Windermere Heights

The Windermere Height community in Dr. Phillips is known for its great location, large home sites. The community comprises of 69 home sites set on large lots up to 2 acres in size. The community offers of 3 to 6 bedroom homes most built in the 80’s and 90’s. Windermere Heights is one of the few subdivisions in Dr. Phillips with no homeowners association. The community is within walking distance to Palm Lake Elementary, and Olympia High School. Windermere Heights is a peaceful, private community with convenient access to shopping, restaurants, and downtown Orlando.

Windermere Heights 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
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
New
1300 S Dewey Street, EUSTIS

$260,000

1300 S Dewey Street, EUSTIS

3 Beds 2 Baths 1,300 SqFt Residential MLS® # O6448218
New
2071 Dixie Belle Drive 2071m, ORLANDO

$169,900

2071 Dixie Belle Drive 2071m, ORLANDO

3 Beds 2 Baths 1,192 SqFt Residential MLS® # O6448576
New
2218 Grand Cayman Court 1335, KISSIMMEE

$197,500

2218 Grand Cayman Court 1335, KISSIMMEE

2 Beds 2 Baths 1,026 SqFt Residential MLS® # S5159189
1756 Tanglewood Drive, KISSIMMEE

$599,900

1756 Tanglewood Drive, KISSIMMEE

5 Beds 3 Baths 2,532 SqFt Residential Income MLS® # O6415364
358 Fulton Street, DAYTONA BEACH

$85,000

358 Fulton Street, DAYTONA BEACH

0 Beds 0 Baths 0 SqFt Land MLS® # FC310658
1756 Tanglewood Drive, KISSIMMEE

$599,900

1756 Tanglewood Drive, KISSIMMEE

5 Beds 3 Baths 2,532 SqFt Residential MLS® # O6414176
New
166 Catfish Street, HAINES CITY

$499,900

166 Catfish Street, HAINES CITY

3 Beds 2 Baths 1,867 SqFt Residential MLS® # L4965609
New
910 Big Tree Road 7-2, SOUTH DAYTONA

$159,999

910 Big Tree Road 7-2, SOUTH DAYTONA

3 Beds 2 Baths 1,442 SqFt Residential MLS® # O6448376
1111 Long Oak Way, SANFORD

$249,900

1111 Long Oak Way, SANFORD

3 Beds 3 Baths 1,409 SqFt Residential MLS® # O6427597
New
2307 Butterfly Palm Way 302, KISSIMMEE

$225,000

2307 Butterfly Palm Way 302, KISSIMMEE

2 Beds 2 Baths 1,022 SqFt Residential MLS® # S5158942
New
3607 S Crystal Lake Drive, ORLANDO

$389,000

3607 S Crystal Lake Drive, ORLANDO

3 Beds 2 Baths 1,118 SqFt Residential MLS® # G5118753
New Open House
6549 State Road 33, CLERMONT

$799,900

6549 State Road 33, CLERMONT

3 Beds 2 Baths 1,878 SqFt Residential
Fri, Oct 9th, 2026 @ 11am - 2pm
MLS® # S5158854
New
9932 Earlston Street, ORLANDO

$415,000

9932 Earlston Street, ORLANDO

4 Beds 2 Baths 1,578 SqFt Residential MLS® # O6448505
New
3603 Lismore Drive, LAKELAND

$389,000

3603 Lismore Drive, LAKELAND

4 Beds 2 Baths 1,636 SqFt Residential MLS® # P4940112

Sold Homes in Windermere Heights Dr. Phillips

Sold Windermere Heights Real Estate Sold Dr Phillips Real Estate

Windermere Heights Real Estate Market Statistics

Average Price $0
Lowest Price $0
Highest Price $0
Total Listings 0
Avg. Price/SQFT $0

Property Types (active listings)

Dr. Phillips Communities

Windermere Heights Community Information

Location: Dr Phillips Blvd & Oakland Place, South of Conroy Windermere Road
Number of Homesites: 69
Year Built: 1985 - Vacant Lots
Square Feet: 2,367 - 4,000+
HOA Fee: None
Community Amenities: None

The Dr. Phillips community of Windermere Heights is located within excellent proximity to highly rated Orange County Schools, as well as shopping, dining, grocery stores, parks and recreation, and Orlando area hospitals.

Orange County Public Schools

  • Palm Lake Elementary:  Grades: PreK - 5 Distance: .6 miles
  • Chain of Lakes Middle School:  Grades: 6 - 8 Distance: 1.3 miles
  • Olympia High School: Grades: 9 - 12  Distance: 2 miles

Dining and Shopping

  • Shopping Center with Grocery Store – Distance: .4 miles
  • Restaurant Row - Distance: 2.2 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ’s Wholesale Club – Distance: 4.7 miles
  • Winter Garden Village Retail Shopping Center with Super Target - Distance: 11 miles
  • Downtown Orlando – Distance 10 miles

Parks and Recreation

  • Dr. P. Phillips Community Park, Sporting Fields, Fountain Water Park – Distance:  6.5 miles
  • Lake Down Public Access Boat Ramp – Distance: 2.3 miles
  • Dr. P. Phillips YMCA Family Center – Distance  1.9 miles

Hospitals

  • Health Central Hospital – Distance: 7.4 miles
  • Dr. P. Phillips Hospital – Distance: 4.9 miles

*Distances are approximately measured from the Windermere Heights community entrance.

Orlando - Windermere Home

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