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

The Islands of Islamorada Beach Club is a meticulously designed private gated enclave offering waterfront single-family residences. With every comfort considered, this residence exudes coastal living with four bedrooms, four and one-half bathrooms, and stunning ocean views. The three-floor villa offers 3,137 sq ft of interior and 930 sq ft of exterior contemporary island architecture with an open, airy, and light-filled design. Three bedrooms are king-sized with en-suite bathrooms; the fourth is a twin room. Additionally, the residence is being offered fully furnished with artwork from local Florida artists. Residence amenities include a top-of-the-line kitchen, open-concept kitchen, dining, and living spaces, elevator, a powder room, ample closets, two oceanfront balconies, a ground floor waterfront loggia, a laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. This turn-key home is maintenance-free, providing the possibility of passive income. The safe and secure environment within the club allows for effortless multigenerational vacations with a gated entry and attentive staff. The Beach Club delivers a luxurious experience with its 615 ft of pristine crescent-shaped swimming beach and a private boat basin with ample dockage. Enjoy two oceanfront pools, an oceanfront bar, and pickleball courts for some friendly competition. Golf enthusiasts can practice their swing at the unique driving range that extends into the ocean. The well-equipped fitness center caters to health enthusiasts, while children can have fun in the dedicated play area. Surrounded by lush, mature landscaping, the Beach Club also provides a plethora of water activities, allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this area set it apart as a secluded destination.

Experience the lavish charm of the Florida Keys in this meticulously crafted 5-bed, 5-bath,with an office that can be converted into a 6th bedroom. This 4,822 sq. ft. home designed with your comfort in mind. Ideal for large families, it boasts spacious interiors, elegant high ceilings, and 8 ft. door openings. A grand entrance reveals a vast private fenced yard, equipped with 2 electric gates and an intercom system for seamless communication. Adorned with stylish pavers, the yard includes a heated pool and jacuzzi area.Approaching the main entrance, discover car garages on either side with electric doors and a car porch, each featuring a private 36 keyed door. Enter the foyer to find a striking staircase or opt for the 8 ft. tall elevator, leading to the main floor or a guest room with pool access. The main floor boasts an elegant living and dining room with a 20 ft. ceiling and breathtaking bay water views. The kitchen features an original Benihana cooking station, top-of-the-line appliances, and ample storage, accompanied by a spacious laundry room. Two guest bedrooms with a bathroom complete this level.Ascend to the third level, revealing a master suite with a spacious bathroom, his and hers walk-in closets, an office, and a media room with surround sound. The pinnacle of luxury awaits on the 2,500 sq. ft. rooftop, offering 360-degree views, including stunning bay and sunset views. Accessible via stairs, it boasts tasteful balconies for a delightful experience.For boating enthusiasts, the property features a Bayfront 225 ft. pier with a 25,000 lbs. boatlift and ample space for watercraft. Live the life of opulence in this Florida Keys retreat!

The Islands of Islamorada Beach Club is a meticulously designed private gated enclave offering waterfront single-family residences. With every comfort considered, this residence exudes coastal living with four bedrooms, four and one-half bathrooms, and stunning ocean views. The three-floor villa offers 3,137 sq ft of interior and 930 sq ft of exterior contemporary island architecture with an open, airy, and light-filled design. Three bedrooms are king-sized with en-suite bathrooms; the fourth is a bunk room. Additionally, the residence is being offered fully furnished with artwork from local Florida artists. Residence amenities include a top-of-the-line kitchen, open-concept kitchen, dining, and living spaces, a powder room, ample closets, two oceanfront balconies, a ground floor waterfront loggia, a laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. This turn-key home is maintenance-free, providing the possibility of passive income. The safe and secure environment within the club allows for effortless multigenerational vacations with a gated entry and attentive staff. The Beach Club delivers a luxurious experience with its 615 ft of pristine crescent-shaped swimming beach and a private boat basin with ample dockage. Enjoy two oceanfront pools, an oceanfront bar, and pickleball courts for some friendly competition. Golf enthusiasts can practice their swing at the unique driving range that extends into the ocean. The well-equipped fitness center caters to health enthusiasts, while children can have fun in the dedicated play area. Surrounded by lush, mature landscaping, the Beach Club also provides a plethora of water activities, allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this area set it apart as a secluded destination.

Isla del Sueno - Isle of dreams. Live on your own peninsula with over 700 feet of concrete dockage on deep water access straight out to the ocean. This magnificent Tavernier home is nestled on nearly an acre of land, this exquisite property offers a rare amount of waterfront situated on its own peninsula, providing privacy and great marina view. Imagine inviting all your friends to your yacht party on your peninsula. Deep-water access leading directly to the open ocean or easy bay access too --perfect for the avid boater or water enthusiast.This stunning concrete 5-bedroom 5 bath home is thoughtfully designed with:Main Level: Two ensuite bedrooms, two additional guest bedrooms, and two guest baths, offering ample space for family and guests.Guest Quarters: A separate one-bedroom, one-bathroom suite on the ground floor with direct access to the pool area, ensuring privacy and convenience.The property is an entertainers dream, featuring:Two 2-car garages and abundant parking to accommodate all your vehicles and toys.A wraparound balcony and two covered waterfront terraces to enjoy the breathtaking views, ocean breezes, and year-round shade.A pristine pool area perfect for relaxing after a day on the water.This homes location offers sweeping vistas of the water and marina, creating a serene ambiance that feels like a world of its own. Whether youre seeking tranquility, adventure, or a little of both, Isla del Sueno is the ultimate Florida Keys retreat.Dont miss the chance to live your dream--schedule your private showing today!

THE BEACH HOUSE ON SUNSET ROAD! Enjoy both sunrise & sunset from your own backyard in the Florida Keys! Welcome to a unique point of land on Florida Bay, offering two lots with almost an acre of land, a quarter-acre bay bottom and features over 200 feet of waterfront, a remodeled multi-story concrete home, a resort-style pool, dockage for multiple boats, and a sandy beach with sea oats creating an idyllic setting for enjoying the parade of boats and marine wildlife meandering by. The remodeled beach residence is situated on the southernmost lot, while the resort-style pool, framed by palm trees, is positioned on the northern lot. A gated entry and driveway lead guests to panoramic open water views across the pool and from the two-story, 4-bedroom, 2-bathroom home on two living levels. The main living level includes a kitchen, dining area, two guest bedrooms, and a full bathroom, plus three sets of French doors opening to an outside covered entertaining area. Interior stairs lead to the second living level with a vaulted tongue-and-groove open beam ceiling, a living/media room, side sitting parlor, third guest bedroom, primary suite, and an expansive upper deck for an even greater birds-eye view of the Bay. The waterfront area includes a concrete seawall, two concrete piers, a cut-in boat slip/basin for added protection, a large Chickee Hut with picnic table, two smaller boat ramps for launching paddleboards/kayaks, and a sandy beach with wade-in beach entry. A myriad of mature palms encircles the home and pool. At night, enjoy the lighted palms as they sway in the tropical breeze, providing the ultimate backdrop for your own personal resort. This one-of-a-kind point of land on the island of Key Largo is perfectly situated to not only enjoy the most colorful sunsets by night but also the captivating early morning sunrises. Enjoy your beachfront paradise or create your vision by constructing a larger estate offering great investment potential. The choice is yours!

This stunning property spans 1.82 acres and is ideally located on the ocean in the heart of Islamorada, Florida Keys. A gated entry welcomes you leading to a Royal Palm-lined circular driveway up to a portico providing a grand entrance. Upon entering the foyer, the wrought iron staircase sets the stage for the impressive interior.With five spacious bedrooms and four well-appointed bathrooms, this residence offers ample space for family and guests. Enjoy stunning ocean views from various vantage points within the home, enhancing the comfort and breathtaking natural beauty. The observation dock provides a perfect spot for relaxation, while the saltwater pool equipped with heater/chiller, ensures year-round enjoyment. Added features are quartz countertops, top-of-the-line appliances and the Residential Estate zoning allows weekly vacation rentals with a high-income stream.This combination of amenities creates an inviting atmosphere that reflects the privacy and charm of the Florida Keys lifestyle.

The Islands of Islamorada Beach Club is a meticulously designed private gated enclave offering waterfront single-family residences. With every comfort considered, this residence exudes coastal living with four bedrooms, four and one-half bathrooms, and stunning ocean views. The three-floor villa offers 3,137 sq ft of interior and 930 sq ft of exterior contemporary island architecture with an open, airy, and light-filled design. Three bedrooms are king-sized with en-suite bathrooms; the fourth is a twin room. Additionally, the residence is being offered fully furnished with artwork from local Florida artists. Residence amenities include a top-of-the-line kitchen, open-concept kitchen, dining, and living spaces, a powder room, ample closets, two oceanfront balconies, a ground floor waterfront loggia, a laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. This turn-key home is maintenance-free, providing the possibility of passive income. The safe and secure environment within the club allows for effortless multigenerational vacations with a gated entry and attentive staff. The Beach Club delivers a luxurious experience with its 615 ft of pristine crescent-shaped swimming beach and a private boat basin with ample dockage. Enjoy two oceanfront pools, an oceanfront bar, and pickleball courts for some friendly competition. Golf enthusiasts can practice their swing at the unique driving range that extends into the ocean. The well-equipped fitness center caters to health enthusiasts, while children can have fun in the dedicated play area. Surrounded by lush, mature landscaping, the Beach Club also provides a plethora of water activities, allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this area set it apart as a secluded destination.

$400,000 PRICE REDUCTION !! ... Welcome to Serenity Cove, a remarkable, comfortably luxurious estate set along the shores of the Florida Bay. This custom-designed property, stretching from the highway to the bay is almost 1.75 acres. It is perfect for those who value peace, relaxation, and the simple joys of what the Florida Keys has to offer.This home offers four bedrooms and four bathrooms and 110 of dock with multiple slips accommodating up to a 45 boat with 5 draft and 16k lift. This home has been thoughtfully designed with tasteful moldings, and warm, inviting finishes. The kitchen, is equipped with top-tier appliances, custom cabinetry, and a roomy island - perfect for those who love to cook and entertain. It smoothly transitions into the formal dining room, making it an ideal space for both quiet family dinners and larger celebrations.The second-floor suite, with its spacious layout, welcoming fireplace, and private balcony, is the ultimate retreat. The en-suite bathroom, has a dual vanity, a claw-foot soaking tub, and a walk-in shower, guarantees moments of relaxation.The first floor offers a smart design with separate living areas and bedrooms. The 1st floor suite includes a steam shower and a reinforced safe room that doubles as a walk-in closet. The additional two bedrooms and a den with surround sound and a wet bar are comfortably located on the opposite side of the home.Enjoy quiet moments on the covered patio or engage in lively gatherings around the spacious poolside patio, which leads directly to the sandy beach for amazing sunsets. Here, youll find ample seating, a fire pit, a Boat House and steps leading to the basin for swimming and exploring the Bays unique ecosystem.Serenity Cove is comfortably tucked away from the hustle of US1, offering a sense of privacy and security, while maintaining easy access to schools, shopping, dining that make Islamorada so desirable.

Welcome to the ultimate tropical sanctuary in Key Largo! An extraordinary waterfront estate spanning over 2.5 acres along Tarpon Basin. This breathtaking property offers unparalleled sunset vistas, a coral jetty framed by a lagoon, a boat ramp, lush mangroves, and a canopy of majestic mahogany trees.Green sloping land is elevated for privacy and optimal protection . The estate features two impeccably remodeled homes with high-end finishes. The main house includes three bedrooms, four elegantly appointed bathrooms, a full kitchen, and spacious living areas. The second home offers two beautifully crafted bedrooms, two luxurious bathrooms, and a full kitchen. Both homes are adorned with lavish spa-like bathrooms and hand-carved, imported Bali doors and casings.The Suburban/Commercial Zoning offers limitless investment possibilities, or a private sanctuary, a high-end vacation rental, an exclusive event venue, or a family compound. Imagine creating an oversized dream home surrounded by tropical splendor.Just 65 minutes from Miami International Airport, this one-of-a-kind estate is perfect as a peaceful hideaway, a lucrative income property, or a stunning family compound. Create your private sanctuary and embrace the essence of the Florida Keys lifestyle.

An incomparable bayside Islamorada compound with an exempted deep-dredge boat basin, this enchanting property provides 100 of direct waterfront and .7 acres of professionally manicured mature grounds. Move-in ready 4-bedroom residence offered for only the second time in a generation also provides an opportunity to build a one-of-a-kind property in the coveted Plantation Beach estate area. Enter via a gated entrance with stately mature mahogany trees and towering palms to your own private retreat. The serene and private sanctuary includes a saltwater infinity pool, complete with a spa, heater, and chiller. With year-round direct sunset views, enjoy golden hour evenings lit with tiki torches and landscape lighting throughout. This two-story above-flood traditional keys home offers four bedrooms and three full baths, with an interior staircase that includes separate quarters and an extra kitchenette - an ideal layout for family living or hosting guests. Additional features include a whole house generator, a security system, a spacious garage, and dolphin swim-bys. The neighborhood offers a homeowners park with a boat ramp, beach, and picnic area. It is on a quiet street amongst prestigious estates in a most desirable Plantation Key neighborhood.

Exceptional waterfront living with amazing open water views over looking Barnes Sound. A quick jaunt to Miami yet this tropical oasis feels like youre on your own private island estate. 60 concrete dock on a protected inlet for your boats and other watercrafts . Over 4100 sq ft of living area over 3 levels in a thoughtfully laid out floor plan with elevator access, wrap around decks, plus a rooftop terrace for sunning and entertaining with jaw dropping views. 3 suite Bedrooms, Study (or 4th BR) 3.5 Baths, Exercise Room, 2 extra deep garages, an expansive screened lanai on the ground level and terraces on the 2nd & 3rd levels.

Brand New Ocean Front Family Estate. Be the first to own these 2 new gorgeous sister home. Enjoy daily sunrises, exciting ocean views, all while relaxing in the luxury of 2 quality built coastal homes. Combined 8 Beds/ 6 Baths provides room for the whole family. While sharing the identical footprints and layouts these homes each present different stylish tiles and cool color palettes. Both homes feature 5 star chef kitchens, elevators, porcelain tiles throughout, flawless T&G ceilings, and Brizo faucets. Step outside and soak up the warm sun and take a dip in the 2nd floor elevated concrete pools or unwind and enjoy the the endless cool ocean breezes.Great location to enjoy active ocean views of local sandbars, Snake Creek, kite surfing, and Alligator Lighthouse. **Dockage available at very close by marina.** Active permits from DEP and Army Core to build 295 Observation Pier through mangroves. These homes are a must see in person. Top quality finishes throughout that will surly impress. ** Seller Financing Possible** Each home may be purchased individually.

Open Oceanfront Estate with Deep Water Dockage on 1.5 Acres on Millionaires Row... Islamoradas premier address. New dock with two boat lifts (16,000 lb. and 10,000 lb.) to enjoy one of the best boating locations in the Keys, plus a 4,103 s.f. home with 4 bedrooms, 3 full baths, a large heated pool, winding private driveway, and a soaring central atrium surrounded by walls of windows to frame the ocean view. Open ocean views from the living room, Florida room, porches, master bedroom and upstairs loft. Living room with wet bar and pass-through window to the gourmet kitchen and separate dining room, all with Saturnia stone floors. Direct boating access to the best offshore fishing and diving, plus quick Florida Bay access. RE Zoning allows weekly rentals for great income potential. The sandy backyard is shaded by palms and the large pool is fenced for privacy. The winding drive from the gate to the home is dotted with seating spots for enjoying the wildlife and tropical foliage. There is also a separate storage room and workshop downstairs, a gardening shed and landscape lighting along the driveway. Call today!

Experience the perfect blend of elegance and tropical charm in this exquisite luxury home in Islamorada. This four-story residence offers breathtaking bay views from every level and features over 70 feet of protected dockage with immediate bay access and quick ride to oceanside via Chanel 2 or Channel 5 bridge, perfect for boating enthusiasts. With four bedrooms and four and a half baths, the spacious layout includes three laundry rooms and an elevator for convenience. The outdoor area boasts a heated and chilled pool with limestone decking, built in grill, custom wet bar, and a covered living space ideal for entertaining. The chefs kitchen features luxurious quartz countertops, top-of-the-line appliances, and a stylish glass tile backsplash. The expansive primary suite occupies the entire fourth floor, complete with a private sitting room, balcony, and a luxurious en-suite bath. Each bedroom also has its own balcony to enjoy stunning sunsets. Additional highlights include impact windows, a fully air-conditioned tackle room/workshop and garage, and can accommodate a 42 RV with sewer and 50 amp service. Beautifully landscaped with Royal Palms and tropical plantings, this home offers the unique opportunity to enjoy upscale Keys living with modern amenities and glorious water and sunset views. Perfect for those seeking a turnkey property in an idyllic location.

Beautiful adjoining oceanfront gated estates available individually or together for a reduced price! Each parcel has a single family residence with vacationrental income potential and are zoned Suburban Commercial for development opportunities.*UPDATE: There are 50 TDRs (TREs) available, reviewed by Monroe County and transferable to these parcels for higher development potential! This unique wooded acreage has a deepbasin and channel for ocean access, with dolphin piling boat slips and boat ramp. Single Family Residences with ROGO exemptionsfor remodel/rebuild possibilities. Highest approval rate via Monroe County is for MIXED-USE COMMERCIAL development. (The 6.1acre parcel may be sold together with contiguous 3.2 acre parcel@95325 Overseas Hwy, AK#1592986,RE#00483360 000000 13 6238 PT TR 5&6 SOUTHCLIFF ESTS PB2-45 & PT GOV LOT 1 & ADJ BAY for grand total of 9.36 acres, includes 1137 sf 1970 2/1 cbshome, metal roof.) This is a duplicate listing. Broker part owner/family owned.

Sunset Haven This absolutely delightful and serene Florida bayfront beauty will take your breath away the moment you walk in. Delightful double primary ensuite layout and open porches and patios galore adorn this fresh feeling home. 180 degree open water views complete nightly with painted sky sunsets and the best boating proximity; just a stones throw to the Intracoastal waterway and both Tavernier Creek and Snake Creek for easy Bay to Ocean access. 108 of protected dockage with ramp, boat lift and tiki, ample parking and plenty of room for a pool if you need one.

Beautiful 300 of oceanfront property on Lower Matecumbe Key. This offering consists of two 100 lots, vacant & contiguous, a 100 lot with a triplex apartment building, and 2 additional Transferable Development Rights. This gives you endless possibilities for redevelopment of the property. The two vacant lots have an additional 200 of bay bottom. Fantastic 180 ocean views make for gorgeous sunrises on the naturally sandy beaches. View Alligator Lighthouse, watch dolphins, manatees, and birds feeding on fish right in front of you. At night, beautiful full moon risings, cruise ships with their lights passing, and plenty of stars. Launch kayaks from the beach to do a little tarpon fishing and bonefish are making a comeback so you can wade with your fly rod for a thrill. Also snorkel for lobster in season in all the little crevices and holes off shore of the property.Recap: 300 of oceanfront made up of 2 vacant lots, 1 lot with 3 apartments, bay bottom on the vacant lots, and 2 additional transferable building rights.Note: One of the owners is a State of Florida Real Estate Licensee

Discover unparalleled privacy and tranquility in this one-of-a-kind oceanfront estate, a true sanctuary nestled amidst the untouched beauty of the Florida Keys. Tucked behind a private gate, the estate begins with a scenic drive through acres of pristine, preserved nature, leading to your own private island. This secluded haven, like no other in the Florida Keys, was once a source of inspiration for Budd Post--the visionary engineer behind the legendary Card Sound Road. It offers an extraordinary blend of history, natural beauty, and modern luxury.Surrounded by breathtaking 360-degree views, the propertys expansive decks and waterfront tiki hut provide unmatched solitude and serenity. Here, you can reflect on days spent exploring the unspoiled waters of the Florida Keys, far removed from the bustle of everyday life.Crafted to perfection, the estates concrete construction ensures strength and resilience while maintaining an air of timeless elegance. Inside, cathedral ceilings and a grand limestone fireplace create a warm and sophisticated ambiance. The dining room, framed by panoramic ocean views, offers an intimate setting for unforgettable gatherings. Three en-suite bedrooms promise unmatched comfort and privacy, making the home as functional as it is exquisite.Boasting over 130 feet of concrete dockage, the estate is a boaters dream, offering the perfect gateway to explore the azure waters that surround you. Whether pursuing nautical adventures or savoring the peace of waterfront living, this property delivers an exceptional experience.This private haven is truly like no other in the Florida Keys--a rare gem where luxury, seclusion, and nature converge. Every corner of this secluded retreat invites you to embrace the unparalleled charm of coastal living in an enchanting and one-of-a-kind setting.

Welcome to Southwinds, your exclusive oceanfront oasis in the heart of Lower Matecumbe, Islamorada. This stunning 5-bedroom, 6.5-bath CBS home embodies luxury and tropical living. Spanning nearly 4,000 sq. ft., Southwinds offers breathtaking ocean views, with floor-to-ceiling impact windows that flood the interior with natural light, seamlessly connecting you to the stunning beauty of the Atlantic. One of the standout features of Southwinds is its 100 natural sandy beach, a rare find in Keys oceanfront homes. Stroll the 150 foot pier which features water, electric and a fish cleaning station. Read a book or enjoy your favorite beverage under the tiki. The pool features a spillover edge, bubbler, sun shelf and hot tub. The grand outdoor Mahogany bar is ideal for entertaining against the backdrop for the ocean breezes. A private pickleball court offers hours of fun and fitness for you and your guests, right in your own backyard. Paired with a putting green, this home provides a truly unique lifestyle experience that caters to the active, outdoor enthusiast.The home features a large kitchen with a pass-thru, an induction range, wine and beverage coolers, and two sets of washers and dryers for ultimate convenience. The third-floor wet bar and expansive open balconies offer additional space to enjoy the spectacular views. The gated property also features landscape lighting, an irrigation system, a spacious garage, and storage room.Southwinds is a sanctuary for those seeking a private retreat or a valuable investment. Whether youre in search of a second home or a high-performing rental property, this residence offers everything you could desire. Zoning allows for weekly vacation rentals, Southwinds presents an ideal opportunity for generating rental income.

Discover your dream retreat in this beautiful oceanfront home, set on 1.5 acres of prime beachfront property with 150 feet of pristine white sandy beach, this is the ultimate getaway for relaxation and adventure.Unwind in the oversized heated pool or customized hot tub after a day of sun and fun. The Tiki Hut provides convenient storage for all your water toys, making your boating and beach days effortless. Enjoy practicing your swing on the private putting golf course, all while surrounded by breathtaking ocean scenery.With a lucrative 7-day rental option and an easily obtainable license, this gem is perfect for both personal enjoyment and investment. Dont miss your chance to own this slice of paradise--schedule a viewing today!