Divider
Content Divider

Florida Keys Homes For Sale on the Ocean Side of the Island. Oceanfront Homes

Total Listings 605
Order By:

$3,480,000
Marathon
Sombrero Properties   - MM: 49.50
4 Bed, 4 Baths, 4,262 SqFt Days Listed: 107
-1.97% ($70,000) 1 Price Change : Last Change 37 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 67ft.

Experience the ultimate Florida Keys lifestyle in this stunning canalfront concrete home situated on an expansive parcel, just a few steps from the iconic Sombrero Beach! Designed for resort-style living, this property boasts a luxurious pool area complete with a heater and chiller, swim-up bar, cabana, and spa . A paved pathway leads you to a second infinity pool, offering sweeping views of lush landscaping. Enjoy 67 feet of deep-water dockage, providing easy access to the Atlantic Ocean for world-class offshore fishing and diving, plus proximity to the Florida Bay for fantastic backcountry fishing!The interior of this spacious home features an expansive foyer with soaring ceilings, setting the stage for elegance throughout. The first floor offers an open-concept design with a gourmet kitchen, generous living area, and a master suite with a private veranda. An ensuite guest room and a half bathroom for guests complete the main level.Upstairs, the grand staircase leads to a second spacious living area with wet bar, second master suite and bath, along with another ensuite guest room, providing ample space and privacy for family and friends.In addition this amazing property offers a turn key rental with excellent rental history available.Whether youre looking to entertain or relax in paradise, this beautifully designed home is the perfect blend of luxury and function--offering the best of the Florida Keys!

$3,499,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,472 SqFt Days Listed: 103
-9.70% ($375,900) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Welcome to the most exceptional home and premier lot currently available in the prestigious Sugarloaf Shores neighborhood. This property is a masterpiece of luxury, craftsmanship, and natural beauty, offering a lifestyle that truly must be experienced in person to be fully appreciated.Situated on an expansive 13,000+ square foot private point lot, this home boasts over 230 feet of crystal-clear waterfront, providing unmatched panoramic open-water views. Facing west, the property delivers daily breathtaking sunsets over gin-clear turquoise waters--a sight that no other lot can compare to.Completely remodeled with no detail overlooked, the home features an open-concept design with brand-new stainless steel appliances, quartz countertops, and elegant warm tile flooring throughout. The spacious master suite opens to a covered porch, while the living rooms fully pocketing sliding doors blur the line between indoors and outdoors. Over 550 square feet of covered porches create an ideal space to relax and take in the stunning surroundings.The exterior is equally impressive. A brand-new custom concrete pool, both heated and chilled, includes a built-in spa, while the yard is entirely landscaped with turf and river stone accents for easy maintenance. Boaters will love the 15,000 lb boat lift, kayak pier, and the newly thatched tiki hut with a fan for shaded relaxation.Practicality meets peace of mind with impact hurricane windows and doors paired with roll-down or accordion shutters, a new roof, and spray foam attic insulation. The lower level features over 1,100 square feet of enclosed space, including a workshop and extra-height garage door for storing small vessels on trailers.Located just 20 minutes from Key West Airport, world-class restaurants, and shopping. With its one-of-a-kind views and unmatched design, privacy, and location, this property stands as one of the finest offerings in the Keys today.

$3,499,000
Cudjoe Key
Cudjoe Acres   - MM: 21.50
6 Bed, 6 Baths, 4,976 SqFt Days Listed: 14
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Experience the epitome of island luxury in this custom built 5,000 sq. ft. CBS estate, where masterful design, refined finishes, and breathtaking ocean views come together in perfect harmony. Situated on over an acre of prime oceanfront land, this gated and walled compound offers the ultimate in privacy, serenity, and sophisticated coastal living. Step into the light-filled, open-concept Great Room, where walls of impact doors frame sweeping views of the Atlantic Ocean. Designed to impress, the heart of the home is the chefs kitchen featuring custom concrete countertops, top-of-the-line appliances, and a layout that blends functionality with effortless entertaining. The main residence includes 4 generously sized en-suite bedrooms, all thoughtfully designed to provide a seamless balance of comfort and elegance. The expansive primary suite is a true retreat, offering stunning ocean views, a spacious layout, and a spa-inspired bath. Each guest suite is tastefully appointed to create a tranquil, private experience. For added versatility, a separate 2 bedroom guest house, complete with private entrances, serves as an ideal mother-in-law suite or a luxurious space for extended family and guests to enjoy their own secluded oasis. Step outside into your own resort-style paradise and entertain in style with a summer kitchen, multiple lounging areas, and an elevated pool featuring a waterfall, swim-up bar, and submerged seating. With over an acre of lush tropical grounds and direct oceanfront access, this property is a dream for water enthusiasts, anglers, and watersport lovers alike. This rare offering is more than a home, its an extraordinary lifestyle defined by luxury, privacy, and the natural beauty of the Florida Keys. A truly unique opportunity that must be experienced to be fully appreciated.

$3,499,000
Marathon
Tropic Island   - MM: 50.00
5 Bed, 5 Baths, 3,491 SqFt Days Listed: 202
-10.28% ($401,000) 2 Price Changes : Last Change 17 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift80ft.

Luxurious, Modern masterpiece with incomparable boating just minutes to Sombrero Beach! Every detail has been considered in this immaculate 5-bedroom, 5-bathroom concrete built home, with impact doors/windows, in the heart of exciting Marathon! Unpack and relax, this turn-key home comes furnished and equipped for immediate enjoyment! Currently utilized as a successful vacation rental, this exceptional property is an ideal investment property or serene private oasis for personal use. Take advantage of deep-draft boating with world class fishing and diving just minutes away. The sprawling 80 composite dock comes equipped with 20K boat lift (2021), fillet station, water and electric service. After a day on the water, cool off in the resort-style pool boasting heater, chiller, sun deck, and paver pool deck! Built for elevated waterside entertaining with nearly 1000 Sq. Ft. of covered verandas, complete with tongue-and-groove ceilings and stunning canal views! Inside, this contemporary home offers two spacious floors and every modern convenience! The first floor comes complete with the first of two spacious living areas, convenient attached 2-car garage, laundry room, cabana bathroom, den with wet bar, and private en suite guest bedroom. Ascend the modern staircase with wrought iron railing and custom chandelier into an open-concept great room on the second floor, boasting separate dining and living areas and expertly-equipped Chefs Kitchen. Entertain for the masses with ample cabinetry, Cambria quartz countertops, high-end Cafe appliances, and large island with counter seating, additional storage, sink, and waterfall edge. Two additional guest bedrooms ensure elevated accommodation for visitors while you retire to an opulent primary suite with walk-in closet, additional closet, palatial en suite and Juliette balcony. Neighborhood offers beautiful Sombrero Beach, golf at Florida Keys Country Club and waterfront restaurants and marinas.

$3,499,000
Marathon
Farara Shores   - MM: 52.00
6 Bed, 6 Baths, 2,243 SqFt Days Listed: 29
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 150ft.

Welcome to your dream waterfront retreat in the heart of the Florida Keys! This stunning 6-bedroom, 6-bathroom pool home in Marathon offers the perfect blend of luxury, comfort, and investment potential.Situated on an expansive 150 feet of deep-water dockage, this property is a boaters paradise, with easy access to the Atlantic Ocean and the Gulf of Mexico. Whether youre setting sail for a day of world-class fishing or cruising to nearby islands, this homes premier location ensures smooth sailing.Designed for both relaxation and entertainment, the home boasts an open-concept living space with breathtaking water views, a gourmet kitchen, and spacious en-suite bedrooms. Step outside to a tropical oasis featuring a resort-style pool, ample patio space, and a covered outdoor entertaining area--perfect for enjoying the Florida Keys lifestyleThis property also delivers excellent vacation rental income, making it a fantastic investment opportunity. With strong rental demand in Marathon, this home is an ideal choice for investors looking for a high-performing rental property or a luxurious personal retreat with income potential.Dont miss out on this rare deep-water waterfront gem in the Keys--your slice of paradise awaits!

$3,500,000
Key Largo
Ocean Isle Estates   - MM: 106.00
4 Bed, 4 Baths, 3,024 SqFt Days Listed: 72
-5.41% ($200,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift70ft.Concre

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!!

$3,500,000
Key Largo
Southcliff Ests   - MM: 95.00
2 Bed, 2 Baths, 1,137 SqFt Days Listed: 233
Multi-Units - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

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

$3,500,000
Marathon
Grassy Key   - MM: 58.90
4 Bed, 4 Baths, 3,013 SqFt Days Listed: 364
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

SeaGlass Cove is a brand-new luxury, gated island community located in the heart of the Florida Keys adjacent to Duck Key. A rare find of just 14 new construction residences offering four and five-bedroom floor plans all with direct Atlantic Ocean views, a resort style pool, pickleball court, sandy beach, and the flexibility of a weekly rental. The first floor offers a private two car garage and covered cabana with spacious outdoor living space that leads out to the private beach and pool deck. The second floor features an open floor plan with spacious kitchen, dining and great rooms all overlooking the Atlantic Ocean. One en-suite bedroom on this floor provides seclusion for guests. On the top floor youll find the primary suite with luxurious spa bath and three additional guest bedrooms. The homes are finished with high end KitchenAid appliances, waterfall quartz countertops, full height backsplashes, custom closets and much more. Additionally this residence offers upgrades including: elevator, outdoor summer kitchen, exterior spiral staircase to first floor, custom millwork, brass fixtures and fire pit. SeaGlass Cove is barefoot luxury at its best.

$3,650,000
Big Pine Key
Piney Point Subdivision   - MM: 29.50
4 Bed, 4 Baths, 2,050 SqFt Days Listed: 235
-3.69% ($140,000) 1 Price Change : Last Change 5 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Slip,Boa

Welcome to Tarpon Cove, an exclusive, resort-like retreat nestled on a sprawling estate lot in the heart of Big Pine Key. This recently renovated home offers a perfect blend of modern elegance and natural beauty, surrounded by the pristine flora and fauna of the Florida Key Deer Preserve. With four spacious bedrooms and three and a half bathrooms, this unique multi-level residence is designed for those who appreciate the finer things in life.As you approach the gated entrance, a long, driveway, shaded by mature native trees, leads you to this private oasis. The fully fenced yard offers complete privacy and is beautifully landscaped with tropical foliage. Designed with both luxury and durability in mind, this concrete home features a metal roof and impact-resistant windows and doors, ensuring peace of mind in any weather.Step inside to find an open-concept living space that flows effortlessly from room to room, all bathed in natural light and offering stunning views of the surrounding landscape. The modern kitchen is a chefs dream, complete with quartz countertops, a Samsung Bespoke appliance package, and a professional-grade gas cooktop. Whether youre entertaining guests or enjoying a quiet meal, the beauty of the Florida Keys is your constant companion, with breathtaking water views from almost every room in the house.Outdoors, the expansive dockage provides incredible boating access on the ocean side, with ample space for multiple boats. This property is a boaters paradise, offering direct access to the sparkling waters of the Atlantic. Additional amenities include RV hookup, covered parking, and garage storage, making this home as practical as it is beautiful.Tarpon Cove is not just a home--its a lifestyle. A rare and special property, it offers the tranquility and seclusion of a private resort, right in your own backyard. Discover the magic of the Florida Keys and make Tarpon Cove your ultimate escape.

$3,699,000
Key Colony
Coury Subdivision   - MM: 53.50
6 Bed, 6 Baths, 2,990 SqFt Days Listed: 18
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift50ft.

Luxurious waterfront single-family home with expansive canal views nestled in a prime location with breathtaking panoramic views. This completely remodeled six bedroom, four bathroom estate is the epitome of luxury living. Fully renovated in 2022, this stunning home combines elegance, comfort, and sophisticated design with no detail overlooked. Upon entry, you are greeted by a grand, oversized foyer featuring well-concealed storage to keep everything organized and out of sight. A short flight of sleek, glass-railed stairs leads you to the main living level, where open-concept spaces and natural light fill every room. From the moment you step inside, youll be captivated by the rich beauty of Italian plank tile that flows seamlessly throughout the home, creating an atmosphere of refinement. The spacious layout is perfect for grand entertaining and serene relaxation, with expansive living areas inviting you to enjoy every inch of this exquisite space. The chefs kitchen features top-of-the-line appliances, custom cabinetry, and a large island ideal for preparing meals or gathering with loved ones. Each of the four bathrooms is designed with elegance in mind, featuring high-end finishes and modern fixtures that create an atmosphere of pure luxury. Step outside to your slice of paradise: a 50-foot Trex dock perfect for docking your boat or simply enjoying the view and a large saltwater pool with an attached spa to unwind while taking in the surrounding beauty. This home is not just a residence; its a lifestyle. Whether lounging by the pool, taking in the sunset over the canal, or entertaining guests in one of the many open-concept living spaces, this property offers unparalleled luxury. Dont miss your chance to own this waterfront masterpiece - schedule your private showing today!

$3,700,000
Duck Key
Plantation Island   - MM: 61.00
4 Bed, 4 Baths, 3,166 SqFt Days Listed: 108
-1.33% ($50,000) 1 Price Change : Last Change 11 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift82ft.Concre

Exclusive Duck Key Waterfront Retreat with Breathtaking Ocean ViewsExperience the pinnacle of coastal living in this exceptional open-water home on Duck Key. Designed to capture stunning ocean vistas and mesmerizing sunsets, this 4-bedroom, 3 bathroom gem offers the perfect balance of luxury, comfort, and outdoor paradise.Expansive Living Areas: Open-concept design featuring a gourmet kitchen with granite countertops, spacious dining, and living areas perfect for entertaining or relaxing by the water.Panoramic Views: Two large enclosed porches provide year-round enjoyment of ocean breezes and views. Ascend the spiral staircase to a rooftop deck with 360-degree vistas - a perfect spot for sunset cocktails.Unmatched Convenience: The home includes a dumbwaiter shaft for effortless transport of groceries or luggage, plus a solid oak staircase leading from the grand foyer.Outdoor Haven: A private tiki hut offers shade and tranquility, while the 15K boat lift caters to boating enthusiasts. Theres also ample space to add a pool for the ultimate outdoor escape.Exceptional Storage & Garages: Two oversized garages provide plenty of room for vehicles, watercraft, and more, with additional storage throughout the home for all your needs.Meticulously Maintained: This home has been lovingly cared for inside and out, offering a move-in-ready opportunity to enjoy life on Duck Key.Situated in one of the Florida Keys most sought-after locations, this property is a dream come true for those seeking serene surroundings, endless water views, and the best of island living.Schedule your private showing today and make this coastal retreat your forever home!

$3,750,000
Key West
Key West Investment Co Subdiv   - MM: 1.00
4 Bed, 4 Baths, 3,257 SqFt Days Listed: 81
-3.60% ($140,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Spectacular home in what is arguably Key Wests finest Casa Marina neighborhood. 3,257 square feet (nearly twice the size of a typical Key West home) of high-end finishes around the corner from Dog Beach and Louies Backyard and a short walk to Duval. Exotic woods, marble, granites, soaring ceilings, and tropical ambiance are found throughout. A giant chefs eat-in kitchen (500 sq ft!) with marble floors, Arctic blue ice granite countertops, vaulted pine ceilings, and an outdoor deck is an entertaining dream. Huge formal living room, a sunny family room that opens to the pool deck and stone waterfall. A large and beautiful full second kitchen and a 2 bedroom renovated guest wing with a full private bath round out the main floor living spaces. Two separate and massive upstairs Master Suites with vaulted cedar ceilings (masterpieces unto themselves) and large closets provide unparalleled sleeping quarters while the rear Master has a balcony overlooking the pool. Two spacious attics offer ample storage. Built like a fortress with hurricane and termite-repellent materials, this gorgeous home was recently rebuilt to last and no flood waters this century have reached its doors. All five bathrooms feature marble tile from around the world. The house has two LEGAL units to be used as a duplex (with separate entrances), or a very spacious single-family home (with up to 6 bedrooms). Mother-in-Law suite, or nursery wing on main floor. The backyard oasis provides a peaceful, tropical setting to relax and unwind--off-street parking for three cars. A must-see villa that must be seen to be fully appreciated; catch it while you can. One of the owners is a Florida Licensed Realtor and the Listing Agent.

$3,750,000
Key West
Gg Watson Subdivision   - MM: 1.00
5 Bed, 5 Baths, 2,721 SqFt Days Listed: 103
-16.67% ($750,000) 3 Price Changes : Last Change 50 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Luxurious Old Town Key West Oasis with separate Guest House! Nestled in the heart of Key Wests historic district, this impeccably remodeled property redefines island elegance. Situated in the coveted X Flood Zone, this home boasts an unparalleled location just steps from iconic Duval Street, world-class dining, vibrant galleries, and pristine beaches. Step inside to discover a light-filled sanctuary where 14-foot cathedral ceilings crown an expansive open-plan living, dining, and chefs kitchen area. French doors seamlessly blend indoor and outdoor living, inviting you to a private paradise. The spacious kitchen features Caesarstone Quartz countertops, a Sub-Zero refrigerator, a Wolf gas range, Fisher & Paykel double-drawer dishwasher, beverage drawers, and a microwave drawer. Outdoors, indulge in Key West living at its finest with a sparkling heated swimming pool, a large deck for entertaining and sunbathing, a serene waterfall, and lush tropical landscaping. A covered sitting area offers the perfect spot to unwind. There is a Sonos sound with Focal low-profile speakers to fill the air with your favorite tunes throughout the main house. The main house features two guest rooms, a shared bathroom and a washer and dryer conveniently located between them, and a luxurious primary suite with its own washer and dryer. Impact windows and doors ensure peace of mind, while privacy fencing and off-street parking for two cars provide unmatched convenience. A super cute, separate guest house completes this property, offering two ensuite bedrooms, a kitchenette, a dining area, and a loft sitting space--perfectly positioned at the back for ultimate guest privacy. A storage shed for pool toys and tools ensures everything has its place. This Key West masterpiece is a rare gem, blending timeless charm with modern luxury. Dont miss the chance to own your own slice of paradise in this superb location! Easy to show! Video link https://n9.cl/1114packer

$3,795,000
Key Colony
Coury Subdivision   - MM: 53.50
5 Bed, 5 Baths, 2,741 SqFt Days Listed: 181
-1.43% ($55,000) 1 Price Change : Last Change 77 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits30ft.

180 13th St, Key Colony Beach. Welcome to your dream home in the heart of Key Colony Beach. This stunning 5-bedroom, 4.5-bath canal-front home, built in 2022, offers modern coastal elegance and top-tier features, making it a true waterfront paradise. Boasting 80ft of water frontage, a 30ft composite dock, and 5ft control depth on a 100ft wide canal, this home provides easy access to both the Ocean and Gulf, perfect for boating enthusiasts.Step inside through the show-stopping Echo pivot door into a sunlit foyer with soaring 10ft ceilings. The spacious, open-concept living area greets you with 12ft ceilings and expansive accordion glass doors that blur the lines between indoor and outdoor living. Enjoy seamless flow from the living and dining areas to the covered porch, outdoor kitchen, and a heated/chilled pool--all perfect for entertaining or relaxing. Take the stairs to the rooftop sundeck and savor breathtaking water views.The gourmet chefs kitchen is a masterpiece, featuring Dolomite countertops, an expansive center island, and premium appliances, including a Miele induction stove top and Liebherr refrigerator. The abundant cabinetry provides ample storage, while the design and finishes elevate the heart of this home.The split-bedroom layout offers privacy, with the luxurious primary suite featuring two walk-in closets and porch access. Two ensuite bedrooms are perfect for guests, while a poolside bedroom provides access to a full bath. The home also includes a 5th bedroom, currently used as a private office, laundry room, powder room, and easy 2 stall garage access.With 7-day vacation rentals allowed, this property is ideal for generating lucrative rental income. Located near beaches, parks, golf courses, tennis courts, and top-tier dining, this home invites you to experience the true Florida Keys lifestyle. This property could be sold turnkey--dont miss your chance to own this incredible waterfront retreat. Contact me to schedule your private tour

$3,795,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 3,086 SqFt Days Listed: 251
-15.57% ($700,000) 3 Price Changes : Last Change 17 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Exquisite Open Water Estate on Prestigious Southpoint, Sugarloaf Key! Experience unparalleled luxury at this stunning solid concrete open water property, located just 20 minutes from the magic of Key West and Key West Airport. Situated on prestigious Southpoint, Sugarloaf Key, this magnificent estate offers breathtaking open water views and a lifestyle of elegance and comfort.Spanning 3,086 square feet of refined living space, this home features 3 bedrooms, 2 bathrooms, plus a versatile office/den and a large laundry room. The expansive 19,300 square foot lot is a tropical paradise, beautifully landscaped with fruit trees, an orchid house, landscape lighting, and irrigation from cisterns.Step inside to discover poured concrete floors that exude modern sophistication. The chefs kitchen is a culinary dream, equipped with Miele appliances and a Sub-Zero refrigerator. Entertain with ease in the separate bar area and enormous living space. The property also boasts a ducted vacuum system and a commercial-grade metal roof for added convenience and durability. Outdoor living reaches new heights with a stunning new pool, featuring a long ledge perfect for relaxing with cocktails. The large tiki hut serves as an outdoor lounge, complimented by a separate bar area under the house adjacent to the pool. The dock and boat lift provide direct access to the open water, making this home a boaters dream. Enjoy the convenience of an elevator, granting access from the garage and ground level to all floors. The rooftop deck offers 360-degree views, including vistas of the open ocean, perfect for sunset soirees or stargazing nights. This estate is designed for the discerning luxury buyer, offering the perfect blend of sophistication, comfort, and tropical charm. Dont miss the opportunity to own a piece of paradise on Sugarloaf Key! Low Insurances. Call for your private showing today! Video tour https://tinyurl.com/16705Tam

$3,799,000
Key West
Gwynn Subdivision   - MM: 1.00
5 Bed, 5 Baths, 2,960 SqFt Days Listed: 190
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Introducing Blu on White one of Key Wests most stunning historic single level residences in desirable Old Town Key West. Exceptional location scoring a full 10 on the walkability scale with easy access to the beaches, White St. Pier, an array of galleries, restaurants and cafes.Taking full advantage of the generous 5800 sq ft. lot, this 5BD/4BA home offers so much space and versatility with almost 3000 sq ft. of interior living space. Currently configured as a 4BD/3BA main house with a separate 1/1 apartment with private entrance. The apartment is perfect for a nanny, mother in law and also offers an excellent source of income as it comes with a transient license which will permit nightly rentals. Current owner operates the apartment as a nightly vacation rental and numbers can be provided upon request. The main house is currently being operated as a monthly vacation rental with a strong rental history and excellent future bookings, which will convey with the sale.Originally two historic shotgun homes, this home has been expertly merged to create a breathtaking great room addition that overlooks the stunning saltwater pool and garden. Featuring a high vaulted ceiling with post and beam design, wide plank wood floors, skylights for additional natural lighting, built-in bookshelves and large impressive impact sliders creating an enviable ambiance you will never want to leave.Prepare to be captivated by the heart of the home, the luxuriously appointed kitchen, crafted with the finest materials & unparalleled design, this culinary haven is perfect for any aspiring chef and those who love family gatherings, with gas Viking stove & appliances, European style open shelving, excellent prep space and large interior dining area. Additional features include oversized saltwater pool, private tropical landscaped garden and cozy shaded Gazebo, storage shed and so much more.The epitome of a fine Key West Historic Home combining luxury and versatility

$3,800,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
4 Bed, 4 Baths, 2,519 SqFt Days Listed: 147
-10.59% ($450,000) 2 Price Changes : Last Change 26 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

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

$3,945,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
4 Bed, 4 Baths, 3,817 SqFt Days Listed: 136
-17.80% ($854,000) 3 Price Changes : Last Change 11 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift150ft.Concr

Exquisite LUXURY Waterfront Estate in the prestigious Cudjoe Gardens. A STUNNING TURNKEY PARADISE, SOLD AS IS WITH HIGH END DESIGNER FURNISHINGS & DECOR FROM RESTORATION HARDWARE, POTTERY BARN, & SERENA AND LILY. ALSO 2 HOBIE CATS. This Custom Built Home with a total of 5,373sf under roof is a masterpiece blending luxurious design with the serene beauty of the Florida Keys. Built on a sprawling waterfront ELEVATED corner lot of 16,500sf with 260FT of water frontage and deep draft. This gorgeous property offers an unparalleled tropical lifestyle, perfect for those who demand the best in comfort and elegance.Property Highlights4 Bedrooms + Office/Studio: Spacious, sunlit rooms designed for relaxation and productivity, including a versatile office or creative studio space which could be a 5th Bedroom.4 Full Bathrooms: Impeccably designed with high-end fixtures and finishes.Gourmet Kitchen: A chefs dream, featuring state-of-the-art appliances, custom cabinetry, and expansive Quartz countertops ideal for entertaining.Imported Italian & Moroccan Flooring: Stunning, high-quality flooring that enhances the luxurious ambiance throughout.12-16 Ft Ceilings: Create an open, airy feel while showcasing architectural sophistication.Saltwater Pool: Dive into the generously sized, chilled & heated concrete pool with water feature, lights and lounging platformOutdoor Kitchen: Stainless Steel Appliances, Spacious layout, Perfect for entertaining.2 Boat Lifts, 20k and 10kAdditional Amenities3 A/C Units: Individually climate-controlled zones, including the 3-car garage for comfort and convenience.Full Property Generator, 1000 gallon Propane Tank, Full Security System, Phantom SunShades for Screened in PorchThis meticulously designed property combines sophisticated interiors with exceptional outdoor living spaces. Located in a prime area of Cudjoe Key, this home offers privacy, stunning water views, and direct access to the pristine waters of the Lower Key

$3,950,000
Duck Key
Yacht Club Island   - MM: 61.00
4 Bed, 4 Baths, 3,295 SqFt Days Listed: 117
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift75ft.Concre

Welcome to your ultimate waterfront sanctuary in the heart of the Florida Keys. This stunning home in Duck Key offers a perfect blend of luxury and durability, with no detail spared in the design. Built in 2022, this home surpasses the latest building codes and is crafted to withstand the test of time. Inside, youll find a spacious living area with custom-made contemporary furniture. The Poggenpohl kitchen boasts top-of-the-line Miele appliances, including a combi speed oven, combi steam oven, induction cooktop, and a wine climate cabinet. The four bedrooms and three and one half bathrooms are fully equipped, with spa-like features such as rain showers, glass doors, and sleek Dornbracht faucets. The primary suite has its own bathtub, body shower, and private sundeck. The 35-foot high concrete rooftop offers 360-degree views of the island, canal, and ocean, perfect for sunbathing, stargazing, or hosting a party. The downstairs outdoor space is finished with AZEK(r) composite decking, making adding an outdoor kitchen to the covered area easy. Boaters will be impressed by the substantial concrete dock and pilings featuring two High-Tide boat lifts: a remarkable 40,000 lb lift alongside a 6,000 lb lift currently utilized for jet skis. The dock is also equipped with electricity and water connections, and a fish prep table. Using the roller system, you can easily access your kayaks and store all your water sports equipment in the air-conditioned garage. This modern home is designed for a lifestyle of comfort, luxury, and adventure. So why wait? Make this exclusive waterfront property your own and experience the ultimate Florida Keys lifestyle. Dont miss out on this once-in-a-lifetime opportunity. Live the dream, feel the breeze, and own a piece of paradise.

$3,950,000
Marathon
Grassy Key   - MM: 58.90
5 Bed, 5 Baths, 3,011 SqFt Days Listed: 489
+3.95% ($150,000) 1 Price Change : Last Change 214 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Weekly rentals permitted! SeaGlass Cove is a brand-new luxury, gated island community located in the heart of the Florida Keys adjacent to Duck Key. A rare find of just 14 new construction residences offering four and five-bedroom floor plans all with direct Atlantic Ocean views, a resort style pool, pickleball court, sandy beach, and the flexibility of a weekly rental. The first floor offers a private two car garage and covered cabana with spacious outdoor living space that leads out to the private beach and pool deck. The second floor features an open floor plan with spacious kitchen, dining and great rooms all overlooking the Atlantic Ocean. One en-suite bedroom on this floor provides seclusion for guests. On the top floor youll find the primary suite with luxurious spa bath and the option of two or three additional guest bedrooms. The homes are finished with high end KitchenAid appliances, waterfall quartz countertops, full height backsplashes, custom closets and much more. Additionally, SeaGlass Cove offers select upgrade options including, elevator/lift, exterior spiral staircase, summer kitchen, custom millwork and Wolf/Sub-Zero appliances. SeaGlass Cove is barefoot luxury at its best.

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 04-22-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA