Homes for Sale in Summerland Key, FL

23 homes are for sale in Summerland Key, FL as of 2026-09-06, with 2 more under contract. The median list price is $1,250,000, most homes list between $750K to $3.50M, and the median listing has been on the market 84 days. 0 homes came on the market this week.

Newest homes for sale in Summerland Key

The most recently listed homes in Summerland Key, newest first, with photos. Each card opens the full listing with every photo, the community’s sales history and a tour request. Homes marked New listed in the last seven days.

$899,000

2 bd · 1 ba

24923 Park Drive

Summerland Key

Listing courtesy of Island Real Estate Company Florida Keys

$799,000

3 bd · 1 ba

27 N Lake Drive

Summerland Key

Listing courtesy of Taylor & Assoc. RE, Inc.

$1.30M

2 bd · 2 ba

486 S Airport Drive

Summerland Key

Listing courtesy of Keller Williams Key West Compass Realty

$3.50M

3 bd · 3 ba

25361 1st Street

Summerland Key

Listing courtesy of Coastal Collection Real Estate Inc.

$3.00M

5 bd · 4 ba

23950 Overseas Highway

Summerland Key

Listing courtesy of Ocean Sotheby's International Realty

$649,000

2 bd · 2 ba

24740 Park Drive

Summerland Key

Listing courtesy of Coldwell Banker Schmitt Real Estate Co

$3.10M

2 bd · 3 ba

361 Avenue D

Summerland Key

Listing courtesy of Island Real Estate Company Florida Keys

$899,000

3 bd · 2 ba

23940 Overseas Highway

Summerland Key

Listing courtesy of Island Real Estate Company Florida Keys

$535,000

3 bd · 2 ba

96 John Street

Summerland Key

Listing courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty

$16.90M

5 bd · 4 ba

0 Howell Key

Summerland Key

Listing courtesy of Coldwell Banker Schmitt Real Estate Co

$1.25M

2 bd · 2 ba

466 W Shore Drive

Summerland Key

Listing courtesy of Keller Williams Key West Compass Realty

$1.19M

3 bd · 2 ba

706 E Caribbean Drive

Summerland Key

Listing courtesy of Keller Williams Key West Compass Realty

$2.25M

3 bd · 1.5 ba

848 E Caribbean Drive

Summerland Key

Listing courtesy of Homecoin.com

$3.50M

4 bd · 3.5 ba

414 E Caribbean Drive

Summerland Key

Listing courtesy of The Agency Florida Keys

$1.20M

2 bd · 2 ba

637 E Caribbean Drive

Summerland Key

Listing courtesy of Keller Williams Key West Compass Realty

$1.10M

2 bd · 2 ba

667 E Caribbean Drive

Summerland Key

Listing courtesy of Keller Williams Key West Compass Realty

$2.22M

3 bd · 2 ba

937 Gulf Drive

Summerland Key

Listing courtesy of Island Welcome Real Estate

$3.29M

3 bd · 3 ba

24348 Caribbean Drive

Summerland Key

Listing courtesy of Key West Sales, LLC

$1.20M

3 bd · 2 ba

24347 W Caribbean Drive

Summerland Key

Listing courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty

$749,500

3 bd · 1 ba

360 W Shore Drive

Summerland Key

Listing courtesy of Island Welcome Real Estate

$950,000

3 bd · 2 ba

24840 Park Drive

Summerland Key

Listing courtesy of LAER Realty

$4.40M

5 bd · 5.5 ba

231 E Shore Drive #6

Summerland Key

Listing courtesy of Serhant Florida LLC - Delray Beach Office

$1.95M

3 bd · 3 ba

860 Lagoon Drive

Summerland Key

Listing courtesy of Action Keys Realty of the Lower FL Keys LLC

Summerland Key homes for sale by price

Every active listing in Summerland Key grouped by price, with the newest listings in each band. The median is $1,250,000; the busiest band is $1M and up.

$500K – $750K: 3 homes

• $649,000 · 2 bd / 2 ba · 24740 Park Drive
• $535,000 · 3 bd / 2 ba · 96 John Street
• $749,500 · 3 bd / 1 ba · 360 W Shore Drive

$750K – $1M: 4 homes

• $899,000 · 2 bd / 1 ba · 24923 Park Drive
• $799,000 · 3 bd / 1 ba · 27 N Lake Drive
• $899,000 · 3 bd / 2 ba · 23940 Overseas Highway
• $950,000 · 3 bd / 2 ba · 24840 Park Drive

$1M and up: 16 homes

• $1.30M · 2 bd / 2 ba · 486 S Airport Drive
• $3.50M · 3 bd / 3 ba · 25361 1st Street
• $3.00M · 5 bd / 4 ba · 23950 Overseas Highway
• $3.10M · 2 bd / 3 ba · 361 Avenue D

What is for sale in Summerland Key: property types

• Single-family homes: 23

Another 1 listings in Summerland Key are land, commercial or other non-residential property and are not counted above.

What a home in Summerland Key costs to own

Take the median $1,250,000 listing with 20% down at today’s 6.71% 30-year rate: principal and interest run about $6,459/month. All in, plan on roughly $6,459/month plus any HOA or CDD assessment.

Explore Summerland Key

• Search every Summerland Key community
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Common questions

Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Summerland Key as of 2026-09-06 and refresh as homes list and sell. Listing data provided by Florida Keys MLS, Inc. Information is deemed reliable but is not guaranteed by the MLS to be accurate. The data relating to real estate for sale on this page comes in part from the Internet Data Exchange (IDX) program of the MLS(s) named above; listings held by brokerages other than Momentum Realty are marked with the listing brokerage’s name. Information is deemed reliable but not guaranteed. Estimates are not guarantees. Equal Housing Opportunity.