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

Total Listings 221
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26  Sunset Key Drive  For Sale, MLS 583913
$6,300,000
Sunset Key
Sunset Key   - MM: 0.00
4 Bed, 4 Baths, 3,262 SqFt Days Listed: 440
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Firs

Dont miss this opportunity to own a well-appointed, two-story, four-bedroom private residence located on the world-famous private island of Sunset Key. Lounge beside the pool and take in one of the most beautiful waterfront views of Key West. Or, spend time relaxing on one of Sunset Keys three beaches. For some excitement, Historic Downtown Key West and all that it offers is just a three-minute ferry ride away. This home provides an amazing slice of island life.

14  Sunset Key Drive  For Sale, MLS 589017
$6,200,000
Key West
Sunset Key   - MM: 0.00
3 Bed, 3 Baths, 3,302 SqFt Days Listed: 93
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Firs

328  Whitehead Street  For Sale, MLS 590200
$5,899,000
Key West
Old Town Unlisted   - MM: 1.00
5 Bed, 5 Baths, 2,934 SqFt Days Listed: 30
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This exclusive home is one of the Crown Jewels of Truman Annex, One of only 3 properties in Truman Annex with a Whitehead St. address & rear access from Admirals Lane. Formerly the Coast Guard Commanders Quarters. Includes a Transient License! One of the largest lots in the Annex at 14,410 sf. There are two buildings; The main house is two story 3 bedrooms, 2 bathrooms & one half bath down. Wood floors & high ceilings up and down, large open kitchen with Wolf and SubZero Appliances. Every room up & down, front & back open to unbelievably large covered porches total 2,250 sf. In addition, a two story 2bd/1.5 bath guesthouse connected by catwalk. Guesthouse has large outdoor pool bar, Miele appliances. Large private heated pool, outdoor shower and private spa. Covered parking for 3-4 car

13  Sunset Key Drive  For Sale, MLS 587108
$5,800,000
Sunset Key
Sunset Key   - MM: 0.00
4 Bed, 4 Baths, 2,480 SqFt Days Listed: 227
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Firs

Centered on idyllic Crescent Beach on world famous Sunset Key Island, the location of this four-bedroom, three-and-a-half bathroom home is the best of the best. The tastefully done interior features crown moldings throughout. Abundant windows and French doors with transoms bring in ample natural light and provide beach and water views. An additional office completes the homes spacious living areas. From the backyard, get a front row seat for the jaw-dropping Key West sunsets and relax around the beachfront pool. Come see this incredible home priced at an equally incredible value.

724  Eaton Street  For Sale, MLS 590422
$4,985,000
Key West
Old Town Unrecord   - MM: 1.00
7 Bed, 7 Baths, 5,881 SqFt Days Listed: 12
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Located on the Southernmost tropical island in the US with average winter highs of 75 and average summer highs of 88, the Curry-Freeman House, circa 1865, is one of the oldest private residences in the Florida Keys. Custom-built by a prosperous seafaring merchant and ship-builder, the mansion was constructed by Old World craftsmen using only the finest materials available at a time when Key West flourished as one of the richest cities in the country. Since inception, the home has been a center of political and social prominence. Many family members have been and remain recognized pillars of the community, serving as elected public officials and hosts of countless political, civic and cultural affairs. the stately structure has withstood the test of time.

326  Caroline Street  For Sale, MLS 586608
$4,795,000
Key West
Old Town Unrecord   - MM: 0.00
5 Bed, 5 Baths, 4,279 SqFt Days Listed: 262
-3.13% ($155,000) 1 Price Change : Last Change 44 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Amazing opportunity-available for the first time in over a decade. This magnificent estate enjoys over 13,000 square feet of tropical landscaping, including a three bedroom, three bathroom main house and full 2 story guesthouse with a connecting covered deck. The large garage provides enough space for two vehicles and plenty of storage. There is additional room inside the automatic gated parking area for 2 more vehicles. The main home was originally located across the street and was moved to its current corner location back in 1990. Enjoy hardwood floors, crown moldings, a fully updated kitchen, luxurious bedrooms,baths and more.

22  Hilton Haven Road  For Sale, MLS 580606
$4,400,000
Key West
Hilton Haven Sec 2 A   - MM: 2.00
5 Bed, 5 Baths, 5,898 SqFt Days Listed: 665
-19.93% ($1,095,000) 2 Price Changes : Last Change 240 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift105ft.Concr

Wondrous waterfront estate only a few minutes from downtown Key West. Capturing the relaxed grandeur of a bygone era, this sprawling home features water views from almost every room in the house. Facing South with views from East to West, the main house was restored in 1995 with walls rebuilt in concrete to include Pella windows & Anderson glass pocket doors to complete the indoor/outdoor living dream. When entering the home through the huge hand made art pieces that comprise the front door you immediately see through to the fantastic central courtyard with pool and entertainment areas along with the open water beyond....

58  Front Street  For Sale, MLS 589735
$4,399,000
Key West
Old Town Unlisted   - MM: 1.00
6 Bed, 6 Baths, 3,920 SqFt Days Listed: 57
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

313  William Street  For Sale, MLS 589738
$3,850,000
Key West
Old Town Unrecord   - MM: 1.00
4 Bed, 4 Baths, 2,993 SqFt Days Listed: 57
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Beautiful, magnificent, just a couple of words used to describe the award winning George A. T. Roberts house, a circa 1900 historic home. Totaling 4BD/4.5BA, including the pool house & guest cottage, its been restored with an easy elegance. A classic Queen Anne beauty, it is one of the special ones & sits on a huge 9,573sf double lot in the heart of the Old Town Historic Seaport District. Upon entering the grand foyer you will find the staircase, open living room, Bay windows, dining room & den/library all with high ceilings and Dade County pine throughout. Enjoy a spacious and updated gourmet kitchen, perfectly placed and opening onto a glorious outdoor covered porch that spans 34 X 16 (across the entire width of the home) with ample seating areas and views

66  Front Street  For Sale, MLS 590493
$3,700,000
Key West
Old Town Unlisted   - MM: 1.00
5 Bed, 5 Baths, 2,932 SqFt Days Listed: 4
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Lushly landscaped oasis with 3 story, detached single family home w/ classic Key West architectural design in the Truman Annex, including the special Truman Annex transient license. Enjoy your own heated pool w/ waterfall. The first level is an open design including kitchen, dining, living area, powder room; and, just off the dining, a den thats easily converted to additional sleeping quarters. The 2nd level has laundry and 2 main suites sharing a spacious deck overlooking the pool. The 3rd floor has 2, dormered bedrooms w/ shared bath. Up just one more set of stairs is a widow walk w/ glorious vistas of Old Town & sunset over the Gulf. Wood floors throughout, impact glass windows & doors, and pool house w/ powder room & outdoor shower abutting a two-car garage with electric gate.

1214  Olivia Street  For Sale, MLS 590058
$3,700,000
Key West
W C Maloney Diagram   - MM: 2.00
5 Bed, 5 Baths, 4,152 SqFt Days Listed: 39
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Steeped in history and class, this grand mansion is elegant and simply breathtaking! This 4,152 square foot home boasting 5 bedrooms sits on a 11,209 square foot landscape that ensures privacy on all sides! Filled with some of the most beautiful light seen in any Key West home, this home feels so good. From the beautiful all white kitchen, soft living area, large dining room and reading area, one never feels at a loss for someplace to go. The wine connoisseur will marvel at the 1000 bottle climate controlled wine cellar, perfect for a home that begs to have large dinner parties! The extra wide IPE back porch captures the breezes and has so much seating area. There is a large pool and Jacuzzi that is surrounded by old Key West curbstones. Add on a gazebo for outdoor grilling and fun

708  Eaton Street  For Sale, MLS 589737
$3,700,000
Key West
Old Town Unlisted   - MM: 1.00
5 Bed, 5 Baths, 3,306 SqFt Days Listed: 57
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This is a one of a kind house, currently owned by legendary Dale Earnhardt Jr. The property is in the heart of Old Town and is steeped in a rich and mysterious history, complete with a secret hidden hatch door to observe people in the parlor. This 5 Bedroom 3.5 bath home was built in 1863 during the Civil War era, and it retains most of its original architecture that was lovingly maintained. It has one of the deepest and largest pools in Key West, reportedly being about 13 to 14 feet deep. A gate from the second-floor porch opens allowing daring (or crazy) individuals to jump off the second floor into the pool. The Kitchen was artfully designed by Earnhardt to resemble the inside of a pirate ship including a large ships wheel at the end of the bar,

708  White Street  For Sale, MLS 588804
$3,595,000
Key West
Old Town Unrecord   - MM: 1.00
5 Bed, 5 Baths, 4,548 SqFt Days Listed: 110
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Magnificent, recently built home (2005) in the heart of Old Town with all the luxury features you have been dreaming of. With over 4,000 sq. ft on a 6,654 sq. ft. lot this 5 bedroom (or 4 bedroom and den), 5 bath masterpiece has a soaring 24 foot ceiling in the great room, Brazilian Cherry floors, Tray ceilings, two living rooms, Anderson impact windows, plantation shutters throughout, and a laundry room on each floor. All of the bedrooms have baths en-suite and balconies, with a master bedroom on each floor. Outdoors is your private sanctuary with IPE tropical decking, landscape lighting, sprinkler system, large, newly resurfaced pool and spa, and covered parking. This is a very rare combination of location, square footage, and newer construction. Offered partially furnished.

727  Washington Street  For Sale, MLS 588692
$3,500,000
Key West
Key West Investment Co Subdiv   - MM: 1.00
4 Bed, 4 Baths, 3,855 SqFt Days Listed: 116
-16.67% ($700,000) 2 Price Changes : Last Change 29 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

SPECTACULAR PRICE REDUCTION. Luxury Homes arent everything to everyone, but everything to a select few! The uniqueness of this estate comes from the design that surrounds the courtyard, utilizing its 11,000 SF lot for the exclusive pleasure of its owners. Built in 1999, this luxury home has it all plus 2 pools, a spa, lush tropical foliage, 2 car garage, an efficiency apartment and 4 + car off-street parking. This one of a kind estate, is located in the prestigious Casa Marina neighborhood. Prepare to be amazed!

901  Casa Marina Court  For Sale, MLS 586986
$3,499,000
Key West
Martello Towers   - MM: 1.00
5 Bed, 5 Baths, 3,524 SqFt Days Listed: 238
-4.14% ($151,000) 1 Price Change : Last Change 82 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Sophisticated & stunning Casa Marina home situated on an impeccably manicured corner parcel. Hidden from the street by a high wall, this graceful 5 BD/5.5 Ba home caters to the ultimate in comfort. Glass doors are off virtually every room to covered patios overlooking pristine gardens with meandering paths leading to a huge resort size heated & chilled pool. Beautifully appointed with a fabulous open kitchen with pass through to a spacious outdoor dining/ living room & wet bar. Incredible living space with family room, living room, dining room, covered porches both front and back & an elegant master suite.. Enjoy the convenience of a garage as well as a 2nd floor bedroom w/ rare water views of the Atlantic. This most elegant & private retreat sits on a huge15,541 SF lot, lushly

62  Front Street  For Sale, MLS 587478
$3,350,000
Key West
Old Town Unlisted   - MM: 1.00
4 Bed, 4 Baths, 2,486 SqFt Days Listed: 196
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Incredible opportunity to own both a delightful single family home in the coveted Truman Annex gated community AND a Four Bedroom Transiently Licensed Turn Key Luxury Vacation Rental Investment Home, fully outfitted to the highest standard and projected to achieve rental income in excess of $200,000 in the first calendar year of active rental. Collect the revenue of an exceptional vacation home with a special transient license, with the benefit of visiting and enjoying your beautifully classic yet unique Eyebrow home in the heart of Old Town - complete with sunny private pool, covered deck, and magnificently landscaped grounds featuring waterfalls of orchids spilling from a gorgeous Gumbo Limbo tree. Previously a full time residence...

4  Go Lane  For Sale, MLS 590508
$3,320,000
Key West
Vista Delmar Amd Plt   - MM: 4.00
5 Bed, 5 Baths, 3,100 SqFt Days Listed: 3
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

Key west living at its finest. Spectacular waterfront property where the Gulf of Mexico meets the Atlantic Ocean. Jump on your boat, go under the bridge and make a right turn to the Atlantic ocean or a left turn into the Gulf of Mexico. Spacious 10,000 sq.ft. lot with beautiful gardens. This 5bd 5ba home is the perfect escape from the real world. Schedule your personal tour today.

603  Southard Street  For Sale, MLS 589782
$3,295,000
Key West
Old Town Unrecord   - MM: 1.00
6 Bed, 6 Baths, 2,870 SqFt Days Listed: 56
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Location location location! Property situated on a corner lot with mixed-use commercial zoning, room for eight bedrooms and seven baths. Current licenses (including six transients) and flexible floor plan allow for many uses including guesthouse, boutique hotel, deluxe office space, single-family home or possibly a restaurant.. Built during the Lincoln Era, architectural details include wrap around porches, hardwood floors, and Old World craftsmanship. There is a heated swimming pool, off-street parking, and just a block walk to world famous Duval Street. Please make an appointment today to visit this amazing property and explore for yourself the many possibilities. No limits!

1102-1106  Petronia Street  For Sale, MLS 589257
$3,100,000
Key West
Old Town Unlisted   - MM: 1.00
4 Bed, 4 Baths, 4,626 SqFt Days Listed: 82
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

623  Southard Street  For Sale, MLS 582338
$2,999,999
Key West
Old Town Unrecord   - MM: 1.00
4 Bed, 4 Baths, 2,252 SqFt Days Listed: 540
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Illustrious block in the heart of Old Town, this transiently licensed 4 bedroom 4 bath eye brow conch house is very special. Tropical and lush this private 5,600 sf lot is the perfect peaceful place to relax by your pool and catch some rays. Licensed as a 3 unit guest house & in beautiful shape, it can be rented to 3 separate groups or is perfect for the large extended family. Wonderfully furnished and sold turnkey it is full of style & charm. Downstairs offers 2BD/2 BA & a large great room w/ French doors to a covered porch. Upstairs there are two 1Bd/1BA units each with its own kitchen so your friends & family can have their own space too. Just 2 blocks from Duval, its close to all of the fine restaurants and entertainment. Its Fully fenced with off street parking, it has it all!

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 04-08-2020.

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Key Largo, Florida 33070

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