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31315 Ave B, Big Pine
$619,000
3 Beds ⋅ 2 Baths ⋅ 621796 MLS
Welcome to this elevated 3-bedroom, 2-bath home nestled in a quiet neighborhood in Big Pine Key. This well-maintained property features a BRAND-NEW 2026 ROOF, along with impact-rated windows and doors for added peace of mind and storm protection. The open-concept living and kitchen area creates an inviting space for everyday living and entertaining. All three bedrooms are generously sized, each featuring its own walk-in closet. Situated on a corner lot, the property offers ample parking for multiple vehicles, a boat, boat trailer, or other recreational toys. Conveniently located near shopping, dining, and a boat ramp, this home offers the perfect blend of comfort and convenience. Whether you're looking for a full-time residence or a solid investment opportunity, this property checks all the boxes.

31315 Ave B, Big Pine

1519 Johnson St, Key West
$2,190,000
5 Beds ⋅ 4 Baths ⋅ 621798 MLS
Discover island living at this spacious two-story, 5-bedroom, 4-bathroom retreat nestled in a quiet residential neighborhood right in the heart of Key West. Perfectly positioned this inviting property offers easy access to the beaches, tennis and pickleball courts, bocce courts, and the local dog park. Enjoy a leisurely bike ride to the vibrant energy of downtown Key West and Duval Street, then return home to your own private tropical escape. Inside, an open and welcoming floor plan features beautiful gray-blue tile flooring, a stylish kitchen, and generous living and dining areas designed for gathering with family and friends. With room to accommodate up to 14 people, the home offers exceptional flexibility for a large family, visiting guests, or those seeking a second home with income potential. The upper level provides two additional rooms, ideal for extra sleeping space, a home office, or a relaxing den. Step outside to a private backyard oasis featuring lush tropical landscaping, an expansive swimming pool, and a spacious deck perfect for outdoor dining, entertaining, and soaking up the Florida sunshine. A detached pool house adds another dimension of versatility, complete with a one-bedroom, one-bathroom studio and kitchenette--ideal for guests or additional living space. Offered fully furnished and with a history of vacation rental income, this property presents an exciting opportunity for investors seeking an income-producing asset or buyers looking to combine a personal island getaway with rental potential. Whether you envision a welcoming family retreat, a second home in paradise, or an investment in the Florida Keys lifestyle, 1519 Johnson Street offers space, flexibility, and a desirable central location to make it your own.

1519 Johnson St, Key West

520 Sombrero Beach Rd, Marathon
$4,399,000
4 Beds ⋅ 5 Baths ⋅ 621797 MLS
Breathtaking water views and immediate ocean access set the stage for an exceptional waterfront lifestyle at this stunning and impeccably kept modern 2-story home in Sombrero Beach, an exclusive neighborhood of high-end homes just steps to the beach and minutes to Marathon Jet Center. Offering 4 bedrooms, 5 bathrooms, and approximately 3,500 sq. ft. of beautifully appointed living space, this waterfront retreat places the Atlantic Ocean just moments from your dock. Soaring ceilings and an expansive open floor plan create a bright, inviting atmosphere with stunning water views from the main living areas. The chef's kitchen features marble countertops, premium stainless steel appliances, a wine cooler, and a spacious island with seating for four, flowing seamlessly into the dining and living areas. A separate sitting area offers additional space to unwind. Upstairs, two generously sized primary suites each feature private balconies with glass railings showcasing panoramic ocean views, along with luxurious en suite baths featuring soaking tubs and separate rain showers. A wet bar with an ice maker, mini refrigerator, and wine cooler sits between the suites. Two additional guest bedrooms are located on the main level with a bath for each. Outside, an expansive lanai surrounds the heated saltwater pool and spa which is fully automated to work from your cell phone and is complemented by a poolside tiki hut with a fully equipped outdoor kitchen, grill, refrigerator, microwave, and TV. A convenient cabana bath provides easy access from the pool area. Boating enthusiasts will appreciate the 50' dock, 14,000 lb. boat lift, fish-cleaning station, and immediate Atlantic Ocean access. Solid CBS construction with concrete roof and impact doors and windows. Offered Turn-Key. Seller financing offered to qualified buyers! Zoned for weekly vacation rentals, this property offers solid rental history and presents an excellent investment opportunity.

520 Sombrero Beach Rd, Marathon

1041 Buttonwood Dr, Sugarloaf
$9,970,000
6 Beds ⋅ 8 Baths ⋅ 621794 MLS
THE AZURE ESTATE | Where Luxury Meets Wellness. Discover a stunning, brand-new solid concrete architectural masterpiece on the open waters of Sugarloaf Key, where striking design, coastal resilience, and wellness-inspired luxury create an extraordinary Florida Keys lifestyle. Designed for strength and peace of mind, this remarkable elevated residence pairs hurricane-resistant design features with walls of glass and endless ocean views. Step inside to a breathtaking 19-foot, double-height living room filled with natural light. Porcelain floors, elegant glass railings, and a private hydraulic elevator bring comfort and sophistication to every level. The chef's kitchen dazzles with quartzite countertops and Monogram appliances, complemented by a custom bar and dramatic stone wine display. Four private suites in the main residence open to covered waterfront terraces, inviting you to wake up to endless ocean views and gentle island breezes. Crowning the home, a full rooftop deck offers sweeping 360-degree panoramas from sunrise to sunset-an inspiring retreat for morning yoga, meditation, or unforgettable gatherings under the stars. Outside, a resort-style pool and spa, outdoor shower, convenient poolside bathroom, landscape lighting, and expansive covered entertaining areas invite you to slow down and savor island life. A planned 226-foot dock, included in the purchase price, will further elevate the boating experience. One of the property's most distinctive features is its solid reinforced-concrete parking structure, designed to accommodate up to 6 vehicles, with generous overhead storage space and convenient dual access. Boasting an impressive elevation of 11 ft 2 inch NGVD, above the designated 10-ft NGVD flood elevation, this structure offers a significant advantage in the Florida Keys, providing an added measure of protection against potential flooding during hurricanes, storm surges, and severe weather conditions. Built with solid structural concrete throughout!

1041 Buttonwood Dr, Sugarloaf

312 E Caribbean Dr, Summerland
$2,400,000
3 Beds ⋅ 2 Baths ⋅ 621795 MLS
OPEN WATER VIEWS. ENDLESS POSSIBILITIES. YOUR SUMMERLAND KEY WATERFRONT RETREAT. Some properties are all about the location - and this is one of them. Set along the open water in sought-after Summerland Key, this well-maintained 3-bedroom, 2-bath concrete home offers incredible unobstructed views, easy boating access, and the opportunity to create your own vision of Florida Keys living. Outside, the open-water setting takes center stage, with expansive views that bring the beauty of the Florida Keys into everyday life. The concrete construction offers a solid foundation, while the fenced property and electric entry gate provide added convenience. From the covered screened balcony upstairs, you can soak in the beauty and catch spectacular sunset views. The existing interior retains its original character, providing a wonderful starting point for buyers ready to reimagine the space and make it their own. Whether your dream is a modern coastal retreat, a relaxed waterfront getaway, or a personal island escape, the possibilities are here. For boaters, waterfront living is about more than a view - it's about getting out on the water and enjoying everything the Keys have to offer. Here, the setting provides the backdrop for days spent exploring, fishing, lobstering, and returning home to spectacular open-water scenery. Straight access to the Atlantic and Gulf waters. Opportunities to secure an open-water property in Summerland Key and transform it to suit your own style are increasingly appealing. Bring your vision, embrace the location, and create something special in the Florida Keys. The views are already here. The next chapter is yours to create.

312 E Caribbean Dr, Summerland

130 Lorelane Pl, Key Largo
$1,725,000
3 Beds ⋅ 2 Baths ⋅ 621793 MLS
Beautifully Maintained Oceanside Waterfront Home in Key Largo! Enjoy the Florida Keys lifestyle in this inviting, move-in-ready 3-bedroom, 2-bath home situated along a picturesque oceanside canal. Offering 70 feet of waterfront with concrete dockage and a 13,500-pound boat lift, this property combines comfortable coastal living with wonderful outdoor entertaining spaces. Step inside to discover a bright, welcoming interior featuring an open living and dining area, an attractive kitchen with island seating, and impact windows and doors throughout. The comfortable living spaces extend outdoors to a spacious covered balcony and open sun deck, perfect for morning coffee, afternoon relaxation, or gathering with family and friends. The downstairs level offers covered parking, storage, and a versatile bonus room ideal for recreation or entertaining. Surrounded by lush tropical landscaping, the property features a covered outdoor entertainment area with bar, inviting waterfront spaces, and room for a future pool. Whether enjoying the beautiful canal views, spending time on the water, or simply relaxing in your own tropical retreat, this home offers the best of casual Keys living. Conveniently located near shopping, restaurants, and Key Largo Community Park, this home offers a wonderful combination of waterfront tranquility and everyday convenience. Move right in and start living your Florida Keys dream!

130 Lorelane Pl, Key Largo

34 Key Haven, Key Haven
$1,395,000
4 Beds ⋅ 2 Baths ⋅ 621790 MLS
4 BEDROOMS. 60 FT OF WATERFRONT. JUST $800/SF IN KEY HAVEN! Discover an exceptional opportunity to enjoy the boating lifestyle at 34 Key Haven Road. This 4 bedroom, 2 bathroom waterfront home offers 1,743 SF of living space, a wide canal, and quick access to both the Atlantic and Gulf. Set on a 6,000 SF lot, the home combines comfortable island living with the features boaters appreciate most. Inside, a bright, open layout centers around an updated kitchen with quartz countertops and stainless steel appliances, connecting naturally to the living and dining areas. Sliding glass doors from the main living space and primary bedroom open to a spacious covered patio overlooking the water. The flexible floor plan includes a fourth bedroom with a separate entrance, ideal for guests, a private office, or additional living space. Outside, 60 feet of concrete seawall provides generous dockage, making spontaneous days on the water part of everyday life. A metal roof, accordion shutters, CBS construction, and elevated setting add practical appeal and low insurances. Located just minutes from Key West, this home delivers the space, waterfront access, and relaxed lifestyle that make Key Haven so desirable. Whether you're searching for a full-time residence or your own boating retreat, 34 Key Haven Road deserves a closer look!

34 Key Haven, Key Haven

16 Sunrise Cay Dr, Key Largo
$18,750,000
5 Beds ⋅ 7 Baths ⋅ 5058 MLS
Positioned closer to the ocean than any other home on Sunrise Cay, 16 Sunrise Cay Drive offers a remarkable connection to the Atlantic and a distinctive arrangement of two private residences joined by a covered breezeway. Beautifully remodeled, this inviting retreat combines sophisticated coastal interiors with sweeping ocean views and exceptional flexibility for family and guests. The light-filled main residence is an intimate two-bedroom oceanfront home, with expansive windows, wraparound decks, and an elevator. Crisp white interiors, natural textures, and subtle touches of green create a fresh, relaxed elegance. The kitchen opens toward the ocean, while a newly added entertaining bar features custom cabinetry, warm natural finishes, and a striking sculptural chandelier. The spacious primary suite enjoys ocean views, vaulted ceilings, separate bathrooms, custom closets, a sitting area, and a private deck. Across the covered breezeway, the three-bedroom guest residence offers a home unto itself, with ensuite bedrooms, comfortable living areas, a full kitchen, its own elevator, and a private porch with ocean views across the shared swimming pool. The thoughtful layout allows everyone to gather easily while enjoying the comfort and privacy of separate living quarters. Outdoors, the pool and spa form a welcoming gathering place between the residences, surrounded by tropical landscaping and refreshing ocean breezes. Spectacular sunrises, unforgettable moonrises, and the soft reflected glow of western sunsets lend a different beauty to every hour. A private beach invites paddleboarding, while a boardwalk leads to an observation platform for fishing or simply enjoying the water. A 50-foot slip in the protected Sunrise Cay Marina completes the offering. With its extraordinary oceanfront position, gracious indoor-outdoor spaces, and uniquely versatile accommodations, 16 Sunrise Cay is a refined yet relaxed Florida Keys retreat.

16 Sunrise Cay Dr, Key Largo

692 Blackbeard Rd, Little Torch
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 621786 MLS
Welcome to your piece of paradise in the Florida Keys! This beautifully situated 3-bedroom, 2-bathroom canal-front home offers the perfect combination of comfort, privacy, and island living. Located just around the corner from Dolphin Marina, the property offers convenient boating access to open water, with access to both the Gulf and Atlantic Ocean sides. Whether you enjoy fishing, diving, snorkeling, or simply spending time on the water, this location puts the best of the Florida Keys lifestyle within easy reach. The home features a spacious primary suite with a private bathroom, two additional bedrooms, and an inviting living space. Step outside onto the screened porch overlooking the canal, an ideal spot to enjoy your morning coffee or unwind at the end of the day. The private swimming pool, fenced yard, and outdoor entertaining areas create a wonderful setting for relaxing and enjoying the tropical surroundings. Additional features include a stilt-style design, central air conditioning, and convenient access to the waterfront. Ideally located near Looe Key Reef, Bahia Honda State Park, local marinas, and waterfront restaurants, the property is approximately 20 minutes from Marathon and 25 minutes from Key West. Whether you're looking for a full-time residence, a second home, or your own waterfront retreat, this Little Torch Key property offers an opportunity to enjoy the boating lifestyle and natural beauty that make the Florida Keys so special.

692 Blackbeard Rd, Little Torch

58 Cannon Royal Dr, Shark Key
$4,750,000
3 Beds ⋅ 3 Baths ⋅ 621785 MLS
Discover effortless waterfront living in the exclusive gated community of Shark Key. Beautifully designed and newly constructed, this stunning residence is offered fully furnished and turnkey, allowing you to move right in and begin enjoying the best of the Florida Keys. Combining coastal sophistication with relaxed island living, the home offers breathtaking open-water views, spectacular sunsets, and an exceptional indoor-outdoor living experience. Designed to embrace its waterfront setting, the residence features an inviting, open layout filled with natural light, beautiful water views, and a seamless connection to the outdoors. Expansive covered balconies and terraces extend the living space, providing wonderful areas for relaxing, dining, and entertaining while enjoying the surrounding tropical beauty and gentle island breezes. The private pool and outdoor living areas create a beautiful setting for spending time with family and friends or simply unwinding as the sun sets over the open water. Additional features include an elevator, enclosed storage, and abundant covered parking beneath the home. The generous ground-level area offers flexibility and possibilities for a variety of uses, adding to the property's convenience and appeal. Approved permits for an observation dock provide the opportunity to further enjoy the property's spectacular waterfront setting and sunset views. Located just minutes from Key West, Shark Key is one of the Florida Keys' most prestigious gated communities, offering residents an array of resort-style amenities, including tennis and pickleball courts, a swimming lagoon, and a private beach area. New construction, fully furnished, and completely turnkey, this is an opportunity to enjoy the beauty of the Florida Keys without the wait. Simply move in, settle in, and enjoy.

58 Cannon Royal Dr, Shark Key

29667 Flying Cloud Ave, Big Pine
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 621780 MLS
Welcome to island living and a tropical lifestyle. Embrace your tropical vibes in this gently used, newer-built home ready for all your Florida Keys needs. This waterfront property is ideal for those looking for a blank slate; it's ready for your personal design and touches, inside and out, so you can create your own amazing island oasis. Ideal for entertaining, relaxing, creating fabulous memories, and sharing your paradise with friends and family. The living area opens to a stunning, spacious porch/patio, perfect for sunsets, sipping coffee or cocktails, and enjoying peaceful canal views. Your primary suite includes an ensuite bath, and two additional bedrooms provide guest rooms or a home office. Situated in Pine Channel Estates, this home offers 3 bedrooms, 2 baths, and everything you need for the ultimate destination. For the boating enthusiasts, you will appreciate the 75' concrete dock, which is ready for a boat lift and all of your water toys. You're minutes from boating access to both the Gulf and the Atlantic Ocean. Additional highlights include impact windows and spacious covered parking on the lower level, with room for extra storage for all your boating and fishing gear. Known for its boating and fishing, this location offers convenience and privacy. This home is centrally located between Key West and Marathon, with great dining, shopping, plenty of outdoor activities, and all the historical sights and scenes. Spend your days at your waterfront retreat or explore island hopping and sandbar BBQs; this home offers the chance to embrace laid-back island living at its best!

29667 Flying Cloud Ave, Big Pine

80 Ocean Front Dr, Key Largo
$7,295,000
4 Beds ⋅ 4 Baths ⋅ 621778 MLS
A rare opportunity to own one of the most extraordinary oceanfront properties in the Florida Keys, offering the exceptional combination of expansive Atlantic Ocean frontage and over 110 feet of protected canal dockage. Situated on a spectacular private peninsula extending into the Atlantic, this remarkable estate encompasses approximately 1.6 acres of upland and an additional 0.7 acres of submerged land. Beyond the gated entrance, a long, winding driveway introduces a property defined by privacy, exclusivity, and breathtaking panoramic ocean views. What truly sets this property apart is the ability to enjoy unobstructed oceanfront living while having over 110 feet of protected dockage along a concrete seawall, providing convenient boating access without sacrificing the beauty and tranquility of the open Atlantic. The existing executive residence features soaring ceilings, a dramatic curved staircase, spacious entertaining areas, and spectacular water views. The main living levels offer four bedrooms and three-and-a-half bathrooms, with additional ground-level space below base flood elevation. Outside, a swimming pool overlooks the Atlantic, while a private tiki hut at the end of the peninsula offers an unforgettable setting surrounded by tropical waters. Whether you envision restoring and enhancing the existing residence or creating a magnificent new oceanfront estate, the possibilities are extraordinary, subject to applicable approvals. Properties combining substantial upland acreage, panoramic Atlantic views, exceptional privacy, and protected dockage are exceedingly rare in the Florida Keys. This is more than an oceanfront home; it is an opportunity to create a lasting waterfront legacy.

80 Ocean Front Dr, Key Largo

322 Mahogany Dr, Key Largo
$635,000
3 Beds ⋅ 1 Baths ⋅ 621775 MLS
PRICE IS NOT THE ONLY IMPROVEMENT!! Discover the potential in this elevated 3 bedroom home in Pamela Villa, with cathedral ceilings, crown molding, and vinyl plank flooring throughout. The third bedroom offers a distinctive hardwood ceiling and private entrance. The larger size bathroom has an oval tub. Enjoy the tropical landscaping, a fully fenced backyard, covered parking, and a legal finished downstairs area that adds flexibility. Recent improvements include complete exterior painting and replacement of staircase railings, new range hood, ceiling fans. Located in an X flood zone, with no HOA fees. Expansion downstairs is possible, to add a bathroom and more living space. Conveniently located near shopping, dining, and John Pennekamp Coral Reef State Park plus it is convenient to Key Largo amenities including the Murray Nelson Cultural Center. Many are within walking/biking distance including Key Largo Park and Jacobs Aquatic center, professional Pickle ball courts, and the YMCA at the park The property is also covered by a Truly Nolen termite contract which transfers to the Buyer.

322 Mahogany Dr, Key Largo

817 Pearl St, Key West
$825,000
1 Beds ⋅ 1 Baths ⋅ 621769 MLS
Charming Home in the Meadows, Old Town, Key West. This beautiful completely renovated one bedroom cottage on Pearl Street is move in ready, and is being sold furnished. Stepping into the home through the custom built Dutch-door, the interior is bright, the walls are shadow-gap wood, there is new flooring, and recessed LED lighting throughout. The Bedroom has a murphy bed, and built in bedroom drawers, with additional storage. The Kitchen has custom cabinets, granite countertops, and is steps away from the back deck with a Tiki and wet bar - and outside seating area. Mitsubishi mini split AC, Custom shades, All new impact windows and doors, and the front Dutch Door has hurricane panels. During the renovation, the whole house was insulated between the studs, 3/4 inch pressure treated plywood added, then 1' fire rock, and then lap siding- PT-kiln dried-dipped on both sides with primer. This property is completely fenced, has a sprinkler system, Outdoor shower, and the best part- is a wonderful front porch to relax and watch the world go by! Home Owners insurance is $ 1471.58, Flood Insurance is $ 1463.00

817 Pearl St, Key West

251 Pelican Ln, Big Pine
$739,900
2 Beds ⋅ 2 Baths ⋅ 621770 MLS
Discover the charm of Florida Keys waterfront living on two full lots in beautiful Big Pine Key! This well maintained concrete block home offers an inviting blend of comfort, privacy and exceptional outdoor space. The bright, open living and dining area features expansive windows overlooking the peaceful canal, while the cheerful white kitchen offers granite countertops and backsplash. Laminate flooring, two screened porches, including one off the primary suite, and two separate exterior stairways provide convenient access to the main living level adding to the home's comfort and convenience. Step outside to your own tropical retreat, where lush landscaping and an abundance of fruit trees, including mango, papaya, dragon fruit, grapefruit and bananas, create a beautiful island setting. Both lots feature extensive concrete dockage along a swimming canal, perfect for kayaking, paddleboarding or simply enjoying life by the water. Across the canal, government owned land provides a natural backdrop for watching tropical birds and Key deer. One of the property's most impressive features is the approximately 1,200 square foot completely enclosed lower level with open truss construction and no interior support columns, offering exceptional space for a garage, workshop or storage. The second lot provides additional room to enjoy today and exciting possibilities for future improvements, subject to applicable regulations and approvals. Impact windows and doors, a metal roof, wraparound decking, a spacious laundry room, generous parking and a fully fenced property complete this unique offering. Conveniently located near shopping, dining and recreation, with easy access to Marathon and Key West. Whether you're looking for a year round residence or an island getaway, this special property offers the space, waterfront amenities and tropical lifestyle you've been dreaming of!

251 Pelican Ln, Big Pine

2827 Harris Ave, Key West
$2,195,000
5 Beds ⋅ 5 Baths ⋅ 621768 MLS
This stunning 5-bedroom, 5-bathroom fortress of a home, completely reimagined and rebuilt in 2023, offers 3,062 sq. ft. of luxurious living space on a 5,040 sq. ft. lot. Featuring 9-foot ceilings, custom wood cabinetry, porcelain wood-look tile and luxury vinyl flooring, the home showcases exceptional craftsmanship throughout. The chef's kitchen is a true centerpiece, featuring an impressive 17-foot island with seating for eight, professional grade appliances, a 36-inch gas range with vented hood, and a wine refrigerator. The spacious primary suite features a walk-in closet and a spa inspired wet room with dual showerheads, a clawfoot soaking tub, and dual vanities. Additional conveniences include laundry areas on both floors and abundant storage, including attic and under-home space. Built with durability and efficiency in mind, the home features impact resistant windows, spray foam insulation, and a double strapped aluminum standing seam roof. The backyard offers an inviting outdoor retreat, highlighted by a heated pool and traditional thatched chickee hut, perfect for relaxing or entertaining in true Key West style. From the moment you step inside, you'll appreciate the striking architectural symmetry, exquisite craftsmanship, and meticulous attention to detail that make this exceptional Key West residence truly one of a kind. *Please note that some photos have been digitally staged or altered*

2827 Harris Ave, Key West

16 Avacado St, Islamorada
$23,500,000
9 Beds ⋅ 11 Baths ⋅ 621766 MLS
Rarely do the lines intersect between architectural excellence, positioning, thoughtfulness, and elite water access, until now. Set on a private street in downtown Islamorada, this gated bayfront property includes a main house, guest house, sunset views, and 170 feet of dockage. Built above flood, the main house offers 6 bedrooms, 6 bathrooms, 2 half baths, and an office. A pivot front door opens to living spaces overlooking the bay. The formal dining room includes a wet bar and wine cellar, while the kitchen's double islands provide room for preparing meals and gathering. A water vapor fireplace anchors the living room, and ceilings open to the second floor above both the living room and kitchen. A floating staircase and elevator connect the two levels. Two primary suites, one on each floor, offer a choice of setting. Both feature freestanding soaking tubs and bay-facing windows that turn opaque at the touch of a button. A powder room serves the main living area, and a cabana bath is located by the pool. Outside, the infinity pool's swim-up bar and submerged seating meet the outdoor kitchen counter. The gazebo is equipped with roll-down hurricane shades. Along the waterfront, a 70-foot concrete jetty shelters the basin around the beach. An additional 100-foot wood dock provides two boatlifts (30,000 lb & 10,000 lb) and space for visiting boats. Across the front courtyard, the guest house offers independent living space, including 3 bedrooms and 2 bathrooms upstairs. Three air-conditioned garage bays occupy the ground floor. Tropical landscaping chosen for the Keys climate keeps upkeep manageable. A 100 kW standby propane generator serves the entire property, and an organic mosquito misting system helps make the grounds more comfortable. Years of planning and construction come together in a property designed for life on the bay, from everyday living to time spent on the water.

16 Avacado St, Islamorada

140 Tavern Dr, Key Largo
$498,000
1 Beds ⋅ 1 Baths ⋅ 621765 MLS
A rare opportunity to own a piece of Florida Keys history in the heart of Historic Tavernier. Built in 1934, this authentic Keys cottage dates back to a remarkable chapter in Florida Keys history, and when homes were built with character, craftsmanship & materials that are increasingly difficult to find today. It was an era when Henry Flagler's Overseas Railroad still connected the islands, Ernest Hemingway was writing & fishing in Key West, & the Florida Keys were a quiet collection of fishing villages, artists, pioneers & people drawn to a different way of life. From the original Dade County pine to the architectural details that reflect its nearly century-old roots, this is a home with a story to tell. Surrounded by mature tropical landscaping, the property has that timeless, old-Keys charm that simply can't be recreated with new construction. And the location is just as special as the home itself. Tucked within Tavernier's established historic district, you're just a short stroll from Old Settlers Park, Cafe Moka, locally loved restaurants, Sunshine Market, shops & even a spa. It's the kind of community where you can step outside your door, walk to your favorite morning coffee spot, run into familiar faces & enjoy a slower, more connected way of life. And because this is the Keys, access to the water is never far away. A nearby small beach for residents to enjoy the ocean water as well as a launch offers access for kayaks or small skiffs, & a convenient larger boat ramp is just up the road. Additionally, a marina across the road provides an options for larger vessels. Tavernier also puts you right between Key Largo & Islamorada, giving you convenient access to the everyday essentials of both communities. For the person who appreciates historic architecture, original craftsmanship & the beauty of preserving something with a story, this is an opportunity to own something truly special.

140 Tavern Dr, Key Largo

27385 Saint Lucie Ln, Ramrod
$2,199,000
4 Beds ⋅ 3 Baths ⋅ 621763 MLS
Tropical Keys Oasis - Waterfront Luxury Living Come experience this completely renovated, one-of-a-kind tropical oasis that feels like you have checked into a luxury 5-star resort. Relax in the sparkling pool surrounded by lush, mature landscaping, including coconut palms, banana trees, mango trees and a Hass avocado tree. Vibrant bougainvillea archways create a stunning entry to one of the most exquisitely landscaped homes on the island. Outdoor living here is elevated to the next level and is perfect for entertaining. Enjoy 60 feet of waterfront with an expansive maintenance-free deck, a 15,000-lb boat lift and a drop dock perfect for swimming in the lagoon or launching kayaks. Inside, discover a beautiful 4-bedroom, 2.5-bath home featuring a chef's kitchen with a 6-burner gas stove, double farm sink, all-new stainless-steel appliances and a massive center island with abundant storage, so you can enjoy everyday luxury living. Gorgeous tile flooring flows throughout. The first floor offers three guest bedrooms, a stylishly renovated bath, a convenient half bath and a full laundry room with gas dryer. The spacious living room opens through triple sliding glass pocket doors to a screened porch secluded by palms, bringing your indoor living outdoors in the winter and ideal for morning coffee or dining al fresco year-round. Upstairs, the primary suite is a private retreat with panoramic water views, a custom walk-in closet and a spa-inspired bathroom with an oversized shower featuring six body jets, a handheld sprayer and a ceiling-mounted rain shower. Dual vanities and a lighted mirror complete this luxurious sanctuary. Additional features include: - Brand-new impact windows and doors throughout - Metal roof - Fully fenced backyard, perfect for pets and privacy - 300 sq. ft. storage room with impact windows and doors - Irrigation system - Propane gas - Endless on-demand gas water heater - And so much more!

27385 Saint Lucie Ln, Ramrod

175 W Ave A, Key Largo
$3,300,000
4 Beds ⋅ 4 Baths ⋅ 621761 MLS
CASA COLADA is a stunning, newly constructed home in Key Largo, with direct bay access & open-water views. This home is designed for both relaxation and entertainment. The outdoor oasis features a heated swimming pool and ample space to soak up the island lifestyle. Boating enthusiasts will appreciate the proximity to the bay, boat lift and storage area, which provides the perfect place for fishing gear, water toys, and boating equipment. Inside, the home welcomes you with a spacious living room on the first floor, a 2nd living room on the 3rd floor, a large kitchen, equipped with stainless steel appliances, a full bar and an elevator that services all three levels. All 4 bedrooms feature generous closet spaces, and en-suite bathrooms.

175 W Ave A, Key Largo

813 Blue Heron Ln, Key Largo
$2,649,000
3 Beds ⋅ 4 Baths ⋅ 621760 MLS
Live La Dolce Vita in Key Largo! An extraordinary opportunity to experience the ultimate in privacy, serenity, and waterfront living from this spectacular peninsula point property surrounded by expansive open-water views. This palatial 3-bedroom, 3.5-bath pool home captures breathtaking vistas from the main living level and expansive covered patios. A unique dual-house layout provides exceptional privacy, making the property ideal for multigenerational living, extended family, or guests. The sparkling saltwater pool, complete with both heater and chiller, is strategically positioned beneath the home to create a dramatic, shaded tropical retreat for year-round enjoyment. Lush lawns and mature tropical landscaping have been meticulously and professionally maintained, while a mosquito-control misting system enhances outdoor living throughout the grounds. The first level offers a private third bedroom with full bath, along with a caretaker's quarters and workshop. All living levels are constructed above the floodplain. Boaters will appreciate the floating dock system and immediate ocean access via the Pennekamp Waterway. After a day on the water, enjoy the convenience of the outdoor shower and foot wash before relaxing poolside and taking in the spectacular surroundings. The well-appointed kitchen features a Viking gas range with griddle and hood, dual-drawer dishwasher, stainless-steel bar sink, and quality finishes designed for entertaining. Additional features include two A/C systems, a metal roof, impact-resistant windows and doors, electric entry gates, and an ADT security system with cameras,providing both security and peace of mind. Private, gated, and surrounded by the natural beauty of the Florida Keys, this exceptional property is just one hour from Miami, yet feels like a private tropical world away. Live Life Deliberately in the Fabulous Florida Keys!

813 Blue Heron Ln, Key Largo

711 Olivia St, Key West
$2,895,000
3 Beds ⋅ 3 Baths ⋅ 621758 MLS
Fully restored historic 3BD/3BA with 1,600 sq ft of total living space in the heart of Old Town, with pool, private guest cottage, and off-street parking, located in X flood zone and offered turnkey. Some historic homes ask their next owners to take on a century of hidden repairs. This one asks only that you move in. With great care and pride, the owner restored the house from foundation to roof: a new foundation, new windows and siding, all-new electrical and plumbing, and every system beneath the surface brought current. The result is the character of an Old Town classic with the soundness of a home built today, and none of the worries that usually come with an older house. Inside, the main house is arranged as a 2BD/2BA, with both bedrooms ensuite, giving each occupant a private retreat of their own. Outside, the pool sets the tone for long winter afternoons in the tropical sun. Beside it, a separate 1BD/1BA guest cottage gives visiting family or friends their own quarters and bath, so everyone can share the season while keeping their privacy. Off-street parking for one car, a true premium in Old Town, makes arrivals and departures easy. The home is offered fully turnkey, with interiors curated by local designer Amie Woeppel, so a seasonal owner can arrive, unpack, and start living, with nothing left to fix or furnish. Every choice reflects an owner who restored this house to be lived in and loved, not simply sold. From the front door, Duval Street is a six-minute walk, with a wide selection of restaurants and bars along the way. Old Town history, rebuilt from the ground up and ready for its next chapter.

711 Olivia St, Key West

1017 Picard Ln, Cudjoe
$2,600,000
4 Beds ⋅ 3 Baths ⋅ 621757 MLS
Endless blue water, expansive skies, and an exceptional point setting create a memorable first impression at 1017 Picard Lane. Positioned at the end of a cul-de-sac shared by just three homes on the point, this striking waterfront residence captures the beauty of the Florida Keys with sweeping open-water views and inviting spaces to enjoy them. Offering 4 bedrooms, 3 baths, and 2,312 square feet, the home welcomes you with soaring ceilings, and a bright, airy interior. The beautifully appointed kitchen features white cabinetry, richly patterned quartz countertops, stainless steel appliances, and generous breakfast-bar seating. Beyond the living spaces, a spacious covered waterfront terrace provides an elevated vantage point for morning coffee, outdoor dining, and quiet evenings overlooking the water. Set on a 12,507-square-foot lot, the property brings outdoor living to the forefront. A concrete swimming pool overlooks the open water, while the expansive covered downstairs entertaining area offers room to gather, dine, and relax in the shade. A hot tub and enclosed outdoor shower add to the experience, creating a welcoming retreat after a day spent enjoying the Keys. A broad paver driveway, tropical landscaping, and elegant black wrought-iron fencing complement the home's impressive exterior. CBS construction, a metal roof, impact windows and doors, an elevator, and an electric-vehicle charging hookup, 5 x 32 ft Composite dock combine enduring appeal with everyday convenience. From poolside afternoons to evenings on the waterfront terrace, this distinctive property offers a beautiful setting to make the most of life on the water. Plus ''A rooftop observation deck offers an elevated retreat to take in sweeping open-water views and the beauty of the surrounding Keys.''

1017 Picard Ln, Cudjoe

29688 Forrestal Ave, Big Pine
$1,299,000
3 Beds ⋅ 2 Baths ⋅ 621755 MLS
Discover the Florida Keys lifestyle in this charming 3-bedroom, 2-bath canal-front home offering 1,928 sq. ft. of living space on an 8,000 sq. ft. lot in Big Pine Key. Situated on a quiet street with convenient boating access to both the Gulf and Atlantic Ocean, this property is ideal for those looking to enjoy life on the water. Boating enthusiasts will appreciate the 68' concrete dock with dual 5,500 lb. davits. Garden lovers will enjoy the fully fenced yard featuring lush tropical landscaping, paved pathways and a tranquil pond with a waterfall. Inside, beautiful real wood flooring flows throughout the home, bringing warmth and character to the inviting living spaces. The spacious Great Room features a wood-burning fireplace and French doors opening to a screened waterfront balcony, creating the perfect setting to relax and enjoy peaceful canal views. The Primary Suite offers a charming wood-plank ceiling, cedar-lined walk-in closet and ensuite Bath. Additional highlights include impact windows, an electric exterior elevator lift for added convenience, a covered carport and a spacious lower-level enclosure providing ample storage for fishing gear, boating equipment and more. Whether you're spending the day exploring the surrounding waters or unwinding on your screened porch, this inviting waterfront retreat offers an opportunity to embrace the laid-back Florida Keys lifestyle.

29688 Forrestal Ave, Big Pine

251 Azalea St, Tavernier
$1,290,000
2 Beds ⋅ 2 Baths ⋅ 621754 MLS
Unpack, launch the boat, and start living the Keys life. This turnkey, ground-level concrete canal home in Plantation Key Colony is ready for you. The big projects are done: a brand new metal roof, impact windows and doors, a new sewer line, fresh paint inside and out, new interior doors, and energy-efficient appliances. Even the tiki hut was just re-thatched. The 2 bed, 2 bath home is clean, bright and easy to care for. The boating setup is hard to beat. You have 50 ft of dockage on the canal and a boat slip with a ramp that runs through the pull-through garage. A new fish cleaning station with water and electric is ready for the day's catch. Run out Tavernier Creek to the ocean side, or head straight into Florida Bay. The garage has been refreshed too, with new door rollers, new lock hardware, and upgraded floors and walls. Plantation Key Colony has a voluntary HOA and a bayfront park with a boat ramp, a small beach and a picnic area. Islamorada's marinas, waterfront restaurants and world-class fishing are just minutes away!

251 Azalea St, Tavernier

31107 Ave I, Big Pine
$695,000
3 Beds ⋅ 2 Baths ⋅ 621753 MLS
Bring your vision to this spacious corner-lot stilt home on Big Pine Key! Low Assumable mortgage for qualified buyers. Just a short stroll from Big Pine Key Community Park, this 3-bedroom, 2-bath elevated home offers an open living concept, a split-bedroom floor plan, and bamboo floors throughout. The home needs some TLC and is ready for a buyer with an eye for potential to restore it and make it their own. Room to spread out is the real standout here. The property offers plenty of space for multiple cars, boats, and even an RV with hookup. Below, you'll find a 2-car garage, an outdoor shower, and generous storage space. Enjoy the true Big Pine lifestyle, where the adorable Key deer can often be seen roaming the neighborhood. A great opportunity for investors, contractors, or anyone ready to create their Keys retreat in a sought-after Big Pine location.

31107 Ave I, Big Pine

7219 Simran Ln, Duck Key
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 621752 MLS
This well appointed single-family home is located within The Sanctuary, an exclusive gated community of just 26 residences at Hawks Cay. Offering spacious indoor and outdoor living, this beautifully maintained home features a private yard, it's own swimming pool and covered carport. Coastal-inspired furnishings, cool neutral tones and large French doors create a bright and inviting atmosphere filled with natural light. Light wood-look tile flooring throughout the open-concept living, dining and kitchen areas, creating a relaxed and sophisticated Florida Keys feel. This immaculate three-bedroom, three-bath home offers a unique advantage with a full bathroom on the main level adding convenience and versatility for owners and guests. Numerous upgrades have been completed in recent years, making the property move-in ready and exceptionally well maintained. Currently operated as a successful private vacation rental with strong rental income, the home offers an excellent opportunity as an investment property, second home or combination of both. This property is on the fiber network. High speed fiber optic, internet, Direct TV included in the HOA dues. Owners may also explore participation in the Hawks Cay Resort rental program for access to resort amenities and services. Contact us for additional property details, rental history and information regarding the resort rental program.

7219 Simran Ln, Duck Key

74501 Overseas Hwy, Islamorada
$4,850,000
5 Beds ⋅ 4 Baths ⋅ 621750 MLS
Discover a rare oceanfront paradise in the Florida Keys, situated on 1.35 acres of private oceanfront property featuring an extraordinary stretch of natural sandy beach, a feature seldom found in the Keys. Perfectly positioned next to iconic Sea Oats Beach, known for its pristine shoreline and seasonal sea turtle nesting, this exceptional estate offers privacy, coastal elegance, and breathtaking turquoise waters, just minutes from Islamorada's renowned dining and shopping. Enter through a private electric gate with ample parking for vehicles, boats, and trailers, plus an oversized three-car garage with pull-through access. An expansive ground-level storage area, currently utilized as a private gym, provides additional space for recreational equipment and boating gear. Built with concrete construction, the residence features impact-resistant windows and doors, along with a 25kW propane generator. Inside, marble floors, granite countertops, stainless steel appliances, a wine refrigerator, built-in ice maker, and spectacular open living spaces create an inviting coastal retreat. Four sets of double sliding impact glass doors frame panoramic ocean views and abundant natural light. The residence features five bedrooms and four full bathrooms, including two guest suites with private baths. The oceanview primary suite offers a walk-in closet, dual vanities, soaking tub, and walk-in shower. Outside, a lagoon-style pool, Jacuzzi, and wraparound balcony create an exceptional setting for entertaining and enjoying the ocean breezes. Offered below its 2026 appraised value, this remarkable oceanfront estate presents a rare opportunity to own 1.35 acres of private oceanfront property with a natural sandy beach, stunning open-water views, and convenient access to Islamorada's restaurants, shopping, and marinas.

74501 Overseas Hwy, Islamorada

3315 Donald Ave, Key West
$1,050,000
3 Beds ⋅ 2 Baths ⋅ 621749 MLS
***Beautifully maintained, thoughtfully improved, and ready for its next chapter in Key West!*** Discover 3315 Donald Avenue, a home where quality, comfort, and island living come together beautifully! Tucked into desirable Buttonwood Court, this inviting 3-bedroom, 2-bath residence offers soaring vaulted ceilings, premier lighting, warm natural wood cabinetry, granite countertops, a spacious kitchen island, and a convenient pantry. The open, welcoming interior flows through sliding glass doors to a screened rear porch overlooking a natural wildlife area. Here, beautiful sunrises greet you from the back of the home, creating a peaceful setting for morning coffee or simply enjoying the natural surroundings. Pride of ownership is evident throughout, with thoughtful improvements, quality finishes, and inviting outdoor spaces designed for easy Key West living. Enjoy the convenience of being just minutes from Old Town's restaurants, galleries, entertainment, and waterfront attractions while returning home to a quieter neighborhood setting. With its appealing combination of location, comfort, and exceptional care, this property presents a wonderful opportunity for locals looking to put down roots or anyone ready to make Key West home. **A home that's been cared for with intention and is ready to be enjoyed from day one!**

3315 Donald Ave, Key West

1320 Eliza St, Key West
$2,399,000
4 Beds ⋅ 4 Baths ⋅ 621742 MLS
Welcome to 1320 Eliza Street, a beautiful historic Key West home filled with Old World charm and character. Once serving as a local schoolhouse, this unique property sits on a stunning, tropically landscaped corner lot in a quiet neighborhood, offering the perfect combination of history and privacy in Old Town, Key West. Featuring four (4) bedrooms, two (2) full bathrooms, and two (2) half bathrooms, this home offers plenty of space for family and guests, both indoors and out. A brand-new roof was recently installed, and the home has just been tented, providing added peace of mind. The main residence offers generous living spaces that open beautifully to the lush tropical gardens surrounding the home. The spacious living room flows directly onto a covered porch, allowing you to enjoy the wonderful Key West weather year-round. The chef's kitchen is perfect for preparing everything from a gourmet dinner to a casual meal with family and friends. The first-floor primary bedroom offers plenty of room for a king-size bed, along with a spacious walk-in closet. The second guest bedroom features its own en-suite bathroom and private front porch, giving guests their own special place to relax and enjoy the Key West lifestyle. Upstairs, you'll find a third bedroom along with an oversized walk-in storage area and ample closet space. Step outside and enjoy your own private tropical retreat. Beautiful gardens surround the heated and chilled swimming pool, creating a wonderful setting for entertaining or simply relaxing in the sunshine. Tucked away in the back corner of the property, the separate pool house offers additional privacy and flexibility, making it perfect for guests, a home office, or a quiet getaway. Complete with a half bathroom and outdoor shower, it offers what we like to call a true Key West bathroom! This home is a must see! Schedule your private showing today!

1320 Eliza St, Key West

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