Winter Park Homes with Colonial Architectural style

Winter Park: A Charming City with Colonial Homes

Located in Orange County, Florida, Winter Park is a beautiful city known for its charming neighborhoods and rich history. With its picturesque streets and stunning architecture, Winter Park offers a unique blend of old-world charm and modern amenities.

One of the architectural styles that you'll find in Winter Park is the Colonial style. Homes with Colonial architecture are true gems in this city. These homes typically feature symmetrical facades, traditional details, and a sense of timeless elegance. You'll often see classic elements such as columns, dormer windows, and a central chimney.

Living in a Colonial-style home in Winter Park is like stepping back in time while enjoying all the comforts of modern living. These homes exude a sense of grandeur and sophistication, making them highly sought after by homeowners who appreciate the beauty of historical architecture.

Beyond the stunning homes, Winter Park offers residents a vibrant community with a thriving arts scene, upscale shopping boutiques, and a wide array of dining options. The city is also home to several beautiful parks and lakes, providing ample opportunities for outdoor recreation.

Whether you're strolling along Park Avenue, exploring the museums, or enjoying a picnic by the lake, Winter Park has something for everyone. With its Colonial homes and charming atmosphere, Winter Park is a city that captures the hearts of both residents and visitors alike.

Newest Winter Park Homes with Colonial Architectural style

$925,000

4 Beds ⋅ 3 Baths ⋅ Brookshire Heights 2nd Add SubDv. ⋅ 32792 Zip Code

Welcome to this warm and inviting home in the desirable Brookshire Heights neighborhood, ideally positioned on a corner lot along a beautiful street in a sought-after community. Offering more than 2,500 square feet of living space, this spacious residence features four bedrooms and two-and-a-half baths, with an open, comfortable layout designed for both everyday living and entertaining. The home has been thoughtfully updated and maintained over the years, blending timeless character with modern conveniences. The kitchen was beautifully remodeled in 2021 with new cabinetry, appliances, flooring, and countertops, while the family room was enhanced with additional air-conditioning ducts and vents for added comfort. The second full bath was also remodeled in 2021, and the downstairs powder room received a stylish update in 2025.Significant improvements include new wood flooring downstairs and refinished and stained upstairs floors in 2019, a new HVAC system with an additional upstairs unit and complete ductwork replacement in 2020, and a customized primary closet in 2022. The primary suite continues to impress with a new porch door and a private balcony railing added in 2026. A new water heater was installed in 2023, while the main sewer line exiting the home was replaced in 2024.Outdoor living has been equally well considered, with a screened porch enclosure, a covered side patio, new fencing, and refreshed landscaping creating inviting spaces to relax and entertain. Beyond the home itself, the location is exceptional—conveniently situated in a wonderful community with Cady Way pool and Cady Way trail which spans 7.2 miles and connects to the Seminole trail for bike riding, running and walking. Highly regarded schools and easy access to the area’s everyday amenities. With its generous living spaces, extensive updates, inviting outdoor areas, and prime corner-lot setting, this Brookshire Heights home offers an exceptional opportunity to enjoy a beautifully cared-for residence in a highly desirable location.

2572 Fifeshire Drive, Winter Park

$147,000

1 Beds ⋅ 1 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code

Virtually Staged. LOCATION, CONVENIENCE, AND EASY LIVING IN WINTER PARK! This move-in-ready first-floor, 1-bedroom, 1-bath condo features an open living and dining area, wood flooring throughout the main living areas, tile flooring in the primary bedroom, a private screened-in balcony, a fully equipped kitchen, and a stackable washer and dryer. Conveniently located near UCF, Rollins College, Valencia College, Park Avenue, and Downtown Orlando, with easy access to shopping, dining, and major highways. Community amenities include two pools, a tennis court, fitness center, and clubhouse. HOA includes water, trash, internet, pest control, exterior maintenance, and grounds care. A great opportunity to enjoy a low-maintenance lifestyle in a highly convenient Winter Park location.

285 Lewfield Circle Unit 285, Winter Park

Start Your Search