Play Street Museum
A tiny town built for young children in Winter Garden, with a doctor's office, fire station, pet rescue and make-believe ice cream.
12107 Stoneybrook West Pkwy, STE 104, Winter Garden, FL 34787
407 FYI · Winter Park · Winter Park History Museum
407 FYI · A Venue PageMuseums & landmarks · Museum · $ · Winter Park
The Write-Up
The Winter Park History Museum tells the town's story from inside its historic railroad depot, a small, charming space run with obvious care. Changing exhibits, including displays of vintage Winter Park postcards, pack local history into a quick stop guests call surprisingly meaningful. It also anchors a free self-guided walking tour of historic sites around town.
200 W New England Ave, Winter Park, FL 32789
Museums & landmarks · Museum
$
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District Story
A park built for the winter, drawn on paper in 1881, and still legible in every street you walk today.
Similar Feel
Matched by vibe, not by neighborhood: the places across Greater Orlando closest in spirit to Winter Park History Museum.
A tiny town built for young children in Winter Garden, with a doctor's office, fire station, pet rescue and make-believe ice cream.
12107 Stoneybrook West Pkwy, STE 104, Winter Garden, FL 34787

Running since 1938, a pontoon ride from the end of Morse Boulevard through the chain of lakes and narrow, tree-shaded canals.
312 E Morse Blvd, Winter Park, FL 32789
A storybook Spanish revival farmhouse on Park Avenue, romantic and intimate, the kind of historic home guests say they could happily live in.
656 N Park Ave, Winter Park, FL 32789

A sculptor's historic home paired with serene, lakeside sculpture gardens in Winter Park.
633 Osceola Ave, Winter Park, FL 32789
Winter Park's wilder, shadier green space, peaceful and a little untamed.
1300 S Denning Dr, Winter Park, FL 32789
A wine-country room transplanted to Winter Park, with wines on tap by the glass, carafe or bottle and a greenhouse patio that glows after dark.
110 S Orlando Ave Ste 12, Winter Park, FL 32789
Keep Going
Other places in Winter Park, Local Picks first, then the closest to Winter Park History Museum.

A glamorous Greek agora on Park Avenue, sophisticated and high-energy from the moment you sit down.
290 S Park Ave, Winter Park, FL 32789

Park Avenue's neighborhood bar, warm and laid back, with boutique wines, craft beers and cocktails built on Winter Park Distillery spirits.
136 S Park Ave, Winter Park, FL 32789
Italian the Park Avenue way: rustic yet upscale, exposed brick and warm light, house-made pastas and wood-fired pizzas.
Prato, 124 N Park Ave, Winter Park, FL 32789

Park Avenue's breakfast room is chill and charming, cozy and bustling in equal measure.
Briarpatch Restaurant, 252 N Park Ave, Winter Park, FL 32789-3814
Handcrafted chocolate in the European tradition on Park Avenue since 1983, and the cocoa scent reaches the sidewalk.
300 S Park Ave, Winter Park, FL 32789

Wine tasting without the intimidation: load a Tasting Card and pour your own tastes, from a sip to a full glass, off a wall of wines.
270 S Park Ave, Winter Park, FL 32789