Winwood
Affordable early-1980s ranch neighborhood with excellent school access.
Live the MaxLife.
$300K
Median Price
$200K – $400K
40
Homes
$60–$110
Monthly HOA
1985
Established
Dr. Phillips Elementary (A-rated)
School Zone
Background
A brief history
Winwood was developed between 1985 and 1988 as a small, modest-scale neighborhood off Conroy-Windermere Road in northern Dr. Phillips. The 40-home community was designed with entry-level pricing in mind, targeting first-time homebuyers and investors. Homes are primarily ranch-style single-family, platted on standard-size lots. Development completed by the late 1980s and has maintained steady occupancy with a mix of owner-occupants and investment-rental properties. The community remains one of the most affordably-priced neighborhoods in the Dr. Phillips ZIP code.
The feel
What it's like to live here
Winwood feels like a classic 1980s budget neighborhood. Tree-lined streets, though not with the mature canopy of older communities. Homes are primarily ranch architecture, 2,083–2,853 square feet, with 3–4 bedrooms and 2-car garages. The neighborhood is non-gated with mandatory HOA oversight. The vibe is utilitarian and practical — residents appreciate the proximity to schools and shopping more than neighborhood aesthetics. Many units are rental investments rather than owner-occupied.
The details
What to expect
Architecture & Lots
1980s ranch architecture. Homes 2,083–2,853 square feet, 3–4 bedrooms, 2-car garages. Standard Orlando lot sizes. Tree-lined streets but less mature canopy than older neighborhoods. Many require cosmetic or structural updates (roofing, plumbing, electrical).
Lifestyle & Amenities
Non-gated neighborhood with mandatory HOA. Tree-lined streets. Located off Conroy-Windermere Road with easy I-4 and Florida Turnpike access. Close to Dr. Phillips Elementary and YMCA. Minimal community amenities — focus on practical, affordable living.
HOA Rules & Fees
Mandatory HOA — $60–$110/month (among the lowest in Dr. Phillips). Architectural review for major changes. Short-term rentals permitted in many cases. Non-gated community — open street access. Minimal amenity maintenance costs.
Schools
Zoned for Dr. Phillips Elementary (A-rated), Southwest Middle School, and Dr. Phillips High School (VPA Magnet). Private option: The First Academy ~25 minutes.
Access & Commute
Located off Conroy-Windermere Road. I-4 and Florida Turnpike easily accessible (1 mile). 20 minutes to Disney, 15 to Universal, 30 to MCO. Downtown Orlando 30–35 minutes off-peak.
Community
Amenities
- Tree-lined streets
- Close proximity to Dr. Phillips Elementary and YMCA
- Easy I-4 and Florida Turnpike access
- Minimal amenity costs (low HOA)
- Excellent value for entry-level Dr. Phillips buyers
- Mixed owner-occupant and investor community
Know Before You Buy
HOA rules worth knowing
- Mandatory HOA — $60–$110/month (lowest in Dr. Phillips)
- Architectural review for major changes
- Short-term rentals permitted in many cases
- Non-gated community — open street access
- Pet policies apply
Education
School assignments
- Dr. Phillips Elementary (A-rated)
- Southwest Middle School
- Dr. Phillips High School (VPA Magnet)
- The First Academy (private, ~25 min)
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Winwood homes trade in the $200K–$400K range, with most sales $250K–$350K. This is among the most affordable entry points into the Dr. Phillips 32819 ZIP code. Price per square foot averages $225, well below the neighborhood median, reflecting the modest home sizes and 1980s construction. Days-on-market typically 50–70 days. The affordability and proximity to I-4 and Florida Turnpike make it attractive to investors and first-time buyers accepting renovation needs.
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Recent sales in Dr. Phillips
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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.