Winchester County, VA Homes

• 

  

  

  /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 $241,900

  Last Listing Agent Corey Morgan CENTURY 21 Envision

  21 E Germain St, Winchester, VA 22601
• 

  

  

  /42

  Est $394,635

  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
• 

  

  

  /34

  $309,000

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,007 Sq Ft

  1026 S Kent St, Winchester, VA 22601

  Welcome home to 1026 S. Kent Street, a charming and well-maintained property that blends timeless character with thoughtful updates. Beautiful hardwood floors flow throughout the home, creating warmth and continuity in every room. The kitchen features durable Corian countertops and newer appliances, making it both functional and inviting for everyday living and entertaining. Improvements provide

  Carolyn Waymack Crum Realty, Inc.

  1026 S Kent St, Winchester, VA 22601
• 

  

  /2

  $365,000

  Sold Jun 30, 2025

  2075 Honeysuckle Ln, Winchester, VA 22601

  • 1,488 Sq Ft
  • Built 2004

  Last Sold Summary

  • $245/SF

  Current Estimated Value $364,893

  Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.

  2075 Honeysuckle Ln, Winchester, VA 22601
• 

  

  

  /39

  Est $490,496

  Not Listed For Sale

  434 Crescent Dr, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,986 Sq Ft
  • Built 1996

  434 Crescent Dr, Winchester, VA 22601

  Last Sold Summary

  • 93 Days On Market
• 

  

  /39

  $320,000

  Under Contract

  • 3 Beds
  • 1 Bath
  • 1,988 Sq Ft

  528 Battle Ave, Winchester, VA 22601

  Adorable Cape Cod in the heart of Winchester! Beautifully appointed with hardwood floors, signature arched doorways from that era adding tons of charm to this lovely home. Two main floor bedrooms, renovated and updated bath, living room with gas fireplace and brick surround, kitchen with brand new gas range, expanded space perfect for dining and entertaining with doors to the front and rear

  Beckwith Bolle Carter Braxton Preferred Properties

  528 Battle Ave, 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 $443,874

  Last Listing Agent Dan Whitacre Colony Realty

  116 S Pleasant Valley Rd, Winchester, VA 22601
• 

  

  /34

  Est $389,054

  Not Listed For Sale

  431 Crescent Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,501 Sq Ft
  • Built 1997

  431 Crescent Dr, Winchester, VA 22601

  Last Sold Summary

  • 15 Days On Market
• 

  

  /69

  $605,000

  • Studio
  • 4,396 Sq Ft

  540 Monticello St, Winchester, VA 22601

  Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location!Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers

  Laura King MarketPlace REALTY

  540 Monticello St, Winchester, VA 22601
• 

  

  /13

  $499,990

  Sold Sep 17, 2025

  3131 Eton Place, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,451 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $204/SF
  • 316 Days On Market

  3131 Eton Place, Winchester, VA 22601
• 

  

  /39

  Est $373,504

  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
• 

  

  /59

  $574,900

  • 5 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  660 Beehive Way, Winchester, VA 22601

  Enjoy city living in this spacious and light-filled home featuring 5 bedrooms and 3.5 baths. Fresh new carpeting has been installed on the upper level and in the family room, complemented by hardwood floors throughout the main living areas. The kitchen is equipped with stainless steel appliances, double ovens, and a center island—perfect for cooking and entertaining. Formal living and dining

  Traci Shoberg Samson Properties

  660 Beehive Way, Winchester, VA 22601
• 

  

  /54

  $550,000

  Sold Jul 02, 2025

  529 N Braddock St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 2,551 Sq Ft
  • Built 1927

  Last Sold Summary

  • $216/SF
  • 28 Days On Market

  Current Estimated Value $531,641

  Last Listing Agent Dana Cloud Realty ONE Group Old Towne

  529 N Braddock St, Winchester, VA 22601
• 

  

  /10

  Est $93,205

  Not Listed For Sale

  405 Crescent Dr, Winchester, VA 22601

  405 Crescent Dr, Winchester, VA 22601

  Last Sold Summary

  • 5 Days On Market
• 

  

  /26

  $369,990

  New Construction $5K PRICE DROP

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

  13 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with Deck! The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home with backing to trees for added privacy and peaceful views. Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room. This

  DRB Homes Builder

  13 Monteith Dr, Winchester, VA 22601
• 

  

  /40

  $429,900

  Sold Jul 17, 2025

  1324 Ramseur Ln, Winchester, VA 22601

  • 3 Beds
  • 3.5 Baths
  • 2,721 Sq Ft
  • Built 1992

  Last Sold Summary

  • $158/SF
  • 63 Days On Market

  Current Estimated Value $431,561

  Last Listing Agent Jeanne Mezzatesta Colony Realty

  1324 Ramseur Ln, Winchester, VA 22601
• 

  

  /49

  Est $634,341

  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
• 

  

  /40

  $353,000

  $17K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,534 Sq Ft

  323 Russelcroft Rd, Winchester, VA 22601

  Priced to reflect the need for some updating, this home offers opportunities for cosmetic improvements and personalization while remaining move-in ready for those who prefer to take on projects You've found it. 2108sf total living space. 3 bedrooms 2 full baths detached home. Detached home with 3 bedrooms and 2 full baths + bonus room on the basement full finished with a family room.This home

  Alexandra Brown Spring Hill Real Estate, LLC.

  323 Russelcroft Rd, Winchester, VA 22601
• 

  

  /40

  $449,990

  Sold Aug 28, 2025

  1815 Reese, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 1,904 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $236/SF
  • 22 Days On Market

  D.R. Horton Abrams Crossing at Meadow Branch

  1815 Reese, Winchester, VA 22601
• 

  

  /61

  Est $642,287

  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
• 

  

  /13

  $125,000

  Under Contract

  • 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
• 

  

  /31

  $310,000

  Sold Jul 25, 2025

  7 E Hart St, Winchester, VA 22601

  • 2 Beds
  • 2.5 Baths
  • 1,620 Sq Ft
  • Built 1986

  Last Sold Summary

  • $191/SF
  • 0 Days On Market

  Current Estimated Value $308,346

  Last Listing Agent Jennifer Sacco RE/MAX Roots

  7 E Hart St, Winchester, VA 22601
• 

  

  /67

  Est $662,646

  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
• 

  

  /38

  $409,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 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 $306,483

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

  423 Shenandoah Place, Winchester, VA 22601
• 

  

  /69

  Est $679,542

  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
• 

  

  /67

  $614,999

  • 5 Beds
  • 3.5 Baths
  • 4,292 Sq Ft

  974 Wayne Dr, Winchester, VA 22601

  Finally, a five-bedroom, 3.5 bath home in the city of Winchester with over 4200 sq ft of living space within minutes of Valley Health and shopping. Beautifully landscaped yard, including a vegetable garden, deck, and walkout basement. 2-zone heating and cooling, natural gas heat for the main floor and lower level, and a heat pump for the second floor.

  John Schroth Colony Realty

  974 Wayne Dr, 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 $195,832

  Last Listing Agent Matthew Altizer ANR Realty, LLC

  11 S Euclid Ave, Winchester, VA 22601
• 

  

  /62

  Est $823,683

  Not Listed For Sale

  707 Kennedy Dr, Winchester, VA 22601

  • 3 Beds
  • 3.5 Baths
  • 4,987 Sq Ft
  • Built 1984

  707 Kennedy Dr, Winchester, VA 22601

  Last Sold Summary

  • 52 Days On Market
• 

  

  /40

  $429,000

  Coming Soon

  • Studio
  • 700 Sq Ft

  406-408 S Cameron St, Winchester, VA 22601

  Opportunity is knocking! This 3-unit multifamily property is centrally located in downtown Winchester, just minutes from the Walking Mall. The property is fully occupied and offers immediate rental income with strong upside potential. The property currently has a long term tenants with leases as follows: One month-to-month tenant , One tenant with a lease ending June 5, 2026 , One tenant with a

  Heloisa Amar Samson Properties

  406-408 S Cameron 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 $352,889

  Last Listing Agent Chris Roszko Colony Realty

  1004 Allen Dr, Winchester, VA 22601
• 

  

  /24

  Est $449,757

  Not Listed For Sale

  609 Quartzite Cir, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft
  • Built 2000

  609 Quartzite Cir, Winchester, VA 22601

  Last Sold Summary

  • 6 Days On Market
• 

  

  /44

  $459,000

  $10K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  1423 Greystone Terrace, Winchester, VA 22601

  Welcome to effortless in-town living on Greystone Terrace! This classic all-brick home blends timeless charm with modern comfort in an unbeatable walkable location— to downtown, local coffee shops, parks, and dining. Commuters will love the easy access to major routes, retail, and shopping! Inside, sunlight dances across rich hardwood floors that run throughout. An airy, open-flow layout

  Richard Butcher Coldwell Banker Premier

  1423 Greystone Terrace, Winchester, VA 22601
• 

  

  /8

  $160,000

  Sold Sep 08, 2025

  2812 Saratoga Dr, Winchester, VA 22601

  • Land
  • 15,681 Sq Ft
  • $444,444 per Acre

  Last Sold Summary

  • 44 Days On Market

  Current Estimated Value $159,333

  Last Listing Agent Dave Spence RE/MAX Roots

  2812 Saratoga Dr, Winchester, VA 22601
• 

  

  /41

  Est $452,458

  Not Listed For Sale

  610 Quartzite Cir, Winchester, VA 22601

  • 3 Beds
  • 3 Baths
  • 2,002 Sq Ft
  • Built 1998

  610 Quartzite Cir, Winchester, VA 22601

  Last Sold Summary

  • 20 Days On Market
• 

  

  /10

  $290,000

  • 2 Beds
  • 1 Bath
  • 817 Sq Ft

  580 York Ave, Winchester, VA 22601

  This charming bungalow in the heart of the City of Winchester has already been beautifully 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 and functionality in mind. Enjoy an updated kitchen and bathrooms, new appliances, and central A/C for a fresh, modern feel. The newly added front deck

  Yoselin Mejia The Vasquez Group LLC

  580 York Ave, 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
• 

  

  /37

  Est $402,966

  Not Listed For Sale

  2671 Daniel Terrace, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,754 Sq Ft
  • Built 1997

  2671 Daniel Terrace, Winchester, VA 22601

  Last Sold Summary

  • 162 Days On Market
• 

  

  /41

  $450,000

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

  703 S Loudoun St, Winchester, VA 22601

  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 lifestyle. Inside the main

  John Ginty Samson Properties

  703 S Loudoun St, 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 $348,291

  Last Listing Agent Matthew Altizer ANR Realty, LLC

  309 W Tevis St, Winchester, VA 22601

Showing Results 441 - 480, Page 12 of 18