Virginia Heights Rep Real Estate

Welcome to Virginia Heights Rep, a hidden gem nestled in the heart of Winter Park, Florida. This charming subdivision offers a unique blend of suburban tranquility and urban convenience, making it an ideal location for families, professionals, and retirees alike.

Virginia Heights Rep is characterized by its tree-lined streets and beautifully maintained homes, exuding a welcoming atmosphere that invites you to explore. The neighborhood is known for its diverse architectural styles, ranging from classic Florida bungalows to modern designs, ensuring that there’s something to suit every taste. With a strong sense of community, residents often come together for neighborhood events, fostering lasting friendships and connections.

One of the standout features of Virginia Heights Rep is its proximity to Winter Park’s vibrant downtown area. Just a short drive away, you’ll find an array of boutique shops, gourmet restaurants, and cultural attractions, including the renowned Charles Hosmer Morse Museum of American Art. Nature enthusiasts will appreciate the nearby parks and lakes, perfect for leisurely strolls, picnics, or a day of kayaking.

Families will benefit from the highly-rated schools in the area, providing excellent educational opportunities for children of all ages. Additionally, Virginia Heights Rep is conveniently located near major highways, making commutes to Orlando and beyond a breeze.

Whether you’re looking to settle down or invest in a piece of Florida paradise, Virginia Heights Rep in Winter Park offers a delightful community with a rich blend of amenities and charm. Come and discover the lifestyle that awaits you in this enchanting subdivision!

Newest Listings in Virginia Heights Rep

$1,025,000

3 Beds ⋅ 3 Baths ⋅ O6420090 MLS ⋅ Virginia Heights BLDG.

Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. NEW TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!

1138 S Pennsylvania Avenue, Winter Park

$1,625,000

4 Beds ⋅ 2 Baths ⋅ O6402113 MLS

A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, ideal for today’s lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with durability and efficiency in mind. Major improvements include a commercial-grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home’s long-term value and performance. The outdoor spaces have been equally curated, with mid-century-inspired landscaping designed for beauty and ease of maintenance. Palms, agave and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances ambiance and function. Just moments from desirable Park Avenue, this architecturally significant modern residence is ideally in one of Winter Park’s sought-after neighborhoods, near Lake Virginia, Rollins College and Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north-facing orientation and beautiful natural light throughout the day.

446 Melrose Avenue, Winter Park

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