Brookshire Heights Real Estate

Brookshire Heights Real Estate

Welcome to Brookshire Heights, a charming subdivision nestled in the heart of Winter Park, Florida. This picturesque community in Orange County offers a delightful blend of suburban tranquility and urban convenience, making it an ideal place for families, retirees, and professionals alike.

Brookshire Heights is celebrated for its lush landscapes, mature trees, and well-maintained homes that reflect a variety of architectural styles. The neighborhood exudes a warm, inviting atmosphere, perfect for those seeking a tight-knit community feel. Residents enjoy access to beautiful parks, scenic walking trails, and family-friendly recreational facilities, ensuring that outdoor enthusiasts have plenty of opportunities to stay active and connected with nature.

The subdivision is conveniently located near Winter Park's vibrant downtown area, known for its eclectic mix of boutiques, cafes, and cultural attractions. Whether you’re indulging in a leisurely afternoon at the renowned Charles Hosmer Morse Museum of American Art or enjoying a weekend stroll along the picturesque canals, there’s always something to explore just a stone’s throw away.

Families will appreciate the proximity to highly-rated schools and educational institutions, ensuring that children receive a top-notch education. Additionally, Brookshire Heights boasts easy access to major highways, making commutes to nearby cities and attractions a breeze.

In Brookshire Heights, you’ll find more than just a place to live; you’ll discover a community that embraces a lifestyle of comfort, convenience, and connection. Come experience the charm of this delightful subdivision and make it your new home!

Newest Listings in Brookshire Heights

2345 Brookshire Avenue, Winter Park
$795,000
3 Beds ⋅ 3 Baths ⋅ Brookshire Heights SubDv. ⋅ 32792 Zip Code
Now offered at $795,000 in highly sought-after Brookshire Heights! Set among beautiful trees and sidewalk-lined streets, this inviting Winter Park home pairs neighborhood charm with spacious living areas, a private backyard, and an expansive primary retreat. Sellers have also just installed all-new R-38 attic insulation, adding to the home’s extensive list of recent improvements. A charming flagstone, ivy-lined entry and fresh landscaping welcome you to this 3-bedroom, 3-bathroom home, offering 2,488 square feet on a private .21-acre lot. Vaulted ceilings and multiple living areas create flexible spaces for entertaining, relaxing, and everyday living, with an easy flow connecting the home’s gathering spaces. The kitchen features white shaker cabinetry, granite countertops, brand-new stainless-steel appliances, a coffee/wine bar, and breakfast-bar seating for four. From casual mornings to dinner with friends, this central gathering space keeps everyone connected. Thoughtfully added in 2017, the expansive primary suite offers a retreat of its own, complete with a separate sitting room or office and a spacious walk-in closet. The spa-inspired ensuite features a large tiled shower with multiple shower heads and a frameless glass enclosure, a dual vanity with marble countertops, and a separate water closet. A secondary bedroom with its own ensuite bathroom offers added comfort and privacy. All bathrooms have been updated, and brand-new bedroom carpeting, recessed lighting, and ceiling fans add comfort throughout. Outside, a fully fenced backyard with fencing replaced in 2025, a brand-new deck, and fresh landscaping creates an inviting setting for outdoor dining, entertaining, or simply unwinding. Enjoy the welcoming setting of Brookshire Heights, just steps from Brookshire Elementary and close to the Cady Way pool, playground, beach volleyball, tennis and pickleball courts, Cady Way Trail, and Winter Park Pines Golf Course. The location also offers convenient access to UCF, Rollins College, Full Sail University, AdventHealth Winter Park, and Crosby Wellness Center, with Orlando International Airport approximately 25 minutes away. Recent improvements include all-new R-38 attic insulation, brand-new stainless-steel kitchen appliances, new bedroom carpet, a new deck, and fresh landscaping. Roof updates: main roof—2022; family room—2019; primary suite—2017. HVAC—2021. Mini-split—2026. Discover the space, privacy, and neighborhood charm waiting for you at 2345 Brookshire.

2345 Brookshire Avenue, Winter Park

2260 Coldstream Drive, Winter Park
$675,000
4 Beds ⋅ 2 Baths ⋅ Brookshire Heights SubDv. ⋅ 32792 Zip Code
Virtually Staged. Zoned for Fantastic Winter Park Schools, this 4 bed, 2 bath recently renovated abode is waiting for you. Located on a quiet, tree-lined street, you can walk to highly rated Brookshire Elem and Winter Park High. The open-plan living space has beautiful travertine tile floors flowing through the kitchen, dining room, and living room. Renovated in 2026, the kitchen offers quartz counter tops, new appliances, under cabinet lighting, custom tile backsplash, and pendant lights. Flowing from the kitchen to the dining room and through to the living room, this open floor plan is sure to please. Double French doors open from the sunny living room to the spacious backyard. The oversized two-car garage and laundry room are just off the kitchen. Travertine continues down the hall, while all 4 bedrooms have newly installed wood flooring (2024). The primary bedroom has a renovated ensuite (2026) with enlarged walk-in shower, custom tile, new fixtures, and new quartz topped vanity. All 4 bedrooms have window shutters and new ceiling fans, and the renovated hall bath (2025) offers new quartz topped double sink vanity, new mirrors, and tub/shower tile surround. Out back, the grassy backyard with new fencing and St Augustine sod (2025) offers plenty of room for kids and pets to play or even a future pool addition. Located just 3 miles to Rollins College and the Park Ave shopping and dining district, this prime location offers other, even closer, benefits. Cady Way Park is 2 blocks away with a community pool, pickleball courts, tennis courts, picnic tables, and access to the Cady Way Bike Trail. NEW HVAC 2024, Roof 2015, updated electrical box 2014, and house re-piped with CPVC 2009. Come check out this charming move-in ready Winter Park house and make it your own home.

2260 Coldstream Drive, Winter Park

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