Florida Keys Homes on the Bay / Gulf Side of the Island For Sale

Discover your dream surfers cottage on a tropical island! Built in 1918, this charming home still showcases elements of its historic architecture, blending timeless character with a unique coastal vibe. Located at 1020 Fleming Street in the Historic Seaport area of Old Town Key West, youll be just a short walk from amazing restaurants, great bars, and some of the best fishing and diving charters in the world.This rare gem has not been available on the market for nearly two decades and appears on the Key West map of 1848--dont miss the opportunity to make it yours. Start living your dream today. Call now!

Welcome to your slice of paradise in Islamorada! This stunning canal-front property offers direct bay access and quick, convenient ocean access, making it a boaters dream. Concrete home boasts 5 bedrooms, 3.5 baths - 2,779 sq of elegant living. Upstairs features 3 spacious bedrooms, 2baths plus powder room,. Two separate living areas upstairs provide ample space for relaxation and entertaining. The designer kitchen with generous chefs pantry is perfect for culinary enthusiasts, while the Chicago brick pavers add timeless charm.The ground level features a permitted, private 2-bedroom, 1-bath mother-in-law suite, ideal for guests or extended family. Outside, the private, lushly landscaped yard is adorned with fruit trees, creating a serene oasis. With its unbeatable location, abundant storage, and exceptional features, this home is a rare gem in the heart of the Florida Keys.Dont miss this opportunity to enjoy the best of waterfront living in Islamorada!

Plantation Key Colony - Completely UPDATED-Like New - 2/1 up and 1/1 down, Plus -2- more Bonus Room- Great to Live in or Great for Renting out Half and using the other half or making it a Double rental income. Large Concrete Dock 75 Ft. w/ 20,000lb Boat Lift. This Big Lot is 125x75 with a Tiki Hut & Hot Tub. Quick Direct access to Bay & Ocean. Beautiful Homeowners Park on the Bay with a Beach & Boat Ramp. Plenty of room for a new pool. Centrally located near Shopping, Schools, Restaurants and more.

15,500 SQ. FT. DOUBLE LOT in desirable Pine Channel Estates - bordered by areca palms providing a bit of privacy, the corner property offers an impressive 125 ft. of concrete seawall with a step-down dock and davits, and 20 ft. of concrete seawall across the end of the canal. The CBS home sits approximately in the middle providing elbow room all around - theres plenty of space for adding a pool, parking an RV, boat trailer and more. A huge, screened porch across the back overlooks the canal; 16 ft. pocket sliders open from the great room to the porch for extended outdoor living. 1444 sq. ft. of living area, 2BD/2BA with the potential to add a 3rd bedroom. Additional features include a convenient walk-around porch, covered parking, attractive paver drive, storage enclosure, metal hip roof. Excellent boat access to the ocean or back country for fishing and diving, and its a short boat ride across Pine Channel to the dock at Kikis Sandbar & Grille for lunch or dinner and music. Gorgeous sunsets can be enjoyed nightly as one looks down the length of the clean, deep canal. Add your personal touch and updates to create your exceptional piece of Keys paradise! Just 30 miles to Key West.

This one puts the FUN in FUNKY! One-of-a-kind opportunity to own a canalfront concrete 2/2 house with a concrete dock and seawall that wraps around the end of the canal and connects to the continuous dock and seawall of your extra half lot across the canal! Be the king of the canal end with this unique spot that offers so many cool combinations of different ways to create your own Florida Keys fun-filled paradise. Theres already a shady tiki hut on the half lot and plenty of extra parking for your toys and trailers. Thoughtfully planted and mature tropical landscaping provides lots of privacy on both sides and a large carambola star-fruit tree is loaded and ripe for picking! The concrete home is a 2/1 upstairs and has grandfathered living space downstairs with an updated full bath and large party porch for entertaining. Theres also a voluntary association you can join for access to the neighborhood homeowners park with boat ramp. The possibilities are endless... this ponderosa property stretches across the canal expanding your options to make this unicorn your very own! Call today... this Grand opportunity wont last!

Fabulous new waterfront home in the exclusive Buccaneer Point Estates. Come enjoy the fresh breezes and the wide-open stunning views from the large, covered terrace. Transparent railings allow for the calming view to also be fully appreciated from inside the home. This spacious home features high end detailing throughout. Solid concrete construction, Metal Roof with secondary water shield and Impact windows/doors allow for peace of mind. The home offers designer oversized porcelain flooring throughout and decorator selected fully tiled baths including the walls of the dry areas. The lighted mirrors give an elegant touch. Additionally, this home has a very roomy feel with soaring volume ceilings and 8-foot-tall door openings. The open floor plan concept is not reduced by the dining area which has its own oversized separate space and double high ceiling. The walk-in pantry and wine cooler counter are also separate. Space will never be a problem as the enormous ground floor covered exterior area allows for many vehicles to be stored in addition to plenty of room for a separate Bar-B-Q party area. The 11,000 square foot lot will comfortably accommodate a future pool, deck, and much more. (Virtual depiction of a pool and furniture are artist renderings. Not included in the asking price)

Discover unparalleled Keys living at 190 Gulfview Dr in Islamoradas exclusive White Marlin Beach. This exquisite 4-bedroom, 3-bath home boasts 70 feet of private dockage with seamless access to both ocean and bay waters. Enjoy a sparkling pool with covered entertainment space, an expansive upstairs balcony, and abundant storage for your gear. The additional downstairs living area offers extra flexibility, perfect for guests. With private access to White Marlin Beach, youll be steps from pristine sands and breathtaking sunsets. This property offers exceptional rental history with repeat guests and strong cash flow which make this an outstanding investment. Embrace luxury island living at its finest!

Open Water - Beautifully remodeled home...All systems updated and interior complete remodel done. Concrete pilings are in great condition; work just completed by a licensed contractor. This is an incredible opportunity to own a piece of nature in the Florida Keys! Privacy abounds on 1.65 acres of beautifully preserved, natural habitat, nestled on the open water with great boating and amazing views from every room in the house! Seller just trimmed trees to allow more access to the gorgeous open water views! Completely remodeled, this 3 bedroom 2 bathroom home has clean lines and architecturally gorgeous open concept living. Stainless steel appliances, quartz countertops, pantry, breakfast nook, bar area, open dining room, several seating areas, fireplace and gorgeous views from all angles! This home has handicap accessibility including a new full-size elevator, custom master en-suite and open floor plan for easy access. Impact widows and doors, 2-car garage, 20,000 gallon cistern (with public water available if you would like), large storage/entertaining area, path to the dock that has Ipe wood and a 3,000 pound boat lift that can be upgraded to your needs... all on the open water. Great boating access to the gulf or ocean. Owner has repaired columns, trimmed trees to open up the view and is connected to public sewer. This house is truly unique and just waiting for its new owner! Property is virtually staged. Nature Lovers Paradise!

Stunning Waterfront New Construction in the Florida Keys - 413 Bowie LaneExperience the best of island living in this brand-new, waterfront home in the Florida Keys! Located at 413 Bowie Lane, this modern 4-bedroom, 3-bathroom property offers everything you need for relaxation and adventure. Enjoy breathtaking water views from your spacious living areas, dive into your private pool, or park your boat at the 40-foot dock just outside your door. With a convenient storage room and luxury finishes throughout, this home is the perfect blend of comfort and coastal charm. Dont miss your chance to own a slice of paradise!

Your Slice of Paradise in the Florida Keys!New to the market, this beautifully updated 3-bedroom, 3-bath canal-front pool home in Indian Waterways offers stunning canal views, ultimate privacy, and is ready for your summer getaway.Designed for effortless Keys-style entertaining, this home features 60 feet of concrete dockage on a wide, deep-water canal with direct access to Florida Bay. The fully fenced backyard is a private oasis with a newly built pool with heater, pavers, and turf for easy maintenance. Additional upgrades include a turnkey ice maker, BBQ grill, and a brand-new 15,000-pound boat lift.The inside will take your breath away with the open-concept layout and separate guest suite! This home is filled with natural light, modern updates, and island vibes, featuring:- Vaulted Ceilings & an open layout- A state-of-the-art kitchen with a large island, custom cabinetry, and stainless-steel appliances- Impact windows and doors- Metal roof- Updated flooring throughout- Two spacious bedrooms and two updated baths upstairs- A guest suite downstairs with a separate entrance, living room, wet bar, and completely remodeled for comfort and styleLocated in Plantation Key, this home is just minutes from top-rated schools, shopping, and trendy new local restaurants known for amazing food, drinks, and unforgettable sunsets. As an Islamorada resident, enjoy exclusive access to Founders Park with its beach, boat ramp, and dog park. Neighborhood, Indian Waterways, also offers an HOA park and private boat ramp for a small annual fee! Call today!

Welcome to White Marlin -- a true fishermans paradise! Step into this beautiful 3-bedroom, 3-bathroom coastal retreat, featuring an open-concept design perfect for relaxing or entertaining. The expansive kitchen with tile countertops offers ample space, and the screened-in balcony lets you enjoy serene views without interruptions. Outside, youll find a 60-foot concrete dock and boat ramp, ideal for fishing enthusiasts, and a refreshing pool to cool off after a day on the water. With a propane backup generator for peace of mind, youre ready for any occasion. Unwind on your private beach and savor breathtaking sunsets over turquoise waters -- a slice of paradise awaits you here!

Waterfront Paradise in Tropical Bay EstatesExperience luxurious open-water living in this beautifully remodeled home overlooking the stunning Bogie Channel. Wake up to breathtaking sunrises, enjoy magical moonlit waters, and explore world-class fishing and lobstering right from your 75-foot seawall with an 8-foot-deep boat slip.This 2,000 sq. ft. open-concept home features water views from nearly every room, a serene primary suite with private sitting area, and a chefs kitchen with a 4x8 granite island. The Florida room offers panoramic vistas, while the lush backyard boasts a pool, grassy space, and visits from Key Deer.With impact windows, shutters, a new metal roof, and a 2019 remodel, this home is move-in ready and perfect as a family retreat or high-end rental. Call today for your private showing! B&BATVAI

PRE-COMPLETION PRICING AVAILABLE! Exquisite New Construction Home scheduled for completion in early 2025! Discover luxury living in this coastal haven. Boasting CBS construction, metal roof, impact windows & doors throughout. This 4 bedroom, 3 bath home is the epitome of modern elegance and coastal charm that boasts over 4,400 sq. ft of finished interior & exterior luxury! Step inside to be greeted by a beautiful, upscale kitchen featuring stainless steel appliances, shaker cabinets, & quartz countertops. The stunning floating staircase & porcelain tile flooring throughout the interior add to the homes contemporary allure. Open living spaces are designed for seamless entertaining & relaxation, with large windows that flood the interiors with natural light & provide picturesque views.This Green Certified home is equipped with (3kw) solar panels, water cistern, & grey water reuse system, showcasing a commitment to sustainability & environmental consciousness. Enjoy this Smart Home with the convenience of WiFi-controlled lighting, along with luxury fixtures that elevate the living experience. Grillers will love the outdoor kitchen equipped with a 48 grill, side burner, sink, refrigerator, & ice machine.There is an 11 person a Swim Spa in the back to dip in or take a swim after a day on the boat. Outdoor enthusiasts will appreciate the 50 concrete seawall, offering easy access to the pristine boating waters of the Florida Keys. Approx. 1200 sq ft of expansive terraces to enjoy the tropical breezes, outdoor living is taken to new heights. This exceptional property also features a garage & downstairs storage. This home presents a rare opportunity to own a new luxury residence in one of the most desirable locations in the Florida Keys. Dont miss your chance to experience the epitome of coastal luxury living - call today to schedule your showing! With ROGO permits coming to extinction in the Keys soon, lock in todays pricing! *Please Note - Renderings are for il

Experience the perfect blend of modern design and island-inspired luxury with this stunning home, situated on a generous 13,607 sq. ft. lot in Buccaneer Point Estates. Come enjoy waterfront living on a tranquil lake featuring an in-ground swimming pool with the added benefits of solid concrete block construction, a durable metal roof, along with impact-resistant windows and doors throughout.This home features 3 bedrooms, 2 full baths, and 2 half baths, all within a spacious open-concept layout. High 10 ceilings and 8 doors contribute to a bright and airy atmosphere, while custom trim details add a refined touch. The well-appointed kitchen includes custom cabinetry, Quartzite countertops, a stone accent wall, stainless steel appliances, a gas range, and under-cabinet lighting.Additional highlights include walk-in closets with built-in shelving, plantation shutters, porcelain flooring, and designer lighting fixtures. The property also offers tiled terraces and stairs for easy indoor-outdoor living, a functional laundry room, ground-floor storage, and pre-wiring for security and surround sound. This home combines comfort and sophistication, offering a refined living experience.

Experience the charm of Old Town living at 923 Eaton St, a beautifully updated historic home featuring three bedrooms and two full bathrooms, ideally situated just steps from the Historic Seaport and a short stroll to Duval Street. Offered turn-key, this property combines classic Key West architecture with modern enhancements, making it perfect for enjoying the local lifestyle.Inside, youll find Dade County Pine walls, hardwood floors, and renovated kitchen and bathrooms. The second floor boasts two inviting bedrooms, while the first floor offers a charming bunk room. Step outside to discover a spacious 10x20 ft heated saltwater pool and a private tropical backyard oasis, perfect for outdoor relaxation. Additional features include a newer metal roof, an impact-rated sliding glass door leading to the rear deck, and efficient ductless AC units.This charming home is fully furnished and ready for you to move right in or to generate a reliable income as an investment property, allowing you to enjoy all that Key West living has to offer!

Experience the lifestyle of waterfront living in this quintessential Islamorada home. Featuring 3 bedrooms and 2 bathrooms on the second floor, this residence includes an interior staircase leading to the legal, above-flood downstairs living space. The first floor offers a second living room--easily convertible into a fourth bedroom--along with a full bathroom, making it ideal for separate guest quarters or expanded living. The property is encompassed by a stunning front coral wall and offers 50 feet of dockage with direct bay access. Conveniently located near schools, this home sits in the last neighborhood along the four-lane highway. Discover why The Colony is a beloved community among locals--schedule your visit today!

What a great location! Discover Serenity at Manatee Crossing, nestled along the picturesque waterways of Islamorada, where over 200 feet of waterfront embrace you from two sides. Immerse yourself in an outdoor haven, boasting a captivating pool, charming Chickee-hut, and indulgent hot tub area - each offering front-row seats to the wonders of nature. From manatees to graceful migratory birds, the surrounding mangroves create a natural sanctuary for this remarkable property. Step inside this timeless CBS home, where modern comfort harmonizes with island charm. The lower level welcomes you with a living area and full bath, while three bedrooms and three baths await on the upper level. As the sun sets, ascend to the expansive concrete roof and toast to another day in paradise, with panoramic views painting the sky in hues of orange and pink. For boating enthusiasts, get ready to launch into your aquatic adventures, while nature lovers can explore the bay at their own pace, taking in the unique beauty of Tavernier Creek and beyond. Whether you seek thrilling ocean escapades or peaceful backcountry journeys, this property offers the perfect launchpad for all your Florida Keys dreams. Dont miss the chance to experience the magic of Manatee Crossing - schedule your private tour today and discover why this property is truly special.

Tranquility meets coastal living, discover this stunning concrete constructed home built in 1993. Located in the desirable subdivision of Tropical Bay Estates this elevated waterfront residence offers unparalleled access to both the ocean and bay, just 15 minutes by boat. The iconic No Name Pub is just a 2-minute drive or a 15-minute walk away for some of the best pizza in the Keys. A few property highlights to include: 50 Concrete seawall & concrete patio, lush, low-maintenance landscaping featuring bamboo and a fruit-bearing mango tree. Enclosed courtyard entrance, two oversized screened lanais - one upstairs & one ground level, plus 1,100 sq. ft. enclosed 3-car garage, all impact windows/doors for storm protection. More updates: New metal roof, central A/C system & two mini-splits. Large primary suite with California closet system, whirlpool tub, walk-in shower, & dual sinks. Kitchen updates: Samsung 4-door refrigerator, LG dishwasher, GE Cafe induction double oven range w/downdraft exhaust and wine cooler. Also installed throughout the home are new ceiling fans, LED lighting and bi-fold doors. Waterside and outdoor features include a 15k boat lift, bait cleaning station, underwater fish lights at the dock, crank-out awning dockside, outdoor sink with stainless steel cabinet in the downstairs lanai. A few more items to add to the list: 1,000 lb. Cargo lift, whole-house water filtration & softener system, tankless hot water system, Samsung front-load washer & dryer. In the garage, a refrigerator with ice maker, auxiliary power panel for generator, 13,000-watt dual-fuel generator, 250 lb. ice maker, two deep freezers, two insulated hurricane-rated garage doors with openers. This meticulously maintained home offers a blend of comfort, durability, and waterfront convenience.

Located on the main free flowing canal just off the Bay of America and a short ride to the Ocean thru Tavernier Creek or Snake Creek. Fishing diving, paddleboading is right here!! 254 Navajo Street offers two bedrooms two bathrooms upstairs and one bedroom and one bathroom downstairs and an open concept living area upstairs. With a stainless-steel kitchen, granite countertops, and a private backyard oasis featuring a sparkling pool with water and fire features, this property is perfect for entertaining. Its close proximity to the ocean and local amenities makes it a slice of paradise waiting for you to call home. This canal front home has 78 of dockage with a boat lift. There is a shaft ready for elevator installation. Owner is a licensed Real Estate Agent.Come see this little gem...great for your pets as well.

This stylist distinctive remodeled as of 1/24, 2nd floor 3-bedrooms, 3-baths, home features new kitchen, stainless steel appliances, and meal-prep island Quartz countertops. This elegant house offers breathtaking bay view sunsets from roof top, where you can relax and enjoy yourself. Stunning outdoor pool, BBQ, outside shower, 15 thousand pound boat lift. And as a bonus downstairs bedroom and full bathroom. Owners Finance if needed.