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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

265 Mcdonald Rd, Winchester image
265 Mcdonald Rd, Winchester $375,000

265 McDonald Rd is a 1-story Winchester home built in 1974 with a lower level and connected outdoor spaces. The kitchen includes cabinet storage, a preparation counter, a...

  • 3 Beds
  • 2 Baths
  • VAFV2044758 MLS
131 Country Club Cir, Winchester image
131 Country Club Cir, Winchester $435,000

No HOA in the heart of Winchester! This charming brick rancher features three bedrooms, two baths, tall ceilings, fresh paint, hardwood floors, and a fireplace on the ma...

  • 3 Beds
  • 2 Baths
  • VAFV2044502 MLS
148 Doe Trl, Winchester image
148 Doe Trl, Winchester $317,265

Welcome to this charming three-bedroom, two-bathroom raised ranch nestled on a quiet, tree-lined street in one of the area’s most close-knit neighborhoods. Full of charac...

  • 3 Beds
  • 2 Baths
  • VAFV2044700 MLS
114 Tudor Dr, Winchester image
114 Tudor Dr, Winchester $289,900

Spacious three-level townhome in a desirable Winchester community, conveniently located near Sunnyside and Old Town Winchester! Offering generously sized bedrooms, three ...

  • 3 Beds
  • 4 Baths
  • VAFV2044686 MLS
100 Gooseberry Dr, Winchester image
100 Gooseberry Dr, Winchester $515,000

Welcome to 100 Gooseberry Drive, located in Winchester's established Cross Creek Village community! This meticulously maintained brick rancher offers true main-level livi...

  • 2 Beds
  • 3 Baths
  • VAFV2044428 MLS
Tumble Leaf Lane, Winchester image
Tumble Leaf Lane, Winchester $805,000

CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Main Level Owners Suite floorplan the Box...

  • 4 Beds
  • 4 Baths
  • VAFV2044518 MLS
Winchester image
Winchester $235,000

Ground floor condo featuring 2 bedroom 2 full baths and concrete patio. Level entry from parking area with no steps as well as wide hallway and doors for handicap access...

  • 2 Beds
  • 2 Baths
  • VAFV2044668 MLS
302 Canyon Rd, Winchester image
302 Canyon Rd, Winchester $525,000

Welcome to a home that gives you room for all the things that matter—working from home, hosting friends, relaxing at the end of the day, and making the space truly your o...

  • 4 Beds
  • 4 Baths
  • VAFV2044280 MLS
310 Goldenrod Rd, Winchester image
310 Goldenrod Rd, Winchester $430,000

This is the one you have been waiting for!! Well cared for home, one story living in desirable Briarwood Estates...east side location convenient to commuter routes, shopp...

  • 3 Beds
  • 2 Baths
  • VAFV2044648 MLS
323 Copperfield Ln, Winchester image
323 Copperfield Ln, Winchester $290,000

Nestled in the charming Copperfield neighborhood, this delightful townhouse offers a perfect blend of comfort and convenience. Built in 2002, this well-maintained home fe...

  • 2 Beds
  • 3 Baths
  • VAFV2044558 MLS
128 Alliance Ct, Winchester image
128 Alliance Ct, Winchester $550,000

Welcome to 128 Alliance Court, a beautifully maintained, move-in-ready home built in 2021 and offering over 3,200 finished square feet across three spacious levels. The o...

  • 4 Beds
  • 4 Baths
  • VAFV2044610 MLS
111 Haven Ter, Winchester image
111 Haven Ter, Winchester $300,000

Charming 3-Bedroom Rambler on a Spacious Lot! Welcome to 111 Haven Terrace, a conveniently located 3-bedroom, 1-bath rambler situated on approximately 0.26 acres. This si...

  • 3 Beds
  • 1 Baths
  • VAFV2044568 MLS
900 Enfield Dr, Winchester image
900 Enfield Dr, Winchester $380,000

Nestled in the serene Wilde Acres community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevate...

  • 4 Beds
  • 3 Baths
  • VAFV2044636 MLS
110 Bentpath Ct, Winchester image
110 Bentpath Ct, Winchester $710,000

Welcome to 110 Betpath Ct, nestled within the premier Twin Lakes Overlook (TLO) enclave of exclusively single-family homes by Toll Brothers and Richmond American, this ex...

  • 5 Beds
  • 4 Baths
  • VAFV2044642 MLS
1960 Siler Rd, Winchester image
1960 Siler Rd, Winchester $499,900

Looking for one-level living with acreage, a detached workshop/garage, RV/camper parking, and no HOA? Welcome to 1960 Siler Road, a custom-built ranch situated on 5 fence...

  • 3 Beds
  • 2 Baths
  • VAFV2044524 MLS
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