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$1,699,000
3 Beds ⋅ 3 Baths ⋅ 620079 MLS
Discover the perfect blend of Florida Keys waterfront living and income potential in this fully furnished home located on a residential waterway with Gulf access in the heart of Marathon. Designed for relaxation and entertaining, the home offers comfortable living spaces, beautiful water views, an enclosed Florida room, a private pool, and a private dock. Whether you are looking for a primary residence, seasonal retreat, or investment property, this home provides the flexibility to fit a variety of lifestyles. The private dock offers convenient boating access to the Gulf, making it easy to enjoy fishing, paddleboarding, boating, and everything that makes the Florida Keys lifestyle so special. Spend your days exploring the water, entertaining by the pool, or simply enjoying the peaceful waterfront setting. A standout feature of this property is its established vacation rental success. The home is actively operating as a popular vacation rental with future reservations already on the books, providing an opportunity for immediate income generation. Buyers have the flexibility to honor existing reservations and continue the rental operation, or modify future bookings to accommodate their own plans and personal use. With its waterfront location, proven rental history, future bookings in place, and desirable Marathon location, this property offers a unique opportunity to enjoy the Florida Keys while benefiting from the flexibility of an established income producing asset. Whether your goal is full time island living, a seasonal getaway, or a property that helps offset ownership costs through rental income, this home is ready for its next chapter.

11260 6th Ave, Marathon
$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
$2,595,000
3 Beds ⋅ 3 Baths ⋅ 620076 MLS
Some homes simply arrive finished -- and this Duck Key showstopper is one of them. Dressed in modern coastal farmhouse finishes and positioned along a serene canal, it delivers the rare combination most buyers spend years searching for: a seamlessly curated interior, serious boating infrastructure, and not a single update needed. The palette flows effortlessly throughout -- soft whites, warm creams, and sun-bleached sand tones that feel both elevated and livable. The main living area commands attention with soaring vaulted ceilings, anchored by a sweeping wall of windows that frames the canal like a living painting. Step through to the expansive screened patio and the boundary between indoors and out dissolves entirely. The kitchen centers around a substantial quartz island, flanked by custom oversized cabinetry and stainless appliances. Screened enclosures at both the front and rear include dedicated storage for fishing tackle and marine gear -- because the lifestyle here demands it. And then there is the dock. At a rare ninety-three feet in length with an exceptional beam width, fully equipped with water, electric, and a 24,000-pound boat lift, this is not a recreational amenity -- it is a destination. Few properties in the Keys offer this combination of length, width, and capacity. Architectural details speak to the quality throughout: a crisp standing-seam metal roof, impact-resistant windows and doors, an oversized motor court, and intentionally low-maintenance grounds. Inside, porcelain tile floors, LED-lit vanity mirrors, a double vanity in the primary suite, oversized closets, and new plumbing and light fixtures complete a home finished with genuine care. The existing patio deck can be converted back into a future swimming pool. This is Duck Key living at its finest. Schedule your private showing today.

248 W Seaview Dr, Duck Key
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 620075 MLS
With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

1911 Seidenberg Ave, Key West
$750,000
2 Beds ⋅ 2 Baths ⋅ 620072 MLS
Experience the laid-back Florida Keys lifestyle in this beautifully maintained, double lot sized at 12,000 sq ft, concrete 2-bedroom, 2-bath stilt home located on a desirable clean swim canal in Big Pine Key. Situated at the end of the street with no through traffic, this secluded waterfront retreat offers exceptional privacy, tropical breezes, and the perfect blend of comfort and coastal living. The home sits on an ideal east-west exposure, allowing for a refreshing cross breeze throughout the property and abundant natural light from the many windows throughout the home. Step inside to discover a nicely finished interior featuring laminate flooring, granite countertops, and soft close cabinets, a spacious living and dining room area, and huge walk-in closets that provide excellent storage space. Offered fully furnished, this home is move-in ready and ideal as a full-time residence, vacation getaway, or investment opportunity. Outdoor living is truly exceptional with two large screened decks that enhance the outdoor living space, perfect for relaxing, entertaining, or enjoying peaceful canal views and tropical surroundings. Enjoy looking at the many fruit trees on the property including, papaya, mangos, dragonfruit, 2 varieties of bananas, grapefruit, lemon, Spanish limes, melon, and pineapples. The property also offers plenty of room for a pool, gazebo, or garden area, creating additional potential for your private island oasis. The fenced yard adds both privacy and security, while the clean closed canal behind the home is known for its clear water and fish, making it ideal for kayaking, paddleboarding, or simply enjoying nature. A concrete seawall with kayak launch provides direct canal access right from your backyard. Additional features include: Impact windows and doors Stair access on both sides of the house Conforming enclosed space under the home with ample room for storage, hobbies, or recreational use Ground-level garage and storage area

251 Pelican Ln, Big Pine
$2,499,000
4 Beds ⋅ 2 Baths ⋅ 620071 MLS
Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing 16,827 square feet, this CBS-built, ground-level home sits above the flood plain and offers approximately 225 feet of waterfront on two sides, deep-water dockage, and remarkably quick ocean access. Designed for comfort and effortless waterfront living, the 2,739-square-foot home features 4 bedrooms, a spacious open-concept great room, bamboo flooring, impact windows and doors, and a durable metal roof. The chef's kitchen is the heart of the home, offering a large center island, stainless steel appliances, abundant cabinetry, and a wine refrigerator and is the perfect gathering place for entertaining family and friends. Step outside to a beautifully landscaped tropical setting with expansive screened lanai overlooking the water and an 82-foot dock complete with boat lift and kayak launch. Whether you're heading offshore for a day of fishing, enjoying sunset cruises, or simply relaxing by the water, this property delivers the Keys lifestyle you've been dreaming about. The 2- car Garage offers plenty of parking and room for all or your toys while the oversized double lot provides privacy and space to enjoy the outdoors while taking advantage of the home's unique corner-like waterfront setting. Located in one of the Lower Keys' most desirable boating communities, Cudjoe Gardens offers deep-water canals capable of accommodating larger inboard vessels, plus convenient access to a full-service marina with fuel, bait, boat ramp, refreshments, and a waterfront restaurant. Just 20 minutes from Key West, you'll enjoy world-class dining, entertainment, and island living while returning home to a peaceful waterfront retreat.

21023 2nd Ave, Cudjoe
$13,500,000
8 Beds ⋅ 8 Baths ⋅ 620067 MLS
Private Helicopter Estate in the Florida Keys. Behind private gates on prestigious Million Air Row, this exceptional oceanfront estate spans nearly 2.5 acres and offers a rare blend of luxury, privacy, and future potential. The recently renovated residence features 8 bedrooms, 7.5 bathrooms, double-height ceilings, spacious bedroom suites, abundant storage throughout, solid CBS construction, impact windows and doors, and a new concrete roof. Designed for the ultimate Florida Keys lifestyle, the property boasts protected basin dockage with a 24,000 lb boat lift, a private helicopter pad, hot yoga studio, resort-style pool with waterslides, waterfall, and spa, plus two covered carports and a large garage. Expansive grounds provide endless opportunities to add additional amenities such as pickleball, volleyball, guest accommodations, or a private beach retreat. A truly unique waterfront compound offering the space and exclusivity rarely found in the Florida Keys.

89401 Old Hwy, Tavernier
$750,000
4 Beds ⋅ 2 Baths ⋅ 620060 MLS
Nestled in the heart of highly desirable Largo Sound Village, this beautifully maintained 4-bedroom, 2-bath CBS home has the perfect blend of Florida Keys charm, boating lifestyle, and true neighborhood community living. Largo Sound Village is known not only for its private waterfront amenities, but also for its warm, family-friendly atmosphere where neighbors come together throughout the year to celebrate holidays, decorate for the seasons, and create a welcoming sense of community that is hard to find in the Keys. Represented buyers are encouraged to inquire. Residents enjoy access to the neighborhood's private homeowner's park for just $150 per year, featuring a boat ramp, trailer parking, tiki hut, and dog park, along with quick boating access to both the Atlantic Ocean and Florida Bay through Adams Cut. Whether it's evening golf cart rides, holiday gatherings, or spending weekends on the water. Inside, the home features 2,283 square feet of inviting living space filled with natural light. The updated kitchen includes stainless steel appliances, Silestone countertops, extensive prep space, and bar seating for entertaining family and friends. The spacious living area flows seamlessly into a fully enclosed and air-conditioned Florida room, creating the perfect space for relaxing or hosting guests year-round. From the backyard, enjoy peaceful water glimpses and the calming sounds of Largo Sound nearby. The primary suite includes a private ensuite bath with a large walk-in shower, while three additional newly carpeted bedrooms provide flexibility for family, guests, or a home office. One bedroom currently used as an office has a separate exterior entrance and could easily be converted into an in-law suite with room to add a third bathroom. Situated on a fully fenced 6,000 sq. ft. lot, the property has plenty of parking plus room for a future pool or tiki area. A 240V fast charger is already installed.

304 2nd Ter, Key Largo
$1,245,000
2 Beds ⋅ 2 Baths ⋅ 620053 MLS
Just minutes from Key West, this open floor plan waterfront home has 2 bedrooms and 2 with bonus room can easily be converted to a 3-bedroom layout. Enjoy open water views and a rare sense of privacy with no homes on the open water side of the street. The deep-water canal features an 80' concrete seawall with quick access to both the Gulf and Atlantic via Waltz Key Basin, with room for large boats. Expansive wraparound decking captures breathtaking sunrises and bayfront sunsets from this oversized 8000 sq ft lot. Features include bamboo and wood grained porcelain tile flooring, upgraded expansive kitchen with KitchenAid appliances, covered porch, screen room, fenced yard, fish cleaning station, tropical landscaping, workshop, large A/C storage area, impact windows and accordion shutters. Low homeowners insurance $1,082 annually. Easy and fun to show so don't miss this one! Owner is a Licensed Florida Real Estate Agent.

24 Tamarind Dr, Big Coppitt
$1,595,000
2 Beds ⋅ 3 Baths ⋅ 620047 MLS
Beautifully renovated corner-lot home in the heart of Casa Marina. This 2-bedroom, 2.5-bath residence sits on a 4,331 sq. ft. lot with room for a pool and offers a seamless blend of modern updates and classic Key West charm. Highlights include wide-plank wood floors, a bright all-white interior, and a designer kitchen featuring custom cabinetry, La Cornue gas range, paneled dishwasher, wine cooler, Quartz island, and subway-tile backsplash. The living room boasts built-in bookshelves and flows into a flexible study/home office. Multiple sets of French doors open to a covered front porch, outdoor dining area, and private wraparound porch. The primary suite offers custom wardrobes and a luxurious marble ensuite with soaking tub, glass-enclosed shower, and nickel fixtures. Guest bedroom with ensuite bath, dedicated laundry area, and stylish powder room complete the layout. Steps to Duval Street, Higgs Beach, Edward B. Knight Pier, waterfront dining, dog parks, and tennis/pickleball courts. A rare offering in one of Key West's most desirable neighborhoods.

1401 Grinnell St, Key West
$785,000
2 Beds ⋅ 1 Baths ⋅ 620040 MLS
Experience the laid-back Florida Keys lifestyle in this beautifully updated, turn-key canal-front retreat, nestled in the quiet Eden Pines neighborhood among the roaming Key Deer. Situated on a 50-foot concrete seawall with step-down access, fish cleaning station, and a new boat lift, this property offers excellent boating access to both the ocean and bay. Inside, the open concept living area is filled with natural light and designed for comfortable island living, boasting high exposed-beam ceilings, adding character and depth to the space. The spacious kitchen features solid wood cabinetry, while recent updates to the bathroom, bedrooms, and bedroom flooring give the home a fresh coastal feel. A large pocket sliding glass door disappears into the wall, creating seamless indoor-outdoor living and opening to an expansive covered back porch measuring approximately 36' x 12', perfect for entertaining, dining, or relaxing canal-side. New composite decking and front porch railings were completed in 2024, adding durability and style, and additional updates include a new HVAC system, new tankless water heater, new siding, and new impact windows throughout. The primary suite offers walk-in closets and direct porch access, while the laundry area is conveniently located on the back balcony. Offered with new furnishings both inside and out, this move-in-ready Keys getaway is ideal as a full-time residence, vacation home, or investment opportunity. Don't miss the opportunity to check out this Big Pine Key gem!

29034 Rose Dr, Big Pine
$1,049,000
4 Beds ⋅ 3 Baths ⋅ 620041 MLS
This newly built 2026 home on Stock Island delivers what buyers rarely find in the Florida Keys: true new construction, built to current code, with a fully legal guest suite and insurance costs designed to be as manageable as possible -- all priced under $1.1M. The main residence offers 3 bedrooms, 2 bathrooms, and over 1,500 square feet of thoughtfully designed living space elevated 18 feet above grade. Interiors feature waterproof and scratch-proof luxury vinyl plank flooring, quartz countertops, stainless steel appliances, and in-unit washer and dryer. HardiePlank siding, impact-rated doors and windows, and a metal roof complete a build package engineered for Keys living. Central air conditioning keeps the main home comfortable year-round. The elevated guest suite -- positioned at 9 feet with its own private entrance below the main home -- adds one bedroom, one bathroom, and approximately 500 square feet of additional living space, complete with quartz countertops, stainless steel appliances, in-unit laundry, and a mini-split system. Live in one, rent the other, or house extended family with total privacy. Similar properties are bringing in over $6500 per month in rent. The fully fenced, rock-covered lot provides covered parking under the home and additional off-street parking out front -- a genuine premium in the Keys. Stock Island puts you one bridge from Old Town Key West, with marinas, restaurants, and the energy of the Keys right at your door.

49g Miriam St, Stock Island
$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
$899,000
3 Beds ⋅ 2 Baths ⋅ 620038 MLS
This is the perfect CBS elevated property, ideally located in the neighborhood of Port Largo, one of the most sought after neighborhoods in the Keys. With something for everyone within walking distance, this home offers the ideal blend of comfort, convenience, and Florida Keys living. Whether you're looking for a blank canvas to create your dream home or want to enjoy the high quality finishes already in place, this property delivers. The interior features timeless materials that are making a strong comeback with the popular ''Tuscan 2000s'' aesthetic. The low maintenance landscaping makes it easy to envision your perfect outdoor oasis, with plenty of space to create an entertaining area, tropical retreat, or poolside paradise. The home also includes solar on the roof for the hot water heater, helping improve efficiency and reduce utility costs. Residents of Port Largo enjoy access to a private boat ramp, Jacob's Aquatic Center, the Port Largo Homeowners Park, and so much more. Owner is currently moving out, and the house will be vacant soon.

107 Marina Ave, Key Largo
$2,100,000
3 Beds ⋅ 2 Baths ⋅ 620036 MLS
Welcome to 499 Avenida Primiceria in Marathon FL. This unique home is perfectly located just 7 houses from beautiful Sombrero Beach and only minutes away from open water for boating. Enter into the central hub of the home that offers cathedral open beam ceilings and a generous, updated open floor plan for common living areas and direct access to the screened porch that overlooks the pool and dock. The split floor plan for the bedrooms offers additional privacy with the Primary suite located in the opposite wing from the guest rooms. Everything has been updated from the plank tile flooring, the impact resistant windows and doors, the open custom kitchen and update bathrooms. There is a while house generator. The lower level hosts a garage, workshop, covered entertaining area, and tons of additional storage space. The custom concrete pool is heated and chilled and the dock is 100' of concrete seawall with a 14k lb. boat lift. The grounds are covered with pea rock and mature tropical landscaping making for ease of maintenance and a lush private tropical setting. Call today for more information and schedule your private tour of this wonderful Florida Keys retreat.

499 Avenida Primiceria, Marathon
$1,245,000
3 Beds ⋅ 3 Baths ⋅ 620031 MLS
Beautifully maintained Golf Club home overlooking the 17th hole in the Sanctuary. This home is located on one of the largest lots in the development. New flooring upstairs, a new cooktop stove, a new kitchen sink, new light fixtures, and freshly painted exterior within the past 3 years. The home features a private carport for two vehicles and a detached storage unit. The Key West Golf Club community features two gorgeous pools surrounded by lush tropical landscaping, a gym at the clubhouse, on-site security and managers. Property is currently being leased.

243 Golf Club Dr, Key West
$1,245,000
4 Beds ⋅ 3 Baths ⋅ 620026 MLS
Experience the best of Florida Keys waterfront living in this stunning 4-bedroom, 3-bath home located in the highly desirable Vaca Cove community. Offered fully furnished and turnkey, this elevated residence features a spacious open-concept design with large bedrooms, wide hallways, and inviting indoor-outdoor living spaces designed for comfort and entertaining. Boaters will appreciate 35 feet of dockage and quick, deep-water access to both the Atlantic Ocean and Gulf of America through Vaca Cut. Vaca Cove is an intimate enclave of only seven homes built in 2016, centered around a private lagoon marina and resort-style swimming pool. The lagoon seawall is ideal for launching kayaks and paddleboards, adding to the laid-back island lifestyle. Fully licensed for vacation rentals with bookings already in place, this property presents an outstanding opportunity for investors or buyers seeking an easy-care second home with strong rental potential. Constructed for durability and peace of mind, the home includes a metal roof, impact-resistant windows and doors, covered parking, hot tub area, and ample storage for vehicles and boat trailers. Beautifully maintained and move-in ready, this exceptional waterfront retreat offers luxury, convenience, and income potential in one of Marathon's most unique waterfront communities.

12555 Overseas Highway Unit F, Marathon
$675,000
2 Beds ⋅ 3 Baths ⋅ 620025 MLS
Located just 10 miles from Key West, this 2 story elevated home is the perfect space for full time living or a second home get away. This beautifully maintained 2 bedroom, 2.5 bath modular home offers the perfect blend of comfort, durability, and low-maintenance Florida Keys living. Situated on a fully fenced lot with artificial turf for year-round curb appeal and easy upkeep, the property is ideal as a full-time residence, vacation retreat, or second home investment. Built for peace of mind, the home features a metal roof along with all impact-rated windows and doors, helping keep insurance costs lower while providing excellent storm protection. The elevated design offers covered parking and storage space below, plus an exterior shed for all your tools, bikes, fishing gear, and island toys. Inside, you'll find a bright and inviting layout with spacious bedrooms, open living areas, and a functional floor plan designed for relaxed Keys living. Enjoy the convenience of being just minutes from Key West while still having the privacy and laid-back atmosphere of the Lower Keys. Whether you're looking for a low-maintenance primary home or the perfect island getaway, this property checks all the boxes.

59 Ed Swift Rd, Big Coppitt
$3,495,000
4 Beds ⋅ 4 Baths ⋅ 620024 MLS
OCEANFRONT , POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water living at this exceptional oceanfront retreat in the exclusive community of Summerland Cove, just 30 minutes from Key West. Designed for serious boaters and lovers of open water, this premier deep-water home offers breathtaking Atlantic views, immediate boating access, and the ultimate Florida Keys lifestyle. Beautiful newly painted exterior, this elevated 4 bed 3.5 bath home offers 2,766 sq. ft. of beautifully designed living space where soaring ceilings and walls of glass frame endless turquoise water views. Rare 3 bedroom suites with ensuite bathrooms, and a 4th bedroom with ensuite half bath. The expansive open-concept living and entertaining areas create a seamless indoor-outdoor flow perfect for relaxing or hosting guests after a day on the water. Separate laundry room is a bonus. A rare concrete dock with a protected cut-in boat slip provides quick deep-water access to the Atlantic with no long canal commute--placing you minutes from world-class offshore fishing, reef diving, sandbars, and endless boating adventures. Step outside to your private oceanfront oasis featuring a sparkling pool and spa, expansive lounging decks, and a poolside kitchen designed for sunset entertaining and waterfront gatherings. Panoramic open-water views and ocean breezes create the perfect Keys atmosphere. Upstairs, the spacious primary suite offers stunning ocean views, a private balcony, and a peaceful retreat overlooking the Atlantic. Additional features include impact windows and doors, a metal roof, a chef's kitchen with granite countertops and stainless steel appliances, plus convenient access to the nearby Summerland Key Cove Airport for easy fly-in/fly-out travel in light aircraft. This rare offering combines luxury living, protected deep-water dockage, immediate ocean access, and unforgettable open-water views in one of the Florida Keys' most sought-after waterfront communities.

414 E Caribbean Dr, Summerland
$1,245,000
4 Beds ⋅ 3 Baths ⋅ 620023 MLS
Nestled within the exclusive waterfront enclave of Vaca Cove, this beautifully furnished 4-bedroom, 3-bath elevated home offers the perfect blend of luxury, comfort, and investment potential. Designed with an expansive open floor plan, wide hallways, and generously sized bedrooms, the home is ideal for entertaining and relaxed coastal living. Enjoy 35 feet of private dockage with easy, deep-water access to both the Atlantic Ocean and Gulf of America via nearby Vaca Cut. Built in 2016, Vaca Cove is a private community of just seven single-family homes surrounding a tranquil lagoon and resort-style pool. The lagoon seawall provides the perfect launch point for kayaks and paddleboards. Fully licensed as a vacation rental with future bookings in place, this turnkey property is being sold beautifully furnished and rental ready. Additional features include covered parking, room for multiple vehicles and boat trailer storage, hot tub area beneath the home, metal roof, and impact windows and doors designed to maximize insurance savings. Whether you're seeking a proven income-producing property, second home, or full-time island retreat, this exceptional Vaca Cove residence delivers effortless Florida Keys living.

12555 Overseas Hwy Unit C, Marathon
$26,400,000
7 Beds ⋅ 10 Baths ⋅ 620022 MLS
Escape to Palm Paradise, a breathtaking oceanfront estate on 7.64 private acres in Islamorada, offering 369 feet of shoreline and sweeping Atlantic views. Tucked behind gates on Plantation Key, this secluded retreat combines lush tropical landscaping with unmatched privacy for the ultimate island escape. The 8,988-square-foot main residence showcases exceptional craftsmanship and thoughtful design. One wing features a dramatic two-story primary suite with a private office, while the opposite wing includes four additional bedrooms and four bathrooms across two levels. A separate two-bedroom guest house provides extra space for visitors, and a whole-house generator adds convenience and peace of mind. Inside, custom woodwork, coffered ceilings, built-ins, and high-end finishes create a warm yet refined atmosphere. Amenities include a chef's kitchen, wine cellar, private gym, elevator, and seamless indoor-outdoor living spaces ideal for entertaining or relaxing by the water. Resort-style outdoor features include a custom pool, tiki bar, outdoor kitchen, beachside fire pit, putting green, observation pier, and a lighted tennis court with cabana. Convenient access by seaplane, helicopter, or a 90-minute drive from Miami makes travel effortless. Perfect for boating enthusiasts, the estate is near dockage and concierge dry storage options. Located in the heart of Islamorada, Palm Paradise offers easy access to world-class fishing, boating, dining, and the laid-back luxury of the Florida Keys. Offered at $26.4M, Palm Paradise is a rare opportunity to own a private waterfront compound ideal for luxury living, family retreats, or executive escapes.

89505 Old Hwy, Tavernier
$1,199,000
3 Beds ⋅ 3 Baths ⋅ 620017 MLS
Nestled in the heart of Big Pine Key, this private canal-front retreat with screened in POOL offers the perfect blend of comfort, space, and island living. Situated on an oversized 21,438 fenced in corner lot with a private gated entrance, the property provides exceptional privacy and a peaceful setting surrounded by tropical beauty. Plenty of space for your RV, Boat Trailer and more. It's a boaters dream. Access the Atlantic or Gulf in minutes. 15,000 lb. Boat lift added in 2024. Inside, the home features 1,774 square feet of thoughtfully designed living space with 3 bedrooms and 3 bathrooms. The third bedroom has a private entrance and could be used as guest quarters or an in-law suite. The updated kitchen showcases modern finishes and functionality, while the beautifully renovated bathrooms reflect today's contemporary style and comfort. Spacious living areas and an inviting layout create an ideal environment for both relaxing and entertaining. Impact Windows and Doors. New AC year 2026. Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this canal-front property offers the privacy, upgrades, and Florida Keys lifestyle buyers are searching for. Call to schedule your private tour. Sellers are motivated.

30525 Winifred St, Big Pine
$1,249,000
3 Beds ⋅ 2 Baths ⋅ 620013 MLS
Welcome to this beautifully renovated 3-bedroom, 2-bathroom home that perfectly blends modern finishes with warm, inviting living spaces. From the moment you arrive, you'll love the charming curb appeal, spacious covered front porch, and bright, airy interior filled with natural light. The heart of the home is the stunning chef's kitchen featuring an oversized quartz island, custom white shaker cabinetry, stainless steel appliances, abundant storage, and sleek designer finishes throughout. The open-concept layout flows seamlessly into the living and dining areas, making it ideal for entertaining and everyday living. The bedrooms offer comfort and flexibility, and both bathrooms have been thoughtfully updated with clean, modern touches. Located in a desirable neighborhood close to schools, shopping, dining, and local amenities, this move-in-ready home offers the perfect combination of style, comfort, and functionality.

2116 Fogarty Ave, Key West
$799,000
3 Beds ⋅ 2 Baths ⋅ 620011 MLS
It's your lucky day! The last buyers had to cancel their contract for personal reasons prior to inspections. Whether you enjoy fishing and diving or prefer kayaking and paddle boarding through the beautiful waters of the Lower Keys, this updated 'Old Keys' home offers the perfect base for quick access to Bogie Channel, the Atlantic, and the backcountry. Situated on a 50' x 100' lot, the 2-story, single-family residence features a cut-in boat slip with a boat lift beneath the expansive great room, along with its own boat ramp on the side. The frame with stucco upstairs offers 1,380 square feet of living space with 2 bedrooms, 1 bath, and a spacious great room with impressive water views. The original structure has high cathedral ceilings with wood beams and beautiful hardwood floors. Generously-sized, the updated kitchen includes abundant cabinet space, granite countertops, and a large island. The CBS ground level has a grandfathered-in, 600 sq. ft. living area that provides the 3rd bedroom and 2nd bathroom creating an ideal in-law suite; plus 300 sq. ft. devoted to storage as well as the washer and dryer. Impact-resistant windows were installed upstairs in 2021, and new ductless AC/heat systems were added both upstairs and downstairs in 2022. Panel shutters protect the downstairs jalousie windows. Please note that the upstairs and downstairs living areas are not connected by an interior staircase. This long-established neighborhood is also home to local favorites and landmarks including the No Name Pub, No Name Bridge, and the Old Wooden Bridge Resort and Marina with boat ramp. Sellers would appreciate post-closing occupancy of 30-60 days.

30937 Baileys Ln, Big Pine
$949,000
3 Beds ⋅ 2 Baths ⋅ 620010 MLS
Rare opportunity to own a half-acre corner parcel in the heart of Plantation Key. With an existing structure already in place, the property offers the flexibility for an extensive renovation or full redevelopment into a custom home with room for a pool, garage, outdoor entertaining areas, boat and RV storage, and additional parking. The bayside homeowner's park and boat ramp provide direct and easy access to some of the best boating and fishing in the Florida Keys, including nearby backcountry waters, sandbars, and sunset cruises. Centrally located near restaurants, shopping, marinas, and everyday conveniences, this property not only offers an ideal Plantation Key location, but also a rare opportunity to own a large parcel with redevelopment potential in the Upper Keys.

156 Monroe Dr, Tavernier
$579,500
3 Beds ⋅ 2 Baths ⋅ 620009 MLS
Immaculate 3 Bedroom, 2 Bath home located just South of John Pennekamp park with the best Boat ramp, as well as enjoying this undersea park with amazing coral reefs and marine life with activities for the family like snorkeling, diving, and the glass-bottom boat. This is a family friendly neighborhood. This modular home is beautifully maintained and is fully furnished and thought\fully updated, with new kitchen cabinets, appliances, and new flooring, plus a durable metal roof. Enjoy the privacy of an X Flood location, and a spacious backyard with a dedicated outdoor grilling area. Ideal for family gatherings or relaxing evenings. Priced to sell quickly, this turnkey home offers both comfort and convenience in one of the Key's most desirable locations.

802 Madrid Rd, Key Largo
$750,000
4 Beds ⋅ 2 Baths ⋅ 620003 MLS
Experience the charm of Florida Keys living in this beautifully maintained home situated on an expansive 8,775 s/f lot. Offering 4 bedrooms and 2 bathrooms within 1,664 s/f of living space, this property combines comfort, durability, and modern convenience. Designed for peace of mind, the home features impact windows and doors, a durable metal roof, and an elevated A/C unit approximately 3-4 years old. Inside, you'll find easy-to-maintain tile flooring throughout, creating a bright and functional living environment. The property is also equipped with preparation for RV installation and an electric vehicle charging station, making it ideal for today's lifestyle needs. Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this Florida Keys property offers space, upgrades, and island living in a prime setting.

35 Atlantic Dr, Key Largo
$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
$1,295,000
3 Beds ⋅ 2 Baths ⋅ 620002 MLS
Homes offering this level of detail, space & modern construction are a rare find in the Lower Keys. Built in 2023 in desirable Pine Channel Estates, this exceptional waterfront home offers 75' of dockage on a deep, wide canal with quick access to Pine Channel. Tucked in far enough to avoid traffic noise, yet moments from open water, the location delivers the best of the Lower Keys lifestyle. Bonus-Low insurance costs! Designed with both luxury & functionality in mind, this split floorplan home showcases extensive upgrades & designer finishes throughout including crown custom built-ins, crown moulding, recessed LED lighting, upgraded designer fixtures, impact windows & doors, & durable Hardie board siding. The stunning kitchen serves as the centerpiece of the home with quartzite countertops, custom cabinetry, premium finishes & abundant space to gather and entertain, while quartzite carries through the bathrooms for a cohesive upscale feel. The expansive upstairs screened lanai creates an ideal indoor/outdoor living space with designer details throughout and plenty of room to relax, dine & entertain year-round. Downstairs offers expansive covered entertaining areas, outdoor shower, hot tub & 300 sq ft enclosure perfect for storage, tackle room, gym, workshop or additional flex space. True laundry/utility room adds practicality rarely found in Keys homes. Custom closet built-ins throughout. Additional features include a cistern (not currently in use), exceptional indoor & outdoor living space, & a beautifully designed waterfront setting built for boating, entertaining & enjoying the Keys lifestyle. The clear canal water here is a standout rarely found elsewhere. Double framed dock for boat lift. Homeowners/Windstorm=$2,645. Flood=$2,164

29663 Saratoga Ave, Big Pine
$3,400,000
5 Beds ⋅ 4 Baths ⋅ 620001 MLS
A premier transient investment opportunity and a genuinely enchanting way of living meet on Atlantic Boulevard! The Atlantis House is a property with heart and soul. Just steps from the beach, this compound features 5 bedrooms and 4 bathrooms across three beautifully curated living spaces with a stunning boho-coastal aesthetic. The primary residence is an exquisite 3-BR/2-BA monthly rental boasting a light-filled, open-concept floor plan for effortless island entertaining. You are welcomed into a mosaic-tiled foyer featuring whimsical swinging hammock chairs and a charming custom scooter coffee bar, flowing into spacious living areas adorned with timeless terrazzo floors. The heart of the home is a true gourmet kitchen, featuring a large island, pristine white quartz countertops, and separate Sub-Zero refrigerator and freezer. The main level offers two luxurious bedrooms opening to a beautifully landscaped fenced yard with a bistro patio. A spiral staircase leads upstairs to a third bedroom--a spectacular oasis with open water views. This level features dual sliding doors opening onto a magical, Trex rooftop terrace with a dining pergola and views of the Atlantic. It is the perfect perch to watch the sunrise with coffee in hand and return for the sunset. Around the corner are two detached, transient-licensed 1BR/1BA guest suites with dedicated parking. Both offer tasteful decor and private access to a backyard oasis with a large shared deck shaded by towering palms. Live the ultimate Key West lifestyle, a stone's throw from launching your kayak at the beach and a one-minute walk from the iconic White Street Pier. The Atlantis House conveys with its own house-made Atlantis Key Lime Pie recipe, passed from the former owner to the new owner, a tradition carried for more than 30 years. A one-of-a-kind treasure!

1401 Atlantic Blvd, Key West