Brookshire Heights Homes with Sidewalk Exterior Features

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

Brookshire Heights is renowned for its beautifully designed homes, many of which feature inviting sidewalk exterior designs. These charming walkways not only enhance the aesthetic appeal of the neighborhood but also promote a sense of community, encouraging residents to stroll, jog, or bike through the tree-lined streets. Imagine enjoying your morning coffee on your front porch while greeting friendly neighbors as they pass by!

The homes in Brookshire Heights boast a variety of architectural styles, catering to diverse tastes and preferences. From cozy single-family residences to spacious multi-bedroom homes, there’s something for everyone in this welcoming enclave. Many properties come equipped with modern amenities, spacious yards, and beautiful landscaping, making them perfect for both relaxation and entertaining.

Living in Brookshire Heights means you’re just a stone’s throw away from Winter Park’s vibrant downtown area, filled with charming boutiques, gourmet restaurants, and cultural attractions. Enjoy the lush parks, scenic lakes, and top-rated schools that make this area a coveted destination for families.

Whether you’re looking to buy your first home, downsize, or invest in a property, Brookshire Heights offers a unique opportunity to embrace the Florida lifestyle in a community that feels like home. Come discover your dream home in this enchanting neighborhood today!

Newest Brookshire Heights Homes with Sidewalk Exterior Features

$825,000

3 Beds ⋅ 3 Baths ⋅ Brookshire Heights SubDv. ⋅ 32792 Zip Code

Welcome to this beautiful Winter Park home where a flagstone, ivy-lined entry sets the tone for the inviting spaces found within. Tucked away on a private .21-acre lot, this 3-bedroom, 3-bathroom home offers 2,488 square feet of thoughtfully designed living space with vaulted ceilings, multiple living areas, and an effortless flow that makes everyday living and entertaining feel natural. From the moment you arrive, the lush new landscaping and charming entry create a warm first impression, while the spacious interior offers plenty of room for family and friends to gather, relax, and enjoy time together. Inside, the home's multiple living areas provide exceptional flexibility, creating inviting spaces for entertaining, casual gatherings, or simply relaxing with family. The kitchen serves as a natural gathering point, featuring white shaker cabinetry, granite countertops, brand-new stainless-steel appliances, a convenient coffee/wine bar, and a breakfast bar with seating for four. Whether hosting friends for dinner or enjoying a quiet morning together, the layout offers space for every occasion. The primary suite, thoughtfully added in 2017, is a private retreat designed for both comfort and relaxation. A dedicated sitting room or office provides additional flexibility, while the spacious walk-in closet offers abundant storage. The expansive ensuite bathroom delivers a true spa-like experience, featuring a large tiled shower with multiple shower heads and a frameless glass enclosure, creating a luxurious place to unwind at the end of the day. A dual vanity with elegant marble countertops and a separate water closet complete this serene retreat. A secondary bedroom with its own ensuite bathroom provides additional comfort and privacy for guests or family members. All bathrooms have been updated, and the bedrooms feature brand-new carpet, while recessed lighting and ceiling fans throughout add to the home's comfort. Step outside to enjoy the privacy of the fully fenced backyard, with fencing replaced in 2025, a brand-new deck, and beautiful new landscaping. The outdoor space offers another inviting setting for relaxing, entertaining, or enjoying Florida's year-round lifestyle. Beyond the home, the location places you 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. You'll also enjoy convenient access to UCF, Rollins College, Full Sail University, AdventHealth Winter Park, and Crosby Wellness Center, with Orlando International Airport approximately 25 minutes away. With its welcoming entry, versatile living spaces, spa-inspired primary retreat, private setting, and exceptional Winter Park location, this home offers an ideal backdrop for gathering, relaxing, and making memories with family and friends. ROOF(S) - Main - 2022, Family Room - 2019, Primary Suite - 2017 HVAC - 2021 MINI-SPLIT - 2026

2345 Brookshire Avenue, 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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