Brookshire Heights 2nd Add Real Estate

Welcome to Brookshire Heights 2nd Add, a charming subdivision nestled in the heart of Winter Park, Florida. This delightful community is known for its serene atmosphere and family-friendly environment, making it the perfect place to call home.

Brookshire Heights boasts a variety of well-maintained homes, each with its own unique character and style. The tree-lined streets are adorned with lush greenery, providing a picturesque backdrop for leisurely strolls or bike rides. Residents enjoy the sense of community here, with friendly neighbors and a welcoming vibe that invites connection and camaraderie.

Located in the vibrant city of Winter Park, Brookshire Heights offers easy access to a wealth of amenities and attractions. Just a short drive away, you’ll find the renowned Park Avenue, lined with boutique shops, gourmet restaurants, and art galleries that showcase the area’s rich cultural heritage. For outdoor enthusiasts, the nearby parks and lakes provide ample opportunities for recreation, from picnics to paddleboarding.

Families will appreciate the top-rated schools in the area, ensuring that children receive an excellent education just moments from home. Additionally, the convenient location offers quick access to major highways, making commutes to downtown Orlando and beyond a breeze.

Whether you’re looking for a serene retreat or a vibrant community to grow your family, Brookshire Heights 2nd Add is a hidden gem in Winter Park that captures the essence of Florida living. Come explore this enchanting neighborhood and discover your perfect place to call home!

Newest Listings in Brookshire Heights 2nd Add

$549,000

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

Welcome home to your personal sanctuary in one of Winter Park’s most desirable neighborhoods. Frame your mornings in this beautifully updated 3-bedroom, 2-bathroom home featuring a charming front courtyard - the ultimate sunny spot for your morning coffee or setting up a chic bistro set. Inside, fresh interior paint amplifies the natural light pouring into the spacious main living room, beautifully framed by oversized windows and classic plantation shutters. The intuitive split floor plan ensures privacy, while sleek tile flooring throughout creates effortless, low-maintenance living. Seamlessly flowing from the main living spaces, an updated kitchen shines with granite countertops and stainless steel appliances. On the opposite side of the layout, a separate family room offers a cozy retreat that opens directly to a spacious screened-in back porch - your new favorite spot for outdoor lounging and entertaining. Beyond, a fully fenced backyard provides a private haven for pets and gardening. Best of all, the popular Cady Way Trail runs behind the property, perfect for morning jogs and evening strolls with no HOA restrictions. Complete with major system upgrades, including a brand-new HVAC, a 3-year-old roof, and a full PEX replumb with a central manifold, plus an attached oversized 1-car garage offering plenty of space for storage, this move-in-ready home perfectly combines peace of mind with unbeatable Winter Park charm.

624 Fitzwalter Drive, Winter Park

$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. 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

Start Your Search