Winter Park Homes with Pool

Winter Park Homes with Pool

Welcome to Winter Park, Florida, a picturesque gem nestled in Orange County, renowned for its stunning landscapes, vibrant culture, and charming neighborhoods. This enchanting city offers a perfect blend of small-town warmth and modern amenities, making it an ideal choice for families, retirees, and young professionals alike.

Winter Park is celebrated for its beautiful tree-lined streets, lush parks, and a rich history that dates back to the late 1800s. The heart of the city is the iconic Park Avenue, where you’ll find an array of boutique shops, delightful cafes, and exquisite dining options. Whether you're exploring the scenic canals or enjoying a leisurely stroll through the renowned Winter Park Rose Garden, this community exudes a welcoming atmosphere that captivates residents and visitors alike.

One of the standout features of Winter Park is its stunning homes, many of which come with private pools, providing an oasis for relaxation and entertainment. Imagine soaking up the Florida sun in your own backyard, hosting summer barbecues, or enjoying peaceful evenings under the stars. These homes with pools not only enhance your lifestyle but also add significant value to your investment.

With a variety of architectural styles ranging from charming bungalows to luxurious estates, Winter Park offers something for everyone. The real estate market here is thriving, making it an opportune time to find your dream home. Come and discover the allure of Winter Park, where every day feels like a vacation, and your ideal lifestyle awaits!

Newest Winter Park Homes with Pool

$6,888,888
4 Beds ⋅ 5 Baths ⋅ B26030158 MLS
Set in the perfect Winter Park location, within exclusive Via Tuscany, this unique, RESILIENT CONSTRUCTION residence built by Developer & Builder Group, offers a rare blend of enduring quality, refined privacy, and effortless sophistication. Showcasing the finest European finishes, premium appliances, and exquisite light fixtures; this home is filled with clear, natural light and fresh air, creating a truly unique living experience with timeless luxury in every detail. Located minutes away from Park Avenue's upscale shopping and dining, many cultural attractions, and easy access to downtown Orlando.

2661 Via Tuscany, Winter Park
$2,650,000
4 Beds ⋅ 4 Baths ⋅ O6389829 MLS
Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood entry door, to its charming striped awnings and the flicker of gas lanterns, every detail of the exterior is carefully curated. Classic marble-paved patios frame the home, and a courtyard-style pool with fountain and sandblasted marble decking invites quiet relaxation or festive gatherings. Inside, soaring ceilings, beautiful hardwood floors and immersive color-drenched rooms create an inviting space that is luxurious but unpretentious, bold yet serene. The stunning staircase features a custom wrought-iron railing with an antique finish, offering a striking architectural focal point. The chef’s kitchen, a culinary sanctuary and social hub, is complete with graphite La Cornue range and pot filler, Monogram paneled refrigerator, custom plaster hood, quartzite countertops and backsplash, and grand center island that opens to a gathering room with a gas fireplace. This more relaxed living area flows effortlessly through French doors to the pool and patios, creating an ideal indoor-outdoor lifestyle. A butler’s pantry with a second refrigerator, cabinetry and prep space adds functionality, while the formal dining room, living room, and bar area with sink and built-in beverage cooler are ideal for entertaining. A beautiful downstairs powder bath features designer wallpaper, elegant sconces and custom cabinetry. The upstairs primary suite offers spa-like serenity, including a wet room complete with soaking tub framed by a picture window. Three additional bedrooms include one with an en-suite bath, while the other two share a hallway-accessible bath with double vanity and walk-in tiled shower. This masterpiece set in the heart of Winter Park, thoughtfully surrounded by lush landscaping and carefully placed privacy screens, offers polish and presence in an ideal location.

541 W Canton Avenue, Winter Park
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