Winter Park Pines Homes with Pool Community Features

Welcome to Winter Park Pines, a delightful subdivision nestled in the heart of Winter Park, Florida. Known for its picturesque tree-lined streets and vibrant community spirit, Winter Park Pines offers a serene yet engaging lifestyle that appeals to families, retirees, and everyone in between. The charm of this neighborhood is accentuated by its proximity to the stunning parks, lakes, and cultural attractions that Winter Park is famous for.

One of the standout features of Winter Park Pines is its inviting homes, many of which boast private swimming pools, perfect for those warm Florida days. Imagine stepping out into your backyard oasis, where you can relax by the poolside, host summer barbecues, or enjoy a refreshing swim with family and friends. The community is designed to foster a sense of togetherness, with friendly neighbors and a welcoming atmosphere that makes it easy to feel at home.

In addition to the beautiful homes, Winter Park Pines is conveniently located near top-rated schools, shopping centers, and dining options, ensuring that everything you need is just a stone’s throw away. Outdoor enthusiasts will appreciate the nearby parks and recreational areas, perfect for hiking, biking, and enjoying nature.

Whether you’re seeking a tranquil retreat or a vibrant community to call home, Winter Park Pines has it all. Embrace the Florida lifestyle in this charming subdivision, where your dream home with a pool awaits!

Newest Winter Park Pines Homes with Pool Community Features

$669,900

3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

Bright, airy, and designed for a resort living! Welcome to a turn-key Winter Park Pine home where everyday life feels like a getaway! From the moment you enter, you will appreciate the home's refined modern aesthetic, clean architectural lines, and thoughtfully curated finishes. Brand new flooring creates a seamless sense of elegance throughout, while sleek new cabinetry, contemporary finishes, and new premium appliances, and new quartz counters is suited for dinning or entertaining! Through sliding glass doors lies the crown jewel: a sparkling, screened in-ground pool surrounded by a luxury private patio! Spend time hosting barbecues under the covered lanai or relaxing in the warm afternoon sun! Yard is fully fenced! Private backyard featuring a plenty sitting areas and a brand-new fire pit for wonderful outdoor gatherings! Whether you are doing morning exercise or watching the sunset by the water, it delivers a peaceful resort living! Living in this renown Winter Park Pine neighborhood with No HOA, yet easy access to golf courses, biking trails and parks, community amenities, Advent hospital, Park Ave, Rollin College and Baldwin Park! Renown school districts and convenient locations! Don't miss out on this rare find—call now to see it in person!

274 N Ranger Boulevard, Winter Park

$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

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