Winter Park Pines Homes with Playground Community Features

Welcome to Winter Park Pines, a picturesque subdivision nestled in the heart of Winter Park, Florida, within the vibrant Orange County. Known for its enchanting tree-lined streets and a friendly, welcoming atmosphere, Winter Park Pines offers a unique blend of suburban charm and modern convenience, making it an ideal place to call home.

As you explore this delightful community, you'll discover a variety of beautifully designed homes that cater to diverse lifestyles and preferences. Each residence boasts spacious layouts, contemporary finishes, and lush landscaping, creating an inviting environment for families, professionals, and retirees alike. The community is renowned for its strong sense of togetherness, with neighbors often gathering for events and enjoying the shared amenities.

One of the standout features of Winter Park Pines is its family-friendly playground, a perfect spot for children to play and make lifelong memories. This safe and well-maintained area encourages outdoor activities and social interactions, fostering a vibrant community spirit. Parents can relax knowing their little ones have a dedicated space to explore, while adults can enjoy leisurely strolls or picnics in the surrounding green spaces.

Beyond the playground, Winter Park Pines is conveniently located near a wealth of shopping, dining, and recreational options. The nearby scenic lakes, parks, and trails offer endless opportunities for outdoor enthusiasts to engage in activities like biking, jogging, or simply soaking in the sun.

With its charming homes, community-focused amenities, and prime location, Winter Park Pines is more than just a neighborhood; it's a place where cherished memories are made. Come discover the warmth and allure of Winter Park Pines, and find your perfect slice of Florida living today!

Newest Winter Park Pines Homes with Playground 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

$849,949

5 Beds ⋅ 4 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

LIGHTING FAST RESPONSE - FULLY RENOVATED 5-BEDROOM, 4-BATH WINTER PARK ESTATE Welcome to 724 Monmouth Way, a beautifully reimagined five-bedroom, four-bath estate designed for comfortable family living, elegant entertaining, and everyday luxury. Renovated in 2026, this spacious home features thoughtfully separated bedroom wings, impressive living areas, abundant natural light, and designer finishes throughout. The expansive 13-by-22-foot primary suite offers enough space for a private sitting area, reading retreat, or lounge within the bedroom. The luxurious primary bathroom features a double vanity, an oversized shower with dual showerheads, a heated smart toilet, and a six-foot freestanding soaking tub positioned beneath a built-in skylight. Marble fluted accent walls surrounding the tub and shower create a dramatic, spa-like atmosphere. A generous 7-by-8-foot walk-in closet provides abundant storage. At the heart of the home is a newly designed, chef-inspired kitchen featuring a striking 9-by-5-foot double-waterfall island, extensive cabinetry, exceptional storage, a custom range hood surround, and an elegant cabinet column that gives the kitchen a truly distinctive designer look. Two large skylights above the kitchen and adjoining casual dining area fill the space with natural light, creating a bright, open, and inviting atmosphere throughout the day. The adjoining butler’s pantry functions as a second kitchen and includes its own sink and faucet, full-size refrigerator space, extensive cabinetry, and additional countertop space. Prepare meals, store small appliances, and keep entertaining messes neatly tucked away from the main kitchen. A guest bedroom located near the primary suite includes its own private ensuite bathroom. This flexible left-wing space is ideal for overnight guests, a nursery, private office, fitness room, or multigenerational living arrangement. On the opposite side of the home, the right bedroom wing offers added privacy and separation from the primary suite. This hallway includes three additional spacious bedrooms, a full bathroom, and a convenient half bathroom. The large formal living room is filled with natural light from its front-facing windows. A separate 22-foot family room creates an impressive gathering space and features a dramatic 10-foot linear fireplace, making it the perfect setting for holidays, celebrations, movie nights, and everyday relaxation. Outside, the large, thoughtfully designed backyard features newly installed Zoysia grass, a private putting green, and naturally shaded areas perfect for relaxing, entertaining, or enjoying the Florida lifestyle. Major improvements include a new roof, electrical system, plumbing, and water heater completed in 2026, along with an HVAC system installed in 2019. This exceptional Winter Park home combines generous living space, modern luxury, flexible accommodations, dramatic natural light, and extensive renovations in one remarkable property.

724 Monmouth Way, Winter Park

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