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$649,000
1 Beds ⋅ 1 Baths ⋅ 620677 MLS
Crystal-clear turquoise waters, swaying palms, and gentle ocean breezes create the perfect Florida Keys escape. The historic Cheeca Lodge is located in the heart of Islamorada, which is recognized as ''The Sport Fishing Capital of the World''. Islamorada is renowned for fine dining, water sports, The Art District, galleries, shopping and breweries. The resort encompasses 27 acres with 1,200' of beach frontage and a 525' fishing pier. This beautiful one-bedroom King suite, with additional sleeper sofa in the living room and private screened balcony, overlooks the garden and waterfall. This is a luxury, income-producing property. Nightly rentals are allowed, with onsite management, an owner's closet, and owner's use of up to 28 days. The resort offers a 24-hour shuttle, valet parking, concierge service, 5-star fine dining, ballroom, conference room, a spa, fitness center, beach, pools, dock, tiki bars, 9-hole par 3 golf course, Pickle Ball courts, lighted tennis courts, lush gardens, bike path, fishing, diving, snorkeling, water sports and Camp Cheeca for children.

81801 Old Hwy Unit 754, Islamorada
$549,500
1 Beds ⋅ 1 Baths ⋅ 620633 MLS
Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This king bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

81801 Overseas Highway Unit 715, Islamorada
$549,500
1 Beds ⋅ 1 Baths ⋅ 620629 MLS
Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This double queen bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

81801 Overseas Highway Unit 716, Islamorada
$3,100,000
5 Beds ⋅ 3 Baths ⋅ 620602 MLS
Newly remodeled waterfront home located in the highly desirable Port Antigua subdivision of Lower Matecumbe. This expansive residence offers five bedrooms and three bathrooms with an open living floor plan. The main living level features three bedrooms and two bathrooms, complemented by a spacious living, dining, and kitchen area--ideal for entertaining and relaxed Keys living. The lower level includes two additional bedrooms and one bathroom, all above flood, perfect guest quarters with a full kitchen. Brand new exterior paint! Enjoy 75 feet of deep-water concrete dockage equipped with a 15,000 lb boat lift, providing excellent boating access. The home is solid concrete construction with a metal roof, fenced yard, and plenty of room for a pool. Port Antigua is known for its exceptional amenities, including one of the best private beaches in the Keys and a community boat ramp. With immediate access to Florida Bay and quick proximity to the Atlantic Ocean, this property offers the ultimate Florida Keys lifestyle--boating, water access, and island living at its finest.

117 El Capitan Dr, Islamorada
$619,995
2 Beds ⋅ 2 Baths ⋅ 620555 MLS
Welcome to Futura Yacht Club! Your island getaway awaits in this highly desirable Plantation Key community. Unit 304 is a 2 bed, 2 bath, beautifully maintained condo. Florida Bay views make this third floor perch heavenly. A hideaway murphy bed is an additional feature adding to the desirability of this coastal condo as an ideal second home or rental. Owners and renters benefit from extensive community amenities, including a boat ramp, on-site boat and trailer storage, a large pool with adjacent club area, kayak storage, paddleball and basketball courts, and well-maintained grounds with shaded picnic spots. The on-site management team maintains the serenity of this community. This immaculate condo is being sold fully furnished. Futura is the place to be for boating, with short run times to the Ocean and Florida Bay. Easy boating and spectacular Florida Bay sunsets make for a beautiful investment in island living.

88540 Overseas Hwy Unit APT 304, 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
$13,900,000
6 Beds ⋅ 9 Baths ⋅ 620077 MLS
Yes, you can have it all! This one-of-a-kind 3.2 acre Islamorada bayfront estate offers a new boat dock, more than 250 feet of sandy wade-in bayfront shoreline, two full residences, a separate garage/media house and a move-in ready package of extras unlike any other property in the Keys. This remarkable compound captures the spirit of the Keys with a level of scale and exclusivity seldom found on the islands. Arrive through a private gate to discover a secluded retreat where every detail has been curated for relaxed coastal living. For boaters, the new boat dock offers immediate access to Florida Bay and immediate Atlantic Ocean access through nearby Snake Creek. The welcome package also includes a newer 34' Edgewater with twin 400 hp Yahamas, a pair of Waverunners and UTV tow vehicle, plus fishing rods, kayaks, paddle boards, and bicycles to enjoy everything Islamorada has to offer. The 100 ft. long resort-style pool with large spa create the centerpiece of the property, surrounded by multiple lounging areas, outdoor kitchen with covered bar, shady terraces and intimate gathering spaces. The estate's flexible layout includes two full homes--a 2/2.5 with ground level living, and a 3/3.5 tri-level--plus a 1/1.5 media house with 2-car garage, all with classic island character. Both homes offer chef kitchens with high-end appliances including SubZero and La Cornue. Not only is this estate ready for fun, it's also ready to enjoy with furniture, decor, kitchenware and even linens included! This remarkable property encompasses 2 acres of upland, 1.2 acres of baybottom, a separate buildable lot, plus valuable development rights. It is also conveniently located next to Islamorada's crown jewel Founder's Park for near instant access to seasonal festivals, sports fields, dog park, playground, tennis and pickleball courts and much more. All of these features elevate the property into a true legacy holding--ideal as a luxury residence, family compound, or private retreat.

139 Gimpy Gulch Dr, Islamorada
$715,000
1 Beds ⋅ 1 Baths ⋅ 619786 MLS
Welcome to your island King suite overlooking the beautiful lagoon at the historic Cheeca Lodge & Spa. Income producing property allowing 28 fabulous owner days! Cheeca handles all vacation rentals making your investment hassle free. The resort offers a spa, Camp Cheeca for the kids, beachfront pool, 9-hole par 3 golf course, lush gardens, bike path, tennis courts, fitness center, 5 star dining, tiki bar, beach, dock, water sports, and fishing. Sleeper sofa in living area for additional sleeping. Monthly condo insurance is $854 in addition to the monthly association fee.

81801 Overseas Highway Unit 637, Islamorada
$4,750,000
4 Beds ⋅ 5 Baths ⋅ 619714 MLS
Double Lot! Unparalleled Waterfront Command in Port Antigua. Boasting one of the largest water frontages in Islamorada's exclusive Port Antigua, this striking 3 story residence offers 4 bedrooms, 4.5 baths, and an extraordinary 220 feet of dockage with dual boat lifts. Every bedroom is beautifully appointed across thoughtfully designed living levels. Step outside to your private marina, where turnkey boating infrastructure meets the crystalline waters of the Florida Keys. Port Antigua residents enjoy exclusive access to a private beach and boat ramp amenities known only to a select few. Where unmatched dockage and island luxury converge in one of Islamorada's most coveted addresses.

44 W Plaza Del Lago, Islamorada
$699,000
1 Beds ⋅ 1 Baths ⋅ 619668 MLS
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare opportunity to own a premier, income-producing property in the heart of Islamorada. This beautifully appointed one king-bedded room with kitchen, private screened in balcony, with owners closet, offers the ideal blend of personal retreat and investment potential. Set within one of the Florida Keys' most celebrated resorts, owners and guests enjoy a true luxury experience, featuring exceptional dining, new ballroom, two tiki bars, a full-service spa, fitness center, and multiple resort-style pools, 9 hole, Par 3 golf course, The property boasts direct beach and dock access, along with lighted tennis courts, pickleball courts and a wide array of water sports, all surrounded by lush tropical landscaping. Nightly rentals are permitted, creating strong income potential, while professional onsite management provides seamless maintenance and guest services. Ideally located just moments from Islamorada's renowned restaurants, galleries, breweries, shopping, and vibrant art district, this is a unique chance to own within one of the Keys' most historic and sought-after destinations.

81801 Overseas Hwy Unit # 729, Islamorada
$585,000
1 Beds ⋅ 1 Baths ⋅ 619365 MLS
Attention Investors! Own a piece of the legendary Cheeca Lodge Resort and Spa. Located in Islamorada, the ''Sportfishing Capital of the World''. This spacious Two Queen bed Suite offers a spacious beautiful bathroom featuring a walk-in shower and soaking tub, a private screened in porch with views of the lush landscaping and large swaying palm trees. This exceptional income-producing property allows nightly rentals. Owners enjoy occupancy of their units up to 28 days a year and receive a monthly check for the remainder of the time. It's a hands-off income generator! Enjoy the 27 acres of Islamorada oceanfront that includes 3 world class restaurants, 2 open-air tiki bars, 1,200' of private beach, 525' fishing pier, 2 family pools, 1 adults only pool by the spa, beautiful sandy beach and pool side cabanas, 9 hole golf course, 6 sports courts, 15,000 sq. ft of event space, valet parking, 24 hour shuttle service, concierge service, on site boat trailer parking, watersports activities, fitness center and Camp Cheeca, for the children's entertainment, when only the best will do!

81801 Overseas Highway Unit 727, Islamorada
$4,445,000
8 Beds ⋅ 4 Baths ⋅ 619083 MLS
Venetian Shores, the premier waterfront community in Islamorada!!! Looking for that larger than life home, well this is it! We have an 8 bedroom, 4 baths a pool, with nearly 5,000 sq. ft. of living area. Quick access to the Atlantic Ocean and Florida Bay with in minutes via Snake Creek. What makes this location unique is the 100 foot wide, deep water canals and what make this property more unique and valuable than others, we offer 100 linear feet of dockage. There is a 30,000 pound lift for your large boats and a 10,000 lift for your smaller boats. And there is still room for another vessel or personal water crafts. This home offers three levels, the main level has three bedrooms a full bath a kitchenette and living area with great views of the water. The second level, large living area with soaring ceilings, a massive kitchen, 2 bedrooms and a full bath. The third level offers 3 bedrooms and 2 full baths. There is an abundant pool and bar area for entertaining family and friends. Looking for a home to accommodate the large extended family, this is it or put it out in the Airbnb world, it would make a great income property.

136 San Remo Dr, Islamorada
$14,990,000
6 Beds ⋅ 9 Baths ⋅ 618911 MLS
Newly completed in 2025, this exceptional oceanfront estate is located in the heart of The Florida Keys on the premier ocean side of Islamorada. A gated entry welcomes you through lush tropical landscaping and a diverse fruit-tree grove, setting a private and refined arrival. Set on over 2 usable acres with 210 feet of private sandy beachfront and a protected cove, the residence spans 7,590 square feet of interior living space & 1,736 square feet of exterior living, with an expansive 230-foot dock. Designed for seamless indoor-outdoor living, the home features a dramatic great room with 23-foot ceilings, panoramic Atlantic exposure, and expansive covered terraces with summer kitchen and outdoor dining areas. A 65-foot heated lagoon-style pool with swim-up bar and fire-pit lounge creates a resort-caliber setting. The chef's kitchen is appointed with Sub-Zero, Wolf, and Thermador appliances. Additional highlights include dual primary suites, private orchid garden, lounge & recreation room, elevator, Sonos surround sound, impact windows and doors, metal roof, double-height garage, water-sports storage room and a full home generator. The essence of beachfront living in Islamorada, combining impressive scale and ultimate privacy. ***A contiguous 0.7-acre lot with development rights for an ancillary building with upstairs storage is available separately.

88351 Old Hwy, 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
$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
$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