Wingrove Estates
Well-maintained 1990s neighborhood with large oak trees and YMCA proximity.
Live the MaxLife.
$750K
Median Price
$550K – $1M
79
Homes
$100–$170
Monthly HOA
1988
Established
Dr. Phillips Elementary (A-rated)
School Zone
Background
A brief history
Wingrove Estates was developed between 1988 and 1994 on Conroy-Windermere Road in the northern portion of Dr. Phillips. The 79-home community was designed with emphasis on mature oak tree preservation and pedestrian-friendly sidewalk infrastructure. The developer emphasized the non-gated, family-oriented positioning with an attractive but non-restrictive entrance. The neighborhood sits in close proximity to the Dr. P. Phillips YMCA Family Center, making it appealing to families with young children. Development completed in the early-to-mid 1990s and has maintained strong resident stability.
The feel
What it's like to live here
Wingrove Estates feels like a well-maintained, quiet Orlando neighborhood defined by large oak trees. Homes are primarily traditional architecture, built 1988–1994, typically 2,296–3,241 square feet with 3, 4, and 5 bedrooms. Homes sit on standard Orlando lots (0.3–0.5 acre) with spacious yards and mature oak coverage. Many feature screened lanais, pools, or recently updated kitchens. The entrance is attractive and noticeable but non-gated. The vibe is family-friendly with strong community identity and low turnover.
The details
What to expect
Architecture & Lots
1990s traditional architecture. Homes 2,296–3,241 square feet, 3–5 bedrooms. Standard Orlando lot sizes (0.3–0.5 acre) with large mature oak trees. Many feature screened lanais or pools. Family-room floor plans typical of the era.
Lifestyle & Amenities
Non-gated but well-maintained community with mandatory HOA. Distinctive mature oak tree canopy throughout. Walking distance to Dr. P. Phillips YMCA Family Center (one of Central Florida's highest-rated YMCAs). Sidewalk infrastructure. Nearby shopping and dining on Conroy-Windermere Road.
HOA Rules & Fees
Mandatory HOA — $100–$170/month. Architectural review required for exterior changes and landscaping. Short-term rentals typically prohibited. Non-gated community — open street access. Mature tree-preservation policies common.
Schools
Zoned for Dr. Phillips Elementary (A-rated), Southwest Middle School, and Dr. Phillips High School (VPA Magnet). Private option: The First Academy ~20 minutes.
Access & Commute
Located on Conroy-Windermere Road corridor. I-4 access via Sand Lake Road (2–3 miles). 15 minutes to Disney, 12 to Universal, 25 to MCO. Walking distance to Dr. P. Phillips YMCA. Downtown Orlando 25–30 minutes off-peak.
Community
Amenities
- Distinctive mature oak tree canopy
- Walking distance to Dr. P. Phillips YMCA Family Center
- Sidewalk infrastructure throughout
- Well-maintained community with strong resident tenure
- Convenient access to Conroy-Windermere Road shopping and dining
- Attractive but non-gated entrance
Know Before You Buy
HOA rules worth knowing
- Mandatory HOA — $100–$170/month
- Architectural review required for exterior changes
- Tree-preservation policies for mature oaks
- Short-term rentals typically prohibited
- Non-gated community — open street access
Education
School assignments
- Dr. Phillips Elementary (A-rated)
- Southwest Middle School
- Dr. Phillips High School (VPA Magnet)
- The First Academy (private, ~20 min)
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Wingrove Estates homes trade in the $550K–$1M range, with most sales clustering $700K–$900K. Three-to-four-bedroom homes run $550K–$750K; five-bedroom homes with pools reach $900K–$1M. Price per square foot averages $295. The proximity to the YMCA and reputation for community maintenance command modest premiums. Days-on-market typically 55–75 days, steady for the Dr. Phillips area.
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Information on this page is compiled from public records, MLS data, community associations, and broker observation. Price ranges, HOA fees, school assignments, and community amenities change — verify all details with MaxLife Realty and the relevant community association before making a purchase decision. Ryan Solberg, Broker, License #BK3354351. MaxLife Realty, 321.373.3536.