Vintage homes for sale & real estate in Winter Park, FL

Vintage Home for sale in Winter Park, FL:

Under Construction. Welcome to Westchester Avenue—an exceptional new construction residence just moments from the iconic Park Avenue in Winter Park, celebrated for its upscale dining, refined cafés, and luxury boutique shopping. This custom-built home exemplifies true craftsmanship, showcasing elegant architecture and exquisite finishes throughout. No expense was spared in its creation. From the moment you step inside, the grand foyer sets the tone with its striking checkerboard Calacatta and Armani porcelain tile—an elegant introduction to the refined design that unfolds. The open-concept living, dining, and kitchen areas provide a seamless layout, ideal for both intimat

Vintage Home for sale in Winter Park, FL:

Just two blocks from East End Market and the Audubon Park K8 campus, this thoughtfully renewed four bedroom home sits in one of the area’s most loved walkable pockets. The renovation was approached with care, intention, and a focus on comfortable everyday living. The layout has been reworked to create an easy sense of flow, highlighted by a newly formed primary suite and a kitchen designed with both function and quiet style in mind. Natural light fills the interior through new windows, complementing warm finishes throughout: 20 mil vinyl plank flooring, soft close cabinetry with quartz countertops, and modern yet understated tilework in the kitchen and baths. Behind the kitchen, a fle

Vintage Home for sale in Winter Park, FL:

Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake Baldwin trails, and the dining and boutiques of Park Avenue. This location places you close to Rollins College, Winter Park High, and the cultural center of Winter Park FL. Inside, natural light moves through open living spaces finished with wide porcelain tile floors. The kitchen stands as a sophisticated gathering space with a large quartz island, custom cabinetry, Bosch appliances, and a walk in pantry. The primary suite offers a peaceful retreat with direct access to the pool and a spa inspired bath. A second ensuite bedroom, dedicated office, and generous flex room pro

Vintage Home for sale in Winter Park, FL:

One or more photo(s) has been virtually staged. This beautiful two-story residence is located in the highly desired Temple Heights neighborhood in the heart of Winter Park. Situated on an expansive double lot, this well-maintained home offers over 3,900 sq ft of heated living space and features 5 bedrooms and 4 bathrooms in the main home, plus a large separate pool home/In-Law Suite complete with its own bathroom and kitchenette. The home features original hardwood and vinyl flooring throughout, high vaulted ceilings, and an open floor plan designed for both comfort and entertaining. The family room and kitchen overlook the covered lanai, oversized pool, and spacious, private backyard. Fren