$1,998,000
- 4 Beds
- 3 Baths
- 2,440 Sq Ft
22542 Jolly Roger Dr, Summerland Key, FL 33042
Emily Lombard
Ocean Sotheby's International Realty
(786) 788-8217
$1,998,000
22542 Jolly Roger Dr, Summerland Key, FL 33042
Emily Lombard
Ocean Sotheby's International Realty
(786) 788-8217
$1,375,000 Open Sat 10AM - 1PM
22974 Anne Bonny Ln, Summerland Key, FL 33042
Sandra Tuttle
Island Welcome Real Estate
(786) 869-3656
$1,150,000
21855 Spain Blvd, Summerland Key, FL 33042
Matthew Sheehan
Ocean Sotheby's International Realty
(786) 882-7957
$3,750,000
755 Sawyer Dr, Summerland Key, FL 33042
Terrance Sullivan
Ocean Sotheby's International Realty
(786) 204-2360
$3,750,000
755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
Terrance Sullivan
Ocean Sotheby's International Realty
(786) 465-7217
$999,000
22954 Buccaneer Ln, Summerland Key, FL 33042
Lisa Ferringo
Coldwell Banker Schmitt Lower Keys (KW)
(645) 230-1509
$2,000,000
22892 Jolly Roger Dr, Summerland Key, FL 33042
Michelle Howerton
Brenda Donnelly Real Estate LLC
(855) 548-0123
$1,599,000
20838 5th Ave W, Summerland Key, FL 33042
Lisa Ferringo
Coldwell Banker Schmitt Lower Keys (KW)
(786) 952-7261
$1,500,000
21865 Spain Blvd, Summerland Key, FL 33042
Matthew Sheehan
Ocean Sotheby's International Realty
(645) 215-8837
$2,250,000
743 Pattison Dr, Summerland Key, FL 33042
Sandra Tuttle
Island Welcome Real Estate
(786) 756-9163
$1,499,000
51 Drost Dr, Summerland Key, FL 33042
Lisa Ferringo
Coldwell Banker Schmitt Lower Keys (KW)
(786) 551-4933
$1,145,000
22737 Blackbeard Ln, Cudjoe Key, FL 33042
Terry Garcia
Keller Williams Key West Compass Realty
(786) 321-8407
$1,799,999
22562 Jolly Roger Dr, Summerland Key, FL 33042
Krystal Thomas eXp Realty LLC
$1,950,000
489 Sawyer Dr, Summerland Key, FL 33042
Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)
$949,000
151 Cutthroat Dr, Summerland Key, FL 33042
Heather Bennett Keller Williams Key West Compass Realty
$1,569,999 New Construction
142 Peg Leg Ln, Cudjoe Key, FL 33042
Alejandro Perez Amerifirst Realty
$1,125,000
22837 Calico Jack Cir, Summerland Key, FL 33042
Beata Sharpe Coldwell Banker Vanguard Realty
$1,099,000
165 Cutlass Ln, Summerland Key, FL 33042
Justyn Ewald Expert Realty LLC (HQ)
$350,000
37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
Joseph Ordini Keller Williams Key West Compass Realty
$849,000
22920 Privateer Dr, Summerland Key, FL 33042
Robin Nilsson Keller Williams Key West Compass Realty
$1,100,000
21073 7th Ave, Summerland Key, FL 33042
Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)
$2,450,000
1176 Thatch Ln, Summerland Key, FL 33042
Jonathan Minerick Homecoin.com
$2,200,000
94 Sacarma Dr, Cudjoe Key, FL 33042
Michelle Blades Realty Executives Florida Keys Old Town
$2,249,000 Pre-Foreclosure
125 Colson Dr, Summerland Key, FL 33042
Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty
$1,549,000
20841 8th Ave W, Cudjoe Key, FL 33042
Collin Tingle Coldwell Banker Schmitt Lower Keys (KW)
$2,950,000 Open Sun 1PM - 3PM
20844 4th Ave W, Summerland Key, FL 33042
Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty
$899,999
23012 Snapper Ln, Summerland Key, FL 33042
Bobby Coe RE/MAX Keys Connection (KW)
$1,599,000
1113 de Lussan Ln, Summerland Key, FL 33042
Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)
$899,000
463 Lesrohde Dr, Ramrod Key, FL 33042
Sarah Dolson Keller Williams Key West Compass Realty
$1,190,000
22748 Blackbeard Ln, Cudjoe Key, FL 33042
Lindsay Ryan EXP Realty LLC
$989,999
22961 John Avery Ln, Summerland Key, FL 33042
Rayden Vega CASA MIAMI REAL ESTATE
$3,750,000
22815 Port Royal Ln, Summerland Key, FL 33042
Rhonda Gailey Gailey Enterprises Real Estate
Cudjoe Key, FL, is a small community known for its waterfront properties and unique attractions. The island, which began as a U.S. Air Force base in the late 1950s, features a mix of single-family homes and resort rentals, with much of the land remaining undeveloped. The National Key Deer Refuge, a 9,000-acre preserve, protects the endangered Key deer on the island. A notable feature is the aerostat site at the northern tip, where a large white blimp, nicknamed “Fat Albert,” hovers. Residential areas like Cutthroat Harbor Estates and Cudjoe Gardens offer stilt homes and canal-front properties, with prices ranging from $600,000 to over $3 million. The island lacks traditional parks, but residents enjoy water activities such as deep-sea diving, boating, and fishing. Bahia Honda State Park, located 15 miles away, provides additional outdoor recreation with its beach, hiking trails, and snorkeling sites. Dining options include Broil, a gourmet steakhouse, and The Bent Prop, known for its happy hour specials. For groceries, Murray’s Market is 2 miles away on Summerland Key, and a Winn-Dixie is 9 miles away on Big Pine Key. Students attend highly rated schools like Key West High School and Big Pine Academy. The Overseas Highway connects Cudjoe Key to Key West, 20 miles south, and Marathon, 30 miles north. Residents face high home and flood insurance premiums due to the island's susceptibility to hurricanes.
On average, homes in Cudjoe Key, FL sell after 110 days on the market compared to the national average of 53 days. The median sale price for homes in Cudjoe Key, FL over the last 12 months is $899,000, down 35% from the median home sale price over the previous 12 months.
In Cudjoe Key, there are currently 32 houses for sale, offering an array of options for potential buyers. With houses priced between $350,000 to $3,750,000, there's a range to accomodate every budget. As of December, 2025 the median home price in Cudjoe Key is $1,175,000, while the average sale price is $2,195,666, offering insights into the local housing market. On average, houses spend 110 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Cudjoe Key, FL and find the perfect place to call home.