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

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.

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 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!

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!

Unobstructed SUNSET/BAY views. Tucked away on a secluded point in the prestigious Sunshine Estates community on Plantation Key. Expansive property. Well built CBS home designed to enjoy bay views from essentially every room in the house. 4 Beds 4.1 Baths. Vaulted ceilings finished with wood beams. Refinished custom oak wood floors, corian kitchen countertops, dummy waiter, marble bathrooms/bedrooms, built in shelving and and uniquely designed glass block to reflect the colored sunsets. Large floating wood deck surrounded by lush foliage ; for morning coffee or catered events. Ground level consists of covered parking & rec room/maid quarters w/cabana bath & kitchen for indoor-outdoor entertaining. Crystal clear water, fishing, lobstering, & water-sports right in your own backyard. Quick ocean access via Tavernier Creek. Centrally located to restaurants, schools, shopping, churches & hospital. This is the home you have been waiting for!**BUYER TO VERIFY ALL INFORMATION.**

This remarkable 34,000 sq ft lot on the Florida Bay is a true paradise for anyone seeking a waterfront lifestyle in the heart of Islamorada, specifically Upper Matecumbe. With expansive open water views, this property offers an idyllic setting to enjoy the natural beauty of the Florida Bay.One of the key highlights of the lot is its exceptional dockage, (65 ft), which has previously accommodated a 36-foot bertram, making it perfect for boating enthusiasts. The property also offers plenty of room for a pool and garage, allowing for a customized design that maximizes the waterfront experience. Beautiful sunsets grace the horizon, casting vibrant colors across the water and clouds creating a tranquil atmosphere for evening relaxation.The lot is also a sanctuary for wildlife enthusiasts, with an abundance of aquatic species like fish, birds, manatees and a multitude of different birds. Its a perfect canvas for your dream residence or vacation retreat.With easy access to the Atlantic Ocean and iconic spots like Alligator Reef, whether you prefer fishing, diving, or simply unwinding by the water, this property is one of the best properties on the market. Embrace the ultimate Florida Keys lifestyle in this exceptional location, where every day feels like a vacation.May also purchase the vacant lot up front that has a Market Rate TDR on it. This would make an exceptional family compound in the heart of Islamorada. Possible owner financing. ,Owner / Agent

Introducing the Sea Pearl: a rare and refined coastal masterpiece nestled on Lower Matecumbe, just four parcels from the Gulf of Mexico. This ultra-modern smart home constructed in 2016 redefines luxury Keys living, offering five spacious bedrooms, five and a half bathrooms, and over 4,100 square feet of meticulously designed and furnished interior space. Boaters will delight in 70 feet of concrete dockage with water and electric, 15,000 lb boat lift, and panoramic sunset views over a protected nature preserve across the canal--ensuring privacy and tranquility that can never be built upon. This concrete haven is fully equipped with a whole-home generator, Control4 smart system (for AC, music, lights, alarm, security cameras, TVs and more), impact windows/doors, metal roof, and a sleek glass elevator connecting all three levels. Nearly 1,500 square feet of open-air porches and patios invite you to unwind and soak in the Gulf breezes. Step inside the ground level to a welcoming foyer that opens to a sitting area, custom wet bar, Anglers room, and guest ensuite bedroom. Just beyond, enjoy a resort-style pool and built-in spa surrounded by shell stone decking that stays cool even in the height of summer. On the second level, a show-stopping modern kitchen features custom cabinetry, Brittanica Cambria quartz countertops, expansive island with waterfall edge, seating for 8, GE Monogram appliances, Viking 6-burner induction cooktop, and wine cooler--perfect for entertaining. This level also offers three additional bedrooms, including a Jack-and-Jill suite, full laundry, and half bath. The entire top floor is reserved for the primary suite: a true sanctuary with sweeping water views and open air porch, spa-like bathroom with soaking tub, glass shower, bidet, and a custom walk-in closet. With optional White Marlin Beach access, this home is the epitome of modern island elegance--where every detail has been curated for comfort, style, and the ultimate Florida Keys lifestyle.

Panoramic Bay and Sunset Views! Breathtaking Bayfront Home in Safety Harbor.Experience the stunning beauty of panoramic bay views from this exquisite bayfront home in the premier Safety Harbor neighborhood on Lower Matecumbe. This home is in pristine condition and features an irreplaceable cut-in boat slip with a composite dock on the bay ensuring that your views are not obstructed, and providing immediate bay access and quick ocean access via the two bridges at Channels 2 and 5.Inside, youll find four spacious bedrooms and three bathrooms, perfect for comfortable living. An enclosed garage for all of your fishing and diving gear. The home is equipped with a new whole house generator, ensuring uninterrupted power.Step outside and immerse yourself in resort-style living with a luxurious pool and spa, lush low maintenance landscaping, perfect for relaxation and entertaining. Enjoy breathtaking sunsets year-round from your own private oasis either at the tiki bar, the dock, or one of the two bayfront screened porches. Dont miss the opportunity to own this exceptional bayfront home in Safety Harbor. Schedule your private showing today!

A truly spectacular waterfront home with 150 feet of prime bay frontage, offering breathtaking views of some of the clearest waters in the Florida Keys. This property has undergone a complete top-to-bottom renovation with exceptional attention to detail. Solid concrete bunker with a concrete roof and impact windows & doors. Boaters will appreciate the deep-water dockage, accommodating nearly any vessel, with easy ocean access through Channel 5.The main living area upstairs features three bedrooms, two bathrooms, and a beautifully designed kitchen with high-end appliances--all framed by stunning turquoise water views from nearly every room. Downstairs, a separate guest suite includes a private bedroom, bathroom, living room, and kitchen, perfect for visitors or additional living space.A pool permit is already in place, or you can take a refreshing swim right in the bay. This home is truly one-of-a-kind--dont miss the chance to own a special piece of paradise!

Boaters Paradise in Key Largo:Where the Atlantic meets luxury living, this three-story waterfront retreat offers the quintessential Keys lifestyle youve been dreaming of. 70 feet of prime dockage and dual boat lifts (20K & 10K), your nautical adventures begins at your doorstep.Spanning three meticulously designed levels, this exceptional residence maximizes its oceanfront setting. The crown jewel is the top floor entertainment space, where a chefs kitchen flows seamlessly into an open-concept living area. Here, the Atlantic Ocean becomes your living rooms backdrop, with sweeping views that transform each sunrise into a daily celebration. Five generous bedrooms feature walk-out balconies through impact sliding glass doors, treating you to panoramic views of both the Atlantic Ocean and serene Rattlesnake Creek. The 360-degree perspectives remind you that water truly is way of life here.Luxury meets convenience with thoughtful amenities including:An elevator serving all three floors, refreshing pool and hot tub, 70 feet of protected dockageDual boat lifts, Impact windows,4.5 well-appointed bathrooms.The location strikes the perfect balance between accessibility and escape. Positioned just off the Stretch in Key Largo. Walk to local restaurants for fresh catch of the day, or lose yourself in the natural beauty of nearby Dagny Johnson State Park.This isnt just a home - its your gateway to the Florida Keys lifestyle, where every day feels like a vacation and the ocean is always calling.

Discover coastal luxury in this stunning 4-bedroom, 4-bathroom bayside paradise. With 4,144 square feet of luxurious living space, this home offers breathtaking sunset views and direct access to the sparkling waters of the Florida Keys. Indulge in spacious, open-concept living areas, perfect for entertaining guests. Retreat to one of two primary suites, each featuring a large walk-in closet and private en-suite bathroom. Ascend to the rooftop deck and be rewarded with unobstructed, open-water bay views. The property features a separate living space, ideal for in-laws or guests, offering privacy and independence. The modern kitchen boasts sleek stainless steel appliances, double oven, gas appliances and ample counter space, perfect for culinary enthusiasts. The homes durable construction with a metal roof, and impact-resistant windows and doors, ensures peace of mind. For added security and privacy, the property is fully fenced and features an electric gate. Enjoy panoramic water views and unforgettable sunsets from your private oasis. With large boat dockage, youll have plenty of room for multiple boats, jet skis and easy access to the open water for boating, fishing, and other water activities. This completely updated home offers the ultimate experience in comfort and convenience. Whether youre seeking a serene retreat or an active water lovers paradise, this home has it all. Dont miss this opportunity to own a piece of paradise.