Homes for Sale in Summerland Key, FL
22 homes are for sale in Summerland Key, FL as of 2026-10-15, with 2 more under contract. The median list price is $1,754,500, most homes list between $799K to $4.40M, and the median listing has been on the market 105 days. That is 22 houses, 0 condos and 0 townhouses. 0 homes came on the market this week.
| Location | Monroe County, FL |
|---|---|
| ZIP codes with their own page | 1 |
| For sale right now | 22 active, 2 under contract |
| Asking prices | $1,754,500, median · most homes $799K–$4.40M |
| Median days on market (active listings) | 105 |
| Property types for sale | 22 houses, 0 condos, 0 townhouses |
| New listings this week | 0 |
Listing counts and prices as of 2026-10-15; MLS data, refreshed nightly. Market figures describe homes, not residents. Cite as: Momentum Realty, “Summerland Key, FL key facts,” movewithmomentum.com/homes-for-sale/summerland-key-fl/, data as of 2026-10-15.
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.
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 $1,754,500; the busiest band is $1M and up.
$500K – $750K: 2 homes
$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
- $1.05M · 2 bd / 2 ba · 667 E Caribbean Drive
- $1.56M · 3 bd / 2 ba · 947 Gulf Drive
- $5.50M · 3 bd / 3 ba · 481 E Shore Drive
- $1.30M · 2 bd / 2 ba · 486 S Airport Drive
Every home for sale in Summerland Key right now (22)
All 22 active Summerland Key listings with a detail page, newest first, refreshed twice a day from the MLS.
- $1.05M · 2 bd / 2 ba · 667 E Caribbean Drive
- $1.56M · 3 bd / 2 ba · 947 Gulf Drive
- $5.50M · 3 bd / 3 ba · 481 E Shore Drive
- $899,000 · 2 bd / 1 ba · 24923 Park Drive
- $799,000 · 3 bd / 1 ba · 27 N Lake Drive
- $1.30M · 2 bd / 2 ba · 486 S Airport Drive
- $3.50M · 3 bd / 3 ba · 25361 1st Street
- $2.80M · 5 bd / 4 ba · 23950 Overseas Highway
- $649,000 · 2 bd / 2 ba · 24740 Park Drive
- $3.10M · 2 bd / 3 ba · 361 Avenue D
- $899,000 · 3 bd / 2 ba · 23940 Overseas Highway
- $535,000 · 3 bd / 2 ba · 96 John Street
- $16.90M · 5 bd / 4 ba · 0 Howell Key
- $1.25M · 2 bd / 2 ba · 466 W Shore Drive
- $1.15M · 3 bd / 2 ba · 706 E Caribbean Drive
- $2.25M · 3 bd / 1.5 ba · 848 E Caribbean Drive
- $3.50M · 4 bd / 3.5 ba · 414 E Caribbean Drive
- $2.22M · 3 bd / 2 ba · 937 Gulf Drive
- $3.29M · 3 bd / 3 ba · 24348 Caribbean Drive
- $950,000 · 3 bd / 2 ba · 24840 Park Drive
- $4.40M · 5 bd / 5.5 ba · 231 E Shore Drive #6
- $1.95M · 3 bd / 3 ba · 860 Lagoon Drive
Homes for sale in Summerland Key by ZIP code
Where the inventory is: active listings and the median asking price by ZIP. ZIPs link to their housing scorecard.
| ZIP | Homes for sale | Median list price |
|---|---|---|
| 33042 | 22 | $1.75M |
What is for sale in Summerland Key: property types
- Single-family houses: 22
What a home in Summerland Key costs to own
Take the median $1,754,500 listing with 20% down at today’s 7.40% 30-year rate: principal and interest run about $9,718/month. Monroe County’s typical millage of 8.82 puts property tax near $15,027/year after the $50,000 homestead exemption — and that is the reset bill a buyer pays, not the seller’s capped one. Citizens’ average premium in Monroe County is about $4,380/year; newer roofs and inland addresses usually quote below it. All in, plan on roughly $11,335/month plus any HOA or CDD assessment.
Explore Summerland Key
- All homes for sale in Monroe County, FL
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- Summerland Key market intelligence: prices, supply and trends
- Monroe County property tax guide
- Monroe County down payment assistance limits
- First-time home buyer guide for Florida
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Recently off market in Summerland Key
Homes in Summerland Key that left the market most recently, with their last list price and a public-record page for each address. Off-market pages keep the community, tax and sales-history context after a listing closes or expires.
- 637 E Caribbean Drive · last listed $1,100,000 · off market Oct 14, 2026
- 17287 Cayman Dr Drive #17287 · last listed $7,800 · off market Oct 14, 2026
- 24347 W Caribbean Drive · last listed $1,199,000 · off market Oct 7, 2026
- 481 E Shore Drive #481 E Shore Drive · last listed $5,500,000 · off market Sep 25, 2026
- 360 W Shore Drive · last listed $749,500 · off market Sep 12, 2026
- 0 Melody · last listed $7,000,000 · off market Sep 12, 2026
- 887 Bay Drive · off market Sep 10, 2026
- 673 Indies Road · off market Sep 10, 2026
- 596 W Shore Drive · off market Sep 10, 2026
- 324 S Airport Drive · off market Sep 10, 2026
- 1331 Hudgins Drive · off market Sep 10, 2026
- 1046 Flagship Drive · off market Sep 10, 2026
Common questions
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Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Summerland Key as of 2026-10-15 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.