Luxury Homes for Sale in Cudjoe Key, FL

By Jon Brooks, Co-Founder, Momentum Realty · Updated September 18, 2026

The luxury market in Cudjoe Key starts at $1,420,000 — about 1.5× the city’s median asking price. This page is every active listing at that level, refreshed nightly from the MLS, with what has actually closed, where the inventory sits and how long it takes to sell. For the wider picture see all homes for sale in Cudjoe Key.

14 luxury homes are for sale in Cudjoe Key, FL at $1,420,000 and up — median asking $2,147,000, the top listing at $12,999,999. 93% of the luxury inventory is waterfront; 14% is new construction. Median days on market: 106.

Newest luxury listings in Cudjoe Key

$2,099,000

4 bd · 3.5 ba · built 2016

1106 Thatch Lane, 33042

Listing courtesy of Coldwell Banker Schmitt Real Estate Co

$1,799,000

3 bd · 2 ba · built 2026

22970 Gasparilla Lane, 33042

Listing courtesy of Expert Realty LLC (HQ)

$2,060,000

5 bd · 3 ba · built 2011

94 Sacarma Drive, 33042

Listing courtesy of Realty Executives Florida Keys Old Town

$1,499,000

3 bd · 3 ba · built 2005

21007 4Th Avenue, 33042

Listing courtesy of Coldwell Banker Schmitt Real Estate Co

$2,195,000

5 bd · 3 ba · built 1986

125 Colson Drive, 33042

Listing courtesy of American Caribbean Real Estate, Christie's International Real Estate

$2,699,999

4 bd · 2.5 ba · built 2018

20833 W 4Th Avenue, 33042

Listing courtesy of Coldwell Banker Schmitt Real Estate Co

$5,995,000

13 bd · 7 ba · built 1977

21470 Overseas Highway, 33042

Listing courtesy of Select Properties of NWFL

$2,499,000

4 bd · 2 ba · built 2006

21023 2Nd Avenue, 33042

Listing courtesy of Coldwell Banker Schmitt Real Estate Co

$3,099,000

4 bd · 3 ba · built 2011

21090 5Th Avenue, 33042

Listing courtesy of Coldwell Banker Schmitt Real Estate Co

$1,725,000

4 bd · 3 ba · built 1982

22542 Jolly Roger Drive, 33042

Listing courtesy of Coldwell Banker Schmitt Islamorada

$3,300,000

3 bd · 3 ba · built 1992

1083 Labat Lane, 33042

Listing courtesy of Island Welcome Real Estate

$1,799,000

3 bd · 2.5 ba · built 2001

51 Sawyer Drive, 33042

Listing courtesy of Coldwell Banker Schmitt Real Estate Co

$1,575,000

3 bd · 2 ba · built 1986

22865 Redfish Lane, 33042

Listing courtesy of Coldwell Banker Schmitt Lower Keys (KW)

$12,999,999

31 bd · 19 ba · built 1958

21540 21470 Overseas Highway, 33042

Listing courtesy of Select Properties of NWFL

The most expensive homes for sale in Cudjoe Key

Luxury inventory by price

How to read this

Luxury is defined here as asking prices at or above $1,420,000. Counts, medians and closings come from active and closed MLS listings as of September 18, 2026; closings are the trailing 12 months. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 48 homes for sale in Cudjoe Key.