Key West LUXURY Homes for Sale, Single Family Houses, Florida Keys Real Estate

Total Listings 234
Key West
$12,500,000 17,500 (SqFt)
  • 5
  • 5
  • Single Family

808 Southard Street
KEY WEST, FL 33040

Old Town Unlisted   Waterfront: No MM: 0
Side of Island: Median
Dockage: None

Historic Harris School plus 6 lots and 5 ROGO units for sale. 2 story Indian Block structure built as one of the first schools in Florida. Situated on a 2 acre lot in the center of Old Town in the Solares Hill area. 3 blocks to Duval St., 5 blocks to Historic Seaport District. This unique offering does not occur in Key West often. Original classrooms boast 14 ft. ceilings (both floors). Grand staircases, lots of wood on interior of building. HNC-2 Zoning allows for residential, multi-family, offices, light commercial use, group homes, medical facilities and more. There are 7 lots (6 along Carstens Lane) with 5 ROGO units. Possible private compound use or just single family construction. Will finance with 30% down & market rates
  Details
Key West
$9,600,000 10,822 (SqFt)
  • 5
  • 4
  • Single Family

620 Southard Street
KEY WEST, FL 33040

Old Town Unrecord   Waterfront: No MM: 1
Side of Island: Median
Dockage: None

The Lowe Mansion has been relisted. It is a once in a lifetime opportunity. This home has not been offered for sale in over three decades. This majestic property stands alone in its beauty,historical significance,and quality of renovation. The privacy of this property is unparalleled. It sits on one of the largest parcels of land in Old Town amidst a magnificent tropical garden atop Solaris Hill, the highest point on the island. The estate includes the main house,private guest or caretakers house,large studio,conservatories,and numerous other structures. This opportunity is for those who desire the finest. Qualified individuals please request additional information on the home, and discuss scheduling of showings.
  Details
Key West
$5,500,000 2,987 (SqFt)
  • 3
  • 2
  • Single Family

5 Sunset Key Drive
KEY WEST, FL 33040

Sunset Key   Waterfront: Yes MM: 0
Side of Island: Bay/Gulf
Dockage: Dock Privileges,Firs

Recently listed waterfront residence on world famous Sunset Key. This waterfront beach house makes for the perfect island getaway. Located directly on the Beach with an unbelievable view of the open ocean and surrounding keys. This residence has three bedrooms with two and a half baths. The downstairs master bedroom has doors leading out to the pool area and the beach. Imagine living on your own secluded island, but being only three minutes from historic downtown Key West accessible only by an island ferry which runs 24 hours a day. On Sunset Key Island, there are no cars and no parking problems, only quiet island living with plenty of beaches, tennis courts, and resort amenities. Come see this incredible beachfront residence.
  Details
Key West
$5,400,000 3,416 (SqFt)
  • 4
  • 4
  • Single Family

20 Sunset Key Drive
KEY WEST, FL 33040

Sunset Key   Waterfront: Yes MM: 0
Side of Island: Ocean
Dockage: None

Located on the prestigious private island of Sunset Key, just 5 minutes from Key West, by launch, sits a custom built ocean front 3,416 sq.ft. compound. In the main house, on the first level you are awed by incredible views of the Atlantic. Features include dramatically high coffered ceilings, custom moldings, wood flooring, and spacious open living areas. A second floor master suite includes a sitting room, spa-sized bath, and dressing room. A pergola connects the guest cottage with the main house accented by lush tropical landscaping, free form pool, water feature and spa. The private two story guest house includes 2 bedrooms and 2 baths with the same attention to detail. Beach, spa, gym and a gourmet restaurant are there for you.
  Details
Key West
$5,300,000 2,804 (SqFt)
  • 3
  • 3
  • Single Family

33 Sunset Key Drive
KEY WEST, FL 33040

Sunset Key   Waterfront: Yes MM: 0
Side of Island: Bay/Gulf
Dockage: Dock Privileges,Firs

Unbelievable three bedroom Waterfront residence on an oversized lot. Incredible views of Key West Harbor from the private waterfront pool and open balcony. Attention to detail was not overlooked in the construction of this private island residence. Sip your favorite beverage while watching the tall ships sail past on their way to their Sunset Celebration cruises or Swim in the refreshing clear blue waters from any of the three beaches within walking distance to this home. Tennis Courts, a Gourmet Restaurant, and many more features give homeowners and their guests a remarkable living experience. City utilities and services, island ferry running 24 hours a day, and other conveniences make this place a modern island paradise
  Details
Key West
$4,850,000 4,333 (SqFt)
  • 5
  • 5
  • Single Family

324 Whitehead Street
KEY WEST, FL 33040

Old Town Unlisted   Waterfront: No MM: 0
Side of Island: Median
Dockage: None

Historic Truman Annex Naval Officers home, circa 1906, featuring 5 bedrooms each with its own ensuite bathroom. Classic front double porches grace the facade of this home, one of the most grandiose in Old Town Key West. Home has been extensively restored to feature a chefs kitchen, formal sitting room, spacious dining area, media room, and guest cottage with large indoor/ outdoor living room not included in living square footage. Master suite boasts a sun-filled sitting room that serves as its entrance. Spacious guest rooms and closets throughout. Over 1000 sq. ft. covered decks and porches. Property has off-street parking via the gated access of Truman annex, yet offers an entrance off Whitehead Street for easy walking access.
  Details
Key West
$4,800,000 5,210 (SqFt)
  • 11
  • 5
  • Single Family

700 Thomas Street
KEY WEST, FL 33040

Old Town Unlisted   Waterfront: No MM: 0
Side of Island: Ocean
Dockage: None

Financing Available. Private gated compound located (2) blks from center of Duval St. One of the largest residential parcels in Old Town Key West. Corner property w/ 210 of frontage along Thomas/ Angela Sts.(5) existing residential rental units, approved plans & permit to build a new (2) story, 6th residence on corner. (6) water/ sewer/ solid waste accts. Heated pool w/ Jacuzzi, sundeck, BBQ, heated Jacuzzi, laundry, mature native trees, palms, orchids, irrigation system, ground lighting, exterior sound system, ADT security system, 24 hr. CCTV system, brick walkways. Compound setting has great potential for a private estate, retreat, vacation rentals, condo conversion, or interval ownership. Owner will consider trades - 1031 or other.
  Details
Key West
$4,245,000 5,585 (SqFt)
  • 5
  • 5
  • Single Family

744 Windsor Lane
KEY WEST, FL 33040

Old Town Unlisted   Waterfront: No MM: 0
Side of Island: Bay/Gulf
Dockage: None

Incomparable recently renovated home on an estate sized lot in the heart of the historic district. The secluded home is sleek and modern with a large open floor plan including a showplace kitchen, a lavish master suite, three guest bedrooms with gorgeous ensuite bathrooms, large artist studio, multiple covered porches and spectacular outdoor living area with built-in kitchen. The expansive gardens are beautifully landscaped with meandering paths and one of the largest residential pools in Key West. This well designed private Old Town oasis embraces the indoor/outdoor Key West lifestyle with walls of sliding glass doors and lots of windows.
  Details
Key West
$3,795,000 3,820 (SqFt)
  • 5
  • 5
  • Single Family

906 Johnson Street
KEY WEST, FL 33040

Martello Towers   Waterfront: No MM: 1
Side of Island: Ocean
Dockage: None

Luxury meets location on the coveted & peaceful Johnson Street of the Casa Marina District. A rare opportunity awaits to enjoy 3820 sqft in a sprawling parklike setting. You will marvel at the large open spaces that grace this home both inside & out. Beautifully appointed 5bd/6ba + studio. Two 1bd guest suites enjoy exterior entrances, mini kitchens, full bath & living areas. Walled for privacy & beautifully landscaped with large pool complimented by outdoor kitchen for the ultimate in entertaining. 3 blocks from the beach, tennis courts & dining. This unsurpased combination is not to be missed.
  Details
Shark Key
$3,700,000 6,228 (SqFt)
  • 5
  • 4
  • Single Family

55 Two Turtles Lane
KEY WEST, FL 33040

Shark Key   Waterfront: Yes MM: 11
Side of Island: Bay/Gulf
Dockage: None

Perfection awaits you in this elegant 5 bedroom/4.5 bath Shark Key Estate. Situated on almost an acre lot, the breathtaking waterfront views will impress. This home features a grand entrance foyer, an open and spacious living room with a beautiful fireplace, a formal dining room, soaring 13 ceilings, an impressive gourmet professional kitchen, elevator and extensive attention to detail throughout. The Garage boasts parking for 10 cars with 2 car lifts and an elevator to all levels. The Large Master Bedroom is located on the main level. Matching guest suites are located on the second level with their own sitting room and mini bar. Luxury pool and patio with built-in fountain create unparalleled entertainment possibilities.
  Details
Key Haven
$3,600,000 4,184 (SqFt)
  • 5
  • 3
  • Single Family

88 Driftwood Drive
KEY WEST, FL 33040

Key Haven 10th Add   Waterfront: Yes MM: 5
Side of Island: Bay/Gulf
Dockage: None

Ensconce yourself in the classic, elegant luxury of this remarkable Gulf front home. Nestled on a private road at the end of Key Haven, this stunning open water home built w/impeccable craftsmanship & peerless attention to detail features high ceilings, oversized crown moldings & baseboards, custom painted recessed metal tile ceilings, 8ft doors, elevator, RV garage, electronical controlled lighting, top of the line Viking & Sub Zero appliances & much more. 5BR/3.5BA, office, study, dressing room, custom wet bar & even a chandelier that can be lowered w/the push of a button! Lounge on your porch where the sunrise views will take your breath away! Planted w/native landscaping for ease, impact glass for simplicity & generator for convenience.
  Details
Key West
$3,575,000 4,500 (SqFt)
  • 5
  • 3
  • Single Family

1214 Olivia Street
KEY WEST, FL 33040

W C Maloney Diagram   Waterfront: No MM: 1
Side of Island: Median
Dockage: None

This magnificent 4,500 sqft family estate with 5-bedrooms and 3.5 baths, offers the finest in livable elegance. The open floor plan flows easily outdoors to comfortable porches and lushly landscaped gardens and grotto pool. The chefs kitchen boasts handcrafted cabinetry, double appliances, and 1,000 bottle wine cellar. The master suite is complete with morning kitchen, large bathroom, and generous walk-in closet. The detached cottage features kitchenette, bedroom and bath. Located in The Meadows, one of Key Wests premier neighborhoods, the home occupies an 11,209 sqft double lot ensuring quiet privacy and the best of tropical living. Off-street gated parking and X flood zone complete the perfect home.
  Details
Shark Key
$3,450,000 5,375 (SqFt)
  • 4
  • 3
  • Single Family

34 Cannon Royal Drive
KEY WEST, FL 33040

Shark Key   Waterfront: Yes MM: 11
Side of Island: Bay/Gulf
Dockage: Other Dockage

Magnificent Custom Built Shark Key Estate on one of the largest lots on Shark Key located on a beautiful point with water on two sides & water deep enough for boat access. Four bedrooms three and one half bath designed by Dennis Bebe with a panoramic views of the sunsets. Superior master craftsmanship, elevator off the garage to all floors, the large master suite & bath, private office & storage is dedicated to the second story with over 1500 Sq. Ft., walk in closets, wet bar and private porch. Located on the first floor is Spectacular one-of-a-kind kitchen, dining, three bedroom guest wing each with private baths and porches. Beautiful Orchid House and room for a pool. Shark Key is a mandatory homeowners association.
  Details
Key West
$2,900,000 2,177 (SqFt)
  • 4
  • 3
  • Single Family

810 Eisenhower Drive
KEY WEST, FL 33040

Benj Alburys Subdivision Dia   Waterfront: No MM: 2
Side of Island: Median
Dockage: None

A RARE JEWEL. Built in 1929 this four bedroom four and one half bath home has been meticulously renovated and restored by the current owners. Natural Dade County Pine interiors in beautiful condition, a gourmet kitchen that fits right into the architecture, separate living and dining rooms, an office plus a climate controlled wine room. Theres a separate and beautiful guest cottage with outdoor shower. The large loggia has views of the house, heated pool with water feature and the stunning stands of extraordinary palms and landscaped gardens that complete this amazing setting. Covered carport with storage and electric gates. All in impeccable condition and structurally re-engineered to withstand the elements for another 100 years.
  Details
Key West
$2,850,000 1,984 (SqFt)
  • 3
  • 3
  • Single Family

51 Sunset Key Drive
KEY WEST, FL 33040

Sunset Key   Waterfront: No MM: 0
Side of Island: Bay/Gulf
Dockage: Dock Privileges,Firs

Beautifully finished three bedroom Residence on Sunset Key Island. 3 Bed homes are rarely available on Sunset Key. No expense was spared with elegant marble floors, granite countertops, exotic hardwood floors upstairs, balconies off every room, and incredible views of the famous Key West sunset over the open ocean. Talk about a touch of real paradise! Access to the island by 24/7 ferry service makes this a truly unique destination.
  Details
Key West
$2,800,000 1,984 (SqFt)
  • 3
  • 3
  • Single Family

53 Sunset Key Drive
KEY WEST, FL 33040

Sunset Key   Waterfront: No MM: 0
Side of Island: Bay/Gulf
Dockage: Dock Privileges,Firs

Have You Ever Dreamed Of Living On Your Own Private Island? Spectacular 3 bedroom, 3 bath residence on Sunset Key Island located in the center of Key West Harbor. Access by 24/7 ferry service makes living on Sunset Key the most unique living experience in the Florida Keys. Enjoy the Gourmet restaurant, Spa, Fitness Center, three Beaches within walking distance, Deep Water Boat docks for homeowners, Tennis Courts, Boating and Water access to both the Atlantic and Gulf of Mexico, and much more. This is like having your own Four Star Resort, with a convenient International Airport only minutes away. Give us a call now for more information.
  Details
Key West
$2,750,000 2,457 (SqFt)
  • 3
  • 3
  • Single Family

1021 Washington Street
KEY WEST, FL 33040

Webb Realty Co Subdivision   Waterfront: No MM: 1
Side of Island: Median
Dockage: None

Located in the coveted Casa Marina District, this property encompasses over 27,000 square feet. The spacious, one level main home features two bedrooms and two baths. The one bedroom and one bath guest cottage sits adjacent to the three car garage. There are six wells on the property which currently irrigate the property. In addition, there are two vacant buildable lots; one with approximately 6,300 sf and the other 7,200 sf. There are so many possibilities for this property.
  Details
Key West
$2,750,000 3,043 (SqFt)
  • 5
  • 4
  • Single Family

1414 Newton Street
KEY WEST, FL 33040

Benj Alburys Subdivision Dia   Waterfront: No MM: 0
Side of Island: Median
Dockage: None

Exquisite, low maintenance, custom built home in the tranquil Meadows neighborhood. Special features of this 3000 ft contemporary Caribbean home include an generator that can run the home for 2+ weeks, a 30 pool with a full length waterfall, a carport and garage, a surround sound theater system, over 100 orchids among its lush gardens. A separate entrance leads to a large office/guest bedroom with a bath en suite. The kitchen has Su-Zero/Wolf appliances, large fridge, wine cooler,2 dishwashers, 2 freezer drawers, grill and pot filler. Category 5 rated construction. Owner is a Florida licensed Real estate broker.
  Details
Key West
$2,595,000 1,984 (SqFt)
  • 3
  • 3
  • Single Family

45 Sunset Key Drive
KEY WEST, FL 33040

Sunset Key   Waterfront: No MM: 0
Side of Island: Bay/Gulf
Dockage: None

Fulfill your fantasy of living on a small tropical island. Only a 5 minute ferry ride from Key West, Sunset Key is a luxury retreat with resort like amenities including two tennis courts, beautiful homeowners beach and access to spa, gym, restaurant and concierge services. This beautiful three bedroom, three bath home has an open floor plan with sunny rooms, high ceilings, crown molding, tile and wood floors and designer details throughout. It is in perfect condition. The home is sited on a private lot with a wrap-a-round porch, private master suite deck, beautifully landscaped yards and heated pool. A third floor porch provides great views of the island and water beyond. There is 24 hour Ferry service from the Westin Resort to Sunset Key.
  Details
Key West
$2,500,000 4,358 (SqFt)
  • 9
  • 8

1001 Eaton Street
KEY WEST, FL 33040

Old Town Unrecord   Waterfront: No MM: 1
Side of Island: Median
Dockage: None

Great Old Town Investment Property!The Cuban Consulate (1001 Eaton Street) was reportedly built in 1890 and In 1930 a second home was constructed on the property (323 Grinnell Street) A beautiful garden separates the two homes and includes a pool. The architecturally significant Eaton Street house is a two-story temple style Classic Revival structure with gingerbread trim and a large tower/veranda treatment. The property and facilities are well maintained and can be continued as a rental property or the Eaton Street main home can easily be converted back to a single-family residence. A driveway adjoins the Eaton Street home with space for two automobiles.
  Details
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 05-30-2015.

Shoreline Properties
92300 Overseas Hwy Suite 303
Tavernier, Florida 33070

1(800) 692-3605
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