Florida Keys neighborhoods, Key Largo to Key West. Know what matters before you buy.
The Florida Keys are a single 113-mile island chain along US-1 in Monroe County, and the market splits by mile marker: Key West and its old-town/condo core at the end of the road, the Upper Keys resort and second-home corridor from Key Largo through Islamorada, and the quieter Middle and Lower Keys around Marathon and Big Pine. Nearly everything trades on water access, elevation, and whether short-term rental is allowed.
What decides a Keys purchase is the vacation-rental rules, which vary sharply by city and by the county's ROGO building-permit system, plus wind and flood insurance and real hurricane and surge exposure on low coral-rock lots. The guides state the rental posture, the flood-zone and elevation reality, and whether a dock or canal access conveys.
103 community guides, organized by town below. Start with the interactive Neighborhood Finder if you'd rather browse the whole map.
Key West (21)
Key Largo (27)
Marathon (27)
Big Pine Key (9)
Cudjoe Key (2)
Summerland Key (3)
Duck Key (3)
Plantation Key (3)
Lower Matecumbe (2)
Sugarloaf Key (1)
Little Torch Key (3)
Key Colony (2)
Straight answers
Can I short-term rental a home in the Florida Keys?
It depends heavily on the jurisdiction - Key West, Marathon, Islamorada, and unincorporated Monroe each have their own vacation-rental rules, and many areas require a minimum 28-day rental. Confirm the exact rental license and zoning for the specific address before you buy for income.
Why are building permits (ROGO) a factor in the Keys?
Monroe County's Rate of Growth Ordinance strictly caps new building permits, so a buildable vacant lot or an existing legal dwelling carries real scarcity value. Confirm the permit and legal-unit status before offering on land or a teardown.
How bad is insurance and flood risk in the Keys?
Most of the chain is low-elevation coral rock in high-velocity wind and flood zones, so wind, flood, and elevation certificates drive both insurance cost and financing. Confirm the flood zone, base flood elevation, and any prior claims before you write an offer.
Homes for sale now in Florida Keys
1,370 live listings in this area, 145 listed in the last 7 days. A selection, newest first:
- 8 Grassy Road, Key Largo · $750,000 · 1 bd · Courtesy of Lifestyle International Realty
- 1133 W Ocean Drive #6, Key Colony · $899,000 · 3 bd · Courtesy of Ocean Sotheby's International
- 30371 Warbler Lane, Big Pine Key · $780,000 · 2 bd · Courtesy of Coldwell Banker Schmitt Lower Keys (KW)
- 589 Pirates Road, Little Torch Key · $2,299,000 · 3 bd · Courtesy of Coldwell Banker Schmitt Real Estate Co
- 341 9Th Street, Key Colony · $1,380,000 · 3 bd · Courtesy of Coldwell Banker Schmitt Real Estate Co.
- 3821 Eagle Avenue, Key West · $2,199,000 · 3 bd · Courtesy of Preferred Properties (KW)
- 1104 Packer Street, Key West · $2,249,000 · 4 bd · Courtesy of Vested Palm Real Estate and Home Services
- 84961 Old Highway #28, Windley Key · $375,000 · 1 bd · Courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
- 22939 Sharp Lane, Cudjoe Key · $1,885,000 · 3 bd · Courtesy of Coldwell Banker Schmitt Real Estate Co
- 27821 Leeward Road, Little Torch Key · $1,200,000 · 2 bd · Courtesy of KeyIsle Realty
- 325 Calusa Street ## 86, Key Largo · $345,000 · 2 bd · Courtesy of RE/MAX All Keys Real Estate
- 828 W Ocean Drive, Key Colony · $1,115,000 · 3 bd · Courtesy of Coldwell Banker Schmitt Real Estate Co.
- 301 Sombrero Beach Road #101, Marathon · $415,000 · 1 bd · Courtesy of Coldwell Banker Schmitt Real Estate Co.
- 108 Bar None Road, Forsyth · $350,000 · 4 bd ยท 2,432 sq ft · Courtesy of PrimePoint Ventures
- 341 3rd Street, Key Colony · $789,000 · 2 bd · Courtesy of Expert Realty LLC (HQ)
- 12399 Overseas Highway ## 10, Marathon · $1,095,000 · 3 bd · Courtesy of LoKation Real Estate
- 7218 Simran Lane #Hawks Cay Resort, Duck Key · $1,200,000 · 3 bd · Courtesy of Florida Keys Realty Group LLC
- 260 15Th Circle, Key Colony · $18,000,000 · 6 bd · Courtesy of Trustpoint Realty, LLC
- 6099 Overseas Highway #Lot 60W, Marathon · $289,000 · 1 bd · Courtesy of Coldwell Banker Schmitt Real Estate Co.
- 29324 Coconut Palm Drive, Big Pine Key · $709,000 · 3 bd · Courtesy of Century 21 All Keys Inc (KW)
- 87455 Old Highway #Apt 234, Plantation Key · $399,000 · 2 bd · Courtesy of LoKation Real Estate
- 733-743 Trinidad Lane, Little Torch Key · $2,999,000 · 3 bd · Courtesy of eXp Realty LLC
- 133 Dorsett Drive, Marathon · $895,000 · 2 bd · Courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
- 29558 Ranger Avenue, Big Pine Key · $1,700,000 · 3 bd · Courtesy of Meyer and Boumerhi Realty LLC
Just listed, updated hourly: New in Florida Keys · New in Georgia
Live MLS listings, refreshed hourly; listings held by other brokerages are marked with the listing broker. Information deemed reliable but not guaranteed. Equal Housing Opportunity.