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$675,000
5 Beds ⋅ 4 Baths ⋅ VAWI2010072 MLS ⋅ CLOSED Status
Nestled in the heart of Winchester's cherished historic district, this enchanting circa 1928 cottage blends timeless charm with exceptional opportunity. Rich in character and architectural detail, the home showcases the craftsmanship of a bygone era - warm hardwood floors, inviting living spaces, and distinctive period touches that create an atmosphere both welcoming and refined. The home's vintage appeal offers the perfect canvas for thoughtful updates while preserving its historic integrity. A rare and valuable offering, the price includes an additional buildable lot, providing endless possibilities for expansion, new construction, investment potential, or a private garden retreat in one of the city's most desirable locations. Just moments from Old Town's vibrant shops, dining and cultural attractions, this property presents a unique opportunity to own a piece of history with room to grow in Winchester's most sought-after neighborhoods. Both lots are zoned HR-!

200 & 210 W Fairfax Lane, Winchester
$1,025,000
5 Beds ⋅ 6 Baths ⋅ VAWI2007546 MLS ⋅ CLOSED Status
This circa 1863 Italianate home is located in the heart of Winchester's historic district within a short walk to Handley Library and downtown. The home has been elegantly restored, blending timeless charm with modern comforts. The interior is restored to its original grandeur with high ceilings, hardwood floors, decorative moldings, and fireplaces in every room. Fully updated gourmet kitchen with a breakfast room and large mudroom conveniently located next to the back door. The comfortable layout ensures the house is suitable for contemporary living while preserving its historical charm. The primary bedroom boasts a huge closet(not typical for an older house). The covered patio enhances gracious outdoor living. Separate courtyard and level yard. Off-street parking and a garage! Another real rarity in an older home is the finished basement. Yes, all five of the family members graduated from UVA, which explains the decorating theme of the rec room. The home's historical significance adds to its appeal, offering a unique piece of history and a sense of character that is difficult to find in modern homes.

331 N Braddock Street, Winchester
$685,000
5 Beds ⋅ 5 Baths ⋅ VAWI2007840 MLS ⋅ CLOSED Status
Discover unparalleled charm and historic elegance in this circa 1900 Victorian residence, ideally situated in Winchester's downtown Historic District and on the Apple Blossom parade route. Stunning 5-bedroom,4.5 bathroom home, boasting approximately 4270 sq ft of living space, invites you to experience the grandeur of a bygone era. Off-street parking. Key features include: Historic Charm: Original details abound, from hardwood floors and moldings to elegant fireplaces, offering a true sense of Victorian craftsmanship. Spacious living: Generous room sizes provide ample space for entertaining, family gatherings and comfortable everyday living. Prime Location: Enjoy the absolute best of Winchester downtown living. Stroll to the vibrant Old Town Walking Mall and host gatherings for two Apple Blossom parades! Architectural Beauty: A stately all brick exterior and classic front porch make this home a true standout on one of Winchester's most pictreque streets.

503 S Washington Street, Winchester
$300,000
4 Beds ⋅ 3 Baths ⋅ VAWI2005738 MLS ⋅ CLOSED Status
Unlock the Potential of This Timeless Gem! Nestled in the heart of Winchester, this charming home is a rare opportunity for those with a vision for restoration and a love for history. Built in the early 1800s by Thomas McCune, this home is one of the remaining log structures on record within the Historic District. Key Features:•Historic Charm: Original hardwood floors & logs, detailed moldings, and vintage fixtures offer a glimpse into the past, waiting to be lovingly restored. Featured in “What I Know About Winchester”, “The Story of One Hundred Old Homes in Winchester, VA, “Interior Woodwork of Winchester, VA, “A Prominent Place” •Spacious Layout: With 4 bedrooms and 2 and 1.5 bathrooms, the generous floor plan provides ample space for customization and modern updates.•Prime Location: Situated in a sought-after historic district along the Apple Blossom Parade Route, this home is within walking distance to charming shops, renowned restaurants, and vibrant cultural landmarks.•Investment Potential: Perfect for investors or DIY enthusiasts looking to add significant value through renovations and restorations.•Outdoor Space: A sizable lot offering the perfect backdrop for outdoor entertaining and gardening. Whether you’re drawn to the idea of preserving history or creating a unique blend of old and new this property offers endless possibilities! Don’t miss it! Schedule a viewing today!

121 N Washington Street, Winchester
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Historic District Homes For Sale In Winchester City