Winchester County, VA Homes

/57
$630,000 Open Sun 12PM - 2PM
- 4 Beds
- 3.5 Baths
- 4,188 Sq Ft
930 Wayne Dr, Winchester, VA 22601

Beautiful brick-front Colonial in a prime location! Nestled in a quiet neighborhood yet just minutes from I-81 and local amenities, this stunning home offers the perfect blend of convenience and tranquility.Brand new LVP flooring was just installed on both levels. Step into the grand two-story foyer, flanked by a formal living room and dining room accented with elegant columns and a cozy

Elizabeth Flood Keller Williams Realty

930 Wayne Dr, Winchester, VA 22601
/15
$1,500 Per Month
- 2 Beds
- 2 Baths
- 23,305 Sq Ft
- Condo for Rent
443 Millwood Ave Unit 4, Winchester, VA 22601

Well-maintained 2-bedroom, 2-bath apartment in a convenient Winchester location just minutes from Shenandoah University and downtown. This unit offers a comfortable layout with an open living area, two full bathrooms, and in-unit washer and dryer. One assigned parking space is included, along with additional street parking. Located above commercial space with easy access to shopping, dining, and

Rachel Olsen Keller Williams Realty

443 Millwood Ave Unit 4, Winchester, VA 22601
/48
$574,900 Sold Oct 17, 2025

1629 Pondview Dr, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 2,602 Sq Ft
- Built 1995
Last Sold Summary
- $221/SF
- 83 Days On Market
Current Estimated Value $575,993

Last Listing Agent Kerry & Ed Stinson Berkshire Hathaway HomeServices PenFed Realty

1629 Pondview Dr, Winchester, VA 22601

/68
Est $402,604 Not Listed For Sale

3020 Papermill Rd, Winchester, VA 22601
- 4 Beds
- 2 Baths
- 2,902 Sq Ft
- Built 1961
3020 Papermill Rd, Winchester, VA 22601

Last Sold Summary
- 15% Above List Price
- $121/SF
- 68 Days On Market
- Last Sold Price $349,900
- Sep 29, 2023
Last Listing Agent Dave Spence RE/MAX

/29
$324,900
- 3 Beds
- 4 Baths
- 1,336 Sq Ft
120 Worsham Terrace, Winchester, VA 22602

This beautifully maintained 3 level townhome is a great place to call home. Perfectly situated at the back of the subdivision, you get the benefits of the community while enjoying the quiet surroundings. Enjoy the toddler playground and the walking/running trail just steps from your door. This home is also the perfect commuter location less than a mile from Route 7 and Interstate 81. Only minutes

Marielle Thoburn Keller Williams Realty

120 Worsham Terrace, Winchester, VA 22602
/31
$1,500

Total Monthly Price
- 2 Beds
- 1.5 Baths
- 1,100 Sq Ft
- Townhouse for Rent
127-A Peyton St, Winchester, VA 22601

Gorgeous two story apartment with private entrance in the heart of historic downtown Winchester. Walking distance from the Old Town Winchester pedestrian mall with shops, restaurants, cafes and entertainment and the beautiful Handley library.Huge Two bedroom 1.5 bath Apartment with beautiful details located in the bottom two levels of a four story house built in the early 1890s. This is a

127-A Peyton St, Winchester, VA 22601
/38
$499,000 Sold Jun 27, 2025

305 W Whitlock Ave, Winchester, VA 22601
- 4 Beds
- 2.5 Baths
- 2,926 Sq Ft
- Built 1964
Last Sold Summary
- $171/SF
- 3 Days On Market
Current Estimated Value $505,118

Last Listing Agent Gillian Greenfield Coldwell Banker Premier

305 W Whitlock Ave, Winchester, VA 22601

/29
Est $323,162 Not Listed For Sale

3141 Papermill Rd, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 1,183 Sq Ft
- Built 1950
3141 Papermill Rd, Winchester, VA 22601

Last Sold Summary
- 6% Above List Price
- $258/SF
- 10 Days On Market
- Last Sold Price $305,000
- Dec 06, 2024
Last Listing Agent Dalton Stem LPT Realty, LLC

/59
$889,000 Under Contract
- 5 Beds
- 4.5 Baths
- 4,957 Sq Ft
1540 Meadow Branch Ave, Winchester, VA 22601

An exceptional offering of luxury living in the City of Winchester, this stately brick residence presents 4,958 square feet or refined, custom-designed living space. The home features 5 generously sized bedrooms and 4.5 beautifully appointed bathrooms, thoughtfully crafted for both elegant entertaining and everyday comfort. Rich architectural details and custom finishes are showcased throughout,

John Schroth Colony Realty

1540 Meadow Branch Ave, Winchester, VA 22601
/19
$1,500 Per Month
- 2 Beds
- 1.5 Baths
- 1,106 Sq Ft
- Townhouse for Rent
544 Allston Cir, Winchester, VA 22601

NO PETS. 2bedroom 1.5 bath townhouse located minutes to shops and dining in Winchester. Central heating and AC. Large primary bedroom. Unfinished walkout basement. Requirements: (1) Minium household annual income $67k, (2) Good Credit, (3) Good Landlord Reference. $47 application fee per applicant. Contact listing agent for application

Courtney Spaid Crum Realty, Inc.

544 Allston Cir, Winchester, VA 22601
/87
$578,000 Sold Nov 18, 2025

107 Roszel Rd, Winchester, VA 22601
- 4 Beds
- 2.5 Baths
- 3,232 Sq Ft
- Built 1960
Last Sold Summary
- $179/SF
- 59 Days On Market
Current Estimated Value $590,782

Last Listing Agent John Scully Colony Realty

107 Roszel Rd, Winchester, VA 22601

/20
Est $300,199 Not Listed For Sale

3113 Papermill Rd, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 895 Sq Ft
- Built 1956
3113 Papermill Rd, Winchester, VA 22601

Last Sold Summary
- $335/SF
- 11 Days On Market
- Last Sold Price $300,000
- May 24, 2024
Last Listing Agent Marcy Cantatore Atoka Properties | Middleburg Real Estate

/97
$1,150,000
- 6 Beds
- 5 Baths
- 6,682 Sq Ft
217 W Boscawen St, Winchester, VA 22601

Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic District, two blocks from Old Town Walking Mall! Six large bedrooms and five full baths, this historically significant property is one of a kind, offering private garden spaces, romantic terraces, sunlight filled porches, and

Gillian Greenfield Coldwell Banker Premier

217 W Boscawen St, Winchester, VA 22601
/77
$1,725

Total Monthly Price
- 1 Bed
- 1 Bath
- 650 Sq Ft
- Condo for Rent
342 Fairmont Ave Unit 5 FULLY FURNISHED RENTAL Retro Loves Company, Winchester, VA 22601

COMPLETELY FURNISHED RENTALPerfect for traveling professionals or students.Furnished one bedroom located behind the beautiful Handley library. This quaint one bedroom apartment is on the 3rd floor of a historic home facing Fairmont Ave. It has terrific views and a spectacular view of fireworks on Apple Blossom, July 4th and New Years Eve. Beautiful details and wainscotting, built in

342 Fairmont Ave Unit 5 FULLY FURNISHED RENTAL Retro Loves Company, Winchester, VA 22601
/64
$850,000 Sold May 13, 2025

765 Seldon Dr, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 4,144 Sq Ft
- Built 1998
Last Sold Summary
- $205/SF
- 0 Days On Market
Current Estimated Value $846,980

Last Listing Agent Dan Whitacre Colony Realty

765 Seldon Dr, Winchester, VA 22601

/37
Est $348,183 Not Listed For Sale

2905 First St, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 1,584 Sq Ft
- Built 1968
2905 First St, Winchester, VA 22601

Last Sold Summary
- 11% Above List Price
- $199/SF
- 11 Days On Market
- Last Sold Price $315,000
- Sep 25, 2023
Last Listing Agent Melissa Johnston ERA Oakcrest Realty, Inc.

/54
$445,000 Under Contract
- 3 Beds
- 2.5 Baths
- 1,938 Sq Ft
413 George St, Winchester, VA 22601

Beautifully updated 3 bedroom, 2.5 bathroom single family home tucked on a quiet street in Winchester. The main level features updated flooring and a renovated kitchen with granite countertops, stainless steel appliances, shaker cabinetry, and a stylish backsplash. The primary suite offers a beautifully updated en suite featuring ceramic tile flooring, a tiled shower, and a luxury jet shower

Shannon Jones Pearson Smith Realty, LLC

413 George St, Winchester, VA 22601
/11
$1,149 Per Month
- 1 Bed
- 1 Bath
- 420 Sq Ft
- Condo for Rent
1700 Roberts St Unit 7, Winchester, VA 22601

RECENTLY RENOVATED, ALL-BRICK BUILDING THAT WAS COMPLETELY REDONE OVER LAST SEVERAL YEARS * UNIT HAS NEWER STAINLESS-STEEL APPLIANCES AND NEWER VINYL-PLANK FLOORING * EXTERIOR OF BUILDING WAS PAINTED IN 2018. NEW WINDOWS, NEW GUTTERS AND NEW ROOF ADDED IN 2018. ALL NEW ELECTRIC SERVICE IN 2018, ALSO * AWESOME KITCHEN W/NEWER CABINETS & GRANITE C'TOPS * REDONE BATH W/CERAMIC TILE FLOORS & TUB

John Gregory Holmes Samson Properties

1700 Roberts St Unit 7, Winchester, VA 22601
/55
$675,000 Sold Feb 12, 2026

800 Lake Dr, Winchester, VA 22601
- 5 Beds
- 4 Baths
- 4,576 Sq Ft
- Built 2010
Last Sold Summary
- $148/SF
- 87 Days On Market
Current Estimated Value $676,285

Last Listing Agent Lisa Behr Hunt Country Sotheby's International Realty

800 Lake Dr, Winchester, VA 22601

/6
Est $294,960 Not Listed For Sale

3037 Papermill Rd, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
- Built 1960
3037 Papermill Rd, Winchester, VA 22601

Last Sold Summary
- 7% Above List Price
- $273/SF
- 21 Days On Market
- Last Sold Price $275,000
- Oct 31, 2024
Last Listing Agent Brett Sowder RE/MAX

/67
$569,900
- 3 Beds
- 2.5 Baths
- 2,450 Sq Ft
1930 Harvest Dr, Winchester, VA 22601

Experience the perfect blend of traditional charm and modern scale in this meticulously maintained residence located in the highly sought-after and established community of Meadow Branch South. The striking exterior, framed by a beautifully manicured lawn and mature landscaping, welcomes you into a soaring two-story foyer anchored by gleaming hardwood floors. The main level is designed for

Dan Whitacre Colony Realty

1930 Harvest Dr, Winchester, VA 22601
/26
$2,400

Total Monthly Price
- 3 Beds
- 2.5 Baths
- 1,672 Sq Ft
- House for Rent
504 N Loudoun St, Winchester, VA 22601

Beautifully updated 3-bedroom, 2.5-bath home offering 1,672 SF of living space in a prime, highly walkable location just minutes from downtown (500 block of N Loudoun Street).You have the option of fully furnished living areas and partially furnished bedrooms for an additional $150/mo.Optional furnishings include:Large living room sofaDining table with two chairsKitchen

504 N Loudoun St, Winchester, VA 22601
/38
$330,000 Sold Jun 20, 2025

111 Montague Ave, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 1,172 Sq Ft
- Built 1955
Last Sold Summary
- $282/SF
- 3 Days On Market
Current Estimated Value $319,768

Last Listing Agent Tracie Clawson ERA Oakcrest Realty, Inc.

111 Montague Ave, Winchester, VA 22601

/24
Est $328,495 Not Listed For Sale

2959 S Pleasant Valley Rd, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 1,199 Sq Ft
- Built 1989
2959 S Pleasant Valley Rd, Winchester, VA 22601

Last Sold Summary
- 13% Above List Price
- $242/SF
- 5 Days On Market
- Last Sold Price $290,000
- Nov 21, 2023
Last Listing Agent Anna Fox NextHome Realty Select

/58
$279,000
- 4 Beds
- 1.5 Baths
- 1,449 Sq Ft
301 Shawnee Ave, Winchester, VA 22601

Priced well below assessed value and sold strictly AS IS — this is the deal investors and renovation buyers have been searching for. This 4-bedroom, 1.5-bath home sits on a generous corner lot in an established Winchester neighborhood, just minutes from historic Old Town, the walking mall, and Shenandoah University. Original hardwood floors hint at the character waiting to be restored, and a

Barton Chasler Realty ONE Group Old Towne

301 Shawnee Ave, Winchester, VA 22601
/15
$2,300 Per Month
- 3 Beds
- 4 Baths
- 1,408 Sq Ft
- Townhouse for Rent
2632 Daniel Terrace, Winchester, VA 22601

"Drive On Over To Daniel Ter" This beautiful townhouse has 3-Bedrooms, 2 -Full Baths and 2-Half Baths. Home was fully renovated in 2019 and is ready for you to move right in! The first floor has gorgeous hardwood floors with an open concept. Kitchen has granite countertops and stainless-steel appliances. The primary bedroom has a private bathroom and a staircase leading to a loft area making the

Matt Kilmer Samson Properties

2632 Daniel Terrace, Winchester, VA 22601
/39
$370,000 Sold Jul 18, 2025

625 Butler Ave, Winchester, VA 22601
- 5 Beds
- 2.5 Baths
- 1,050 Sq Ft
- Built 1968
Last Sold Summary
- $352/SF
- 4 Days On Market
Current Estimated Value $356,700

Last Listing Agent Aracely Rivera First Decision Realty LLC

625 Butler Ave, Winchester, VA 22601

/21
Est $322,302 Not Listed For Sale

121 Summit Ave, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 1,020 Sq Ft
- Built 1981
121 Summit Ave, Winchester, VA 22601

Last Sold Summary
- 1% Below List Price
- $318/SF
- 9 Days On Market
- Last Sold Price $324,500
- Nov 15, 2024
Last Listing Agent Heloisa Amar Samson Properties

/48
$624,900 Pending
- 3 Beds
- 2 Baths
- 2,153 Sq Ft
1416 Gordon Place, Winchester, VA 22601

Beautifully renovated all-brick rancher offering effortless, low-maintenance living in a highly desirable active adult 55+ community! Thoughtfully updated throughout, this home features a 50-year roof installed in 2021, brand-new flooring, and a fully upgraded kitchen and bathrooms, designed with both style and function in mind. The kitchen showcases elegant quartz countertops, soft-close

Michele Gibson Samson Properties

1416 Gordon Place, Winchester, VA 22601
/16
$1,550

Total Monthly Price
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
- Townhouse for Rent
222 E Whitlock Ave, Winchester, VA 22601

•3 Bedroom 1 Bath two-story townhome with basement.• •Great in-town location just a few blocks off Valley Avenue (Rt 11) and Millwood Pike (Rt 50).•• Hardwood / Vinyl / Carpet Flooring••Stove / Refrigerator ••Connection for Washer & Dryer••Gas Furnace and Hot Water••Tenant would provide window AC units.••Tenant pays Electric, Gas, & Water/Sewer••RENTERS INSURANCE

222 E Whitlock Ave, Winchester, VA 22601
/87
$650,000 Sold Sep 16, 2025

504 Old Fort Rd, Winchester, VA 22601
- 5 Beds
- 6 Baths
- 3,824 Sq Ft
- Built 2003
Last Sold Summary
- $170/SF
- 74 Days On Market
Current Estimated Value $678,893

Last Listing Agent Dallas Croft Samson Properties

504 Old Fort Rd, Winchester, VA 22601

/40
Est $296,725 Not Listed For Sale

2937 Grace St, Winchester, VA 22601
- 2 Beds
- 1 Bath
- 851 Sq Ft
- Built 1962
2937 Grace St, Winchester, VA 22601

Last Sold Summary
- 15% Above List Price
- $302/SF
- 0 Days On Market
- Last Sold Price $257,000
- Apr 27, 2023
Last Listing Agent Kathrin Donovan Keller Williams Realty

/7
$1,100,000
- Land
- 2.3 Acres
- $478,261 per Acre
0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601

2.3 Acre Outparcel on Pleasant Valley Road for Sale Neighbors include Walmart, Ross, Target, Panera Bread, Olive Garden, Petco, and the list goes on! Zoned CM1, ideal for auto sales, offices, retail, and flex development. All utilities to site. Outstanding proximity to massive commercial and multifamily growth. VA's fastest growing City in it's fastest growing commercial district. Almost 500'

Gillian Greenfield Coldwell Banker Premier

0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601
/2
$1,300 Per Month
- 2 Beds
- 1.5 Baths
- 2,146 Sq Ft
- House for Rent
578 York Ave, Winchester, VA 22601

2 large bedroom duplex, composite/carpet/vinyl flooring, stove and refrigerator, in city location , 650 credit score, no suits, judgments or collections, application in one person's name reasonable water/sewer included, off street parking NO PETS

James Golladay Crum Realty, Inc.

578 York Ave, Winchester, VA 22601
/47
$425,000 Sold Mar 11, 2026

431 Jefferson St, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 1,632 Sq Ft
- Built 1956
Last Sold Summary
- 1% Above List Price
- $260/SF
- 4 Days On Market
Current Estimated Value $422,151

Last Listing Agent Dan Whitacre Colony Realty

431 Jefferson St, Winchester, VA 22601

/43
Est $346,566 Not Listed For Sale

2924 Grace St, Winchester, VA 22601
- 4 Beds
- 2 Baths
- 1,285 Sq Ft
- Built 1975
2924 Grace St, Winchester, VA 22601

Last Sold Summary
- 2% Above List Price
- $265/SF
- 5 Days On Market
- Last Sold Price $340,000
- Apr 14, 2025
Last Listing Agent Kristen Kerns Roberts Realty Group, LLC

/55
$310,500
- 3 Beds
- 2 Baths
- 1,474 Sq Ft
406 Highland Ave, Winchester, VA 22601

OPEN HOUSE SATURDAY MAY 9th 1 - 3 PM!Located in The Old Town Winchester area but on a quiet street, we are happy to list this nicely remodeled 2 level home. Since the purchase of this center hall Circa 1930s home, the owners have totally resurfaced and painted the metal roof, installed windows,installed all new plumbing and electrical services, a dual zoned HVAC system, sanded the gleaming

Lisette Turner Century 21 Redwood Realty

406 Highland Ave, Winchester, VA 22601
/2
$1,295

Total Monthly Price
- 2 Beds
- 1 Bath
- 1,115 Sq Ft
- Townhouse for Rent
307 S Kent St, Winchester, VA 22601

** COMING SOON** pictures of similar unit**Charming 2 Bedroom 1 Bath townhouse with full basement for extra storage. Located in the historical district of downtown Winchester. Just a short walk to many of the historical sites, a few blocks from the walking mall and government offices while just a short drive to Winchester Medical Center and Shenandoah University. Pet friendly with approval

307 S Kent St, Winchester, VA 22601
/34
$375,000 Sold Feb 06, 2026

318 E Piccadilly St, Winchester, VA 22601
- 4 Beds
- 1.5 Baths
- 1,953 Sq Ft
- Built 1929
Last Sold Summary
- 6% Below List Price
- $192/SF
- 40 Days On Market
Current Estimated Value $379,644

Last Listing Agent Dan Whitacre Colony Realty

318 E Piccadilly St, Winchester, VA 22601

/25
Est $386,032 Not Listed For Sale

2921 Second St, Winchester, VA 22601
- 4 Beds
- 3 Baths
- 1,147 Sq Ft
- Built 1955
2921 Second St, Winchester, VA 22601

Last Sold Summary
- 1% Below List Price
- $340/SF
- 39 Days On Market
- Last Sold Price $389,999
- Dec 14, 2023
Last Listing Agent Joelle Graham Weichert Corporate

Showing Results 201 - 240, Page 6 of 18

Virginia Winchester County

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