration, ice maker, bar seating, and covered dining overlooking the pool, beach, and bay. Additional spaces include a formal dining room with a hand-painted ceiling fresco, wellness room, sauna, private theater with wet bar, and a billiards lounge with mahogany coffered ceilings and coconut wood flooring. Outside, an infinity-edge pool, sunken gazebo with swim-up seating, putting green, fountains, and tropical landscaping. Deep-water dockage, white-sand beach, and crystal-clear waters provide immediate access to world-renowned fishing, diving, snorkeling, and boating. Additional features include an air-conditioned boat room, skiff ramp, 4,000+ SF collector's garage, elevator servicing all 3 levels, Control4 smart home integration, Sonos, and secure walled & gated grounds.

75090 Overseas Hwy, Islamorada

$3,999,999

2 Beds ⋅ 2 Baths ⋅ 619064 MLS

Estate Opportunity Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, and generous waterfront dockage--all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. An existing legal nonconforming home with a waterfront swimming pool currently sits on the property and may be used as a residence or rental while architectural plans and permits are finalized, offering flexibility during the planning process. For buyers who understand the value of land in the Florida Keys, this offering represents something increasingly difficult to find: the opportunity to create a custom waterfront estate tailored entirely to your vision, rather than inheriting someone else's. A remarkable parcel for a remarkable build.

77340 Overseas Hwy, Islamorada

$1,600,000

1 Beds ⋅ 3 Baths ⋅ 616210 MLS

This property was originally commercial and was changed by the Village of Islamorada without notifying the owner. A land use attorney is workiing on fixing the issue so it can be commercial again. Right now the land was changed to native residential. This property is 3.2 Acres, with 1 of those acres being hardwood so it cannot be built on. 2 acres have been scarified and was being used as tennis courts with a club house on it.

76800 Overseas Hwy, Islamorada

$1,650,000

2 Beds ⋅ 2 Baths ⋅ 611759 MLS

Welcome to this charming Old Florida-style cottage, an ideal weekend retreat nestled on Lower Matecumbe Key in Islamorada! This property is set on nearly half an acre, boasting an impressive 100 ft of private beach frontage directly on the crystal-clear ocean. This cottage is a perfect fixer-upper opportunity, offering you the chance to renovate and personalize the existing structure or build your dream home on this stunning piece of prime real estate. Step inside to discover two spacious bedrooms and two full bathrooms. The interior features beautiful beamed and tongue-and-groove ceilings, adding a touch of character and warmth to the space. Imagine starting your mornings with a cup of coffee or unwinding in the evenings with a glass of wine, all while enjoying breathtaking views of the magnificent Atlantic Ocean. The gentle ocean breezes create a serene atmosphere, perfect for quiet contemplation and entertaining friends and family. With its prime location and charming features, this cottage is a rare find that invites you to embrace the laid-back Florida Keys lifestyle. Don't miss your chance to make this idyllic getaway your own!

75621 Overseas Hwy, Islamorada

$16,000,000

10 Beds ⋅ 11 Baths ⋅ 604054 MLS

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 caretaker's 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.

141 Cortez Dr, Islamorada

$2,650,000

616329 MLS

100 x 717 ft lot approximately 1.66 acres ocean front with real sand on the beach on Lower Matecumbe in Islamorada MM76.2. Remains of prior Utility building on property. incredible location for an ocean front beach front micro-estate in the Village of Islamorada.

76291 Overseas Hwy, Islamorada

$1,500,500

3 Beds ⋅ 3 Baths ⋅ 614479 MLS

Escape to a dreamy Florida Keys paradise with this beautiful 3-bedroom, 2.5-bathroom home situated at the end of a tranquil street. This 1,548 sq.ft. canal-front haven blends comfort with classic Keys charm, making it an ideal vacation spot or a picturesque place to call home. Upon arrival, you'll be greeted by a nicely appointed lot, 2 covered parking spaces, and charming exterior that invites you to step inside. The home's interior features a spacious kitchen equipped with top-of-the-line appliances, including a subzero refrigerator. The backyard overlooks the tranquil canal, with 2 boat lifts catering to the nautical enthusiast, & offering direct ocean access. Your dream of a waterfront oasis is waiting for you.

139 Cortez Dr, Islamorada

Start Your Search

Matecumbe Ocean Bay (75.0) Real Estate & Homes

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Matecumbe Ocean Bay (75.0), Islamorada FL. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!