Osceola County neighborhoods, Kissimmee to St. Cloud. Know what matters before you buy.

Osceola is two markets wearing one county name. West of I-4 toward the parks sits the short-term-rental economy: zoned vacation corridors around Four Corners and the 192 strip where the same floor plan can be a primary residence, a long-term rental or a licensed STR depending on the plat, and where buyers routinely misread which one they are purchasing. East, St. Cloud rides the Lake Nona spillover down Narcoossee Road with conventional family subdivisions, while Celebration remains its own Disney-built universe with a fee architecture unlike anything else in Florida.

Our guides are explicit about the single most expensive mistake in this county: tenure. Every page states whether a community allows short-term rental, what the HOA and CDD stack actually totals, and how the toll-road commute math works against the sticker savings versus Orange County.

1,784 community guides, organized by town — the largest towns show their most active communities here, with every community on the town page. Start with the interactive Neighborhood Finder if you'd rather browse the whole map.

Buying? Homes for sale in Kissimmee, FL · Kissimmee condos for sale · Osceola County homes for sale

Thinking of selling in Kissimmee? See what your home would sell for

ZIP codes: Kissimmee ZIP codes

Kissimmee (1028)

See all 1,028 Kissimmee communities → (36 most active shown here)

St. Cloud (385)

See all 385 St. Cloud communities → (36 most active shown here)

Celebration (59)

See all 59 Celebration communities → (36 most active shown here)

Poinciana (9)

Harmony (25)

Davenport (219)

See all 219 Davenport communities → (36 most active shown here)

Reunion (39)

See all 39 Reunion communities → (36 most active shown here)

Champions Gate (14)

Kenansville (6)

Griffis AcresGriffis Acres in Kenansville, FL: 3 homes, built 2020-2020. Live Stellar MLS data and public records.Haf HopHaf Hop in Kenansville, FL: 22 homes built 1957–2025, ~1,188 sq ft, 2 bd/2 ba. Schools, HOA & nearby homes for sale.Lake Marian ParkLake Marian Park in Kenansville, FL: 1 home for sale from $29K. Live Stellar MLS data and public records.Lake Marian ShoresLake Marian Shores in Kenansville, FL: Median sale $222K (2026), 21 homes, built 1985-2011, median 83 days on market.Lake Marion HighlandsLake Marion Highlands in Kenansville, FL: Recent sales median $225K (2025), $220/sq ft, 4 sales since 2024.Turkey HollowTurkey Hollow in Kenansville, FL: 7 homes built 1999–2023, ~2,084 sq ft, 4 bd/2 ba. Schools, HOA & nearby homes for sale.

Straight answers

Can I buy a short-term rental anywhere in Kissimmee?

No. STR licensing is plat-specific. Communities a street apart can have opposite rules, and lenders price them differently. Every guide in an STR corridor states the rental posture up front and tells you what to verify with the county and the HOA.

Why is Celebration so much more expensive than the rest of Osceola?

Disney-era urbanism, fixed supply and a fee structure that funds it: HOA, enhanced tax district and, in newer phases, additional assessments. The premium is real and so are the carrying costs; our Celebration guides itemize both.

Is St. Cloud a good alternative to Lake Nona?

That is the trade most buyers are actually making: Narcoossee-corridor St. Cloud runs meaningfully cheaper per square foot than Lake Nona proper, paid back in commute time and CDD assessments in the newer master plans. The guides quantify both sides.

Homes for sale now in Osceola County

5,391 live listings in this area, 485 listed in the last 7 days. A selection, newest first:

2489 Bulrush Drive, St Cloud · $381,000 · 4 bd · 1,787 sq ft · Courtesy of EXP REALTY LLC
3113 Songbird Cir, St Cloud · $379,500 · 3 bd · 1,876 sq ft · Courtesy of RESORT REALTY GROUP LTD INC
1869 Kings Point Boulevard, Kissimmee · $350,000 · 3 bd · 1,704 sq ft · Courtesy of COLDWELL BANKER REALTY
248 Cheshire Court, Kissimmee · $289,900 · 4 bd · 1,695 sq ft · Courtesy of TRANSCEND REALTY
169 Birmingham Drive, Kissimmee · $237,000 · 3 bd · 1,481 sq ft · Courtesy of LANDCRAFT REALTY GROUP, LLC
1037 Blackwolf Run Road, Davenport · $435,000 · 4 bd · 2,333 sq ft · Courtesy of BRIGHT TRUST REALTY LLC
9254 Sommerset Hills Drive, Davenport · $695,000 · 9 bd · 4,356 sq ft · Courtesy of REMAX SUNSTATE REALTY
388 Ocean Course Avenue, Davenport · $340,000 · 4 bd · 1,914 sq ft · Courtesy of WEMERT GROUP REALTY LLC
1176 Challenge Drive, Davenport · $449,900 · 5 bd · 2,167 sq ft · Courtesy of EXP REALTY LLC
1861 Nice CT, Kissimmee · $550,000 · 7 bd · 3,281 sq ft · Courtesy of EXP REALTY LLC
209 Westmoreland Circle, Kissimmee · $370,000 · 3 bd · 1,581 sq ft · Courtesy of 1ST CLASS REAL -T- TREATMENT
225 Celebration Place #427, Celebration · $214,887 · 2 bd · 1,206 sq ft · Courtesy of BLUE KEY PROPERTY MANAGEMENT
4375 Silver Creek Street, Kissimmee · $599,900 · 5 bd · 3,092 sq ft · Courtesy of REAL BROKER, LLC
4472 Monado Drive, Kissimmee · $800,000 · 8 bd · 2,872 sq ft · Courtesy of WRA BUSINESS & REAL ESTATE
901 Anchorage Lane, Kissimmee · $414,900 · 3 bd · 2,375 sq ft · Courtesy of ENTERA REALTY LLC
760 Drop Shot Drive, Davenport · $699,000 · 8 bd · 4,370 sq ft · Courtesy of DTB FLORIDA REALTY, INC.
986 Splash Shot Place, Davenport · $405,000 · 4 bd · 1,914 sq ft · Courtesy of RELATED GENERAL REALTY, LLC.
406 Bridgewater Court, Kissimmee · $349,900 · 3 bd · 1,876 sq ft · Courtesy of TRIPLE S REALTY
1601 Groveline Road, St Cloud · $445,000 · 4 bd · 1,839 sq ft · Courtesy of LPT REALTY, LLC
1856 Lattice Way, St Cloud · $536,990 · 4 bd · 2,557 sq ft · Courtesy of RISEWELL HOMES FLORIDA LLC
418 Chesapeake Drive, St Cloud · $339,360 · 3 bd · 1,730 sq ft · Courtesy of CAMBRIDGE REALTY OF CENTRAL FL
4203 Lugano Court, Kissimmee · $450,000 · 4 bd · 2,237 sq ft · Courtesy of COLDWELL BANKER REALTY
1630 Resolute Street, Celebration · $519,000 · 2 bd · 1,782 sq ft · Courtesy of STANICA REALTY GROUP
1158 Drop Lane, Davenport · $694,900 · 10 bd · 4,370 sq ft · Courtesy of ANTS REALTY LLC

Just listed, updated hourly: New in Central & West Florida

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.