Brookshire Heights 2nd Add Homes with Pool Community Features

Welcome to Brookshire Heights 2nd Addition, a delightful subdivision nestled in the heart of Winter Park, Florida. This charming community is known for its picturesque surroundings, friendly atmosphere, and prime location in Orange County, making it an ideal place for families, professionals, and retirees alike.

Brookshire Heights 2nd Add. boasts a variety of beautiful homes, many of which feature private pools, perfect for soaking up the Florida sun. Imagine spending warm afternoons lounging by your own serene oasis, or hosting unforgettable gatherings with friends and family in your backyard paradise. The community’s pool-centric homes create a relaxed, resort-like lifestyle that residents adore.

In addition to its stunning homes, Brookshire Heights offers a wealth of amenities designed to enhance your living experience. Tree-lined streets invite leisurely strolls or bike rides, while nearby parks provide ample opportunities for outdoor activities. The community is conveniently located close to Winter Park's vibrant downtown area, where you can explore an array of boutique shops, gourmet restaurants, and cultural attractions, including the renowned Charles Hosmer Morse Museum of American Art.

With its blend of comfort, community, and convenience, Brookshire Heights 2nd Addition is more than just a place to live; it's a lifestyle. Whether you're looking for a family-friendly environment or a peaceful retreat, this neighborhood has something for everyone. Come discover the charm of Brookshire Heights—your dream home awaits!

$899,900

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. The garage is air-cooled. 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 outdoor recreation. 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

Brookshire Heights 2nd Add Homes with Pool Community Features

Newest Brookshire Heights 2nd Add Homes with Pool Community Features