Golfside

Golfside is on Summerfield Road, Golfside Drive and Fairway Drive, beside Winter Park Pines Golf Club. It is inside City of Winter Park limits, and homes have Winter Park 32792 addresses.

Golfside has 125 single-family homes built from 1966 to 1979, according to Orange County Property Appraiser records. Nearly all are one-story, from about 1,290 to 3,370 square feet on lots of about a quarter to a half acre, and MLS listings show 3 to 5 bedrooms. There are no condos or townhomes.

Over the past two years (MLS data, October 2026), homes in Golfside sold 17 times for a median of about $710,000, ranging from about $455,000 to $920,000. For today's listings, see the top of this page.

No mandatory HOA was found. MLS listings describe Golfside as having no HOA and show no HOA fee. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Golfside, but check the property tax bill for any special assessments.

Orange County Public Schools' 2026-27 school zones place Golfside in Brookshire Elementary, Glenridge Middle and Winter Park High School.

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.

No. Winter Park Pines Golf Club is a public 18-hole course owned by the City of Winter Park; there is no membership or HOA tie to Golfside. Golfside is also separate from Golfside Villas, a condominium on S. Semoran Boulevard, from Greenview at Winter Pines, a separate plat of 1978–1982 homes on Golfside Drive, and from Winter Park Pines.

No Golfside-specific rental rules turned up in our research, and no mandatory HOA was found. City of Winter Park rules apply, so confirm them before buying if you plan to rent short term.