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$4,500,000
4 Beds ⋅ 4 Baths ⋅ 614893 MLS
Enjoy endless ocean views and direct access to the white sandy beaches of Islamorada from this oceanfront retreat. Behind your own private gated entrance, this solid concrete block home offers four bedrooms, four full bathrooms, and a bonus space. Inside, hardwood floors run throughout an open layout featuring a breakfast nook, dining bar, and spacious living area -- ideal for entertaining. The chef's kitchen is equipped with stainless steel appliances, a gas stove, and modern finishes. The master suite includes a private balcony overlooking the updated saltwater pool and a jetted tub for ultimate relaxation. This one-of-a-kind property also allows weekly rentals, making it a strong investment in one of the Keys' most sought-after locations.

75761 Overseas Hwy, Islamorada
$1,675,000
3 Beds ⋅ 3 Baths ⋅ 618050 MLS
Discover island living at its finest in this beautifully remodeled 3-bedroom, 3-bath ''Florida Modern'' CBS home, ideally located in the desirable Lower Matecumbe Beach neighborhood of Islamorada. A light-filled open-concept layout seamlessly connects the living, dining, and kitchen areas--perfect for entertaining or relaxed island living. The home features three spacious bedrooms and three full bathrooms, including a luxurious primary suite with a sleek modern en-suite bathroom and a large walk-in closet. A versatile bonus room offers endless possibilities as a media room, den, office, or children's retreat. The oversized gourmet kitchen is a chef's dream, showcasing brand-new high-end stainless steel appliances, elegant quartz countertops, and generous storage. Impact-resistant windows and sliding glass doors provide peace of mind while enhancing the home's clean, contemporary style. Step outside to your private backyard and enjoy peaceful sunrise views or savor coffee and cocktails beneath the shaded gazebo. Boaters will love the newly decked 60-foot dock, offering immediate access to both the Atlantic Ocean and Florida Bay. From watching manatees glide by to cleaning the day's catch at the large fish station, every detail is designed for waterfront living. An added bonus is the voluntary HOA, which provides access to a wide sandy beach, known as a turtle-nesting haven. Welcome to your place in paradise. 🌴

159 Iroquois Dr, Islamorada
$3,495,000
4 Beds ⋅ 5 Baths ⋅ 616523 MLS
Welcome to Your Florida Keys retreat or income-producing rental, with 7-day rentals approved! Maison Residences presents its final developer unit, #201, offering 4 bedrooms, 4.5 bathrooms and a spacious open layout designed for true oceanside living. Step off your private elevator into a grand room with soaring 10-foot ceilings and 9-foot stacked sliders that frame endless Ocean views. The open plan connects casual dining, island seating, and a gourmet kitchen outfitted with Sub-Zero and Wolf appliances, Caesar-stone counters, and abundant storage. Oversized covered terrace expand your living space outdoors, where multiple seating areas, TV, a fireplace, and an infrared/gas grill create the ultimate setting for entertaining against the ocean backdrop. The master suite features king-sized accommodations, terrace access, and a spa-inspired ensuite with a luxurious tub and glass shower. Three additional guest suites, 2 with king beds and private balconies, 1 with two twin beds and all with en-suite baths that provide comfort and privacy. This exclusive enclave sits between the Atlantic Ocean and Florida Bay on Islamorada's most vibrant island, Upper Matecumbe Key. Maison's private grounds include over 350 feet of natural sand beach, a 155-foot day pier, lavish 86-foot lagoon-style pool, heated jacuzzi, and space for every water activity. Details such as porcelain tile, U-Line beverage center, Lynx grill, Kohler fixtures, built-in closets, and energy-efficient construction reflect luxury and comfort at every turn. Owning at Maison Residences gives you the rare flexibility to enjoy your home while also generating income. With 7-day minimum rentals approved, you can use your residence as a private retreat and still take advantage of strong demand for luxury short-term stays in Islamorada. This makes Unit 201 not only a lifestyle purchase with world-class boating, fishing, diving, and snorkeling, but also a smart investment opportunity!

80639 Old Hwy Unit 201, Islamorada
$10,900,000
6 Beds ⋅ 5 Baths ⋅ 618449 MLS
A refined expression of waterfront living, this six-bedroom, four-bath residence is set on a desirable over ½ acre lot with panoramic water views from every room. Offering 220+ linear feet of concrete dockage with three boat lifts, the property is exceptionally suited for large vessels with effortless access to the open Florida Bay/Gulf or Ocean via Channel 5 bridge. Two separate parcels included in this sale, opening options in the future for the fortunate owner that resides here. Completely renovated in 2020, the home presents a clean, contemporary aesthetic with Viking appliances, bespoke finishes, and a subtle, neutral palette inspired by the flowing surrounding turquoise waters. A custom saltwater pool equipped with both heater and chiller provides year-round enjoyment for everyone. This Safety Harbor residence delivers both elegance and function for the discerning boater or sunset lover. Impeccably maintained and move-in ready, it offers a rare combination of low-maintenance living, thoughtful design, quiet living and enduring appeal in the Florida Keys. Private showings available by appointment.

186 & 165 Bayview Dr, Islamorada
$7,950,000
8 Beds ⋅ 10 Baths ⋅ 613653 MLS
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 boater's 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 chef's 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

162 Bayview Dr, Islamorada
$11,000,000
4 Beds ⋅ 4 Baths ⋅ 616886 MLS
Commanding 170 feet of private Florida Bay frontage, and situated on over and acre of precious Islamorada land, Eagle Point is a contemporary coastal estate that captures the essence of refined waterfront living. Designed for both serenity and sophistication, the residence blends clean architectural lines with the natural beauty of its tropical surroundings. Gated and beautifully landscaped, the property opens to sweeping open-water vistas framed by swaying palms and fruit trees orchard upon your entrance. Expansive glass walls flood the interiors with natural light, connecting elegant living and dining spaces to the outdoors providing vast screened porched both upstairs and down. The kitchen anchors the home with gorgeous views and function ideal for entertaining or quiet evenings at home. A downstairs flex room and private gym add versatility and wellness to daily life, while multiple rooftop terraces invite sunset gatherings and panoramic bay views. Outside, the resort-inspired amenities continue with a lagoon-style pool, putting green, and ample deepwater dockage with boat lift with Bay to Ocean access in minutes via Channels 2 or 5, offering effortless access to world-class boating and fishing. Just off the edge of the channel lies a rare bayside reef teeming with life and providing snorkeling right off your own dock. Located on the Lower Matecumbe island of Islamorada, Eagle Point balances modern coastal luxury with timeless island tranquility—an estate designed for those who seek both beauty and belonging by the water.

75280 Overseas Hwy, Islamorada
$18,999,000
6 Beds ⋅ 8 Baths ⋅ 615643 MLS
The Oasis Islamorada is a waterfront estate of exceptional scale, conceived as a private Florida Keys compound where architecture, land and water come together spanning nearly 3 meticulously landscaped acres. More than 400' of shoreline, sweeping ocean views and a protected deepwater basin create a marine setting rarely available within a single residential offering. Beyond the grand porte-cochère, the single-level main residence unfolds with soaring ceilings, white oak floors and 12-foot retractable glass walls that dissolve the boundary between interior and oceanfront living. At its center, a chef's kitchen pairs a cascading Calacatta marble island with Thermador appliances and a walk-in pantry, opening seamlessly to expansive living and dining spaces. The main residence includes four bedrooms and six full baths, with an impressive primary suite featuring a fireplace, dual walk-in closets, safe room and spa bath with steam shower. Additional suites offer en suite baths, private balconies and ocean views. A detached two-bedroom, two-bath guest residence brings the estate to six bedrooms while preserving privacy between owners and guests, with substantial grounds offering extraordinary flexibility for the future. Outside, the property assumes the scale of a private resort. Two resort-style pools with spas and sun decks are joined by a summer kitchen, alfresco dining and multiple waterfront terraces. A fitness center with sauna, soundproof theater and golf simulator complete the lifestyle offering. For the yachtsman, the protected deepwater basin accommodates substantial vessels with convenient direct Atlantic access. Built with an uncompromising focus on quality, security and enduring construction, The Oasis is more than an oceanfront residence. It is a legacy-scale Florida Keys estate offering the increasingly rare combination of acreage, significant shoreline, protected deepwater dockage, multiple residences and complete privacy within one extraordinary property

87429 Old Hwy, Islamorada
$439,000
2 Beds ⋅ 2 Baths ⋅ 617381 MLS
WELCOME TO PARADISE BY THE SEA! THIS SPACIOUS CONDO LOCATED IN HIGHLY DESIRED PLANTATION KEY/SLAMORADA ON MILLIONAIRE'S ROW. THIS OCEANFRONT BUILDING OFFERS THE PERFECT BLEND OF COMFORT & CONVENIENCE, THIS BEAUTY FEATURES AN OPEN CONCEPT LIVING AREA THAT LIGHT AND BRIGHT! WELL APPOINTED KITCHEN WITH WOOD CABINETS, & FIRST FLOOR HALF BATHROOM. WALK UPSTAIRS TO A COZY SPLIT BEDROOM FLOOR PLAN FOR PRIVACY. PRIMARY SUITE INCLUDES A WALK-IN CLOSET. OUTSIDE OFFERS COVERED PARKING, PLENTY OF GUEST PARKING, STORAGE UNIT, NEW ROOFS ON BOTH BUILDINGS, LOW MONTHLY MAINTENANCE FEE INCLUDES WATER, HEATED POOL, COMMUNITY ROOM WITH KITCHEN, DOCK/FISHING PIER, , GYM, & SAUNA. WHETHER YOU'RE LOOKING FOR YOUR NEW HOME, A WEEKEND VACATION GETAWAY, OR INVESTMENT PROPERTY, THIS CONDO IS MOVE-IN READY & PERFECTLY LOCATED WITHIN WALKING DISTANCE TO RESTAURANTS AND SHOPPING! EASY ACCESS FROM OLD HIGHWAY OR US 1, THIS DEVELOPMENT HAS IT ALL! NEW ROOFS ON ENTIRE COMPLEX! Driving Directions:

87465 Old Hwy Unit 215, Islamorada
$3,524,000
7 Beds ⋅ 4 Baths ⋅ 618670 MLS
A Keys compound built to enjoy now-grow into the future, or internally convert to a 3,524 sq ft primary home without structural changes, while retaining a Waterfront Transferable Development Right (TDR/TBR) in Islamorada (approx. $650K value). Exceptional opportunity in the coveted White Marlin Beach community at MM74, this canal-front luxury family compound offers rare multi-family autonomy, strong income performance, & resort-style amenities; ideal for an owner-user, investor, or legacy Keys retreat. With two autonomous 2BR/1BA residences upstairs & a separate 3BR/2BA finished, a/c area downstairs, providing privacy, flexibility, & seamless multi-generational or guest use. In total, the compound offers 7 bedrooms & 4 bathrooms, comfortably accommodating up to 24 guests. Designed for both lifestyle & performance, when fully rented, can generate $16,000+ per month in rental income. Zoning & multiple building rights support future expansion or redevelopment. Outdoors, enjoy a resort-style waterfront setting with a private pool, expansive concrete sun deck, outdoor shower, & 70-foot concrete dock with fish-cleaning station, all situated on a 6' control-depth canal with easy access to both bay & ocean waters; ideal for boating, fishing, diving, and paddle sports. Interior finishes reflect modern coastal luxury, including updated kitchens with quartz countertops & stainless appliances, spa-inspired baths with glass-enclosed showers, large-format tile flooring, recessed lighting, & turnkey furnishings. Multiple balconies & patios capture steady breezes & tranquil water views, with manatees frequently passing by. Enjoy private gated access to White Marlin Beach, just a short walk away, offering bay-side sunset views, with the Atlantic Ocean beach also nearby. Grocery stores, marinas, restaurants & bike paths are all within minutes. Rarely does a property offering this level of unity with autonomy, along with amenities, income potential in Islamorada

110 Gulfview Dr, Islamorada
$3,250,000
4 Beds ⋅ 3 Baths ⋅ 616450 MLS
Venetian Shores Has It All! Welcome to your slice of paradise in the heart of Islamorada's most sought-after boating community. This beautiful 4 bedroom, 3 bath coastal retreat is designed for both relaxation and entertainment, featuring 70 feet of deep-water dockage along a 100-foot wide canal - just seconds from open water via Snake Creek. Step inside the front door to access the elevator and interior stairs. Upstairs, the main living area offers 2 bedrooms and 2 baths, a wide open floor plan, and a gourmet kitchen with a large center island, granite countertops, stainless steel appliances, and a dedicated workstation. Enjoy sunset cocktails from the screened canal-side terrace, accessed via impact-rated sliding glass doors. Downstairs, the ground level is a haven for guests and fun - featuring a pool table, a comfortable tv area, 2 more bedrooms and a full bath, laundry room, and garage for all your gear. The backyard is pure Keys magic - complete with a heated pool, tiki hut, hot tub and an expansive deck for sunbathing or relaxing in the shade. Boaters will love the 70 ft concrete dock with a 15,000 lb boat lift, 50 amp shore power and fish cleaning station. This home checks every box for the ultimate island lifestyle - whether you're heading east to the Atlantic or west to Florida Bay's backcountry to enjoy fishing and breathtaking sunsets. Live the dream in Venetian Shores - where the boating is easy and the living is even better.

136 Giardino Dr, Islamorada