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 lush landscapes and charming residential atmosphere, this community is an ideal haven for families, retirees, and anyone seeking a serene lifestyle just minutes away from the vibrant city of Orlando.

Winter Park Pines boasts an array of beautifully designed homes, each featuring inviting architecture and well-maintained yards. One of the standout features of this community is its extensive network of sidewalks, encouraging residents to enjoy leisurely strolls, morning jogs, or evening bike rides amidst the picturesque scenery. These sidewalks not only promote an active lifestyle but also foster a sense of camaraderie among neighbors, making it easy to connect with friends and family in this tight-knit community.

The subdivision is conveniently located near excellent schools, shopping centers, and recreational facilities, allowing residents to enjoy the best of both worlds—tranquility and accessibility. Families will appreciate the proximity to parks and playgrounds, where children can play freely and safely. Additionally, Winter Park’s renowned dining and cultural scene is just a short drive away, offering a variety of options for dining, shopping, and entertainment.

Whether you’re looking for a cozy family home or a peaceful retreat, Winter Park Pines provides the perfect backdrop for your next chapter. Embrace the charm and warmth of this community, where every day feels like a delightful escape. Come explore Winter Park Pines and discover the ideal place to call home!

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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