Winchester County, VA Homes

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  /2

  $295,000

  Sold Oct 23, 2025

  616 Cedar Creek Grade, Winchester, VA 22601

  • Land
  • 1.33 Acres
  • $221,805 per Acre

  Last Sold Summary

  • 1,861 Days On Market

  Current Estimated Value $279,667

  Last Listing Agent Christopher Molden Merrifield Realty, LLC

  616 Cedar Creek Grade, Winchester, VA 22601
• 

  

  

  /29

  Est $255,206

  Not Listed For Sale

  2635 Limestone Ct, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,024 Sq Ft
  • Built 1992

  2635 Limestone Ct, Winchester, VA 22601

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Deborah Matthews ERA Oakcrest Realty, Inc.
• 

  

  

  /19

  $329,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,576 Sq Ft

  305 Smalts Cir, Winchester, VA 22601

  Currently under construction, this beautiful new home is scheduled for a December move-in, giving you the opportunity to enjoy a brand-new home without the wait in a walkable location, just steps from Old Town!This home features 3 beds, 2.5 baths, quartz countertops, stainless steel appliances, finished rec room and more! Plus, enjoy all closing costs paid with use of NVR Mortgage!

  Ryan Homes Builder

  305 Smalts Cir, Winchester, VA 22601
• 

  

  

  /49

  $535,000

  Sold Jul 01, 2026

  315 Walker St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,879 Sq Ft
  • Built 1968

  Last Sold Summary

  • 3% Above List Price
  • $186/SF
  • 1 Day On Market

  Current Estimated Value $533,552

  Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.

  315 Walker St, Winchester, VA 22601
• 

  

  

  /31

  Est $325,705

  Not Listed For Sale

  2617 Cornerstone Cir, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,012 Sq Ft
  • Built 1997

  2617 Cornerstone Cir, Winchester, VA 22601

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Sheila Pack RE/MAX Roots
• 

  

  /48

  $425,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,030 Sq Ft

  413 Superior Ave, Winchester, VA 22601

  ***Sellers offering $5k credit towards a mini-split -or- for closing cost assistance.*** This beautiful rancher sits on 0.38 acres with an expansive, level backyard that is fully fenced and shaded by gorgeous, mature trees. A large deck spans the back of the home and incorporates a charming stock-tank plunge pool with liner and filtration system, creating a fantastic space for relaxing and

  Steph Mitchell Samson Properties

  413 Superior Ave, Winchester, VA 22601
• 

  /2

  $559,900

  Sold Oct 10, 2025

  1729 Handley Ave, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 2,614 Sq Ft
  • Built 1987

  Last Sold Summary

  • $214/SF
  • 5 Days On Market

  Current Estimated Value $590,843

  Last Listing Agent Jeanne Mezzatesta Colony Realty

  1729 Handley Ave, Winchester, VA 22601
• 

  

  /42

  Est $389,818

  Not Listed For Sale

  410 Crescent Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • Built 1999

  410 Crescent Dr, Winchester, VA 22601

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Teresa Strohmeyer ERA Oakcrest Realty, Inc.
• 

  

  /13

  $125,000

  Pending

  • Land
  • 5 Acres
  • $25,000 per Acre

  0 Oak Dr, Winchester, VA 22603

  Enjoy rural living and fun on this building lot in the Westwood Terrace community. This prime building lot is located off of Pinehill Drive at the base of Hunting Ridge. Access is secured via road frontage on paved Oak Drive and graveled Day Drive. Electricity and other utilities are nearby making for cost effective hookups. This land is zoned RA and the topography ranges from mild to steep.

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Oak Dr, Winchester, VA 22603
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  /5

  $220,000

  Sold Feb 20, 2026

  21 E Germain St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,682 Sq Ft
  • Built 1900

  Last Sold Summary

  • 17% Below List Price
  • $131/SF
  • 101 Days On Market

  Current Estimated Value $375,449

  Last Listing Agent Corey Morgan CENTURY 21 Envision

  21 E Germain St, Winchester, VA 22601
• 

  

  /32

  Est $410,274

  Not Listed For Sale

  423 Crescent Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,548 Sq Ft
  • Built 1998

  423 Crescent Dr, Winchester, VA 22601

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Sharon Farinholt Realty ONE Group Old Towne
• 

  

  /25

  $250,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  1125 Conway St, Winchester, VA 22601

  Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwood floors and numerous recent updates, including a new roof, fresh interior paint, kitchen remodel, hallway and bathroom flooring, and a new stainless steel refrigerator. The deck has also been restored, providing a great spot to

  Curtis Siever NextHome Realty Select

  1125 Conway St, Winchester, VA 22601
• 

  

  /40

  $460,000

  Sold Sep 22, 2025

  116 S Pleasant Valley Rd, Winchester, VA 22601

  • 5 Beds
  • 2 Baths
  • 1,956 Sq Ft
  • Built 1930

  Last Sold Summary

  • $235/SF
  • 47 Days On Market

  Current Estimated Value $456,759

  Last Listing Agent Dan Whitacre Colony Realty

  116 S Pleasant Valley Rd, Winchester, VA 22601
• 

  

  /39

  Est $358,222

  Not Listed For Sale

  2642 Daniel Terrace, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,769 Sq Ft
  • Built 1990

  2642 Daniel Terrace, Winchester, VA 22601

  Last Sold Summary

  • 80 Days On Market

  Last Listing Agent Dave Spence RE/MAX Roots
• 

  

  /26

  $354,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,655 Sq Ft

  Adams Plan at Abrams Crossing at Meadow Branch, Winchester, VA 22601

  The Adams I townhome offers 1,889 sq. ft. of thoughtfully designed living space, featuring 4 bedrooms, 3.5 bathrooms, and a convenient 1-car front-load garage. The modern kitchen showcases quartz countertops, stainless steel appliances, a spacious island, recessed lighting, and upgraded cabinets. Enjoy the flexibility of a finished lower-level bonus space-perfect for a rec room, home office, or

  D.R. Horton Builder

  1831 Reese Ct Unit 37025140, Winchester, VA 22601
• 

  /2

  $310,000

  Sold Apr 03, 2026

  423 Shenandoah Place, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,118 Sq Ft
  • Built 1956

  Last Sold Summary

  • $277/SF
  • 5 Days On Market

  Current Estimated Value $305,103

  Last Listing Agent Phil Asper Keller Williams Realty/Lee Beaver & Assoc.

  423 Shenandoah Place, Winchester, VA 22601
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  /10

  Est $78,192

  Not Listed For Sale

  405 Crescent Dr, Winchester, VA 22601

  405 Crescent Dr, Winchester, VA 22601

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Matt Kilmer Samson Properties
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  /39

  $369,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,578 Sq Ft

  1414 S Braddock St, Winchester, VA 22601

  PRICE REDUCED $10,000. Come Check out this charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern convenience. With 2 spacious bedrooms and 2 full bathrooms, including a luxurious walk-in shower, this residence is designed for comfort. The heart of the home features a bright kitchen equipped with stainless

  Richard Kozlowski Long & Foster Real Estate, Inc.

  1414 S Braddock St, Winchester, VA 22601
• 

  /2

  $374,990

  Sold Jul 13, 2026

  221 Monteith Dr Unit HOMESITE 15, Winchester, VA 22601

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft
  • Built 2025

  Last Sold Summary

  • 9% Below List Price
  • $210/SF
  • 76 Days On Market

  Last Listing Agent Brittany Newman DRB Group Realty, LLC

  221 Monteith Dr Unit HOMESITE 15, Winchester, VA 22601
• 

  

  /29

  Est $214,371

  Not Listed For Sale

  2531 Hockman Ave, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,142 Sq Ft
  • Built 1952

  2531 Hockman Ave, Winchester, VA 22601

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Nadeem Helfer Samson Properties
• 

  

  /10

  $268,000

  $22K PRICE DROP Under Contract

  • 2 Beds
  • 1 Bath
  • 817 Sq Ft

  580 York Ave, Winchester, VA 22601

  **PRICE REDUCTION**This charming house in the heart of the City of Winchester has already been renovated, offering the perfect blend of classic charm and modern living. Featuring 2 cozy bedrooms and a full bathroom, the home is designed with comfort.Enjoy an updated kitchen and bathrooms, new appliances, and central A/C for a fresh, modern feel. The newly added front deck and

  Yoselin Mejia The Vasquez Group LLC

  580 York Ave, Winchester, VA 22601
• 

  

  /10

  $189,900

  Sold Oct 24, 2025

  11 S Euclid Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 917 Sq Ft
  • Built 1956

  Last Sold Summary

  • $207/SF
  • 6 Days On Market

  Current Estimated Value $214,191

  Last Listing Agent Matthew Altizer ANR Realty, LLC

  11 S Euclid Ave, Winchester, VA 22601
• 

  

  /49

  Est $655,944

  Not Listed For Sale

  808 Lake Dr, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,433 Sq Ft
  • Built 2010

  808 Lake Dr, Winchester, VA 22601

  Last Sold Summary

  • 159 Days On Market

  Last Listing Agent Brock Harris Samson Properties
• 

  

  /32

  $495,000

  $35K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,505 Sq Ft

  108 Morgan St, Winchester, VA 22601

  OPEN HOUSE 08/30/2026 FROM 1:00 PM - 3:00 PMWelcome to this charming historic home in Old Town Winchester. This spacious 3-bedroom Colonial blends timeless character with modern comfort in a convenient downtown location. Thoughtfully updated with today’s buyer in mind, this inviting residence offers upgraded amenities while preserving its classic appeal.Ideally situated within

  Stacey Rowe Real Broker LLC

  108 Morgan St, Winchester, VA 22601
• 

  

  /29

  $292,500

  Sold Jun 19, 2026

  1004 Allen Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,793 Sq Ft
  • Built 1965

  Last Sold Summary

  • 10% Below List Price
  • $163/SF
  • 18 Days On Market

  Current Estimated Value $299,657

  Last Listing Agent Chris Roszko Colony Realty

  1004 Allen Dr, Winchester, VA 22601
• 

  

  /61

  Est $669,999

  Not Listed For Sale

  708 Lake Dr, Winchester, VA 22601

  • 5 Beds
  • 4 Baths
  • 3,802 Sq Ft
  • Built 2010

  708 Lake Dr, Winchester, VA 22601

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent James King RE/MAX Roots
• 

  

  /42

  $425,000

  $25K PRICE DROP Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  703 S Loudoun St, Winchester, VA 22601

  ***4.25% INTEREST RATE AVAILABLE*** Located in the heart of Winchester’s Historic District, this remarkable property offers a rare opportunity to own a piece of the city’s rich architectural heritage just moments from vibrant Old Town Winchester. Blending timeless character with flexible living options, the home showcases classic historic charm paired with thoughtful updates that support today’s

  John Ginty Samson Properties

  703 S Loudoun St, Winchester, VA 22601
• 

  

  /45

  $440,000

  Sold Aug 07, 2026

  3137 Eton Place, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,293 Sq Ft
  • Built 2023

  Last Sold Summary

  • 13% Below List Price
  • $192/SF
  • 172 Days On Market

  Last Listing Agent Laura White ERA Oakcrest Realty, Inc.

  3137 Eton Place, Winchester, VA 22601
• 

  

  /51

  Est $758,719

  Not Listed For Sale

  921 Kennedy Dr, Winchester, VA 22601

  • 5 Beds
  • 4.5 Baths
  • 4,625 Sq Ft
  • Built 2008

  921 Kennedy Dr, Winchester, VA 22601

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Julie Shiley Coldwell Banker Realty
• 

  

  /40

  $359,000

  • 3 Beds
  • 1.5 Baths
  • 1,710 Sq Ft

  812 Appleseed Ct, Winchester, VA 22601

  Nestled on a quiet cul-de-sac surrounded by mature trees in the highly desirable Orchard Hills Subdivision with no HOA fees or restrictions, this traditional all-brick home features 3 bedrooms, 1.5 bathrooms, a 2-car driveway, and three beautifully finished levels of move-in-ready living space. From the tree-lined sidewalks and charming street lighting, you are welcomed onto a main level boasting

  Feletia Sharples Realty FC, LLC

  812 Appleseed Ct, Winchester, VA 22601
• 

  

  /33

  $419,990

  Sold Mar 18, 2026

  1809 Harvest Dr, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 1,939 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • 6% Below List Price
  • $217/SF
  • 13 Days On Market

  D.R. Horton Abrams Crossing at Meadow Branch

  1809 Harvest Dr, Winchester, VA 22601
• 

  

  /67

  Est $669,701

  Not Listed For Sale

  937 Kennedy Dr, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,887 Sq Ft
  • Built 2009

  937 Kennedy Dr, Winchester, VA 22601

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Matt Kilmer Samson Properties
• 

  

  /26

  $374,990

  New Construction

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

  HOMESITE 8 Monteith Dr, Winchester, VA 22601

  Open House this Saturday & Sunday from 2-4 PM!End of Row Townhome with 3 Bedrooms & 3.5 Bathrooms! All Three Levels Finished! Explore Winchester’s new luxury townhome community. This three level end unit home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with

  DRB Homes Builder

  HOMESITE 8 Monteith Dr, Winchester, VA 22601
• 

  

  /27

  $342,000

  Sold Jan 21, 2026

  309 W Tevis St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,419 Sq Ft
  • Built 1995

  Last Sold Summary

  • 2% Below List Price
  • $241/SF
  • 21 Days On Market

  Current Estimated Value $363,112

  Last Listing Agent Matthew Altizer ANR Realty, LLC

  309 W Tevis St, Winchester, VA 22601
• 

  

  /69

  Est $712,172

  Not Listed For Sale

  920 Kennedy Dr, Winchester, VA 22601

  • 5 Beds
  • 3.5 Baths
  • 3,677 Sq Ft
  • Built 2008

  920 Kennedy Dr, Winchester, VA 22601

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Stephanie Ryall Realty ONE Group Old Towne
• 

  

  /49

  $320,000

  • 4 Beds
  • 2 Baths
  • 2,034 Sq Ft

  410 S Cameron St, Winchester, VA 22601

  Step into a home where timeless character and modern opportunity come together. This spacious property is filled with antique charm and unique details throughout.Featuring 4 bedrooms, 2 full bathrooms, and several versatile flex spaces, this home can easily adapt to your needs or offer increased income potential with a renovation. Enjoy the outdoor living opportunities with a private

  Heloisa Amar Samson Properties

  410 S Cameron St, Winchester, VA 22601
• 

  

  /52

  $401,290

  Sold Jan 22, 2026

  1814 Blythe Way, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $212/SF
  • 8 Days On Market

  D.R. Horton Abrams Crossing at Meadow Branch

  1814 Blythe Way, Winchester, VA 22601
• 

  

  /68

  Est $615,012

  Not Listed For Sale

  800 Kennedy Dr, Winchester, VA 22601

  • 5 Beds
  • 4 Baths
  • 2,639 Sq Ft
  • Built 2009

  800 Kennedy Dr, Winchester, VA 22601

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Cindy Greenya Keller Williams Realty
• 

  

  /17

  $225,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft

  369 Charles St, Winchester, VA 22601

  This two-story home offers classic charm with a covered front porch, fenced backyard, and upper-level balcony. Located just minutes from downtown, 369 Charles Street features a recently updated kitchen with modern cabinetry, granite countertops, and stainless steel appliances. The main level features updated flooring, while the upstairs level provides access to a private, covered balcony. Two

  Marisa Varley ERA Oakcrest Realty, Inc.

  369 Charles St, Winchester, VA 22601
• 

  

  /56

  $297,900

  Sold Dec 04, 2025

  129 E Cork St, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 935 Sq Ft
  • Built 1900

  Last Sold Summary

  • $319/SF
  • 56 Days On Market

  Current Estimated Value $299,336

  Last Listing Agent Melissa Crider Sager Real Estate

  129 E Cork St, Winchester, VA 22601

Showing Results 401 - 440, Page 11 of 18