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$4,999,900
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
$895,000
3 Beds ⋅ 2 Baths ⋅ 617033 MLS
Islamorada Tropical Retreat! Rare 3-bedroom 2-bath split plan condo in desirable Futura Yacht Club. Also available with a 39 ft. boat slip with a 24,000 lb boat lift as MLS#620148 for $1,100,000. Located in the heart of Plantation Key, this condo is in one of the most coveted boating locations in the Florida Keys with crystal clear water, spectacular nightly sunsets and easy boating access to both the bay and the ocean! This spacious condo is nicely updated inside and offers a private balcony overlooking the sports courts, grounds and gardens. Owners and renters alike enjoy the abundant community amenities, including an easy boat ramp, onsite boat/trailer storage, a huge pool with poolside club area, kayak storage, tennis and basketball courts and spacious grounds with shady picnic areas. After a day on the water, grab a cocktail and stroll over to the sandy beach area with sunset seating and shaded hammocks to enjoy spectacular Florida Keys sunsets! This first level condo allows for easy access via a single flight of nearby stairs or take the elevator to the lobby. Don't miss this opportunity and make sure you see the property video and 3D tour. Call today to arrange a private showing.

88540 Overseas Highway Unit 101, Islamorada
$29,500,000
6 Beds ⋅ 6 Baths ⋅ 618152 MLS
A once-in-a-lifetime opportunity to own one of South Florida's most iconic properties. Welcome to Tea Table Key, a breathtaking 15-acre private island estate, accessible by car or by boat, located just minutes from downtown Islamorada and directly across from the famous Alligator Reef Lighthouse. Surrounded by vivid turquoise waters, this extraordinary sanctuary offers complete privacy and a front-row seat to nature's daily spectacle -- herons and egrets gliding overhead, pelicans diving at sunrise, and eagles soaring above your shoreline. Enjoy the rare luxury of total seclusion without sacrificing convenience. Within minutes, you're immersed in Islamorada's finest restaurants, art galleries, and shopping, yet at home you're embraced by the stillness of your own island world. Conveniently located approximately 1 hour and 30 minutes from Miami International Airport, or a 25-minute helicopter or seaplane ride, Tea Table Key offers an unmatched combination of accessibility and exclusivity. The island features a beautifully updated 6-bedroom residence, along with a tennis court and private dockage. Whether you choose to enjoy the comfort of the existing home or envision an entirely new luxury residence, Tea Table Key presents a truly incomparable canvas in one of the most sought-after destinations in the Florida Keys.

79775 Overseas Hwy, Islamorada
$4,750,000
5 Beds ⋅ 5 Baths ⋅ 615676 MLS
Experience elevated coastal living in this elegant Port Antigua retreat. Thoughtfully designed for comfort, privacy, effortless entertaining and situated in a prime waterfront location, this beautiful resort-style residence offers generous living spaces, including both upstairs and downstairs primary suites, three additional guest suites, a dedicated office, shaded porches on both levels and a spacious garage for ultimate flexibility. The gourmet kitchen flows seamlessly to a fully equipped outdoor kitchen and shaded lounge area--ideal for al fresco dining by the pool amid lush tropical landscaping. A rare combination of classic design, modern amenities, and timeless island charm. Effortless boating and space for all of your waterfront toys with 75' of deepwater dockage and quick access to both ocean and bay. Nearby homeowner's park provides the added bonuses of a private, sandy beach and boat ramp. With the serene, wide canal views and cooling bay breezes, and this is where luxury, comfort, and natural beauty, convenience converge.

88 W Plaza Del Lago, Islamorada
$2,790,000
3 Beds ⋅ 2 Baths ⋅ 617520 MLS
Beach life simplicity perfectly describes this pristine 3 bedroom, 2 bath oceanfront home with pool, covered patio, and gated for privacy. Stunning beach and ocean views are enjoyed from upper porch, lower level covered patio, living room and 2 of the 3 bedrooms. Fully remodeled in 2021, this charming get-away has been entirely refreshed with new everything...including impact windows and doors, metal roof, flooring, new appliances, central air, pool equipment and electric gate. Furnishings and finishes reflect the coastal cottage style creating the epitome of relaxation and embodying the Florida Keys lifestyle.

75055 Overseas Hwy, Islamorada
$4,700,000
4 Beds ⋅ 4 Baths ⋅ 617501 MLS
Welcome to 166 Bayview Drive, a rare bayfront estate in the prestigious Safety Harbor neighborhood of Lower Matecumbe Key. Located at Mile Marker 74, this property offers direct access to Florida Bay and the Atlantic Ocean, placing you in the heart of Islamorada's world-class boating and sportfishing scene. The home enjoys unobstructed water views and nightly sunsets that paint the sky in brilliant hues. A Tiki at the water's edge provides a perfect perch for morning coffee or evening cocktails, while mature landscaping adds privacy and tropical charm. Boaters will appreciate the deep-water dockage with davits, ideal for quick access to open water. The 2,478-square-foot residence features 4 bedrooms and 4 bathrooms, with tile flooring throughout and expansive windows that frame the bay. The open-concept living and dining areas flow into a well-appointed kitchen. The primary suite offers direct water views and private outdoor access. Outdoor living is elevated with a spacious pool and deck area, balcony, and brick paver walkways. The white picket fencing and lush landscaping complete the coastal aesthetic. Additional features include CBS construction, off-street parking, FKAA water service, septic system, and low HOA fees. Pets are welcome. Whether you're seeking a full-time residence, seasonal retreat, or investment opportunity, 166 Bayview Drive delivers unmatched location, views, and lifestyle in the Florida Keys.

166 Bayview Dr, Islamorada
$22,500,000
7 Beds ⋅ 9 Baths ⋅ 618525 MLS
Introducing Isla House. A truly exceptional waterfront estate in the heart of downtown Islamorada, which exemplifies the serene beauty and elegance of Keys living. Set on a 5.82 acre double lot, Isla House overlooks 500+ feet of pristine Florida Bay waterfront. New custom construction melds traditional Caribbean architecture with clean modern aesthetics. The over 8,800 square feet of air conditioned living space is thoughtfully designed with bright open interiors which blend sophistication and comfort while framing breathtaking views of Florida Bay. You enter a sunlit two-story foyer leading you upstairs to a bespoke great room, encapsulating a dramatic vaulted wood ceiling, spacious living area, and a custom gourmet chef's kitchen. Floor to ceiling glass doors frame an unobstructed view of the spacious bay-view terrace, which features a 50 foot elevated infinity edge swimming pool and outdoor kitchen with bar. On the upstairs level you will also find a serene primary suite, five generous en-suite guest bedrooms, a powder room, and a large laundry room. The lower level offers a separate one bed en-suite with its own entrance and patio. A media room with adjoining bathroom is the ideal flex space. A 1,600 square foot three car garage and a carport area completes the lower level. All told, there is nearly 25,000 square feet under roof cover. The estate's tropical grounds are designed to complement the home's architecture. A private floating dock offers unimpeded views of Florida Bay. Located in the heart of Islamorada, this property offers rare walkability to some of the village's most recognizable attractions. This location allows you unparalleled access to the best of Islamorada's dining, entertainment, and waterfront lifestyle. Isla House represents a rare opportunity to own one of Islamorada's most unrivaled, captivating, and serene waterfront estates—a sanctuary of elegance, craftsmanship, and timeless island charm.

81486 Overseas Hwy, Islamorada
$239,000
1 Beds ⋅ 1 Baths ⋅ 618855 MLS
Nice and quiet 1/1 located in the desirable Plantation Villas on Plantation Key. This is a upper corner unit with Tile throughout. Impact Cat 5 hurricane windows and newer AC. Tub shower combination in bath. Large walk-in closet in bedroom with lots of storage and ceiling fans throughout. Beautiful Yard area for outdoor enjoyment. This development has a pool, clubhouse and picnic area. Located near Founders Park with lots of activities and beautiful beach.

40 High Point Rd Unit 601, Islamorada
$459,000
2 Beds ⋅ 2 Baths ⋅ 618199 MLS
🌊 Spectacular Direct Ocean Views! ✨ Islamorada's Best-Kept Secret! This beautifully appointed 2-bedroom, 2-bath residence offers breathtaking, unobstructed ocean views from your private waterfront balcony. Step outside and enjoy a refreshing swim in the oceanfront pool or take a dip directly in the crystal-clear Atlantic. Perfectly situated near Bud & Mary's Marina and just minutes from Islamorada's most beloved restaurants, this location captures the very best of island living. This property is truly a must-see--and it's priced to sell. Seller will consider all reasonable offers.

79901 Overseas Highway Unit 204, 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
$8,590,000
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
$1,300,000
2 Beds ⋅ 3 Baths ⋅ 615691 MLS
Exclusive Anglers Reef Resort-style oceanfront home in Islamorada -- a rare coastal gem. Nestled inside a gated community with resort-caliber amenities, a private marina and two sandy beaches, this fully furnished two-story single-family retreat offers 2 bedrooms and 2.5 baths -- ideal for saltwater lovers or savvy investors. Thoughtfully upgraded with elegant, durable finishes: impact-rated windows and doors, brand-new stainless steel appliances, custom wood cabinetry, and gleaming granite countertops. Recently insulated with closed-cell spray foam for superior R-value, structural reinforcement, and an effective air and moisture barrier. Freshly painted in and out. Step outside to direct ocean access and easy runs to the famed Islamorada Sandbar -- perfect for boating, snorkeling, or sunset cocktails. Meticulously cared for as a private vacation haven and lightly used, the property blends turnkey luxury with strong rental potential. Weekly rentals are allowed (7-night minimum). Pet-friendly and perfectly situated for life in the Florida Keys.

104 Anglers Way, Islamorada
$6,700,000
4 Beds ⋅ 5 Baths ⋅ 616619 MLS
Iconic Islamorada Oceanfront Retreat. Welcome to The Last Resort, a one-of-a-kind oceanfront estate offering rare privacy and breathtaking natural beauty in the heart of Islamorada. Set on over an acre of lush tropical land, this coastal retreat boasts 165 feet of private sandy Atlantic beach, where you can launch a kayak or paddleboard right from your backyard and soak in endless turquoise views. Expansive covered verandahs, a 15' x 30' heated seaside pool, and beachside hammocks invite slow, sun-filled days and relaxed gatherings. Across the street, a separate canalfront parcel with a 37.5' concrete dock provides protected deep-water dockage and space for boats, trailers, and water toys — an extraordinary pairing of true beachfront living and convenient boating access. Inside, the home's 3,860 square feet is designed for easy Keys living with generous main-level living areas and bedrooms, plus a spacious upstairs suite with private bath and roof-top deck capturing panoramic ocean vistas. Four bedrooms and five baths accommodate family and guests comfortably, while breezy porches and open gathering spaces make entertaining effortless. Highlights you'll love: 165' of private sandy Atlantic beach with direct ocean entry, 37.5' private concrete dock on canalfront lot for boating convenience, 15' x 30' heated seaside swimming pool with expansive sun decks, over one acre of tropical privacy and mature landscaping, 4 bedrooms | 5 baths | 3,860 sq. ft. with thoughtful single-level layout plus upstairs suite and roof deck. A true Keys treasure, The Last Resort delivers a rare mix of sandy beach, deep-water dockage, and timeless coastal charm. Ann exceptional opportunity to create your own island legacy!

109 Columbus Dr, Islamorada
$2,495,000
3 Beds ⋅ 4 Baths ⋅ 617838 MLS
Perfectly positioned in the heart of Upper Matecumbe Key, this stunning residence places you in downtown Islamorada--just a short stroll to the area's most celebrated restaurants, art galleries, and island attractions. Privately gated and approached by a Chicago paver driveway, this absolutely turn-key 3-bedroom, 3.5-bath residence is part of an exclusive collection of just eight bayfront homes and was completed in 2020 with refined design, upscale finishes, all stainless-steel Bosch appliances, and exceptional craftsmanship throughout. Elegant interiors and thoughtful details create a sophisticated yet relaxed island lifestyle. The home features a private pool with a wood deck at the rear--ideal for entertaining or unwinding in complete privacy--while residents also enjoy access to a community bayfront pool overlooking breathtaking sunset views. An assigned boat slip on the bay provides effortless access to Florida Bay and the Atlantic beyond. Boat lift currently in place can hold boats up to 5,000Lbs. Adding to its appeal, 7-day rentals are permitted, making this property a rare and superior investment opportunity in one of Islamorada's most walkable and desirable locations. Ideal for a full-time residence, island getaway, or income-producing asset, this home offers an exceptional blend of luxury, lifestyle, and flexibility. Coral Cove is located in an X flood zone, providing additional peace of mind.

81906 Overseas Hwy Unit 2, Islamorada
$630,000
2 Beds ⋅ 2 Baths ⋅ 617971 MLS
Private location for your pleasure at this roomy townhouse offering an abundance of space to enjoy. Spiral stairs leading to the primary suites with an additional loft for your quests. Soft carpet on the living area floors with tile in the remodeled kitchen and beautiful bathrooms. Two pets allowed, with first come first serve the waterfront area. Pool and club house for your recreation along with a nice, landscaped community for your pleasure. 28-day rentals permitted. Garden setting from you extended living room to enjoy the outdoors at your back yard.

87200 N Overseas Hwy Unit N2, Islamorada
$4,600,000
5 Beds ⋅ 6 Baths ⋅ 617341 MLS
Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake creek, 70 feet of dockage, and luxurious living with 5 bedrooms and 6 bathrooms. Built with precision and modern style, this brand-new custom CBS residence boasts lush landscaping, a sparkling pool, and high-end finishes throughout. Step upstairs to find a tranquil master suite with an expansive walk-in closet, a beverage center, a large shower, and dual vanities. Three additional guest suites with private bathrooms, a spacious living area, a large laundry room, and a versatile bonus room complete the upper level, providing ample space for relaxation and recreation. On the main floor, the gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, storage pantry, Taj Mahal quartzite countertops, a wine cooler, and custom cabinetry throughout. A private guest room with an ensuite bathroom is perfect for the friends and family to visit for a staycation. The open-concept main living area flows seamlessly into the outdoors where a full bath and outdoor kitchen await. Relax by the lounge pool, enjoy synthetic grass surroundings, and take advantage of the full dock. This canal-front oasis is a rare find in the coveted Upper Keys and offers the perfect blend of luxury, comfort, and convenience. Your slice of paradise awaits!

117 Leoni Dr, Islamorada
$24,995,000
5 Beds ⋅ 8 Baths ⋅ 617705 MLS
Newly completed private oceanfront estate on 2+ acres in Plantation Key, offering an extraordinary combination of scale, privacy, dockage, and resort-style living in the heart of the Florida Keys. Designed for luxury coastal living, entertaining, and extended stays, this exceptional estate features over 9,000 sq. ft. of interior living space and more than 15,000 sq. ft. under roof. Set behind a gated entry, the residence offers 5 ensuite bedrooms, 5 full baths, 3 half baths, multiple flex spaces, an elevator, expansive covered porches, and seamless indoor-outdoor living. Additional luxury spaces include an in-home theater, private gym, and a massive office overlooking the ocean, all of which could easily serve as additional bedrooms, creating the potential for an 8-bedroom layout. The outdoor spaces are designed to showcase the Atlantic Ocean setting, with a resort-style pool, jacuzzi, generous lounging areas, and sweeping oceanfront views. Boaters will appreciate the 80-ft dock, 20,000 lb boat lift, and 160-ft jetty, creating outstanding access for enjoying the Keys lifestyle. With vacation rental zoning, the property also offers investment flexibility for those seeking personal use, income potential, or a legacy estate. Private oceanfront acreage of this scale is increasingly rare in the Upper Keys, making 87895 Old Hwy a standout opportunity for the buyer seeking a newly completed Florida Keys estate with privacy, presence, flexible living space, and exceptional waterfront amenities.

87895 Old Hwy, Islamorada
$750,000
3 Beds ⋅ 2 Baths ⋅ 613083 MLS
All NEW NEXT TO MARINA & POOL Stunning Islamorada 3 full bedrooms 2 brand new bathrooms plus oversized loft with additional queen and three twin beds. This Townhouse has ALL NEW kitchen, new bar, new built-ins, new custom fishing closet & storage, brand new 4 ton AC unit, 2 brand new Bathrooms with showers, new extended loft area, new full size Washer/Dryer, new BBQ area with new patio chicago brick pavers plus private patio shaded area with beautiful palms trees, serena & lily furniture inside, new electric panel, new electric water heater, new 80' smart OLED TV, new area just for refreshments, coffee and bar, new 4 ton AC unit, high end hurricane impact windows and doors that are reflective and cannot see inside. New Electric car charging electric panel exclusive to this unit. Best area in the community next to pool and marina with two pickleball courts and basketball court in the rear. Sleeps easily over 10 people. King bed in the master bedroom, 2 queen mattress in additional bedroom and loft along with 5 twin mattresses. Rented in winter for over $6,500 a month! Call today! This community features a new private beach, marina, dock and clubhouse. Being SOLD fully furnished and fully equipped with high end appliances (FRIGIDAIRE), high end furniture (SERENA & LILY) and furnishings. See 3 Videos: https://youtu.be/P8cOME8P_kY; https://youtu.be/b6RmPMU8pvk; https://youtube.com/shorts/BEo0F_YzVFE;

87200 Overseas Hwy Unit V9, Islamorada
$18,999,000
6 Beds ⋅ 8 Baths ⋅ 615643 MLS
A private sanctuary of coastal sophistication, The Oasis offers two residences spanning 2.85 meticulously landscaped acres with over 400 feet of pristine waterfront and a protected deepwater basin. Designed for elevated living, The Oasis blends resort-style amenities with the privacy and scale of a true Florida Keys compound. The grand porte-cochère entry sets the tone, leading to a single-level main residence with soaring ceilings, white oak floors, and 12' retractable glass walls that frame sweeping ocean views. The chef's kitchen is anchored by a Calacatta marble island, Thermador appliances, and a walk-in pantry, opening to a spacious great room and dining area ideal for entertaining. The main home features four bedrooms, six full bathrooms, and a soundproof theater room. The primary suite is a private retreat with a fireplace, dual walk-in closets, a safe room, and a spa-inspired bath with a steam shower. Each additional bedroom includes an en suite bath, private balcony, and ocean views. A detached guest house offers two additional bedrooms and bathrooms, creating a total of six bedrooms across the estate with endless space for expansion. The summer kitchen, alfresco dining areas, and multiple lounging terraces offer seamless indoor-outdoor living. The deepwater basin accommodates larger vessels and provides quick access to the Atlantic and Bay. Amenities rival a private resort: soundproof theater, fitness center with sauna, golf simulator, and two resort-style pools—each with a spa, sun deck, and outdoor entertaining spaces. Discreetly luxurious and effortlessly livable, The Oasis redefines waterfront living in the Florida Keys. Designed for ultimate security and safety, this home was built to provide unmatched peace of mind. Every element was designed with meticulous attention to detail and an uncompromising commitment to quality. The Oasis is not just a residence—it is a lifestyle statement in one of the Florida Keys' most desirable locati

87429 Old Hwy, Islamorada
$443,000
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
$6,150,000
5 Beds ⋅ 6 Baths ⋅ 618481 MLS
Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you. The elevated living level features a spacious great room with fireplace and coral accents, ideal for entertaining, along with a chef's kitchen offering custom teak cabinetry, granite countertops, island cooktop, and premium Sub-Zero and Bosch appliances. Wide screened porches extend the living space and capture open waterfront views. The home offers 5 bedrooms and 5.5 baths, a resort-style pool, and excellent updates including a new dock, new boat lift, and new A/C systems. A privacy wall enhances the secluded feel of this quiet, one-street neighborhood known for its consistently lovely homes. An exceptional opportunity for refined island living with outstanding boating access.

137 Sapodilla Dr, Islamorada
$7,400,000
5 Beds ⋅ 6 Baths ⋅ 616417 MLS
Experience Islamorada living at its absolute finest with this remodeled oceanfront estate. Situated on 200 feet of sandy waterfront with unobstructed views of the Atlantic Ocean and Alligator Reef Lighthouse, this ground-level residence is designed for resort-style living. Inside, the home features 5 spacious ensuite bedrooms and 5.5 baths, highlighted by a luxurious primary suite with a coffee bar, spa-like bathroom, and walk in closet. The spacious kitchen with double islands opens seamlessly to the main living and dining area, where the panoramic ocean views create the ultimate backdrop. An entertainment room with a wet bar, game tables, and lounge seating is perfect for hosting, while the expansive Florida room—complete with its own AC and walls of windows—brings the outdoors in. The outdoor amenities are nothing short of spectacular - including a new concrete pool (2023) with a spacious paver deck, sandy beach, tropical landscaping, and a private pier with dockage. The detached three-bay garage offers abundant storage, including one 40' bay - perfect for the boat or RV. Zoned for weekly vacation rentals, this rare property offers the opportunity for short-term rental income in a highly desirable Islamorada location. This is the one you've been waiting for - paradise found.

80201 Overseas Hwy, Islamorada
$5,999,999
5 Beds ⋅ 6 Baths ⋅ 618158 MLS
Brand new 2026 coastal luxury in Islamorada's White Marlin Beach. 181 Nautilus Dr offers the ultimate Keys lifestyle with 5 bedrooms, 5.5 baths, and 5,320 SF of living area across three levels. Served by a private elevator that opens on all floors. Designed for indoor/outdoor living, enjoy a resort-style pool and a modern outdoor setting ideal for entertaining. Built for peace of mind with impact glass doors and windows and a concrete flat roof, the home features a state-of-the-art chef's kitchen and elevated finishes throughout. Boaters will love approximately 70' of concrete dockage on a straight seawall plus a 15,000-lb boat lift (remote-controlled). Enjoy quick bay access and ocean access via the Channel 5 Bridge, known for its high-clearance fixed span (approx. 65' vertical clearance) (buyer to verify vessel requirements and navigation). The White Marlin Beach community is also known for a gated private sandy neighborhood beach with amenities, an exceptional Islamorada bonus.

181 Nautilus Dr, Islamorada
$1,590,000
4 Beds ⋅ 3 Baths ⋅ 615226 MLS
Stunning new custom pool home in the heart of Islamorada. This exceptional, brand-new ground-level home was thoughtfully designed and expertly crafted with meticulous attention to detail. A professional interior designer curated high-end fixtures and elegant finishes throughout, creating a polished and inviting living space. Offering a rare 4-bedroom, 3-bathroom split floorplan, the home features a spacious open-concept layout ideal for both everyday living and entertaining. Soaring 10-foot vaulted ceilings and oversized 8-foot doors define the home's modern architectural style. Additional highlights include a two-car garage, swimming pool, low-maintenance turf, and quality construction that sets a new standard for homes in the area. Located in desirable downtown Islamorada, you're close to popular restaurants, shopping, a grocery store, and a beloved brewery. With new construction permits currently suspended in Islamorada, opportunities like this are becoming increasingly rare. Don't miss your chance to own one of the last newly built homes in this prime location - this property truly checks all the boxes.

36 Park Rd, 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
$550,000
2 Beds ⋅ 3 Baths ⋅ 618784 MLS
Set in the very center of Islamorada's vibrant island community, this 2BD/2.5BA townhouse style condo in Sand Pebbles offers privacy, comfort, and convenience. The ground level features two spacious en-suite bedrooms, each with its own private porch. Upstairs, enjoy a bright open-concept living, dining, and kitchen area plus a convenient half bath. With 1,303 sq ft and multiple outdoor living spaces including an outdoor spiral staircase feature, this home lives large. Sand Pebbles is a well maintained bayfront community offering a heated pool, tiki hut, garden areas, onsite trailer storage, and a bayfront observation deck. Walk or bike to marinas, dining, and shopping to enjoy the best of Islamorada living.

80450 Overseas Hwy Unit APT 106, Islamorada
$475,000
2 Beds ⋅ 2 Baths ⋅ 616492 MLS
Condo for Sale - Islamorada, Plantation by The Sea 2 Bedrooms | 1.5 Bathrooms | Furnished | Two-Story Townhouse Style Experience the unique lifestyle of the Florida Keys in this spectacular furnished condo at Plantation by The Sea! Located in prestigious and convenient Islamorada, this exclusive two-story townhouse-style condo is the perfect retreat for those seeking comfort and authentic coastal living. Fully furnished and equipped - just bring your suitcase and get ready to enjoy! Key Features: 2 spacious bedrooms 1.5 bathrooms Kitchen with modern appliances and functional cabinetry Community Amenities: Heated ocean-view pool Fitness center with modern equipment and sauna Community room with billiards, ping-pong, and board games Extra-long fishing pier Community BBQ area (Boats and jet skis are not permitted) Asking Price: $475,000 Rental Option: $2,700 per month Showings: By appointment only - No sign on property. Call now to schedule your private showing!

87465 Old Hwy Unit 218, Islamorada
$3,950,000
4 Beds ⋅ 5 Baths ⋅ 618400 MLS
The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 14, Islamorada