Saddlecrest at Windermere

Saddlecrest at Windermere, offering luxury single-family Winter Garden homes for sale, is tucked away on the banks of Lake Roberts and surrounded by a conservation area. This intimate community of 41 homes is located off Windermere Road and Walker Pond Road, perfectly positioned in the gateway of Winter Garden and Windermere real estate.

Saddlecrest at Windermere Homes for Sale

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Saddlecrest at Windermere

Winter Garden Communities

Saddlecrest at Windermere, offering luxury single-family Winter Garden homes for sale, is tucked away on the banks of Lake Roberts and surrounded by a conservation area. This intimate community of 41 homes is located off Windermere Road and Walker Pond Road, perfectly positioned at the gateway of Winter Garden and Windermere real estate.

Builder Toll Brothers offers five thoughtfully crafted floor plans in Saddlecrest at Windermere, each designed to embody luxury and functionality. Homes here have 5 to 7 bedrooms, 4 to 7 baths, 3 to 5 garages, and between approximately 4,250 square feet and 7,000 square feet of living space. Every home sits on a spacious half-acre lot, providing ample room for outdoor living. Select properties include premium features, some offering scenic lakefront access on Lake Robert, while others have peaceful pond views or serene conservation views. Highlights include covered porches, dramatic two-story foyers, expansive double-height great rooms, and gourmet kitchens equipped with large center islands, breakfast bars, and oversized walk-in pantries. Saddlecrest redefines upscale living in a community that combines elegance with practicality.

Location is key, and Saddlecrest at Windermere provides easy access to many parks and recreational opportunities. Just a short drive away, for instance, West Orange Park features picnic areas, a dog park, and four full-sized soccer fields. The Windermere Recreation Area offers a playground, beach volleyball court, tennis courts, and a dock with access to Lake Crescent. Additionally, Lake Street Park provides green space, walking paths, and grills. Golf enthusiasts will appreciate the proximity to Stoneybrook West Golf Course, just a few miles from the community.

Residents enjoy convenient access to shopping destinations, including Plantation Grove and the popular Winter Garden Village. Nearby, downtown Windermere is home to a weekly farmers market, and downtown Winter Garden is also close to Saddlecrest. Saddlecrest is also ideally located near major roadways such as FL-429, the Florida Turnpike, FL-50, FL-408, and I-4.

Call the team today to find out more about Saddlecrest.

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Saddlecrest at Windermere Community Information

  • Location: Windermere Road and Walker Pond Road (border of Winter Garden & Windermere)
  • Year Built: 2025
  • Homebuilder: Toll Brothers
  • HOA: yes
  • Number of Homesites: 41 (off Walker Pond Road) 4 (off Windermere Road)

Osceola County Area Schools

  • Lake Whitney Elementary School: Grades K – 5th Distance: 1 mile
  • Sunridge Middle School: Grades 6th - 8th Distance: 7 miles
  • West Orange High School: 9th – 12th Distance: 3 miles

Dining and Shopping

  • Winter Garden Village – Distance: 3.5 miles
  • Publix Super Market at Plantation Grove – Distance: 3.5 miles
  • Shoppes of Winter Garden – Distance: 4 miles
  • Winter Garden Plaza – Distance: 4 miles
  • Shoppes at Windward Cay – Distance: 4 miles
  • Winter Garden Regional Shopping Center – Distance: 5 miles
  • Windermere Village – Distance: 5 miles
  • Cornerstone at Summerport – Distance: 5 miles
  • Walmart Neighborhood Market – Distance: 5 miles
  • Shoppes of Windermere – Distance: 5 miles
  • Downtown Orlando - Distance: 14 miles

Parks and Recreation

  • George Bailey Park – Distance: 1.5 miles
  • West Orange Park–Distance: 2 miles
  • Windermere Recreation Area—Distance: 3 miles
  • Central Park – Distance: 3 miles
  • Palmer Park - Distance: 3 miles
  • Lake Street Park–Distance: 3 miles
  • Braddock Park Winter Garden Soccer – Distance: 3.5 miles
  • Gotha Park – Distance: 3.5 miles
  • Bird Island – Distance: 3.5 miles
  • West Orange Country Club – Distance: 4 miles
  • Stoneybrook West Golf Course–Distance: 5 miles
  • R.D. Keene Park—Distance: 5.5 miles
  • Deputy Scott Pine Community Park – Distance: 6 miles
  • Kia Center – Distance: 15 miles

Theme Parks

  • Walt Disney World - Distance: 11 miles
  • Universal Studios Orlando - Distance: 10 miles
  • Seaworld Orlando - Distance: 13 miles

Hospitals

  • AdventHealth Winter Garden—Distance: 4 miles

*Distances are approximately measured from the Walker Pond Road entrance to the Saddlecrest subdivision.

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