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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 720D Simonton Street

720D Simonton Street, Key West, FL 33040

$4,950,000

4 Beds
4 Baths
2,441 Sq.Ft.

Property description

DUAL TRANSIENT LICENSES | A RARE DEPARTURE FROM THE ORDINARY While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural de...

Property Details
Active Under Contract 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 830 Johnson Lane

830 Johnson Lane, Key West, FL 33040

$1,500,000

2 Beds
1 Bath
1,050 Sq.Ft.

Property description

Quiet Old Town lane living in this historic cottage with guest house and off street parking. The main home consists of a 1bd/1ba with an additional sleeping loft and a storage loft. The guest house...

Property Details
Active Under Contract 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

$899,000

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
Active Under Contract 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

$445,000

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 617 Front Street B52 Week 52 Penthouse

617 Front Street B52 Week 52 Penthouse, Key West, FL 33040

$69,000

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

Happy New Year! Enjoy holiday festivities with fun in the sun from your Penthouse balcony while enjoying the Key West Sunsets. Deeded ownership of B52, Penthouse unit, week 52 every year; same unit...

Property Details
For Sale 617 Front Street C22 Week 1

617 Front Street C22 Week 1, Key West, FL 33040

$69,000

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

Experience deeded ownership of the same week, each year (Week 1 Unit C22) at the highly desirable Galleon Resort with this premier timeshare opportunity. This unit showcases a wonderful location an...

Property Details
For Sale 617 Front Street C34 Week 1

617 Front Street C34 Week 1, Key West, FL 33040

$69,000

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

Experience deeded ownership of the same week, each year (Week 1) at the highly desirable Galleon Resort with this premier timeshare opportunity. This unit showcases a wonderful location and some of...

Property Details
For Sale 617 Front Street C34 Week 2

617 Front Street C34 Week 2, Key West, FL 33040

$69,000

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

Experience deeded ownership of the same week, each year (Week 2) at the highly desirable Galleon Resort with this premier timeshare opportunity. This unit showcases a wonderful location and some of...

Property Details
For Sale 617 Front Street C43 Week 50

617 Front Street C43 Week 50, Key West, FL 33040

$69,000

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

Enjoy your holiday celebrations with fun in the sun from your balcony and unit situated on the Gulf Front. Deeded ownership of C43, 4th-floor unit, week 50 every year; same unit, same week, or rent...

Property Details
For Sale 617 Front Street D54 week3 Penthouse

617 Front Street D54 week3 Penthouse, Key West, FL 33040

$69,000

2 Beds
2 Baths
1,120 Sq.Ft.

Property description

Happy Southern Most Regatta Week. Enjoy the boat race festivities with fun in the sun from your Penthouse balcony while enjoying the Key West Sunsets. Deeded ownership of D54, Penthouse unit, week ...

Property Details
For Sale 617 Front Street F53 Week 2Penthouse

617 Front Street F53 Week 2Penthouse, Key West, FL 33040

$69,000

3 Beds
2 Baths
1,350 Sq.Ft.

Property description

3 bed/2 bath only 7 of these units exist. Sleeps 8 Experience deeded ownership of the same week, each year (Week 2) at the highly desirable Galleon Resort with this premier timeshare opportunity. T...

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 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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