Winderwood
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
Palm Lake Elementary School
School Zone
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Background
A brief history
Winderwood was developed starting in 1998 as an established residential community in Windermere. Approximately 250 homes were platted across multiple phases, with construction progressing through the early 2010s. The community emphasizes traditional architecture and community amenities. 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 community built around reasonable pricing and neighborhood cohesion rather than 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. The community has strong HOA governance and maintains consistent standards. It fits buyers 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
Friendly neighborhood. Strong sense of community. Long-term residents mixed with newcomers. 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
School assignment follows the street address, so check each home in OCPS Find My School before you write an offer. Value proposition is strong: a Windermere location for 30–40% less than luxury gated communities. Good access to 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
- Palm Lake Elementary School
- Chain of Lakes Middle School
- Dr. Phillips High School
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: buyers get a Windermere zip code and HOA protections for 30–40% less than comparable-sized homes in Keene's Pointe or Isleworth.
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Homes available in Winderwood
2 homes currently listed in Winderwood.
$700,000
4425 Winderwood Cir
Orlando, FL 32835
4 bd · 3 ba · 2,335 sqft
Winderwood
This property is under contract. Contact us for backup offer opportunities.
MLS ID #O6438658, KELLER WILLIAMS ADVANTAGE III.
Listing provided by Stellar MLS
$649,900
4507 Winderwood Cir
Orlando, FL 32835
3 bd · 2 ba · 2,201 sqft
Winderwood
This property is under contract. Contact us for backup offer opportunities.
MLS ID #O6429389, KEENE'S POINTE REALTY.
Listing provided by Stellar MLS
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of October 5, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA