33042 Homes for Sale — Summerland Key, FL

Every active MLS listing in Summerland Key’s 33042 ZIP code, refreshed nightly, with the price bands, the property mix and the communities that have the most homes for sale. For the whole city see homes for sale in Summerland Key, FL (24 listings); for the ZIP’s values, taxes and growth see the 33042 housing scorecard.

33042 at a glance

ZIP 33042 is Summerland Key, Monroe County, FL. The numbers below are computed from MLS closings and live listings for every community in the ZIP and refresh with each data pull.

Where it isSummerland Key, Monroe County, FL
Communities38 MLS communities, 19 with 12-month sales data
Median sold price, 12 months$908K (+3.7% year over year)
Days to contract (median)79
New construction share of sales7%
Sale-to-original-list92.2%
Communities with the most salesCutthroat Harbor Estates ($900K), VENTURE OUT ($650K), SUMMERLAND KEY COVE ($1.1M), JOLLY ROGER ESTATES ($1.2M), CORAL SHORES ESTATES ($360K), SUMMERLAND COVE ISLE ($2.36M)

33042 housing market tracker · all homes for sale in Summerland Key, FL · Monroe County property tax

24 homes are for sale in ZIP 33042 (Summerland Key, FL) right now, from $649,000 to $4,400,000 for the middle 80%, at a median asking price of $1,429,500. , built 1997; 1 came on the market in the last 7 days and 12% are new construction.

Newest homes for sale in 33042

17287 Cayman Dr Drive #17287, home for sale in Summerland Key 33042
$7,800 New
3 bd · 2 ba · built 2013
17287 Cayman Dr Drive #17287
Listing courtesy of Luxur Realty LLC dba: Realty One Group Evolution
667 E Caribbean Drive, home for sale in Summerland Key 33042
$1,050,000
2 bd · 2 ba · built 1986
667 E Caribbean Drive
Listing courtesy of Keller Williams Key West Compass Realty
947 Gulf Drive, home for sale in Summerland Key 33042
$1,559,000
3 bd · 2 ba · built 1988
947 Gulf Drive
Listing courtesy of Coldwell Banker Schmitt Real Estate Co.
481 E Shore Drive, home for sale in Summerland Key 33042
$5,500,000
3 bd · 3 ba · built 1992
481 E Shore Drive
Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate
24923 Park Drive, home for sale in Summerland Key 33042
$899,000
2 bd · 1 ba · built 1956
24923 Park Drive
Listing courtesy of Island Real Estate Company Florida Keys
27 N Lake Drive, home for sale in Summerland Key 33042
$799,000
3 bd · 1 ba · built 1956
27 N Lake Drive
Listing courtesy of Island Welcome Real Estate LLC
486 S Airport Drive, home for sale in Summerland Key 33042
$1,300,000
2 bd · 2 ba · built 1982
486 S Airport Drive
Listing courtesy of Keller Williams Key West Compass Realty
25361 1St Street, home for sale in Summerland Key 33042
$3,500,000
3 bd · 3 ba · built 1999
25361 1St Street
Listing courtesy of Coastal Collection Real Estate Inc.
23950 Overseas Highway, home for sale in Summerland Key 33042
$2,799,000
5 bd · 4 ba · built 2026
23950 Overseas Highway
Listing courtesy of Ocean Sotheby's International Realty
24740 Park Drive, home for sale in Summerland Key 33042
$649,000
2 bd · 2 ba · built 1991
24740 Park Drive
Listing courtesy of Coldwell Banker Schmitt Real Estate Co
361 Avenue D, home for sale in Summerland Key 33042
$3,100,000
2 bd · 3 ba · built 2020
361 Avenue D
Listing courtesy of Island Real Estate Company Florida Keys
23940 Overseas Highway, home for sale in Summerland Key 33042
$899,000
3 bd · 2 ba · built 2022
23940 Overseas Highway
Listing courtesy of Island Real Estate Company Florida Keys
96 John Street, home for sale in Summerland Key 33042
$535,000
3 bd · 2 ba · built 2006
96 John Street
Listing courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
0 Howell Key, home for sale in Summerland Key 33042
$16,900,000
5 bd · 4 ba · built 2015
0 Howell Key
Listing courtesy of Coldwell Banker Schmitt Real Estate Co
466 W Shore Drive, home for sale in Summerland Key 33042
$1,250,000
2 bd · 2 ba · built 1970
466 W Shore Drive
Listing courtesy of Keller Williams Key West Compass Realty
706 E Caribbean Drive, home for sale in Summerland Key 33042
$1,145,000
3 bd · 2 ba · built 1999
706 E Caribbean Drive
Listing courtesy of Keller Williams Key West Compass Realty
848 E Caribbean Drive, home for sale in Summerland Key 33042
$2,246,000
3 bd · 1.5 ba · built 1988
848 E Caribbean Drive
Listing courtesy of Homecoin.com
414 E Caribbean Drive, home for sale in Summerland Key 33042
$3,495,000
4 bd · 3.5 ba · built 1970
414 E Caribbean Drive
Listing courtesy of The Agency Florida Keys
637 E Caribbean Drive, home for sale in Summerland Key 33042
$1,100,000
2 bd · 2 ba · built 1993
637 E Caribbean Drive
Listing courtesy of Keller Williams Key West Compass Realty
937 Gulf Drive, home for sale in Summerland Key 33042
$2,220,000
3 bd · 2 ba · built 2008
937 Gulf Drive
Listing courtesy of Island Welcome Real Estate
24348 Caribbean Drive, home for sale in Summerland Key 33042
$3,295,000
3 bd · 3 ba · built 1996
24348 Caribbean Drive
Listing courtesy of Key West Sales, LLC
24840 Park Drive, home for sale in Summerland Key 33042
$950,000
3 bd · 2 ba · built 2005
24840 Park Drive
Listing courtesy of LAER Realty
231 E Shore Drive #6, home for sale in Summerland Key 33042
$4,400,000
5 bd · 5.5 ba · built 2025
231 E Shore Drive #6
Listing courtesy of Serhant Florida LLC - Delray Beach Office
860 Lagoon Drive, home for sale in Summerland Key 33042
$1,950,000
3 bd · 3 ba · built 2003
860 Lagoon Drive
Listing courtesy of Action Keys Realty of the Lower FL Keys LLC

Every home for sale in 33042 right now (24)

All 24 active listings in ZIP 33042 with a detail page, newest first, refreshed twice a day from the MLS.

Homes for sale in 33042 by price

Price bandFor saleShare
Under $200K14%
$500K–$750K28%
$750K+2188%

How to read this

Counts and medians are from active MLS listings with a 33042 mailing ZIP as of October 11, 2026; property mix Single-family 100%. Prices are asking prices. Listings are shown with the courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also homes for sale in Monroe County. More: luxury homes in Summerland Key.

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