Winter Park Single-Family Homes

Winter Park, FL offers a wide variety of single-family homes, from mid-century ranch-style residences and bungalows to modern new construction and custom estates. Homes range in size and style to suit both first-time buyers and luxury homeowners.

Single-family homes in Winter Park typically range from $500,000 to over $5 million, depending on location, square footage, architectural style, and proximity to lakes or downtown Park Avenue. Homes in the Vias or along the Chain of Lakes fall on the higher end.

Top neighborhoods include Olde Winter Park, Windsong, The Vias, and Kenilworth Shores. These communities are known for tree-lined streets, strong schools, architectural charm, and access to parks and lakes.

Yes, many single-family homes for sale are located just blocks from Park Avenue, Winter Park’s charming downtown district. These properties offer walkability to restaurants, boutiques, art museums, and the Winter Park Farmers’ Market.

Yes. Winter Park has an active luxury infill development market, with custom-built single-family homes replacing older structures. These modern homes often feature open floor plans, energy-efficient systems, smart tech, and designer finishes.

Absolutely. Winter Park is known for its top-rated schools, safe neighborhoods, family-oriented parks, and community events. Many single-family homes are located near excellent elementary and secondary schools, both public and private.

Property taxes in Winter Park are typically around 1%–1.25% of the assessed home value. Buyers should also factor in homestead exemptions, municipal services, and any potential CDD or HOA fees, depending on the neighborhood.

Yes, many single-family homes in Winter Park feature spacious yards, mature landscaping, patios, and private pools. This outdoor space is ideal for families, pets, and entertaining—especially in Florida’s year-round mild climate.