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Explore Our Properties
Discover the Heart of Old Town

Old Town

Exceptional Homes. Unmatched Locations.
For Sale Tropical courtyard pool surrounded by lounge chairs and seating at dusk.

223 Eanes Lane, Key West, FL 33040

$6,999,000

6 Beds
6 Baths
1,630 Sq.Ft.

Property description

Discover one of Old Towns true hidden gems at Andrews Inn, a turnkey six-unit B&B offering an exceptional blend of privacy, iconic island charm, and income potential. Tucked away in the heart of Ol...

Property Details
For Sale House at 723 Eaton Street, with an orange front door, palms, and a white picket fence.

723 Eaton Street, Key West, FL 33040

$6,450,000

7 Beds
9 Baths
3,739 Sq.Ft.

Property description

A rare opportunity in the heart of Old Town Key West's coveted Seaport neighborhood, this exceptional multi-residence property combines the charm and architectural character of historic Key West wi...

Property Details
For Sale Dining room with a wood-plank accent wall, blue kitchen, and sliding doors overlooking a pool.

1113 Stump Lane, Key West, FL 33040

$4,450,000

4 Beds
5 Baths
2,985 Sq.Ft.

Property description

Experience the ideal blend of historic charm and modern luxury in this fully renovated and expanded Key West residence, where no detail has been overlooked. Set on a quiet, one-way street in Old To...

Property Details
For Sale White gabled house with pale green shutters, a covered porch, and illuminated tropical landscaping at dusk.

812 Carsten Lane, Key West, FL 33040

$2,599,000

3 Beds
2 Baths
1,204 Sq.Ft.

Property description

Welcome to a stunning transformation of a perfectly located Old Town home. Restored from the ground up to create a single level dream home totaling 3bd/2ba overlooking a beautiful pool and patio. E...

Property Details
For Sale Outdoor pool surrounded by tropical landscaping and a light blue building at dusk.

800 Fleming Street Unit C1, Key West, FL 33040

$2,399,000

2 Beds
3 Baths
1,550 Sq.Ft.

Property description

Discover a rare blend of history, artistry, and luxury in this extraordinary residence at the celebrated William Fleming House--one of Old Town Key West's most iconic and meticulously restored hist...

Property Details
For Sale White two-story cottage with a covered porch, turquoise door and shutters, and a white picket fence.

1109 Stump Lane, Key West, FL 33040

$2,199,000

3 Beds
4 Baths
1,724 Sq.Ft.

Property description

On a quiet lane in Old Town, this classic Conch home offers a setting where life feels just a little slower and a lot more enjoyable. From the moment you step inside, the home draws you outward, wh...

Property Details
For Sale Light blue cottage with navy shutters, a covered porch, white picket fence, and brick driveway.

810 Carey Lane, Key West, FL 33040

$2,150,000

3 Beds
2 Baths
1,200 Sq.Ft.

Property description

Tucked away on a quiet private lane, this charming classic Key West cottage offers the perfect blend of historic character and modern comfort. Thoughtfully renovated, the home features a spacious, ...

Property Details
Pending White house with a lit poolside deck, French doors, and tropical landscaping at dusk.

419 Simonton Street c, Key West, FL 33040

$1,995,000

2 Beds
3 Baths
1,409 Sq.Ft.

Property description

Old Town has plenty of history. What it rarely has is a brand-new secret. Privately positioned behind one of Simonton Street's most storied facades, 419 Simonton Street C is a freestanding 2026 re...

Property Details
For Sale 626A residence entrance with a dark door, tropical landscaping, and courtyard seating.

626 Fleming Street A, Key West, FL 33040

$1,299,000

3 Beds
3 Baths
1,260 Sq.Ft.

Property description

Beautifully renovated 3bd/2.5ba townhouse incredibly located just 1.5 blocks from Duval Street with off street parking. The first floor is dedicated to an open concept living room and kitchen with ...

Property Details
For Sale Two-story corner commercial building with pale yellow siding, a white metal roof, and storefronts.

1200+1202 White Street, Key West, FL 33040

$945,000

1 Bath
2,061 Sq.Ft.

Property description

PRIME COMMERCIAL SPACE - Two combined commercial condos on White Street in X Flood Zone! These 2,061sf 1st floor units have been extensively updated and renovated with hurricane rated impact window...

Property Details
For Sale Open-plan kitchen and living room with a wood-topped island, stainless appliances, and a cable-railing staircase.

1014 Truman Avenue 202, Key West, FL 33040

$750,000

2 Beds
2 Baths
1,017 Sq.Ft.

Property description

1014 Truman Avenue - Modern Island Elegance in the Heart of Key West Welcome to a Key West retreat where modern design meets the island's laid-back charm. This immaculate two-bedroom, two-bath cond...

Property Details
For Sale White cottage with green trim, framed by palms beside a curved paver walkway and patio.

308 Margaret Street 3, Key West, FL 33040

$725,000

1 Bed
1 Bath
420 Sq.Ft.

Property description

''Seaport Sanctuary'' Located within the Land's End compound steps away from the Historic Key West Seaport and Harbor Walk. This 1 bedroom 1 bath conch cottage features an open floor plan with a st...

Property Details
For Sale White Street storefront at 1206, with a metal roof and parked cars along the road.

1206 White Street, Key West, FL 33040

$575,000

1 Bath
1,389 Sq.Ft.

Property description

PRIME OPPORTUNITY FOR OWNER/OPERATOR! Commercial condo available with over 1,300 sq. ft. centrally located in Old Town. This is an end unit and has a half bath, hurricane rated windows and doors, f...

Property Details
For Sale Building at 1202 White Street with a low storefront and an upper section.

1202 White Street, Key West, FL 33040

$450,000

1 Bath
892.36 Sq.Ft.

Property description

Prime commercial space available with 892sf centrally located in Old Town. Unit has hurricane rated windows and doors, features one assigned parking spot and is located in the X Flood Zone. The mon...

Property Details
For Sale Waterfront condominium complex with a marina, docks, and swimming pool beside turquoise water.

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

$69,000

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

What a remarkable unit. Located on the Gulf of Mexico and on the Historic Key West Marina, this 4th-floor end unit is the perfect location to vacation for the Holidays. Selling Week 50 is offers id...

Property Details
For Sale Waterfront condominium pool overlooking a turquoise harbor, with palm trees and a white-sailed boat.

617 Front Street 54, Week 36, Key West, FL 33040

$69,000

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

Experience premium waterfront ownership with this deeded timeshare in the highly coveted Building C at the Galleon Resort. This penthouse, end-corner unit offers one of the most desirable locations...

Property Details
For Sale Waterfront dock beneath a sprawling tree, with sailboats on calm water.

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

$62,000

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

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 (W...

Property Details
For Sale Waterfront condominiums beside a marina, with boats, a rock breakwater, and a pool.

617 Front St A-52 Week 32, Key West, FL 33040

$59,900

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

PentHouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy this deeded week 32 and celebrate Lobster Week and the Rum Festival yearly with the rest of Key...

Property Details
For Sale Waterfront condominium complex beside a marina, with a swimming pool and waterfront deck.

617 Front Street A52 wk32, Key West, FL 33040

$59,000

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

PentHouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy this deeded week 32 and celebrate Lobster Week and the Rum Festival yearly with the rest of Key...

Property Details
For Sale 617 Front St E-43 AB, Week 46 Lockout

617 Front Street E-43 AB, Week 46 Lockout, Key West, FL 33040

$49,900

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

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 with...

Property Details
For Sale Aerial view of waterfront condominiums with a pool, marina, and red arrow pointing to one building.

617 Front Street C-21 Week 22, Key West, FL 33040

$43,000

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

Experience deeded ownership of the same week, each year (Week 22) at the highly desirable Galleon Resort with this premier timeshare opportunity. This unit showcases a wonderful location and some o...

Property Details
For Sale 617 Front St B41 Week 1

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

$42,000

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

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 T...

Property Details
For Sale 617 Front Street B24, Wk 45

617 Front Street B24, Wk 45, Key West, FL 33040

$37,500

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

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 o...

Property Details
For Sale 617 Front St B41 Week 28

617 Front St B41 Week 28, Key West, FL 33040

$23,999

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

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...

Property Details
For Sale 617 Front Street, B51, Week 36

617 Front Street, B51, Week 36, Key West, FL 33040

$32,500

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

Penthouse Top Floor End Unit B51 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 ...

Property Details
For Sale 617 Front Street D54, Wk 37

617 Front Street D54, Wk 37, Key West, FL 33040

$31,000

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

Penthouse, top floor, end unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit delivers a truly unforgettable Key...

Property Details
For Lease White storefront at 1206 White Street, with a red arrow pointing to its entrance.

1206 White Street, Key West, FL 33040

$3,950/mo

1 Bath
1,100 Sq.Ft.

Property description

Commercial space available for lease with approximately 1,100 sq. ft. centrally located in Old Town. This is an end unit and has a half bath, hurricane rated windows and doors, features one assigne...

Property Details

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