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$3,875,000
4 Beds ⋅ 3 Baths ⋅ 620412 MLS
Coastal elegance meets the ultimate boating lifestyle in this beautifully updated Venetian Shores home. Designed for effortless Keys living, the open floor plan is filled with natural light, highlighted by a dramatic floor-to-ceiling wall of windows in the living area that brings the outdoors in. An inviting entrance foyer welcomes you inside, with interior stairs to the main living level. The spacious kitchen is the heart of the home, featuring stainless steel appliances, a large island for gathering, and a separate laundry room and pantry for added convenience. The main living level offers two guest bedrooms and two full baths, including one bedroom with a private en-suite bath. Direct access from the second-floor living area to the pool deck creates a seamless connection between indoor and outdoor living. The open floor plan offers plenty of room for dining, watching TV, conversation and even some ping pong. Upstairs, the expansive primary suite provides a peaceful retreat with a walk-in closet and luxurious en-suite bath. A fourth bedroom on the third floor offers flexibility for guests, family, or a home office. Separate air-conditioning systems for each floor ensure year-round comfort. Outside, 70 feet of dockage and a 27,000-pound boat lift make this property a dream for boating enthusiasts, with quick access to both the Atlantic Ocean and Florida Bay. The resort-style backyard is ready for endless summer fun, featuring a sparkling pool, expansive sun deck, shady lounging area, and abundant storage for all your fishing, diving, and water sports gear. Whether you're entertaining friends, heading out for a day on the water, or simply relaxing poolside, this exceptional Venetian Shores home offers the perfect blend of coastal sophistication and waterfront adventure.

109 Giardino Dr, 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
$599,000
2 Beds ⋅ 2 Baths ⋅ 620393 MLS
Welcome to coastal living in the heart of Islamorada! This beautifully appointed townhouse in the desirable Executive Bay Club offers comfort and resort-style amenities. The main level features an open-concept floor plan with a spacious living area and kitchen, plus full bath, creating an inviting space for entertaining and everyday living. Upstairs, you'll find an expansive primary suite, a generously sized guest bedroom and full bathroom, and a thoughtfully finished loft accessed from the hallway that serves as an ideal bonus sleeping area or home office. Step outside and enjoy the exceptional amenities that make Executive Bay Club one of Islamorada's most sought-after waterfront communities. Residents have access to the newly expanded first-come, first-serve dockage, a bayfront beach area, unforgettable sunsets, and a new heated swimming pool complete with an updated pool deck, clubhouse and bath facilities, pickleball and tennis courts, kayak storage and 24/7 staffed gated entry. Whether you're searching for a full-time residence, vacation retreat, or investment opportunity, this welcoming townhouse offers the ideal blend of island charm to enjoy the Florida Keys lifestyle.

87200 Overseas Hwy Unit D3, Islamorada
$1,495,000
3 Beds ⋅ 3 Baths ⋅ 620353 MLS
Experience the ultimate Keys lifestyle in this beautifully furnished and impeccably maintained waterfront pool home in desirable Lower Matecumbe Key. Offering 60 feet of newly decked dockage along the tranquil ''Sleepy Lagoon'', this exceptional property combines relaxed island living with effortless boating access to both the ocean and bay. The light-filled second floor features an open-concept living, dining, and kitchen area with soaring cathedral ceilings and new vinyl flooring throughout. The recently remodeled kitchen showcases new cabinetry, stainless steel appliances, and an inviting layout ideal for entertaining. Two bright bedrooms with laminate flooring are located on this level, including a spacious primary with en-suite bath. Step outside onto the expansive second-floor balcony and enjoy breathtaking lagoon views while watching manatees glide by and fish jump in the tranquil waters below. The first floor offers additional flexible living space with an open bedroom/living area and full bath, featuring sliding glass doors that lead directly to the tropical backyard, pool, and dock. Designed for comfort and convenience, this fully turnkey home includes well-maintained accordion shutters on all non-impact windows, generous storage space for water toys and gardening equipment, and a securely anchored storage shed. Outdoor living is truly exceptional. Relax beneath the airy chickee hut, cool off in the in-ground pool after a day on the water, or entertain family and friends with freshly grilled BBQ favorites in the private backyard oasis. Additional features include a JetDock, fish cleaning station, spacious outdoor shower, fenced backyard for pets, and ample parking for boats, trailers, RVs, and recreational equipment. Residents may enjoy access to a beautiful sandy beach within the subdivision through a voluntary HOA membership. The beach is a protected turtle nesting habitat.

140 Iroquois Dr, Islamorada
$1,890,000
5 Beds ⋅ 3 Baths ⋅ 620271 MLS
Experience the ultimate Florida Keys lifestyle in this stunning split-level waterfront loft and take advantage of the vacation rental revenue. Ideally located in highly sought-after Lower Matecumbe. This exceptional 5-bedroom, 3-bath residence combines contemporary design with breathtaking water views, creating a truly unique island retreat. The thoughtfully designed layout features three spacious bedrooms on the lower level and two additional bedrooms upstairs, connected by a spectacular modern staircase that serves as a striking architectural centerpiece. Soaring ceilings and expansive windows fill the home with natural light, while the open-concept floor plan seamlessly connects the living, dining, and entertaining spaces. The sleek, modern kitchen is perfectly positioned to serve both everyday living and waterfront gatherings. Generously sized bedrooms and beautifully appointed bathrooms provide comfort and privacy for family and guests alike. Step outside to an impressive 667-square-foot waterfront screened deck overlooking the tranquil lagoon, offering the perfect setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. Boaters will appreciate the deep-water dockage featuring a large boat slip and 16k boat lift, with convenient access to both the Atlantic Ocean and Florida Bay. Enjoy stunning views of the bayside lagoon and the ocean, along with world-class fishing, diving, and boating right from your backyard. Additional amenities include covered parking and ample storage space for all your water toys. Offering the perfect blend of modern elegance, waterfront living, and premier boating access, this remarkable Lower Matecumbe property is a rare opportunity to own a piece of paradise in one of Islamorada's most desirable locations. Onsite property management for true peace of mind.

74980 Overseas Highway Unit 3, Islamorada
$609,900
2 Beds ⋅ 2 Baths ⋅ 620243 MLS
Experience the ultimate Florida Keys lifestyle in this bright and spacious townhouse-style condo located in sought-after Executive Bay Club in Islamorada. Ideally situated next to Founders Park, this gated bayfront community offers an unbeatable combination of location, lifestyle, and investment potential. One of the standout features of this residence is the rare open kitchen layout, creating a more spacious and inviting main living area ideal for everyday living or entertaining. EBC is highly desirable for boaters and investors alike, with first-come, first-served dockage available for boats, immediate bay access, and quick ocean access via Snake Creek and Tavernier Creek. Residents and guests enjoy a private sandy beach with beautiful sunset views, plus community amenities that include a renovated pool and clubhouse, tennis courts, pickleball courts, BBQ area, kayak launch, kayak storage, trailer parking, and secure gated entry. Short-term rentals are allowed with a 28-day minimum, making this an excellent opportunity for full-time living, a vacation getaway, or an income-producing property. Located in the heart of Islamorada and within walking distance to Founders Park events, recreation, and nearby dining, this property offers the ideal blend of waterfront enjoyment, boating convenience, and rental flexibility in one of the Florida Keys' most desirable communities.

87200 Overseas Hwy Unit APT A 7, Islamorada
$1,595,000
620208 MLS
DIRECT OCEANFRONT LOT IN ISLAMORADA WITH ACTIVE BUILDING PERMIT! A rare opportunity to own a beautifully situated direct oceanfront parcel in the heart of Islamorada, offering breathtaking panoramic views of the Atlantic Ocean. An active building permit is already in place, allowing you to begin construction of your dream waterfront estate immediately, or take advantage of the Village of Islamorada's available two-year permit extension. This spacious homesite includes a mangrove height reduction permit, allowing the mangroves to be trimmed to six feet. Upon completion, the property will enjoy unobstructed ocean views at ground level, creating an exceptional setting for luxury coastal living. Enjoy direct ocean access with convenient nearby Florida Bay access via Snake Creek, as well as close proximity to dry-dock marina facilities. Potential exists for an observation deck and/or dock, further enhancing the property's appeal and maximizing the spectacular waterfront setting. The elevation rendering is conceptual and provided for illustrative purposes. Utilize the approved plans currently in place or modify them to create a custom residence tailored to your vision. Opportunities like this are increasingly rare--build your dream home and experience the unparalleled beauty, boating, fishing, and island lifestyle that make the Florida Keys so desirable.

229 Coral Rd, Islamorada
$6,150,000
6 Beds ⋅ 7 Baths ⋅ 620190 MLS
Welcome to 194 Buttonwood Lane, a rare waterfront sanctuary nestled in the prestigious Safety Harbor enclave. This meticulously designed 6-bedroom, 7-bathroom residence seamlessly blends architectural elegance with modern comfort. The heart of the home features a chef's kitchen outfitted with top-of-the-line appliances, custom cabinetry, and breath taking stone finishes on the countertops and backsplash. A thoughtfully placed custom steam shower adds a spa-like element to the home's exceptional amenities. This home is perfect for everyday living and elevated entertaining. Expansive living spaces flow effortlessly to the outdoors, where covered lounge areas, low-maintenance artificial turf, and tropical landscaping create the ultimate indoor-outdoor lifestyle. A full laundry room and spacious garage add practicality to the property's thoughtful design. Boating enthusiasts will appreciate 100 feet of prime dockage plus an additional 20 feet of canal frontage, offering unmatched access and flexibility for multiple watercraft. Not included in the listed square footage is a 488 SF garage and over a thousand square feet of covered patio. This home is perfect for the indoor/outdoor entertainer. A true statement of coastal luxury—this is Florida Keys living at its finest.

194 Buttonwood Ln, Islamorada
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 620148 MLS
Futura Yacht Club Rare 3 Bed/2 Bath Condo with 39 ft. Deeded Boat Slip AND 24,000 lb. Boat Lift in desirable Futura Yacht Club! Located in the heart of Plantation Key in Islamorada, this is 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 Hwy Unit 101 & Boat Slip 22, Islamorada
$2,695,000
5 Beds ⋅ 3 Baths ⋅ 620127 MLS
Welcome to one of Islamorada's finest homes! Located in Venetian Shores the premier boating community of Islamorada. One of only two streets in the neighborhood with curbs and street drainage system. 70ft of deep water dockage and 100ft wide canal. Direct Ocean and Bay access via Snake Creek. Draw bridge to ocean for yachts and tower boats. This home is a must see! Extremely clean and well maintained home. Fantastic layout. Upstairs you have a little over 1,900 sq ft of living space all on one floor - which includes your kitchen, living room, dining room, 3 large bedrooms and 2 bathrooms. Downstairs you have your rec room with 2 bedrooms, cabana bath and tackle room/workshop. Solid concrete construction designed to offer peace of mind during hurricane season. Conveniently located close to restaurants, shopping, Publix, schools, and hospital.

113 Villa Bella Dr, Islamorada
$450,000
1 Beds ⋅ 1 Baths ⋅ 620105 MLS
ISLAMORADA RETREAT! Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this charming home is perfectly situated in the heart of Islamorada. Offering 1 bedroom, 1 bathroom, and a versatile loft space, the interior provides comfortable living with a relaxed Florida Keys atmosphere. Step outside to the open porch, the perfect spot to enjoy the island breeze. Ideally located near renowned waterfront dining, local breweries, boutique shopping, and all the attractions that make Islamorada one of the most desirable destinations in the Keys. Residents benefit from a recently completed sewer system upgrade, with no known upcoming assessments. Low monthly HOA fees of just $149 cover common area and road maintenance. Don't miss this opportunity to own your own slice of paradise in the Sport Fishing Capital of the World and experience the laid-back lifestyle that makes the Florida Keys so special.

84961 Old Hwy Unit 41, 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
$899,000
1 Beds ⋅ 1 Baths ⋅ 620039 MLS
Memories begin here. Tucked along the ocean's edge and offering the kind of lifestyle buyers spend years searching for, this one-of-a-kind oceanfront retreat delivers the ultimate Florida Keys escape all for under $1M! What is unique about this property is the 40' protected boat slip located right out your back door. This unit is conveniently located offering quick access to the ocean or the bay and the Islamorada sandbar is within view. The elevated tiki with panoramic ocean vistas that make every sunrise, lunch, happy hour, and sunset unforgettable. Inside, the cottage is light, coastal, and move-in ready with an inviting open layout that keeps the focus where it belongs--on the view and the lifestyle. Whether you're looking for a weekend getaway, fish camp, vacation retreat, or memory-making waterfront hideaway, opportunities like this are incredibly rare. Bring the boat. Bring the family. Start making memories.

84961 Old Hwy Unit LOT 27, Islamorada
$1,385,000
3 Beds ⋅ 2 Baths ⋅ 620016 MLS
Ocean Harbour condo with Atlantic ocean views and a boat slip in Islamorada. 3 bedroom, 2 bathroom luxury condo offers expansive ocean views and comfortable living space. The thoughtfully redesigned floor plan enhances the primary suite layout, adds a third bedroom, updates both bathrooms, and expands the living area by enclosing the porch as additional interior living space; maximizing functionality, comfort, and guest accommodations. Features updated appliances, hurricane impact glass, boat slip #33 and one covered parking space. Elevated waterfront living within this premier gated community featuring beach areas, oceanfront clubhouse, swimming pool, spa, gym, pickleball and tennis courts, EV charging station, boat ramp, and boat trailer storage. The beach tiki is ideal for entertaining with a grill, ice maker, and TV. Pets allowed with restrictions. Enjoy boating, fishing, kayaking, paddle boarding, nearby restaurants, medical care, boutique shopping, and art galleries. Bring your boat and experience the best of Florida Keys waterfront living.

87851 Old Hwy Unit M42, Islamorada
$369,000
2 Beds ⋅ 2 Baths ⋅ 620020 MLS
Located in Plantation by the Sea, this Islamorada townhouse offers 2 bedrooms, 1.5 bathrooms, covered parking, and a storage unit in a gated oceanfront complex. Inside, the unit has been updated with renovated kitchen, bathrooms, and flooring. Both upstairs bedrooms feature open balconies, along with an additional balcony off the living room for added outdoor space. The upstairs layout includes 2 bedrooms and 1 full bathroom, while the half bath is conveniently located downstairs. Community amenities include a covered parking space, plenty of guest parking, storage unit, workout room, sauna, kayak and paddleboard storage, bicycle storage, clubhouse, and gated entry. Conveniently located near Founders Park, Islamorada's community park offering a beach, Olympic-size swimming pool, tennis courts, pickleball courts, ball fields, and an amphitheater.

87455 Old Hwy Unit 244, Islamorada
$2,375,000
4 Beds ⋅ 4 Baths ⋅ 620004 MLS
Welcome to your own private slice of Islamorada paradise! This canal-front home offers easy access to Florida Bay along with stunning lake views and unforgettable sunsets. This home features CBS construction, a metal roof, accordion shutters, living areas above base flood elevation, and plenty of parking. The upstairs main living area offers over 2,000 square feet of living space with 3 bedrooms and 2.5 bathrooms. Vaulted ceilings and an open, spacious layout are designed to capture natural light and water views. The large kitchen flows seamlessly into the living and dining areas, making it ideal for entertaining or simply enjoying the relaxed Keys lifestyle. The bedrooms are located down the hallway, creating a nice separation from the main living spaces. The primary suite features a walk-in closet and a beautifully appointed spa-like bathroom with marble finishes, dual vanities, granite countertops, soaking tub, and a glass-enclosed steam shower with multiple shower heads. All bedrooms are generously sized with ample closet space. The downstairs living space offers over 770 square feet and is separate from the upstairs, creating a great private area for guests to enjoy, complete with sliding glass doors that open directly to the pool area. Outside, enjoy lush tropical landscaping, a canal-front pool with heater, 60' of dockage with a 15,000 lb boat lift, and quick boating access to Florida Bay. The outdoor living space is ideal for entertaining with plenty of room under the carport along with an outdoor kitchen. Whether you are heading out for a sunset cruise, fishing trip, or waterfront dining, this location puts the best of the Florida Keys lifestyle right at your fingertips.

316 Woods Ave, Islamorada
$2,900,000
2 Beds ⋅ 2 Baths ⋅ 619931 MLS
What does everyone want? The smallest house in a great neighborhood! THIS IS THE ONE! Tucked away in the sought-after Venetian Shores neighborhood of Islamorada, this solid CBS waterfront home is perfectly positioned for enjoying the effortless boating lifestyle the Keys are known for. With 100 feet of dockage, a 15,000 lb. boat lift, and a fish cleaning station, this home is just one lot from Snake Creek which offers immediate access to both the Atlantic Ocean and Florida Bay. Enjoy peaceful Snake Creek views and the constant reminder that the water is always just moments away. Upstairs, the open floor plan is designed to capture natural light and Snake Creek views, with vaulted ceilings creating an airy coastal feel throughout the living, dining, and kitchen areas that span the width of the home. Three sets of sliding glass doors invite the outdoors in, opening the space to breezes and waterfront scenery. Two bedrooms and one full bath complete the upper level, while downstairs offers valuable storage space, a permitted full bath, and covered carport parking. The cleared lot provides exceptional flexibility with ample room for boats on trailers, additional vehicles, or the opportunity to expand the existing home and create an even larger waterfront retreat. Don't miss out on this exceptional value!

154 Milano Dr, Islamorada
$3,199,000
3 Beds ⋅ 2 Baths ⋅ 619869 MLS
Beautifully renovated oceanfront home in Islamorada offering 100 feet of direct ocean frontage, a sandy beach, breathtaking open water views, and mature tropical landscaping. This exceptional concrete stilt home has undergone a spectacular extensive coastal renovation, blending modern luxury with the relaxed elegance of the Florida Keys lifestyle. The residence features 3 bedrooms and 3 bathrooms with a bright, open-concept floor plan designed to maximize natural light and panoramic ocean views. The upstairs living quarters include a stunning new chef's kitchen with custom cabinetry, premium countertops, and high-end appliances, along with beautifully renovated bathrooms and spacious living and dining areas that flow seamlessly onto the elevated oceanfront porch. Recent upgrades include a brand new roof, all new impact windows and doors, renovated bathrooms, a fully redesigned kitchen, updated finishes throughout, and extensive coastal improvements designed for both style and durability. The gated and fenced property also features a gorgeous oceanfront swimming pool with updated pool equipment, outdoor shower, covered parking for multiple vehicles and boats, and abundant storage space. Outdoor enthusiasts will appreciate the impressive 90-foot oceanfront fishing pier with concrete pilings and low-maintenance composite decking, creating the perfect setting to fish, relax, entertain, or take in the spectacular sunrise views over the Atlantic Ocean. This is a rare opportunity to own a fully renovated luxury oceanfront retreat in Islamorada, known as the ''Fishing Capital of the World.''

75071 Overseas Hwy, Islamorada
$1,199,000
3 Beds ⋅ 3 Baths ⋅ 619848 MLS
Experience all that Islamorada has to offer from this stunning home that was constructed in 2020. This two-story residence offers 3 spacious bedrooms and 2 full bathrooms on the ground floor. The second floor has a large great room - ideal for a home office, second living room, playroom, or media space--adding extra versatility to the layout. Additionally, there is another full bathroom upstairs. Step into an open-concept main living area with numerous windows to let in the natural light. Easy to clean tile throughout. The heart of the home is a modern kitchen featuring a large island, custom cabinetry, and premium finishes--perfect for entertaining and everyday living. The spacious side and backyard provide ample space for trailers, boats, or a future pool, making it perfect for outdoor enthusiasts. Speaking of pool, there is a current, valid pool permit that has been issued for the property and can be transferred to the next owner. This home is located just minutes from the ocean, marinas, shopping, and dining. It is zoned for highly rated Coral Shores High School. This home offers the rare opportunity to own an almost new, move-in-ready property in the Upper Keys. Don't wait--schedule your private showing today and make this modern island retreat your forever home!

143 N Hammock Rd, 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
$13,250,000
7 Beds ⋅ 7 Baths ⋅ 619776 MLS
LUXURY BEACHFRONT ESTATE HOME! Come embrace this brand-new magnificent property where you will encounter a relaxing ambiance gracefully set on over 2 private acres of pristine bayfront offering deep-water dockage with a 20,000 lb boat lift, a white sandy beach and stunning unobstructed panoramic views of the Florida Bay located in desirable Lower Matecumbe. Spanning nearly 6,000 square feet of extraordinary living space with 7 bedrooms and 7 bathrooms. Thoughtfully designed for ultimate comfort, this estate features two separate guest wings, each offering three private bedroom suites, ideal for family, guests or an unparalleled private retreat. The gourmet chef's kitchen, perfect for entertaining, leads to an expansive and inviting great room, elegant tray ceilings, designer finishes, and sophisticated architectural details throughout. A private elevator offers effortless access between levels. Step outside to your own tropical sanctuary, where a stunning pool deck overlooks the sparkling waters of Florida Bay. Lush tropical landscaping provides privacy, while spacious covered terraces provide the perfect backdrop for unforgettable sunsets and year-round outdoor living. With weekly rentals permitted with a Vacation Rental license, this rare offering combines luxurious personal enjoyment with outstanding investment potential. Experience the Florida Keys lifestyle in one of Lower Matecumbe's most exclusive waterfront settings. SELLER FINANCING AN OPTION WITH 50% DOWN.

75840 Overseas Hwy, 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
$595,000
2 Beds ⋅ 2 Baths ⋅ 619711 MLS
Welcome to Sand Pebbles -- Islamorada's Hidden Gem. Located in the heart of the Village of Islamorada, this spacious 2-bedroom, 2-bathroom condo at the boutique community of Sand Pebbles offers the quintessential Florida Keys lifestyle you've been dreaming of. With only 16 units, Sand Pebbles delivers an intimate, low-key atmosphere that larger communities simply can't match, your own private slice of island paradise. Step inside and discover a bright, airy layout designed for both relaxed living and effortless entertaining. The open-concept floor plan flows naturally, with two generously sized bedrooms and two full baths offering the perfect retreat after a day on the water. Community amenities that elevate everyday life: heated resort-style pool, tiki hut, garden areas, a bayfront observation pier, and on-site trailer storage. Boaters will enjoy easy access to the nearby Safe Harbor Angler House Marina for all of their boating needs. Located just moments from world-class sportfishing, diving, dining, and the eclectic local shops that make Islamorada truly special, Sand Pebbles places you at the center of it all while maintaining the peaceful, uncrowded feel.

80450 Overseas Highway Unit 204, 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
$1,149,000
619655 MLS
Waterfront commercial investment opportunity with 100 feet of dockage on a 13,500 sq ft lot, offering both canal frontage and open ocean views--an increasingly scarce combination in the Upper Keys. Ideally located just outside Port Antigua and White Marlin Beach, the property benefits from strong visibility and proximity to established boating and residential communities. The site features convenient eastbound ingress and egress, supporting efficient operations and customer access. Zoned Commercial Fishing, it allows for a diverse range of income-producing uses, including charter services, boat rentals, marine repair, seafood distribution, restaurant or other waterfront commercial ventures. With direct water access, substantial dockage, and flexible zoning, this parcel is well-positioned for long-term appreciation and immediate revenue potential in a supply-constrained coastal market.

74520 Overseas Hwy, Islamorada
$749,999
2 Beds ⋅ 2 Baths ⋅ 619594 MLS
Fully furnished turn key townhome in Islamorada at Las Maravillas is available, one of only 10 private residences on the bayside on Lower Matecumbe in the Village. Dockage, covered parking, trailer storage, beautiful pool, gated and fenced grounds highway to bay right on Lower Matecumbe Bight. 2 bedrooms with Jack and Jill bathroom on the top floor could be converted to two bathrooms. Half bath, kitchen, dining and living area on main level. Storage room and drive thru parking underneath suitable for medium size boat on trailer or two cars. Tropical vegetation and fruit trees and nice landscaping. Kitchen and baths are modern. updated stainless appliances. Carpet and tile throughout. This is the opportunity to get into the keys at a modest price and enjoys the keys life. Owner occupied so notice is appreciated. Easy to show. Call ahead for appointment.

75710 Overseas Highway Unit 1, Islamorada
$8,000,000
3 Beds ⋅ 3 Baths ⋅ 619592 MLS
Discover your dream retreat in this beautiful oceanfront home, set on 1.5 acres of prime beachfront property with 150 feet of pristine white sandy beach, this is the ultimate getaway for relaxation and adventure. Unwind in the oversized heated pool or customized hot tub after a day of sun and fun. The Tiki Hut provides convenient storage for all your water toys, making your boating and beach days effortless. Enjoy practicing your swing on the private putting golf course, all while surrounded by breathtaking ocean scenery. With a lucrative 7-day rental option and an easily obtainable license, this gem is perfect for both personal enjoyment and investment. Don't miss your chance to own this slice of paradise--schedule a viewing today!

88747 Old Hwy, Islamorada
$2,195,000
3 Beds ⋅ 4 Baths ⋅ 619577 MLS
Welcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare blend of privacy, prestige, and resort-style living awaits in this Key West-inspired residence, set within one of Islamorada's most exclusive gated bayfront communities. Surrounded by manicured tropical landscaping and timeless architectural charm, this home offers an elevated island lifestyle defined by serenity and sophistication. A palm-lined entrance leads to a vibrant exterior with wraparound porches and sun-filled interiors framed by lush garden views. The spacious three-bedroom layout is designed for effortless indoor-outdoor living, with multiple gathering spaces opening to expansive patios ideal for entertaining, unwinding, or savoring golden sunsets. Mature palms, bougainvillea, and the scent of salt air create a secluded sanctuary that feels worlds away. Residents enjoy exclusive access to a resort-style pool, private beach, kayak launch, and a breathtaking sunset point reserved for owners. A protected marina provides direct access to world-class sport fishing and boating, while full-time on-site property management ensures peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the home offers effortless proximity to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. Whether you're seeking a seasonal escape or a long-term legacy investment, this property delivers enduring value wrapped in unmatched natural beauty. Experience the rare combination of luxury, leisure, and privacy that makes the Legacy Retreat truly exceptional.

33 Pen Ky, Islamorada
$1,650,000
5 Beds ⋅ 3 Baths ⋅ 619545 MLS
Experience Coastal Luxury and privacy with this exceptional 5 bedroom, 3 bath home on two lots!! Over 2900 sq. ft. of thoughtfully designed living space. Constructed of concrete with impact windows and doors and recently painted inside and out, this home blends style, safety, and comfort. The property's coastal architectural charm is highlighted by a beautiful wrap-around porch and a curved pavered driveway leading to the air-conditioned garage. the main floor includes three bedrooms and 2 baths, featuring a master suite at the end of the home with private access to the backyard and heated pool. Upstairs two large bedrooms share a Jack-and-Jill bath, ideal for family or guests. The chef's kitchen boasts stainless steel appliances, an eat-in area, and a full walk-in pantry, flowing seamlessly into the sun-room and open living/dining area with a canal view. The outdoor living spaces are designed for entertaining and relaxation, including a heated pool with Jacuzzi, torch-lit ambiance around the pool, a fire pit and beautifully landscaped grounds. An air-conditioned shed - currently used as a potting shed - can easily serve as a playroom, art studio, or man cave. Boating enthusiasts will love the boat storage with in-and-out service less than 5 minutes away, offering reduced maintenance and added protection. Convenient access nearby to boat ramps at Founders Park, which also offers a sandy beach, pool, dog park, and sports field. Many community events held here - and you can just walk over to them. This home is set in a private, desirable neighborhood near upscale dining and amenities. Luxury, versatility, and lifestyle in one perfect package. Please schedule your private showing today to experience 169 Venetian Way!!

169 Venetian Way, Islamorada