Winter Park Pines Rep Homes for Sale

Winter Park Pines Rep Homes for Sale

Welcome to Winter Park Pines Rep., a charming subdivision nestled in the heart of Winter Park, Florida, within the vibrant Orange County. This delightful community is renowned for its picturesque tree-lined streets, friendly atmosphere, and a perfect blend of suburban tranquility and urban convenience.

Winter Park Pines Rep. offers a diverse selection of homes for sale, catering to a variety of lifestyles and preferences. From cozy single-family residences to modern townhomes, each property is designed with comfort and style in mind. Many homes feature spacious yards, ideal for family gatherings or quiet evenings under the stars. With well-maintained landscaping and a welcoming ambiance, you’ll feel right at home from the moment you arrive.

Residents of Winter Park Pines Rep. enjoy easy access to an array of amenities. Just a short drive away, you’ll find the bustling downtown Winter Park, filled with boutique shops, gourmet restaurants, and cultural attractions such as the renowned Morse Museum of American Art. Outdoor enthusiasts will appreciate the nearby parks and recreational facilities, providing ample opportunities for hiking, biking, and enjoying Florida’s beautiful weather.

Families will be pleased to know that Winter Park Pines Rep. is served by top-rated schools, making it an ideal location for those looking to settle down and raise children. With its strong sense of community and friendly neighbors, Winter Park Pines Rep. truly embodies the essence of Florida living.

If you’re in the market for a new home, explore the available listings in Winter Park Pines Rep. and discover the perfect place to call your own in this enchanting subdivision!

Newest Winter Park Pines Rep Homes for Sale

$475,000
2 Beds ⋅ 2 Baths ⋅ O6435708 MLS
Welcome to this charming 2 bedroom, 2 bath home, with light and bright open floor plan, spacious rooms and many updates and upgrades. Roof was replaced (2019), new A/C (8/26), fully renovated kitchen with quartz counters, cabinetry, and stainless appliances. Pella double pane windows (2020), new French doors and interior doors, and new soffits and gutters in 2025. Enjoy outdoor living in the lanai overlooking a large fenced backyard with native landscaping. This highly desired neighborhood offers excellent schools, quiet streets, community pool, hiking and biking trails, and nearby public golf course. Live minutes from Advent Hospital, city conveniences, downtown Park Avenue shops and restaurants. Also easy access to neighboring towns, Orlando and airports. This is a perfect starter home or downsize home for those want all the comforts and privacy of a home, neighborhood and community in smaller space and are not ready for an apartment and high HOA fees.

2824 Prince John Road, Winter Park
$494,900
3 Beds ⋅ 2 Baths ⋅ O6415084 MLS
GREAT HOME & GREAT VALUE — home needs cosmetic work and some TLC - if you DIY you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for BROOKSHIRE ELEMENTARY which is 3 blocks away. New roof (12/2021), New water heater (12/2021), Re-piped (1/2022, no polybutylene), New garage door and opener (2/2022), New AC evaporator coil (6/2022) and New French drain system (6/2023). The home has an irrigation system and irrigation well and New gutters (2/2022). OWNER FINANCING available for owners or flippers. All room dimensions must be independently verified by the buyer.

2715 Prince John Road, Winter Park
$614,500
3 Beds ⋅ 2 Baths ⋅ O6387685 MLS
Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning two-tone kitchen is a true centerpiece, featuring sleek quartz countertops, contemporary finishes, and new appliances to be installed at closing—perfect for both everyday living and entertaining. The upgrades continue in the fully renovated bathrooms, where carefully selected color palettes and high-quality finishes provide a fresh, sophisticated look designed to stand the test of time. Every detail of this home has been meticulously considered, leaving no space untouched. Outdoors, enjoy your private oasis with a newly resurfaced pool—ideal for relaxing weekends or hosting gatherings year-round in Florida’s sunshine. This move-in-ready gem offers the perfect opportunity to own a like-new home in a highly desirable location. Come experience the beauty, quality, and lifestyle that 2708 Lion Heart Rd has to offer—your dream home awaits.

2708 Lion Heart Road, Winter Park
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