Winchester County, VA Homes

/6
$95,000 Pending
- Land
- 0.2 Acre
- $475,000 per Acre
816 Allen Dr, Winchester, VA 22601

MULTIPLE OFFERS RECEIVED. OFFER DEADLINE IS MONDAY, MARCH 22, 2026 AT 5:00 P.M. Rare opportunity to buy a level building lot conveniently located off Pleasant Valley Road in Eastview Subdivision. This lot is being sold with a 24x24 two bay garage. The garage presently has electric service from the adjoining property, which is also being sold by the same owners. If this lot w/ garage are purchased

Elizabeth Page Boxwell MarketPlace REALTY

816 Allen Dr, Winchester, VA 22601
/13
$1,599 per month
- 2 Beds
- 1.5 Baths
- 900 Sq Ft
- Townhouse for Rent
3107 Shawnee Dr Unit 7, Winchester, VA 22601

NOW ACCEPTING PETS ON A CASE BY CASE BASIS!!Beautifully Renovated Unit Two level townhome*Full size Washer & Dryer*Hardwood like Floors* Huge Brand New Eat-In Kitchen*Granite counters & Stainless Steel Appliances*Spacious bedrooms*Large closets*Individually controlled HVAC and hot water heater*Plenty of parking*1 mile from great shopping on Valley Avenue, 10 minute from downtown Winchester

Steve DuBrueler Coldwell Banker Premier

3107 Shawnee Dr Unit 7, Winchester, VA 22601
/2
$565,000 Sold Sep 16, 2025

183 Omps Dr, Winchester, VA 22601
- 4 Beds
- 2.5 Baths
- 2,617 Sq Ft
- Built 1985
Last Sold Summary
- $216/SF
Current Estimated Value $566,476

Last Listing Agent Stuart Wolk ERA Oakcrest Realty, Inc.

183 Omps Dr, Winchester, VA 22601

/30
Est $282,859 Not Listed For Sale

2955 Sorrell Ct, Winchester, VA 22601
- 2 Beds
- 1.5 Baths
- 1,332 Sq Ft
- Built 2001
2955 Sorrell Ct, Winchester, VA 22601

Last Sold Summary
- 9% Above List Price
- $195/SF
- 5 Days On Market
Last Sold Price $260,000

Last Listing Agent James Amick RE/MAX

/42
$499,000
- 4 Beds
- 2.5 Baths
- 2,068 Sq Ft
2510 Windwood Dr, Winchester, VA 22601

Welcome home to this spacious, light filled four bedroom, two and a half bath home in the Westridge subdivision. The traditional main level floor plan offers the perfect separation of spaces which include a formal dining room or potential home office/den, a kitchen that opens into a living area perfect for a casual breakfast table and a cozy sofa in front of the fireplace and a large, more formal

Dana Cloud Realty ONE Group Old Towne

2510 Windwood Dr, Winchester, VA 22601
/15
$1,350 per month
- 2 Beds
- 1 Bath
- 1,045 Sq Ft
- House for Rent
434 Fairmont Ave Unit 1, Winchester, VA 22601

Come Checkout This PRIVATE First Floor 2 bedroom apartment. Home was renovated 2023, New Kitchen Cabinets, In house Washer & Dryer, Full Bath, Large Front Room & Dining Room. Off Street Parking Close to Downtown & Shopping

Richard Kozlowski Long & Foster Real Estate, Inc.

434 Fairmont Ave Unit 1, Winchester, VA 22601
/74
$794,000 Sold Aug 27, 2025

1001 Armistead St, Winchester, VA 22601
- 5 Beds
- 4 Baths
- 4,295 Sq Ft
- Built 2005
Last Sold Summary
- $185/SF
- 4 Days On Market
Current Estimated Value $788,389

Last Listing Agent Sheila Pack RE/MAX Roots

1001 Armistead St, Winchester, VA 22601

/16
Est $289,499 Not Listed For Sale

2975 Sorrell Ct, Winchester, VA 22601
- 2 Beds
- 2.5 Baths
- 1,880 Sq Ft
- Built 1990
2975 Sorrell Ct, Winchester, VA 22601

Last Sold Summary
- 11% Above List Price
- $138/SF
Last Sold Price $260,000

Last Listing Agent Amanda White Nova Home Hunters Realty

/51
$279,000 Under Contract
- 2 Beds
- 1 Bath
- 759 Sq Ft
424 Highland Ave, Winchester, VA 22601

CUTE AS A BUTTON! This updated Cottage Rambler perched on a quiet tree lined street sits in the heart of booming Winchester, just minutes from Old Towne. Newly renovated and very affordable! Refreshed solid hardwood flooring, new kitchen with bright quartz countertops, stainless steel appliances, newer HVAC (only 3 years old) new lighting throughout, newer bathroom includes tiled tub with

Jacqueline Hitchcock Long & Foster Real Estate, Inc.

424 Highland Ave, Winchester, VA 22601
/8
$1,595 per month
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
- Townhouse for Rent
202 E Whitlock Ave, Winchester, VA 22601

Experience the charm of this beautifully renovated end-of-row townhouse in the heart of the City of Winchester, available for lease starting November 19, 2025. This residence, originally built in 1956, will undergo a major renovation, ensuring modern luxury meets classic elegance. With three spacious bedrooms and a full bath, this home is designed for comfort and style. The partially finished

Brandon Pifer Pifer Realty, LLC

202 E Whitlock Ave, Winchester, VA 22601
/12
$375,000 Sold Jun 30, 2025

122 E Pall Mall St, Winchester, VA 22601
- Studio
- 1,372 Sq Ft
- Built 1920
Last Sold Summary
- $273/SF
- 13 Days On Market
Last Listing Agent Kathy Colville Century 21 Redwood Realty

122 E Pall Mall St, Winchester, VA 22601

/23
Est $307,316 Not Listed For Sale

2950 Sorrell Ct, Winchester, VA 22601
- 3 Beds
- 3.5 Baths
- 1,280 Sq Ft
- Built 1990
2950 Sorrell Ct, Winchester, VA 22601

Last Sold Summary
- 6% Above List Price
- $226/SF
- 34 Days On Market
Last Sold Price $289,000

Last Listing Agent Maria Jaimes Millennium Realty Group Inc.

/38
$449,990 New Construction
- 4 Beds
- 3.5 Baths
- 1,889 Sq Ft
1819 Reese Ct, Winchester, VA 22601

1819 Reese Court is a move-in ready 3-level townhome with full brick front in Winchester, VA. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained oak stairs lead you to the main level with LVP flooring. The kitchen is equipped with beautiful quartz countertops, sasparilla cabinets, and stainless-steel appliances. The upper

D.R. Horton Builder

1819 Reese Ct, Winchester, VA 22601
/25
$1,250 per month
- 2 Beds
- 1 Bath
- 864 Sq Ft
- Condo for Rent
24 Jackson Ave Unit 2, Winchester, VA 22601

AFFORDABLE AND CHARMING. Freshly painted and move-in ready. Short drive to downtown, Winchester Medical Center, I-81 and Rt. 37. Convenient to shopping and services. Spacious 2-bedroom upstairs apartment with off-street parking in the rear, front porch and a private 16x12 rear deck. Eat-in kitchen with refrigerator and oven/range. No smoking. No pets. Landlord prefers credit scores of 650 or

Teresa Strohmeyer ERA Oakcrest Realty, Inc.

24 Jackson Ave Unit 2, Winchester, VA 22601
/39
$270,000 Sold Jan 21, 2026

423 Highland Ave, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
- Built 1930
Last Sold Summary
- $208/SF
- 44 Days On Market
Current Estimated Value $261,442

Last Listing Agent Carlos Soares Samson Properties

423 Highland Ave, Winchester, VA 22601

/16
Est $277,921 Not Listed For Sale

503 Yorktowne Place, Winchester, VA 22601
- 2 Beds
- 1.5 Baths
- 1,116 Sq Ft
- Built 1984
503 Yorktowne Place, Winchester, VA 22601

Last Sold Summary
- 16% Above List Price
- $214/SF
- 3 Days On Market
Last Sold Price $239,000

Last Listing Agent Jennifer Sacco RE/MAX

/46
$499,990 Open Sat 1PM - 2PM
- 2 Beds
- 2 Baths
- 1,850 Sq Ft
411 302 N Loudoun St, Winchester, VA 22601

Just 3 blocks to the Winchester Walking Mall, Unit 302 at The Fort puts downtown coffee shops, cuisine, mom & pop shops, museums, art, & the grand library right at your fingertips—then brings you home to a penthouse retreat with the best views in the building of both sunrise and sunset. Kiss yard work bye bye & say hello to single level living with an elevator. Where off street parking is

Sarah Abderrazzaq Realty ONE Group Old Towne

411 302 N Loudoun St, Winchester, VA 22601
/19
$1,350 per month
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
- Condo for Rent
113 W Boscawen St Unit 3, Winchester, VA 22601

3rd floor walk-up apartment. Downtown Winchester is this 2 bedroom, 1 bath apartment featuring an abundancy of light with numerous windows, large rooms and hardwood floors. Primary bedroom has direct access to bathroom. Water, sewer and trash pick-up is provided in the monthly rent as is 1 parking space in the Braddock Street Parking Garage. Tenant is responsible for electricity and natural gas

Barbara Gaul Jim Barb Realty, Inc.

113 W Boscawen St Unit 3, Winchester, VA 22601
/34
$450,000 Sold Oct 17, 2025

711 S Braddock St, Winchester, VA 22601
- 3 Beds
- 3.5 Baths
- 2,052 Sq Ft
- Built 2016
Last Sold Summary
- $219/SF
- 7 Days On Market
Current Estimated Value $466,318

Last Listing Agent Dave Spence RE/MAX Roots

711 S Braddock St, Winchester, VA 22601

/47
Est $471,065 Not Listed For Sale

2894 Packer St, Winchester, VA 22601
- 4 Beds
- 2.5 Baths
- 2,460 Sq Ft
- Built 2006
2894 Packer St, Winchester, VA 22601

Last Sold Summary
- 11% Above List Price
- $173/SF
- 7 Days On Market
Last Sold Price $425,000

Last Listing Agent Renzo Falla RE/MAX

/47
$985,000
- 7 Beds
- 5.5 Baths
- 6,540 Sq Ft
1020 Breckinridge Ln, Winchester, VA 22601

This property exudes luxury multigenerational living in Meadowbranch! • Main level bedroom + bath• 6500 sq ft• Wet bar in primary suite• 3-car garage• No HOA• Backing to trees, and more..... Approximately 6,500 finished square feet of living space! A place to grow, gather, and stay awhile! A brick-paved, rocking chair-worthy, front porch sets the tone, and the charming side

Sheila Pack RE/MAX Roots

1020 Breckinridge Ln, Winchester, VA 22601
/32
$2,800 per month
- 2 Beds
- 2 Baths
- 1,230 Sq Ft
- Condo for Rent
210 E Boscawen St Unit 202, Winchester, VA 22601

This stunning apartment features 9 south facing windows for maximum natural light, just steps from all of the restaurants, night life and events in Old Town Winchester. The historic Winchester Star building has been renovated for luxury living that includes private parking, a rarity downtown. Two large bedrooms, each with their own en-suite and walk-in closet are set apart by the open space

Katie Landi Jordan Samson Properties

210 E Boscawen St Unit 202, Winchester, VA 22601
/105
$1,149,000 Sold Feb 20, 2026

819 Armistead St, Winchester, VA 22601
- 5 Beds
- 3.5 Baths
- 5,262 Sq Ft
- Built 1989
Last Sold Summary
- 4% Below List Price
- $218/SF
- 1 Day On Market
Current Estimated Value $1,190,972

Last Listing Agent Natalie Langford ERA Oakcrest Realty, Inc.

819 Armistead St, Winchester, VA 22601

/46
Est $466,775 Not Listed For Sale

201 Russelcroft Rd, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 3,066 Sq Ft
- Built 1970
201 Russelcroft Rd, Winchester, VA 22601

Last Sold Summary
- 10% Above List Price
- $139/SF
- 10 Days On Market
Last Sold Price $425,000

Last Listing Agent Dorothy Vance The KW Collective

/22
$299,900
- 3 Beds
- 1 Bath
- 1,204 Sq Ft
625 Watson Ave, Winchester, VA 22601

Nestled in Orchard Terrace, this beautifully updated Colonial home is ideally located within Winchester city limits, just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment. The updated kitchen features new cabinets, granite countertops, stainless steel appliances, a new sink and faucet, and vinyl plank flooring. The bathroom includes a new vanity, vanity

Jennifer Sacco RE/MAX Roots

625 Watson Ave, Winchester, VA 22601
/2
$2,000 per month
- 1 Bed
- 1 Bath
- 1,000 Sq Ft
- Condo for Rent
619 S Cameron St Unit 1, Winchester, VA 22601

Charming apartment located in 2 family unit, walking distance to Old Town Winchester. Original hardwood floors, light and bright unit with washer and dryer in unit. Landlord pays water and sewer and tenant pays electric. Shared yard.

Brock Harris Samson Properties

619 S Cameron St Unit 1, Winchester, VA 22601
/35
$507,000 Sold Mar 31, 2025

605 Lake Dr, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 2,136 Sq Ft
- Built 2011
Last Sold Summary
- $237/SF
- 10 Days On Market
Current Estimated Value $522,184

Last Listing Agent Yvonne Holland Samson Properties

605 Lake Dr, Winchester, VA 22601

/40
Est $421,324 Not Listed For Sale

129 Garden Ct, Winchester, VA 22601
- 3 Beds
- 3 Baths
- 2,613 Sq Ft
- Built 1970
129 Garden Ct, Winchester, VA 22601

Last Sold Summary
- 4% Above List Price
- $155/SF
- 3 Days On Market
Last Sold Price $405,000

Last Listing Agent Stephanie Ryall Realty ONE Group Old Towne

/61
$459,000
- 6 Beds
- 3 Baths
- 1,552 Sq Ft
2250 Roosevelt Blvd, Winchester, VA 22601

Charming Cape Cod nestled in a quiet residential neighborhood, just minutes from Route 11 and I-81 for easy commuting. This light-filled home welcomes you with a bright living room featuring a stunning stone fireplace as its centerpiece. The cabinet-packed kitchen is the heart of the home and offers granite countertops and a bar-height peninsula that opens seamlessly to the living room . The main

Heloisa Amar Samson Properties

2250 Roosevelt Blvd, Winchester, VA 22601
/2
$2,000 per month
- 1 Bed
- 1 Bath
- 2,124 Sq Ft
- Condo for Rent
619 S Cameron St Unit 2, Winchester, VA 22601

Charming apartment located in 2 family unit, walking distance to Old Town Winchester. Original hardwood floors, light and bright unit with washer and dryer in unit. Landlord pays water and sewer and tenant pays electric. Shared yard.

Brock Harris Samson Properties

619 S Cameron St Unit 2, Winchester, VA 22601
/44
$782,000 Sold Oct 03, 2025

939 Buckner Dr, Winchester, VA 22601
- 5 Beds
- 4.5 Baths
- 6,122 Sq Ft
- Built 2000
Last Sold Summary
- $128/SF
- 46 Days On Market
Current Estimated Value $914,398

Last Listing Agent Kiran K. Morzaria Parekh Samson Properties

939 Buckner Dr, Winchester, VA 22601

/73
Est $447,870 Not Listed For Sale

212 W Cedarmeade Ave, Winchester, VA 22601
- 5 Beds
- 2.5 Baths
- 2,899 Sq Ft
- Built 1967
212 W Cedarmeade Ave, Winchester, VA 22601

Last Sold Summary
- 9% Above List Price
- $141/SF
- 91 Days On Market
Last Sold Price $410,000

Last Listing Agent Gina Chatham Century 21 Redwood Realty

/34
$269,000 Under Contract
- 2 Beds
- 2 Baths
- 897 Sq Ft
939 Woodland Ave, Winchester, VA 22601

This Winchester City charmer is the perfect starter home, downsizing option, or investment opportunity. Thoughtfully updated with all the heavy lifting complete at the same time preserving the charm and character. Bedroom one is on the main floor with attached bathroom (complete with clawfoot tub!!) Upstairs you will find the sweetest loft perfect for home office, or reading nook...Second bedroom

Kristen Kerns Roberts Realty Group, LLC

939 Woodland Ave, Winchester, VA 22601
/17
$2,350 per month
- 4 Beds
- 3.5 Baths
- 1,784 Sq Ft
- Townhouse for Rent
217 Monteith Dr, Winchester, VA 22601

Kumaresan Vadivel Trust Realty, Inc.

217 Monteith Dr, Winchester, VA 22601
/49
$528,000 Sold Jun 24, 2025

645 Beehive Way, Winchester, VA 22601
- 4 Beds
- 2.5 Baths
- 2,748 Sq Ft
- Built 2007
Last Sold Summary
- $192/SF
- 19 Days On Market
Current Estimated Value $540,618

Last Listing Agent Laura White ERA Oakcrest Realty, Inc.

645 Beehive Way, Winchester, VA 22601

/41
Est $332,420 Not Listed For Sale

309 Wentworth Dr, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 1,148 Sq Ft
- Built 1966
309 Wentworth Dr, Winchester, VA 22601

Last Sold Summary
- 15% Above List Price
- $253/SF
- 4 Days On Market
Last Sold Price $290,000

Last Listing Agent Julie Teets ERA Oakcrest Realty, Inc.

/16
$279,000 Under Contract
- 2 Beds
- 1 Bath
- 950 Sq Ft
20 E Hart St, Winchester, VA 22601

This is a completely restored Winchester classic within walking distance to the downtown area and Handley High school. Located at the end of street. Home improvements include new HVAC, plumbing, electric and appliances. Interior pictures will follow as soon as painting has been completed.

Meridee Powars Link Realty Services LLC

20 E Hart St, Winchester, VA 22601
/16
$2,350 per month
- 4 Beds
- 3.5 Baths
- 1,784 Sq Ft
- Townhouse for Rent
226 Monteith Dr, Winchester, VA 22601

Kumaresan Vadivel Trust Realty, Inc.

226 Monteith Dr, Winchester, VA 22601
/37
$429,000 Sold May 09, 2025

200 E Piccadilly St, Winchester, VA 22601
- 3 Beds
- 3.5 Baths
- 2,052 Sq Ft
- Built 2022
Last Sold Summary
- $209/SF
- 364 Days On Market
Current Estimated Value $438,125

Last Listing Agent Jason Aikens RE/MAX Roots

200 E Piccadilly St, Winchester, VA 22601

/33
Est $374,748 Not Listed For Sale

430 Wentworth Dr, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 2,211 Sq Ft
- Built 1954
430 Wentworth Dr, Winchester, VA 22601

Last Sold Summary
- 2% Above List Price
- $166/SF
- 108 Days On Market
Last Sold Price $367,500

Last Listing Agent Traci Shoberg Samson Properties

Showing Results 321 - 360, Page 9 of 18

Virginia Winchester County

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