Winter Park Pines Homes with Sidewalks Community Features

Winter Park Pines Homes with Sidewalks Community Features

Welcome to Winter Park Pines, a picturesque subdivision nestled in the heart of Winter Park, Florida. This charming community, located in Orange County, offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, retirees, and young professionals alike.

One of the standout features of Winter Park Pines is its commitment to creating a walkable environment. With beautifully designed sidewalks winding through the neighborhood, residents can enjoy leisurely strolls or invigorating jogs while basking in the Florida sunshine. The community’s sidewalks not only enhance the aesthetic appeal of the area but also promote an active lifestyle, encouraging neighbors to connect and engage with one another.

The homes in Winter Park Pines are characterized by their diverse architectural styles, ranging from cozy single-family residences to more spacious properties, all set amidst lush landscaping and mature trees. Many of these homes come equipped with modern amenities, ensuring comfort and convenience for all residents.

In addition to its beautiful homes, Winter Park Pines is conveniently located near a variety of shopping, dining, and recreational options. Residents can easily access local parks, top-rated schools, and vibrant cultural attractions that Winter Park is renowned for. Whether you’re looking to enjoy a day at the park, explore the local art scene, or indulge in fine dining, everything is just a stone's throw away.

Experience the warmth and charm of Winter Park Pines, where community spirit thrives, and every day feels like a vacation. Your dream home awaits in this delightful neighborhood!

Newest Winter Park Pines Homes with Sidewalks Community Features

$669,900
3 Beds ⋅ 2 Baths ⋅ O6428430 MLS
Welcome to this beautifully updated three-bedroom, two-bathroom POOL home offering nearly 1,800 square feet of thoughtfully designed living space on a spacious lot backing to a peaceful conservation easement. Featuring separate living and family rooms, a remodeled kitchen, and an exceptional outdoor retreat, this inviting home is perfectly designed for both everyday living and entertaining. From the moment you arrive, the classic brick entry creates a warm first impression. Inside, the flexible floor plan provides plenty of space to gather, relax, work from home, or host guests. Laminate wood flooring and updated baseboards (2022) complement plantation shutters, recessed lighting, and ceiling fans throughout. Multiple storage closets add everyday functionality, while updated windows and French doors fill the home with natural light and seamlessly connect the indoor and outdoor living spaces. The remodeled kitchen (2021) features crisp white shaker cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, an oversized stainless-steel sink, and a breakfast bar with seating for four. A dedicated coffee bar and pantry add convenience, while the large bay window overlooks the pool and private backyard, creating the perfect backdrop for everyday living. The spacious primary suite offers a walk-in closet and ceiling fan. Its ensuite bathroom, renovated in 2022, features large marble-look tile, a double vanity with quartz countertops, and a beautifully updated walk-in shower with a frameless glass enclosure. Two additional guest bedrooms and an updated full bathroom complete the bedroom wing. Step outside to the true centerpiece of the home. Backing to a conservation easement, the backyard offers a peaceful setting with enhanced privacy. The screened, in-ground chlorine pool was completely refreshed in 2025 with new tile, resurfaced, and new pool light. The lanai deck was also resurfaced, creating an ideal space for swimming, outdoor dining, and entertaining family and friends. The outdoor improvements continue with fresh landscaping completed in 2025, including new sod, a stone pathway, French drains for improved drainage, and an updated irrigation timer. The fully fenced backyard (2023) provides additional privacy for pets, play, and gatherings. Ideally located near Cady Way Trail and Winter Park Pines Golf Course, you'll also enjoy convenient access to Cady Way Park amenities, including a community pool, playground, tennis and pickleball courts, beach volleyball, and walking trails. AdventHealth Winter Park and the Crosby Wellness Center are just minutes away, while Rollins College, Full Sail University, UCF, and Orlando International Airport are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines modern updates, flexible living spaces, and a private backyard retreat in one of Winter Park's most desirable locations. ROOF - 2024 ELECTRICAL PANELS - 2021

433 Gilbert Road, Winter Park
$848,949
5 Beds ⋅ 4 Baths ⋅ O6424409 MLS
BIG HOUSE. BIG KITCHEN. BIG FAMILY LIVING — FULLY RENOVATED IN WINTER PARK PINES. Currently the largest home on the market in Winter Park Pines under $900,000, this fully renovated 5-bedroom, 4-bath family home checks all the boxes. At the heart of the home is a brand-new designer kitchen anchored by a massive 9' x 5' double-waterfall island—the kind of kitchen where family memories are made. Two large skylights flood the kitchen and adjoining eating area with natural light, while extensive cabinetry and a custom range hood give the space a polished designer feel. And when company comes over? Hide the mess. The incredible 11-foot butler's pantry practically functions as a second kitchen, complete with its own sink, full-size refrigerator space, extensive cabinetry, countertops, and loads of storage. Party prep, appliances, groceries, and dirty dishes can stay tucked away while the main kitchen stays beautiful. Then there’s the primary suite. At approximately 13' x 22', this bedroom is large enough for its own sitting room, reading area, or private lounge. Add the oversized 7' x 8' walk-in closet, and you have a true owner's retreat. But the primary bathroom may steal the show. You might want to cancel the spa membership. Imagine ending the day in a six-foot freestanding soaking tub beneath a skylight, framed by a dramatic fluted marble backdrop. Add an oversized shower with dual showerheads, double vanity, heated smart toilet, and designer finishes, and you have a bathroom straight out of a magazine. Near the primary suite is another bedroom with its own ensuite bath—perfect for a home office, nursery, gym, guest room, or multigenerational living. Then send the kids to the other side of the house. The east wing features three large bedrooms and two baths, giving the younger members of the household a kingdom of their own where toys, homework, friends, and the occasional mayhem can stay comfortably contained. At the front of the home, the formal living room is filled with natural sunlight and offers a peaceful place to sit and unwind. When it’s time to gather everyone together, the separate 22-foot family room features a dramatic 10-foot linear fireplace and connects directly to the rear porch, gazebo, and backyard. Birthdays, holidays, Sunday dinners, graduation parties—this home gives you the space to bring everyone together without everyone sitting on top of each other. Outside, enjoy newly installed Zoysia grass, a private putting green, shaded relaxation areas, porch, and gazebo—perfect for entertaining, playing, or enjoying the Florida lifestyle. And this isn't simply a cosmetic renovation. Major improvements completed in 2026 include a new roof, electrical system, plumbing, and water heater. The HVAC system was installed in 2019. Enjoy convenient access to Winter Park Pines Golf Course, neighborhood walking paths, the community pool, major medical centers, and everything that makes Winter Park such a desirable place to live. Five bedrooms. Four baths. Separate bedroom wings. A magazine-worthy primary bath. A massive kitchen island. A second-kitchen-style pantry. Multiple living spaces. A putting green. And room for the entire family to actually live. This is a rare home giving a large family room to spread out, gather together, and truly enjoy it. If you've been searching Winter Park for space without sacrificing style, location, or modern finishes, 724 Monmouth Way deserves to be at the top of your list

724 Monmouth Way, Winter Park
$695,000
4 Beds ⋅ 3 Baths ⋅ O6410899 MLS
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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