Historic Winchester Homes for Sale

Welcome to Historic Winchester, Virginia – a captivating blend of rich heritage and modern living. Nestled in the heart of Winchester City, this charming subdivision offers a unique opportunity to immerse yourself in a community steeped in history while enjoying the conveniences of contemporary life.

As one of the oldest towns in the Shenandoah Valley, Historic Winchester boasts an array of beautifully preserved buildings and landmarks that tell the story of our nation’s past. Stroll through the picturesque streets lined with quaint shops, delightful cafes, and vibrant public spaces. The renowned Old Town, with its cobblestone streets and historic architecture, is perfect for leisurely walks, local art festivals, and farmers' markets that showcase the best of Virginia’s produce.

For those seeking a new home, Historic Winchester presents an enticing selection of homes for sale. From charming Victorian houses to modern townhomes, there’s something to suit every taste and lifestyle. Many of these residences feature spacious layouts, updated amenities, and beautifully landscaped yards, making them ideal for families, retirees, or anyone looking to enjoy the tranquility of suburban living.

In addition to its historical charm, Historic Winchester is conveniently located near excellent schools, parks, and recreational facilities, ensuring that residents have access to everything they need. With its friendly atmosphere and strong sense of community, Historic Winchester is not just a place to live; it’s a place to call home. Don’t miss the chance to explore the homes for sale in this enchanting subdivision – your dream home awaits!

Newest Historic Winchester Homes for Sale

$699,000

4 Beds ⋅ 3 Baths

432 North Loudoun Street sits a half block up from the historic fort and 2 blocks from the Winchester Mall. This completely redeveloped 1915 Craftsman style house in Winchester’s emerging historic district masterfully combines modern purpose with a classic feel using a sustainable redevelopment design. It is a custom home within a historical exterior, offering all the experiences of new construction. This is a high-quality residence for building your life with its 4 bedrooms, 2 ½ bath, dual street access, including a full fenced-in yard with landscaped patio, hot tub, and 10x8 shed. The floor plan is built around original hand-scraped hardwoods, handcrafted Craftsman style door moldings, an abundance of windows, period staircases, and a stunning new main bedroom/kitchen/family room addition to name a few of the fine features. Upstairs has the owner suite with walk-in closet and full bathroom; additional features include two bedrooms, a wired office, laundry center, and full bath. Presenting wide-ranging features from the mahogany front porch to the custom-built basement staircase to the new addition owner’s suite 432 Loudoun showcases quality is a requirement not a luxury.

432 N Loudoun St, Winchester

Listing courtesy of The Greene Realty Group. Contact:

$749,000

4 Beds ⋅ 4 Baths

Downtown living at its finest! Welcome to 220 Amherst Street, a stunning brick residence nestled in Winchester’s prestigious historic district. This home blends timeless architectural charm with an unbeatable location just steps from downtown dining, boutique shopping, top-rated schools, parks, and the medical center. Classic historic character greets you at the curb, framed by a wrought-iron fenced front yard and a classic brick driveway leading to a rare detached garage featuring a brand-new roof. Step inside to discover gleaming hardwood floors, crisp wainscoting, and detailed crown molding throughout the main living areas. The main level offers a flexible layout that includes a full bathroom, a formal living room anchored by a wood-burning fireplace, an adjoining sitting room, and an elegant formal dining room. The modern kitchen features a sleek subway tile backsplash, stainless steel appliances, a large walk-in pantry, and a cozy breakfast area with built-in seating. Sunlit wooden stairs under overhead skylights lead to the light-filled second level. The spacious primary suite serves as a private retreat with its magnificently renovated ensuite bath—complete with double-sinks, upgraded countertops, a separate tub and walk-in shower, subway tile accents, and custom mosaic flooring. Two additional generous bedrooms and another recently updated full bath share this floor alongside a versatile updated sunroom. Fitted with wall-to-wall windows and its own newer mini-split system for climate control, the sunroom opens directly onto an open deck perfect for catching the morning sun. Up on the top floor, a finished attic provides versatile living space with built-ins and fresh carpet, offering flexible space ideal for a home office, playroom, or media center. The extensive living space continues into the finished basement with durable tile floors and an awesome recreation room highlighted by a second wood-burning fireplace, built-ins, and ample closet space. The basement also includes a cedar-lined closet, dedicated laundry facilities, another full bath, and abundant extra storage space. Outdoors, the backyard sanctuary is fully enclosed with a newer privacy fence and thoughtfully equipped for outdoor leisure, boasting a screened-in porch, raised garden beds, a charming trellis pergola with a dedicated play area, and unmatched privacy right in the heart of town. Complete with a new HVAC system, this move-in-ready historic gem delivers the ideal balance of classic elegance and modern comfort.

220 Amherst St, Winchester

Listing courtesy of Colony Realty. Contact:

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