Winchester, VA Homes

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  /26

  $369,000

  • 3 Beds
  • 2.5 Baths
  • 1,737 Sq Ft

  614 Sherlock Trace, Winchester, VA 22601

  **Excellent Opportunity in the Heart of Winchester!** Don't miss the chance to own a well-located home in one of Winchester's most convenient areas. Situated on a quiet street, this property offers easy access to shopping, dining, schools, parks, and major commuter routes—everything that matters is just minutes away. Featuring **3 bedrooms** plus **two additional versatile rooms**, this home

  

  Carlos Soares

  Samson Properties

  614 Sherlock Trace, Winchester, VA 22601
• 

  

  

  /50

  Starting at $1,850 Plus Fees

  • 1 - 2 Beds

  2351 Quinn Ct, Winchester, VA 22601

  This new mixed-use community is centrally located in Winchester with quick access to Routes 522 and I-81. Designed for modern, convenient living, Carl's Corner features three residential buildings and a standalone commercial complex.The community offers 18 one-bedroom and 60 two-bedroom apartments, all within walking distance of shopping centers and just minutes from restaurants and

  CARLS CORNER RESIDENTIAL

  

  2351 Quinn Ct, Winchester, VA 22601
• 

  

  

  /42

  $307,000

  Sold Mar 26, 2026

  140 Mccormick Cir Unit 302, Winchester, VA 22602

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $266/SF
  • 71 Days On Market

  Last Listing Agent Karl Achstetter Keller Williams Realty

  140 Mccormick Cir Unit 302, Winchester, VA 22602
• 

  

  

  /71

  Not Listed For Sale

  331 N Braddock St, Winchester, VA 22601

  • 5 Beds
  • 6 Baths
  • 6,517 Sq Ft
  • Built 1863

  331 N Braddock St, Winchester, VA 22601

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent John Schroth Colony Realty
• 

  

  

  /42

  $289,900

  Under Contract

  • 2 Beds
  • 1 Bath
  • 1,458 Sq Ft

  102 N Purcell Ave, Winchester, VA 22601

  Charming home ideally located just minutes from the heart of historic Winchester! Whether you're looking for convenient access to shopping, dining, entertainment, or commuter routes, this home offers an exceptional location paired with valuable updates for peace of mind. Relax on the inviting covered front porch, the perfect place to enjoy your morning coffee or unwind at the end of the day. The

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  102 N Purcell Ave, Winchester, VA 22601
• 

  

  /24

  $2,225 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,260 Sq Ft
  • Townhouse for Rent

  312 E Piccadilly St, Winchester, VA 22601

  Freshly updated and just two blocks from the Old Town Pedestrian Mall — this charming downtown duplex is the perfect blend of historic character and modern comfort. Recently renovated, this 3-bedroom, 1.5-bath home features gleaming hardwood floors, beautifully updated tile bathrooms, stainless steel appliances, abundant natural light, and timeless architectural details throughout. Enjoy relaxing

  

  Jeanne Mezzatesta

  Colony Realty

  312 E Piccadilly St, Winchester, VA 22601
• 

  

  /69

  $740,000

  Sold Oct 29, 2025

  170 Green Spring Rd, Winchester, VA 22603

  • 4 Beds
  • 4 Baths
  • 2,740 Sq Ft
  • Built 1999

  Last Sold Summary

  • $270/SF
  • 13 Days On Market

  Current Estimated Value $750,434

  Last Listing Agent Kira Grubb Realty ONE Group Old Towne

  170 Green Spring Rd, Winchester, VA 22603
• 

  

  /33

  Est $394,738

  Not Listed For Sale

  658 Sherlock Trace, Winchester, VA 22601

  • 5 Beds
  • 3 Baths
  • 1,930 Sq Ft
  • Built 2003

  658 Sherlock Trace, Winchester, VA 22601

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Elcy Pereira Elcy & Co. Realty, LLC.
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  /11

  $1,499,000

  • Land
  • 2.45 Acres
  • $611,837 per Acre

  821,829,839, and 851 Fox Dr, Winchester, VA 22603

  Location Location Location! 2.45 Acres comprised of 4 Lots with 3 income producing dwellings. Site falls withing the Frederick County Comprehensive Plan for Commercial Uses. Located just off the Route 37 and Route 522 Interchange next to Sheetz and KFC. All Dwellings and Outbuildings are strictly as-is.

  

  Jim Shebest

  Coldwell Banker Realty

  821,829,839, and 851 Fox Dr, Winchester, VA 22603
• 

  

  /50

  Starting at $1,889 Plus Fees

  • 1 - 3 Beds

  1864 Old Jube Square, Winchester, VA 22601

  We've got it all at the Lofts at Jubal Square, the newest addition to the charming andhistoric Winchester cityscape. We offer a total commitment to better living, boasting largeapartments with loft and garage options, as well as amenities ideal for all those seeking anexceptional apartment lifestyle. Discover the Lofts at Jubal Square and discover what itmeans to live the good

  The Lofts at Jubal Square

  

  1864 Old Jube Square, Winchester, VA 22601
• 

  

  /65

  $670,000

  Sold Feb 03, 2026

  521 Hidden Valley Ln, Winchester, VA 22603

  • 3 Beds
  • 4 Baths
  • 2,973 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Above List Price
  • $225/SF
  • 10 Days On Market

  Current Estimated Value $669,759

  Last Listing Agent Kaitlyn Behr Samson Properties

  521 Hidden Valley Ln, Winchester, VA 22603
• 

  

  /13

  Est $258,329

  Not Listed For Sale

  2304 Front Royal Pike, Winchester, VA 22602

  • 3 Beds
  • 1 Bath
  • 1,018 Sq Ft
  • Built 1959

  2304 Front Royal Pike, Winchester, VA 22602

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Katrina Dotson EXIT Elite Realty
• 

  

  /23

  $325,000

  $50K PRICE DROP Under Contract

  • 4 Beds
  • 3 Baths
  • 1,916 Sq Ft

  317 N Kent St, Winchester, VA 22601

  Step into a world of timeless elegance and modern luxury with this stunning Colonial residence, beautifully renovated in 2015 while preserving its historic charm. Nestled in a serene setting, this detached home offers a perfect blend of classic architecture and contemporary comforts, making it an ideal retreat for those seeking an exclusive lifestyle. As you enter, you are greeted by rich

  

  Clark Smith

  Samson Properties

  317 N Kent St, Winchester, VA 22601
• 

  

  /18

  $1,550 Per Month

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

  550 N Loudoun St Unit 1, Winchester, VA 22601

  Beautifully renovated in 2022, this charming 1 bedroom, 1 bathroom apartment is located in historic Winchester and offers updated living with classic character. The apartment features access to a shared coin-operated laundry room located next door at 548 N. Loudoun St. Tenant is responsible for all utilities. Available approximately Jon or before August 14, 2026. Pets are considered on a

  

  Robert Adams

  Weichert Realtors - Blue Ribbon

  550 N Loudoun St Unit 1, Winchester, VA 22601
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  /38

  $621,490

  Sold Nov 18, 2025

  123 Hydrangea Way, Winchester, VA 22602

  • 4 Beds
  • 3 Baths
  • 1,748 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $356/SF
  • 19 Days On Market

  D.R. Horton Willow Run

  123 Hydrangea Way, Winchester, VA 22602
• 

  

  /67

  Est $629,282

  Not Listed For Sale

  162 Darby Dr, Winchester, VA 22602

  • 4 Beds
  • 4 Baths
  • 2,760 Sq Ft
  • Built 2002

  162 Darby Dr, Winchester, VA 22602

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Michael Elias Century 21 Redwood Realty
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  /27

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  601 Gray Ave, Winchester, VA 22601

  Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout. Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a

  

  Walther Vasquez Johnson

  Samson Properties

  601 Gray Ave, Winchester, VA 22601
• 

  

  /22

  Starting at $1,495

  Total Monthly Price

  • 2 - 4 Beds

  2260 Wilson Blvd, Winchester, VA 22601

  Discover the perfect blend of comfort and convenience at Blue Ridge Apartments in Winchester, VA. Our recently updated homes feature a variety of floor plans. Nestled in a pet-friendly community, you're just minutes away from Winchester's scenic spots, historic downtown, Apple Blossom Mall, and major employers. With easy access to I-81 and Route 7, the best of Winchester is always within reach.

  Blue Ridge Apartments

  

  2260 Wilson Blvd, Winchester, VA 22601
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  /56

  $545,000

  Sold Nov 07, 2025

  509 Marion St, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,691 Sq Ft
  • Built 1992

  Last Sold Summary

  • $203/SF
  • 3 Days On Market

  Current Estimated Value $568,567

  Last Listing Agent Mark Francis Real Broker LLC

  509 Marion St, Winchester, VA 22601
• 

  

  /46

  Est $438,303

  Not Listed For Sale

  105 Tucks Cir, Winchester, VA 22602

  • 3 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Built 1991

  105 Tucks Cir, Winchester, VA 22602

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Brittney Hunt Pearson Smith Realty LLC
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  /101

  $879,900

  • 5 Beds
  • 4.5 Baths
  • 3,898 Sq Ft

  243 Summerfield Dr, Winchester, VA 22602

  Immaculate custom home sitting on a half-acre lot in desirable Raven Pointe! Beautiful hardwood floors flow throughout the main level, leading into a dramatic family room with 20-foot ceilings, custom built-ins, a gas fireplace, and high windows featuring remote-controlled custom shades. The gourmet kitchen boasts granite countertops, soft-close cabinets, stainless steel appliances, double wall

  

  Paul Gallagher

  Colony Realty

  243 Summerfield Dr, Winchester, VA 22602
• 

  

  /12

  $1,500 Per Month

  • 1 Bed
  • 1 Bath
  • 9,518 Sq Ft
  • Condo for Rent

  44 S Loudoun St Unit 7, Winchester, VA 22601

  Historically charming one-bedroom apartment located on the famous downtown walking mall. Enjoy stylish living amongst shops, restaurants, museums, and parks. Only minutes to Winchester Medical Center, Shenandoah University and commuter routes

  

  Brock Harris

  Samson Properties

  44 S Loudoun St Unit 7, Winchester, VA 22601
• 

  

  /17

  $256,000

  Sold Apr 29, 2026

  136 Parkside Dr, Winchester, VA 22602

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1989

  Last Sold Summary

  • $229/SF
  • 3 Days On Market

  Current Estimated Value $255,091

  Last Listing Agent Nancy Tessman EXP Realty, LLC

  136 Parkside Dr, Winchester, VA 22602
• 

  

  /31

  Est $282,700

  Not Listed For Sale

  326 Banbury Terrace, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,212 Sq Ft
  • Built 1992

  326 Banbury Terrace, Winchester, VA 22601

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Bridget Aikens Colony Realty
• 

  

  /44

  $360,000

  Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,230 Sq Ft

  117 E Pall Mall St, Winchester, VA 22601

  Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of updates and upgrades! Updated kitchen and baths, stainless steel appliances, & a fenced in backyard! 2023 - Roof, siding, & electrical panel (and all breakers), updated kitchen and all baths, 2024 - repaired sump pump & new hot water

  

  Becky Wallace

  Pearson Smith Realty, LLC

  117 E Pall Mall St, Winchester, VA 22601
• 

  

  /33

  Starting at $1,750 Plus Fees

  • 2 Beds

  110 Bulmer Loop, Winchester, VA 22602

  Our community is perfect for those who enjoy spending time outside living a healthy, lively lifestyle by using the walking trails, outdoor common areas, and dog park, as well as for those who appreciate a home that is a retreat from the business of everyday life. We are conveniently located a few short miles from Shenandoah University, I-81, Rt. 8 and Rt. 50 in Winchester, VA. Our apartments

  Madison Village Apartments (Winchester)

  110 Bulmer Loop, Winchester, VA 22602
• 

  /2

  $270,000

  Sold Mar 20, 2026

  407 van Fossen St, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 954 Sq Ft
  • Built 1956

  Last Sold Summary

  • 4% Below List Price
  • $283/SF
  • 7 Days On Market

  Current Estimated Value $272,580

  Last Listing Agent Michele Gibson Samson Properties

  407 van Fossen St, Winchester, VA 22601
• 

  

  /43

  Est $355,841

  Not Listed For Sale

  120 Seabreeze Ln, Winchester, VA 22602

  • 3 Beds
  • 3.5 Baths
  • 1,941 Sq Ft
  • Built 2003

  120 Seabreeze Ln, Winchester, VA 22602

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Bill Fritz RE/MAX Executives
• 

  

  /9

  $1,300,000

  • Land
  • 64.91 Acres
  • $20,028 per Acre

  Lot 7 Cedar Creek Grade, Winchester, VA

  Rare opportunity to own 64+ scenic acres on the desirable west side of Winchester, VA. This preservation parcel offers one building right and features a beautiful mix of open land and partial woodland, providing both usability and privacy. Formerly an apple orchard, the property is well suited for a small farm, specialty crops, or vineyard, with potential for additional uses with an approved

  

  Lori Bales

  Keller Williams Realty

  Lot 7 Cedar Creek Grade, Winchester, VA
• 

  

  /12

  $1,900 Per Month

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  21 S Stewart St Unit 4, Winchester, VA 22601

  Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester!Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard—ideal for relaxing or entertaining. You'll also love the generous storage

  

  Frank Armstrong, IV

  Colony Realty

  21 S Stewart St Unit 4, Winchester, VA 22601
• 

  

  /61

  $770,000

  Sold Feb 25, 2026

  162 Janes Way, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 4,461 Sq Ft
  • Built 2001

  Last Sold Summary

  • $173/SF
  • 77 Days On Market

  Current Estimated Value $778,003

  Last Listing Agent Tanner Pack RE/MAX Roots

  162 Janes Way, Winchester, VA 22602
• 

  

  /43

  Est $288,927

  Not Listed For Sale

  1000 Hickory Trail, Winchester, VA 22602

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 2001

  1000 Hickory Trail, Winchester, VA 22602

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Nicole Lewis Coldwell Banker Premier
• 

  

  /3

  $350,000

  • Studio
  • 1,654 Sq Ft

  211, 213-215 E Clifford St, Winchester, VA 22601

  Exceptional investment opportunity in the heart of Winchester! This unique offering includes three income-producing rental units for one price: one duplex and one single-family home located at 211, 213, and 215 E. Clifford Street. The duplex features two separate 2-bedroom, 1-bath units, while the single-family home also offers 2 bedrooms and 1 full bath. The properties are deeded separately as

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  211, 213-215 E Clifford St, Winchester, VA 22601
• 

  

  /56

  $2,200

  Total Monthly Price

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

  1608 Laurel Grove Rd Unit Townhome Cabin, Winchester, VA 22602

  Beautiful cabin home, one bedroom, one loft are with full bed and it is fully furnished, with one full bathroom, has free included utilities, 13 minutes to Winchester and 12 minutes to I-81. Conveniently located in a beautiful and quiet country side. This rental property offers stunning views and quiet environment. We are happy to announce that all of your utilities are and will be included in

  1608 Laurel Grove Rd Unit Townhome Cabin, Winchester, VA 22602
• 

  

  /22

  $119,000

  Sold Jul 16, 2026

  1280 Bobcat Trail, Winchester, VA 22602

  • Land
  • 10 Acres
  • $11,900 per Acre

  Last Sold Summary

  • 25 Days On Market

  Current Estimated Value $157,000

  Last Listing Agent Kristin Crosby Samson Properties

  1280 Bobcat Trail, Winchester, VA 22602
• 

  

  /51

  Est $838,915

  Not Listed For Sale

  373 Greenfield Dr, Winchester, VA 22603

  • 4 Beds
  • 4 Baths
  • 3,612 Sq Ft
  • Built 1981

  373 Greenfield Dr, Winchester, VA 22603

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Jackie Douglass CENTURY 21 New Millennium
• 

  

  /3

  $675,000

  Coming Soon

  • 5 Beds
  • 3 Baths
  • 4,030 Sq Ft

  146 Stonebrook Rd, Winchester, VA 22602

  Spacious ranch home on a beautiful 1-acre lot in the highly desirable Stonebrook Farms community! Surrounded by mature trees and offering a peaceful setting, this home combines the space of country living with the convenience of being just minutes from shopping, dining, medical facilities, and all that Winchester has to offer. Designed with flexibility in mind, this home features 5 bedrooms and 3

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  146 Stonebrook Rd, Winchester, VA 22602
• 

  

  /13

  $1,500 Per Month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  21 S Stewart St Unit 2, Winchester, VA 22601

  2 Bedroom Apartment for Rent – Downtown Winchester Great 2nd-floor apartment located in downtown Winchester with 2 bedrooms and 1 bathroom. This home is just a short walk from Old Town Winchester, giving you easy access to local restaurants, shops, and entertainment. The apartment features very spacious bedrooms, a comfortable family room, and a fully enclosed back porch, perfect for relaxing or

  

  Frank Armstrong, IV

  Colony Realty

  21 S Stewart St Unit 2, Winchester, VA 22601
• 

  

  /25

  $215,000

  Sold May 15, 2026

  212 Shawnee Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 985 Sq Ft
  • Built 1966

  Last Sold Summary

  • 14% Below List Price
  • $218/SF
  • 4 Days On Market

  Current Estimated Value $236,569

  Last Listing Agent Alexander Bracke Real Broker, LLC

  212 Shawnee Ave, Winchester, VA 22601
• 

  

  /39

  Est $447,630

  Not Listed For Sale

  234 Bethel Grange Rd, Winchester, VA 22603

  • 4 Beds
  • 2 Baths
  • 1,864 Sq Ft
  • Built 1954

  234 Bethel Grange Rd, Winchester, VA 22603

  Last Sold Summary

  Last Listing Agent Cathy Durbin Crum Realty, Inc.

Showing Results 41 - 80, Page 2 of 18