Saddlecrest at Windermere

Saddlecrest at Windermere, offering luxury single-family Windermere 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.

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Saddlecrest at Windermere Homes for Sale

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New
39 Chip Court, KISSIMMEE

$309,000

39 Chip Court, KISSIMMEE

4 Beds 2 Baths 1,732 SqFt Residential MLS® # A4708670
Open House
2015 Summerfield Road, WINTER PARK

$1,250,000

2015 Summerfield Road, WINTER PARK

4 Beds 4 Baths 3,024 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 3pm
MLS® # O6418198
New
3811 Eagle Isles Circle, KISSIMMEE

$649,000

3811 Eagle Isles Circle, KISSIMMEE

5 Beds 5 Baths 3,651 SqFt Residential MLS® # S5158740
New Open House
226 Pine Street, ORLANDO

$420,000

226 Pine Street, ORLANDO

3 Beds 2 Baths 1,603 SqFt Residential
Fri, Oct 9th, 2026 @ 11am - 4pm
MLS® # S5159132
New
1848 Everhart Drive, ORLANDO

$525,000

1848 Everhart Drive, ORLANDO

3 Beds 2 Baths 1,683 SqFt Residential MLS® # O6448256
New
5469 Gingham Drive, KISSIMMEE

$441,940

5469 Gingham Drive, KISSIMMEE

4 Beds 3 Baths 2,753 SqFt Residential MLS® # W7890215
New
4149 S Semoran Boulevard 9, ORLANDO

$147,000

4149 S Semoran Boulevard 9, ORLANDO

2 Beds 2 Baths 1,214 SqFt Residential MLS® # G5118805
New
2229 Mango Tree Drive, EDGEWATER

$295,000

2229 Mango Tree Drive, EDGEWATER

3 Beds 2 Baths 1,038 SqFt Residential MLS® # O6448391
New
8844 Cabot Cliffs Drive, DAVENPORT

$580,000

8844 Cabot Cliffs Drive, DAVENPORT

6 Beds 6 Baths 3,339 SqFt Residential MLS® # O6448535
Open House
1233 Parker Road, LAKELAND

$475,000

1233 Parker Road, LAKELAND

4 Beds 2 Baths 2,612 SqFt Residential MLS® # L4962153
New
106 Harbor Way, AUBURNDALE

$327,000

106 Harbor Way, AUBURNDALE

3 Beds 2 Baths 1,427 SqFt Residential MLS® # P4940115
779 E Chapman Road, OVIEDO

$1,500,000

779 E Chapman Road, OVIEDO

5 Beds 5 Baths 5,219 SqFt Residential MLS® # O6426258
Sold
26029 Oakmount Drive, LEESBURG

$330,000

26029 Oakmount Drive, LEESBURG

2 Beds 2 Baths 1,869 SqFt Residential MLS® # J1006016
New
2388 Grand Central Parkway 2, ORLANDO

$205,000

2388 Grand Central Parkway 2, ORLANDO

3 Beds 2 Baths 1,457 SqFt Residential MLS® # O6447903
New
828 N Scott Avenue, LAKELAND

$255,000

828 N Scott Avenue, LAKELAND

3 Beds 2 Baths 1,261 SqFt Residential MLS® # O6448319

Real Estate Statistics

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Avg. Price/SQFT $0

Property Types (active listings)


Saddlecrest at Windermere Floor Plans

Cabris Saddlecrest at Windermere Cabris

4,283 Square Feet / 5 Bedrooms / 4-5 Bathrooms

Cabris Saddlecrest at Windermere Floorplan View Cabris Saddlecrest at Windermere Floor Plan


Varen Saddlecrest at Windermere Varen

5,081 Square Feet / 5 Bedrooms / 5-6 Bathrooms

Varen Saddlecrest at Windermere Floorplan View Varen Saddlecrest at Windermere Floor Plan


Bressols Saddlecrest at Windermere Bressols

5,711 Square Feet / 5-6 Bedrooms / 5-6 Bathrooms

Bressols Saddlecrest at Windermere Floorplan View Bressols Saddlecrest at Windermere Floor Plan


Soudron Saddlecrest at Windermere Soudron

6,072 Square Feet / 5-7 Bedrooms / 4-5 Bathrooms

Soudron Saddlecrest at Windermere Floorplan View Soudron Saddlecrest at Windermere Floor Plan


Montech Saddlecrest at Windermere Montech

6,996 Square Feet / 6-7 Bedrooms / 6-7 Bathrooms

Montech Saddlecrest at Windermere Floorplan View Montech Saddlecrest at Windermere Floor Plan



Saddlecrest at Windermere, offering luxury single-family Windermere homes for sale, is located 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 Jeffrey Funk and The Funk Collection team today to learn more about Saddlecrest.

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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