Homes, values and local insight for Windermere, Orange County, Florida. Typical home value $707,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Windermere is a small lakeside town on the Butler Chain of Lakes in west Orange County. It is known for its small downtown with unpaved side streets, its 1922 Town Hall, and the luxury golf and lakefront estates around it, including Isleworth.
Englishman John Dawe platted the community in 1887 and named it after Lake Windermere in England's Lake District. The Town of Windermere was incorporated on February 2, 1925. The Colonial Revival Town Hall at 520 Main Street was built in 1922 and added to the National Register of Historic Places in 1994. The town has about 3,000 residents and a quiet, small-town pace built around the lakes and Main Street. The wider Windermere mailing area mixes historic lake homes, gated golf estates and newer master-planned neighborhoods in Horizon West.
The original town grid on an isthmus between Lake Down and Lake Butler. Most side streets are unpaved dirt roads, and homes range from older lake houses to custom builds near Main Street. ( source )
A 600-acre private golf club community on the Butler Chain of Lakes with an 18-hole course originally designed by Arnold Palmer. Estate homes, many with lake or golf views. It sits in unincorporated Orange County, outside town limits. ( source )
An established upscale lakeside subdivision that voted to annex into the Town of Windermere in 2007, with over 90% of residents approving by mail ballot. ( source )
A newer master-planned community in the Horizon West area with a Windermere mailing address, near the Bridgewater Crossings shops and cafes. ( source )
Newer Horizon West neighborhoods around Lakeside Village Park on Village Lake Road, which opened in 2018, close to Winter Garden Vineland Road shopping. ( source )
Opened in 2010 in a 1950s saw-tooth roof building. Known for Bananas Foster French toast, fried chicken with cheddar grits and passion fruit mimosas. Pet-friendly patio. ( source )
Asian street food · 9100 Conroy Windermere Road, Windermere areaShareable plates and craft cocktails. The Basil Fried Rice is a customer favorite. Has a private dining room. ( source )
Cafe, breakfast and lunch · 13790 Bridgewater Crossings Blvd, Horizon West (Windermere mailing address)Opened December 2023. Single-origin Guatemalan coffee, smoothies, pastries and salads. Popular with remote workers. ( source )
American cafe and bar · 1236 Hempel Avenue, GothaServing since 1995 from a spot in tiny Gotha. Locals go for The Waldorf and the Bourbon Chicken Bite. ( source )
Fine dining Italian · 7600 Dr. Phillips Blvd, Dr. Phillips (Orlando)Open since 1984 on Restaurant Row. Handmade pasta, a 16-ounce bone-in veal chop, and a rose for every woman at the end of the meal. ( source )
Turkish, Mediterranean · 7600 Dr. Phillips Blvd, Dr. Phillips (Orlando)Turkish breads, hot and cold appetizers, pastries and entrees in the Marketplace at Dr. Phillips on Restaurant Row. ( source )
Modern Japanese, sushi · 7705 Turkey Lake Road, Dr. Phillips (Orlando)James Beard-nominated. Chef Henry Moso serves omakase and kaiseki-style dinners. ( source )
Farm-to-table fine dining · 99 West Plant Street, downtown Winter GardenThree-course prix fixe menu with wine pairings, plus a casual Tasting Room for small plates and cocktails. ( source )
The public boat ramp on Lake Isleworth gives access to the Butler Chain. Parking holds 49 trailers, and the gate closes when full until 2 p.m. on busy days. ( source )
Coffee shop in the Summerport community with a large shaded patio, free WiFi, beer and wine. Pet-friendly. Open 7 a.m. to 5 p.m. ( source )
Craft brewery inside Plant Street Market with core and seasonal beers, brewery tours and indoor and outdoor seating. ( source )
More than two dozen restaurants and bars along Sand Lake Road near International Drive, from steakhouses to wine bars. ( source )
Over 100 vendors, live music and a nearby splash fountain every Saturday at the Downtown Pavilion in Winter Garden. ( source )
Neighborhood center at 4750 The Grove Drive anchored by Publix and LA Fitness Signature Club, with local boutiques and restaurants. ( source )
Large retail destination with national and local shops. ( source )
Indoor market in downtown Winter Garden with about 20 vendors selling food and handmade goods, anchored by Crooked Can Brewing. ( source )
Independent boutiques and salons in the restored storefronts of downtown Winter Garden, established in 1903. ( source )
438-acre Orange County preserve with hiking trails and the Vera Carter Environmental Center. Part of the Great Florida Birding and Wildlife Trail. No bikes or pets. ( source )
about 4 miles9-acre county park on Village Lake Road in Horizon West, opened in 2018. ( source )
about 8 miles215-acre county park that opened in 2010. A playground, restroom and pavilion opened in February 2026. ( source )
about 8 miles22 miles of paved trail through Killarney, Oakland, Winter Garden and Apopka. Good for biking, running and skating. ( source )
about 20 miles11-mile one-way drive through restored marsh with 377 bird species recorded. Open to cars Friday through Sunday and federal holidays. ( source )
about 20 milesNearest state park. Lakes Louisa, Hammond and Dixie, 20 miles of unpaved trails, cabins, camping and paddling. ( source )
Colonial Revival building from 1922, once the Windermere Women's Club, listed on the National Register of Historic Places in 1994. Its courtyard is the heart of downtown. ( source )
Local history museum at One North Main Street, run by the Winter Garden Heritage Foundation. Open Tuesday through Saturday. ( source )
Railroad artifacts and dining car collections at 101 South Boyd Street. ( source )
Home of the Winter Garden Art Association with rotating exhibits and art classes at 127 S. Boyd Street. ( source )
Cultural center at 21 East Plant Street operated by the Winter Garden Heritage Foundation. ( source )
Town tradition with hayrides and a costume parade at Town Hall. ( source )
Annual; date posted on the town websiteTown road race through the lakeside streets of Windermere. ( source )
Annual; date posted on the town websiteTown-hosted festival for residents and their pets. ( source )
Recurring; schedule posted on the town websiteTown-run food truck evenings and a local farmers market downtown. ( source )
Every Saturday, 8 a.m. to 1 p.m.Award-winning market since 2008 with over 100 vendors at the Downtown Pavilion, 104 South Lakeview Avenue. ( source )
Windermere Elementary, Keene's Crossing Elementary
MiddleGotha Middle, Bridgewater Middle
HighOlympia High, Windermere High, Dr. Phillips High
PrivateWindermere Preparatory School
Listed for reference, not ranked. Confirm school zoning for any address with the district. ( source )
Main Street, Conroy-Windermere Road, Chase Road, Winter Garden-Vineland Road (CR 535), Apopka-Vineland Road, SR 429 and I-4
AirportsOrlando International Airport (MCO): about 30 min
Dr. Phillips / Restaurant Row: about 15 min Downtown Winter Garden: about 20 min Walt Disney World: about 20 min Downtown Orlando: about 25 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 Windermere is worth $707,000, 77% above the Orange County typical value of $401,000 and 88% above the Florida typical value of $375,000.
Zillow Home Value Index for Windermere, August 2026. The middle of the market for single family homes and condos.
Home values in Windermere moved +33.7% over five years and +83.4% over ten.
Median gross rent in Windermere. Useful for investors running rental numbers.
Share of occupied homes in Windermere lived in by the owner.
A newer housing stock means fewer surprises at inspection.
Median household income in Windermere.
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 Windermere home of $707,000:
Ryan and Megan price Windermere homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
Typical value $567,000 · 48,771 residents
Area guide →12,458 residents
Area guide →Typical value $413,000 · 51,269 residents
Area guide →Typical value $569,000 · 3,796 residents
Area guide →23 residents
Area guide →Typical value $6,286,000 · 25 residents
Area guide →See the full Orange County real estate guide or the Florida real estate guide.
The Zillow Home Value Index for Windermere was $707,000 in August 2026, +0.1% over the past year.
Windermere is in Orange County, Florida.
About 3,223 people as of the 2024 Census Bureau estimate, up from 3,029 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.
95% of occupied homes in Windermere 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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Get coming-soon homes, pocket listings and price drops in Windermere, FL before they hit the big home search sites.
The typical home in Windermere is worth $702,439 as of August 2026 in ZIP code 34786. Values moved +0.0% 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 |
|---|---|---|---|---|---|
| 34786 | $702,439 | +0.0% | +33.3% |
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.
