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

NEW PRICE!A Secluded Waterfront Paradise in the Heart of the Florida Keys. Step into a world of minimalistic elegance and tranquility at this one-of-a-kind coastal oasis. Tucked away on over an acre of lushly landscaped, private property stretching from highway to water, this architecturally unique home offers serene luxury and endless possibilities. Arrive via a tree-lined driveway to discover a striking three-story coastal retreat. Featuring four private en suite bedrooms, each with its separate entrance, the home is designed to provide privacy and relaxation for family and guests alike. The sleek, contemporary design integrates seamlessly with the natural surroundings, offering captivating water views from every vantage point. Designed with entertaining in mind, this property boasts multiple spacious outdoor entertainment areas, including verandas overlooking the sparkling pool, sand-laden grounds, and tranquil waterfront oasis. Gather around the expansive fire-pit with seating for up to 14, perfectly situated at the waters edge for unforgettable evenings under the Keys starry skies. Adding to its versatility, a secondary garage structure--measuring over 700 sq. ft. with soaring 11-foot ceilings--has been artfully re-imagined as a flexible guest space or personal retreat.With SR zoning permitting vacation rentals, this unique property offers endless opportunities, whether as a family compound, corporate retreat, or lucrative investment. Its layout, designed to maximize privacy and individuality, makes it especially appealing for those seeking a distinctive and adaptable space.Additional features include:Potential for docking a houseboat or watercraft, as previously enjoyed. Ample parking and storage, ideal for all your waterfront toys. A kayakers or paddleboarders dream, with access to nearby mangrove trails. A secluded yet accessible location, offering privacy while remaining close to the best of the Keys.Dont miss the opportunity to own this

Welcome to Latitudes in Islamorada, where luxury living meets coastal elegance. This stunning 4-bedroom, 2.5-bathroom, three-story residence is nestled within the prestigious Port Antigua community on Lower Matecumbe Key in the Florida Keys, a sought-after enclave known for its live-work-play lifestyle. This exceptional property offers unparalleled features, including breathtaking 360-degree views from the top floor, a custom-designed pool and spa, a spacious tiki hut complete with a grill and bar, a private elevator, and dual boat lifts (12,000 lb & 20,000 lb) with deep water dockage.The three-story layout at Latitudes is masterfully designed to showcase an open-concept living space on the top floor, where the dining, living, and kitchen areas flow seamlessly--reminiscent of an upscale penthouse. Expansive covered balconies offer additional outdoor living spaces, while a private guest suite on the ground floor provides versatile options, easily convertible into an office or playroom. The home is fortified with impact-resistant doors and windows throughout, ensuring both security and peace of mind.The second floor is dedicated to comfort, featuring a luxurious master suite with an ensuite bath, along with two elegantly appointed guest rooms and a guest bath. The ground level includes a secure, enclosed garage and a finished storage area, offering ample space for all your needs. At Latitudes, every detail has been carefully considered to provide a perfect blend of style, functionality, and luxury.

Coastal Elegance Meets Timeless Craftsmanship in Safety Harbor- Welcome to Piece of Quiet, a winner of the Miami Herald Fame award for custom homes with unique architecture. Nestled in the coveted Safety Harbor neighborhood, this CBS construction home is a masterful blend of strength, style, and coastal luxury. Wrapped in island-style siding, the home exudes character and seaside charm, while grandeur arched French doors in the main living area flood the space with natural light and frame stunning waterfront views. Delight your senses with the custom terrace floors that were modeled after those at the Historic Cheeca Lodge & Spa. Step inside to the rich beauty of white oak flooring, offering both durability and sophistication throughout. The open-concept design seamlessly connects indoor and outdoor living, perfect for entertaining or enjoying peaceful moments by the water. Boating enthusiasts will revel in the 70 feet of dockage on a serene, protected deepwater basin, providing direct access to the bay and quick ocean access via the two bridges at Channels 2 and 5. Whether youre setting sail at sunset or savoring the gentle breezes from your private dock, or waterfront decks, this home is a rare gem not to be missed.Dont miss the opportunity to own this waterfront retreat--schedule your private showing today!

EXQUISITE OCEAN VIEW POOL HOME! Welcome to Tuts Cay, a luxurious 4 bedroom, 5.5 bathroom, a sanctuary in The Village of Islamorada, Florida Keys. This property spans on two lots, offering stunning ocean views and privacy. The resort-style pool area includes an outdoor kitchen and golf putting green, perfect for relaxation and entertaining. Boating enthusiasts will appreciate the ample dockage and nearby community boat ramp. Inside, enjoy sophisticated living areas with en-suite bathrooms for each bedroom plus a pool bath. The residence features televisions in every room, large balconies, dual kitchens, and a wet bar. Exterior amenities include a rooftop lounge, private pool and hot tub, sun loungers, hammock, outdoor bar, mini fridge, built-in grill, and firepit. Tuts Cay blends luxury, convenience, and natural beauty for an unforgettable vacation or full time home. Located in the Sports Fishing Capital of World!

Beach life simplicity perfectly describes this pristine 3 bedroom, 2 bath oceanfront home with pool, covered patio, and gated for privacy. Stunning beach and ocean views are enjoyed from upper porch, lower level covered patio, living room and 2 of the 3 bedrooms.Fully remodeled in 2021, this charming get-away has been entirely refreshed with new everything...including impact windows and doors, metal roof, flooring, new appliances, central air, pool equipment and electric gate. Furnishings and finishes reflect the coastal cottage style creating the epitome of relaxation and embodying the Florida Keys lifestyle.

Extremely well appointed 5 bedroom 3.5 Bath home with easy access to the Atlantic Ocean or the Florida Bay via Adams Waterway . This Concrete home is on the Cut with 48 ft of protected cut in dockage that has a 14,000lbs remote controlled boat lift and davit pads with one davit for a Wave Runner. Extra large heated pool with an 8 person a waterfall overflow hot tub with color changing pool lighting. Outdoor shower and convenience bath. This concrete home has Impact windows, doors and sliders plus a newer metal roof and plenty of downstairs storage, all on an electric gated landscaped lot. Kitchen has newer updated Stainless Steel appliances with a large Quartz Island with waterfall edges that is perfect for entertaining large or small groups. Convection oven/microwave with GE Vented hood and water pot filler , also known as a pasta faucet ,that would make any cook seem like a chef.

NEWEST DEVELOPMENT IN DOWNTOWN ISLAMORADA!! Come preview finished units NOW. Only ONE HOUSE LEFT. An exclusive, gated enclave on the Atlantic Ocean, Oceanside is nestled between the Cheeca Lodge and the Caribbean Resort, offering the very best of location, privacy and island living. Low maintenance concrete block construction, this home has been built above flood level. Spacious living area of more than 2,500 square feet, with fully collapsing Euro doors both on the second floor, leading out to a covered balcony, and on the first floor, opening to the private pool and deck, Oceanside House 6 boasts four bedrooms with ensuite baths, plus a first floor powder room. Large open kitchen, island and living area flow seamlessly. The property also allows vacation rentals. This beauty will not last! Make an appointment to visit the site today.Owner is Florida licensed real estate agent.

Open Ocean 3/2 Concrete Pool Home with Dockage in the heart of historic Old Tavernier! Enjoy expansive ocean views, year-round ocean breezes, deep water dockage and a stunning custom pool by DAsign Source with relaxing rock waterfall, beach entry and swim jet in the deep end. After a long day of fishing, sip a cocktail in the pool or lounge poolside at your custom bar and tiled cabana area below the home in the shade. Also downstairs is a storage area and a tiled foyer entry to welcome you into the home. Upstairs on the first level is a spacious great room with open kitchen with custom cabinets and Corian counters, dining nook area and large ocean view living room. A wide and shady oceanfront balcony extends the entire length of the great room. with plenty of room for outdoor dining and grilling with a gorgeous view of the sparkling Atlantic. Also on this floor are the laundry area, a full bath and two guest bedrooms. On the top floor is a sprawling primary suite with soaring ceilings and breathtaking open ocean views. There is plenty of room here for an office plus separate sitting area, exercise equipment or even a nursery in addition to your king bedroom set. Theres also a deep walk-in closet and roomy primary bathroom with double sink, soaker tub and shower. The all concrete home with metal roof has impact windows and sliding glass doors plus accordion shutters for added protection. The yard is fully fenced and gated and the neighborhood offers an oceanfront community park and two local restaurants within walking distance plus quick and easy access to Tavernier Towne shopping center, fine dining, a movie theater and more. Call today!

INVESTORS! Discover 11 Bay Road and the charm reminiscent of Old Florida in this exquisite Bayfront open water home in North Key Largo. This estate sized property offers spectacular, due west-facing sunset views year-round. Set on an oversized lot with palm tree lined driveway and lush, mature landscaping, this property provides both privacy and serenity. A rare and private basin, sandy beach, jetty and dockage with 100 of deeded bay bottom enhance the appeal, while the native tropical surroundings invites ultimate relaxation. The residence features three bedrooms and three bathrooms within 1,724 square feet of air-conditioned space, complemented by expansive screened-in porches that overlook the Florida bay and waterfront. Dade County pine, tray ceilings and authentic Mexican tiled floors highlight the homes Old Florida charm. The well-designed split floor plan ensures privacy for the guest bedrooms, while the main living area offers a seamless connection to the stunning views and outdoor spaces.With the option to add an extended pier or boat lift, this property is perfect for boating enthusiasts. Additionally, this property offers a detached two-story garage and carport with ample storage and room for expansion. A neighborhood boat ramp and bayside park with 72-hour overnight boat parking are just a short drive away for added convenience. Access the ocean with a short boat ride through famous Adams Cut. This remarkable home offers an opportunity to embrace the Key Largo island lifestyle, whether as a private retreat or as a future redevelopment project. Dont miss your chance to experience this rare offering in one of the areas most sought-after locations just one hour from Miami. Contact us today to arrange a viewing.

Welcome to your dream home, where luxury meets nature! This exceptional waterfront property, originally built in 2009, was completely remodeled in 2024/25. With over 120 feet of pristine waterfront and a deep-water dock, this all-concrete home boasts a durable concrete roof, ensuring longevity and peace of mind. The newly installed impact windows/doors provide both security and energy efficiency while allowing in the natural light. A new concrete privacy wall encircles the property, complemented by two heavy aluminum gates. Imagine waking up each day to breathtaking views and direct ocean access! With over 105 feet of new, concrete dockage, you can easily moor your boat and enjoy the best of Floridas waterways. Whether youre an avid fisherman, boating enthusiast, or simply enjoy the serenity of the water, this property is perfectly positioned to fulfill your needs. Plus, buy fresh local seafood right at your doorstep. The heart of this home is its kitchen, featuring top-of-the-line JennAir appliances, perfect for culinary enthusiasts. The spacious open-concept living area is designed for entertaining, with thoughtful touches like solid core doors and new railings both inside and out. Zebra shades throughout the home provide a chic flair while allowing you to control the sunlight. Elevate your lifestyle with your private rooftop deck, offering expansive views. This is the perfect spot for enjoying sunsets or hosting gatherings. Nestled in a great neighborhood, this property is near the community park and some of Key Largos best restaurants.A pool permit has been applied for, providing the opportunity to create your own personal oasis right in your backyard. Picture lounging by your future pool, entertaining friends. Every detail has been meticulously chosen to create a living space that is both that is both functional and luxurious.From the moment you step inside, youll be captivated by the elegance and comfort that this property has to offer.

This 4-bedroom, 5-bathroom gated estate is a true gem, offering a luxurious and private waterfront lifestyle. Perfectly situated on a corner lot, it boasts breathtaking open bay views of Blackwater Sound, providing a serene and scenic backdrop. Inside, the home features a Hausscape-designed Italian chefs kitchen, equipped with premium appliances such as a Sub-Zero refrigerator, Wolf 30-inch gas cooktop, and an icemaker -- ideal for both culinary enthusiasts and those who love to entertain.The property also includes detached guest quarters, providing a private and comfortable space for visitors. The outdoor space is equally impressive, with a sparkling pool, attached jacuzzi, and an expansive area for relaxation and gatherings. Boating enthusiasts will appreciate the propertys remarkable waterfront features, including over 220 feet of boat dockage and two boat lifts, making it a perfect retreat for those who enjoy the water. This home offers the ideal combination of sophistication, comfort, and convenience in a truly exceptional setting.

UNIQUE & SPACIOUS BOATERS & OUTDOOR ENTHUSIASTS WATERFRONT HAVENThis nearly quarter acre waterfront property, tucked away with steps from Sunset Point in the coveted and secluded Islamoradas Indian Mound Waterways Neighborhood, is a solid concrete block home secured with automatic and aesthetic roll down hurricane screens. It offers unobstructed views of the Florida Bay with extensive views of the two canals converging. From the homes wide upper living room deck or the 93 feet of concrete dock, observe the dolphins swim and play. Throughout the day, manatees glide by. The four aquarium view underwater lights attract multiple tarpon that linger throughout the night. Soak in the soothing sounds of the coconut fronds. spurred by Florida Bays gentle breeze. Fishermen and boating enthusiasts can easily launch and secure their boats on either of the two boatlifts with walk-on platforms, decked with dual power and water pedestals. The outdoor custom kitchen is equipped with a killer dock fish cleaning station, all stainless steel ice-maker, sink with faucet, refrigerator, large stove and grill with granite countertops. Guests can relax in the hammocks, in the private Bahamian sandy beach adjacent to the kitchen. Dip and swim in the deep and wide lap pool that is cooled or warmed by the homes large 36-panel solar generation system. Propane-fueled tiki torches illuminate the property. The large concrete firepit adds warmth after a cool swim. Gated grounds are landscaped with delicious tropical fruit trees and plants such as mangoes, pineapples, key limes, coconuts, and bananas. Secure your Recreational Vehicle with RV hookup within the gates. Property amenities include access to the neighborhoods local private beach and dock. As a Plantation Key property owner, enjoy Islamoradas amenities: additional bayside beaches, pickleball, tennis, boat docking, amphitheater, and more. The property is move-in-ready or refer to the Architectural Drawings for remodel ideas.

This brand-new tri-level home in the FL Keys perfectly captures the essence of sophisticated luxury & relaxed island living. With both bay & ocean access, 60 ft. of canal frontage + private concrete dock, its ideal for saltwater enthusiasts. The home flows seamlessly from the rec room & summer kitchen to pool area, all set in a fenced yard - perfect for kids & pets. The 2nd level offers open living & dining, kitchen island, sleek wet bar & laundry room. An expansive balcony is perfect for family dinners & unwinding. Upstairs, elegant finishes & water views offer a peaceful master retreat. Just blocks from Tavernier Marina & fuel station, close to the top dining spots in Islamorada & only 90 mins. from Miami, this home is an ideal vacation retreat w/no HOA & great rental income potential.

4 bedroom 3.5 bath gorgeous waterfront home in Islamoradas Port Antigua awaits its new owner! Freshly painted, recent new roof, impact windows, Roll down shuttered second level outside balcony for entertaining, top of the line kitchen with Miele and Sub Zero appliances and Faber exhaust island stove, exquisite baths, wine cooler, ice machine (negotiable) grand staircase entry way, alarm system, wired for stereo inside and out, covered parking, room for pool, great entertainment and storage area on ground level along with spacious tackle and storage. Tropical fruit trees, shady side of the canal and a superior neighborhood park with ramp and private homeowners beach round out this Keys Treasure. 27500lbs elevator lift for your big boat. The 2022 42ft Custom Freeman Catamaran offshore fishing boat can go with the house for an additional1.1 Million. This can truly be the fishing package youve been looking for. Shown by appointment only. Contact agent for your personal tour.

Located in a private, gated community in the heart of Islamorada, 109 South Drive is a rare waterfront retreat that perfectly blends luxury, comfort, and the ultimate Florida Keys lifestyle. The main home features 4 spacious bedrooms and 3.5 beautifully designed bathrooms upstairs, while a separate 1-bedroom, 1-bath apartment downstairs offers privacy for guests or rental potential. Enjoy a custom resort-style pool surrounded by lush, tropical landscaping and a brand-new designer kitchen by Allabastro Designs. Boaters will appreciate the protected dockage with an ipe dock and direct ocean access -- no bridges, no long idle canals. Relax on the rooftop balcony with panoramic ocean views or entertain on expansive outdoor patios. With its unmatched access, thoughtful upgrades, and serene island ambiance, this property is a true Islamorada gem.

Sellers will consider contributing to buyers closing costs depending on price and terms. Are you looking for a newly renovated Port Antigua home that has plenty of outside entertaining space and 90 ft. of dockage? Youve found it! This home is a top-performing 5-Star vacation rental, projected to generate approx. $70,000 rented just 6 months of the year. Home is being sold with furniture, professional decor and everything you need for a turn-key income producing vacation rental. With a welcoming open floor plan, the 4 sets of impact sliding glass doors and large windows let in ample natural light to the main living level. Impact windows and doors were installed in the entire home in 2019. The kitchen features Bosch stainless appliances, double thickness granite counters, 2 reach in pantries and plenty of seating for the chefs helpers. On this level there is also a guest bedroom and bath and a large, open canal front terrace. The laundry room has additional storage and the on-demand tankless water heater. Interior stairs lead to the primary suite with large en-suite bath, as well as, another guest bedroom with en-suite bath. On the ground level the large driveway covered with concrete pavers offers ample parking, carport and fabulous entertaining space cooled by the east breeze in the summer. A garage and air conditioned workshop to store all your fishing gear and golf cart and is only steps away from the 90 ft. wide concrete dock with a 10,000 lb. boatlift, mooring whips and a fish cleaning station. Dock was resurfaced in 2024. Located in a quiet location on a cul-de-sac in the best private bay-beach community in Islamorada, Port Antigua. Port Antigua provides a degree of anonymity that other Islamorada communities cannot equal, despite being just a short drive from the areas most popular attractions. Its beautiful white sandy beach, complete with Tikis, picnic tables, and grills, along with our large canals and private boat dock, assist in making thi

Welcome to Paradise Point--your private oasis with breathtaking views! This stunning concrete home embodies the ultimate in ocean living, featuring a durable metal roof, all impact windows and doors and a charming wraparound walkway.Indulge in alfresco dining or unwind on your spacious, covered patio. The open-concept layout offers ample space for entertaining or relaxing in style. This home comes turn-key with all the furnishings!This move-in ready retreat includes new pool equipment and fresh paint throughout. The primary bedroom is its own floor, boasting a luxurious large walk-in shower, dual sinks, and a private porch overlooking the ocean. Imagine waking up to the sunrise at the foot of your bed!Stay comfortable year-round with central AC, complemented by individual mini-splits for your customized comfort. The garage offers generous storage and features an electric vehicle charger, while the exterior includes an RV charging plug, with all electrical systems updated for maximum power. Plus, theres a versatile non-conforming bonus area downstairs. Dont miss your chance to own this piece of paradise--its easy to show and ready for you to call home!

Discover the tropical privacy on nearly half acre on this Caribbean-style updated home which offers stunning open water views of Largo Sound from one of the areas prime locations. The property features 120 feet of concrete dockage with electric and water. The basin has convenient stairs to launch your water toys. Home offers 2 bedrooms 3 baths upstairs with an open concept living area with Saltillo tiles, granite countertop, stainless steel appliances, vaulted white tongue and groove ceilings, impact sliding glass doors in livingroom on 2 walls accentuating the open water views. Interior stairs lead to another bedroom, full bath and livingroom downstairs. Enjoy the professionally landscaped grounds, privacy walls, and mature palms surrounding a saltwater heated pool with waterfall feature completed in 2018. Concrete dock was expanded and reconstructed in 2019, with a 16K lb elevator boat lift, extensive pavers and gated entry way for ultimate privacy.

BACK UP OFFERS WELCOME! This is a must-see open water property priced below appraised value! Welcome to your private waterfront sanctuary in Key Largo, showcasing breathtaking open water views from every room.This CBS-constructed home boasts 3 bedrooms, 3.5 bathrooms, and 2,466 square feet of living space, with an additional 900+ square feet on the lower level. A whole-house generator with automatic switch-over and a brand-new 1,000-gallon propane tank (installed in 2024) offer peace of mind.The entertainers kitchen includes a 5-burner DCS cooktop, Viking range hood, convection microwave, full-size freezer, and a countertop ice maker.Outdoors, relax in the custom 35,000-gallon saltwater pool with a sun shelf, spa section, 4-ton heat pump, electronic controls, and auto-fill system.Boaters will love the 65-foot dock with two lifts (10,000 lbs and 7,000 lbs). Additional features include: A putting green with two chipping areas. Two tiki huts (one custom with a sprinkler system). Ample parking for RVs, boats, and toys. An electric carport windscreen curtain. Multiple storage areas, including a permanent shed. A queen-size Murphy bed for guests.Other highlights: elevator access between levels, solar-assisted hot water heater (2024), dual A/C units with new 2024 condensers, concrete privacy walls, a secure gated entry, and adjacency to a never-to-be-developed mangrove preserve.Agent related to owner.

Resort style living! Located on a quiet Cul-de-sac in the highly sought after Port Antigua neighborhood. Expansive DOUBLE LOT with 170 Ft. of water frontage. For the avid boater this is a dream come true! Surrounded by lush manicured landscaping providing the utmost privacy. Pond and inground heated pool complete w/outdoor kitchen. 3 Story concrete home w/ 6 bds 5 baths. 2nd Floor living space offers an open floor plan that seamlessly connects the kitchen to the dining and living areas, youll never miss a moment with family and friends. 3rd floor master suite offers bay views from its private balcony.Exceptionally wide clear canal. Pedestal with 30 and 50 amp shore power station. Direct bay access. Quick ocean access Via Channel #2 Bridge and Channel #5 Bridge. Elevator boat lift. Davits. Fish cleaning station. Port Antigua neighborhood offers a private homeowners park with a bayfront sandy beach, tikis, grills and a boat ramp. Dont miss this opportunity to own your piece of paradise. Your dream home in Islamorada awaits!**BUYER TO VERIFY ALL INFORMATION**