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Winchester Real Estate Search

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Winchester Homes and Condos for Sale

Winchester, Virginia is a lovely independent city located in Frederick County. It is the county seat of Frederick County, but the two are separate jurisdictions. Located in the Shenandoah Valley, between the Allegheny Mountains and the Blue Ridge Mountains, the area was originally a Shawnee village. The first settlements were established around 1729 with people who had migrated from Pennsylvania. By 1738 the settlements came to be known as Frederick Town. In 1752 the city was granted a charter and renamed Winchester. During the Civil War, Winchester was a key location for the Confederate States Army. It was the site of several major campaigns, and historians say that Winchester changed hands up to 72 times. Battles along Main Street were not uncommon, and Confederate and Union headquarters were sometimes just one block apart. Military presence remained in Winchester during the Reconstruction. The town continued to recover and grow, and today there are approximately 27,300 people living in Winchester.

Winchester has many offerings that help celebrate its history. The Museum of the Shenandoah Valley is in a plantation home that features a mini-house collection, examples of regional history as well as 18th-century art. The Shenandoah Valley Discovery Museum offers hands-on interactive science as well as cultural, educational opportunities. They also have play opportunities to make education fun. Guided tours through the Thomas J. Jackson Headquarters show the landmark house is full of artifacts from 1861-1862, the time frame the general called the home his headquarters. An additional historical site worth a visit is the Old Court House Civil War Museum. Located in an 1840 building, it offers artifacts and prisoner graffiti in exhibits displaying the wartime role of Winchester. Winchester also boasts a historic log cabin which offers presidential exhibits and was George Washington’s Office.

Winchester real estate offers ranch style single-family homes, traditional two-story homes, split level homes, new contemporary homes, and townhomes. With lovely yards and mature trees, these homes reflect the welcoming atmosphere of Winchester. With the many historic places to visit, the plentiful trails to hike, and the amazing beauty that surrounds Winchester, it’s appeal is obvious. With the highly rated schools, the many unique shops and eateries, this is a must-see destination for homebuyers searching in the northern Virginia area. If you would like more information regarding homes for sale in Winchester, Virginia, please allow us to assist you and contact us today.

Newest Winchester Homes and Condos for Sale

218 Thunder Ridge Ln, Winchester image
218 Thunder Ridge Ln, Winchester $699,000

Welcome HOME! This new home is ready to go! Almost 7 acres less than 10 minutes from Walmart and Winchester Medical! Full finished walkout basement - could be great in-la...

  • 5 Beds
  • 3 Baths
  • VAFV2007620 MLS
Grouse Dr, Winchester image
Grouse Dr, Winchester $299,999

Home is set for completion by September 1, 2022. This classic one level living home is popular for a reason. Tucked away in a peaceful setting and complete with everyth...

  • 3 Beds
  • 2 Baths
  • VAFV2007866 MLS
111 Settlers Cir, Winchester image
111 Settlers Cir, Winchester $424,900

Immaculate Colonial with 4 bedrooms, 2 1/2 baths, in the heart of Pioneer Heights. This home features hardwood floors, an upgraded kitchen with granite countertops and LG...

  • 4 Beds
  • 3 Baths
  • VAFV2007822 MLS
110 Cannon Cir, Winchester image
110 Cannon Cir, Winchester $489,900

“Beauty in the Heights” - Take a close look at this stunning house, where you have plenty of well-cared for custom renovations and improvements to a home in a highly desi...

  • 5 Beds
  • 3 Baths
  • VAFV2007820 MLS
216 Taggart Dr, Winchester image
216 Taggart Dr, Winchester $624,900

This gorgeous one-level home was built by and is owned by coveted, local custom builder, Tony Foreman. His attention to detail shines throughout this home, and its been ...

  • 3 Beds
  • 3 Baths
  • VAFV2007576 MLS
342 Canyon Rd, Winchester image
342 Canyon Rd, Winchester $610,000

Beautiful home located on East side of Winchester in Twin Lakes Overlook. Nice corner large .40 Acre Lot with a side loading garage. Inside you will find a floor to c...

  • 4 Beds
  • 3 Baths
  • VAFV2007238 MLS
208 Jordan Dr, Winchester image
208 Jordan Dr, Winchester $435,000

What a Remarkable Property on a Quaint Street in Jackson Orchard! On a cul dec sac, The land behind is protected (civil war property) so it can never be built on Sup...

  • 3 Beds
  • 3 Baths
  • VAFV2007784 MLS
105 Windmill Ln, Winchester image
105 Windmill Ln, Winchester $285,000

3 Bedroom 2 1/2 BathTownhouse off RT. 7.Close to shopping, medical urgent care, restaurants,and Commuter Routes 7, I81, and 50.

  • 3 Beds
  • 3 Baths
  • VAFV2006670 MLS
4967 Wardensville Grade, Winchester image
4967 Wardensville Grade, Winchester $429,900

Escape to the peace and quiet of this lovely 4 bedroom, 3 bath ranch rambler situated in the midst of 5 wooded acres in Frederick County. Slightly over 2,600 square fee...

  • 4 Beds
  • 3 Baths
  • VAFV2007202 MLS
118 Maloy Dr, Winchester image
118 Maloy Dr, Winchester $395,000

Great Location for this 3 bedroom 1.5 bath home just waiting for you. Freshly painted, new flooring. This home has something for everyone. Hand hewn mantel over stone ...

  • 3 Beds
  • 2 Baths
  • VAFV2007780 MLS
105 Freedom Cir, Winchester image
105 Freedom Cir, Winchester $454,000

Renovated eat-in kitchen with granite countertops, stainless steel appliances, solid cherry cabinets, a marble backsplash, recessed and under-cabinet LED lighting, and pr...

  • 4 Beds
  • 3 Baths
  • VAFV2007746 MLS
116 Inca Trl, Winchester image
116 Inca Trl, Winchester $179,900

This 1972 rustic A-frame seems right at home in the Shawneeland development. Woodsy setting. Hillside location. Front covered deck, rear private deck. Double sided st...

  • 2 Beds
  • 2 Baths
  • VAFV2007792 MLS
1228 Greenwood Rd, Winchester image
1228 Greenwood Rd, Winchester $489,000

Amazing Newly Renovated 5 Bedroom 2 Full Bath Home sits on 1.41 Acres Centrally located to Historic downtown Winchester, Rt. 50, Rt. 340 and Rt. 7! This home boasts of Ne...

  • 5 Beds
  • 2 Baths
  • VAFV2007382 MLS
103 Sentinel Dr, Winchester image
103 Sentinel Dr, Winchester $449,900

Spectacular Renovation & Move-In Ready! This Brick Front Colonial is located in Star Fort Subdivision just across the Winchester City line & just into Frederick County. Y...

  • 4 Beds
  • 3 Baths
  • VAFV2006538 MLS
505 Quail Dr, Winchester image
505 Quail Dr, Winchester $215,000

Cute cabin in the woods with two extra lots. Live here year around or use for weekend getaway. One level living. Original hardwood floors. Sunroom just inside front doo...

  • 2 Beds
  • 2 Baths
  • VAFV2007614 MLS
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