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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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Summerland Key:

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23 matches found

$16,900,000
0 Howell Key
Summerland Key, FL 33042
0 Howell Key, Summerland Key, FL 33042
View Photos (145)Videos (1)Virtual Tours (1)
Property Type: Residential
# of Bedrooms: 5
# of Bathrooms: 4
Square Footage: 3352
Year Built: 2015
Area: 08 - Summerland Key
Subdivision: Misc Summerland Key (25.0)
Description: Discover one of the Florida Keys' most extraordinary private island retreat...
Listing Office: Coldwell Banker Schmitt Real Estate Co
Last Updated: July - 09 - 2026
IDX
$5,200,000
1046 Flagship Drive
Summerland Key, FL 33042
Introducing for the first time, 1046 Flagship Drive - a premier location.
View Photos (80)Videos (1)
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 4
Square Footage: 3208
Year Built: 2001
Area: 08 - Summerland Key
Subdivision: Summerland Cove Isle (25.5)
Description: Experience the PINNACLE of luxury waterfront living at this exceptional oce...
Listing Office: Keller Williams Key West Compass Realty
Last Updated: July - 13 - 2026
IDX
$3,495,000
414 E Caribbean Drive
Summerland Key, FL 33042
414 E Caribbean Drive, Summerland Key, FL 33042
View Photos (50)Videos (1)
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 4
Square Footage: 2766
Year Built: 1970
Area: 08 - Summerland Key
Subdivision: Summerland Key Cove (25.0)
Description: OCEANFRONT , POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water l...
Listing Office: The Agency Florida Keys
Last Updated: June - 29 - 2026
IDX
$3,300,000
23950 Overseas Highway
Summerland Key, FL 33042
Ocean side with ocean views
View Photos (73)
Property Type: Residential
# of Bedrooms: 5
# of Bathrooms: 4
Square Footage: 3886
Year Built: 2026
Area: 08 - Summerland Key
Subdivision: Dobie's Sub (24.0)
Description: Welcome to Pink Sands, a Glenn Gray-designed waterfront retreat where the v...
Listing Office: Ocean Sotheby's International Realty
Last Updated: July - 11 - 2026
IDX
$3,295,000
24348 Caribbean Drive
Summerland Key, FL 33042
Open water Summerland Cove
View Photos (63)Virtual Tours (1)
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 3
Square Footage: 2870
Year Built: 1996
Area: 08 - Summerland Key
Subdivision: Summerland Key Cove (25.0)
Description: A stunning location with all attributes geared to the view of the beautiful...
Listing Office: Key West Sales, LLC
Last Updated: June - 16 - 2026
IDX
$3,100,000
361 Avenue D
Summerland Key, FL 33042
361 Avenue D, Summerland Key, FL 33042
View Photos (63)
Property Type: Residential
# of Bedrooms: 2
# of Bathrooms: 3
Square Footage: 1819
Year Built: 2020
Area: 08 - Summerland Key
Subdivision: Summerland Beach (25.0)
Description: Beach House Paradise in Summerland Key. Nestled in one of the Lower Keys' m...
Listing Office: Island Real Estate Company Florida Keys
Last Updated: July - 05 - 2026
IDX
$2,246,000
848 E Caribbean Drive
Summerland Key, FL 33042
848 E Caribbean Drive, Summerland Key, FL 33042
View Photos (44)
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 2
Square Footage: 2016
Year Built: 1988
Area: 08 - Summerland Key
Subdivision: Summerland Key Cove (25.0)
Description: Built for the offshore lifestyle, this exceptional Summerland Key waterfron...
Listing Office: Homecoin.com
Last Updated: July - 20 - 2026
IDX
$2,220,000
937 Gulf Drive
Summerland Key, FL 33042
937 Gulf Drive, Summerland Key, FL 33042
View Photos (44)
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 2
Square Footage: 1900
Year Built: 2008
Area: 08 - Summerland Key
Subdivision: Summerland Cove Isle (25.5)
Description: High quality concrete 3/2 in Summerland Cove. One of the best boating commu...
Listing Office: Island Welcome Real Estate
Last Updated: June - 20 - 2026
IDX
$1,950,000
860 Lagoon Drive
Summerland Key, FL 33042
860 Lagoon Drive, Summerland Key, FL 33042
View Photos (27)Virtual Tours (1)
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 3
Square Footage: 1797
Year Built: 2003
Area: 08 - Summerland Key
Subdivision: Summerland Cove Isle (25.5)
Description: This stately concrete home has all the best of everything on one of the bes...
Listing Office: Action Keys Realty of the Lower FL Keys LLC
Last Updated: June - 26 - 2026
IDX
$1,595,000
887 Bay Drive
Summerland Key, FL 33042
887 Bay Drive, Summerland Key, FL 33042
View Photos (65)
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 3
Square Footage: 2022
Year Built: 1974
Area: 08 - Summerland Key
Subdivision: Summerland Cove Isle (25.5)
Description: Priced at Current appraised value, this 3-bedroom, 3-bath concrete fortress...
Listing Office: Realty Executives Florida Keys Summerland Branch
Last Updated: June - 29 - 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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Summerland Key real estate consists of Florida Keys homes for sale, Florida Keys condos for sale and Florida Keys townhomes for sale.

For assistance with your Florida Keys real estate needs, please contact the team of Florida Keys 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)