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Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

With a portal you are able to:
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Old Town Key West:

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95 matches found

$7,495,000
616 Eaton Street
Key West, FL 33040
Designer furnishings just added
View Photos (61)Videos (1)Virtual Tours (1)
Property Type: Residential
# of Bedrooms: 5
# of Bathrooms: 7
Square Footage: 4000
Year Built: 1939
Area: 01 - Key West
Subdivision: Old Town - Unrecord (1.0)
Description: Located in the heart of Old Town, 616 Eaton Street tells a story that spans...
Listing Office: Truman & Co. (KW)
Last Updated: May - 19 - 2026
IDX
$6,895,000
317 Whitehead Street
Key West, FL 33040
317 Whitehead Street, Key West, FL 33040
View Photos (78)Videos (1)
Property Type: Residential
# of Bedrooms: 6
# of Bathrooms: 7
Square Footage: 3425
Year Built: 2025
Area: 01 - Key West
Subdivision: Old Town - Unrecord (1.0)
Description: Discover unparalleled luxury in the heart of Old Town, Key West. Compri...
Listing Office: RE/MAX Keys Connection (KW)
Last Updated: April - 23 - 2026
IDX
$6,750,000
411 Louisa Street
Key West, FL 33040
411 Louisa Street, Key West, FL 33040
View Photos (71)Videos (1)
Property Type: Residential
# of Bedrooms: 5
# of Bathrooms: 5
Square Footage: 3663
Year Built: 1943
Area: 02 - Key West
Subdivision: Old Town - Unlisted (1.0)
Description: Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa ...
Listing Office: RE/MAX Keys Connection (KW)
Last Updated: November - 03 - 2025
IDX
$5,995,000
910-914 Watson Street
Key West, FL 33040
Back Patio
View Photos (38)Videos (1)Virtual Tours (2)
Property Type: Residential
# of Bedrooms: 5
# of Bathrooms: 7
Square Footage: 4387
Year Built: 1929
Area: 02 - Key West
Subdivision: Old Town - Unlisted (1.0)
Description: More than a residence and rarer than legend, 910-914 Watson Street stands a...
Listing Office: Truman & Co. (KW)
Last Updated: February - 24 - 2026
IDX
$5,950,000
723 Eaton Street
Key West, FL 33040
723 Eaton Street, Key West, FL 33040
View Photos (90)
Property Type: Residential
# of Bedrooms: 6
# of Bathrooms: 8
Square Footage: 4094
Year Built: 2020
Area: 01 - Key West
Subdivision: Old Town - Unrecord (1.0)
Description: Private Old Town property with built-in income and exceptional flexibility....
Listing Office: Preferred Properties (KW)
Last Updated: May - 20 - 2026
IDX
$5,850,000
421 - 423 Simonton Street
Key West, FL 33040
421 - 423 Simonton Street, Key West, FL 33040
View Photos (38)
Property Type: Residential
# of Bedrooms: 6
# of Bathrooms: 8
Square Footage: 3010
Year Built: 2020
Area: 02 - Key West
Subdivision: Old Town - Unlisted (1.0)
Description: Two Transient Homes Now Available For Sale. Just one block off world-famous...
Listing Office: Berkshire Hathaway HomeServices Knight & Gardner Realty
Last Updated: April - 01 - 2026
IDX
$4,695,000
709 Eaton Street
Key West, FL 33040
709 Eaton Street, Key West, FL 33040
View Photos (37)
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 5
Square Footage: 2716
Year Built: 1847
Area: 01 - Key West
Subdivision: Old Town - Unrecord (1.0)
Description: Step into the enchanting world of Key West history at 709 Eaton Street, a m...
Listing Office: Berkshire Hathaway HomeServices Knight & Gardner Realty
Last Updated: April - 29 - 2026
IDX
$4,500,000
600 Elizabeth Street
Key West, FL 33040
600 Elizabeth Street, Key West, FL 33040
View Photos (86)Videos (1)
Open House (05/24/2026 - 11:00 am)
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 6
Square Footage: 3092
Year Built: 1996
Area: 01 - Key West
Subdivision: Old Town - Unrecord (1.0)
Description: Elegantly positioned beneath the sweeping canopy of its namesake tree, Casa...
Listing Office: Berkshire Hathaway HomeServices Knight & Gardner Realty
Last Updated: May - 19 - 2026
IDX
$4,450,000
1113 Stump Lane
Key West, FL 33040
Move-in ready!
View Photos (42)Videos (1)Virtual Tours (1)
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 5
Square Footage: 2985
Year Built: 1938
Area: 02 - Key West
Subdivision: Old Town - Unlisted (1.0)
Description: Experience the ideal blend of historic charm and modern luxury in this full...
Listing Office: Truman & Co. (KW)
Last Updated: May - 19 - 2026
IDX
$3,999,000
1010 Olivia Street
Key West, FL 33040
1010 Olivia Street, Key West, FL 33040
View Photos (45)Videos (1)Virtual Tours (1)
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 4
Square Footage: 2421
Year Built: 2025
Area: 02 - Key West
Subdivision: Old Town - Unlisted (1.0)
Description: Introducing The Twins on Olivia - a storied Key West treasure reborn. Once ...
Listing Office: Suzanne Moore Real Estate
Last Updated: May - 17 - 2026
IDX

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The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.
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The Old Town neighborhood has Key West homes for sale, Key West townhomes for sale and Key West condos for sale.

For assistance with your Key West real estate needs, please contact the team of Key West realtors at Anchor Line Realty.

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David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)