Moving to Kissimmee, Florida: The 2026 Data Guide

By Jon Brooks, Co-Founder, Momentum Realty · Updated September 27, 2026

As of 2026-09-27, the median home sold in Kissimmee, Florida over the last 12 months went for $380,000 (2,677 closings across 783 communities in Momentum’s MLS record), about $195 per square foot for a median 1,873-sq-ft home built around 2005. Homes currently listed have been on the market a median of 55 days, and with 3,118 active listings against that sales pace the city is carrying roughly 14.0 months of supply. Sellers have been getting about 96% of their original asking price. That median is 5% below the median across Momentum’s Florida and Georgia coverage.

Kissimmee is the largest short-term-rental market in the state and one of its busiest new-construction markets, and both of those facts shape the numbers on this page. The median is right on the statewide line, but the inventory picture is not: months of supply here run well above most Florida cities because a large share of the listings are investor-owned homes near the attractions.

If you are relocating to live here rather than to rent a home out, that inventory is your leverage.

What your budget buys in Kissimmee

Three price points from 2,076 recent Kissimmee closings in our record, each showing what actually closed within 10% of that price:

• Around $280,000: the typical sale in this band was a 3-bed, 2-bath home of about 1,552 sq ft, built around 2005 (274 sales).
• Around $380,000: the typical sale in this band was a 4-bed, 2-bath home of about 1,837 sq ft, built around 2006 (467 sales).
• Around $455,000: the typical sale in this band was a 4-bed, 3-bath home of about 2,220 sq ft, built around 2007 (379 sales).

At each price band the typical home is newer than in the older Florida cities, because so much of Kissimmee was built in the last twenty years. The lower band is townhomes and smaller single-family homes in the eastern subdivisions; the upper band is dominated by vacation-zoned communities where the price includes a pool and furnishings. Make sure any home you compare is zoned the way you intend to use it, because the two markets are priced differently.

The real monthly cost of owning in Kissimmee

Take the median $380,000 home with 20% down at today’s 7.03% 30-year rate: principal and interest run about $2,029/month. Osceola County’s typical total millage is 15.23 mills, so after the $50,000 homestead exemption the property tax is roughly $5,027/year ($419/month) for a new owner — the seller’s capped bill on the listing will be lower and is not your number. Citizens Property Insurance’s average premium in Osceola County is about $1,735/year; private-market quotes vary with roof age and wind mitigation. 86% of current Kissimmee listings carry an HOA, with a median of $286/month where one applies. All in, budget on the order of $2,878/month to own the median Kissimmee home including a typical HOA.

HOA coverage is nearly universal here and the fees are meaningful, partly because so many communities carry amenity centers built for the rental market. Osceola County's millage is moderate, and insurance is in the middle of the state's range. The number relocating buyers miss most often is the CDD, which is common in the newer master-planned communities and lands on the tax bill.

For the full worksheet — taxes by scenario, the homestead exemption, and how the Save Our Homes cap works after year one — see the Osceola County property tax guide and our home insurance by county map.

Where people are buying: Kissimmee’s most active communities

The communities with the most closings in the last 12 months, with each one’s median sale and how long its current listings have been on the market. Every name links to that community’s own guide with live listings.

The table mixes vacation communities such as Windsor at Westside and Storey Lake with residential ones such as Bellalago, Tohoqua and Knightsbridge. The medians look similar; the use is not. A primary-residence buyer should focus on the residential communities, where the neighbors are owner-occupants and the HOA rules assume it.

Kissimmee by ZIP code

Sales and medians by ZIP over the same 12 months: 34746 (559 sales, median $360,000), 34747 (507 sales, median $445,000), 34744 (314 sales, median $392,000), 34758 (299 sales, median $325,650), 34741 (216 sales, median $308,750), 34743 (131 sales, median $355,000).

What’s for sale: property types, new construction, and age of homes

Of the last 12 months of sales, 68% were single-family homes, 21% townhomes or villas, and 10% condos. New construction accounted for 21% of closings, led by Knightsbridge 50S, Evergreen Park, The Townhomes at Westview, Tohoqua, Westview. The housing stock skews mixed: 34% of homes sold were built in 2015 or later and 6% before 1980.

A quarter of closings were new construction, and the builders here are competing hard on incentives. That keeps resale pricing honest and gives a relocating buyer a real choice between a new build with a warranty and a lightly-used resale with the landscaping already grown in. Either way, the sale-to-list figure says sellers are not getting full ask, so there is room to negotiate.

Getting around from Kissimmee

Measured from the center of Kissimmee’s recent sales: Orlando International Airport (MCO) is about 13 miles; Downtown Orlando is about 17 miles; Lakeland is about 35 miles; Melbourne is about 54 miles. Distances are straight-line; drive times depend on the corridor and time of day.

Kissimmee's location south of Orlando puts the airport closer than downtown, which is unusual and useful for frequent travelers. The commute into Orlando runs on the Turnpike, I-4 and the toll roads, and I-4 congestion is the honest reason to check your drive time at rush hour before you choose a side of the city.

Schools, taxes, and insurance: where to verify

School assignments change; check the Osceola County school grades page for the district’s current grades, and confirm zoning for a specific address directly with the district. Property tax figures on this page use Osceola County’s typical millage of 15.23; municipal and special-district millage varies inside the county. Insurance uses Citizens’ Osceola County average of $1,735/year; a wind-mitigation inspection and roof age can move a private quote a long way in either direction.

Kissimmee: the case for and against

For a buyer who wants a newer home near Orlando with room to negotiate, Kissimmee is one of the better values in Central Florida right now. Just be deliberate about the rental-versus-residential line, because it determines your neighbors, your HOA, and your resale market.

Your Kissimmee relocation toolkit

• Homes for sale in Kissimmee right now
• Cost of living in Kissimmee
• Best neighborhoods in Kissimmee
• New construction in Kissimmee
• Find an agent in Kissimmee
• Kissimmee ZIP codes with prices
• Search every Kissimmee community

Common questions about moving to Kissimmee

Sales figures are Momentum Realty’s MLS record of closings in Kissimmee communities over the trailing 12 months (community snapshots as of their last refresh; price-band examples from the most recent closings on file); tax and insurance figures are Osceola County data. Estimates, not guarantees; verify before relying on them. General relocation guidance, not financial advice. Equal Housing Opportunity.