Winter Park Pines Rep Homes with Sidewalk Exterior Features

Winter Park Pines Rep Homes with Sidewalk Exterior Features

Welcome to Winter Park Pines Rep, a charming subdivision nestled in the heart of Winter Park, Florida. Known for its picturesque tree-lined streets and friendly atmosphere, this community offers a perfect blend of suburban tranquility and vibrant city life. With its prime location in Orange County, residents enjoy easy access to the best that Winter Park has to offer, including boutique shopping, fine dining, and a variety of cultural attractions.

One of the standout features of Winter Park Pines Rep is the stunning homes that grace its streets. Each residence boasts delightful exterior features, including well-maintained sidewalks that invite leisurely strolls and promote a sense of community. Imagine taking an evening walk with your family or catching up with neighbors as you enjoy the lush landscaping and charming architecture that defines this subdivision.

The homes in Winter Park Pines Rep are designed with both comfort and style in mind. Many properties feature spacious layouts, modern amenities, and inviting outdoor spaces that are perfect for entertaining or simply enjoying the beautiful Florida weather. Whether you’re a first-time homebuyer or looking to downsize, this subdivision offers a range of options to fit your lifestyle.

In addition to its beautiful homes and welcoming community, Winter Park Pines Rep is conveniently located near top-rated schools, parks, and recreational facilities, making it an ideal choice for families. Experience the warmth and charm of Winter Park Pines Rep—where every day feels like a vacation in your own backyard. Come discover your dream home in this enchanting neighborhood today!

Newest Winter Park Pines Rep Homes with Sidewalk Exterior Features

$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
$669,000
4 Beds ⋅ 2 Baths ⋅ O6427246 MLS
Virtually Staged. Welcome to a residence where timeless design meets modern sophistication in the highly sought-after Winter Park Pines community—one of Winter Park's most established neighborhoods, celebrated for its tree-lined streets, oversized homesites, exceptional schools, and proximity to world-class dining, shopping, golf, and cultural attractions. With no HOA, this thoughtfully renovated home offers the perfect balance of refined living and everyday comfort in one of Central Florida's most desirable locations. This 1,605 sqft, 4-bedroom, 2-bath residence, has been transformed with modern finishes, upgraded systems, and thoughtful design throughout. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a bright and inviting space ideal for both everyday living and entertaining. The interior features new luxury vinyl flooring in all main areas and fully remodeled bathrooms with floor and wall tile, elongated modern toilets, updated vanities, and premium finishes. The main bathroom includes a new bathtub, medicine cabinet, and mirror cabinet, while the master bathroom offers a glass-walled shower with a niche and a double floating vanity with mirrored cabinets. The kitchen is a true centerpiece, showcasing a large island, quartz countertops, high-end custom cabinetry with soft-close drawers, and a pantry with built-in shelving. Luxury FORNO white-and-gold appliances elevate the space, including an induction cooktop and range, hood fan, double-door refrigerator with ice maker, and a microwave built into an island drawer. The kitchen is completed with a high-end white sink bowl and garbage disposal, adding both style and functionality. Major improvements were completed with permits, including new HVAC (2026), new water heater (2026), new 200 Amps electrical panel (2026), and a full plumbing repipe (2026). Additional upgrades include new wired smoke alarms and new doors throughout. The living room features modern potlights, and all bedrooms include contemporary ceiling fans. The lanai has been renovated, offering a comfortable outdoor retreat. Exterior enhancements include an updated roof (2020), fresh interior and exterior paint, a refinished garage floor, and an upgraded garage door opener (2026). The property also features a brand-new irrigation system (2026) to keep the grounds lush and easy to maintain. Smart-home additions include a smart Blink doorbell and a smart front-door lock, providing added convenience and security. The spacious, fully-fenced backyard offers privacy and endless possibilities for outdoor enjoyment, gardening, or future enhancements. Perfectly positioned just minutes from Winter Park Pines Golf Club, Cady Way Trail, Park Avenue, Rollins College, AdventHealth Winter Park, and the boutiques, fine dining, and cafés that have made Winter Park one of Central Florida's most coveted destinations, you'll also enjoy convenient access to Downtown Orlando, Baldwin Park, major highways, Orlando International Airport, and countless entertainment venues. With meticulous renovations, modern systems, smart-home upgrades, and an unbeatable Winter Park Pines location, this home is truly move-in ready and prepared to welcome its next owner.

2833 Prince John Road, Winter Park
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