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154 Milano Dr, Islamorada
$2,900,000
2 Beds ⋅ 2 Baths ⋅ 621951 MLS
HONEY LOOK AT THIS ONE! What does everyone want? The smallest house in a great neighborhood! 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
87455 Old Hwy Unit APT 234, Islamorada
$399,000
2 Beds ⋅ 2 Baths ⋅ 621854 MLS
Enjoy a tropical retreat at Plantation By The Sea, an oceanfront community in Islamorada. Relax beside the sparkling oceanfront pool or cast a line from the community fishing pier, then head out for waterfront dining, live music, and eclectic local shops. This inviting 2-bedroom, 1.5-bath condo offers a two-level layout with living spaces downstairs and both bedrooms upstairs. Bamboo flooring adds warmth to the living and dining areas and bedrooms. The updated kitchen features white cabinetry and generous counter and storage space. The open living and dining area flows onto a covered balcony nestled among tropical greenery - a pleasant spot for morning coffee or unwinding after a day exploring the island. Both upstairs bedrooms feature sliding glass doors opening to balcony spaces. An updated full bathroom with a tiled walk-in shower, a convenient downstairs half bath, and an in-unit Bosch washer and dryer add everyday comfort. Assigned covered parking and a ground-level storage room provide added convenience. Community amenities also include an oceanfront clubhouse with a kitchen, a pool table, and a ping-pong table - a great place to entertain friends and family. Take in ocean views while working out in the fitness center, or unwind in the men's and women's saunas. Gated entry and kayak and paddleboard storage add to the community's appeal. Nearby Founders Park offers a beach, Olympic-size swimming pool, tennis and pickleball courts, ball fields, and an amphitheater. Whether you're seeking a seasonal getaway or a year-round home, this welcoming condo puts the best of Islamorada within reach.

87455 Old Hwy Unit APT 234, Islamorada
79901 Overseas Highway Unit 410, Islamorada
$659,000
2 Beds ⋅ 2 Baths ⋅ 621648 MLS
Located in the heart of Islamorada, this 2 bedroom, 2 bath condo at The Palms of Islamorada offers beautiful Atlantic Ocean views and a spacious covered porch accessible from both the living room and primary bedroom. The primary suite features an en suite bathroom, while the covered porch provides an inviting outdoor space to enjoy the ocean breeze. Residents can enjoy a variety of resort style amenities within this gated oceanfront community, including a waterfront swimming pool, jacuzzi, tiki hut, fitness facilities, a community room, and covered parking. Situated on Upper Matecumbe Key near Mile Marker 80, The Palms is conveniently located near local favorites such as Lazy Days Restaurant, Papa Joe's, and Bud N' Mary's Marina, along with numerous other dining, shopping, and recreational options. A great opportunity for a primary residence or seasonal getaway in a central Islamorada location.

79901 Overseas Highway Unit 410, Islamorada
133 Anglers Way, Islamorada
$1,700,000
2 Beds ⋅ 3 Baths ⋅ 621627 MLS
Beautiful 2BR/2.5BA home in Anglers Reef, Islamorada's upscale gated oceanfront community. Features a 31' deeded BOAT SLIP with direct Atlantic access and no bridges, making it ideal for boating and fishing enthusiasts. Offered turnkey furnished with hardwood floors, granite countertops, stainless steel appliances, impact windows and doors, 2 private carports, two bedroom balconies, a front porch, and a rear porch. Enjoy a private community beach, pool, and oceanfront marina. Approved for weekly vacation rentals, offering an excellent investment opportunity or the perfect Florida Keys retreat!

133 Anglers Way, Islamorada
202 Hibiscus St, Islamorada
$749,000
2 Beds ⋅ 2 Baths ⋅ 621446 MLS
Charming CBS home located in Plantation Key Colony, situated on a corner lot and in an X flood zone. Offering over 1,300sf of living space, this 2 bedroom / 2 bath home features a spacious, open floor plan ideal for everyday living and entertaining. The generous kitchen offers abundant cabinetry and counter space and flows seamlessly into the main living area. Both bathrooms have been tastefully updated, and the interior has been freshly painted. Tile flooring throughout, recessed lighting, coastal colors, and a metal roof add to the home's appeal. Outside, enjoy a fenced yard, room for a pool, and ample off-street parking. The neighborhood offers a homeowners park with a boat ramp, providing convenient water access to enjoy the Florida Keys lifestyle. Conveniently located close to schools, shopping, dining, and local amenities, this inviting home is ready to enjoy.

202 Hibiscus St, Islamorada
111 Anglers Way, Islamorada
$1,199,999
2 Beds ⋅ 3 Baths ⋅ 621401 MLS
Experience the Florida Keys lifestyle at Anglers Reef, Islamorada's upscale gated oceanfront community. This beautifully appointed 2 bedroom, 2.5 bath home features a covered carport & four inviting porches, perfect for enjoying the tropical surroundings. Inside, you'll find Brazilian cherry hardwood floors, a spacious kitchen with granite countertops, stainless steel appliances, two breakfast bars, & abundant cabinetry. Additional features include a durable metal roof & impact windows & doors. Vacation rentals are permitted, making this an excellent opportunity for both personal enjoyment & investment. The home has been part of a successful rental program for many years & enjoys an established following of returning guests. Anglers Reef offers resort style amenities including two sandy beaches, an oceanfront swimming pool, & a private marina directly on the Atlantic Ocean. Enjoy your own Islamorada vacation retreat while generating rental income when you're away. A rare opportunity to own in one of Islamorada's most desirable oceanfront communities. Schedule your private showing today!

111 Anglers Way, Islamorada
40 High Point Rd Unit 703, Islamorada
$374,000
2 Beds ⋅ 2 Baths ⋅ 620635 MLS
Turn key furnished condo in Islamorada! This beautifully appointed 2 bedroom, 2 bath condo features an open floor plan, abundant natural light and a rare balcony. Remodeled unit which includes impact windows and doors, crown molding, wood engineered laminate flooring, and a full size washer and dryer. The open-chef's kitchen boasts a spacious breakfast bar, extra tall hardwood cabinets, granite counter tops and backsplash, under-cabinet and recessed lighting, a dishwasher, and a newer refrigerator in 2022. The primary ensuite offers a walk-in closet with custom shelving. AC was replaced in 2023, Metal roof installed in 2024. The complex offers a heated swimming pool, and clubhouse. Founder's Park, Islamorada's Community Park, is on the same island. Admission into the park is free for Islamorada residents. The park offers an Olympic size swimming pool, tennis courts, pickleball courts, ball fields, marina, beach and boat ramp. Plantation Villas is close to Plantation Key Elementary School and Coral Shores High School, grocery store, shopping, restaurants and movie theater.

40 High Point Rd Unit 703, Islamorada
87200 Overseas Hwy Unit D3, 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
87200 Overseas Hwy Unit APT A 7, 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
80450 Overseas Highway Unit 204, Islamorada
$535,000
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
88181 Old Hwy Unit B3, Islamorada
$850,000
2 Beds ⋅ 2 Baths ⋅ 619533 MLS
Islamorada luxury condo and boat slip for boats to 44' - the perfect combination for serious boaters! Located within a 14-acre, resort-style ocean front community of just eight buildings, this home sits in a peaceful low-rise building with only three units. As an end unit with no one above or below, it feels very much like a single-family home. Windows on three sides bring in natural light and a comfortable, airy feel throughout. The kitchen and baths are up-to-date and beautiful. The layout includes 2 bedrooms and 2 baths, plus a screened porch and an expansive 650+/- sq ft open patio overlooking a peaceful swimming lagoon, surrounded by mature trees. You'll want to dine outdoors every night! It's a quiet, private setting that still keeps you close to everything. Impact windows and doors throughout - and - electric roll down shutters for the screen porch. For boaters, the marina is a standout. There's a ramp, shore power, ice, and a private fuel dock exclusively for owners which is an uncommon and valuable feature. It's not just more convenient to gas up at home... it's less expensive than local marinas too! This unit comes with a slip that can accommodate up to a 44' boat and is in a prime location, close to shore and just a short distance from the unit. It's also near a popular gathering spot where owners tend to unwind and connect at the end of the day. Community amenities include an oceanfront pool, clubhouse, a lighted tennis court, and an additional court for tennis or pickleball. The grounds are lush, green, well-kept and spread out, giving the entire property a relaxed, uncrowded feel. Pet-friendly with no size restrictions. If you're looking for a low-maintenance Keys home with excellent dockage and a true Keys boating lifestyle, this one checks the boxes. Offered beautifully furnished. An absolute must-see! Slip #24. Using exterior measurements, total footprint is 2,650 sf +/-.

88181 Old Hwy Unit B3, Islamorada
118 Cortez Dr Unit B2, Islamorada
$649,000
2 Beds ⋅ 2 Baths ⋅ 619328 MLS
This island resort style unit offers stations for dockage up to 25-foot boats, 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. Easy access to shops and restaurant's.

118 Cortez Dr Unit B2, Islamorada
77340 Overseas Hwy, Islamorada
$3,799,999
2 Beds ⋅ 2 Baths ⋅ 619064 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. An existing legal nonconforming home with a waterfront swimming pool currently sits on the property and may be used as a residence or rental while architectural plans and permits are finalized, offering flexibility during the planning process. For buyers who understand the value of land in the Florida Keys, this offering represents something increasingly difficult to find: the opportunity to create a custom waterfront estate tailored entirely to your vision, rather than inheriting someone else's. A remarkable parcel for a remarkable build.

77340 Overseas Hwy, Islamorada
121 Lisbon Ct, Islamorada
$2,000,000
2 Beds ⋅ 2 Baths ⋅ 618666 MLS
What does everyone dream of? The smallest house in the best neighborhood -- and this one delivers. Welcome to easy, breezy living in Port Antigua, where charm, quality, and location come together beautifully. This thoughtfully updated home is being offered fully furnished -- from stylish pieces down to kitchen wares, dishes, and linens -- making your transition to the Keys seamless. Just bring your flip-flops. Impact windows and doors are installed throughout, including three skylights set into the concrete roof, so you can relax knowing your investment is well protected while natural light pours in from above. Upstairs, the open-concept living space feels airy and inviting, perfectly suited for gathering with friends and family. Triple sliding glass doors lead to a spacious second-floor terrace, creating that effortless indoor-outdoor flow we all love about coastal living. A separate laundry room just off the kitchen adds everyday convenience without sacrificing style. Both bedrooms feature their own sliding glass doors to the terrace, welcoming in sunshine and soft island breezes -- a gentle reminder that you're living somewhere special. Downstairs, you'll find abundant storage space and a 70-foot concrete dock complete with a fish-cleaning station and boat lift -- ready for offshore adventures or sunset cruises at a moment's notice. The yard is designed for low-maintenance enjoyment, with river rock and a clean concrete driveway in front, and artificial turf in the back for a lush look without the upkeep. This is the one you've been waiting for -- refined yet relaxed, polished yet playful. A perfectly sized slice of paradise in one of the Keys' most desirable neighborhoods.

121 Lisbon Ct, Islamorada
84961 Old Hwy Unit 18, Islamorada
$849,900
2 Beds ⋅ 2 Baths ⋅ 618847 MLS
Beautiful Atlantic Ocean views surround this newer concrete home featuring an open-concept floor plan with 2 bedrooms and 2 bathrooms. Tastefully furnished with a coastal flair, the spacious living area flows into a kitchen appointed with custom wood cabinetry, quartz countertops, stainless steel appliances, and a high-end water filtration system. Impact windows and doors, plantation shutters, new A/C, and new gutters add to the home's quality. A true boater's dream, the property offers direct ocean access and convenient Florida Bay access via Snake Creek. Step outside and enjoy the island breeze, or take advantage of the community's wonderful oceanfront amenities, including a chickee hut, oceanfront jetty, and dock privileges. Relax under the chickee hut while taking in beautiful sunrises and breathtaking sunsets over the water. Whether you're seeking a full-time residence or the ultimate Florida Keys retreat, this home delivers the best of the Keys lifestyle. YOU OWN THE LAND!

84961 Old Hwy Unit 18, Islamorada
87200 N Overseas Hwy Unit N2, Islamorada
$630,000
2 Beds ⋅ 2 Baths ⋅ 617971 MLS
Private location for your pleasure at this roomy townhouse offering an abundance of space to enjoy. Spiral stairs leading to the primary suites with an additional loft for your quests. Soft carpet on the living area floors with tile in the remodeled kitchen and beautiful bathrooms. Two pets allowed, with first come first serve the waterfront area. Pool and club house for your recreation along with a nice, landscaped community for your pleasure. 28-day rentals permitted. Garden setting from you extended living room to enjoy the outdoors at your back yard.

87200 N Overseas Hwy Unit N2, Islamorada
80450 Overseas Hwy Unit APT 106, Islamorada
$550,000
2 Beds ⋅ 3 Baths ⋅ 618784 MLS
Set in the very center of Islamorada's vibrant island community, this 2BD/2.5BA townhouse style condo in Sand Pebbles offers privacy, comfort, and convenience. The ground level features two spacious en-suite bedrooms, each with its own private porch. Upstairs, enjoy a bright open-concept living, dining, and kitchen area plus a convenient half bath. With 1,303 sq ft and multiple outdoor living spaces including an outdoor spiral staircase feature, this home lives large. Sand Pebbles is a well maintained bayfront community offering a heated pool, tiki hut, garden areas, onsite trailer storage, and a bayfront observation deck. Walk or bike to marinas, dining, and shopping to enjoy the best of Islamorada living.

80450 Overseas Hwy Unit APT 106, Islamorada

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