Cutthroat Harbor Est (23.0) Homes with Ocean Front Waterfront features

Cutthroat Harbor Est (23.0) Homes with Ocean Front Waterfront features

Welcome to Cutthroat Harbor Estates, a hidden gem nestled in the heart of Cudjoe, Florida, in the picturesque Monroe County. This exclusive waterfront subdivision offers an unparalleled lifestyle that seamlessly blends relaxation, adventure, and stunning natural beauty.

Imagine waking up to the gentle sound of waves lapping against the shore, with breathtaking oceanfront views right outside your window. The homes in Cutthroat Harbor Estates are designed to take full advantage of their prime waterfront locations, featuring expansive outdoor spaces, private docks, and easy access to the sparkling waters of the Atlantic Ocean. Whether you're an avid boater, fisherman, or simply someone who enjoys the tranquility of coastal living, this community is a dream come true.

The architectural styles of the homes here vary, providing a unique charm to the neighborhood. From modern coastal designs to classic Florida-style residences, each property is a testament to quality craftsmanship and thoughtful design. Many homes boast luxurious amenities such as spacious decks, infinity pools, and panoramic terraces that invite you to soak up the sun and enjoy stunning sunsets over the water.

Living in Cutthroat Harbor Estates means you're not just purchasing a home; you're investing in a lifestyle. Enjoy nearby recreational activities, including kayaking, paddleboarding, and fishing right from your backyard. Plus, with the vibrant culture and attractions of the Florida Keys just a short drive away, you’ll have endless opportunities for exploration and enjoyment.

Discover the beauty and serenity of Cutthroat Harbor Estates—where your dream waterfront living awaits!

Newest Cutthroat Harbor Est (23.0) Homes with Ocean Front Waterfront features

$235,000
620165 MLS
This 24 point offshore lot has been evaluated by Monroe County and is eligible for dedication back to Monroe County so you can use those 24 points to add to your ROGO points to assist in receiving a building permit through the ROGO system.

Lot 7 Parcel 10, Cudjoe
$1,725,000
4 Beds ⋅ 3 Baths ⋅ 619558 MLS
Oceanfront living on Cudjoe Key, where broad covered balconies, generous outdoor space, and a private boat launch put Keys waterfront life within reach. This four-bedroom, three-bath home is a study in coastal architecture -- large impact glass doors and windows frame open water views and pull natural light into every room. Soaring 26' ceilings and rich wood beams anchor the open-concept main level, which includes a renovated kitchen, dining space, living room, laundry, and two bedrooms with two full baths. Upstairs, a third bedroom sits at the top of the stairs, and a catwalk leads to the fourth bedroom with ensuite bath and a walkout deck framing panoramic open water views. The home has been restored to its former glory with modern updates layered in -- rustic accents meet open, light-filled spaces that let the oceanfront setting do the talking. Adjacent lot also available for even more ocean enjoyment. Seller financing available: 50% down, 6% for 15 years, no flood or wind insurance required. This home needs to be seen to be fully appreciated. Schedule your showing today.

22542 Jolly Roger Dr, Cudjoe
$499,000
619557 MLS
Oceanfront lot in the Lower Keys overlooking Cudjoe Bay. Build your dream with expansive open-water views and ocean breezes. Prime waterfront setting with incredible potential. No current building permit; buyer to verify process and timelines. Rare opportunity to own a slice of paradise.

22552 Jolly Roger Dr, Cudjoe
$3,300,000
3 Beds ⋅ 3 Baths ⋅ 619314 MLS
Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking water views, where dolphins, rays, and vibrant marine life become part of your daily backdrop. Three luxurious en-suite bedrooms offer refined comfort and privacy, including a main-level guest suite and two upper-level retreats--one featuring a spa-inspired bath with a glass-tiled walk-in shower, the other with a soaking tub overlooking the ocean. Outdoor living is truly resort-inspired, with a private pool, expansive pool deck, and a fully appointed cabana lounge complete with bar, TV, and entertaining space. A rare private beach invites effortless paddle-outs into crystal-clear, opal-toned waters. Multiple balconies and a spectacular rooftop deck provide unforgettable sunrise and sunset views. The chef's kitchen is both functional and striking, featuring an oversized island with unique stone countertops, walk-in pantry, and direct access to a balcony with grilling area. Additional highlights include a poolside grill, ground-level laundry and storage, private dock, and boat ramp with immediate access to world-class fishing and diving. Located just 30 minutes from Key West, this exceptional waterfront retreat delivers the ultimate blend of modern luxury, privacy, and the unmatched lifestyle of the Lower Florida Keys.

1083 Labat Ln, Cudjoe
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