Homes, values and local insight for Cudjoe Key, Monroe County, Florida.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Cudjoe Key is a census-designated place in Monroe County, in the Lower Florida Keys. U.S. 1, the Overseas Highway, crosses the key at about mile markers 20.5 to 23, between Summerland Key and Sugarloaf Key. The highway runs about 20 miles to Key West and 30 miles to Marathon.
A 1772 chart called the island Littleton Island. An 1849 survey pamphlet called it Cudjoe's. In 1959 the Army activated Cudjoe Key Air Force Station to track missiles over the Eglin Gulf Test Range, and the Air Force took over in 1960. By the 1960s the station held a security squadron and about 339 military personnel.
Today the white radar balloon known as Fat Albert floats over the key, a tethered aerostat used for drug interdiction. The CDP covers about 10.5 square miles and about half of that is water, including Cudjoe Bay. Hurricane Irma made a direct hit on Cudjoe Key as a Category 4 storm on Sept. 10, 2017.
A resort community on the southeast side of the island, shown in the aerial photo on the Cudjoe Key Wikipedia page. source
Cuban · 22836 Overseas Hwy, Cudjoe Key
Roadside cafe serving Cuban sandwiches, picadillo, sweet plantains and cafe con leche for breakfast and lunch. Closed Sundays. source
Coffee and breakfast · 22864 Overseas Hwy, Cudjoe Key (about mile marker 24)
Coffee from the cafe's own Colombian farm, plus waffles, breakfast sandwiches and smoothie bowls. Dog-friendly outdoor seating. source
22864 Overseas Hwy, Cudjoe Key (mile marker 24)
A mercantile-style shop with home goods, glassware, local art, fishing shirts and candles. It adjoins Morning Joint. source
About 2,300 acres on Big Pine Key, the main habitat of the Key deer, a small subspecies of the Virginia white-tailed deer. The Lower Keys tourism page lists early morning and early evening as the best viewing times. source
A former railroad sinkhole on Key Deer Boulevard on Big Pine Key, inside the refuge. It has an alligator observation area and a walking trail. source
A coral reef about five miles offshore of Big Pine Key, used by snorkelers and divers. source
A white radar balloon tethered at the old Cudjoe Key Air Force Station site, floating about 10,000 feet above the island. It has been used for drug interdiction since the early 1970s. source
Built in 1929 at mile marker 17 to house bats that were meant to control mosquitoes. The plan did not work. source
Music is played underwater at Looe Key Reef for divers and snorkelers. The Lower Keys Chamber runs it and proceeds support reef protection. source
A Lower Keys flea market on Big Pine Key, listed on the Keys Weekly Lower Keys events page. source
U.S. 1 runs about 20 miles west-southwest to Key West and about 30 miles east to Marathon. Miami is about 136 miles northeast on the same highway.
$990,150 for a single-family home in Monroe County. FHA loans allow 3.5% down with a 580 credit score.
$832,750 for a single-family home. Above that, buyers use a jumbo loan. Megan Winslow structures both.
Owners who live in the home take up to $50,000 off the taxable value, and the Save Our Homes cap limits yearly increases in the assessed value to 3%. File with the Monroe County Property Appraiser by March 1.
Broker owner of Winslow Homes, REALTOR since 2009, U.S. Army Retired. Ryan Winslow lists and sells homes across Cudjoe Key and Monroe County and handles pricing, negotiation and the contract to closing.
Broker owner of Winslow Homes and a Mortgage Banker with The Federal Savings Bank. Megan Winslow helps Cudjoe Key and Monroe County buyers get pre-approved and closes the loan with the same team that negotiates the home.
Megan and Ryan Winslow have worked side by side for 17 years and sold more than 3,000 homes together. One team for the home search, the listing and the mortgage. Call or text 386-690-5858.
What is my home worth? Get pre-approved with Megan Agents: join Winslow Homes
Ryan and Megan price Cudjoe Key homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
See the full Monroe County real estate guide or the Florida real estate guide.
Cudjoe Key is in Monroe County, Florida.
Look for a broker who knows Cudjoe Key sales and can explain the numbers. Ryan and Megan Winslow of Winslow Homes have 17+ years together, more than 3,000 homes sold, and lend in all 50 states with The Federal Savings Bank. Call or text 386-690-5858.
The 2026 FHA limit for a single-family home in Monroe County is $990,150, and the 2026 conventional limit is $832,750. Megan Winslow, a Mortgage Banker with The Federal Savings Bank, can pre-approve you for either.
About 20 miles by U.S. 1, the Overseas Highway. Marathon is about 30 miles the other way and Miami is about 136 miles.
You need a building permit allocation under Monroe County's Rate of Growth Ordinance. Supply is limited and rules are changing, so ask the Monroe County Growth Management Department before you buy a lot.
The Florida Department of Health in Monroe County says central sewer is nearly universal in the Keys and must be used where available. Septic systems are rare and must be Performance Based Treatment Systems.
17 years, over 3,000 homes sold, and one team for the home and the loan. Call or text 386-690-5858.
Sources: U.S. Census Bureau 2024 population estimates and 2019 to 2023 American Community Survey; Zillow Home Value Index, August 2026. Numbers update as new data is released. Talk to Ryan and Megan for current sold prices on your street.
Get coming-soon homes, pocket listings and price drops in Cudjoe Key, FL before they hit the big home search sites.
17+ years together, more than 3,000 homes sold, and the mortgage handled by the same team.
