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$4,500,000
Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 1,846 SqFt Days Listed: 77
-7.22% ($350,000) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip40ft.

Welcome to your dream retreat on the bay in Venetian Shores - the Upper Keys favorite boating neighborhood! Boaters of all kinds will love the immediate bay access and lightning-quick ocean access via Snake Creek. With breathtaking views of the Florida Bay, and a sparkling pool, its the perfect place for relaxing and soaking in the sunshine. This stunning three-bedroom, two-bath beach has undergone a massive and stylish recent remodel. Youll love the timeless, modern coastal touches including the stunning new flooring! Vaulted ceilings and huge impact windows let the sunshine in. The homes open-concept design showcases panoramic bay views from almost every room. Each bedroom offers comfort and tranquility, with the master suite enjoying its own serene water views. Nestled on a dead-end street with only 12 homes, youll enjoy privacy galore. Keep a boat on the floating dock behind the house or in your boat slip just steps away, providing easy access to the crystal-clear waters of the Florida Keys. Whether youre looking for a peaceful escape or an active waterfront lifestyle, this property has it all--privacy, luxury, and unparalleled access to the best of Islamorada. Dont miss this rare opportunity to own a piece of paradise! Metal roof, impact windows and doors & artificial turf make maintenance a breeze. Electric fence. Boats to 40 and lifts allowed!

$4,600,000
Lower Matecumbe
Mat Ocean Beach   - MM: 75.00
4 Bed, 4 Baths, 2,624 SqFt Days Listed: 45
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp

This beautiful home / compound has not One, but TWO dwellings! Situated on Large Pristine oceanfront parcel ( of nearly one acre , including 20,000 SQF of submerged land , extending 200 feet into the seamlessly clear waters of the Atlantic Ocean) for the ultimate Florida Keys resort feel. This completely renovated 4 BD/ 4 BA home has endless water views, pool, brand new tiki hut, observation dock, boat ramp, and beach!

$4,721,000
Lower Matecumbe
Port Antigua   - MM: 74.05
5 Bed, 5 Baths, 4,463 SqFt Days Listed: 235
-9.58% ($500,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,None,Boat Lif

This exceptional Port Antigua residence, located on a tranquil cul-de-sac, boasts over 220 feet of concrete dockage including two boat lifts and a davit. As you enter through the exquisite hand-carved mahogany doors, youre greeted by a welcoming foyer with sliding glass doors that open to the pool and dock area. The elegant, curved staircase ascends to the main living area, featuring a spacious open-concept layout and a gourmet kitchen equipped with stainless steel appliances. The living side of the house includes two bedrooms, two bathrooms, and a laundry room, while a raised walkway leads to a secluded primary suite with a luxurious bathroom and an expansive dream closet. For those seeking sun and relaxation, the pool and hot tub provide the perfect retreat, complemented by a travertine pool deck and a brick-paved outdoor bar area, complete with a DCS grill and side burner. This shaded oasis is ideal for crafting tropical drinks and grilling your daily catch. Adjacent to the bar is a convenient pool cabana with a full bathroom. When its time to unwind indoors, head to the third floor, where a theater and game room await, complete with a wet bar and a popcorn machine. Two stunning stained glass windows depicting sea life add a unique touch, reminding you of the adventures that await on the water. The third floor also features a bedroom and a half-bath, along with an open lanai offering glimpses of the Atlantic. The expansive dock includes two gazebos--one for relaxation and the other for fish cleaning--along with a davit and two boat lifts, accommodating 20,000 lbs. and 12,000 lbs. Ample space between the lifts ensures room for your cruising yacht. This home is truly a unique gem in Port Antigua. Dont miss the opportunity to make it yours.

$4,750,000
Plantation Key
Plantation Key Colony   - MM: 90.00
4 Bed, 4 Baths, 4,144 SqFt Days Listed: 34
-4.04% ($200,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift

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, including CBS, 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.

$4,800,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 946 SqFt Days Listed: 14
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 55ft.

This remarkable 32,000 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, which has previously accommodated a 36-foot boat, making it perfect for boating enthusiasts. The dock can be expanded to suit your needs, providing ample space for additional vessels or watercraft. 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 aqatic species like fish, birds, manatees and a mulitude of different birds. Zoned as Residential Estate, this property allows for weekly rentals, presenting an opportunity for investment or personal use. 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 lot 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.Owner / Agent

$4,950,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 4,100 SqFt Days Listed: 51
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 70ft.

Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake creek, 70 feet of dockage, and luxurious living with 5 bedrooms and 6 bathrooms. Built with precision and modern style, this brand-new custom CBS residence boasts lush landscaping, a sparkling pool, and high-end finishes throughout.Step upstairs to find a tranquil master suite with an expansive walk-in closet, a beverage center, a large shower, and dual vanities. Three additional guest suites with private bathrooms, a spacious living area, a large laundry room, and a versatile bonus room complete the upper level, providing ample space for relaxation and recreation.On the main floor, the gourmet kitchen is a chefs dream, featuring top-of-the-line appliances, storage pantry, Taj Mahal quartzite countertops, a wine cooler, and custom cabinetry throughout. A private guest room with an ensuite bathroom is perfect for the friends and family to visit for a staycation. The open-concept main living area flows seamlessly into the outdoors where a full bath and outdoor kitchen await. Relax by the lounge pool, enjoy synthetic grass surroundings, and take advantage of the full dock.This canal-front oasis is a rare find in the coveted Upper Keys and offers the perfect blend of luxury, comfort, and convenience. Your slice of paradise awaits!

$4,950,000
Upper Matecumbe Key Islamorada
Russell Estates   - MM: 83.20
4 Bed, 4 Baths, 2,574 SqFt Days Listed: 164
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock

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.

$4,975,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
3 Bed, 3 Baths, 1,264 SqFt Days Listed: 209
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Come home to outstanding views with 109 feet of bay frontage in Lower Matecumbe Key. This cottage-style home combines all of the elements of Florida Keys charm with captivating open water views and is situated on 1.3 acres of land. Complete with three bedrooms and two bathrooms, this ground-level, and updated residence is the perfect place to entertain while basking in all of the beauty the Keys offers. Zoned residential estate, this income-producing home qualifies for weekly rentals, which provides ample opportunities for a discerning buyer.

$5,495,000
Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 2,972 SqFt Days Listed: 257
-15.46% ($1,005,000) 6 Price Changes : Last Change 8 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip40ft.

STUNNING PANORAMIC BAY VIEWS, sunsets and unparalleled privacy. This once-in-a-lifetime bay front property offers 200 feet of shoreline on Florida Bay with spectacular views. The property encompasses 2 and 1/2 lots, totaling a stunning three-quarters of an acre. The meticulously landscaped grounds, tended to by a Florida Master Gardener, provide a lush backdrop to the spacious residence. Boaters will love having a flats boat right behind the house along with TWO slips in the private marina just 800 feet from the front door. Each slip accommodates a boat to 40 LOA. Lifts allowed. Youll have immediate bay access and quick ocean via Snake Creek. At the heart of the estate, a sprawling one-level residence provides effortless living and lots of room for friends and family. An elevator provides easy access for everyone. A soaring cathedral tongue-and-groove ceilings create an airy sense of space, while oversized windows frame panoramic bay views from every angle. The living, dining, and kitchen areas seamlessly blend together, providing the perfect backdrop for entertaining or simply enjoying quiet moments with loved ones. A spacious screened porch offers a second living and dining area overlooking the bay. The primary suite boasts more breathtaking bay views and offers a peaceful retreat at the end of each day. Across the home, a separate wing awaits, ideal for hosting friends and family. Here, a large office, a cozy family room, and two additional bedrooms with en-suite baths provide ample space for guests to feel right at home. Youll find 3,000sf +/- under AC along with many, many additional outdoor living spaces. Additional square footage includes a 562sf workout room and a 1500sf garage (huge!) with a workshop and golf cart garage. Youll have PLENTY of space for cars, hobbies and storage. Almost all of the windows are impact and a 2003 5V crimp Galvalume metal roof provides peace of mind. Sellers have Army Corps and DEP approval for 60 observation pier!

$5,500,000
Upper Matecumbe Key Islamorada
Russell Estates   - MM: 83.20
4 Bed, 4 Baths, 2,574 SqFt Days Listed: 165
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock

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.

$5,995,000
Plantation Key
Plantation Beach   - MM: 87.50
5 Bed, 5 Baths, 4,014 SqFt Days Listed: 64
-4.77% ($300,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

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.

$6,125,000
Upper Matecumbe Key Islamorada
Russell Estates   - MM: 83.20
4 Bed, 4 Baths, 2,574 SqFt Days Listed: 164
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock

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.

$6,350,000
Lower Matecumbe
Lower Mat Harbor   - MM: 75.00
4 Bed, 4 Baths, 3,228 SqFt Days Listed: 540
-15.33% ($1,149,999) 3 Price Changes : Last Change 33 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin,Boat

$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.

$6,450,000
Plantation Key
Plantation Beach   - MM: 87.50
4 Bed, 4 Baths, 2,846 SqFt Days Listed: 36
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: BasinOther

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.

$6,500,000
Windley Key
Galen Beach   - MM: 85.00
8 Bed, 8 Baths, 5,760 SqFt Days Listed: 195
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

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.

$6,750,000
Upper Matecumbe Key Islamorada
The Russell Estates   - MM: 83.50
6 Bed, 6 Baths, 4,566 SqFt Days Listed: 5
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

This breathtaking three-story beachfront home boasts six spacious bedrooms and five lavish bathrooms and three living rooms, perfectly blending resort-style living with the utmost comfort. Located in a serene cove with a pristine natural beach, the home features floor-to-ceiling windows that offer stunning 180-degree panoramic views of the ocean. Every corner is meticulously designed with tasteful decor, exuding elegance while providing a personal, comfortable atmosphere. The property is in downtown Islamorada, Florida Keys, and includes a private beachfront terrace, a third-story private balcony, and a tranquil pool with a tiki hut, making it ideal for relaxation and entertaining. The outdoor spaces feature a cozy firepit, offering the perfect setting for intimate gatherings with the sound of the waves as a backdrop. As a vacation rental, this residence is a lucrative investment opportunity in a highly sought-after area. This home is a true masterpiece, offering unparalleled luxury, privacy, and breathtaking views.

$6,995,000
Lower Matecumbe
Mat Ocean Beach   - MM: 75.00
3 Bed, 3 Baths, 1,500 SqFt Days Listed: 335
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

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

$6,999,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
5 Bed, 5 Baths, 3,978 SqFt Days Listed: 90
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

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.

$7,450,000
Plantation Key
Treasure Harbor   - MM: 86.50
4 Bed, 4 Baths, 3,790 SqFt Days Listed: 17
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Southern Shore - A Modern Coastal MasterpieceNestled in an exclusive oceanfront setting, Southern Shore is a premier coastal residence offering an unobstructed, 180-degree panorama of the Atlantic Ocean. This exceptional, all-concrete estate spans 3,790 square feet of meticulously designed indoor living space, complemented by 2,580 square feet of expansive terraces for seamless outdoor living.Inside, the home features four luxurious en-suite bedrooms, each offering breathtaking ocean views. The chef-inspired kitchen is outfitted with custom floor-to-ceiling cabinetry, sleek quartz countertops, and top-of-the-line appliances. State-of-the-art smart home technology, custom-built closets, and the convenience of an elevator elevate both form and function in this sophisticated residence.The interior spaces reflect a perfect balance of elegance and comfort. With floor-to-ceiling windows throughout, the home captures the essence of the tropical lifestyle, offering stunning vistas of the ocean from nearly every room--living areas, kitchen, and bedrooms alike.The outdoor spaces of this estate are designed to host gatherings in style, featuring a rooftop deck, multiple terraces, and a luxurious pool and spa area with an outdoor shower. For boat enthusiasts, the property, all protected by a gated entry.Located within the serene Plantation Key community, this property also includes a misting system and occupies an expansive lot with direct ocean access. This is the ultimate tropical sanctuary for those seeking a premier location with unparalleled views, superior construction, and a full suite of luxurious amenities.Note: The owner is a licensed Florida real estate agent. For additional details, please refer to the full property description available in the document tab.

$7,495,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 3,019 SqFt Days Listed: 23
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift100ft.

Welcome to Bahia Bonita! This ultra-private bayfront estate in the heart of downtown Islamorada offers the ultimate combination of expansive open water views from every room plus deep-water dockage. If you have been wishing for an exceptional piece of Florida Keys paradise where natural beauty and luxury living meet storm resiliency, this solidly constructed, sustainably designed home may exceed your expectations. Begin your day by stepping out of your primary suite to your bayfront terrace and into an incomparable, second floor Infinity Edge pool. In the evening, slide open the wall of glass on the top floor to experience the brilliance of Islamoradas famous sunsets from your great room, gourmet kitchen or outdoor decks. Feel like grilling? Just one step away is an outdoor kitchen with bay view seating and adjacent dining. For stargazing, venture up the spiral stairs to the rooftop deck for a breathtaking front row seat. Built from solid concrete to withstand sustained 200 mph winds, this home also includes accordion shutters over impact glass for the ultimate defense against the elements. Outside, enjoy 250+ linear feet of open water frontage and a 100 dock with commercial-grade piles, composite decking and two boat lifts fitted with hurricane and storm surge protection. This unparalleled storm resiliency is combined with modern sustainability features including a large cistern with state-of-the-art water purification system, a grid-tied solar array and integrated Tesla Power Walls eliminating the need for a generator. Other functional luxuries built into the home are an elevator, professional camera/security system, central wet-dry vacuum system, mature landscaping and an enormous three-car garage, complete with workshop and storage. This home also boasts marble floors throughout and a spectacular floating staircase.This luxurious yet practical island estate is also within walking distance of many of Islamoradas favorite dining spots. Call today!

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 01-04-2025.
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