Winter Park Pines Homes with Pickleball Court(s) Amenities

Winter Park Pines Homes with Pickleball Court(s) Amenities

Welcome to Winter Park Pines, a charming subdivision nestled in the heart of Winter Park, Florida. Known for its picturesque tree-lined streets and vibrant community spirit, Winter Park Pines offers an idyllic setting for families, retirees, and everyone in between. This delightful neighborhood is characterized by its well-maintained homes, lush landscaping, and a friendly atmosphere that encourages outdoor activities and neighborly connections.

One of the standout features of Winter Park Pines is its impressive array of amenities, particularly the inclusion of pickleball courts. As one of the fastest-growing sports in the nation, pickleball offers a fun, engaging way for residents to stay active and socialize. Imagine stepping out your front door to enjoy a game with friends or neighbors, fostering a sense of community while enjoying the Florida sunshine. The pickleball courts are well-maintained and easily accessible, making it a perfect spot for both seasoned players and beginners looking to learn the game.

The homes in Winter Park Pines are thoughtfully designed, with many featuring spacious layouts and modern finishes. Whether you're seeking a cozy single-family home or a larger residence to accommodate a growing family, you'll find a variety of options to suit your needs. The neighborhood's close proximity to excellent schools, parks, and shopping centers enhances its appeal, making it a prime location for those looking to enjoy the best of Winter Park living.

Discover the charm of Winter Park Pines, where an active lifestyle meets a welcoming community. Come explore the homes and amenities that make this subdivision a true gem in Orange County!

Newest Winter Park Pines Homes with Pickleball Court(s) Amenities

$669,900
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, resurfaced, 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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