Winderwood
Family-friendly established neighborhood with traditional architecture and value pricing.
Live the MaxLife.
$1.2M
Median Price
$650K – $2.2M
250
Homes
$180–$380
Monthly HOA
1998
Established
Windermere Elementary or Sunset Park Elementary (zoning dependent)
School Zone
Background
A brief history
Winderwood was developed starting in 1998 as an established family-oriented community in Windermere. Approximately 250 homes were platted across multiple phases, with construction progressing through the early 2010s. The community emphasizes traditional architecture, community amenities, and family-friendly design. Builders during the initial phases included regional and national builders focused on moderately-priced, well-built homes rather than ultra-luxury estates. The community has matured significantly; trees have grown in, and turnover has created a mix of original 1990s homes and recent renovations.
The feel
What it's like to live here
Winderwood is an unpretentious, family-oriented community where residents value good schools, reasonable pricing, and neighborhood cohesion over gating or luxury amenities. Homes are predominantly 2,000–3,500 square feet, traditional in style, sited on 0.4–0.7 acre lots. Streets have mature canopy from 25+ years of growth. Residents recognize each other; kids walk to the pool and playground. The community has strong HOA governance and maintains consistent standards. It attracts young families, retirees looking to downsize from larger estates, and owner-occupants seeking good value in Windermere.
The details
What to expect
Architecture & Lots
Traditional architecture — ranch and 2-story homes, 2,000–3,500 square feet. Lots typically 0.4–0.7 acre. Pitched roofs, attached garages, front porches. Most homes built 1998–2010; quality is solid if dated in some cases. Renovated homes have updated kitchens, bathrooms, and flooring that feel contemporary.
Community Amenities
Community pool and splash pad, playground with age-separated equipment, tennis and basketball courts. Walking paths through the community. Central park area with pavilion. Amenities are modest but well-maintained by HOA. Social events and gatherings organized by residents.
Neighborhood Character
Family-oriented, friendly neighborhood. Strong sense of community. Long-term residents mixed with families new to the area. HOA maintains consistent architectural and landscaping standards. Safe, walkable streets with mature tree canopy.
HOA Rules & Fees
Monthly HOA $180–$380 depending on section and amenity tier. Architectural review required for exterior changes. Landscape maintenance standards enforced. Short-term rentals restricted; 30-day minimum lease standard. Community pool and playground maintained by HOA.
Schools & Value
Zoned for excellent Windermere elementary schools and highly-rated middle and high schools. Value proposition is strong: Windermere location and schools for 30–40% less than luxury gated communities. Good access to all schools and shopping.
Community
Amenities
- Community pool and splash pad
- Playground with age-separated equipment
- Tennis and basketball courts
- Walking paths through the community
- Central park area with pavilion
- Mature oak and palm tree canopy throughout
Know Before You Buy
HOA rules worth knowing
- Monthly HOA $180–$380 depending on section
- Architectural review for exterior changes
- Landscape maintenance standards enforced
- Short-term rentals prohibited or restricted; 30-day minimum lease
- Community pool and playground maintained by HOA
- Consistent architectural and landscaping standards
Education
School assignments
- Windermere Elementary or Sunset Park Elementary (zoning dependent)
- Bridgewater Middle or Gotha Middle (zoning dependent)
- Windermere High or Olympia High (zoning dependent)
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Market trades in the $900K–$1.5M band for homes in good condition. Homes needing renovation trade from $650K–$900K. Newer construction or recently renovated homes (updated kitchens, bathrooms, flooring) trade $1.3M–$2.2M. Days-on-market average 25–40 days for homes priced to comps. The value proposition is strong relative to nearby luxury communities: families get Windermere zip code, good schools, and HOA protections for 30–40% less than comparable-sized homes in Keene's Pointe or Isleworth.
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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.