Homes, values and local insight for Kissimmee, Osceola County, Florida. Typical home value $356,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Kissimmee is the county seat of Osceola County and sits on the shore of Lake Tohopekaliga. It is known for cattle ranching roots, the Silver Spurs Rodeo, a walkable historic downtown along Broadway, and quick access to the Walt Disney World area along US 192.
Kissimmee was incorporated in 1883 after Philadelphia developer Hamilton Disston based his Florida land drainage operations here. W.B. Makinson opened his hardware store on Broadway in 1884, and it ran for 137 years before closing in 2021. The Silver Spurs Rodeo grew out of a gathering of local ranchers in the early 1940s. Kissimmee mixes long-time ranching families, a large Latin community, commuters to Orlando, and vacation-home owners near the parks. Days center on the lakefront, the Broadway cafes, and easy drives to Orlando and the attractions.
The old core along Broadway near the train station and Lake Toho. Older homes, apartments above renovated buildings like the former Makinson Hardware, and a walkable strip of local cafes and bars. ( source )
Gated community with canal access to Lake Toho, boat lifts, and a separately run club with two pools, tennis and basketball courts, playgrounds, and a dog park. Mostly single-family homes. ( source )
Established 1980s community in central Kissimmee with single-family homes, townhomes, and condos. Mature landscaping, parks, and a recreation center. Many sections have no CDD. ( source )
Newer master-planned community on the south side of Kissimmee, building since 2019. Single-family homes from Pulte and Taylor Morrison with a resort pool, splash pad, fitness center, and trails. ( source )
Resort-style community off Osceola Parkway near Disney with single-family homes, townhomes, and condos. Two clubhouses, heated pools, a lazy river, and water slides. Popular with vacation-rental owners. ( source )
Gated resort community about 2 miles from Disney's main entrance. Condos, townhomes, and single-family homes, with a pool, game room, fitness center, and movie theater. HOA dues include cable, internet, and trash. ( source )
Master-planned town founded by Disney in 1994, next door to Kissimmee. Single-family homes, townhomes, and condos on tree-lined, walkable streets with a lakefront downtown. The Celebration Residential Owners Association runs pools, parks, and a year-round event calendar. ( source )
Large, established area south of Kissimmee with mostly single-family homes and a SunRail station for commuting to Orlando. Many sections have low or no HOA dues. ( source )
Owner Big John Glover smokes brisket, ribs, and pulled pork with his own secret recipe. Try the corn nuggets with powdered sugar. ( source )
American · 308 BroadwaySet in the historic Makinson Hardware building. Known for the Kowboy Jake strip steak and the Smoky Kowboy cocktail. ( source )
Cuban cafe · 131 BroadwayFamily-run spot for Cuban sandwiches, media noche, cafe con leche, and tres leches cake. ( source )
Breakfast and coffee · 18 S Orlando Ave, downtownCosta Rican coffee, empanadas, arepas, and breakfast tacos on a shaded patio. ( source )
Pizza · 403 BroadwayHand-tossed New York-style pies with in-house dough, serving downtown since 2008. Daily happy hour 3 to 6 p.m. ( source )
Chicago-style hot dogs · 103 E Dakin AveChicago dogs, Italian beef, and the Mac Dog topped with mac and cheese and bacon. ( source )
Puerto Rican · 112 Broadway (back side)Patio spot for chicharrones de pollo, bistec encebollado, and camarones al ajillo, with live music. ( source )
Dessert · 520 N Main StLiquid nitrogen ice cream made to order, plus cheesesteaks, outdoor seating, and a pet-friendly setup. ( source )
Restaurant at Big Toho Marina with a wraparound deck over Lake Toho. Catfish and gator dishes and a good spot for sunset. ( source )
Bar and grill on Broadway with sushi, burgers, live music, trivia, and pet-friendly outdoor seating. ( source )
Downtown tapas bar with small plates, craft beer, and wine. ( source )
Weekly classic car parade at Old Town on US 192, with bars, rides, and live music along the walkway. ( source )
Downtown market at 421 Broadway featuring local farmers, artisans, and producers. Open weekdays and Saturday. ( source )
Open-air center at 3208 N John Young Pkwy with Kohl's, JCPenney, Books-A-Million, Michaels, and a Regal cinema. ( source )
Entertainment district on W Irlo Bronson Memorial Hwy with retro and novelty shops, restaurants, and rides. ( source )
Simon outlet center on Vineland Ave with 155+ stores including Gucci, Coach, Nike, and Tory Burch. ( source )
Central Florida's largest mall on S Orange Blossom Trail with Macy's, Dillard's, JCPenney, and 250+ shops and restaurants. ( source )
Downtown park on Lake Toho with a lighthouse, Monument of States, paved trails, splash pad, fishing pier, and event lawns. ( source )
in townLargest boat ramp and marina on Lake Tohopekaliga, with slips, a bait shop, and a fishing pier. ( source )
in townSmall lakeside park on Neptune Road with a fishing pier, grills, and a bike trail to Lakefront Park. ( source )
in townShaded park on Babb Road with paved and unpaved trails, kayak rentals, the Shingle Creek Regional Trail, and historic homestead houses. ( source )
15 miles east of Lake WalesState park with an 1876-era cow camp and living history, 13+ miles of trails, and boating on three lakes. Campgrounds closed for renovation as of 2026; day use open. ( source )
Clermont, west of KissimmeeThree lakes for paddling, 7 miles of paved roads and 20 miles of unpaved trails, cabins, and camping in the Green Swamp area. ( source )
about 60 miles east of Orlando140,000-acre refuge beside Kennedy Space Center with Black Point Wildlife Drive and over 1,500 species. ( source )
The Alligator Capital of the World on S Orange Blossom Trail, open 70+ years, with gator shows and the Screamin' Gator Zipline. ( source )
Walkable Americana district on US 192 with rides, shops, bars, and weekly car cruises. ( source )
Park on Florida Plaza Blvd with coasters, multi-level go-kart tracks, and a 300-foot Skycoaster. ( source )
17 authentic and reproduction pioneer buildings run by the Osceola County Historical Society on Babb Road. ( source )
Free museum on W Vine St with dioramas of Osceola County habitats and interactive displays. ( source )
Billed as the largest rodeo east of the Mississippi, held at Silver Spurs Arena at Osceola Heritage Park. ( source )
FebruaryAnnual fair at Osceola Heritage Park with rides, livestock shows, 4-H and FFA contests, and food. ( source )
JulyFree city celebration at Lakefront Park with live music, food trucks, and fireworks over Lake Toho. ( source )
DecemberNighttime holiday parade with lit floats through downtown, plus a holiday festival at City Hall. ( source )
Central Avenue Elementary, Flora Ridge Elementary, Highlands Elementary, Kissimmee Elementary, Mill Creek Elementary, Pleasant Hill Elementary, Thacker Avenue Elementary, Ventura Elementary
MiddleDenn John Middle, Kissimmee Middle, Neptune Middle, Parkway Middle, Horizon Middle
HighOsceola High, Gateway High, Liberty High, Tohopekaliga High, NeoCity Academy, Osceola County School for the Arts
PrivateHeritage Christian School
Listed for reference, not ranked. Confirm school zoning for any address with the district. ( source )
US 192 (Irlo Bronson Memorial Hwy), Florida's Turnpike, US 441 (Orange Blossom Trail), John Young Parkway, Osceola Parkway, I-4 to the west. SunRail stops downtown.
AirportsOrlando International (MCO): about 20 to 25 minutes
Downtown Orlando: about 30 to 36 min Walt Disney World: about 15 to 25 min Universal Orlando: about 25 to 30 minRyan and Megan Winslow, broker owners of Winslow Homes. REALTOR® since 2009, 3,000+ homes sold, broker in FL, MA, CT and RI, U.S. Army Retired.
Call 386-690-5858 Email Ryan and Megan Get pre-approvedResearched and verified 2026-09-28. Businesses change; call ahead.
The typical home in Kissimmee is worth $356,000, 1% below the Osceola County typical value of $359,000 and 5% below the Florida typical value of $375,000.
Zillow Home Value Index for Kissimmee, August 2026. The middle of the market for single family homes and condos.
Home values in Kissimmee moved +19.9% over five years and +90.4% over ten.
Median gross rent in Kissimmee. Useful for investors running rental numbers.
Share of occupied homes in Kissimmee lived in by the owner.
A newer housing stock means fewer surprises at inspection.
Median household income in Kissimmee.
Ryan and Megan are mortgage bankers with The Federal Savings Bank, lending in all 50 states. You get the home and the loan from one team. On a typical Kissimmee home of $356,000:
Ryan and Megan price Kissimmee homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
See the full Osceola County real estate guide or the Florida real estate guide.
The Zillow Home Value Index for Kissimmee was $356,000 in August 2026, -3.2% over the past year.
Kissimmee is in Osceola County, Florida.
About 84,756 people as of the 2024 Census Bureau estimate, up from 79,191 in 2020.
Ryan and Megan Winslow of Winslow Homes have sold over 3,000 homes since 2009 and are licensed in Florida, Massachusetts, Connecticut and Rhode Island. Call or text 386-690-5858.
Apply at www.winslowloan.com. Ryan and Megan are mortgage bankers with The Federal Savings Bank and lend in all 50 states, including FHA, VA and conventional loans.
48% of occupied homes in Kissimmee are owner occupied, based on the 2019 to 2023 American Community Survey.
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.
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The typical home in Kissimmee is worth $380,668 as of August 2026, across 4 ZIP codes ranging from $284,955 in 34741 to $398,281 in 34747. Values moved -2.7% over the last 12 months at the middle ZIP code.
| ZIP | Typical value | 12 months | 5 years | Median sale, Mar to May 2026 | Days on market |
|---|---|---|---|---|---|
| 34741 | $284,955 | -4.1% | +18.7% | $306,500 | 54 |
| 34743 | $338,029 | -2.7% | +25.9% | ||
| 34744 | $380,668 | -2.5% | +21.3% | $401,495 | 44 |
| 34747 | $398,281 | -3.0% | +12.7% |
Sources: Zillow Home Value Index through August 2026 and the Redfin Data Center ZIP code tracker, March to May 2026. Ask Ryan and Megan for a value for your own home.
