$502,334Average Value$223Average Price per Sq Ft14Homes For Sale
Middletown attracts commuters and anyone looking for quiet atmosphere
Just south of Winchester is Middletown, a quiet place to live, though the area’s population has grown since home development took off in 2018. “My husband and I moved here in 2017, and the population was 1,500 then,” says Paige Ulevich, broker and partner at Dream Real Estate in Middletown. “It’s creeping up to 3,000, so it’s exploded. The cost of living compared to northern Virginia is so much lower, it's mind-blowing. The median price is about half of northern Virginia’s.” Ulevich attributes Middletown’s growth to its accessibility to Interstates 81 and 66. Middletown residents can relax at small restaurants on Main Street or get involved in community events.
Middletown’s mayor, Charles Harbaugh, is always active in the community and usually helps out at big events. Ulevich organizes events at Belle Grove Plantation. “I run two festivals there a year,” Ulevich says. “If I need him, he’s there. He's been the emcee and poured beer. He always comes and supports us.”
Middletown offers a taste of suburbia surrounded by farmland.
Middletown has a rich history.
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From new construction to farmhouses on sprawling lots
Smaller ranch-style homes and townhouses sell for $250,000 to $400,000. Most new homes and newer Craftsmans sell for $400,000 to $650,000, while Colonial Revivals and farmhouse-style homes on larger lots range from $650,000 to $920,000. Newer communities often feature sidewalks. Many homes have large yards. Farmland surrounds central Middletown, and properties on the outskirts tend to have sprawling lots and plenty of room between neighbors.
Middletown homes sit on acres of land.
Middletown has quiet streets and sidewalks for residents to explore surburbia.
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Easy interstate access to northern Virginia and D.C.
“It’s really easy to be a commuter in Middletown,” Ulevich says. “I-66 goes to Washington, D.C., and I-81 goes up to New York and down to the Gulf. There are people who commute to Winchester, but you’d be surprised at how many people commute into northern Virginia and D.C.” Winchester is 15 miles north of the area when using I-66. Middletown is about 80 miles from D.C. Front Royal commuter buses run from Middletown to D.C. Some commuters use carpool services to travel along high-occupancy toll lanes. There’s a Valley Health Urgent Care Express in Strasburg and Front Valley, but the nearest hospital is the Winchester Medical Center. Although it is not open to the public, St. Thomas Episcopal Church is a historic place of worship among the other churches in town. It was built in 1834, used as a hospital during the Battle of Cedar Creek in 1864, and now hosts the occasional church service or weddings.
The community rallied to keep tradition alive at Sherando High
Students can attend Middletown Elementary School, which gets a B-minus from Niche. Robert E. Ayler Middle is closer to Winchester and also receives a B-minus. The B-plus rated Sherando High School has a tradition, where every football game starts with its mascot, a Native American warrior, riding onto the field and throwing a spear into the ground. The school had no horse in 2024 and almost had to end the tradition, but the community raised enough funds to purchase a new horse. Laurel Ridge Community College is in Middletown and gets a C-plus. Laurel Ridge Community College is in Middletown and gets a C-plus. Students can apply for the college's associate degree or dual-enrollment program.
Students start off at Middletown Elementary School.
Robert E. Ayler Middle School welcomes students from a variety of different backgrounds.
Students transition to Sherando High School.
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Annual events at Middletown Community Park, national parks nearby
The Middletown Community Park has a playground, walking trail and two baseball fields. It is also the venue for several Middletown events. “The Fourth of July is an all-day celebration, with live music, games, food trucks and parades. Everybody goes back to the park for fireworks," Ulevich says. "At Christmas time, we do a tree lighting on Black Friday. There’s music, Christmas carolers and a Santa.”
The Cedar Creek and Belle Grove National Historical Park features historic buildings open for tours, the Cedar Creek Battlefield and visitor centers. Shenandoah National Park is close to Middletown. Residents can drive 18 miles to the Dickey Ridge Visitor Center before setting off on the Fox Hollow Trail. Kayakers and anglers can also float down the Shenandoah River.
Middletown Community park welcomes all residents.
Middletown Community Park offers a playground to children.
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Popular restaurants on Main Street, with shopping in Fort Royal
Middletown has a few restaurants along Main Street. “Vault and Cellar opened a few years ago,” Ulevich says. “It’s received national attention for the chef’s cuisine, and they have over 100 bourbons. They do an amazing brunch.” Shaffer's BBQ & Market uses locally sourced products for menu items, such as Brunswick stew and brisket sandwiches. Residents who need groceries might drive down U.S. Route 11 to the Food Lion in Strasburg or take I-66 to shop at the Target or Walmart Supercenter in Fort Royal.
Shaffer's BBQ & Market is the go to spot for great food.
Vault & Cellar invites guests to enjoy their menu.
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Written By
Rylee Doyle
Photography Contributed By
Aiyshanti Green
Video By
Bob Yukich
Interested in learning more about homes in this area?
Reach out to
Paul Gallagher,
an experienced agent in this area.
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Cedar Creek & Belle Grove National Historical Park Visitors Contact Station
Middletown Housing Trends
On average, homes in Middletown, VA sell after 57 days on the market compared to the national average of 56 days. The median sale price for homes in Middletown, VA over the last 12 months is $479,999, up 3% from the median home sale price over the previous 12 months.
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