Windermere City Guide

Historic Downtown Windermere

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)

Isleworth

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)

Butler Bay

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)

Summerport (Horizon West)

A newer master-planned community in the Horizon West area with a Windermere mailing address, near the Bridgewater Crossings shops and cafes. (source)

Lakeside Village area (Horizon West)

Newer Horizon West neighborhoods around Lakeside Village Park on Village Lake Road, which opened in 2018, close to Winter Garden Vineland Road shopping. (source)

Dixie Cream Cafe

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)

Hawkers Asian Street Food

Shareable plates and craft cocktails. The Basil Fried Rice is a customer favorite. Has a private dining room. (source)

Henko Cafe & Bistro

Opened December 2023. Single-origin Guatemalan coffee, smoothies, pastries and salads. Popular with remote workers. (source)

Yellow Dog Eats

Serving since 1995 from a spot in tiny Gotha. Locals go for The Waldorf and the Bourbon Chicken Bite. (source)

Christini's Ristorante Italiano

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)

Bosphorous Turkish Cuisine

Turkish breads, hot and cold appetizers, pastries and entrees in the Marketplace at Dr. Phillips on Restaurant Row. (source)

Kabooki Sushi

James Beard-nominated. Chef Henry Moso serves omakase and kaiseki-style dinners. (source)

Chef's Table at the Edgewater

Three-course prix fixe menu with wine pairings, plus a casual Tasting Room for small plates and cocktails. (source)

Butler Chain of Lakes (R.D. Keene Park boat ramp)

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)

Foxtail Coffee Horizon West

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)

Crooked Can Brewing Company (Winter Garden)

Craft brewery inside Plant Street Market with core and seasonal beers, brewery tours and indoor and outdoor seating. (source)

Restaurant Row (Dr. Phillips)

More than two dozen restaurants and bars along Sand Lake Road near International Drive, from steakhouses to wine bars. (source)

Winter Garden Farmers Market

Over 100 vendors, live music and a nearby splash fountain every Saturday at the Downtown Pavilion in Winter Garden. (source)

The Grove

Neighborhood center at 4750 The Grove Drive anchored by Publix and LA Fitness Signature Club, with local boutiques and restaurants. (source)

Winter Garden Village (Winter Garden)

Large retail destination with national and local shops. (source)

Plant Street Market (Winter Garden)

Indoor market in downtown Winter Garden with about 20 vendors selling food and handmade goods, anchored by Crooked Can Brewing. (source)

Historic Plant Street shops (Winter Garden)

Independent boutiques and salons in the restored storefronts of downtown Winter Garden, established in 1903. (source)

Tibet-Butler Preserve

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)

Lakeside Village Park

9-acre county park on Village Lake Road in Horizon West, opened in 2018. (source)

Horizon West Regional Park (Winter Garden)

215-acre county park that opened in 2010. A playground, restroom and pavilion opened in February 2026. (source)

West Orange Trail (Winter Garden)

22 miles of paved trail through Killarney, Oakland, Winter Garden and Apopka. Good for biking, running and skating. (source)

Lake Apopka Wildlife Drive (Apopka)

11-mile one-way drive through restored marsh with 377 bird species recorded. Open to cars Friday through Sunday and federal holidays. (source)

Lake Louisa State Park (Clermont)

Nearest state park. Lakes Louisa, Hammond and Dixie, 20 miles of unpaved trails, cabins, camping and paddling. (source)

Windermere Town Hall

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)

Winter Garden Heritage Museum (Winter Garden)

Local history museum at One North Main Street, run by the Winter Garden Heritage Foundation. Open Tuesday through Saturday. (source)

Central Florida Railroad Museum (Winter Garden)

Railroad artifacts and dining car collections at 101 South Boyd Street. (source)

SOBO Art Gallery & Studio (Winter Garden)

Home of the Winter Garden Art Association with rotating exhibits and art classes at 127 S. Boyd Street. (source)

Healthy West Orange Heritage and Cultural Center (Winter Garden)

Cultural center at 21 East Plant Street operated by the Winter Garden Heritage Foundation. (source)

Halloween Hayride & Costume Parade

Town tradition with hayrides and a costume parade at Town Hall. (source)

Run Among the Lakes 5K/10K

Town road race through the lakeside streets of Windermere. (source)

Windermere PetFest

Town-hosted festival for residents and their pets. (source)

Windermere Food Truck Nights and Farmers Market

Town-run food truck evenings and a local farmers market downtown. (source)

Winter Garden Farmers Market (Winter Garden)

Award-winning market since 2008 with over 100 vendors at the Downtown Pavilion, 104 South Lakeview Avenue. (source)

Windermere Elementary, Keene's Crossing Elementary

Gotha Middle, Bridgewater Middle

Olympia High, Windermere High, Dr. Phillips High

Windermere Preparatory School

Main Street, Conroy-Windermere Road, Chase Road, Winter Garden-Vineland Road (CR 535), Apopka-Vineland Road, SR 429 and I-4

Orlando International Airport (MCO): about 30 min