Upper Keys Homes for Sale, Single Family Houses, MLS Home Listings

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.

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**

Modern Coastal Luxury in the Heart of the Florida Keys! Built in 2019 with impeccable attention to detail, this stunning residence offers the perfect blend of modern design and island elegance. Featuring 4 spacious bedrooms, each with its own private ensuite bath, plus an additional full guest bathroom, this home delivers comfort, style, and privacy for family and guests alike. The gourmet kitchen is a chefs dream, outfitted with high-end appliances, custom cabinetry, elegant countertops, and an open-concept layout ideal for entertaining. The expansive primary suite is a private sanctuary, complete with a spa-like bathroom, large walk-in closet, and a private balcony where you can enjoy peaceful mornings or peaceful views over the water. This home is designed for the ultimate Keys lifestyle--impact-rated windows and doors provide peace of mind, while a whole-home generator ensures youre never without power. The exterior is just as impressive, featuring tropical landscaping, covered outdoor living areas, ample parking, and room for a future pool.Step outside to your brand-new 70-foot concrete dock, perfect for accommodating multiple large boats. Enjoy quick access to the Atlantic or Florida Bay for world-class boating, fishing, snorkeling, and diving adventures--right from your backyard. Located in one of Islamoradas most desirable neighborhoods, youre just minutes from great dining, shops, marinas, and excellent schools. This move-in ready home is ideal for those who demand luxury, comfort, and convenience. Whether youre seeking a primary residence, a weekend escape, or a luxury vacation rental opportunity, this home checks all the boxes.Live the dream and make this exceptional property yours today.

Not to be missed! House is in the X ZONE. Even more significantly the house is among very few of all the homes in the Keys that sit 14+ feet above sea level. Flooding is not a worry. Storm surge and wind impacts are also minimized with the location near the center of Key Largo. Permit for boat lift is pending at ACOE with approval expected in March. Home is built with a meticulous attention to detail, with no expense spared. The house columns, pool edging and the stairway to the seawall are all carved from the ancient coral harvested onsite. Two primary suites - one on the main level. One additional guest room. Two rooms currently used as his/her offices but could be switched back to bedrooms 4 and 5 (house rented for $18,000/mo previously). Garage-shop. Dedicated laundry area. Upscale fixtures and appliances throughout. Vaulted ceilings. Two AC units. Outdoor kitchen and massive tiki for entertaining. Privacy from neighbors on both sides. Triple lot, fully fenced. In ground salt pool and spa with heat pump. Second smaller garage on sea deck for boat stuff. Room to dock multiple 40 boats. Partial sunrise and sunset views. Easiest possible access to Bay and Ocean sides. Truly one of the nicest homes in the upper Keys under four million dollars.

INVESTORS! BUY the LOWEST PRICED Beach and Sunset Bay home in Buccaneer Point! Welcome to a life of serenity, sophistication, and waterfront bliss at 39 N Bounty Lane! This peninsula in Buccaneer Point Estates was developed to create a sense of privacy, in a peaceful bay unique to the Upper Keys. The estate-sized property has 80 of shoreline directly on the Florida Bay with deepwater dockage. This custom three-story, CBS waterfront home offers four bedrooms and three bathrooms with over 3,015 square feet of living space. As you step through the grand interior staircase entry, you are greeted by a seamless flow of space and light, enhancing the homes airy and inviting ambiance as you walk up to the main level. Expansive sliding doors and porches throughout the home offer breathtaking bay and sunset views. The gourmet kitchen is equipped with stainless steel appliances, granite countertops, a large laundry room doubling as a walk-in pantry and an elevator lift outside the dining area. The main living level features one guest bedroom and bathroom with a walk-in closet. Ascending to the third level, you will find three additional bedrooms and two bathrooms. The ensuite primary offers panoramic bay views from the private balcony. Immerse yourself in the private and spacious backyard, where mature palms and landscaping provide ultimate tranquility. Lounge in the hot tub, launch a paddle from your beach, or sit by a fire and savor the soothing sounds of the tropical breezes. With room for an in-ground pool and summer kitchen, the possibilities of creating your dream space are endless. The exterior is adorned in coastal blues and whites, and echoes the iconic color palette of the Greek Isles, creating a timeless sense of serenity. Boaters will delight in the pier dock, boat lift, and central location for quick oceanside access. This is a rare and great investment opportunity to own on one of the most coveted streets in Key Largo.

This unique wooded 3.2 acre parcel has over 100 boulder rip-rap shoreline directly on the ocean. Single Family Residence with ROGO exemption, but zoned SC. Highest approval rate via Monroe County is for MIXED-USE COMMERCIAL development. FKAA water utility service available.(This parcel may be sold together with contiguous parcel@95351 Overseas Hwy, at a REDUCED PRICE AK#1592978,RE#00483350 000000 13 62 38 PT TR 5&6 SOUTHCLIFF ESTS PB2-45 & PT GOV LOT 1 & ADJ BAY, 6.12 acres for grand total of 9.36 acres that would also include a 1352 sf 1959 5/3 cbs home metal roof.) Broker part owner/family owned

A Must See!! Completely remodeled property located in Ocean Isles Estates. Breathtaking open water views, Rare 2 car garage with plenty of extra parking space, waters edge pool, 17k lbs. boat lift, impact windows and doors, metal roof, 2 master suites, Remodeled 1 bedroom/1bath on lower level, recreation area, and much more. Pictures coming Soon!!

Investors! First time youll have the opportunity to buy this choice lot on the bay of Mutiny Place on popular Buccaneer Point Estates! Introducing a bespoke bay front residence on the Florida Bay never before on the market. Situated on the point of Mutiny Place, this property exudes exclusivity with a perfect balance of seclusion, accessibility, and breathtaking views. Encompassing just over half an acre along the serene Florida Bay, this property boasts bay and lake access, a private boat ramp, and unobstructed sunset vistas year-round. Enjoy as your vacation home or redevelop an estate sized property with an accessory structure, pickleball court or cabana pool cottage. Privacy envelops this estate-sized lot, featuring meticulously landscaped grounds that showcase native and mature flora, including countless unique palm varietals, trees, and grass, framing this coastal haven. Bask by the heated resort-style pool, unwind in the captivating Zen garden featuring a fire pit, and unwind under the pool-side tiki hut. Possibilities for more structure exist on the large lakefront lot by separating the 2 parcels.The residence is a thoughtfully designed three-bedroom, three-bathroom home with an open floor plan and interior stairs. Key features include pristine hardwood floors, split bedrooms on the main living level, hardwood cathedral ceilings with endless bay views, a secluded master suite occupying the entire third story, and twelve-foot-wide porches. Complete with Andersen impact sliding doors, PGT impact windows, and a new metal roof. Boating enthusiasts will appreciate the convenience of a 9k boat lift on a deep water pier dock and a private boat ramp for launching skiffs, paddles, and kayaks. Quick oceanside access north and south through Adams Cut or Tavernier Creek. Immerse yourself in the epitome of coastal luxury and tranquil living at 81 Mutiny Place.

Welcome to your waterfront sanctuary in the heart of Islamorada. Tucked away on a quiet street in the prestigious Village of Islamorada, this elegant 4 bedroom, 3 bath residence offers 3,204 square feet of open, light-filled living space designed for comfort, privacy, and effortless indoor-outdoor living.Situated on a generous 14,050 square foot lot, the property features 51 feet of canal frontage with a 20,000 lb boat lift and a wide turn basin--ideal for serious boating enthusiasts. Whether youre heading out for a day on the water or returning from a sunset cruise, easy access and maneuverability are yours.A gated entry welcomes you into this private retreat, where lush landscaping and a resort-style pool with spa--nestled into a natural rock formation--create the perfect backdrop for relaxing or entertaining. Inside, youll find spacious living areas, and an open kitchen built for gatherings.Head up to the rooftop deck to catch nightly sunsets over Florida Bay--your private front-row seat to the Keys most spectacular views.Located in the desirable Plantation Key area, families will appreciate access to top-rated schools including Plantation Key School (K-8), Coral Shores High, and nearby Treasure Village Montessori.This exceptional home blends casual island living with timeless luxury--your piece of paradise awaits.

Welcome to the hidden gem of Buccaneer Point, where luxury meets sustainability! This fully solar-powered home boasts breathtaking 360-degree views, perfect for entertaining while ensuring your privacy. The open floor plan and large porches seamlessly blend indoor and outdoor living. The chefs kitchen is a culinary dream, equipped with top-of-the-line appliances, expansive quartz countertops, and ample storage. Each bedroom showcases modern design and spacious comfort, with the primary suite thoughtfully located in a separate wing for ultimate tranquility and stunning views. Step outside to your private outdoor oasis, featuring a rooftop terrace ideal for relaxing or hosting gatherings, all while soaking in spectacular sunrises and sunsets. The property also includes a large pool, jacuzzi, boat ramp, and a spacious dock and 2 boatlifts making it easy to embrace the Florida Keys lifestyle. Dont miss your chance to own this extraordinary retreat!

LUXURY CANAL FRONT HOME IN ISLAMORADA!Brand new offering of the most exquisite coastal designed home offering spacious floor plans, entertaining spaces, and oversized rooms. This meticulously maintained home offers a split floorplan with a living room, wet bar, sizeable bedroom and full bathroom on the ground floor overlooking the outdoor kitchen and in ground pool. The second level boosts 3 bedrooms and 2.5 bathrooms, a great living room, pristine kitchen, and walk in laundry room/ office. The fenced in backyard welcomes you to enjoy your private yard surrounded in turf, low maintenance landscaping, and no neighbors directly across. The concrete dock holds a 20,000 lb boat lift and room for multiple boats! Along with this stunning home, you will also have access to the White Marlin Private Homeowners Beach, and all the close amenities in the area!

The Ospreys are back! Welcome to The Ospreys Nest; your perch by the Ocean in one of Islamoradas most coveted locations. Wake up to the sunrise and take a stroll down the turtle nesting beach, while also having the convenience of protected canalside dockage across the street. 20 dock but brought in stern-to, can accommodate larger boats. Spacious floor plan for all to enjoy, third story primary suite and beachside pool with heater and chiller for those hot summer days. True island living is here on Sunset Drive. Listing includes canal parcel with dock across the street RE#00389220-000100

Welcome to Paradise in Port Antigua, one of Islamoradas best-kept secrets! This spacious 4-bedroom, 4-bath home, built in 2019, offers the ultimate Florida Keys lifestyle with modern coastal design, deep-water dockage, and exceptionally low insurance premiums with the possibility of assuming a 2.8% interest rate! Located in the highly sought-after Port Antigua community, residents enjoy unique deepwater dockage and over 1,000 feet of private, exclusive beach frontage.This thoughtfully designed home features a well-planned layout with two primary suites--one on each level--providing privacy and comfort for residents and guests. Each floor includes a separate living space, connected by an interior staircase (all above flood!). A kitchenette on the first level adds convenience, making this home ideal for multi-generational living or hosting visitors. Upstairs, the open-concept layout boasts a spacious kitchen island, high-end appliances, and a seamless flow into the dining and living areas. Balconies on both levels provide stunning canal views, offering perfect spots for outdoor relaxation.The upper level offers three bedrooms and two full baths, while the lower level includes an additional primary suite, two full guest baths, a wet bar, and a secondary living area with easy access to outdoor spaces. The generously sized bedrooms feature large closets, enhancing the homes comfort and functionality.Built for durability, this home includes a standing seam metal roof, all impact windows and doors, and tile floors throughout.Outside, the property boasts two garages--one with AC--a commercial-grade ice machine, and 56 feet of concrete dockage on a desirable 90-foot canal with deepwater access. A 20,000-pound boat lift is included, along with ample parking for vehicles and trailers. Theres even room for expansion if you wish to add more dockage or a pool. This home checks all the boxes and is move-in ready! Call today for more information.

Exquisite Canal Front Retreat in Prestigious Port Antigua, IslamoradaWelcome to your dream waterfront oasis in the highly coveted Port Antigua community of Islamorada. This meticulously remodeled 5-bedroom, 3-bath (3 Up / 2 Down) residence embodies luxury coastal living with 100 feet of premier dockage, offering effortless access to Florida Bay, Channel 2, and Channel 5, placing the Atlantic Ocean just minutes away.This turnkey masterpiece has been completely redesigned and built with high-end finishes and state-of-the-art craftsmanship. On the exterior you have board & batten downstairs and hardy board upstairs. Step inside to soaring high ceilings, driftwood tile flooring with clean lines, hurricane-impact windows and doors that flood the home with natural light while framing breathtaking sunrise views.The gourmet designer kitchen is a chefs delight, featuring sleek stainless steel appliances, a professional-grade hood, wet bar with wine cooler and custom cabinetry, creating an elegant and functional space for entertaining. Each bathroom is a statement of sophistication, boasting exquisite decorator designs, while built-in custom closets and all-new interior finishes enhance the homes refined aesthetic.The outdoor living spaces are just as impressive, this oversized pie-shaped lot on the canal is a rare find, ensuring privacy and abundant space for waterside relaxation. There is room for a pool and all the poolside entertaining space one could yearn for. Residents of Port Antigua enjoy exclusive community amenities, including a private beach with tiki huts and BBQ grills, a boat ramp, and access to the Port Antigua sandbar, where endless days of sun-soaked adventure await.Whether youre seeking the perfect boaters paradise, a serene Florida Keys retreat, or an entertainers dream, this exceptional home offers it all. Experience waterfront luxury at its finest - schedule your private showing today!