Winter Park Pines Homes with Sidewalks Community Features

Welcome to Winter Park Pines, a delightful subdivision nestled in the heart of Winter Park, Florida, within the vibrant Orange County. This charming community is renowned for its picturesque tree-lined streets and inviting atmosphere, making it the perfect place to call home.

Winter Park Pines offers a unique blend of suburban tranquility and urban convenience. The homes in this community are thoughtfully designed, featuring modern amenities and spacious layouts that cater to a variety of lifestyles. Whether you’re a growing family, a retiree, or a young professional, you’ll find a home that meets your needs here.

One of the standout features of Winter Park Pines is its commitment to community connectivity. The neighborhood boasts well-maintained sidewalks that encourage residents to stroll through the area, fostering a sense of camaraderie among neighbors. Imagine evening walks with family, morning jogs, or casual bike rides as you explore the beauty of your surroundings. The sidewalks not only promote an active lifestyle but also enhance the community spirit, making it easy to meet friends and neighbors along the way.

In addition to its scenic paths, Winter Park Pines is conveniently located near local parks, shopping centers, and top-rated schools, ensuring that everything you need is just a stone's throw away. With its perfect blend of community features and prime location, Winter Park Pines is more than just a neighborhood; it’s a place where memories are made and cherished. Discover the charm of Winter Park Pines today and find your dream home in this enchanting community!

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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