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Shadow Lawn Winter Garden Real Estate

Shadow Lawn is a charming neighborhood with Winter Garden real estate dating back to 1925, making it an ideal location for those seeking to live in the heart of historic downtown Winter Garden within moments of shopping, dining, and the West Orange Trail.

Shadow Lawn Homes for Sale

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The charming homes in Shadow Lawn mainly were constructed between 1939 to 1953, which gives the area so much character. Bungalows and Ranch-style homes range from 988 to 2,200+ square feet and feature 2-3 bedrooms and 1-3 baths. Some homes also include separate in-law suites. Many of the homes in Shadow Lawn have been updated with new roofs, interiors, and energy-efficient features. The neighborhood's quaint vibe resonates in the charisma of houses that boast unique features, such as entryways with mud rooms, screened-in lanais, and gorgeous backyards with mature citrus trees.

Shadow Lawn offers the perfect opportunity to live just a few short blocks from the historic downtown Winter Garden. Tree-lined brick streets and the welcoming vibe of neighbors gathering at the weekend farmers market, shopping at local boutiques, or dining al fresco lend way to the ideal Florida lifestyle. Nearby, the West Orange Trail features 22 paved miles of trails, a butterfly garden, access to Lake Apopka, and the outpost. Big box retailers, chain restaurants, and grocery stores head to Winter Garden Village or Stoneybrook West Village, just a short drive from Shadow Lawn. Winter Garden has attracted many homebuyers for the wonderful lifestyle that it offers. There's always something to do, from the area's best theme parks to Central Florida's championship golf courses. Commuting to the Orlando International Airport, downtown Orlando, and the many other points of interest is a breeze thanks to proximity to the 429, Florida Turnpike, and State Road 50.

Whether looking for an investment property or a place to call home, Shadow Lawn is a great place to consider for an Orlando real estate purchase.

Shadow Lawn Community Information

Location: E. Maple St. (North), S. Dillard St. (West), Summer St. & Winter St. (East), E. Story Rd. (South)
No. of Homesites: 144
Year(s) Built: 1939-1953
Amount of space: 600-2,200+ Square feet
Orlando International Airport - Distance: 26 miles

Dining and Shopping

  • Grocery Store (Publix at West Point Commons) - Distance: 1 mile
  • Winter Garden Village-Distance: 3 miles
  • Stoneybrook West Village-Distance: 5 miles
  • Downtown Winter Garden-Distance: 1 mile
  • Restaurant Row - Distance: 16 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 14 Miles
  • Downtown Orlando - Distance: 16 miles

Parks and Recreation

  • Walt Disney World Resort-Distance:19 miles
  • Universal Orlando Resort-Distance: 15 miles
  • West Orange Trail - Distance: 5 miles
  • Newton Park (Lakefront park, boat launch, covered pavilions, fishing pier)- Distance: 1 mile
  • Tidenville Park - Distance: 3 miles
  • Johns Lake (Boat Ramp) - Distance: 6 miles
  • Stoneybrook West Golf Club - Distance: 5 miles
  • Golden Bear Golf Club - Distance: 10 miles
  • New Smyrna Beach -Distance: 68 miles


  • Dillard Street Elementary School - Distance: 1 mile
  • Lakeview Middle - Distance: 2 miles
  • West Orange High School - Distance: 2 miles


  • Orlando Health Central Hospital - Distance: 4 miles
  • Advent Health Winter Garden - Distance: 3 miles

*Distances are approximately measured from the Shadow Lawn.