Winter Park Pines Homes with Sidewalks Community Features

Welcome to Winter Park Pines, a delightful subdivision nestled in the heart of Winter Park, Florida. Known for its charming streets and vibrant community spirit, Winter Park Pines offers an idyllic blend of suburban tranquility and urban convenience. This picturesque neighborhood is situated within Orange County, just a stone's throw from the scenic beauty and cultural richness that Winter Park is famed for.

One of the standout features of Winter Park Pines is its family-friendly atmosphere, highlighted by well-maintained sidewalks that meander throughout the community. These sidewalks not only encourage leisurely strolls and morning jogs but also foster connections among neighbors, making it easy to enjoy a friendly wave or a chat with passersby. Imagine evenings spent walking your dog or enjoying a bike ride with the family, all within the safety and comfort of your own neighborhood.

The homes in Winter Park Pines are thoughtfully designed, offering a variety of styles to suit diverse tastes and preferences. Many properties feature lush landscaping, spacious yards, and modern amenities, making them perfect for families, retirees, and everyone in between. With local parks, schools, and shopping centers just minutes away, residents enjoy the convenience of having everything they need right at their fingertips.

Whether you're looking for a place to raise a family or simply seeking a serene environment to call home, Winter Park Pines is a community that truly has it all. Come explore the charm and warmth of this inviting neighborhood—your dream home awaits!

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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