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Showing 1-20 of 23 Homes For Sale
For Sale
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$4,995,000

3 Beds | 4.0 Baths | 3,104 Sqft

1014 Flagler Ave, Key West, FL, 33040

Some homes are built; others are authored. This is one of the latter-an architectural landmark shaped by David Wolkowsky, whose vision helped define Key West itself, with architecture by award-winning...

Ad#: 7253783 • Added: 02/10/2026 • Updated: 05/21/2026
Ad#: 7253783 • Added: 02/10/2026 • Updated: 05/21/2026
For Sale
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$1,949,000

2 Beds | 3.0 Baths | 1,357 Sqft

3841 N Roosevelt Blvd 315, Key West, FL, 33040

Experience ultimate elegance at Key West's Beachside Resort & Residences! This first-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two...

Ad#: 6704284 • Added: 10/08/2025 • Updated: 10/09/2025
Ad#: 6704284 • Added: 10/08/2025 • Updated: 10/09/2025
For Sale
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$1,949,000

2 Beds | 3.0 Baths | 1,357 Sqft

3841 N Roosevelt Blvd 332, Key West, FL, 33040

Experience ultimate elegance at Key West's Beachside Resort & Residences! This third-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two...

Ad#: 6704283 • Added: 10/08/2025 • Updated: 10/09/2025
Ad#: 6704283 • Added: 10/08/2025 • Updated: 10/09/2025
For Sale
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$1,849,000

2 Beds | 2.0 Baths | 1,469 Sqft

1800 Atlantic Blvd 315B, Key West, FL, 33040

TRANSIENT investment opportunity awaits. Spacious 2bd/2ba situated in the centrally located waterfront community of 1800 Atlantic. Large covered balcony overlooks a lush tropical courtyard with huge...

Ad#: 7825823 • Added: 06/04/2026 • Updated: 06/04/2026
Ad#: 7825823 • Added: 06/04/2026 • Updated: 06/04/2026
For Sale
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$1,700,000

2 Beds | 2.0 Baths | 1,311 Sqft

1800 Atlantic Blvd 327C, Key West, FL, 33040

Licensed for nightly Rentals! On average 120k/yr. Introducing an exquisite offering at one of Key West's sought-after waterfront resorts, 1800 Atlantic Blvd. A completely remodeled, stylish 2-bedroom...

Ad#: 6750125 • Added: 10/22/2025 • Updated: 05/23/2026
Ad#: 6750125 • Added: 10/22/2025 • Updated: 05/23/2026
For Sale
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$1,680,000

3 Beds | 4.0 Baths | 1,442 Sqft

1001 United St B, Key West, FL, 33040

Enjoy your tropical retreat in the heart of Old Town Key West with this stunning, fully remodeled, three-story corner lot island oasis. The first floor of this expansive attached home welcomes you...

Ad#: 6349550 • Added: 06/26/2025 • Updated: 02/06/2026
Ad#: 6349550 • Added: 06/26/2025 • Updated: 02/06/2026
For Sale
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$1,279,000

2 Beds | 4.0 Baths | 1,824 Sqft

25 Seaside S Ct, Key West, FL, 33040

Welcome to one of the most sought after gated communities in Key West Seaside Residences. This beautiful updated 2-bedroom 3.5 half bath offers 1824sq. ft of living space. It is a three-level...

Ad#: 7817446 • Added: 06/03/2026 • Updated: 06/03/2026
Ad#: 7817446 • Added: 06/03/2026 • Updated: 06/03/2026
For Sale
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$1,250,000

4 Beds | 3.0 Baths | 2,664 Sqft

1409 4Th St, Key West, FL, 33040

Don't miss this rare opportunity to own a legal duplex on a spacious 10,000 SqFt corner lot! The main residence, solid CBS construction, offers 2 bedrooms, 2 bathrooms, and a generous 2,004 SqFt of...

Ad#: 7338215 • Added: 03/01/2026 • Updated: 05/23/2026
Ad#: 7338215 • Added: 03/01/2026 • Updated: 05/23/2026
For Sale
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$1,025,000

2 Beds | 2.0 Baths | 1,311 Sqft

1800 Atlantic Blvd 427C, Key West, FL, 33040

This spacious two-bedroom, two-bath penthouse condo boasts a stunning balcony with ocean views, making it the perfect place to relax and enjoy the breathtaking scenery. The beautifully designed...

Ad#: 7675639 • Added: 05/05/2026 • Updated: 05/23/2026
Ad#: 7675639 • Added: 05/05/2026 • Updated: 05/23/2026
For Sale
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$849,900

2 Beds | 2.0 Baths | 1,221 Sqft

2601 S Roosevelt Blvd 223C, Key West, FL, 33040

Well maintained 2BD/2BA condo that was converted from a 3BD for extra living space. Offering resort style amenities, and strong rental appeal. Unit features open living area, private balcony, impact...

Ad#: 7317904 • Added: 02/24/2026 • Updated: 05/29/2026
Ad#: 7317904 • Added: 02/24/2026 • Updated: 05/29/2026
For Sale
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$635,000

2 Beds | 2.0 Baths | 772 Sqft

3675 Seaside Dr 342, Key West, FL, 33040

Welcome to your private slice of paradise at 3675 Seaside Drive, Unit 342 -- a highly desirable end unit offering enhanced privacy, abundant natural light, and a peaceful coastal setting. Thoughtfully...

Ad#: 7327812 • Added: 02/26/2026 • Updated: 06/05/2026
Ad#: 7327812 • Added: 02/26/2026 • Updated: 06/05/2026
For Sale
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$415,000

1 Beds | 1.0 Baths | 665 Sqft

812 Fleming St 2, Key West, FL, 33040

Boutique commercial, ground floor office condo for sale in Old Town at Seafoam Condominiums. Only one of two Commercial units in the building. This 665 sf. office is turnkey and perfect for...

Ad#: 6090981 • Added: 04/25/2025 • Updated: 05/21/2026
Ad#: 6090981 • Added: 04/25/2025 • Updated: 05/21/2026
For Sale
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$345,000

1 Beds | 1.0 Baths | 528 Sqft

3312 Northside Dr Apt 712, Key West, FL, 33040

Experience Key West sunsets and ocean breezes from this TOP-FLOOR unit! This one-bedroom, one-bathroom residence boasts a spacious and practical floor plan with private balcony. Recent enhancements...

Ad#: 7522460 • Added: 04/04/2026 • Updated: 04/04/2026
Ad#: 7522460 • Added: 04/04/2026 • Updated: 04/04/2026
For Sale
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$69,000

2 Beds | 2.0 Baths | 1,120 Sqft

617 Front St C41 Week 50, Key West, FL, 33040

Own a deeded 4th-floor Gulf and waterfront corner end unit at the highly desirable Galleon Resort in the heart of Old Town Key West! This beautifully maintained 2-bedroom, 2-bath condo sleeps six and...

Ad#: 7762633 • Added: 05/21/2026 • Updated: 05/21/2026
Ad#: 7762633 • Added: 05/21/2026 • Updated: 05/21/2026
For Sale
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$65,000

2 Beds | 2.0 Baths | 1,120 Sqft

617 Front St C54 Penthouse Week 36, Key West, FL, 33040

Experience elevated waterfront ownership with this deeded timeshare in the highly desirable Building C at the Galleon Resort. This penthouse end-corner unit boasts one of the most sought-after spots...

Ad#: 7762638 • Added: 05/21/2026 • Updated: 06/07/2026
Ad#: 7762638 • Added: 05/21/2026 • Updated: 06/07/2026
For Sale
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$62,000

2 Beds | 2.0 Baths | 1,120 Sqft

617 Front St A-52 Penthouse Week 52, Key West, FL, 33040

PentHouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy the unmatched appeal of owning a deeded Key West timeshare during the final week of the year (Week...

Ad#: 7762631 • Added: 05/21/2026 • Updated: 05/21/2026
Ad#: 7762631 • Added: 05/21/2026 • Updated: 05/21/2026
For Sale
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$49,900

2 Beds | 2.0 Baths | 1,120 Sqft

617 Front St E-43 Ab Week 46 Lockout, Key West, FL, 33040

Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await from this desirable 3rd-floor lock door unit - where 2 units can be combined into one or separate. Nestled within...

Ad#: 7762641 • Added: 05/21/2026 • Updated: 05/21/2026
Ad#: 7762641 • Added: 05/21/2026 • Updated: 05/21/2026
For Sale
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$42,000

2 Beds | 2.0 Baths | 1,120 Sqft

617 Front St B41 Week 1, Key West, FL, 33040

Views of the famous Key West Sunset, Ocean, and Pool await you when you arrive at this 4th-floor end unit. Enjoy the sounds of the live music from your balcony as it saunters your way from the Tiki...

Ad#: 7762632 • Added: 05/21/2026 • Updated: 05/21/2026
Ad#: 7762632 • Added: 05/21/2026 • Updated: 05/21/2026
For Sale
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$37,500

2 Beds | 2.0 Baths | 1,120 Sqft

617 Front St B-24 Week 45, Key West, FL, 33040

Experience deeded ownership of the same week, each year (Week 45) at the highly desirable Galleon Resort with this premier timeshare opportunity. This unit showcases a wonderful location and some of...

Ad#: 7762644 • Added: 05/21/2026 • Updated: 05/21/2026
Ad#: 7762644 • Added: 05/21/2026 • Updated: 05/21/2026
For Sale
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$32,500

2 Beds | 2.0 Baths | 1,120 Sqft

617 Front St B-51 Penthouse Week 36, Key West, FL, 33040

Top floor unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit offers one of the most beautiful Key West Sunsets at...

Ad#: 7762639 • Added: 05/21/2026 • Updated: 05/21/2026
Ad#: 7762639 • Added: 05/21/2026 • Updated: 05/21/2026
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