Winchester County, VA Homes

• 

  

  

  /25

  $177,000

  $12K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 896 Sq Ft

  313 Avon Ct, Winchester, VA 22601

  Newly remodeled 2-level townhouse located in a quiet, established neighborhood! This move-in ready home features a bright, sun-filled kitchen with a spacious eat-in dining area, two generously sized bedrooms, and 1.5 bathrooms. Enjoy the convenience of one assigned parking space directly in front of the home, plus a guest parking pass for unmarked spaces.Relax on the private rear deck or

  Ms. Sophia Alam AMN Realty, LLC.

  313 Avon Ct, Winchester, VA 22601
• 

  

  

  /20

  $424,990

  Sold Jun 18, 2026

  110 Swansong Place, Winchester, VA 22603

  • 4 Beds
  • 3.5 Baths
  • 2,094 Sq Ft
  • Built 2026

  Last Sold Summary

  • 2% Below List Price
  • $203/SF
  • 11 Days On Market

  Last Listing Agent Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  110 Swansong Place, Winchester, VA 22603
• 

  

  

  /73

  Est $596,510

  Not Listed For Sale

  903 Crestview Terrace, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,204 Sq Ft
  • Built 2006

  903 Crestview Terrace, Winchester, VA 22601

  Last Sold Summary

  • 64 Days On Market

  Last Listing Agent MARIA STRIBLING CENTURY 21 New Millennium
• 

  

  

  /6

  $230,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,112 Sq Ft

  214 Molden Dr, Winchester, VA 22601

  Investor opportunity in Winchester! This 2-bedroom, 1-bath home offers 1,112 finished square feet above grade, plus a full unfinished basement with additional space for storage, renovation, or future improvements. The home also features two fireplaces and a convenient carport.Located within the City of Winchester, this property presents an excellent opportunity for an investor, renovator, or

  Peter Knapp Real Broker, LLC

  214 Molden Dr, Winchester, VA 22601
• 

  

  

  /14

  $364,990

  Sold Oct 17, 2025

  627 Laurelwood Cir, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,442 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $253/SF
  • 31 Days On Market

  627 Laurelwood Cir, Winchester, VA 22601
• 

  

  /54

  Est $648,264

  Not Listed For Sale

  2513 Stoneridge Rd, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 3,297 Sq Ft
  • Built 2005

  2513 Stoneridge Rd, Winchester, VA 22601

  Last Sold Summary

  Last Listing Agent Dan Whitacre Colony Realty
• 

  

  /47

  $330,000

  $19K PRICE DROP Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,566 Sq Ft

  101 Locust Ave, Winchester, VA 22601

  Welcome to 101 Locust Avenue in the heart of Winchester on a spacious corner lot! This solid brick ranch home offers 3 bedrooms, 2.5 bathrooms, and comfortable one-level living with additional space in the lower level.The bright and spacious living room serves as the centerpiece of the home, featuring a large bay window that fills the space with natural light. On the main level there are

  Angela Duncan MarketPlace REALTY

  101 Locust Ave, Winchester, VA 22601
• 

  

  /51

  $431,000

  Sold May 29, 2026

  202 Russelcroft Rd, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 1996

  Last Sold Summary

  • 1% Above List Price
  • $239/SF
  • 5 Days On Market

  Current Estimated Value $422,775

  Last Listing Agent Laura White ERA Oakcrest Realty, Inc.

  202 Russelcroft Rd, Winchester, VA 22601
• 

  

  /90

  Est $680,468

  Not Listed For Sale

  953 Meadow Ct, Winchester, VA 22601

  • 4 Beds
  • 4.5 Baths
  • 4,042 Sq Ft
  • Built 2005

  953 Meadow Ct, Winchester, VA 22601

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent RoxAnn Grimes RE/MAX Roots
• 

  

  /31

  $249,900

  Pending

  • 2 Beds
  • 1 Bath
  • 833 Sq Ft

  221 Opequon Ave, Winchester, VA 22601

  Charming 2-bedroom, 1-bath bungalow just blocks from the heart of downtown Winchester! This beautifully maintained home offers the character and convenience you're looking for, with gorgeous hardwood floors, a spacious fenced yard, and inviting covered front and side porches.The bright, comfortable interior offers a functional layout with two bedrooms and one full bath, while the full

  Bradley Comstock ERA Oakcrest Realty, Inc.

  221 Opequon Ave, Winchester, VA 22601
• 

  

  /24

  $320,000

  Sold Jul 15, 2026

  1044 Orchard Ave, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Built 1950

  Last Sold Summary

  • 3% Below List Price
  • $275/SF
  • 11 Days On Market

  Current Estimated Value $319,005

  Last Listing Agent Julie Shiley Coldwell Banker Realty

  1044 Orchard Ave, Winchester, VA 22601
• 

  

  /72

  Est $659,710

  Not Listed For Sale

  938 Meadow Ct, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 4,336 Sq Ft
  • Built 2004

  938 Meadow Ct, Winchester, VA 22601

  Last Sold Summary

  Last Listing Agent Dave Spence RE/MAX Roots
• 

  

  /42

  $449,000

  • 4 Beds
  • 1.5 Baths
  • 1,932 Sq Ft

  420 W Cork St, Winchester, VA 22601

  Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, dining room and kitchen. Upstairs you will find 4 sizable bedrooms and a full bath. The top level is a

  Dan Whitacre Colony Realty

  420 W Cork St, Winchester, VA 22601
• 

  

  /46

  $430,000

  Sold Sep 03, 2026

  338 Lanny Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1968

  Last Sold Summary

  • 1% Below List Price
  • $345/SF
  • 19 Days On Market

  Current Estimated Value $455,123

  Last Listing Agent Gina Chatham Century 21 Redwood Realty

  338 Lanny Dr, Winchester, VA 22601
• 

  

  /62

  Est $688,536

  Not Listed For Sale

  2304 Stoneridge Rd, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,419 Sq Ft
  • Built 2006

  2304 Stoneridge Rd, Winchester, VA 22601

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Traci Shoberg Samson Properties
• 

  

  /86

  $554,900

  $5K PRICE DROP Under Contract

  • 2 Beds
  • 2.5 Baths
  • 2,031 Sq Ft

  411-U105 N Loudoun St Unit 105, Winchester, VA 22601

  Experience a rare opportunity to own a piece of Winchester history at The Fort, one of Old Town's most distinctive residential communities. Located just blocks from the vibrant Walking Mall, this beautifully renovated 2-bedroom, 2.5-bath condominium seamlessly blends historic character with modern luxury.Unit 105 features an open-concept floor plan with soaring ceilings, rich

  Jen Richards Samson Properties

  411-U105 N Loudoun St Unit 105, Winchester, VA 22601
• 

  

  /20

  $499,990

  Sold Oct 08, 2025

  3131 Eton Place, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,451 Sq Ft
  • Built 2023

  Last Sold Summary

  • $204/SF
  • 307 Days On Market

  Last Listing Agent Brittany Newman DRB Group Realty, LLC

  3131 Eton Place, Winchester, VA 22601
• 

  

  /23

  Est $641,461

  Not Listed For Sale

  2313 Stoneridge Rd, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,921 Sq Ft
  • Built 2005

  2313 Stoneridge Rd, Winchester, VA 22601

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Dave Spence RE/MAX Roots
• 

  

  /46

  $329,000

  $31K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  307 1/2 E Piccadilly St, Winchester, VA 22601

  Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll

  Nate Crandell HoneyWay

  307 1/2 E Piccadilly St, Winchester, VA 22601
• 

  

  /17

  $329,000

  Sold Jun 08, 2026

  2952 Grace St, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1985

  Last Sold Summary

  • $343/SF
  • 5 Days On Market

  Current Estimated Value $328,851

  Last Listing Agent Carolina Mosquera Weichert, REALTORS

  2952 Grace St, Winchester, VA 22601
• 

  

  /61

  Est $666,822

  Not Listed For Sale

  2624 Windwood Dr, Winchester, VA 22601

  • 6 Beds
  • 3.5 Baths
  • 4,768 Sq Ft
  • Built 2002

  2624 Windwood Dr, Winchester, VA 22601

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Alex Hodges Cottage Street Realty LLC
• 

  

  /57

  $599,990

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,386 Sq Ft

  112 Worsham Terrace, Winchester, VA 22602

  Situated on a desirable cul-de-sac homesite backing to community open space, this thoughtfully designed home offers the perfect blend of comfort and functionality. The main level features a spacious owner's suite, formal dining room, laundry room, powder room, and an open-concept kitchen overlooking the living and dining areas. The kitchen includes quartz countertops, an island with seating,

  Victoria Clark D R Horton Realty of Virginia LLC

  112 Worsham Terrace, Winchester, VA 22602
• 

  

  /26

  $374,990

  Sold Feb 11, 2026

  226 Monteith Dr, Winchester, VA 22601

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $210/SF
  • 25 Days On Market

  DRB Homes Village at Valor Crossing - Townhomes

  226 Monteith Dr, Winchester, VA 22601
• 

  

  /51

  Est $585,870

  Not Listed For Sale

  2628 Windwood Dr, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,919 Sq Ft
  • Built 1996

  2628 Windwood Dr, Winchester, VA 22601

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Jeff Webber Long & Foster Real Estate, Inc.
• 

  

  /51

  $349,000

  $30K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 2,592 Sq Ft

  2055 Cidermill Ln, Winchester, VA 22601

  PRICE IMPROVEMENT. OPEN HOUSE SATURDAY, SEPTEMBER 19TH 11:00 AM TO 1:00PM. Welcome home to this beautifully maintained 3-bedroom, 2-full-bath/2 half bath, end-of-row townhouse! Perfectly situated in a highly desirable, family-friendly neighborhood, step inside to find gleaming hardwood floors and large, sunlit rooms that offer plenty of space to live and entertain. The heart of the home features

  Karen O'Hare Colony Realty

  2055 Cidermill Ln, Winchester, VA 22601
• 

  

  /28

  $360,000

  Sold May 05, 2026

  101 Molden Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1963

  Last Sold Summary

  • $286/SF
  • 13 Days On Market

  Current Estimated Value $353,642

  Last Listing Agent Elizabeth Page Boxwell MarketPlace REALTY

  101 Molden Dr, Winchester, VA 22601
• 

  

  /38

  Est $440,966

  Not Listed For Sale

  2535 Middle Rd, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 1,836 Sq Ft
  • Built 1987

  2535 Middle Rd, Winchester, VA 22601

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent James King RE/MAX Roots
• 

  

  /6

  $4,500,000

  Under Contract

  • Land
  • 11.43 Acres
  • $393,701 per Acre

  801 Fairmont Ave, Winchester, VA 22601

  Unprecedented Development Opportunity, City of Winchester, 10.34 acres plus 3 SFH fronting Fairmont Ave (additional 1.09 acres). Gateway to downtown Old Town Winchester. Prime location for high density multifamily and mixed use commercial. Public utilities to site. Truly a catalyst development opportunity, located in the fast growing metropolitan area in Virginia. Voted #1 Main Street and Places

  Gillian Greenfield Coldwell Banker Premier

  801 Fairmont Ave, Winchester, VA 22601
• 

  

  /6

  $365,000

  Sold Sep 21, 2026

  1845 Rosser Ln, Winchester, VA 22601

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2002

  Last Sold Summary

  • 1% Below List Price
  • $304/SF
  • 81 Days On Market

  Current Estimated Value $367,254

  Last Listing Agent Derek Greene The Greene Realty Group

  1845 Rosser Ln, Winchester, VA 22601
• 

  

  /59

  Est $379,197

  Not Listed For Sale

  2543 Middle Rd, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,585 Sq Ft
  • Built 1989

  2543 Middle Rd, Winchester, VA 22601

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Lilly Triplett Colony Realty
• 

  

  /50

  $379,000

  Under Contract

  • 3 Beds
  • 3.5 Baths
  • 2,160 Sq Ft

  2104 Stoneleigh Dr, Winchester, VA 22601

  Situated in the charming Orchard Hill subdivision, this delightful twin home offers a perfect blend of comfort and functionality. Built in 1987, this Colonial-style residence boasts a classic brick exterior that exudes warmth and character. With over 2,000 square feet of thoughtfully designed living space, this home is ideal for those seeking a cozy retreat. As you approach the property, you'll

  Kim Hurst MarketPlace REALTY

  2104 Stoneleigh Dr, Winchester, VA 22601
• 

  

  /94

  $525,000

  Sold Dec 23, 2025

  2812 Ridgetop Ct, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 2,976 Sq Ft
  • Built 2010

  Last Sold Summary

  • $176/SF
  • 90 Days On Market

  Current Estimated Value $554,648

  Last Listing Agent Sara Duncan RE/MAX Distinctive Real Estate

  2812 Ridgetop Ct, Winchester, VA 22601
• 

  

  /44

  Est $498,574

  Not Listed For Sale

  2518 Windwood Dr, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,082 Sq Ft
  • Built 1990

  2518 Windwood Dr, Winchester, VA 22601

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Dan Whitacre Colony Realty
• 

  

  /44

  $374,990

  New Construction Pending

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

  249 Monteith Dr, Winchester, VA 22601

  END UNIT Luxury 3 level/3-bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available!***OFFERING UP TO $5K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*Explore Winchester’s new luxury townhome

  Brittany Newman DRB Group Realty, LLC

  249 Monteith Dr, Winchester, VA 22601
• 

  /2

  $670,000

  Sold Apr 28, 2026

  329 Wood Ave, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 3,336 Sq Ft
  • Built 1971

  Last Sold Summary

  • 8% Above List Price
  • $201/SF
  • 1 Day On Market

  Current Estimated Value $644,832

  Last Listing Agent Amy Capitano MarketPlace REALTY

  329 Wood Ave, Winchester, VA 22601
• 

  

  /33

  Est $511,359

  Not Listed For Sale

  621 Bittersweet Ct, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 1,976 Sq Ft
  • Built 1993

  621 Bittersweet Ct, Winchester, VA 22601

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Feletia Sharples Realty FC, LLC
• 

  

  /59

  $600,000

  • 3 Beds
  • 1.5 Baths
  • 3,483 Sq Ft

  1311 Handley Ave, Winchester, VA 22601

  Nestled in the charming City of Winchester, this delightful Colonial home, built in 1952, exudes warmth and character. With its classic brick exterior and excellent condition, this residence invites you to experience a blend of traditional elegance and modern comfort. Step inside to discover a thoughtfully designed interior featuring beautiful hardwood floors that flow seamlessly throughout. The

  Kim Hurst MarketPlace REALTY

  1311 Handley Ave, Winchester, VA 22601
• 

  

  /47

  $305,500

  Sold Mar 19, 2026

  712 Frederick Ave, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Below List Price
  • $200/SF
  • 20 Days On Market

  Current Estimated Value $314,101

  Last Listing Agent Jennifer Avery Crum Realty, Inc.

  712 Frederick Ave, Winchester, VA 22601
• 

  

  /60

  Est $559,067

  Not Listed For Sale

  2411 Windwood Dr, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 2,564 Sq Ft
  • Built 2002

  2411 Windwood Dr, Winchester, VA 22601

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Feletia Sharples Realty FC, LLC
• 

  

  /58

  $748,900

  • 5 Beds
  • 3 Baths
  • 5,430 Sq Ft

  416 Briarmont Dr, Winchester, VA 22601

  Classic all-brick home in a highly desirable Winchester location! Well maintained and thoughtfully designed, this five bedroom, three full bath home offers timeless character, spacious living areas and exceptional convenience. The main level features a gracious living room with fireplace, cozy den with fireplace and bookshelves and a primary bedroom on the main level. Four additional bedrooms

  John Schroth Colony Realty

  416 Briarmont Dr, Winchester, VA 22601

Showing Results 481 - 520, Page 13 of 18