Winter Park Pines Homes with Tennis Court(s) Community Features

Winter Park Pines Homes with Tennis Court(s) Community Features

Welcome to Winter Park Pines, a vibrant and inviting subdivision nestled in the heart of Winter Park, Florida, within beautiful Orange County. This charming community is renowned for its picturesque landscapes, friendly atmosphere, and a lifestyle that perfectly blends relaxation with recreation.

One of the standout features of Winter Park Pines is its commitment to an active lifestyle, highlighted by the presence of homes with tennis courts. Whether you're a seasoned player or just looking to enjoy a casual game with friends, these private courts offer convenience and accessibility right at your doorstep. Imagine stepping out of your beautifully designed home and onto the court, ready to engage in a friendly match or practice your serve—all while enjoying the sunny Florida weather.

Winter Park Pines boasts a variety of home styles, each designed to cater to diverse tastes and preferences. From charming single-family homes to spacious residences, the community is perfect for families, retirees, and everyone in between. The tree-lined streets and well-maintained properties create a serene environment that residents are proud to call home.

Beyond the tennis courts, Winter Park Pines offers a wealth of amenities, including nearby parks, walking trails, and recreational facilities, ensuring that there’s always something to do. Plus, with the vibrant downtown Winter Park just a short drive away, residents can easily access a variety of dining, shopping, and cultural experiences.

Discover the perfect blend of comfort, community, and active living in Winter Park Pines—a place where your dream home awaits!

Newest Winter Park Pines Homes with Tennis Court(s) Community Features

$675,000
3 Beds 2 Baths Winter Park Pines SubDv. 32792 Zip Code
Welcome to this beautifully updated three-bedroom, two-bathroom pool home offering nearly 1,800 square feet of thoughtfully designed living space on a spacious lot backing to a peaceful conservation easement. Featuring separate living and family rooms, a remodeled kitchen, and an exceptional outdoor retreat, this inviting home is perfectly designed for both everyday living and entertaining. From the moment you arrive, the classic brick entry creates a warm first impression. Inside, the flexible floor plan provides plenty of space to gather, relax, work from home, or host guests. Laminate wood flooring and updated baseboards (2022) complement plantation shutters, recessed lighting, and ceiling fans throughout. Multiple storage closets add everyday functionality, while updated windows and French doors fill the home with natural light and seamlessly connect the indoor and outdoor living spaces. The remodeled kitchen (2021) features crisp white shaker cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, an oversized stainless-steel sink, and a breakfast bar with seating for four. A dedicated coffee bar and pantry add convenience, while the large bay window overlooks the pool and private backyard, creating the perfect backdrop for everyday living. The spacious primary suite offers a walk-in closet and ceiling fan. Its ensuite bathroom, renovated in 2022, features large marble-look tile, a double vanity with quartz countertops, and a beautifully updated walk-in shower with a frameless glass enclosure. Two additional guest bedrooms and an updated full bathroom complete the bedroom wing. Step outside to the true centerpiece of the home. Backing to a conservation easement, the backyard offers a peaceful setting with enhanced privacy. The screened, in-ground chlorine pool was completely refreshed in 2025 with new tile, repaired beam, resurfacing, and new pool light. The lanai deck was also resurfaced, creating an ideal space for swimming, outdoor dining, and entertaining family and friends. The outdoor improvements continue with fresh landscaping completed in 2025, including new sod, a stone pathway, French drains for improved drainage, and an updated irrigation timer. The fully fenced backyard (2023) provides additional privacy for pets, play, and gatherings. Ideally located near Cady Way Trail and Winter Park Pines Golf Course, you'll also enjoy convenient access to Cady Way Park amenities, including a community pool, playground, tennis and pickleball courts, beach volleyball, and walking trails. AdventHealth Winter Park and the Crosby Wellness Center are just minutes away, while Rollins College, Full Sail University, UCF, and Orlando International Airport are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines modern updates, flexible living spaces, and a private backyard retreat in one of Winter Park's most desirable locations. ROOF - 2024 ELECTRICAL PANELS - 2021

433 Gilbert Road, Winter Park

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