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$3,175,000

A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century charm and contemporary convenience across 8,593 finished square feet, featuring 6 bedrooms, 5 full baths, and 2 half baths. The heart of the residence is the original 1765 portion, which stands as a museum-quality testament to early American craftsmanship. It showcases meticulously preserved original flooring, windows, doors, period hardware, stately mantles, and staircase. As the estate evolved, a first major addition was seamlessly introduced in 1940, followed by a second grand addition in 2000. True to the property's legacy of excellence, the 1940 wing underwent a major, high-end renovation in 2019 to ensure flawless modern style. Yet, behind the historic craftsmanship lies a completely modernized infrastructure: the entire home boasts fully updated plumbing, electrical, and central heating and A/C. Step outside to find your own secluded sanctuary, complete with a natural spring and a picturesque pond. This is a living piece of art, offering the perfect synergy of historical beauty, absolute privacy, and contemporary convenience. For additional information, full ownership history starting in 1735 and comprehensive renovation highlights please view the accompanying documents. Schedule your private tour to experience this once-in-a-lifetime legacy property. See accompanying files for full Historical Lineage starting in 1735, and details about the architecture and features.

6 Beds ⋅ 7 Baths

A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century charm and contemporary convenience across 8,593 finished square feet, featuring 6 bedrooms, 5 full baths, and 2 half baths. The heart of the residence is the original 1765 portion, which stands as a museum-quality testament to early American craftsmanship. It showcases meticulously preserved original flooring, windows, doors, period hardware, stately mantles, and staircase. As the estate evolved, a first major addition was seamlessly introduced in 1940, followed by a second grand addition in 2000. True to the property's legacy of excellence, the 1940 wing underwent a major, high-end renovation in 2019 to ensure flawless modern style. Yet, behind the historic craftsmanship lies a completely modernized infrastructure: the entire home boasts fully updated plumbing, electrical, and central heating and A/C. Step outside to find your own secluded sanctuary, complete with a natural spring and a picturesque pond. This is a living piece of art, offering the perfect synergy of historical beauty, absolute privacy, and contemporary convenience. For additional information, full ownership history starting in 1735 and comprehensive renovation highlights please view the accompanying documents. Schedule your private tour to experience this once-in-a-lifetime legacy property. See accompanying files for full Historical Lineage starting in 1735, and details about the architecture and features.

730 Merrimans Ln, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$350,000

Exceptional investment opportunity in the heart of Winchester! This unique offering includes three income-producing rental units for one price: one duplex and one single-family home located at 211, 213, and 215 E. Clifford Street. The duplex features two separate 2-bedroom, 1-bath units, while the single-family home also offers 2 bedrooms and 1 full bath. The properties are deeded separately as two parcels (tax #193-01-T-9 & 193-01-T-8) , providing added flexibility for future investment strategies. All occupied units are currently rented on month-to-month leases, offering the new owner maximum flexibility to adjust rents, renovate, or continue operating as investment properties. As of the listing date, one unit is vacant, presenting an immediate opportunity to place a new tenant at market rent or occupy the property. Prospective buyers are welcome to drive by and walk the exterior of the properties. Interior showings are by appointment only. Whether you're looking to expand your rental portfolio or invest in a property with immediate income potential and future upside, this is a rare opportunity within Winchester City limits.

211, 213-215 E Clifford St, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360

$539,000

Nestled on one of Winchester's most sought-after streets, this distinctive mid-century contemporary home offers a rare blend of character, space, and convenience just moments from downtown dining, shopping, and entertainment. Designed for comfortable main-level living, the home combines timeless architectural appeal with thoughtful functionality. The main level features a spacious primary suite with an expansive walk-in closet and private en-suite bath. The bright and inviting living room flows seamlessly into the kitchen, complete with granite countertops, abundant cabinetry, and a charming pass-through to the separate dining area. Just off the kitchen, you'll find a conveniently located laundry area with additional cabinetry and countertop workspace. Step outside to a private patio, perfect for entertaining or relaxing after an evening downtown. A fenced side yard provides additional outdoor space for pets, gardening, or play. Upstairs, an open loft creates the perfect reading nook, home office, or cozy sitting area, alongside two additional bedrooms and a full bath. The expansive partially finished basement provides exceptional flexibility, featuring a bonus room, full bathroom, second laundry area, and abundant storage, with plenty of room for future customization. Combining architectural character, flexible living spaces, and an exceptional location, this home presents a unique opportunity in the heart of Winchester.

3 Beds ⋅ 4 Baths

Nestled on one of Winchester's most sought-after streets, this distinctive mid-century contemporary home offers a rare blend of character, space, and convenience just moments from downtown dining, shopping, and entertainment. Designed for comfortable main-level living, the home combines timeless architectural appeal with thoughtful functionality. The main level features a spacious primary suite with an expansive walk-in closet and private en-suite bath. The bright and inviting living room flows seamlessly into the kitchen, complete with granite countertops, abundant cabinetry, and a charming pass-through to the separate dining area. Just off the kitchen, you'll find a conveniently located laundry area with additional cabinetry and countertop workspace. Step outside to a private patio, perfect for entertaining or relaxing after an evening downtown. A fenced side yard provides additional outdoor space for pets, gardening, or play. Upstairs, an open loft creates the perfect reading nook, home office, or cozy sitting area, alongside two additional bedrooms and a full bath. The expansive partially finished basement provides exceptional flexibility, featuring a bonus room, full bathroom, second laundry area, and abundant storage, with plenty of room for future customization. Combining architectural character, flexible living spaces, and an exceptional location, this home presents a unique opportunity in the heart of Winchester.

1202 Handley Ave, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475

$369,000

🏡 **Excellent Opportunity in the Heart of Winchester!** Don't miss the chance to own a well-located home in one of Winchester's most convenient areas. Situated on a quiet street, this property offers easy access to shopping, dining, schools, parks, and major commuter routes—everything that matters is just minutes away. Featuring **3 bedrooms** plus **two additional versatile rooms**, this home provides the flexibility to fit your lifestyle. Whether you need a home office, guest room, gym, playroom, hobby space, or additional storage, the possibilities are endless. Schedule your showing today and discover the potential this Winchester home has to offer! 🏠✨

3 Beds ⋅ 3 Baths

🏡 **Excellent Opportunity in the Heart of Winchester!** Don't miss the chance to own a well-located home in one of Winchester's most convenient areas. Situated on a quiet street, this property offers easy access to shopping, dining, schools, parks, and major commuter routes—everything that matters is just minutes away. Featuring **3 bedrooms** plus **two additional versatile rooms**, this home provides the flexibility to fit your lifestyle. Whether you need a home office, guest room, gym, playroom, hobby space, or additional storage, the possibilities are endless. Schedule your showing today and discover the potential this Winchester home has to offer! 🏠✨

614 Sherlock Trce, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911

$325,000

This is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/Cooper Mill) is available. The Mill was constructed during the years 1812-1815. At the base, the structure has stone walls that are 3' thick, tapering to about half that at the gable ends. The Mill has a "mechanics level", the lower level with dirt floor and water source when the Grist wheel was in place. The next two levels are wide open with wood floors and open beams. There are also stairs to attic space on the very upper level. The attached "miller's house" was added several decades later. Still quite livable with original wood floors, formal living and dining rooms, and bedroom(s), bath, upstairs. The interesting features remain. The Mill office is off the living room, where the original wood burning fireplace remains. The house has a covered front porch, and rear upper and lower covered porches. The grounds are quite nice with an array of plantings and a path/walking bridge over Opequon Creek. This property is at the corner of Cedar Creek Grade and Miller Road. Inquire about information relating to Deed of Gift Easement with Historical. NEW SEPTIC JUST INSTALLED. Price just reduced. The Seller is ready to sell!!

3 Beds ⋅ 2 Baths

This is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/Cooper Mill) is available. The Mill was constructed during the years 1812-1815. At the base, the structure has stone walls that are 3' thick, tapering to about half that at the gable ends. The Mill has a "mechanics level", the lower level with dirt floor and water source when the Grist wheel was in place. The next two levels are wide open with wood floors and open beams. There are also stairs to attic space on the very upper level. The attached "miller's house" was added several decades later. Still quite livable with original wood floors, formal living and dining rooms, and bedroom(s), bath, upstairs. The interesting features remain. The Mill office is off the living room, where the original wood burning fireplace remains. The house has a covered front porch, and rear upper and lower covered porches. The grounds are quite nice with an array of plantings and a path/walking bridge over Opequon Creek. This property is at the corner of Cedar Creek Grade and Miller Road. Inquire about information relating to Deed of Gift Easement with Historical. NEW SEPTIC JUST INSTALLED. Price just reduced. The Seller is ready to sell!!

2431 Cedar Creek Grade, Winchester

Listing courtesy of Cedar Creek Real Estate. Contact:

$275,000

Back on the Market!...Beautifully located in the heart of Historic Winchester, this charming home offers 2 bedrooms, 1 full bath, and a versatile bonus room on the second floor-perfect for an office, guest space, or hobby room. Enjoy the convenience of being within walking distance to downtown Winchester's shops, restaurants, entertainment, and the famous Apple Blossom Festival festivities. Situated inside of the Historic District, This property combines character, location, and opportunity in one of Winchester's most desirable area. Don't miss this opportunity to own a piece of the Historic Winchester.. SOLD AS IS.

2 Beds ⋅ 1 Baths

Back on the Market!...Beautifully located in the heart of Historic Winchester, this charming home offers 2 bedrooms, 1 full bath, and a versatile bonus room on the second floor-perfect for an office, guest space, or hobby room. Enjoy the convenience of being within walking distance to downtown Winchester's shops, restaurants, entertainment, and the famous Apple Blossom Festival festivities. Situated inside of the Historic District, This property combines character, location, and opportunity in one of Winchester's most desirable area. Don't miss this opportunity to own a piece of the Historic Winchester.. SOLD AS IS.

11 W Germain St, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360

$200,000

4.2 Acres, Sold As-Is, Flat Usable Lot, Partially Wooded, Well and Septic Exists, Just Outside of Winchester VA, No HOA, Unrestricted. Well and septic on property . Well is located in back of old mobile home at water pump. Septic located further back behind old mobile home marked wirh red sparay paint. Health department docs are in bright. Neither house nor mobile home livable. Sold As Is With All personal property and buildings on property

1 Beds ⋅ 1 Baths

4.2 Acres, Sold As-Is, Flat Usable Lot, Partially Wooded, Well and Septic Exists, Just Outside of Winchester VA, No HOA, Unrestricted. Well and septic on property . Well is located in back of old mobile home at water pump. Septic located further back behind old mobile home marked wirh red sparay paint. Health department docs are in bright. Neither house nor mobile home livable. Sold As Is With All personal property and buildings on property

5737 N Frederick Pike, Winchester

Listing courtesy of Coldwell Banker Premier. Contact: 990007.lead@leads.leadrouter.com