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$3,175,000
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
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
$275,000
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