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$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
$1,890,000
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
$3,999,999
2 Beds ⋅ 2 Baths ⋅ B26001957 MLS
Estate Opportunity - Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, and generous waterfront dockage--all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. The 2/2 pool home is updated and ready for refined living.

77340 Overseas Highway, Islamorada
$3,349,000
3 Baths ⋅ R11164709 MLS
74560 Overseas Highway is a dynamic waterfront commercial asset with multiple revenue paths and significant redevelopment potential. Situated on a 15,000 SF parcel with generous on-site parking and 100 feet of seawall capable of accommodating up to 8 slips, the property delivers premier highway exposure and immediate Florida Bay and Atlantic Ocean access. Zoning supports four affordable housing units, one market-rate residence and 5,640 SF of commercial space, creating a layered income strategy that blends residential density with marine-oriented business activity. Commercial fishing zoning allows for uses such as a restaurant, seafood market, marine outfitter, charter or fishing headquarters, or other enterprises aligned with the working waterfront.

74560 Overseas Highway, Islamorada
$710,000
1 Beds ⋅ 1 Baths ⋅ B26036550 MLS
Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Great vacation and income producing condotel in the Sport Fishing Capital of the World. This 27-acre oceanfront Islamorada resort set in a lush tropical landscape has everything from fine dining restaurants, spa and wellness, fitness center, three resort style pools, two tiki bars, par 3 golf course, four lighted tennis courts, pickleball, basketball, bicycles, huge pier for fishing, kayaking, paddleboarding, and more. This top floor corner unit is a beautifully appointed one king bedroom with expansive master bath, kitchen and private screened in balcony. Accomplished on-site professional management has delivered high occupancy and rental rates far above many other lodging properties in the Keys!

81801 Overseas Highway Highway Unit #714, Islamorada
$14,166
B26010836 MLS
10,000 SF open warehouse-style space available in the heart of Islamorada. The space features expansive interior floor area, two offices, modern multi-stall bathrooms. Five oversized loading doors provide substantial clearance, easy access and excellent natural light. The flexible layout lends itself to a variety of uses including: • Specialty vehicle or collector car storage • Artist studio or creative workspace • Marine equipment storage and outfitting • E-commerce fulfillment • Contractor headquarters with indoor material storage • Fitness or training facility (subject to approval) • Film, photography, or production space Centrally located with convenient US-1 access and ample maneuverability, this property offers immediate occupancy with strong long-term potential. Offered as a sublease through August 31, 2027, with the opportunity to negotiate a direct lease thereafter.

210 Industrial Drive, Islamorada
$1,150,000
2 Beds ⋅ F10546467 MLS ⋅ Anglers Reef BLDG.
ANGLERS REEF HOME THAT PAYS FOR ITSELF! Islamorada's Upscale Oceanfront Gated Community that allows Vacation Rentals, This home features 2 bedrooms, 2.5 bathrooms with carport & 4 porches. Upgrades include Brazilian Cherry hardwood floors, kitchen with granite countertops and SS appliances with 2 breakfast bars & tons of cabinet space. The home also has a composite decking, metal roof & impact doors & windows. The community features 2 sandy beaches, a pool & marina on the Atlantic Ocean. Home has been in rental program for many years with a good following. Own your vacation home for free & more. Great investment. Call today for a showing!

102 Anglers Way, Islamorada
$1,300,000
2 Beds ⋅ 2 Baths ⋅ B26016320 MLS
A New Standard of Paradise - Live with views of the Atlantic Ocean everyday. This home has been updated and beautified from top to bottom. Marble flooring throughout living areas. Eat in kitchen offers large island, snack counter and full size wine cooler. Dishwasher installed 12/25. There is also a hot water dispenser. Dining area and living area open to enclosed patio with private spiral staircase leading to resort styled amenities. Impact glass on all windows. Primary bedroom offers more spectacular views, built in furnishings and is 14x14. Modification in primary bathroom leads to large walk in closet. Washer replaced 2025, dryer 2024, AC 2021. Building inspections complete with no pending assessments. Private Marina dredged 2025. Outside storage cage included. RARE covered parking. Enjoy resort style pool, hot tub, tennis, pickleball, nature trails, gazebos, boat ramp, clubhouse with fitness, pavilion with ice machine, docks rentable for up to 30ft boat (almost always available), tiki huts, electric vehicle chargers, guest parking, open lot for boat storage, and private marina. Chandelier in dining area excluded. Beach area overlooks marina. Owner agent.

87851 Old Highway Unit #M5, Islamorada
$50,000
F10555238 MLS
A-1 Urgent Care & Family Practice Center - Islamorada, Florida KeysAre you a Doctor looking to purchase an established practice or know a Doctor in the Market? This Medical practice has ben established for 20 years and has steadily grown over time.Located in Islamorada, there are few other medical offices for clinics or pediatrics making this a very interesting opportunity for any interested Medical personnel.

99198 Overseas Highway, 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
$6,999,000
4 Beds ⋅ 5 Baths ⋅ A12032087 MLS ⋅ Plantation Beach BLDG.
Private Bayfront Estate in desirable Islamorada offering a serene ambiance on an oversized parcel of pristine bayfront with breathtaking sunsets and unobstructed panoramic views of the Florida Bay. This exceptional waterfront retreat features an irreplaceable protected boat basin, concrete jetty, and T-dock providing superior deep-water dockage. Encompassing 4,000 square feet of beautifully designed living space, this remarkable residence includes 4 spacious bedrooms and 4.5 bathrooms. This home showcases an inviting kitchen and multiple expansive living areas all thoughtfully designed for ultimate comfort and entertaining, ideal for hosting family and guests or enjoying a private coastal escape. Step outside to your own tropical sanctuary with unforgettable sunsets, year-round outdoor living, and the sparkling waters of Florida Bay creating the ultimate Florida Keys lifestyle. A rare opportunity to own in one of Islamorada's most exclusive waterfront settings.

88110 Overseas Hwy, 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
$665,000
2 Beds ⋅ 2 Baths ⋅ A12029820 MLS ⋅ Islamorada South Number 3 BLDG.
This island resort unit offers stations for dockage up to 25-foot boats daytime only, trailer storage and boat ramp. There is a pool for the development, pickle ball and tennis courts. The unit has hurricane impact windows as well as updated balcony area. It offers a large garage area with plenty of storage space. Injoy island living in the Keys .

118 Cortez Dr Unit #B, 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
$348,000
2 Beds ⋅ 2 Baths ⋅ A12028575 MLS ⋅ Plantation Villas BLDG.
Move-in ready townhouse located in the heart of Islamorada! This 2-bedroom, 1.5-bath home has been well maintained and features impact windows and doors, fresh interior paint, a metal roof in 2024, newer AC, upgraded electrical throughout and a washer and dryer in the unit. The galley kitchen provides ample cabinet space, induction stove top, dishwasher and pantry. Enjoy convenient access to the community pool right from your backdoor, and a designated parking spot directly in front of the unit. Plantation Villas is an ideal entry point into the Islamorada market--perfect as a primary residence or vacation getaway. Centrally located near schools, restaurants, shops, and grocery stores. Just a couple of miles south, Founders Park offers a wide range of amenities including an Olympic-size pool, tennis, pickleball, basketball courts, ball fields, a boat ramp, beach, and regular community events.

40 High Point Rd Unit #402, Islamorada
$3,350,000
4 Beds ⋅ 4 Baths ⋅ A12028354 MLS ⋅ White Marlin Beach Sec 1 BLDG.
TURN KEY Canal-Front Islamorada Home with Pool, Dock & Private Beach Access Luxury canal-front home in Islamorada offering spacious living, refined coastal design, and exceptional outdoor amenities. This meticulously maintained residence features a flexible split floor plan with a main-level living area, wet bar, bedroom, and full bath overlooking the outdoor kitchen and resort-style pool. Upstairs includes 3 additional bedrooms, 2.5 baths, an open living area, pristine kitchen, and walk-in laundry room/office. The fenced backyard is designed for easy living with turf, low-maintenance landscaping, and privacy! Concrete dock with 20,000 lb boat lift and space for multiple boats. Owners also enjoy access to the private White Marlin homeowners beach and close proximity to area amenities. The perfect Florida Keys getaway with strong monthly rental income potential! A rare opportunity for turnkey waterfront living in the heart of Islamorada.

145 Venetian Drive, 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
$14,900,000
6 Beds ⋅ 9 Baths ⋅ 620077 MLS
Yes, you can have it all! Tucked behind lush tropical landscaping and stretching across an expanse of more than 250 feet of sandy bayfront shoreline, 139 Gimpy Gulch is a rare Islamorada 3.2-acre estate designed for those who value privacy, boating, sunsets and effortless luxury in equal measure. This one-of-a-kind compound captures the spirit of the Keys with a level of scale and exclusivity seldom found on the islands. Arrive through private gates to discover a secluded retreat where every detail has been curated for relaxed coastal living. For boaters, a new boat dock offers immediate access to Florida Bay and immediate Atlantic Ocean access through nearby Snake Creek. This one-of-kind package also includes a 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 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 includes 2 acres of upland, 1.2 acres of baybottom, the separate vacant 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 bayfront retrea

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
$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
$2,400,000
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
$25,000,000
7 Beds ⋅ 10 Baths ⋅ A12022973 MLS ⋅ Islamorada BLDG.
Welcome to Serenity Cay, an exquisite Balinese-inspired estate where tranquility and luxury meet the endless beauty on the Florida Bay. A true masterpiece of engineering and design, this sprawling waterfront residence on nearly four acres offers an unparalleled blend of tropical elegance, sophisticated craftsmanship, and modern luxury. An expansive infinity-edge pool blends seamlessly into the sparkling waters of the bay while lush gardens create a serene oasis. The home's architecture showcases graceful, custom finishes and rich hardwoods, all hallmarks designs that evoke the spirit of the Islands. The interior is a seamless fusion of open-concept living spaces and private retreats. Soaring vaulted ceilings and vast windows invite abundant natural light and spectacular views of the bay, creating an indoor-outdoor flow. The primary suite serves as your personal sanctuary, complete with private terrace, spa-inspired bathroom, and walk-in closets fit for a connoisseur of fine living. Each guest has direct access to outdoor spaces and views. A versatile bunk room/media center sits just off the west wing of the home. The charming guest house is the perfect complement to the main home, nestled in its own secluded on site location this delightful addition exudes a warm, welcoming ambiance ideal for hosting guests, or as a private office or creative studio.

82768 Overseas Highway, Islamorada
$845,000
2 Beds ⋅ 3 Baths ⋅ 619965 MLS
Welcome to Port of Call--an intimate oceanfront enclave on Plantation Key where refined coastal living meets the effortless rhythm of the Florida Keys. Tucked within this exclusive 10-residence boutique community, 136 Aregood Lane offers a rare blend of luxury, privacy, and true serenity. This beautifully appointed 2-bedroom, 2.5-bath townhome is designed for both relaxation and adventure, featuring weekly rental eligibility, assigned dockage, a community pool, and a private rooftop deck with sweeping ocean views. Flooded with natural light, the main living level flows seamlessly to a private balcony where gentle breezes and glimpses of turquoise water set the tone for quiet island living. The thoughtful floor plan provides generous space for entertaining, while the additional half bath on this level ensures comfort for guests. Upstairs, two spacious en-suite bedrooms--each with its own balcony--offer peaceful retreats after a day on the water. With all impact windows and doors, the home delivers both beauty and peace of mind, allowing you to enjoy the Keys lifestyle with ease. For boating enthusiasts, the assigned boat slip with direct ocean access opens the door to world-class fishing, diving, and cruising. Spend your days exploring the Atlantic, then return to unwind by the community pool or stroll the private beach area as the sun dips below the horizon. Perfectly positioned in the heart of Islamorada, you're just minutes from Islamorada's renowned dining, shopping, and cultural experiences--yet worlds away from the everyday. Whether you envision a full-time residence, a weekend escape, or a high-demand investment property, this exceptional townhome delivers unmatched flexibility with its weekly rental capability and coveted oceanfront amenities. Port of Call is a place where luxury feels effortless, the ocean is your backyard, and every day begins with possibility.

136 Aregood Ln Unit 2A, Islamorada
$3,000,000
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
$298,000
1 Beds ⋅ 1 Baths ⋅ A12017273 MLS ⋅ Windley Key Mobile Home P BLDG.
Escape to your own slice of paradise with this cozy and beautifully kept 1-bedroom, 1-bath Jayco RV. Whether you’re looking for a peaceful weekend retreat, a seasonal getaway, or a spot with great rental potential, this charming hideaway has it all. Wake up to the soothing sounds of the Atlantic and enjoy unforgettable sunrises and sunsets right from the jetty. Nestled in a rare, intimate oceanfront community, you’ll love the relaxed lifestyle and low association fees. Spend your days soaking up the sun, launching your kayak or small boat, or taking advantage of the fish-cleaning station and marina. It’s the perfect chance to own a tranquil oceanfront retreat—simple, serene, and full of coastal charm.

84961 Old Hwy 17 Hwy, Islamorada
$13,500,000
7 Beds ⋅ 7 Baths ⋅ A12017379 MLS ⋅ Mat Ocean Bay BLDG.
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 and a valuable vacation rental license in place, 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.

75840 Overseas Highway, 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