Winter Park Pines Homes with Sidewalks Community Features

Welcome to Winter Park Pines, a charming subdivision nestled in the heart of Winter Park, Florida. This picturesque community is known for its beautiful tree-lined streets, friendly neighbors, and a warm sense of belonging that makes it a perfect place to call home. Located in Orange County, Winter Park Pines offers residents the ideal blend of suburban tranquility and urban convenience.

One of the standout features of this community is its commitment to walkability. With well-maintained sidewalks throughout the neighborhood, residents can easily enjoy leisurely strolls, morning jogs, or evening bike rides while soaking in the natural beauty that surrounds them. Whether you're heading to a nearby park, visiting local shops, or simply enjoying the fresh air, the sidewalks make it easy to connect with your surroundings and foster a sense of community.

The homes in Winter Park Pines are as inviting as the neighborhood itself, featuring a variety of architectural styles and sizes to suit different lifestyles and preferences. Many of these residences come equipped with spacious yards, perfect for family gatherings or quiet evenings under the stars. The community also boasts excellent schools and recreational facilities, making it an ideal choice for families and professionals alike.

With its rich history, vibrant culture, and a plethora of outdoor activities, Winter Park Pines truly embodies the essence of Florida living. Discover the perfect blend of comfort, convenience, and community in this delightful neighborhood, where every day feels like a vacation! Come experience the charm of Winter Park Pines today!

Newest Winter Park Pines Homes with Sidewalks Community Features

$798,000

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

Pictures simply do not convey the beauty and feel of true ‘Sanctuary’ in this beautifully and breath-taking renovation! One of the biggest houses in Winter Park Pines and the only house in the community with a full kitchen butler's pantry. Spatially designed and updated for modern family living with separate bedroom wings for privacy, it also features quiet areas for contemplation and large areas for gatherings. It’s a hard choice of which is more impressive, the classic white kitchen with an open 9’x5’ island and 11’ butler's pantry featuring a 2nd sink and additional refrigerator, or the magazine-worthy design of the spacious Primary Bath. You get to choose! The Primary bedroom space (13x22) qualifies as a true retreat. All of this in the beauty of an established neighborhood on a quiet street where you can walk to the Winter Park Pines golf course, or take in many recreational opportunities the area has to offer (Cady Way Trail, Cady Way Pool, sports courts and ball fields galore) as well as a top-ranked hospital and healthcare facilities (Crosby Wellness Center or WP YMCA). Relax, the 2026 renovation has you covered for many years: New Roof, New wiring, New plumbing and water heater. The HVAC was new in 2019. Beautiful floors and fresh paint complete the package that is a rare find in such a fabulous location. Hurry! This one should be at the top of your list.

724 Monmouth Way, Winter Park

$695,000

4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

Welcome to your dream home in the highly sought-after community of Winter Park Pines! This beautifully maintained 4-bedroom, 3-bathroom residence offers 2,312 square feet of comfortable and stylish living space ideally designed for modern and multigenerational lifestyles. The recently remodeled primary suite is a true retreat, featuring new carpeting and tile flooring, dual granite vanities, an oversized walk-in shower with modern, upgraded fixtures, a new water closet, and thoughtful contemporary finishes throughout. Inside, you’ll find timeless architectural charm which includes a formal dining room, three spacious living areas, louvered window shutters, and elegant hardwood flooring. One of the living spaces is highlighted by a stunning brick fireplace overlooking the beautiful private pool area and fully fenced backyard — creating the perfect setting for entertaining, family gatherings, or simply unwinding in your own backyard oasis. In addition, this spectacular residence also boasts tasteful landscaping touches for exceptional curb appeal, a large two-car garage with electric opener, a newer shingle roof replaced in late 2023, and fresh interior paint throughout the home. Ideally located near Winter Park Pines Golf Club, Cady Way Trail, Ward Park, Showalter Field, tennis and pickleball courts, top-rated schools, and the many shopping and dining destinations of Park Avenue and historic downtown Winter Park. Don’t miss this rare opportunity to own a true Winter Park gem — schedule your private showing today!

715 S Ranger Boulevard, Winter Park

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