Winchester County, VA Homes

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  /33

  $230,000

  Under Contract

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft

  554 N Kent St, Winchester, VA 22601

  Conveniently located in the heart of the City of Winchester, this charming home is just a short walk to the shops, restaurants, entertainment, and events of historic Old Town Winchester. Offering 3 bedrooms and 1 full bath, the home features an eat-in kitchen, a fenced backyard, and a storage shed for added convenience. Ready for your personal touches, this property offers an excellent

  Leah Clowser RE/MAX Roots

  554 N Kent St, Winchester, VA 22601
• 

  

  

  /7

  $1,400

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Townhouse for Rent

  382 Woodstock Ln, Winchester, VA 22601

  This property at 382 Woodstock Ln features 2 bedrooms and 1 bathroom within a total living space of 1,000 square feet. The living room offers ample space for relaxation and entertainment. The bathroom includes a tub/shower combination for convenience. Each bedroom is designed to accommodate various furniture arrangements and provides adequate closet space. Additional amenities include storage

  382 Woodstock Ln, Winchester, VA 22601
• 

  

  /2

  $585,000

  Sold May 04, 2026

  328 Sheridan Ave, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,909 Sq Ft
  • Built 1958

  Last Sold Summary

  • $201/SF
  • 3 Days On Market

  Current Estimated Value $580,750

  Last Listing Agent Mary Casselano Dream Real Estate

  328 Sheridan Ave, Winchester, VA 22601
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  /32

  Not Listed For Sale

  3138 Eton Place, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,842 Sq Ft
  • Built 2024

  3138 Eton Place, Winchester, VA 22601

  Last Sold Summary

  Last Listing Agent Christopher Hild Realty FC, LLC
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  /47

  $349,990

  $40K PRICE DROP Pending

  • 3 Beds
  • 1 Bath
  • 2,102 Sq Ft

  519 Fairmont Ave, Winchester, VA 22601

  Expect a long love affair with this home.Some homes feel like they were built with patience, pride, and a sense of permanence—and this historic Winchester beauty has that feeling the moment you step inside. Set near Old Town Winchester and positioned right next to the approved Cider Hill Neighborhood Design District, it offers something rare: preserved historic character today, with a

  Hannah Won Samson Properties

  519 Fairmont Ave, Winchester, VA 22601
• 

  

  /10

  $1,200

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 1,200 Sq Ft
  • Condo for Rent

  316 S Cameron St Unit 3, Winchester, VA 22601

  Three block from Winchester walking mall / One bedroom/ one bath/ off street parking/ ground floor unit

  316 S Cameron St Unit 3, Winchester, VA 22601
• 

  

  /28

  $580,000

  Sold Oct 24, 2025

  230 W Boscawen St, Winchester, VA 22601

  • 7,650 Sq Ft
  • Built 1891

  Last Sold Summary

  • $76/SF
  • 284 Days On Market

  Current Estimated Value $589,981

  Last Listing Agent Gillian Greenfield Coldwell Banker Premier

  230 W Boscawen St, Winchester, VA 22601
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  /63

  Not Listed For Sale

  327 Russellcroft Rd, Winchester, VA 22601

  • 3 Beds
  • 3 Baths
  • 3,873 Sq Ft
  • Built 1968

  327 Russellcroft Rd, Winchester, VA 22601

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Matt Kilmer Samson Properties
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  /52

  $399,000

  $26K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,799 Sq Ft

  437 Beechcroft Rd, Winchester, VA 22601

  PRICE REDUCED! BRICK BEAUTY ON A CORNER LOT WITH AN ATTACHED CARPORT AND A FULL BASEMENT. This remodeled and freshly painted 2-bedroom, 2-bath rancher with newly refinished hardwood floors is move-in ready. In-town convenience with nearby shopping, restaurants and services. A short drive to commuter routes 81, 37 and 50, downtown and Winchester Medical Center. Perfect for those who are downsizing

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  437 Beechcroft Rd, Winchester, VA 22601
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  /9

  $1,300

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  318 S Cameron St Unit A, Winchester, VA 22601

  Upper level apartment two minutes from the walking mall in the heart of the city! Walk to shops, restaurants or park privately in off street parking! Great location!!Pets allowed on a case by case basis and an additional $50 per pet fee per month

  318 S Cameron St Unit A, Winchester, VA 22601
• 

  

  /30

  $325,000

  Sold Oct 20, 2025

  966 Woodstock Ln, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,529 Sq Ft
  • Built 1980

  Last Sold Summary

  • $213/SF
  • 31 Days On Market

  Current Estimated Value $345,224

  Last Listing Agent Anselm Tamasang Weichert Realtors - Blue Ribbon

  966 Woodstock Ln, Winchester, VA 22601
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  /15

  Not Listed For Sale

  3136 Eton Place, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,918 Sq Ft
  • Built 2024

  3136 Eton Place, Winchester, VA 22601

  Last Sold Summary

  • 148 Days On Market

  Last Listing Agent Brittany Newman DRB Group Realty, LLC
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  /26

  $364,990

  New Construction $3K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  11 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with Lower Level Bathroom! This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free

  DRB Homes Builder

  11 Monteith Dr, Winchester, VA 22601
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  /8

  $1,900

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  2971 Valley Ave Unit 101, Winchester, VA 22601

  These units can be rented short term. All units are lofts. Livingroom, kitchen and bath on the main level with a bedroom upstairs. All utilities including internet are included. Well behaved pets are welcome! Fully furnished.

  2971 Valley Ave Unit 101, Winchester, VA 22601
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  /36

  $635,500

  Sold Nov 19, 2025

  315 W Leicester St, Winchester, VA 22601

  • 4 Beds
  • 4 Baths
  • 3,100 Sq Ft
  • Built 1923

  Last Sold Summary

  • $205/SF
  • 5 Days On Market

  Current Estimated Value $670,618

  Last Listing Agent Leigh Phillips MarketPlace REALTY

  315 W Leicester St, Winchester, VA 22601
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  /15

  Not Listed For Sale

  3142 Eton Place, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,916 Sq Ft
  • Built 2024

  3142 Eton Place, Winchester, VA 22601

  Last Sold Summary

  • 141 Days On Market

  Last Listing Agent Brittany Newman DRB Group Realty, LLC
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  /52

  $365,000

  Under Contract

  • 3 Beds
  • 3 Baths
  • 2,052 Sq Ft

  824 Appleseed Ct, Winchester, VA 22601

  Welcome home to this charming 3-bedroom duplex nestled in the highly desirable Orchard Hill neighborhood of Winchester City. Enjoy the convenience of tree-lined sidewalks, street lights, and an easy walk to Park Place Park, making this location perfect for outdoor recreation and neighborhood strolls. Inside, you'll find three finished levels designed for comfortable living. The inviting living

  Laura White ERA Oakcrest Realty, Inc.

  824 Appleseed Ct, Winchester, VA 22601
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  /62

  $1,725

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  342 Fairmont Ave Apt Unit Comfortable In-Towner, Winchester, VA 22601

  COMPLETELY FURNISHED RENTAL.Perfect for traveling professionals or students or those renovating or selling a home and are in limbo until the new home is ready. Cozy and stylish one bedroom apartment in the heart of downtown, historic Winchester. This completely furnished apartment has everything you need for a short or extended stay. Linens, pots, pans, plates, glasses, utensils,

  342 Fairmont Ave Apt Unit Comfortable In-Towner, Winchester, VA 22601
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  /116

  $537,500

  Sold Jan 08, 2026

  510 S Washington St, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 2,874 Sq Ft
  • Built 1920

  Last Sold Summary

  • $187/SF
  • 14 Days On Market

  Current Estimated Value $590,305

  Last Listing Agent Laurie Webber Century 21 Modern Realty Results

  510 S Washington St, Winchester, VA 22601
• 

  

  /22

  Not Listed For Sale

  3146 Eton Place, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,928 Sq Ft
  • Built 2024

  3146 Eton Place, Winchester, VA 22601

  Last Sold Summary

  • 51 Days On Market

  Last Listing Agent Brittany Newman DRB Group Realty, LLC
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  /46

  $1,150,000

  • 5 Beds
  • 5 Baths
  • 5,695 Sq Ft

  801 Armistead St, Winchester, VA 22601

  This home has a 2.25% VA Assumable Loan. There are homes that simply provide shelter. And then there are homes like this—homes that make you slow down, take a deep breath, and picture the life you've been working so hard to create. Nestled in one of Winchester's most beloved neighborhoods, this stately residence blends timeless elegance with the confidence that comes from knowing the important

  Donna Chong Samson Properties

  801 Armistead St, Winchester, VA 22601
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  /14

  $2,100

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Condo for Rent

  342 Fairmont Ave Unit 3, Winchester, VA 22601

  Gorgeous, large, fully furnished two bedroom apartment.Amazing location in beautiful well-established neighborhood. Just two short walking blocks to the Old Town Winchester pedestrian mall with shops, restaurants, cafes and entertainment.Located inside an 1840s hstoric house, this two bedroom apartment features original hardwood floors, high ceilings, crown molding, large windows,

  342 Fairmont Ave Unit 3, Winchester, VA 22601
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  /47

  $295,000

  Sold Nov 03, 2025

  2964 Grace St, Winchester, VA 22601

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft
  • Built 1955

  Last Sold Summary

  • $378/SF
  • 22 Days On Market

  Current Estimated Value $307,752

  Last Listing Agent Jane Norton United Real Estate Premier

  2964 Grace St, Winchester, VA 22601
• 

  

  /22

  Not Listed For Sale

  3132 Eton Place, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,074 Sq Ft
  • Built 2024

  3132 Eton Place, Winchester, VA 22601

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Brittany Newman DRB Group Realty, LLC
• 

  

  /7

  $1,100,000

  Under Contract

  • 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
• 

  

  /10

  $1,395

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  2640 Valley Ave Unit All Utilities Included, Winchester, VA 22601

  If interested, please call, we do not respond to email or requests. 1 Bedroom 1 Bath 600 sqft. $1395/Month 1 Year Lease. All Utilities Included. First and Security Due at Signing. Stove, dishwasher, fridge, washer, and dryer provided inside unit. Individual Unit Central heat and air. No Smoking. No Pets. $35 Application Fee. Meticulously

  2640 Valley Ave Unit All Utilities Included, Winchester, VA 22601
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  /45

  $500,000

  Sold Oct 15, 2025

  436 W Leicester St, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,592 Sq Ft
  • Built 1925

  Last Sold Summary

  • $314/SF

  Current Estimated Value $520,716

  Last Listing Agent Jeanne Mezzatesta Colony Realty

  436 W Leicester St, Winchester, VA 22601
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  /41

  Est $506,845

  Not Listed For Sale

  2060 Taylor Grace Ct, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 1,776 Sq Ft
  • Built 2011

  2060 Taylor Grace Ct, Winchester, VA 22601

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Paul Gallagher Colony Realty
• 

  

  /55

  $299,990

  $11K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,474 Sq Ft

  406 Highland Ave, Winchester, VA 22601

  HERE IS YOUR CHANCE! BACK ON THE MARKET DUE TO NO FAULT OF THE SELLERS!!DIRECTIONS FOR PARKING; FROM NAT AVE TAKE RIGHT ON ATHEY ALLY TO 4 CAR PARKING AREA ON LEFT - LOOK FOR 406 MARKER. Located in The Historic Old Town Winchester area with private parking right off of Athey Alley, we are happy to list this nicely remodeled 2 story circa 1930s, center hall home.. Since the purchase of this

  Lisette Turner Century 21 Redwood Realty

  406 Highland Ave, Winchester, VA 22601
• 

  

  /53

  $1,800

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft
  • Condo for Rent

  21 N Braddock St, Winchester, VA 22601

  Located in Historic Downtown Winchester on North Braddock Street- 1 block west of Walking Mall. Restaurants, shops, transportation all within walking distance.Hardwood floors throughout historic property, large open rooms, 9' ceilings. 1 of 4 units total in building. Second Floor. No Pets/No Smoking. Large Kitchen features Stove, Microwave, Oven, Full size Fridge -AND a large walk-in

  21 N Braddock St, Winchester, VA 22601
• 

  

  /30

  $329,400

  Sold Aug 08, 2025

  613 Watson Ave, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 1,668 Sq Ft
  • Built 1946

  Last Sold Summary

  • $197/SF
  • 4 Days On Market

  Current Estimated Value $333,192

  Last Listing Agent Teri Domanski Your Home Sold Guaranteed Realty - East LLC

  613 Watson Ave, Winchester, VA 22601
• 

  

  /43

  Est $598,321

  Not Listed For Sale

  2044 Taylor Grace Ct, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,568 Sq Ft
  • Built 2011

  2044 Taylor Grace Ct, Winchester, VA 22601

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Cynthia Lee RE/MAX Roots
• 

  

  /36

  $320,000

  • 3 Beds
  • 3 Baths
  • 1,281 Sq Ft

  115 S Purcell Ave, Winchester, VA 22601

  Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018. Open House on Sunday, August 16th from 1-4pm.

  Matthew Berry MarketPlace REALTY

  115 S Purcell Ave, 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
• 

  

  /35

  $270,000

  Sold Mar 03, 2026

  239 Chestnut St, Winchester, VA 22601

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft
  • Built 1976

  Last Sold Summary

  • $230/SF
  • 100 Days On Market

  Current Estimated Value $282,673

  Last Listing Agent William Wertz Wildhawks Realty LLC

  239 Chestnut St, Winchester, VA 22601
• 

  

  /19

  Est $291,218

  Not Listed For Sale

  521 1/2 N Loudoun St, Winchester, VA 22601

  • 4 Beds
  • 1.5 Baths
  • 1,277 Sq Ft
  • Built 1936

  521 1/2 N Loudoun St, Winchester, VA 22601

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Barton Chasler Realty ONE Group Old Towne
• 

  

  /9

  $150,000

  Under Contract

  • Land
  • 18,295 Sq Ft
  • $357,143 per Acre

  1322 Vanceright Cir, Winchester, VA 22601

  Tucked away on a quiet cul-de-sac, this 0.4174-acre lot offers a fantastic opportunity to build your dream home in a highly desirable Winchester location. Enjoy the convenience of being just minutes from Handley High School and the charm, dining, and shopping of downtown Winchester. The property features a 30' easement, allowing for access while still providing ample space for your vision. With

  John Scully Colony Realty

  1322 Vanceright Cir, Winchester, VA 22601
• 

  

  /23

  $2,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Condo for Rent

  210 E Boscawen St Unit 200, Winchester, VA 22601

  This two bedroom and two bath apartment has lots of natural light with windows spanning two sides of the building (window treatments already installed). The convenient location is just two blocks from the old town walking mall! Easy to clean and maintain LVP flooring has been installed throughout. The kitchen features ample cabinet space with plenty of drawers for easy organizing, and stainless

  Katie Landi Jordan Samson Properties

  210 E Boscawen St Unit 200, Winchester, VA 22601
• 

  

  /40

  $449,990

  Sold Aug 12, 2025

  1827 Reese Ct, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 1,923 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $234/SF
  • 6 Days On Market

  D.R. Horton Abrams Crossing at Meadow Branch

  1827 Reese Ct, Winchester, VA 22601
• 

  

  /24

  Est $357,944

  Not Listed For Sale

  456 Imperial St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,722 Sq Ft
  • Built 1962

  456 Imperial St, Winchester, VA 22601

  Last Sold Summary

  • 76 Days On Market

  Last Listing Agent Holly Porter NewTown Realty

Showing Results 121 - 160, Page 4 of 18