Browse All High Point (89.0) Properties for Sale

4 Beds ⋅ 5 Baths ⋅ 620986 MLS

Experience the ultimate Islamorada waterfront lifestyle in an exceptional contemporary custom bayfront residence, designed by its current owners, with sophisticated architecture, exceptional construction, and premier boating amenities. Perfectly positioned on a cul-de-sac to capture spectacular year-round sunsets across Florida Bay, the tri-level residence offers approx. 3,200 Sqft of living space, an additional 800 Sqft of covered, tiled balconies, four bedrooms, each with an en suite bathroom, plus a convenient half bath. Natural stone flooring, custom cabinetry, quality finishes, and an elevator serving all interior living levels. Built for lasting durability, the home features reinforced concrete construction, galvanized reinforcing steel, a solid concrete roof, impact windows & doors plus automatic hurricane curtains protecting the main waterfront terrace. The spectacular 1,400 Sqft rooftop sun deck crowns the residence, showcasing panoramic views across Florida Bay, unforgettable year-round sunsets, & a fire pit for entertaining or relaxing under the stars. Designed for the boating enthusiast, the property offers immediate deep-water access, two boat lifts at +/- 25,000 and 12,000 pounds, and an enclosed tackle room/workshop for fishing gear and marine equipment. Low-maintenance grounds feature artificial turf, coral rock hardscaping, and irrigated tropical landscaping. The spacious backyard offers ample room for a future resort-style pool overlooking Florida Bay adjacent to the existing chickee hut. A spacious double covered carport with 9.5-foot ceilings provides generous parking for multiple vehicles, trailers, golf carts & recreational equipment. Combining contemporary custom design, exceptional concrete construction, expansive indoor/outdoor living, premier boating amenities, breathtaking sunset views, and endless opportunities for waterfront entertaining, the residence represents luxurious bayfront living at its finest in the Florida Keys.

144 N Rolling Hill Rd, Islamorada

$3,000,000

2 Beds ⋅ 2 Baths ⋅ 605393 MLS

If you're looking for a run-of-the-mill, rectangle of a house, stop reading now. This unique home, custom designed and built by an architect, takes full advantage of its spectacular location on Florida Bay. A second floor promenade mimics the peninsula on which the house sits. Huge picture windows bring in the glorious water views. Antique porthole windows in the primary bedroom offer a glimpse of the water and the starry sky. Even the showers offer views of the Bay. Recent updates provide both a more open feel through the kitchen to the wide water views and more privacy for the two bedroom suites. All new appliances, a concealed TV lift cabinet, a new stairway and a butler's pantry improve accessibility and convenience. The property is a boater's dream, with direct water access to the Bay and to the ocean through Tavernier or Snake Creek. You'll have your own 30-foot dock with a hydraulic boat lift in a protected canal, plus a basin surrounded by a 182-foot long electrified L-shaped wooden dock. The first floor gives you storage and a two-car garage with plenty of room for your workshop, fishing rods and water toys. Feel like a trip to Miami? Take your boat -- or your yacht! It's just a few hours away. (Of course, it's under two hours by car -- but a lot less fun.) The house is built like a fortress. Concrete construction, impact windows, accordion shutters, a whole house generator and even a cistern will keep you secure no matter the weather. Recent upgrades like a new AC system will keep you comfortable year-round. The lovely waterfront High Point neighborhood is safe with a Sheriff's substation nearby. It's an ideal home for anyone who loves boating and loves the water.

150 N Rolling Hill Rd, Islamorada

$760,000

3 Beds ⋅ 2 Baths ⋅ 606141 MLS

Your Island Retreat Awaits: Charming Islamorada Home Where Sunsets Paint the Sky and Breezes Whisper Secrets. This 3-bedroom, 2-bathroom gem boasts a concrete roof, impact windows, shutters, and stainless steel appliances. Safety meets style—your sanctuary awaits. Sunset Watchers' Paradise: Homeowners' park access—launch your boat, paddle your kayak, or simply soak in the world-famous sunsets. With a backyard that dreams are made of: Picture a sparkling pool, oversized and ready for lazy afternoons. And that air-conditioned 'she' or 'he' shed? It's your creative haven. Bunker Chic: All-concrete construction—the roof, the walls—your fortress against worries. Carefree living, one block at a time. Close to shopping, schools, restaurants, and even the hospital. Plus, a quick hop to Miami International Airport. Jet-setter's delight! Founder's Park: Bayfront bliss—sandy beaches, marina magic, and amphitheater vibes. Splash pads, dog-friendly corners, and tennis courts—it's all here. High Point Perks: Private Florida Bayfront access—for strolls or boat ramp adventures. Your slice of paradise, just $100 per year for pedestrian access or $400 annually for the private boat ramp and dock. Schedule a tour, feel the island breeze, and decide: Is this where your heart drops anchor?

111 S Rolling Hill Rd, Islamorada

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High Point (89.0) Real Estate & Homes

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