Strattons (82.5) Real Estate, Homes, Condos for Sale in Islamorada, FL

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

$315,000

620621 MLS

50' X 22' boat slip at the World famous Lor E Lei marina. Excellent in-town location, you know you're going to boat over here anyway so you might as well tie up for the night! Enjoy the sunsets, unwind, Uber home, or use for your fishing business, so many possibilities. A rare find.

96 Madeira Rd Unit # 10, Islamorada

$735,000

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

$6,999,000

8 Beds ⋅ 6 Baths ⋅ 619673 MLS

Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available. Experience luxury coastal living at its finest in this exceptional Gated bayfront estate, ideally situated in the heart of Islamorada. Set on a rare peninsula with over 225 feet of prime waterfront, this property offers unmatched privacy, panoramic views, and direct access to both the Florida Bay and Atlantic Ocean. The main residence features 7 spacious bedrooms and 5 beautifully appointed bathrooms designed with both elegance and comfort in mind--perfect for entertaining or hosting large gatherings. A dramatic third-floor Birds Nest Sky Lounge features 360-degree glass walls and a walkout rooftop deck, capturing breathtaking vistas in every direction. Expansive living areas and thoughtfully designed spaces capture stunning water views from every angle. A Whole House Generator for peace of mind. A private 1-bedroom, 1-bathroom guesthouse provides the ideal retreat for visitors, accommodating extended family, or potential rental income or creating a secluded retreat. For boating enthusiasts, the estate includes an impressive 85+ foot deep-water yacht slip and four boat lifts, offering seamless access to both the Bay and Ocean--an unparalleled fishing advantage in the Florida Keys. Step outside to your own waterfront oasis, where a gorgeous heated bayfront pool invites relaxation while you take in breathtaking sunset views and the tranquil surroundings. Blending luxury, comfort, and premier waterfront access, this remarkable estate presents a rare mixed-use opportunity in one of Islamorada's most coveted locations. Seller will consider all reasonable offers.

1101 Mastic St, 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

$24,995,000

7 Beds ⋅ 11 Baths ⋅ 619281 MLS

Experience unparalleled oceanfront living at the Chateau on the Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal living reflects the sophistication of what has been referred to as the Hamptons of Miami. From the moment you arrive, a striking sense of privacy, scale, and intention is evident, with architecture and surroundings that feel truly unforgettable. Completely reimagined and newly constructed in 2023, this residence showcases exceptional modern design, engineering, and craftsmanship. Set on just under 2 acres of pristine coastline, the property offers 19,784 SF of total living and entertaining space, including 10,182 SF under air. Inside, soaring ceilings and walls of glass create a seamless indoor-outdoor connection, filling the interiors with natural light and highlighting refined, couture-level finishes. Amenities include a fitness center, indoor basketball and pickleball court, a Baccarat-inspired grand ballroom, and a custom Glamour Suite. Outdoors, a mosaic pool and spa overlook the Atlantic Ocean, complemented by alfresco dining, a firepit lounge, and multiple terraces with sweeping coastal views. A 300 inch outdoor LED theater and rooftop terrace elevate the experience. A 100ft private dock provides direct ocean access. Approved plans include 6 additional suites, including 2 oceanfront residences, allowing expansion into a multi-structure compound. A rare legacy estate defined by privacy, scale, and presence

82719 Old Hwy, Islamorada

$2,900,000

4 Beds ⋅ 5 Baths ⋅ 604613 MLS

NEWEST DEVELOPMENT IN DOWNTOWN ISLAMORADA!! Come preview finished units NOW. Only ONE HOUSE LEFT. An exclusive, gated enclave on the Atlantic Ocean, Oceanside is nestled between the Cheeca Lodge and the Caribbean Resort, offering the very best of location, privacy and island living. Low maintenance concrete block construction, this home has been built above flood level. Spacious living area of more than 2,500 square feet, with fully collapsing Euro doors both on the second floor, leading out to a covered balcony, and on the first floor, opening to the private pool and deck, Oceanside House 6 boasts four bedrooms with ensuite baths, plus a first floor powder room. Large open kitchen, island and living area flow seamlessly. The property also allows vacation rentals. This beauty will not last! Make an appointment to visit the site today. Owner is Florida licensed real estate agent.

105 Carroll St Unit 6, Islamorada

$4,900,000

618920 MLS

Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom - ideal for a comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A permit has been submitted to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. With the existing estate slated for demolition and redevelopment, the conceptual renderings unveil a spectacular 4,872-square-foot custom residence offering five bedrooms, five and a half bathrooms, a three-car garage, and a resort style pool - all thoughtfully designed to capture water views from every vantage point. This remarkable bayfront estate offers endless possibilities in an unparalleled setting.

150 List St, Islamorada

$4,900,000

1 Beds ⋅ 1 Baths ⋅ 618918 MLS

Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom - ideal as a weekend escape, guest retreat, or comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A permit has been submitted to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. Surrounded by multimillion-dollar estate home sales, this offering represents a rare chance to secure a premier bayfront parcel in one of Islamorada's most sought-after locations. With the existing estate slated for demolition and redevelopment, the conceptual renderings unveil a spectacular 4,872-square-foot custom residence offering five bedrooms, five and a half bathrooms, a three-car garage, and a resort style pool - all thoughtfully designed to capture water views from every vantage point. This vision blends refined indoor living with outdoor elegance, creating a seamless waterfront sanctuary. Whether you envision a private coastal retreat or an entertainer's paradise, this remarkable bayfront estate offers endless possibilities in an unparalleled setting.

150 List St, Islamorada

$4,400,000

2 Baths ⋅ 617385 MLS

Exceptional Islamorada commercial investment opportunity. Established national retailer, West Marine, occupies the property under a long-term lease with renewal options, delivering a consistent and reliable 6.08% cap rate. The 9,990 SF building, constructed in 2018, is situated on a 30,000 SF parcel with US-1 frontage in the heart of downtown Islamorada. Site features include 32 on-site parking spaces, Village Center zoning, and excellent highway visibility. This is a rare opportunity to acquire a stable, income producing investment property in one of the most constrained commercial markets in the Florida Keys.

81984 Overseas Hwy, Islamorada

$18,000,000

2 Baths ⋅ 613627 MLS

''The Pulse of Islamorada'' ... Iconic Islamorada Restaurant & Cabana Bar available for Sale, Real Estate and Business included. Spanning over 1,000 feet of bayfront and 500 ft of Highway frontage, where the locals & visitors come from near & far to watch nightly sunsets over the bay, enjoy food & libations, and listen to live bands daily. This property includes over 5 acres of real estate (survey available), full service bar with 5 Cop liquor license, 250 seat outdoor restaurant, private party & tournament hosting area. New parking lot, lighting, & drainage completed in 2020 with plenty of parking to expand the business. Concrete building built in 2015/2016 for gift shop, bathrooms, laundry, prep kitchen, storage, and more. In addition, property includes main kitchen, special event tiki bar, dockage, beach, boat ramp, and more. Sale includes 4 on site building rights & 2 boat slips in the Islamorada Yacht Basin located adjacent to property. Room for expansion. Voted Best Sunset year after year. Additional information and financials available upon request. NDA and POF required. Contact Listing Agent . All information to be verified by Buyer/Buyer's Agent.

96 Madeira Rd, Islamorada

$840,000

1 Beds ⋅ 1 Baths ⋅ 612052 MLS

Exquisite Oceanfront at 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. This MAIN LODGE OCEANFRONT condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful King Bedded Oceanview Room. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa, workout facility, and multiple pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted tennis courts and a fitness center. 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 shopping. 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 208, Islamorada

$1,000,000

4 Beds ⋅ 3 Baths ⋅ 613295 MLS

Your Slice of Paradise Awaits in 'Downtown' Islamorada Discover the perfect blend of modern coastal living and convenience with this beautifully remodeled ground-level duplex in the heart of Islamorada. Located just a moment from the famous Cheeca Lodge and the vibrant Arts District, you'll be surrounded by charming shops, restaurants, and galleries. Property Highlights: • Two Separate Units PLUS a Guest Space: Each of the two dwellings is thoughtfully designed with a bright, airy ambiance to complement the island lifestyle. Use one unit for yourself and rent out the other, and/or welcome family and friends to visit! • Durable Construction: Built with concrete and topped with a sturdy metal roof, this home is designed to withstand the elements. Impact windows and doors provide added protection and energy efficiency. • Private Outdoor Oasis: The fully fenced yard features an electric gate, artificial turf for low maintenance, and lush landscaping with vibrant tropical foliage, perfect for relaxing or entertaining. Why You'll Love It: Whether you're looking for a permanent home or a vacation retreat, this property delivers the ideal Florida Keys lifestyle. The Village of Islamorada recognizes two dwelling units, adding significant value to the property. Don't miss your chance to own this coastal gem in an unbeatable location! Buyers should be able to convert this building in to one single-family home and transfer one of the building rights to another Village non-waterfront lot that is deemed appropriate by the Village. Two units are recognized by the Village. Buyers must confirm all with Village of Islamorada.

107 Carroll St, Islamorada

$5,400,000

3 Beds ⋅ 3 Baths ⋅ 617408 MLS

Islamorada Bayfront Estate with Dockage & Open Bay Views... all in downtown Islamorada within walking distance of your favorite spots! Custom built in 2014, this concrete fortress is storm-resilient and also offers a host of sustainability features including a whole-house solar array. Situated on a peninsula with 250+ feet of crystal-clear open waterfront, the gated estate provides unparalleled privacy. This open water home has no neighbors looking through side yards and of course, no neighbors across a canal. Designed to offer the ultimate combination of location, deep-water dockage, storm resiliency and open water views, this luxurious home also boasts marble floors throughout and a gorgeous ''floating'' staircase. Begin your day by stepping out of your bedroom to your private bayfront terrace and into a stunning second floor Infinity Edge pool, complete with a heater/chiller. In the evening, experience the brilliance of Islamorada's sunsets from every room, the rooftop or outdoor lanais, which provide a grand total of almost 6,000 sf of combined indoor and outdoor living space. Floor-to-ceiling sliding glass doors disappear into pockets, bringing the indoors out and the outdoors in. Just one step outside the main kitchen is a full outdoor kitchen and bayside dining, al fresco. For stargazing, venture up to the rooftop deck for a breathtaking front row seat. Ready to get on the water? Your boats will comfortably berth on the 100' deep water dock with two lifts and are kept safe by built-in storm protection. Other functional luxuries include an elevator, an enormous three-car 2,200 sf garage with workshop/storage, camera/security system and mature landscaping with fruit trees. A fourth bedroom with bath can be easily added without modifying the structure at a reasonable cost. With all living space above flood and built to withstand sustained 200 mph winds, this concrete home has accordion shutters over impact for ultimate storm resiliency.

100 List St, Islamorada

$710,000

1 Beds ⋅ 1 Baths ⋅ 607224 MLS

Exquisite and historic Cheeca Lodge is located in the heart of Islamorada, the fishing capital of the world. Embrace an island lifestyle in luxury through resort ownership. With a 96% occupancy rate, condotel ownership allows 28 days of luxury island living and instant passive income stream. Stay, play, and earn is the combination that makes this tropical paradise an ideal investment. Lush vegetation frames the pool and tennis court view for unit #722, giving a tree-house feel. With 550 sq ft of spacious living, this luxury hideaway is a true home away from home. Embrace refined living in this suite, hosting a separate living area, kitchen and bathroom. The airy living room, with pull-out couch and extra seating, is made even more spacious with the charming balcony designed for alfresco dining. Dream island-style in the king size bedroom and delight in the full-size soaking bathtub. The private dressing area is the final touch to this enlightened space. The full kitchen boasts a refrigerator, range, microwave, and dishwasher - making quick work for preparing easy in-room fare. Revel in the comfort of the time honored resort offering 5-star dining, 2 tiki bars, full-service spa, 3 pools, ocean front beach, 550-ft pier, par-3 nine-hole golf course, 6 lighted tennis courts, fitness center, water sports and lush gardens throughout. Embrace the island lifestyle at the Cheeca Lodge and Spa.

81801 Overseas Highway Unit 722, Islamorada

$505,000

1 Beds ⋅ 1 Baths ⋅ 608764 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 top floor 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 631, Islamorada

$1,250,000

3 Beds ⋅ 3 Baths ⋅ 617148 MLS

Newly Remodeled 3-Bed, 3-Bath Home in the Heart of Islamorada This newly remodeled 3-bedroom, 3-bath home is located on Upper Matecumbe in the heart of Islamorada, offering the perfect blend of modern comfort and island living. The unique layout features 1 bedroom and 1 bathroom downstairs, and 2 bedrooms and 2 bathrooms upstairs--ideal for guests or extended family. Built with solid concrete construction and impact windows, this home is elevated above flood and designed for peace of mind. Inside, enjoy an open-concept living area perfect for entertaining, a spacious kitchen with stainless steel appliances and granite countertops, and bright, generously sized bedrooms. Modern finishes and high-quality craftsmanship shine throughout. Step outside to a large deck perfect for soaking up the Florida Keys sunshine. Located on a quiet street with beach access at the end of the road, this property offers convenience and tranquility. Close to world-class restaurants, shops, and some of the best fishing and diving in the world. Excellent rental potential--buy one or both adjoining homes for added opportunity. 'The adjacent residence offers a rare opportunity to expand into a multi-residence estate or income-producing property.' 'The neighboring home may be acquired to create an exceptional multi-home setting ideal for extended family living or rental income.' 'Purchasing the nearby residence allows for a flexible use property, suitable for private family living or investment purposes.' 'The adjoining property presents a unique opportunity to establish a private multi-home arrangement or enhance rental potential.' 'With the option to acquire the neighboring home, buyers can create a distinctive residential setting with income potential. Home currently leased for 1 yr.

191 Carroll St, 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

$7,500,000

8 Beds ⋅ 6 Baths ⋅ 606334 MLS

Experience the unparalleled appeal of FairWinds, nestled in the heart of coveted downtown Islamorada. This exceptional oceanfront estate is a distinctive and idyllic beachside compound, seamlessly blending casual elegance with the convenience of desirable amenities. Pass through the entrance gate, meander the Chicago brick drive, and enjoy the captivating, lush tropical gardens, complete with native and tropical specimens, as well as a variety of fruit trees that guide your way toward the serene pastel blues of the Atlantic Ocean. A private sandy beach awaits — a secluded haven for cherished moments with friends and family. Privacy and recreation harmoniously coexist in the remarkable four bedroom, three and one-half bath grand Caribbean inspired main house, which features wrap-around porches and wide verandas, complete with awe-inspiring ocean vistas. Savor breathtaking sunrises and the historic Alligator Reef Lighthouse, with the occasional sea turtle nesting on your beach, as well as schools of bonefish and tarpon on the flats just of offshore. This property features a guesthouse with three bedrooms, two baths and split floor plan. In addition, there is a detached three-bay carriage house with private captain's or staff quarters on top. A spacious four-car garage beneath the main house ensures ample room for both land and sea adventure. Discover your slice of a Caribbean paradise right at home, within walking distance to excellent restaurants, resorts, spas, and charming shops that exemplify the essence of allure, Islamorada-style. Embrace simplistic beauty, barefoot elegance, and boundless possibilities that await at FairWinds.

207 & 209 E Carroll St, Islamorada

$775,000

2 Beds ⋅ 2 Baths ⋅ 618074 MLS

Ground-level living in the heart of Islamorada! Situated on an oversized parcel, this beautifully completely remodeled 2-bedroom, 2-bath home offers comfort and an unbeatable location. This FULLY FURNISHED tastefully updated interior includes porcelain tile throughout the home including showers, quartz countertops and brand new LG appliances and offers an open living area and flows seamlessly to a large screened porch--perfect for relaxing or entertaining while overlooking the expansive backyard and enjoy the attached spacious storage room. Weekly Rentals Allowed once the property meets the required assessed value. Zoned Village Center (VC), the property provides exceptional potential with a wide range of mixed-use and commercial options, making it ideal as a primary residence, investment, or live/work opportunity. Enjoy a superior central location with walking distance to neighborhood beach access, local breweries, shopping, and some of Islamorada's best dining. A rare opportunity to own a versatile property in one of the Keys' most desirable areas.

82207 Old Hwy, Islamorada

$850,000

3 Beds ⋅ 3 Baths ⋅ 605662 MLS

Serene Oasis in the heart of Islamorada.: This secluded spacious, lushly landscaped property is within walking distance to nearby restaurants, boutiques, and most of Islamorada's charms. This poured concrete, 3 bedroom 3 bathroom, 2,314 sqft house sits on a lovely, 13,983 sqft lot offering ample parking and room for expansion or a pool. Upstairs boasts a wide open floor plan providing light aplenty, with a wide open floor plan and access to two decks from the living room area and the master bedroom. All double sliders upstairs have accordion shutters . Downstairs adds a large, legal, non conforming studio apartment with a full bath and two storage rooms. Property includes a limited easement to the Fl Bay that does not include boating rights. Bring your personal touches and make this hidden gem your splendid Keys get-a-way.

82260 Overseas Hwy, Islamorada

$710,000

1 Beds ⋅ 1 Baths ⋅ 609862 MLS

***Seller Financing now an option! ***Own a piece of the legendary Cheeca Lodge Resort and Spa. Located in Islamorada, the ''Sportfishing Capital of the World''. Condo Features -This spacious King Bed Suite offers a large living room area with a pull-out queen bed, a grand bathroom with walk-in shower and soaking tub, a fully equipped kitchenette, and a private screened in porch with views of the lush landscape and large coconut palms. This exceptional income-producing property allows nightly rentals. Owners use 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! The Resort -Enjoy 27 acres of Islamorada oceanfront that include 3 world class restaurants, 2 open-air tiki bars, 1,200' of private beach, 525' fishing pier, 2 family pools, 1 adults only pool, beach and pool side cabanas, 9 hole golf course designed by Jack Nicklaus, 6 sports courts, 15,000 sqft of event space, valet parking, 24 hour shuttle service, concierge service, on site boat trailer parking, watersports activities, fitness center and Camp Cheeca.

81801 Overseas Highway Unit 712, Islamorada

$675,000

1 Beds ⋅ 1 Baths ⋅ 613885 MLS

Cheeca Lodge Resort and Spa—the very name conjures up images of swaying palms, salt-kissed air, a rich history, and the promise of an idyllic escape. Where the Sun Kisses the Sea and Dreams Come to Life. Historic Charm, Modern Luxury: Cheeca Lodge—a time capsule where history whispers. Turnkey suites, nightly rentals, and savvy investment. Feast Fit for Poseidon: Five-star dining, tiki bars, and ocean-view room service. Bon appétit! Beachfront Bliss: 1,200-foot sandy beach, palm-lined. Cabanas for sun-kissed souls. Sport & Serenity: Fishing pier, pools, sport courts. Yoga by sunrise, gardens for strolls. Beyond the Horizon: Explore Islamorada's heartbeat—restaurants, clubs, galleries. Your Key Awaits: Unlock your private condotel at the one and only Cheeca Lodge. Dip your toes, sip your cocktail, and let the waves serenade you. Ready to write your island tale? Call it home, call it heaven—just call it yours.

81801 Overseas Highway Unit 612, Islamorada

$880,000

3 Beds ⋅ 3 Baths ⋅ 615716 MLS

This renovated treehouse retreat is your picture-perfect getaway or forever island home! Discover a rare opportunity to own a beautifully reimagined Keys haven in the heart of Islamorada. Nestled among lush tropical foliage on an expansive 15,000+ sq ft lot, this fully renovated CBS residence offers a seamless blend of coastal comfort and timeless Old Florida charm. 3 spacious bedrooms, 3 full baths, and a versatile lower-level flex space, the home is designed for both tranquil living and effortless entertaining. Impact doors and windows throughout ensures peace of mind while thoughtful upgrades elevate comfort and style. Enjoy quiet mornings on the deck or explore the nearby serene waters from your shared day dock with easement to access the Bay—perfect for kayaking, paddleboarding, or swimming. (Please note: boating rights are not included.) Tucked away in a secluded yet central location, this private sanctuary offers the ultimate in island living—where nature, easygoing elegance, and serenity converge.

82260 Overseas Hwy, Islamorada

$585,000

1 Beds ⋅ 1 Baths ⋅ 610464 MLS

Location and possibilities abound in this prime downtown Islamorada cozy home. Walking distance to the Lorelei, Mangrove Mikes and all the shops, restaurants, breweries and galleries that Islamorada has to offer. This opportunity at this price point just doesn't happen very often. Call for showing because this one wont last long.

153 List St, Islamorada

$6,500,000

611386 MLS

Once in a lifetime investment in the heart of Islamorada. This exceptional property offers a wide range of potential uses as it includes two Village Center parcels stretching from Highway to Bay, currently featuring a spacious 3,995 sqft restaurant and bar with a coveted 5COP liquor license - no food quota. Village Center zoning allows for multiple use opportunities including, but not limited to, single family estate, multi family compound, luxury townhomes, vacation rentals, restaurants, marinas, general store with package sales, and much more. The property spans 30,415 sqft. Includes a Bayfront boat basin, and plans for an additional 100' dock to be constructed. The Village of Islamorada officially recognizes three waterfront market-rate dwelling units . The three waterfront Transferable Development Rights (TDRs) can be utilized onsite, transferred to another location, or sold to a receiver site. The Village Center Zoning would allow up to 8 market-rate dwelling units to be developed on site for a new luxury townhome community, with the transfer in of additional TDRs. Whether you're looking to rehab a local iconic business, start a new business, redevelop the entire site, or create a spectacular residential estate, this unicorn property is perfectly located. ***Buyer to verify ALL information.***

81910 & 81908 Overseas Hwy, Islamorada

$8,300,000

6 Beds ⋅ 7 Baths ⋅ 610851 MLS

This exquisite bayfront Islamorada property features a main home with four bedrooms, four full bathrooms, and two half bathrooms, along with a guest house offering two bedrooms and one bathroom. The kitchen features marble countertops, a gas range, and counter seating. With a separate dining area and 30 ft high ceilings in the great room, floor-to-ceiling windows offer breathtaking views of the bay waters and dynamic sunset skies. The infinity edge pool with a spa offers reflections of beautiful palms and exquisite landscaping. The outdoor cabana kitchen is perfect for al fresco dining, and the boat basin with dockage allows for easy access to the waters of Florida Bay. A whole-house generator ensures uninterrupted comfort and tiki torches light the backyard terraces. Don't miss the waterfalls cascading into the boat basin, creating a truly serene retreat.

82238 Overseas Hwy, Islamorada

$750,711

2 Beds ⋅ 2 Baths ⋅ 615703 MLS

Bright and airy Keys home in the Heart of Islamorada! Old Highway location popular with walkers, runners, and cyclists. You're just a short stroll from 'downtown' Islamorada's best restaurants, shops, and galleries. Step inside to soaring tongue-and-groove ceilings that create an open, airy vibe, complemented by warm wood flooring and abundant natural light throughout. The spacious living and kitchen area flows seamlessly to a wide covered porch overlooking the private side yard—perfect for morning coffee or evening cocktails. Well-designed with impact windows and doors, a metal roof, 2025 AC and a practical layout that includes a laundry room, garage, and a cozy loft space ideal for storage or bonus use. With its unbeatable location, breezy coastal vibe, and thoughtful details, this home is ideal for full-time living, weekend escapes, or investment potential in the Florida Keys.

81975 Old Hwy, Islamorada

$1,250,000

3 Beds ⋅ 3 Baths ⋅ 617147 MLS

Newly Remodeled 3-Bed, 3-Bath Home in the Heart of Islamorada This beautifully remodeled 3-bedroom, 3-bath home is located on Upper Matecumbe in the heart of Islamorada, offering the perfect combination of luxury, comfort, and island style--all on one level. The open-concept floor plan features a spacious living area ideal for entertaining, a modern kitchen with stainless steel appliances and granite countertops, and three generous bedrooms each with its own bathroom. Built with solid concrete construction, impact windows, and elevated above flood, this home provides durability and peace of mind. Enjoy modern finishes throughout and a large outdoor deck perfect for relaxing or hosting gatherings. Situated on a quiet street with beach access at the end of the road, this home offers both convenience and tranquility. Close to world-class dining, shopping, and some of the best fishing and diving in the Florida Keys. Excellent rental potential--buy one or both adjoining homes for added investment opportunity. 'The adjacent residence offers a rare opportunity to expand into a multi-residence estate or income-producing property.' 'The neighboring home may be acquired to create an exceptional multi-home setting ideal for extended family living or rental income.' 'Purchasing the nearby residence allows for a flexible use property, suitable for private family living or investment purposes.' 'The adjoining property presents a unique opportunity to establish a private multi-home arrangement or enhance rental potential.' 'With the option to acquire the neighboring home, buyers can create a distinctive residential setting with income potential.' Rental Available longterm $6,000 per month

189 Carroll St, Islamorada

$610,000

2 Beds ⋅ 2 Baths ⋅ 616006 MLS

Exceptional Opportunity in the Heart of Islamorada! Located in the desirable Village Center (VC) zoning district, this fixer-upper home offers endless possibilities for redevelopment. Whether you're looking to renovate for residential use or take advantage of the flexible zoning that allows for a variety of commercial and mixed-use options—including retail, office, and much more (with Village approval}—this property is a rare find. Situated just off US1, you'll enjoy excellent visibility and accessibility in one of Islamorada's most dynamic areas. Bring your vision and transform this property into something special!

82207 Old Hwy, Islamorada

$1,800,000

4 Baths ⋅ 616246 MLS

Prime Commercial Opportunity in Islamorada! A rare find in the heart of Islamorada. This iconic restaurant property offers exceptional visibility along the world-famous Overseas Highway. Perfectly positioned on the corner of Overseas Highway and Blackwood Drive, this site has excellent traffic exposure, strong curb appeal, and convenient access for both locals and visitors traveling through the Florida Keys. Close proximity to multiple resorts, shopping, and the Morada Way Art District. The building totals 4,942 square feet situated on a 16,746 square feet lot, with ample customer and employee parking available in the front, side, and rear of the property with a 160 seat restaurant and a 5COP liquor license. Zoned Village Center (VC), the site offers tremendous flexibility for a wide range of commercial uses and is located in desirable X flood zone. Currently home to the Islamorada Shrimp Shack, a local staple and internationally recognized restaurant featured on Food Network's ''Diners, Drive-Ins, and Dives'' with Guy Fieri, the property presents a truly unique opportunity. Whether you're looking to continue a restaurant tradition in a turnkey setting or redevelop into a new commercial concept, this property provides a strong foundation for growth.

81901 Overseas Hwy, Islamorada

$735,000

1 Beds ⋅ 1 Baths ⋅ 607112 MLS

For statistical purposes only.

81801 Overseas Highway Unit 612, Islamorada

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