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Key West Homes For Sale on the Ocean Side of the Island. Oceanfront Homes

Total Listings 34
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$2,790,000
Key West
Moffats Subdivision   - MM: 2.00
3 Bed, 3 Baths, 2,309 SqFt Days Listed: 308
-17.94% ($610,000) 2 Price Changes : Last Change 126 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Price Reduced $209,000.Exquisite mid-century luxury home! Fitting for the pages of noted architectural magazines, the lavish entirely furnished home is a true masterpiece dedicated to high design style. Upon stepping into the dramatic entry, you will be immediately drawn to the spectacular kitchen with sleek accents, a full complement of premium appliances, and soaring ceilings. The main living area is spacious beyond comparison, with glass wall systems on 2 sides of the room opening to the swimming pool, elevated sun deck, and outdoor living room. Perfectly separated from other bedrooms, the master suite is a sumptuous oasis within the home that features a fetching spa like bath with rich finishings. Meticulously designed by landscape and lighting architects, the manicured grounds set a lush tropical backdrop for the 2nd bedroom suite and adjacent private patio. The 3rd bedroom opens onto the swimming pool with an outdoor shower just outside the door. Situated on a large corner lot, the estate is entirely surrounded by a privacy wall with covered parking suitable for a golf cart. Located in the Atlantic Beaches neighborhood of Key West, your choice of several popular beaches, walking and bike paths, pickleball and tennis courts, and the dog park are all nearby for you to enjoy an active island lifestyle. An extensive 3-D tour is available for your virtual showing requests.

$2,799,000
Key West
Kamien Plat #1   - MM: 2.00
5 Bed, 5 Baths, 2,703 SqFt Days Listed: 2
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

A stunning new renovation transforms this spacious elevated home to a total of 5bd/4ba plus a bonus space and is offered fully furnished with brand new coastal decor. Situated on a spacious corner parcel this home also offers multiple covered patios, maintenance free green space, a large heated pool and covered parking. An open concept floor plan welcomes you to a stunning great room, spacious kitchen overlooking the pool with a pass through window, a gorgeous dining room and a bar for entertaining. This exceptional renovation boasts 3 of the 5 bedrooms with custom ensuite baths and your choice of a master on the main or 2nd floor. This location overlooks the nature preserve and offers two beaches within walking distance with a dedicated pedestrian/exercise path. Enjoy dog park, beachfront dining or tennis/pickleball courts a short stroll away. If you are seeking a beautifully designed luxury home offered turnkey with stunning decor this one cant be beat!

$2,850,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 2,205 SqFt Days Listed: 186
-9.52% ($300,000) 2 Price Changes : Last Change 79 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

New lower price! Gorgeous move in ready, 2,205 sq ft conch style home, where historic charm seamlessly blends with modern luxury situated in the best location in Old Town. Just steps from Duval St and one block from the ocean, beach and the Southernmost Point. Priced at $2,850,000, this exquisite property offers a turn- key experience that includes a fully furnished house, in addition a Jeep Unlimited and a 6-person golf cart, making it easy to navigate the island and experience all that Key West has to offer. The ground floor has an inviting open floor plan with plenty of natural light filled rooms wrapped in Dade County pine and glorious flooring that allows for seamless flow between the living spaces, perfect for entertaining guests or simply unwinding after a day of adventure. With high ceilings and top-of-the-line finishes, every detail has been carefully curated to create a space the exudes elegance and comfort. The gourmet kitchen is a chefs dream with high end appliances generous countertops and custom cabinetry. Relax outside in the heated kidney shaped swimming pool surrounded by lush tropical landscaping or enjoy the covered pergola great for dining or shade. The 2nd floor has two double sized bedrooms with a spacious balcony with a glimpse of the ocean and Southernmost House. There is also a marvelous grand foyer with space for a small office. The 3rd floor master suite offers ultimate privacy encompassing the entire third floor which has a huge walk in closet with built in dressers drawers with quartz counters and lots of storage. The lavish master bathroom has a spa shower with a luxury rainfall shower head system. Double marble sink vanities, Vintage reclaimed wood walls and luxury vinyl flooring. While preserving its historic character, this home has been thoughtfully updated with modern amenities. Dont miss this opportunity to own a historic residence in Key Wests highly sought after neighborhood. Call today for your private showing

$2,950,000
Key West
Monroe Investement Co Subdivi   - MM: 2.00
4 Bed, 4 Baths, 3,656 SqFt Days Listed: 191
-15.71% ($550,000) 4 Price Changes : Last Change 104 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Beautifully renovated mid-century home in the heart of Key West. This property is sited on a 9510 sq ft lot and offers a large in ground pool with 28 ft custom waterfall. This spacious 4BR+den home is ideal for guests and entertaining with large chefs kitchen, open living and dining area with impact rated sliders opening to pool area. Brand new kitchen with cabinet space galore, walk in pantry, wet bar with beverage fridge & glass washer, commercial refrigerator/freezer, built-in ice maker, induction range, double ovens and more. Split bedroom layout is a dream for guests including a main level en suite plus upper level luxury primary bedroom suite. Three bedrooms, 2.5 baths plus den on main level. Upper level boasts cathedral ceilings, primary bedroom with en suite full bath, and large dressing room/closet. Upper level living and additional kitchen space opens to the private rooftop deck with tree top views. Two laundry rooms, tankless water heaters, 3 NEW central AC units, and more! Heated pool, impact windows and doors. NEW electrical and plumbing, irrigation system, landscape, wifi extenders for both levels. Expansive outdoor areas for relaxing poolside, grilling, reading/dining under the covered porch, or swimming laps. Outdoor shower and half bath off pool area. Garage and driveway parking for autos or water toys. Offered furnished!

$2,995,000
Key West
Old Town Unlisted   - MM: 1.00
4 Bed, 4 Baths, 3,009 SqFt Days Listed: 135
-3.23% ($100,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Indulge in the pinnacle of luxury at this stunning three-story Old Town Key West residence, a property that simply must be seen. Located directly across from the historic Key West Lighthouse and just steps from the renowned Duval Street, this home offers unparalleled access to Key Wests finest attractions. A leisurely stroll takes you to the Southernmost Point and the Atlantic Ocean, mere minutes away. Located in the coveted X Flood Zone, one of Key Wests highest elevation points and boasting over 3,000 square feet of meticulously designed living space, including four bedrooms and four bathrooms featuring two master suites, this home effortlessly blends sophistication with contemporary comfort. The first floor showcases a generous eat-in kitchen, a versatile guest bedroom or sitting room, and two full bathrooms, while the expansive great room provides an ideal retreat for relaxation or entertainment. French doors open to reveal a spacious in-ground pool, perfect for enjoying refreshing breezes and ample outdoor space. The second and third floors house two additional master suites, each offering privacy and opulence. Embrace a lifestyle of refinement and coastal allure in this exclusive Key West haven. Ideally situated for walking or biking to renowned restaurants, enjoying live music, exploring galleries, spending the day at Fort Zachary Taylor State Park or savoring the vibrant energy of Duval Street.

$2,999,500
Key West
Mills Place   - MM: 1.00
2 Bed, 2 Baths, 1,770 SqFt Days Listed: 678
-6.12% ($195,500) 1 Price Change : Last Change 265 Days Ago
Townhouse - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Vacation rental Ocean and Harbor view unit in Truman Annex. Beautiful sunset vistas of the Atlantic and the Gulf while also overlooking the the tropical and lush grounds of Truman Waterfront Park and Truman Harbor. This residence features a large covered balcony right off the main living area with living room, dining room and kitchen. The second storys primary bedroom and bath opens out to its own private balcony. Highly desirable Old Town location in Mills Place condominiums in Truman Annex.

$3,199,000
Key West
Prog Land Imp Co Diag   - MM: 2.00
9 Bed, 9 Baths, 4,037 SqFt Days Listed: 114
-5.21% ($176,000) 1 Price Change : Last Change 24 Days Ago
Multi-Units - Active - Waterfront No
Side of Island: Ocean - Dockage: None

PRICED TO SELL. Discover Key West Quirk and versatility with this one-of-a-kind mid-century mansion/multi-family/cozy compound, i.e., whatever you decide to make of it. Whether you desire a primary residence with plenty of space for your guests, owner-tenant shared space, rental income, or a redevelopment opportunity with room to expand, the options are endless.Having previously received an award from Old Island Restoration of Key West, this home exhibits time period specific charm. The current owner has embraced the history of the house which was once home to a local artist and continued the appreciation of the propertys retro artistic flare. Upon entering your vibe will be transported back in time and every detail will tell a nostalgic story.The property comprises 3 units situated on an impressive nearly 12,000 square foot lot only 3 blocks from the beach. Each unit includes a separate entrance and private gated yard lined with tropical foliage. Additionally, there is a central courtyard that may be used as a common space. The main house consists of 4 bedrooms and 3.5 baths with a combo entertainment area that overlooks a massive green space and private luxurious heated pool. This allows the ultimate indoor-outdoor feel, and it is the ideal entertainment space for the bash of your choice. The lavish primary suite presents a grand garden view. The second unit offers 3 bedrooms, 2 baths and a tranquil outdoor shower. Exposed beams and skylights cast a pleasant hue on the living space.Lastly, the third unit encompasses 2 bedrooms and 2 baths with similar aesthetics and an expansive outdoor patio.With tons of storage space, youll have room for all your belongings and more. Enjoy the convenience of off-street parking and security of this concrete block home armored with impact windows and doors.Dont miss this rare chance to own a multi-functional piece of Key West history! Schedule a showing today to explore the limitless possibilities.

$3,499,000
Key West
Vista Del Mar   - MM: 4.00
4 Bed, 4 Baths, 2,426 SqFt Days Listed: 37
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift80ft.Concre

Welcome to an unparalleled waterfront experience in one of the most coveted locations in Key West. where every day feels like a vacation! Located on the prestigious Riviera Canal, this one-of-a-kind four-bedroom, two-bath haven is more than just a home--its a boaters dream, a sunseekers paradise, and the ultimate in indoor-outdoor luxury living.Imagine waking up each morning in the heart of this island gem, with 80 feet of wide canal frontage just outside your door, complete with a 20,000 lb boat lift and davit ready for your larger vessel. Whether youre setting sail for a day on the water or simply soaking up the tropical vibes, this home puts you right where the action is.Designed by the famed Bender & Associates, this 2,426 sq. ft. retreat was built to blend the best of coastal living with modern comfort. The split floor plan gives everyone their own space to unwind, while the open-concept living area beckons you to gather and celebrate the good life. With wall-to-wall sliding glass impact doors and travertine floors throughout, your living space seamlessly merges with the outdoors, bringing in natural light and the gentle canal breeze.And speaking of the outdoors... step into your own private oasis! A sparkling pool, surrounded by meticulously maintained landscaping, is the perfect spot for a lazy afternoon dip. Prefer a sunset barbecue? Your covered outdoor dining and lounge area sits on sleek travertine floors, with plenty of space to relax rain or shine.The kitchen is a showstopper, featuring quartz countertops, custom cabinetry, and stainless-steel appliances, perfect for whipping up fresh seafood feasts or hosting cocktails at the bar with a view of the pool. The primary bedroom is the ultimate retreat, with its own seating area and French doors that open right onto the pool deck. Additional features include a whole-house Generac generator, impact windows and doors throughout, and a gated circular driveway that offers complete privacy.

$3,695,000
Key West
Sunset Key   - MM: 0.00
3 Bed, 3 Baths, 1,920 SqFt Days Listed: 118
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This is the ultimate living experience. You get all Historic Key West has to offer, but are tucked away on your own private island paradise. Access to Sunset Key is by the island ferry which runs 24 hours a day, but is only a 4 minute boat ride. Have all the fun you can stand in Key West, but then come home to absolute peace and quiet. Have your own Sunset Party from your covered roof top observation deck. The island has all the conveniences of a world class luxury resort, including three beaches within a minutes walk, a full service spa, golf cart parking, gourmet restaurant, tennis courts, and much more. Ample covered parking is available at discounted rates in the Opal Resort parking garage. For a truly unique and eye opening experience, call now and make an appointment for a private grand tour of the island. You will be glad you did!

$3,799,000
Key West
Gwynn Subdivision   - MM: 1.00
5 Bed, 5 Baths, 2,960 SqFt Days Listed: 43
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 Beachs, 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.

$3,850,000
Key West
Riviera Shores   - MM: 3.00
5 Bed, 5 Baths, 3,124 SqFt Days Listed: 19
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

CANAL HOME WITH MAIN HOUSE AND GUEST COTTAGE PLUS GARAGE! Waterfront home in Key West! Canal home with pool, garage and guest quarters. Spacious main house plus guest apartment with separate entrance. Expansive lot with a gated privacy fence Main house has 3 bedrooms plus a den and 3 full baths. Large light filled rooms for entertaining including grand foyer, dining room, and the perfect living room with walls of windows showcasing canal & water views! Kitchen has wood flooring, built-in cabinets, stainless steel appliances and leads to the dining area. Kitchen opens to breezeway to garage, laundry room and courtyard. Bedrooms offer large closets and two have private access to pool/decks.. Primary bedroom suite has double closets, en suite bath and pool /water views. Central AC, terrazo flooring, laundry room, cedar lined closets, and garage.Upstairs guest suite has a 2 bedroom/1 bath apartment with kitchen and balcony with tree top canal views. Plenty of room for boat and auto parking. Lovely decked areas for relaxing poolside or enjoying the canal views while dining. Kayak from your backyard! Large lot 104x130 fenced and secluded with no neighbors on other side of the canal.

$5,275,000
Key West
Old Town Unrecord   - MM: 1.00
5 Bed, 5 Baths, 3,148 SqFt Days Listed: 173
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Investment opportunity! Weekly rentals are allowed! Nestled within the highly sought-after Truman Annex in Old Town Key West, 202 Admirals Lane exudes coastal charm and luxury living at its finest. Boasting 5 bedrooms and 4 full bathrooms, this meticulously maintained residence showcases beautifully renovated bathrooms and a private pool oasis, offering an idyllic retreat for residents and vacationers alike. Situated nearby the iconic Duval Street and the tranquil expanse of Fort Zachary Taylor State Park, this home epitomizes the quintessential Key West lifestyle. Upon entering, youre greeted by an inviting main living area, adorned with French doors that effortlessly blur the lines between indoor and outdoor living. A sun-drenched sunroom, encased in glass doors, is the perfect setting for relaxation or entertainment year-round. Additional living spaces abound, including a bright and airy sitting room. The main floor is thoughtfully appointed with a convenient full bathroom, ensuring comfort and convenience for guests. The 2nd level offers 4 bedrooms and 3 full baths and the ensuite 3rd floor is great for guest . Included is a Truman Annex transient rental license allowing for weekly rentals, 202 Admirals Lane presents a lucrative investment opportunity as a successful vacation rental. Rare for Key West, this home features a coveted 2-car garage, providing secure parking and storage, a coveted amenity for sure. Offered turnkey, the residence comes complete with all furnishings and future reservations, promising a seamless transition for discerning buyers or investors seeking the ultimate Key West retreat.

$6,500,000
Key West
The Foundry   - MM: 1.00
3 Bed, 3 Baths, 4,200 SqFt Days Listed: 254
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This distinguished estate, erected in 1904, proudly stands as the revered historic landmark known as Building 11, The Smithery within the esteemed confines of the Truman Annex--an exclusive gated community formerly part of the United States Naval Station, Key West. This exceptional offering epitomizes expert restoration, boasting lofty ceilings, majestic 22 brick exterior walls, and imposing wooden beams that seamlessly marry historic allure with contemporary finesse upon an expansive, idyllic plot. A quintet of majestic arched French doors adorns the facade, beckoning vistas of the verdant tropical surroundings. The ground level unfolds with sweeping travertine floors adorned with artisanal fixtures, housing a gracious great room with a bespoke bar, a gourmet kitchen, an elegant dining area, and additional living space. Nestled on this level, a guest suite seamlessly extends to the inviting poolside retreat, graced with a cascading waterfall and tranquil stone deck. Ascending to the upper level reveals an enchanting realm, where the primary and guest suites are interconnected by a captivating gallery bridge, each enveloped in luxurious amenities and adorned with custom built-ins, sumptuous hardwood flooring, and exquisite lighting fixtures. Lavish bathrooms, featuring opulent upgrades, adorn both wings, ensuring unparalleled comfort and refinement. Exquisitely maintained, this abode has garnered the admiration of a select few, its architectural brilliance cherished by those fortunate enough to experience its splendor. The expansive carport, a newly fashioned storage enclave echoing the original architectural charm--further enhances the allure of this hidden treasure. Nestled amidst illustrious neighbors, including Trumans Little White House this jewel epitomizes one of the most coveted addresses within the Florida Keys, offering a lifestyle of unrivaled sophistication and allure.

$18,500,000
Key West
Filer Boyle Subdivision   - MM: 1.00
5 Bed, 5 Baths, 4,008 SqFt Days Listed: 143
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

Discover the epitome of unique luxury in the Florida Keys with the REAL Southernmost House of the Continental United States of America, a property that perfectly blends history, elegance, and an unrivaled location. Positioned adjacent to the iconic Southernmost Point buoy, where the Atlantic Ocean meets the Gulf of Mexico, this concrete 4,008-square-foot home stands as a landmark at the southernmost edge of the Continental United States on a large 17,000 sq. ft. lot. This exceptional property is the beloved home of renowned and honored American Artist, SEWARD JOHNSON and his wife. Johnson is famous for his life size figurative sculptures which are exhibited in public spaces locally (Marilyn Monroe at our Tropic Cinema) and internationally. This multi-family designated home boasts five bedrooms and five and a half bathrooms. Enjoy the charm and elegance of a historic home with modern amenities. As you enter through the front door into a formal living room, you are transported back to the Hemingway era. The formal living room opens up to a Florida room with tropical vibes, and glass sliding doors lead to the pool area. The home also features sealed coral stone flooring. From the living room, an elevator leads to the upstairs primary bedroom and two guest bedrooms, surrounded by a large balcony with endless vistas over the property and the Atlantic Ocean.Enjoy swimming in a beautiful large 50 x 20 ft. pool and the spacious outdoor lounging area with Ocean breezes. Bird watching will be your new favorite pastime. With its unique location, this property offers unparalleled ocean views and proximity to all of Key Wests vibrant attractions. Southernmost Beach is on the on the same block, with its sandy beach and restaurant. The property is equipped with a coveted transient license, allowing for nightly rentals, making it a prime investment opportunity for vacation rentals or a lavish private residence. THE Southernmost House is a rare gem in the heart of Key West.

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 11-26-2024.
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