Homes, values and local insight for Winter Garden, Orange County, Florida. Typical home value $567,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Winter Garden is known for its brick-lined historic downtown on Plant Street, where the paved West Orange Trail runs right down the middle of the street. Locals and visitors come for the Saturday Winter Garden Farmers Market, the restored 1935 Garden Theatre and a busy food and brewery scene. The city sits on the south shore of Lake Apopka, about 30 minutes west of Orlando.
Settlers arrived by the 1850s to farm citrus and vegetables in the muck land along Lake Apopka. Winter Garden was established in 1903 and incorporated as a city in 1908, with A.B. Newton as its first mayor, and the Edgewater Hotel opened in 1927 to host bass fishing tourists. Downtown was listed on the National Register of Historic Places in 1996 after residents rallied to save the commercial district. Winter Garden mixes a small historic downtown with fast-growing new neighborhoods to the south in Horizon West. Weekends center on the farmers market, the trail and outdoor dining along Plant Street.
The brick commercial core along Plant and Main Streets, rebuilt in brick after early fires and listed on the National Register in 1996. Walkable to the trail, theatre, restaurants and farmers market. ( source )
Older homes bounded by Plant, Boyd, Tilden and Central Streets, with 76 historic buildings in Bungalow/Craftsman, Prairie School and Colonial Revival styles. Listed on the National Register on August 1, 1996. ( source )
A large master-planned area adopted by Orange County in 1995, bordered by Winter Garden to the north and Windermere to the east, near Walt Disney World. Built as a town center plus villages such as Bridgewater, Lakeside, Hickory Nut, Ovation and Seidel, set in greenbelts. Mostly newer construction. ( source )
A small historic community on the west side of Winter Garden along County Road 545, named for citrus pioneer Luther F. Tilden. The old South Lake Apopka Citrus Growers Association packinghouse on Tildenville School Road still stands and houses small businesses. ( source )
A small town just west of Winter Garden, incorporated in 1887, with a Historic Town Hall from 1912. The West Orange Trail passes through its downtown and the Oakland Nature Preserve sits on its Lake Apopka shore. ( source )
Three-course prix fixe dinner with optional wine pairings at the Chef's Table, or small plates and craft cocktails in The Tasting Room. Opened in 2008 inside the historic Edgewater Hotel. ( source )
Modern American · 146 West Plant StreetSeasonal, contemporary dishes built on locally handcrafted products. ( source )
Mexican grill and bar · 129 West Plant StreetFresh Mex tacos and burritos, plus a rooftop bar with a view of downtown. ( source )
Barbecue · Plant Street Market, 426 West Plant StreetBrisket and pulled pork inside Plant Street Market. ( source )
Pizza · Plant Street Market, 426 West Plant StreetCoal-fired artisan pizza, wings and sandwiches. ( source )
Oyster bar · Plant Street Market, 426 West Plant StreetFresh oysters at a counter inside Plant Street Market. ( source )
Latin seafood · Plant Street Market, 426 West Plant StreetCeviche and fresh guacamole made to order. ( source )
Coffeehouse and roastery · 146 West Plant StreetLocal roaster serving espresso drinks, tea, panini and desserts, with a cafe downtown and its roastery inside Plant Street Market. ( source )
Craft brewery and taproom inside Plant Street Market with a pet-friendly patio, live entertainment and brewery tours. ( source )
Indoor market with about 20 food and artisan vendors under one roof, open seven days a week, attached to the Crooked Can brewery. ( source )
Piano bar with handcrafted martinis, house-made bitters, Open Mic Night and Jazz Jam, and live music upstairs in Pilars Loft. Next door to the Garden Theatre. ( source )
The city's outdoor living room with swings, a mosaic-tiled fountain, the Clock Tower and a gazebo stage for Fridays on the Plaza live music. ( source )
Open-air pavilion at 104 South Lakeview Avenue with picnic tables for downtown takeout. Home of the Saturday farmers market. ( source )
Large open-air shopping center at 3041 Daniels Road with more than 80 stores and restaurants, built on a former citrus grove. ( source )
Gourmet food shop with Spanish olives, French mustards, preserves, cured sausages and handmade pastas. ( source )
Independent, owner-operated jeweler downtown for more than 20 years, focused on custom design and repairs. ( source )
Running and walking shoe store at 56 West Plant Street known for its fit process. ( source )
Full-service bike shop with sales, repairs and a rental station for riding the West Orange Trail. ( source )
Over 140 spices, hand-mixed seasonings, teas and olive oils at 4 East Plant Street. ( source )
A 14-foot wide paved rail trail that runs down the middle of Plant Street and connects about 34 miles of trail through Oakland and Apopka. Winter Garden Station trailhead is at 455 East Plant Street. ( source )
in townLakefront park on Lake Apopka named for the first mayor, with a boardwalk, boat ramp, playground, gazebo and sunset views. ( source )
in townA 200-acre conservation park on the shore of Johns Lake with nature trails, a playground under live oaks, ranch relics and a canoe and kayak launch. Opened in phases starting in 2018. ( source )
about 3 miles150-acre preserve with the Healthy West Orange Boardwalk out to Lake Apopka, upland trails and an environmental education center. Trails open sunrise to sunset. ( source )
about 15 to 20 milesAn 11-mile one-way drive through restored wetlands on Lake Apopka's north shore, open Fridays, weekends and federal holidays. 377 bird species have been recorded on the property. ( source )
about 15 milesNearest state park, with three lakes, 20 miles of unpaved multi-use trails, cabins on Dixie Lake, camping and paddling. ( source )
City-owned 295-seat historic theatre, opened in 1935, with art deco details and Mediterranean Revival style. Hosts plays, musicals, concerts and the Flix movie series. ( source )
Rotating exhibits on West Orange County history in the 1923 brick railroad depot at One North Main Street. Free admission. ( source )
Free museum in a former Tavares and Gulf depot built in 1913, with model trains and a large dining car china collection. ( source )
Year-round Saturday market, 8 am to 1 pm, at the Downtown Pavilion with 100+ vendors. Running since 2008 and accepts EBT/SNAP. ( source )
Historic downtown hotel from the 1920s bass fishing era, now run as a bed and breakfast style inn on its second and third floors. ( source )
Free live music at Centennial Plaza. ( source )
OctoberSix nights of Halloween projection shows on the front of City Hall. ( source )
Late NovemberHoliday shopping kickoff with decorated streets, live music and local shop deals. ( source )
Early DecemberLit and decorated golf carts roll through downtown. ( source )
Early DecemberOpen-air holiday market at the Downtown Pavilion with vendor booths, live entertainment and downtown holiday trolleys. ( source )
Dillard Street Elementary, Tildenville Elementary, Maxey Elementary, Whispering Oak Elementary, Lake Whitney Elementary, Hamlin Elementary
MiddleLakeview Middle, SunRidge Middle, Bridgewater Middle, Water Spring Middle
HighWest Orange High, Horizon High
PrivateFoundation Academy
Listed for reference, not ranked. Confirm school zoning for any address with the district. ( source )
SR 50, SR 429 (Western Beltway), SR 408 and Florida's Turnpike
AirportsOrlando International Airport (MCO), roughly 35 to 45 minutes depending on traffic
Downtown Orlando: about 30 min Orlando area theme parks: about 30 min Oakland: about 5 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 Winter Garden is worth $567,000, 41% above the Orange County typical value of $401,000 and 51% above the Florida typical value of $375,000.
Zillow Home Value Index for Winter Garden, August 2026. The middle of the market for single family homes and condos.
Home values in Winter Garden moved +26.2% over five years and +86.7% over ten.
Median gross rent in Winter Garden. Useful for investors running rental numbers.
Share of occupied homes in Winter Garden lived in by the owner.
A newer housing stock means fewer surprises at inspection.
Median household income in Winter Garden.
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 Winter Garden home of $567,000:
Ryan and Megan price Winter Garden homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
Typical value $569,000 · 3,796 residents
Area guide →Typical value $707,000 · 3,223 residents
Area guide →Typical value $413,000 · 51,269 residents
Area guide →Typical value $683,000 · 1,811 residents
Area guide →Typical value $429,000 · 50,851 residents
Area guide →19,675 residents
Area guide →See the full Orange County real estate guide or the Florida real estate guide.
The Zillow Home Value Index for Winter Garden was $567,000 in August 2026, -1.0% over the past year.
Winter Garden is in Orange County, Florida.
About 48,771 people as of the 2024 Census Bureau estimate, up from 47,400 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.
69% of occupied homes in Winter Garden 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 Winter Garden is worth $570,875 as of August 2026 in ZIP code 34787. Values moved -0.9% 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 |
|---|---|---|---|---|---|
| 34787 | $570,875 | -0.9% | +26.2% | $580,000 | 45 |
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.
