Winter Park Pines
Winter Park Pines Living: Local Insights & FAQs
To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.
Where is Winter Park Pines located?
Winter Park Pines is south of Aloma Avenue (SR 426) and west of Semoran Boulevard (SR 436), along streets such as S. Ranger Boulevard, Banchory Road, Cady Way and Scarlet Road. It has Winter Park addresses, but almost all of it is in unincorporated Orange County; a handful of homes on S. Ranger Boulevard and Sandwell Drive are inside City of Winter Park limits.
What types of homes are in Winter Park Pines?
Mostly single-family homes built from 1962 to 1971, according to state parcel records, plus patio homes built from about 1984 to 1995 and a 33-unit condominium built in 1986. Based on MLS listings and sales from the past two years, homes range from about 1,200 to 2,680 square feet with 2 to 5 bedrooms.
How much do homes cost in Winter Park Pines?
Over the past two years (MLS data, October 2026), single-family homes in Winter Park Pines sold for a median of about $548,000, with most between about $417,000 and $775,000. Five sales of smaller duplex-style homes built in the 1980s had a median of about $310,000. For today's listings, see the top of this page.
Is there an HOA in Winter Park Pines?
Winter Park Pines Community Association, Inc. is a membership-based community association. Its website lists annual membership tiers from $60 to $250 or more. The condominium section has its own association, Winter Park Pines Condominium Association, Inc. Orange County's list of community development districts doesn't include Winter Park Pines, but check the property tax bill for any special assessments.
What schools serve Winter Park Pines?
Orange County Public Schools' 2026-27 school zones place most of Winter Park Pines in Aloma Elementary, Glenridge Middle and Winter Park High School; some homes in the Cady Way and Cornwall Road area are zoned for Brookshire Elementary instead.
Zoning can change and varies by street, so confirm a specific address with Orange County Public Schools' Find My School tool, and compare school grades in the Florida School Accountability Reports.
Is Winter Pines Golf Club part of Winter Park Pines?
No. The former Winter Pines Golf Club is now Winter Park Pines Golf Club, a public 18-hole course at 950 S. Ranger Boulevard. The Winter Park City Commission approved buying it in January 2022, and state parcel records list the City of Winter Park as the owner. The course is on its own parcel inside city limits and is not a neighborhood amenity; the community association's website does not mention it.
Can you rent homes in Winter Park Pines short term?
No Winter Park Pines-specific rental rules turned up in our research. HOA documents often limit leasing, so confirm the current rules with the association before buying if you plan to rent.
