Best Neighborhoods to Buy a Home in Kissimmee

How to read this list

Zillow's Kissimmee list mixes three kinds of places: neighborhoods inside the City of Kissimmee, unincorporated Osceola County communities with Kissimmee addresses, such as Buena Ventura Lakes, and villages of Celebration, the planned town originally developed by Disney. North Village, South Village, East Village and Artisan Park are Celebration villages, and Celebration Village and West Village appear to be part of the same town. Zillow's boundaries don't always match the names locals or HOAs use.

Each figure below is Zillow's typical value for all homes in the area, with the one-year and five-year change. A neighborhood with mostly townhomes will read lower than one with mostly large houses, even if the quality is similar. Treat the numbers as a price band, then look at actual listings.

One more caution. A one-year change of two or three percent in a small neighborhood can come from a handful of sales, and Zillow smooths its index to reduce that noise but cannot remove it. The five-year figure is usually a better read on how a neighborhood has held value, and the one-year figure is better as a hint about current negotiating room.

Under $300,000: the entry band

• Shadow Bay: $210,203, down 7.0% in a year and 2.2% over five years.
• Osceola Park Estates: $290,840, up 1.6% in a year and 30.4% over five, the strongest five-year gain on the list.
• Orange Gardens: $296,340, nearly flat at minus 0.3% and up 22.7% over five years.

These three show how different two cheap neighborhoods can be. Shadow Bay's value has gone sideways for five years and fell hard this year, which can point to a housing type under pressure, and Kissimmee's condo index is down 6.9% this year. Osceola Park Estates has gained steadily. For a buyer under $300,000, check the age of the homes and roofs, the HOA or condo association's finances, and the flood zone before deciding the low price is a bargain.

$320,000 to $360,000: the middle of the market

Most of Zillow's Kissimmee list sits close to the city's typical value. In this band:

• Estancia $322,793 (1y -2.3%, 5y 21.0%)
• Bermuda Bay $327,110 (1y -1.6%, 5y 26.1%)
• Oak Hollow $333,009 (1y -3.0%, 5y 22.4%)
• Mill Run $333,979 (1y -0.9%, 5y 25.8%)
• Buena Ventura Lakes $336,294 (1y -2.4%, no five-year figure)
• Lakeside $337,990 (1y -2.1%, 5y 24.3%)
• Westwood Forest $345,041 (1y -1.4%, 5y 26.9%)
• Oak Run $346,887 (1y -2.0%, 5y 22.6%)
• Bermuda Estates $354,581 (1y -1.4%, 5y 19.7%)
• Creekside Estates $356,627 (1y -2.1%, 5y 20.3%)

Mill Run, Westwood Forest and Bermuda Bay combine small one-year dips with five-year gains above 25%. In a band this tight, differences between subdivisions come down to the HOA, the CDD if any, the age of the homes and the drive to work. I'd shortlist two or three here and compare total monthly cost, not list price.

$365,000 to $435,000: more house, softer year

• Country Creek Estates $367,033 (1y -1.4%, 5y 20.2%)
• Eagle Pointe $368,371 (1y -4.9%, 5y 18.1%)
• Stonefield $375,087 (1y -3.3%, 5y 7.0%)
• Renee Terrace $385,956 (1y -1.4%, 5y 20.2%)
• Cypress Reserve $387,877 (1y -2.7%, 5y 14.2%)
• Eagle's Reserve $395,510 (1y -3.1%, 5y 21.0%)
• The Oaks $398,761 (1y -3.3%, 5y 14.0%)
• Weston Reserve $430,254 (1y -1.7%, 5y 20.4%)
• Cumbrian Lakes $432,771 (1y -2.9%, 5y 25.3%)

This band lines up with Zillow's typical four-bedroom in Kissimmee, about $396,436. One-year changes are a bit weaker here than in the middle band, with Eagle Pointe down 4.9%. Stonefield's five-year gain of 7.0% is well below the city's 17.8%, which can reflect newer construction that sold at full price recently and has not appreciated since. Newer communities also tend to carry CDD assessments, so add that to the comparison.

Above $440,000: Celebration and the top of the list

• Celebration Village $451,777 (1y +1.1%, 5y 15.5%)
• North Village $523,787 (1y +0.9%, 5y 2.1%)
• South Village $527,458 (1y +4.1%, 5y 9.3%)
• Artisan Park $543,400 (1y +2.6%, 5y 10.9%)
• West Village $573,284 (1y -0.4%)
• Spring Lake $641,750 (1y +1.6%, 5y 26.3%)
• East Village $805,410 (1y +3.1%, 5y 35.5%)

Most of the neighborhoods that rose in value over the past year are in this group, while nearly everything below it fell. The Celebration villages, apart from East Village, show modest five-year growth after starting from high prices. West Village's five-year figure on Zillow is an outlier that likely reflects a change in the data rather than the market, so I've left it out. Celebration has its own community association structure and fees, separate from the city, and that belongs in your monthly cost.

What to check in any Kissimmee neighborhood

• Jurisdiction: city, county or Celebration. It changes taxes and rules.
• Flood zone: the area is full of lakes, creeks and wetlands. Look up each address.
• Insurance: roof age, wind mitigation and, for older homes, a 4-point inspection.
• HOA and CDD: get both amounts and the HOA rules in writing.
• Homestead: the assessed value resets at purchase. A permanent resident can claim up to $51,411 off assessed value in 2026.
• Owner occupancy: some communities near the tourist corridor have many part-time owners. Ask the HOA.

If two or three of these bands fit your budget, a shortlist that lines up the best-value subdivisions in each by total monthly cost is the practical next step.