Shadow Lawn

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. 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.

Shadow Lawn Homes for Sale

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New
Timberlane Road, LAKE WALES

$215,000

Timberlane Road, LAKE WALES

0 Beds 0 Baths 0 SqFt Land MLS® # O6448344
New
Timberlane Road, LAKE WALES

$269,000

Timberlane Road, LAKE WALES

0 Beds 0 Baths 0 SqFt Land MLS® # O6448343
New Open House
20 Walden, ORMOND BEACH

$349,900

20 Walden, ORMOND BEACH

3 Beds 2 Baths 1,874 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 3pm
MLS® # V4951731
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447200
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447201
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447198
Pending
1624 Sterns Drive, LEESBURG

$285,000

1624 Sterns Drive, LEESBURG

4 Beds 2 Baths 2,936 SqFt Residential MLS® # O6425853
New
3110 Emerald Acres Lane, SANFORD

$374,500

3110 Emerald Acres Lane, SANFORD

3 Beds 3 Baths 1,682 SqFt Residential MLS® # S5159186
New
5714 Cattle Ranch Drive, ST CLOUD

$3,095

5714 Cattle Ranch Drive, ST CLOUD

4 Beds 4 Baths 3,058 SqFt Residential MLS® # O6448300
1211 Nixonton Street, DELTONA

$440,000

1211 Nixonton Street, DELTONA

3 Beds 3 Baths 2,208 SqFt Residential MLS® # V4951068
New
140 Bombay Avenue, WINTER SPRINGS

$355,000

140 Bombay Avenue, WINTER SPRINGS

3 Beds 2 Baths 1,373 SqFt Residential MLS® # O6448262
New
31744 Boadwater Ave, LEESBURG

$369,900

31744 Boadwater Ave, LEESBURG

4 Beds 3 Baths 2,626 SqFt Residential MLS® # O6447594
New
5381 Maddie Drive, HAINES CITY

$399,900

5381 Maddie Drive, HAINES CITY

5 Beds 3 Baths 3,011 SqFt Residential MLS® # O6446669
New Open House
1249 Waterwitch Cove Circle, ORLANDO

$874,900

1249 Waterwitch Cove Circle, ORLANDO

3 Beds 3 Baths 2,715 SqFt Residential
Sat, Oct 10th, 2026 @ 1pm - 4pm
MLS® # O6446291
New
1881 Red Canyon Drive, KISSIMMEE

$310,000

1881 Red Canyon Drive, KISSIMMEE

3 Beds 3 Baths 1,624 SqFt Residential MLS® # O6448530

Sold Homes in Shadow Lawn Winter Garden

Shadow Lawn Real Estate Market Statistics

Average Price $0
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Total Listings 0
Avg. Price/SQFT $0
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Property Types (active listings)

Winter Garden Communities


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
HOA: No
Amount of space: 600-2,200+ Square feet
Orlando International Airport - Distance: 26 miles

Orange County Schools

  • Maxey Elementary School - Distance: 0.5 mile
  • Lakeview Middle School - Distance: 2 miles
  • West Orange High School - Distance: 2 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

Hospitals

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

*Distances are approximately measured from the Shadow Lawn.

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