Winter Park Pines Homes with Sidewalks Community Features

Welcome to Winter Park Pines, a charming subdivision nestled in the heart of Winter Park, Florida, within the vibrant Orange County. This serene community is a hidden gem, offering a perfect blend of suburban tranquility and urban convenience. Known for its picturesque streets lined with lush trees and well-maintained homes, Winter Park Pines is an ideal place for families, retirees, and anyone seeking a peaceful yet connected lifestyle.

One of the standout features of Winter Park Pines is its commitment to community living, highlighted by the inviting sidewalks that grace the neighborhood. These sidewalks not only enhance the aesthetic appeal of the area but also encourage residents to enjoy leisurely strolls, morning jogs, or evening bike rides. It’s a place where neighbors become friends, and children can safely play outside, fostering a true sense of community spirit.

The homes in Winter Park Pines are designed with comfort and style in mind, with a variety of architectural designs to suit diverse tastes. Many properties boast spacious yards, perfect for outdoor gatherings or simply soaking in the Florida sunshine. With nearby parks, shopping centers, and dining options, residents have everything they need just a stone’s throw away.

Living in Winter Park Pines means embracing a lifestyle rich in community, convenience, and charm. Whether you’re admiring the scenic views or enjoying the friendly neighborhood vibe, this subdivision offers a warm welcome to all who call it home. Come discover the magic of Winter Park Pines – where community and comfort unite!

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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