Winfield

Winfield is off Fennell Street in Maitland, on Bobtail Drive, Birman Street, Korat Lane, Tortoise Shell Drive, Chartreux Lane and Falkner Road. Homes have Maitland 32751 addresses and are inside City of Maitland limits in Orange County.

Winfield has 224 single-family homes built from 1995 to 1999, according to Orange County Property Appraiser records. Most are one-story and range from about 1,210 to 2,450 square feet on lots of about 0.12 to 0.27 acre. MLS listings show 3 to 5 bedrooms. There are no townhomes or condos.

Over the past two years (MLS data, October 2026), homes in Winfield sold 20 times for a median of about $420,000, ranging from about $320,000 to $545,000. For today's listings, see the top of this page.

MLS records don't state the dues period consistently, so confirm current dues with the association. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Winfield, but check the property tax bill for any special assessments. The association is Winfield Homeowners Association, Inc.

Orange County Public Schools' 2026-27 school zones place Winfield in Lake Sybelia Elementary, Lockhart Middle and Edgewater 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.

Yes. Every Winfield home is inside City of Maitland limits in Orange County, according to county records. The name Winfield at Maitland Park also appears in a listing and on a realtor site. Two apartment complexes on Grand Brook Circle and Grand Isle Circle share Winfield's county subdivision code but are not part of its 224 homes.

No Winfield-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.