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

Total Listings 219
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
$8,400,000 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
$7,400,000 5,717 (SqFt)
  • 7
  • 7
  • Single Family

1017 Southard Street
KEY WEST, FL 33040

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

This is perhaps the finest luxury estate in Key West. It encompasses over 20,000 square feet of land and over 5,000 square feet of living space in the heart of the historic district. The spectacular Queen Anne mansion, circa 1890, is complimented by three additional buildings: a pool house with one bedroom and an indoor/outdoor bath, a garage with an upstairs apartment, and a two bedroom/two bath guest home. The historic residence features a master suite on each floor, a stunning octagonal living room, soaring ceilings, and custom painted Dade County pine walls and floors. In the center of the estate, the hand tiled pool sparkles among mature tropical landscaping with spectacular banyan and royal poinciana trees.
  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 4,788 (SqFt)
  • 6
  • 7
  • Single Family

58 Front Street
KEY WEST, FL 33040

Porter Court   Waterfront: No MM: 0
Side of Island: Ocean
Dockage: None

Conch Casa Grande is the largest home in Truman Annex. With 11 foot ceilings, mahogany floors and detailed woodwork, this grand home captures the essence of another era, but since it was built relatively recently, it has the modern conveniences we expect from a modern home. The living room is simply spectacular; with space and light everywhere you look. Off the front hall downstairs is the first of six bedrooms. There are four more bedrooms on the second floor, and a sixth bedroom on the 3rd floor. All six bedrooms have en suite bathrooms. This home has a Truman Annex special transient license, generating $300,000 in gross income in 2014. 2015 income is currently running 20% ahead of that.
  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
$4,700,000 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

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 in-ground 10x30pool w/ Jacuzzi, sundeck, BBQ, heated in-ground 8x6 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.
  Details
Key West
$3,995,000 4,012 (SqFt)
  • 4
  • 5
  • Single Family

1019 Flagler Avenue
KEY WEST, FL 33040

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

Located in the exclusive Casa Marina, discover a home that has been transformed, preserving its historic fabric graciously blended with the very latest architectural design. Greeting you are awe inspiring 12 foot coffered ceilings with oversized moldings. French doors from every room reveal the lushly landscaped pool and loggia area for year round enjoyment. On the first level is a top of the line chefs kitchen off the dining /living area, a large family room, a powder room and an en suite bedroom. Upstairs are 3 sumptuous bedroom suites and a large deck overlooking the beautiful pool and gardens. A pool house with full bath adds the perfect touch. Hurricane windows and doors. Circular driveway with covered off street parking.
  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

Picture yourself in this authentic Historic Key West estate. Built in 1903, this 5 bedroom Victorian mansion with guest cottage has been well-maintained. The current owners renovation in 2002 preserved original features such as doors, lighting, crown molding and flooring while adding hand-crafted cabinetry, tin ceiling tiles, and slate flooring that blend with the original features. The award winning renovation also included structural restoration which ensures the homes integrity for years to come. The mansion sits on a double lot with lush vegetation surrounding a grotto pool, flagstone patio, and gazebo with outdoor kitchen providing perfect privacy. Gated parking and X flood zone location complete this historical masterpiece.
  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
$2,760,000 2,205 (SqFt)
  • 3
  • 3
  • Single Family

1421 White Street
KEY WEST, FL 33040

Tropical Bldt & Investment Co   Waterfront: No MM: 2
Side of Island: Median
Dockage: None

Truly, a raised Eyebrow. Totally renovated & utterly charming, this classic Key West home has it all. Gourmet kitchen with granite counters & stainless appliances, closets, walk in pantry, screened patio overlooking the pool deck, a pocket yoga studio & even a widows walk. 3BR/3.5Ba + Office, also one of the two outbuildings has been permitted in the past to convert to an additional 1BR/1BA cottage. Surrounded by a white picket fence, the lovely yard has decks, mature tropical landscaping & a brand new pool with a waterfall. Off street parking for multiple cars on both White St as well as on Von Phister.
  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
$2,500,000 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 07-28-2015.

Shoreline Properties
92300 Overseas Hwy Suite 303
Tavernier, Florida 33070

1(800) 692-3605
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