Winderlakes

Winderlakes, offering Dr. Phillips real estate, is nestled in a gorgeous pocket filled with moss-covered trees, scenic wooded areas, and sparkling lakes. This single-family home community is close to the excitement and convenience of the Dr. Phillips area, located off Conroy Windermere Road and Winderlakes Drive. This hidden gem features a variety of home styles, ranging from approximately 1,580 square feet to 4,100+ square feet, with 2 to 5 bedrooms, 2 to 3 baths, and 2- to 3-car garages. Several homes here boast fireplaces and sizable 1/2-acre lots surrounded by trees. In addition, many homeowners have added private outdoor pools.

Winderlakes Homes for Sale

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2015 Summerfield Road, WINTER PARK

$1,250,000

2015 Summerfield Road, WINTER PARK

4 Beds 4 Baths 3,024 SqFt Residential 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
226 Pine Street, ORLANDO

$420,000

226 Pine Street, ORLANDO

3 Beds 2 Baths 1,603 SqFt Residential 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
New Open House
381 Augustine Court, OVIEDO

$600,000

381 Augustine Court, OVIEDO

4 Beds 3 Baths 2,725 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 2pm
MLS® # O6448356

Sold Homes in Winderlakes Dr. Phillips

Real Estate Statistics

Average Price $574K
Lowest Price $569K
Highest Price $579K
Total Listings 2
Avg. Days On Market 47
Avg. Price/SQFT $273
List to Sell Price Percentage 97 %

Property Types (active listings)

Winderlakes residents enjoy excellent proximity to a variety of outdoor attractions. For instance, just over a mile away are two popular parks—Shadow Bay Park and Bill Frederick Park—that offer a variety of activities. Shadow Bay Park features walking trails, basketball courts, and a full-service tennis center with multiple tennis courts. At the same time, Bill Frederick Park offers fishing, boating, disc golf, and pavilions with barbecue grills. In addition, Rose Park provides an excellent spot for the little ones, with its playground, sports field, and walking trail. Golfers will have their choice of several local courses, including Orange Tree Golf Club and MetroWest Golf Club, both within a few miles. Winderlakes also offers residents convenient access to the area’s top theme parks, including Universal Studios Florida, SeaWorld Orlando, Walt Disney World, and ICON Park.

Multiple shopping and dining options are within a short drive from the community. A Publix Grocery Store and a Neighborhood Walmart are within 2 miles, with numerous shopping centers, a Walmart Supercenter, and the Mall at Millennia a short drive away. The renowned “Restaurant Row,” featuring a variety of restaurants representing various cultures and cuisines, is also close by.

Winderlakes is conveniently located close to top-rated schools and Valencia College and offers easy access to major roadways, including I-4, the Florida Turnpike, and SR-535. Thus, it is perfect for those seeking peaceful surroundings and urban amenities.

Call us today to find out more about Winderlakes.

Winderlakes Community Information

  • Location: Conroy Windermere Road and Winderlakes Drive
  • Year Built: 1979 - 1989
  • Number of Homesites: 200 single-family homes
  • HOA: Yes

Orange County Public Schools

  • Windy Ridge K-8 School: Grades K - 8th Distance: .5 miles
  • Chain of Lakes Middle School: Grades 6th - 8th Distance: 1 miles
  • Olympia High School: Grades 9th - 12th Distance: 2 miles

Dining and Shopping

  • Grand Oaks Village – Distance: 1 mile
  • Shoppes of Winder Oaks – Distance: 1.5 miles
  • Shoppes of Windermere – Distance: 2 miles
  • The Grove with Grocery Store – Distance: 2 miles
  • Kirkman Oaks Shopping Center – Distance: 2.5 miles
  • MetroWest Village – Distance: 2.5 miles
  • Shoppes of Cypress Creek – Distance: 3 miles
  • The Marketplace at Dr. Phillips with Grocery Store – Distance: 4 miles
  • Plaza Venezia with Publix Grocery Store – Distance: 4 miles
  • Dellagio Town Center – Distance: 4 miles
  • Universal Plaza – Distance: 4 miles
  • Phillips Crossing – Distance: 4.5 miles
  • Bayhill Plaza – Distance: 5 miles
  • Orlando Crossings – Distance: 5 miles
  • The Mall at Millennia – Distance: 5 miles
  • Downtown Orlando – Distance - Distance: 10 miles

Parks and Recreation

  • Bill Frederick Park – Distance: 2 miles
  • Shadow Bay Park – Distance: 2 miles
  • Orange Tree Golf Club – Distance: 3 miles
  • Dr. Phillips YMCA – Distance: 3 miles
  • Fernwood Park – Distance: 4 miles
  • Palmer Park – Distance: 4 miles
  • Eagle Nest Park – Distance: 4.5 miles
  • Rose Place Park – Distance: 5 miles
  • Windermere Recreation Area – Distance: 5 miles
  • Lake Street Park – Distance: 5 miles
  • R.D. Keene Park – Distance: 5.5 miles
  • Shingle Creek Trail – Distance: 6 miles
  • Dr. Phillips Community Park – Distance: 8 miles
  • Kia Center – Distance: 9 miles

Theme Parks

  • Walt Disney World Resort – Distance: 9.5 miles
  • Universal Studios – Distance: 4 miles
  • SeaWorld – Distance: 8 miles

Hospital

  • Orlando Health Dr P Phillips Hospital – Distance: 6 miles
  • Orlando Health – Health Central Hospital – Distance: 6 miles

*Distances are approximately measured from the entrance to the Winderlakes subdivision.

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