The five highest-priced home sales reported in Northern Shenandoah Valley, Virginia for the week ending October 25, 2026 added up to $4.06 million. All five were single-family homes, and the list split between land and neighborhood living: a Craftsman home on more than 13 acres in Strasburg and a Colonial on just over 20 acres in Middletown led the way, followed by three Winchester homes in Hunting Ridge Estates, Abrams Pointe and Raven Pointe.
The group spans nearly three decades of building, from a home finished in 1998 to a new-construction Craftsman completed this year.
No. 1 — $1,000,000 · 2612 Coal Mine Rd, Strasburg, Virginia
The week’s top sale is a single-story Craftsman home on 13.36 wooded acres in Strasburg, with roughly 763 feet of frontage on Cedar Creek. A path leads through the property to the creek, and a scenic overlook takes in a view toward the water. The setting is rural and secluded, with trees at the back of a level lot.
Built in 1998 and finished in board-and-batten siding, the home has three bedrooms, three full baths and a half bath, and 4,011 square feet of living space, the most of the five. The primary suite is on the main level, and its bath has a clawfoot tub, a steam shower and a separate walk-in shower. The kitchen has granite countertops, an eight-burner gas cooktop and space for an eat-in table. The home has two fireplaces, a full finished basement, whole-house audio and a central vacuum system.
Outdoor living is spread among a front porch, a rear patio and a screened porch. A detached three-car garage has a studio apartment above it with a bedroom area, a full bath and a living area. The property is within easy reach of Strasburg, Winchester and I-81, and it last sold for $515,000 in 2004.
The home went under contract 25 days after it was listed and sold for $1 million, its full asking price. Abby Walters of Preslee Real Estate was the listing agent, and drew price of Realty FC, LLC represented the buyer in the week’s highest-priced sale.
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No. 2 — $825,500 · 354 Guard Hill Rd, Middletown, Virginia
At 20.14 acres, the No. 2 sale in Middletown came with the most land of the five. The property is zoned for agriculture and set up to use it: a newly built barn, a chicken coop, a private pond and several outbuildings with water spigots, along with a detached workshop measuring 30 by 50 feet with 14-foot ceilings.
The Colonial home was built in 2017 as a custom home. It has four bedrooms, three baths and 2,840 square feet, with vaulted ceilings, hardwood floors and an open plan that draws plenty of daylight. The kitchen has an oversized island and a pot filler. On the main level, a bedroom with an adjoining full bath now serves as an office, and the laundry is on that floor as well. Several of the bedrooms have their own baths. The home has one fireplace and an attached two-car garage, and the location offers easy access to both I-66 and I-81.
The property last sold for $479,900 in 2020. This time it went under contract 15 days after it was listed and sold for $825,500, just above its $825,000 asking price. Steven Leach of Keller Williams Realty was the listing agent, and Kimberlee Wergland of Realty ONE Group Old Towne represented the buyer.
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No. 3 — $800,000 · 250 Creola Dr, Winchester, Virginia
In Hunting Ridge Estates in Winchester, the No. 3 sale is a ranch-style home built in 2022 on 3.54 private, wooded acres. The property last sold for $86,000 in 2021, before the current house was built.
The home’s 2,484 square feet, the least of the five, are arranged around an open great room with a wood-burning stone fireplace that leads into a large kitchen with an island. All three bedrooms are on the main level in a split plan that sets the primary suite apart. The second and third bedrooms each have their own bath. A covered, screened porch looks out over the woods, and below the main floor is a full unfinished basement with a rear entrance and plumbing roughed in for a future bath. An attached two-car garage faces the side.
The home went under contract 21 days after it was listed and sold for $800,000. Curtis Siever of NextHome Realty Select was the listing agent, and Stephanie Feltner of Realty ONE Group Old Towne represented the buyer.
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No. 4 — $720,000 · 154 Williamson Rd, Winchester, Virginia
The newest home on the list is a three-story Craftsman completed in 2026 in Abrams Pointe, a new community of single-family homes within an established Winchester neighborhood. Built to the builder’s Carlisle plan, it sits on 0.28 acres, the smallest lot of the five, with views of the mountains and the woods.
The home has six bedrooms, the most of the group, along with five full baths, two half baths and 3,365 square feet. The exterior combines vinyl siding with brick and stone. Inside, an open kitchen with a large island and a walk-in pantry runs into a breakfast area and a great room, and a flex room at the front can work as an office, a playroom or a formal living room. One bedroom is on the main level, the basement is partially finished with both inside and outside entrances, and the attached two-car garage faces the front.
The new home sold for $720,000. Greta Fernandez of New Home Star Virginia, LLC was the listing agent, and Kathie Gregg of Braddock Realty Inc represented the buyer.
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No. 5 — $715,000 · 107 Cahille Dr, Winchester, Virginia
The backyard sets apart the No. 5 sale, a 2006 Colonial in Winchester’s Raven Pointe subdivision. A heated saltwater pool measuring 20 by 40 feet has a tanning ledge, a sunken spa and an automatic safety cover, and a covered Trex deck with a porch swing looks over the private yard. Stone retaining walls and extensive hardscaping frame the landscaped 0.38-acre lot, and the neighborhood has sidewalks and streetlights.
The brick and vinyl home has four bedrooms, three full baths and a half bath, and 3,757 square feet over three levels. The main floor has a home office with custom built-ins, a dining room and a family room with a gas fireplace. The kitchen has a large center island, gas cooking, a butler’s pantry and a bright breakfast room. Upstairs, the primary suite has a walk-in closet and a bath with a jetted tub, a walk-in shower and dual vanities, and three more bedrooms share that floor with a bonus room and the laundry. The finished walk-up basement adds a recreation room, a wet bar with an ice maker, a full bath, a storage room and another bonus room.
The property last sold for $470,000 in 2020 and this week sold for $715,000. Laura White of ERA Oakcrest Realty, Inc. was the listing agent, and Justin Mistretta of Berkshire Hathaway HomeServices PenFed Realty represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 25, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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