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$349,990
3 Beds ⋅ 1 Baths ⋅ VAWI2010814 MLS ⋅ CLOSED Status
Expect a long love affair with this home. Some homes feel like they were built with patience, pride, and a sense of permanence—and this historic Winchester beauty has that feeling the moment you step inside. Set near Old Town Winchester and positioned right next to the approved Cider Hill Neighborhood Design District, it offers something rare: preserved historic character today, with a front-row seat to one of Winchester’s most exciting visions for tomorrow. Inside, tall ceilings give the rooms an airy, gracious presence, while the preserved woodwork around the door frames and staircases brings in the kind of craftsmanship that is nearly impossible to recreate. Every doorway feels intentional. Every turn of the staircase reminds you this home has a story. Even better, the home features two staircases, plus an additional staircase leading to the attic—an uncommon old-house detail that adds character, convenience, and intriguing future flexibility. The attic offers potential for a finished loft or creative bonus space later, subject to buyer due diligence, permits, and approvals. With 3 bedrooms and 1 full bath, the home feels warm, grounded, and refreshingly authentic—never cookie-cutter, never stripped of its soul. The kitchen has been refreshed with new drywall and pendant lighting in 2026, adding a clean, current touch while still letting the home’s original personality shine. The bathroom was recently remodeled in 2026, electrical has been updated, new plumbing pipes were run in 2024, and the windows have been replaced within the last three years. The roof was replaced in 2021, the upstairs HVAC was replaced in 2019, and a new hot water heater was installed in 2026. These are the improvements that matter: the ones that help you enjoy the tall ceilings, old-house texture, and beautiful woodwork with added confidence. The back of the home is just as inviting. Dual rear porches create two easy places to start the morning, wind down in the evening, or enjoy the backyard from a shaded perch. Beyond them, a generous 20 by 20 patio gives you room for outdoor dining, container gardens, a firepit setup, or a relaxed weekend gathering space. The flat lot keeps the yard practical and flexible, with open space that feels simple to use and easy to enjoy. The location is where this home becomes especially compelling. Old Town Winchester is known for its local dining, shopping, events, museums, and attractions, giving the surrounding area a lively historic-downtown feel. First Fridays bring local artists, live music, sip-and-stroll energy, and special events to the heart of Old Town. Jim Barnett Park adds more than 170 acres of green space and amenities, while the Museum of the Shenandoah Valley offers galleries, gardens, and daily trail access. Then add Cider Hill. The City of Winchester describes the Cider Hill Neighborhood Design District as an approved future vision focused on revitalizing a historically industrial area into a vibrant mixed-use community through adaptive reuse, enhanced connectivity, and a balance of residential, commercial, and public spaces. In plain language, that means this home is positioned beside an area planned to become more active, more connected, and more useful over time—placing it in the middle of several attractive Winchester destinations as the district evolves. That combination is hard to duplicate: historic architecture, meaningful updates, outdoor living, a flat backyard, proximity to Old Town, adjacency to a planned mixed-use district, two staircases, and attic access with future upside. This is not a house trying to look historic. It is the real thing, with height, texture, craftsmanship, porches, and practical improvements already in place. For anyone hoping to find a home with genuine old-house warmth near Winchester’s historic core—and near a city-backed district with a bold future vision—this one is easy to love and hard to forget. Owner is an inactive Virginia realtor.

519 Fairmont Avenue, Winchester
$675,000
3 Beds ⋅ 3 Baths ⋅ VAWI2010276 MLS ⋅ ACTIVE Status
100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025! This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic Winchester Award of Merit, this home showcases exceptional craftsmanship and dedication to preserving its character while delivering today’s comforts. Major improvements include all-new electrical, plumbing, and ductwork, along with professionally engineered structural reinforcements for long-term integrity and peace of mind. Inside, you’ll find two brand-new HVAC systems, energy-efficient windows and doors, and beautifully refinished original hardwood floors throughout. The designer kitchen features granite countertops and a custom slide-up serving window that opens to a stylish outdoor bar—perfect for entertaining. Bathrooms offer elegant tile finishes and a jetted tub for a spa-like retreat. Custom details such as barn doors, solid wood interior doors, and upgraded lighting elevate the home’s unique character. The exterior is equally impressive, featuring a custom front door, welcoming new front porch, vinyl privacy fencing, a freshly seeded backyard, and a slate patio accented with ambient string lighting. A cobblestone driveway provides two off-street parking spaces—an added luxury in this walkable downtown location. A rare opportunity to own a one-of-a-kind home that perfectly balances historic appeal, modern efficiency, and exceptional craftsmanship in one of Winchester’s most desirable neighborhoods.

112 W Germain St, Winchester
$819,900
4 Beds ⋅ 4 Baths ⋅ VAWI2008914 MLS ⋅ CLOSED Status
Professional photos coming soon! , Best location in the city ! Nestled on a prime corner of the Apple blossom parade route, in a charming close-knit neighborhood , this exquisite Colonial-style residence, built in 1920, seamlessly blends timeless elegance with modern comforts. The exterior, crafted from durable brick, exudes a warm and inviting presence. The meticulously maintained grounds feature lush greenery, while the inviting patio offers a perfect setting under the new pavilion (just added in 2025) for al fresco dining or quiet evenings under the stars. Step inside to discover a thoughtfully designed interior that radiates comfort and style. The home boasts four spacious bedrooms and three and a half luxurious bathrooms, providing ample space for relaxation and privacy. The heart of the home is the cozy living area, where a stunning gas fireplace with glass doors serves as a focal point (gas logs installed 2025), inviting you to unwind in its warm glow during cooler evenings. The partially finished basement, offers a full bath and additional space for a home gym, office, or recreation area, catering to your lifestyle needs. The beautiful windows allow natural light to flood the interior, creating a bright and airy atmosphere throughout. This property is a true gem, offering a unique blend of historic charm and modern luxury, perfect for those seeking an exclusive lifestyle in a serene setting. Experience the comfort and elegance that this home has to offer, where every detail has been carefully curated to create a sanctuary you will be proud to call your own. Recent Upgrades include water treatment system, Washer/Dryer, built in Microwave, Refrigerator, Dishwasher, extensive plumbing upgrades, gas logs, basement sump pump, outdoor pavilion, 2 HVAC systems

700 S Stewart Street, Winchester
$814,000
4 Beds ⋅ 4 Baths ⋅ VAWI2006566 MLS ⋅ CLOSED Status
The "Long House" circa 1785 located in downtown Winchester Historic District. This federal-style home was renovated in 2005 by renowned local architect Fred Andreae for the current owners. Larger rooms with hardwood floors. French doors from the dining room open to an inviting brick and flagstone patio. Small garden, Viburnum, magnolia, boxwood, and old lilac create a perfect place for entertaining. The library addition is extremely comfortable and the primary bedroom and bath offer modern amenities. Large walk-in closet. Apple Blossom parade route.

101 N Washington Street, Winchester
$1,325,000
7 Beds ⋅ 6 Baths ⋅ VAWI2005476 MLS ⋅ CLOSED Status
Sitting atop a knoll overlooking the city sits Selma Mansion, Winchester's Crown Jewel. From your entry through the private gate you wind up the driveway through Selma's 4.15 acre campus, past the grass amphitheater, to this commanding home, boasting 7 bedrooms, 4 bathrooms, and 2 half baths. Walk up the dramatic front brick steps into the foyer which takes your breath away with its dramatic scale and ornate detail and windows ushering in natural light. Selma's gracious and dramatic rooms set the scene for a lifetime of memories with a backdrop of unsurpassed elegance reminiscent of a bygone era. A grand ballroom runs the length of the home, flanked by dual carved Italian marble fireplaces on each end, floor-to-ceiling and bay windows, and windows which open to step out to a large entertaining porch. Selma's Dining room seats up to 30 guests and walks through 12' pocket doors to a breathtaking parlor and sunroom. To the rear of the house sits a large kitchen, breakfast room and wood paneled library. Step outside to multiple porches including a two-story sleeping porch screened on the upper level. Enjoy the bustle of downtown Winchester and retreat to your private sanctuary, one mile from Winchester Medical Center and 75 miles west of Washington D.C. Selma awaits its next steward and offers a once-in-a-lifetime opportunity to own this rare historic masterpiece.

514 Amherst Street, Winchester