Lower Keys Waterfront Homes for Sale, Single Family Houses, Open Water, Ocean and Bay / Gulf Views

Welcome to paradise at 22562 Jolly Roger Dr in beautiful Cudjoe Key! This custom built, 4-bedroom, 2-bath home features open water views, a designer kitchen with high-end finishes and Viking appliances. In addition, on the first floor there are two guest bedrooms, an office and bathroom. The second floor is where you will find the third bedroom as well the primary bedroom complete with private balcony, ensuite bathroom and walk in closet. Outside the property boasts double decker porches, covered hot tub, full swim spa, and new dock. In addition to the garage there is ample room for vehicles, boats and extra storage. The property is equipped with RV electrical and sewer hookups for added convenience. The property features impact windows and doors and is a stones throw from American Shoal, Lighthouse, Looe Key Reef, and Square Grouper restaurant.

OCEANFRONT & CANALFRONT GEM-- A Rare Slice of ParadiseThis exceptional 17,560 sq. ft. property offers the best of both worlds with stunning open water views and protected canal frontage. The main home is a beautifully maintained 2 bedroom, 2 bath residence featuring 155 feet of sweeping ocean vistas, impact windows and sliding glass doors, and a layout designed to showcase breathtaking sunrises and local wildlife.Included with the property is a buildable-size adjacent lot plus a 4,218 sq. ft. canalfront parcel complete with a 34-foot dock and 10,000 lb boat lift--providing deep water access for effortless boating adventures.Enjoy true island living with a private swim spa/jacuzzi, multiple outdoor lounge areas, and lush tropical landscaping that creates your own serene oasis. Practical features include a carport with storage, two sheds for gear, and ample space for entertaining or relaxing.Whether youre an avid boater, nature lover, or simply crave the tranquility of waterfront living, this is more than a home--its a lifestyle. Located in Cudjoe Gardens, youll also enjoy a local marina and restaurant just minutes away.

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.

MODERN ISLAND RETREAT - 4 Bedroom CBS pool Home with great Boating Access on Bogie Channel, Big Pine Key!Experience the best of the Lower Keys lifestyle in this near-new, concrete block (CBS) home, perfectly positioned near iconic No Name Key where you catch the sunrise views over the water.Offering 4 bedrooms, 3 1/2 bathrooms, an exceptional floor plan, this elevated home delivers coastal living with the peace of mind that comes from newer construction. Landscaping starting next week. Be sure to check out the 3D Matterport Tour and Floor Plan.Built in 2022, this furnished pool home features impact-rated windows and doors, plank-style tile flooring, and a chef-inspired kitchen complete with quartz countertops, stainless appliances, and ample counterspace for entertaining. High ceilings and an airy floor plan invite the natural light, while the expansive covered balcony is ideal for taking in the island breeze and surrounding views.Situated on a generous lot, theres room for all your toys--trailers, RVs, and a storage room by the pool and tiki and covered parking with pavers. With a 10,000 pound lift and 30 composite dock, off to the water you go. Whether youre heading out for a fishing trip, snorkeling adventure, or just cruising the backcountry waters, this home puts you in the heart of the Florida Keys lifestyle.Located just minutes from the natural beauty of No Name Key, known for its wildlife, biking, and tranquil atmosphere, youll enjoy a rare combination of convenience and nature, not to mention youre walking distance from the infamous No Name Pub. Big Pine Key offers local shops, dining, and essential services, and youre just a scenic drive from Marathon or the magic of Key West.Whether youre searching for a primary residence, a weekend getaway, or a vacation rental investment, this modern island home delivers space, quality, and unbeatable location. Schedule your private showing today and start living your Keys d

Escape to your own slice of paradise at this Oceanfront retreat on the breathtaking shores of Big Pine Key. Perfectly situated on a 1/2-acre beachfront lot, this stunning home offers a rare blend of tranquility, elegance, and natural beauty. From unmatched sunrise to sunset views to the private sandy beach, this residence is the ultimate Florida Keys oasis. Step inside and be captivated by the expansive great room, featuring vaulted ceilings and a soaring 20 coral fireplace that serves as a dramatic focal point. Natural light floods the space, creating a warm and inviting atmosphere that seamlessly blends indoor and outdoor living. The spacious screened porch features a wet bar and provides the perfect vantage point to savor the coastal breeze while taking in the panoramic views of the Ocean. The split floor plan ensures privacy and comfort, with two generously sized bedrooms sharing an updated bathroom adorned with custom tile work. The primary suite is a true sanctuary, offering sweeping ocean views, a spa-like en-suite bathroom, and a walk-in closet. An additional loft space overlooks the great room, making it an ideal spot for a home office, reading nook, or a 4th bedroom. Designed for entertaining, the chefs kitchen boasts a large center island perfect for meal prep or hosting large gatherings. Outfitted with stainless steel appliances, this kitchen is a culinary dream come true. The outdoor living experience is unparalleled, with a rooftop deck perfect for sunbathing by day and stargazing by night. The private sandy beach and quiet neighborhood, home to the beloved Key Deer, provide an idyllic backdrop for relaxation. Built for peace of mind, this home features CBS construction, a standing seam metal roof, and a whole-house generator, ensuring safety and convenience year round. Whether youre looking to entertain guests, escape the hustle and bustle, or simply soak in the beauty of the Florida Keys, this retreat captures the essence of true coastal living!

Welcome to your private paradise in the Lower Keys! This beautifully updated 2 bed, 2 bath two-story home offers complete privacy with no direct neighbors on all sides, making it a peaceful escape surrounded by nature and the charm of the Key Deer.Step outside to your tropical oasis featuring a brand-new concrete heated pool, concrete dock with a boat lift and jet ski lift, plus an elevated sundeck perfect for soaking up the sun or enjoying canal views. The backyard is currently being transformed by a professional landscape designer set to be completed early June and WILL be included in the sale, adding lush, tropical vibes, tiki hut and pavers around the pool to complete your island retreat.The ground floor offers a fully enclosed and renovated space, perfect for guests and entertaining and storage, along with a separate laundry room for added convenience. Both levels are equipped with impact windows and doors, plus electronic roll-down screens for added shade.Whether youre boating, lounging poolside, or enjoying the wildlife, this home is designed for true Florida Keys living offering many upgrades and renovations.SALE CAN INCLUDE BRAND NEW CUSTOM FLATS BOAT.

Enjoy deep draft dockage, 2 Boat Lifts, Garage and Pool plus no steps to climb at this 3 Bedroom 2 Bath home located in Cudjoe Gardens, an upscale waterfront community of CBS constructed Above Flood ground level homes offering a neighborhood full service marina and waterfront restaurant and bar. Enter into the open Great Room where a wall of impact glass doors overlooks the pool and water. The well appointed Kitchen features stainless appliances and center island for friends to gather around. Soaring cathedral ceilings are found in all Bedrooms including the Primary Suite complete with spa bath and picturesque pool views. Days are enjoyed by the waterfront heated pool or out on the water where world-class fishing and diving are jut minutes away. Lots of room for all of your toys in the attached 2-car garage or on the additional half lot on the side of the of the house. Boaters will love the quick deep water ocean access from the 100 flow through dock with 2 Lifts, 17K lbs and 14K lbs. The low maintenance home boasts concrete construction, impact windows and doors, metal roof and pea rock yard.

SELLER FINANCING AVAILABLE! This Beautiful Oceanfront Home in Cudjoe Key has undergone a full renovation and awaits its new owner! All new impact doors and windows, new AC, new flooring throughout and a stunning custom kitchen with granite countertops and stainless steel appliances are a few of the many updates in this amazing renovation . Offering Four generous size bedrooms with Three full bathrooms, it can easily accommodate a large family. The open floor plan of the living and dining room with massive cathedral ceilings , showcase this homes coastal character. Three sliders face the unmatched ocean view , and open to let the ocean breeze flow through the house. Step out on the 500sf covered porch to enjoy the indoor outdoor living and entertaining with breathtaking panoramic Oceanfront views. Do not miss this great opportunity, this is a one of a kind home. Call now to schedule your private tour.

COME SEE THIS HOME- Not a drive by- Must see inside and the back yard too.....Located on the West Side of the Island with excellent boating access this beautiful pool home is an entertainers dream place. All new paint inside. New Roof as of 01/2025. Stunning Sunsets & Sparkling waters for swimming, snorkeling, paddleboarding .... Home features 3 bedroom suites with full baths plus a powder room too. Impact doors and windows, tile floors throughout, Viking appliances, chefs kitchen, wet bar, icemaker & additional drink fridges. Large Tiki Hut with fans, concrete heated pool and chiller too. Bring your big Boat and Smaller one too.....2 boat lifts (20K and 12K), boat house, outdoor shower, swat mosquito system, RV hookup, Terminix warranty, video surveillance, large storage shed, full home surge protection, ample storage inside and out. All tropically landscaped, paver driveways & yard fenced for your pets and privacy. Full concrete seawall & covered boat slip. Home is offered mostly furnished and outdoor furniture is included too. Location! Location! Location! New Paint inside-neutral color. And New Roof 2025.

Luxury Waterfront Living in Prestigious Cudjoe Gardens. Discover refined island living in the heart of one of the Florida Keys most exclusive waterfront communities renowned for its deepwater access, upscale ambiance, and close proximity to Key West.This elegantly designed residence is perfectly positioned on an 8,000sf lot, offering exceptional canal frontage on a 50ft wide canal only 5 homes in and 2 min ride from open water. The home features 2,295 living sf plus 441sf garage and 225sf of porches, making for almost 3,000sf under roof! Home has beautifully appointed interiors, where luxury and comfort harmonize.The open-concept living space is adorned with 10 to 12 ft ceilings, abundant natural light, and premium finishes throughout. At the heart of the home is a custom-made epoxy and wood bar, a true showpiece that makes an ideal spot for entertaining in style. A custom built electric fireplace offering ambiance and warmth anchors the living room and invites relaxed evenings after a day on the water.The large kitchen is outfitted with beautiful granite with natural tones, stainless steel appliances, custom cabinetry, and an expansive island, flowing seamlessly into the second large living room where comfort is found! The primary master bedroom suite offers a tranquil retreat with in room office, his/hers walk in closets, and spa-like ensuite bath.Two additional spacious bedrooms and full bath, plus half bath and laundry room complete this large home. Additional features include elegant large plank Bamboo flooring, impact-resistant windows and doors, etched glass front door, plantation shutters throughout the home, a spacious garage, and thoughtfully landscaped grounds that reflect the natural beauty of the Keys.Step outside through the French glass doors to a waterfront screened in porch with ceiling fans. The 80ft concrete dock with 20k boat lift, working davits, 1000lb ice maker, cleaning station, make this a fishermans paradise! Room for a pool!

SELLER IS MOTIVATED! All furnishings convey with property if buyer would like. Discover the epitome of waterfront living at Tropical Bay Estates. This 2023 new construction home offers an unparalleled paradise for your family and friends. Begin your days with stunning sunrises, engage in world-class fishing, and soak in breathtaking water views from nearly every part of the house. Encounter the charming key deer in this serene neighborhood.Built with full CBS construction, this residence stands on 10-foot-high stilts and features 10-foot-high ceilings with 8-foot-high doors, ensuring both luxury and durability for tropical storms. The backyard is a haven for boating enthusiasts, featuring a boat slip and a 75-foot concrete seawall, complemented by a heated saltwater pool. Inside, the home spans over 2,000 square feet, showcasing an open floor plan that accentuates water views from almost every corner. Additionally, a versatile bonus room on the lower level can serve as an entertainment space or be converted into an extra bedroom.With impact windows, a durable metal roof, and all furnishings and appliances included, this residence is truly move-in ready--ideal for a family home or a high-end rental property. Contact us today for a private showing and experience the luxurious lifestyle that awaits you at Tropical Bay Estates.

June 11- Flooring complete, Cabinets in, walls painted, waiting for countertops, stucco, landscape. UPDATED PHOTOS. Check back often! Luxury Waterfront Living in a Highly Desirable Boating Community.Live in elegance in this fully renovated 3-bedroom, 3-bathroom en-suites concrete home, designed for modern coastal living. Every detail of this residence has been meticulously updated, including ALL NEW 2025 plumbing, electrical, and HVAC systems, ensuring worry-free ownership. Step inside to a completely reimagined interior, featuring high-end luxury finishes. The open-concept design is bathed in natural light, enhanced by hurricane-impact windows and doors offering both beauty and peace of mind. The chefs kitchen is a masterpiece, boasting premium appliances, custom cabinetry, and exquisite countertops, seamlessly flowing into the spacious living and dining areas and bonus coffee/wine bar feature--perfect for entertaining. Each bedroom is a private retreat with spa-inspired en-suite bathrooms. The thoughtfully designed layout allows for guest access to one of the en-suite bathrooms, ensuring convenience without compromising privacy. An additional outdoor terrace bathroom access provides seamless functionality for those enjoying the exterior living spaces--perfect for rinsing off after a day on the water.The primary suite is a true sanctuary, opening through a set of sliding glass doors to a private covered terrace retreat. This serene outdoor space is ideal for morning coffee or unwinding in the evening, offering a peaceful connection to the surrounding coastal environment.All of this beneath a durable metal roof adding to the homes longevity and appeal. Located in an elite boating community, this property offers excellent water access, making it a dream for boaters and water enthusiasts alike. Experience luxury, security, and an unbeatable lifestyle in one of the areas most sought-after family neighborhoods.

FINISHED -- NEW CONSTRUCTION!!! Luxury water view home with an in-ground pool on a 14,680 sq ft lot with dock and boating access. Brand new single level elevated CBS home over parking. Impact windows and doors, metal roof, 10-foot interior ceilings, stainless appliances and much more. Construction is completed, ready for occupancy.The property has a beautiful view over the water and a magnificent bridge that is rarely used due to the fact that only a few homes are on the other side of the bridge.

Escape to paradise! 5BR/3.5BA gated home in the Keys. Bamboo floors, fresh paint, screen patio. Elegant accents. Lush landscaping, private pool, hot tub. 2 levels, full bar, gourmet kitchen, walk-out patio. Master w/ walk-in closet. Stargaze from wrap-around porch. Must see this private oasis!

Waterfront Paradise for Anglers & Entertainers - Perfect for Family, Friends & Vacation Rentals.Welcome to the Ultimate Waterfront Luxury Retreat, Completely remodeled and redesigned for those who love to entertain. Excellent deep water access and yet just minutes to all the action downtown Key West has to offer.Seller will consider Owner Financing/Private Financing or even a full or partial trade. Elevated and storm resistant concrete construction, this home offers unmatched durability while embracing a modern coastal lifestyle.With four Spacious bedrooms and four beautifully appointed bathrooms, this home comfortably accommodates large groups with almost 2500 Sq Ft. interior Space. The newly finished open-concept dream kitchen is designed for socialising, featuring an oversized Island, seating up to 12 guests, making it the ideal host house for unforgettable gatherings and events.On the Second Floor, this dream home continues with a stunning custom built bar and lounge offering the ideal spot to start the party, watch a game or wind down after an exhilarating day on the water. The adjacent waterfront balcony sets the stage for relaxing and entertainment.The outdoor experience is just as impressive, featuring a large pool, hot tub, New Tiki Hut for those looking for shade, boatlift, concrete patio and game room - perfect for guests of all ages to enjoy. Excellent off Street parking for multiple vehicles, Boat Trailers or RV on over 9000 Sq. Ft. Lot.Whether you are heading out for world class fishing, or simply unwinding by the water, this Keys Home delivers the ultimate Florida Keys lifestyle.

BRAND NEW CBS Construction ready for occupancy!!! Amazing New Oceanside Home with 4 Bedrooms, 3.5 Baths, in Beautiful Cudjoe Ocean Shores, (Custom Built by Dream Builders of the Florida Keys). This home offers Open Water Views, Instant Deep Draft Boating for Big Boat Action, Protected Concrete step-down Dock, Open Floor plan, Dining Area, two Master Suites, High Ceilings, Chefs Kitchen with high end finishes, Stainless Steel Appliances, Quartz Counter Tops, Kitchen Island and Designer Lighting. Custom Bathrooms with Tiled Baths, Seated Showers, California Closets, Aqua Guard (waterproof) Performance Wood Based Flooring, Solar System, Custom Concrete Pool with Pebble Tech Finish, Pool Heater and Chiller, Master Bedroom Balcony and Direct Atlantic Ocean access. This home is spacious with over 1900 sq/ft under air, covered porch with Open Water Views, Impact Doors and Windows, Metal Roof, Concrete Storage Room Downstairs ( with Impact windows), Two Tiled Exterior Stair Cases for easy access, Custom Paver Driveway, AE flood zone, Tropical Landscaping by Trees R Us with a beautiful artificial turf lounging area and more. This is a rare find in the Florida Keys...bring the big boat and toys!!! Landscaping and Artificial Turf will be completed by 4/25/25. Easy to show...dont miss this gem! Easy and fun to show call listing agent for showings.

Luxury Waterfront Fortress with Breathtaking Atlantic Ocean Views. Experience unparalleled coastal living with stunning, unobstructed views of the Atlantic Ocean and Kemp Channel from this oversized 12,000 sq. ft. corner lot. This one-of-a-kind CBS home is built for strength and style, offering the ultimate in durability and design. Featuring 4 bedrooms, 3 baths, and a spacious two-car garage, the home is elevated for maximum protection--perfect for safeguarding vehicles, marine toys, and personal gear. A top-of-the-line elevator provides seamless access, large chefs kitchen, impact-resistant windows and doors, a newer roof, fresh paint and lush landscaping with fruit bearing trees. Boating enthusiasts will love the 193 feet of direct waterfront, including 105 feet of deep, protected canal-front concrete dockage and davits, providing effortless access to Kemp Channel, the Gulf, and the Atlantic Ocean. Privacy is paramount with a fully fenced, elevated lot, an electric gated entrance, and a dual concrete driveway. Dont miss this rare opportunity to own a fortress of elegance and strength in one of the most sought-after waterfront locations. Schedule your private showing today!

Open Water, Elevated, Concrete Home in best Waterfront community with easy proximity to Key West. 117 Key Haven Road was built to stand the test of time. With its Elevated concrete construction, metal roof and impact windows and doors, this home offers excellent protection of your investment and safety for your family and high quality comfort.Its combination of large 9300 sq ft. lot, excellent deep water access and stunning open water views of the bay and Gulf of Mexico make this an amazing opportunity for the buyer looking for a waterfront home.Configured as a 3BD/2BA, all on one elevated level with master suite and wrap around balcony overlooking the open water.Renovated kitchen with stainless steel appliances and beautiful granite countertops provides excellent space to prepare and enjoy a dining experience.Two separate single car garages offer ample storage, additional off-street parking and boat trailer parking also available.Large concrete deck in the rear offers many options to those who love to entertain and enjoy the outdoors. Plenty of room for a pool and property can accommodate multiple boats.

Stunning Waterfront Oasis in Key Haven - Elevated 3BR/3BA Home with Boating AccessWelcome to 37 Evergreen Ave. in Key Haven, Key West! Nestled at the end of a peaceful cul-de-sac, this beautifully updated 3-bedroom, 3-bathroom waterfront home offers the perfect blend of elegance and comfort. With 2,685 square feet of elevated living space on a generous 10,290 sq ft lot, every detail of this residence has been thoughtfully designed.Step inside to a light-filled large living room open to the waterfront balcony and an adjoining dining area--perfect for entertaining or simply relaxing with family and friends. The first floor also features a spacious updated kitchen with granite countertops, hardwood cabinetry, and stainless steel appliances. Upstairs, the expansive master suite serves as a true sanctuary, complete with a spa-style ensuite bathroom, large closets, and multiple French doors that open to a private balcony. The two additional bedrooms also offer balcony access.The home is elevated and equipped with hurricane-impact windows and doors and a full house generator providing peace of mind year-round. Enjoy the fresh coastal breeze from balconies off every room, or head downstairs to your private waterfront yard with direct boating access to open water offering access to the Gulf or Atlantic for fishing, diving, or sunset cruising.Additional highlights include a freshly painted interior and exterior, an enclosed air conditioned garage, and a paved driveway offering ample parking.

THE LAID-BACK LOWER KEYS ARE CALLING YOU ... experience life at a slower pace on this .81 acre open water estate with a 2-bedroom, 2-bath main house as well as a 1-bedroom, 1-bath guest cottage overlooking Bogie Channel. Entertain in the large, poolside tiki or on the covered platform at the end of the 463 ft. pier where family and friends can relax as they watch the sunset after a fun day on the water. The platform is equipped with a boat lift, floating jet ski dock and outdoor kitchen. Completely renovated, the 2-story CBS primary home offers the potential of adding a 3rd bedroom in the 1,950 sq. ft. living area.* Expansive impact-resistant windows capture spectacular sunrises and moonrises over the sprawling grounds and open water. Also nestled on the property is the renovated 536 sq. ft.*, frame-stucco guest cottage where your visitors can have their own space. The 35,330 sq. ft. property is fenced and accented by well-planned lighting. Monroe Countys quiet Palm Villa Park borders the south property line; the county also owns the large parcel to the north across the street with the intention of leaving it undeveloped. Tastefully furnished and move-in ready, this peaceful piece of paradise is just minutes from local shopping and eateries, yet only 30 miles from the excitement of Key West. *Source: Property Record Card