Winter Park Pines Homes with Pool Community Features

Welcome to Winter Park Pines, a picturesque subdivision nestled in the heart of Winter Park, Florida, within the vibrant Orange County. This charming community is a hidden gem, offering a serene lifestyle while being conveniently close to the bustling amenities of downtown Winter Park. Known for its lush landscapes and friendly atmosphere, Winter Park Pines is the perfect place for families, retirees, and everyone in between.

One of the standout features of Winter Park Pines is its abundance of homes with pools, providing residents with a private oasis right in their backyards. Imagine spending sun-soaked afternoons lounging by your own pool, hosting barbecues, or enjoying a refreshing swim after a long day. The community is designed for relaxation and enjoyment, with many properties featuring spacious outdoor areas perfect for entertaining.

In addition to the luxurious homes, Winter Park Pines boasts a variety of community features that enhance the living experience. Residents can take advantage of beautifully landscaped parks, walking trails, and recreational areas, fostering a sense of community and encouraging outdoor activities. The neighborhood is also known for its excellent schools and proximity to shopping, dining, and cultural attractions, making it an ideal location for those who appreciate both convenience and tranquility.

Whether you're looking for a family home or a peaceful retreat, Winter Park Pines offers a unique blend of comfort and community spirit. Come discover the charm of this delightful subdivision and see why so many choose to call Winter Park Pines home!

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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