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

Total Listings 166
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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: 267
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.

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: 54
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 586997
$5,000,000
Key West
Old Town Unrecord   - MM: 1.00
7 Bed, 7 Baths, 5,881 SqFt Days Listed: 64
-14.38% ($840,000) 1 Price Change : Last Change 6 Days Ago
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.

744  Windsor Lane  For Sale, MLS 584145
$5,000,000
Key West
Old Town Unlisted   - MM: 1.00
6 Bed, 6 Baths, 5,632 SqFt Days Listed: 255
-13.04% ($750,000) 3 Price Changes : Last Change 39 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

A hidden tropical paradise awaits behind the hand-carved Indonesian teak doors of 744 Windsor Lane. What looks like two joined together Key West cottages lies a private courtyard with ponds, waterfalls, and exquisite plants leading into the grand entry. Walls of windows in this modernist home overlook a quarter-acre of manicured gardens, lanai, outdoor kitchen, cabana bath, and one of the largest pools in Old Town. The gathering room of this 5632 Sq Ft home leads to formal and informal living areas, spacious kitchen, 6 bedrooms, and 7 bathrooms. Ideal for entertaining, this home can graciously host family holiday gatherings, elegant cocktail parties, or fundraising gala with scores of guests. A truly unique property in the heart of Old Town, fully updated and offered in superb condition.

326  Caroline Street  For Sale, MLS 586608
$4,950,000
Key West
Old Town Unrecord   - MM: 0.00
5 Bed, 5 Baths, 4,279 SqFt Days Listed: 89
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.

2  Go Lane  For Sale, MLS 582444
$4,469,500
Key West
Vista Delmar Amd Plt   - MM: 4.00
4 Bed, 4 Baths, 3,777 SqFt Days Listed: 359
-4.39% ($205,400) 2 Price Changes : Last Change 213 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 10ft.

0 Go Lane is actual address. Beautiful new home on double lot, 200 ft of seawall on 2 sides of the property, located at end of a cul-de-sac. . Views of the Ocean and Gulf from the 3rd floor. Largest private residence pool in KW, 45 X 55 with waterfall, tiki hut. Main floor Master bedroom. Bamboo hardwood & tile throughout. Very unique hardwood pattern on upper floor. Elevator all levels. Stainless appliances in kitchen including a gourmet Le Corneau stove. Breathtaking chandeliers in 2 story foyer, dining room & master bedroom. 3 bedrooms on upper level w/ 2 full bathrooms upstairs. Every bedroom with a balcony. Pervious pavers in driveway/around pool and deck area. Sprinkler system. Fenced with electronic gate for privacy and security. Must see to appreciate!

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: 492
-19.93% ($1,095,000) 2 Price Changes : Last Change 67 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 583770
$4,399,000
Key West
Old Town Unlisted   - MM: 1.00
6 Bed, 6 Baths, 4,636 SqFt Days Listed: 275
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Conch Casa Grande is the largest home in Truman Annex, with 4636 sq ft of living space. With 11 foot ceilings and detailed woodwork, this grand home captures the essence of another era, a diamond in the rough ready for your own personal touch to make it the home of your dreams. The living space is simply spectacular; with space and light everywhere you look. The powder room also has a tub and shower. Just 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, which has generated as much as $216,000 a year in gross annual income. Bookings and reservations for 2019 have reached $181,000.

3810  Flagler Avenue  For Sale, MLS 587743
$4,270,000
Key West
Vista Del Mar   - MM: 4.00
4 Bed, 4 Baths, 4,495 SqFt Days Listed: 5
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Sleek modern lines define a sophisticated elegance throughout this 4,315 sq. ft home. The high ceilings in the foyer open to the impressive kitchen, dining and living area, revealing a breathtaking view of the wide canal and dock with a boat lift. Just some of the exquisite details of this house are the 9 ft folding Euro doors, gourmet kitchen with a separate butlers pantry, large wine fridge and high-end appliances. On the lower level there are 3 generous sized bedrooms, 2.5 bathrooms, an oversized office, and a large media room. Ascend the elegant glass and ebony floating staircase to the master retreat with its private veranda, en suite bathroom, walk-in closet and morning kitchen complete the master suite.

524  Frances Street  For Sale, MLS 577905
$3,750,000
Key West
Old Town Unrecord   - MM: 1.00
4 Bed, 4 Baths, 2,820 SqFt Days Listed: 671
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

The House of Seven Gables is an exquisite ceramic star winning historic renovation located on one of the finest streets in Old Town Key West. This impeccably constructed Victorian style home was built in 1907 by carpenter-architect William Kennedy, the designer of the Curry Mansion. Renovated to perfection, this home now combines every modern luxury with superb attention to historic detail in every aspect from moldings to wainscoting. Unique features include custom mahogany kitchen cabinets, Brazilian hardwood floors, tumbled stone and travertine bathrooms, impact glass doors, and two large master suites, one downstairs and one upstairs with treetop views from the balcony. The backyard has a stunning gazebo with built in kitchen for outdoor entertaining, a spacious deck and heated pool...

901  Casa Marina Court  For Sale, MLS 586986
$3,650,000
Key West
Martello Towers   - MM: 1.00
5 Bed, 5 Baths, 3,524 SqFt Days Listed: 65
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: 23
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...

1500  White Street  For Sale, MLS 581789
$3,200,000
Key West
Martello Towers   - MM: 1.00
4 Bed, 4 Baths, 2,930 SqFt Days Listed: 409
-9.83% ($349,000) 2 Price Changes : Last Change 79 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

There is an extraordinary opportunity to own a very stylish and well-built home on an estate sized lot in the very desirable Casa Marina neighborhood. This incredible property includes a beautifully renovated four-bedroom, four bath plus two half bath home on more than a third of an acre exquisitely landscaped corner parcel. The spectacular great room has a large living area with wood floors, a soaring vaulted ceiling with skylights, a fireplace and a gourmet kitchen with stainless steel appliances. Adjoining the great room is a large 800+ square foot screened porch perfect for year-round outdoor living. The main house has three bedrooms, three and a half baths on one level including the spacious master suite with large walk-in closet. Above the garage is a separate very private guest

40  Sunset Key Drive  For Sale, MLS 579352
$3,199,000
Sunset Key
Sunset Key   - MM: 0.00
3 Bed, 3 Baths, 1,920 SqFt Days Listed: 578
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Firs

Pre-consruction private residence on Sunset Key Island. Sunset Key Island is the epitome of island living, with no cars; three sandy beaches within a short walk from the house; tennis courts; lush tropical landscaping; and a gourmet restaurant, room service to your house, etc. Come see this island paradise for yourself.All images shown are renderings.Buyer can purchase vacant lot with approvals and building plans prior to construction beginning for $1,600,000.

1102-1106  Petronia Street  For Sale, MLS 583805
$3,100,000
Key West
Old Town Unlisted   - MM: 1.00
4 Bed, 4 Baths, 4,626 SqFt Days Listed: 274
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Beautiful Historic Property, with room to expand. Rare find with extra vacant lot attached for building another home, pool or garage with mother-in-law. 3 separate lots. Main house built in 1893. Second house on separate lot built in 1905. To many fruit trees to name! You name it they got it! So many possibilities with this gorgeous property! One of a kind.

421  William Street  For Sale, MLS 587457
$3,000,000
Key West
Old Town Unrecord   - MM: 1.00
4 Bed, 4 Baths, 3,392 SqFt Days Listed: 25
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Dade County pine walls, Brazilian cherry floors, high ceilings, hand crafted moldings, and wraparound porches ensure this 3,392 sq. ft. home is both elegant and modern without losing the character of its historic past. The main hall leads past a grand staircase, formal living room, dining room, and half bath ending in a modern chefs kitchen open to the expansive family room. Multiple French doors open to the private entertainment deck with large pool and outdoor shower surrounded by tropical foliage. Two large ensuite guestrooms and a master suite with beamed cathedral ceiling, a deck overlooking the pool and spacious bath with claw foot tub and shower complete the second floor. A private entrance guest suite on the third floor includes a living room, bath, kitchenette and bedroom.

1423,1418  Petronia., Newton Street  For Sale, MLS 584137
$3,000,000
Key West
Benj Alburys Subdivisiond   - MM: 2.00
6 Bed, 6 Baths, 3,285 SqFt Days Listed: 256
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

A rare investment opportunity in the prestigious neighborhood known as The Meadows. This offering includes two homes, a swimming pool, a spa, expansive gardens, and off-street parking. Create a compound in paradise!

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: 367
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!

306  Elizabeth Street  For Sale, MLS 582811
$2,950,000
Key West
Old Town Unrecord   - MM: 1.00
6 Bed, 6 Baths, 3,445 SqFt Days Listed: 338
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Classic Victorian architecture and historic lore combine to make this one of the most legendary homes in Key West, now on the market for the first time. Built by Odet Philippe in the 1800s and known historically as The Pirate House, this majestic beauty is steeped in Key West seafaring history. Zoned as 3 non-transient legal units, theres plenty of room for family and friends with 6 bedrooms and 6 bathrooms. The backyard is a tropical paradise of lush landscaping surrounding a luxurious pool and outdoor dining space. Double galleried front porches & back sundecks off the 2nd and 3rd stories add to the abundant outdoor space. Off-street parking and just a short walk from the Historic Seaport and Duval St.

1501  Grinnell Street  For Sale, MLS 582979
$2,950,000
Key West
Martello Towers   - MM: 1.00
4 Bed, 4 Baths, 2,902 SqFt Days Listed: 325
-14.49% ($500,000) 2 Price Changes : Last Change 227 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Enter the enchanted world of a Key West legend & home of David Wolkowsky, considered to be one of the most important transformational influences in modern-day Key West. Enjoy a magnificent light filled great room supported by touches of Bali and Thailand in the form of floor to ceiling pillars from the other side of the world. The soaring ceiling is remarkable & the walls are all glass and open to appreciate both the views and the climate, punctuated by an enormous pool & patio to entertain. The main house is 2 bedrooms / 2 baths & the guest house has an additional 2 bedrooms / 3 baths. On a substantial 11,730 SF corner lot, its totally walled & fenced for privacy. This special home is a just one block from the historic Casa Marina resort and the beaches.

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 10-18-2019.

Shoreline Properties
92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
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