Winchester, VA Homes

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  /5

  $250,000

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

  21 E Germain St, Winchester, VA 22601

  Charming 3-Bedroom Home in Historic Winchester, Virginia Discover this beautifully located 3-bedroom, 2-full bath home nestled in the heart of Historic Winchester. This residence boasts an exceptional location, just a short stroll away from the Old Town Mall, allowing you to enjoy local shops and dining. Positioned along the scenic Apple Blossom parade route, this home is perfect for anyone

  

  Corey Morgan

  CENTURY 21 Envision

  (540) 802-5749

  21 E Germain St, Winchester, VA 22601
• Explore Winchester

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  /7

  $1,200 per month

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

  24 W Cecil St, Winchester, VA 22601

  Charming Old Town location! Nestled in the heart of historic Old Town, this refreshed two-bedroom apartment offers an ideal urban living experience. The spacious layout is filled with natural light, with large windows creating a bright and airy atmosphere throughout. Conveniently located near shops, dining, and entertainment. Lease Requirements:Good credit and clean background check required.

  

  Frank Armstrong, IV

  Colony Realty

  (540) 701-4871

  24 W Cecil St, Winchester, VA 22601
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  /7

  $2,500 Sold Mar 26, 2025

  Lot 22 Marlin Dr, Winchester, VA 22602

  • Land
  • 0 Acre

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Kaitlyn Behr Samson Properties

  Lot 22 Marlin Dr, Winchester, VA 22602
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  /5

  Not Listed For Sale

  • Studio
  • 3,032 Sq Ft

  378 National Ave, Winchester, VA 22601

  378 National Ave, Winchester, VA 22601
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  /29

  $295,000

  • 3 Beds
  • 1 Bath
  • 1,325 Sq Ft

  312 Shawnee Ave, Winchester, VA 22601

  Within walking distance to Historic Downtown Winchester! Public record square footage was found to be inaccurate - listing square footage has been adjusted and price adjusted accordingly. This home is convenient to everything happening in Winchester and also a very easy location for commuters. Nestled in the charming Shawnee Heights neighborhood, this delightful cottage-style home offers a

  

  Lori Bales

  Keller Williams Realty

  (540) 209-9771

  312 Shawnee Ave, Winchester, VA 22601
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  /5

  $1,000 per month

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

  318 S Braddock St Unit 3, Winchester, VA 22601

  Large 1-bedroom, 1-bathroom apartment located in the heart of Downtown Winchester, just steps from the Old Town Mall. This unit has been newly refreshed and is move-in ready. Convenient walkable location near shopping, dining, and entertainment. Rental Requirements:Tenant must have good credit and pass a clean background check. Restrictions:No smoking. No pets. No vaping.

  

  Frank Armstrong, IV

  Colony Realty

  (540) 924-1612

  318 S Braddock St Unit 3, Winchester, VA 22601
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  /4

  $190,000 Sold Nov 25, 2025

  303 Barrington Ln, Winchester, VA 22601

  • 2 Beds
  • 1 Bath
  • 894 Sq Ft
  • Built 1994

  Last Sold Summary

  • $213/SF
  • 86 Days On Market

  Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.

  303 Barrington Ln, Winchester, VA 22601
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  /45

  Est $424,011 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,157 Sq Ft

  97 Molden Dr, Winchester, VA 22601

  97 Molden Dr, Winchester, VA 22601
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  /15

  $55,000

  • Land
  • 1.3 Acres
  • $42,308 per Acre

  LOT 152 Bobcat Trail, Winchester, VA 22602

  This lot is your perfect building spot if you are looking for the best views! Overlooking the mountain and plenty of semi cleared softly, sloped land, this lot is already perked for a 3 bedroom home and well site located. Originally three separate lots, it has been combined into a 1.3acre lot and is waiting for you to build your mountain retreat on.

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 782-3211

  LOT 152 Bobcat Trail, Winchester, VA 22602
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  /8

  $2,400 per month

  • 4 Beds
  • 3.5 Baths
  • 1,960 Sq Ft
  • Townhouse for Rent

  1801 Harvest Dr, Winchester, VA 22601

  Brand new and move-in ready, this attractive three-level end-unit townhome at 1801 Harvest Drive offers modern living in a fantastic Winchester location. Featuring a full brick front and additional sound insulation, this end unit provides both style and comfort. The entry level includes a one-car garage, a private bedroom, and a full bathroom, perfect for guests, a home office, or flexible living

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 619-5461

  1801 Harvest Dr, Winchester, VA 22601
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  /57

  $625,000 Sold Oct 31, 2025

  101 Arthur Ln, Winchester, VA 22602

  • 5 Beds
  • 3.5 Baths
  • 4,787 Sq Ft
  • Built 2007

  Last Sold Summary

  • $131/SF
  • 5 Days On Market

  Last Listing Agent Scotti Sellers Compass

  101 Arthur Ln, Winchester, VA 22602
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  /36

  Est $401,776 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,114 Sq Ft

  125 Fox Dr, Winchester, VA 22601

  125 Fox Dr, Winchester, VA 22601
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  /30

  $285,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  1116 Opequon Ave, Winchester, VA 22601

  Discover this charming and well maintained home at 1116 Opequon Avenue, offering an excellent opportunity as a starter home or investment property. Located just minutes from Old Town Winchester, this home provides convenience, comfort, and value for under 300K. The main level features hardwood floors throughout the living spaces, three bedrooms, and a full bathroom. The full basement offers great

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 413-0030

  1116 Opequon Ave, Winchester, VA 22601
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  /14

  $1,450 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Townhouse for Rent

  735 S Kent St, Winchester, VA 22601

  This brick rowhouse with covered back patio for 2 and shared green space is on the south side of Winchester City just one block from the Green Circle Trail & within walking distance of Shenandoah University. Water, sewer, trash and lawncare are included in the monthly rent. The property offers lvp flooring, washer and dryer in unit, & central heat and air. 1 pet is considered on a case-by-case

  

  Anna Fox

  NextHome Realty Select

  (540) 384-9966

  735 S Kent St, Winchester, VA 22601
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  /19

  $335,000 Sold Feb 28, 2025

  115 Worsham Terrace, Winchester, VA 22602

  • 3 Beds
  • 2.5 Baths
  • 1,416 Sq Ft
  • Built 2011

  Last Sold Summary

  • $237/SF
  • 64 Days On Market

  Current Estimated Value $338,196

  Last Listing Agent Mohammed Amkor Adamz Realty Group, LLC.

  115 Worsham Terrace, Winchester, VA 22602
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  /80

  Est $487,698 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,152 Sq Ft

  407 Tamarack Cir, Winchester, VA 22602

  407 Tamarack Cir, Winchester, VA 22602
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  /12

  $649,880 New Construction

  • 4 Beds
  • 4.5 Baths
  • 2,853 Sq Ft

  161 Williamson Rd, Winchester, VA 22602

  The Rockford home design offers a thoughtful blend of modern functionality and classic comfort, perfect for homeowners who value both style and efficiency. With 4 bedrooms, 2 to 3 bathrooms, and 2,533 square feet of living space, the Rockford is an ideal choice for first-time buyers, growing families, or anyone looking to right-size their lifestyle.Step inside to find an inviting open-concept

  

  Maronda Homes

  Builder

  161 Williamson Rd, Winchester, VA 22602
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  /11

  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 2,500 Sq Ft
  • House for Rent

  23 S Stewart St, Winchester, VA 22601

  About 2500 sqft. of completely updated DOWNSTAIRS apartment space in Downtown Winchester. All newer appliances, repainted, refinished wood floors. Sun Room, Porch, Dining room, Living room. even has some cedar closets! What more could you ask for in the heart of downtown Winchester. Landlord pays water, sewer, and all landscaping. Tenants must have minimum 650 Credit score. NO SMOKING.. NO PETS..

  

  Frank Armstrong, IV

  Colony Realty

  (540) 698-5153

  23 S Stewart St, Winchester, VA 22601
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  /31

  $280,000 Sold May 08, 2025

  151 4 Brookland Terrace, Winchester, VA 22602

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Built 1998

  Last Sold Summary

  • $239/SF
  • 267 Days On Market

  Current Estimated Value $263,731

  Last Listing Agent Melissa Davis RE/MAX Distinctive Real Estate, Inc.

  151 4 Brookland Terrace, Winchester, VA 22602
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  /57

  Est $554,472 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,415 Sq Ft

  118 Darby Dr, Winchester, VA 22602

  118 Darby Dr, Winchester, VA 22602
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  /55

  $649,000

  • 5 Beds
  • 2.5 Baths
  • 3,420 Sq Ft

  501 Jefferson St, Winchester, VA 22601

  Welcome Home!If you’ve been searching for an updated home in a PRIME location, this is it! This stunning 5BR/3BA property has been COMPLETELY RENOVATED from top to bottom—and it shows. Step inside to an open floor plan where natural light fills the gorgeous kitchen, featuring quartz countertops, stainless steel appliances, and plenty of space to gather. The adjoining family room opens to a

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 516-3824

  501 Jefferson St, Winchester, VA 22601
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  /52

  $3,000 per month

  • 4 Beds
  • 2 Baths
  • 2,658 Sq Ft
  • House for Rent

  5452 Middle Rd, Winchester, VA 22602

  Welcome to 5452 Middle Road, a beautifully renovated farmhouse offering the perfect blend of historic charm and modern comfort, all set on a picturesque 10-acre property. Enjoy peaceful views of rolling pastures, barns, cows, and mountains, all without the upkeep of maintaining the land yourself. This thoughtfully updated home is filled with character, featuring beautiful trim work, hardwood

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 782-3894

  5452 Middle Rd, Winchester, VA 22602
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  /43

  $529,000 Sold May 14, 2025

  113 Old Wagon Rd, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 2,828 Sq Ft
  • Built 1999

  Last Sold Summary

  • $187/SF
  • 10 Days On Market

  Current Estimated Value $524,954

  Last Listing Agent Kimberly Pace EXP Realty, LLC

  113 Old Wagon Rd, Winchester, VA 22602
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  /6

  Est $273,046 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  482 Apple Valley Rd, Winchester, VA 22602

  482 Apple Valley Rd, Winchester, VA 22602
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  /43

  $349,900 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,608 Sq Ft

  107 Dale Ct, Winchester, VA 22602

  HUGE PRICE DROP! JUST UNDER AN ACRE ON A CUL DE SAC WITH DETACHED GARAGE AND ABOVE GROUND POOL! APPRAISED AT $390K. Welcome to Heritage Hills!Tucked away on a quiet, private cul-de-sac, this property offers two lots—a .56-acre homesite plus an additional .41-acre corner lot (Tax ID: 54H 1 55)—for JUST UNDER AN ACRE of space to call your own. This 4-bedroom, 2-bath home is filled with

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 573-2596

  107 Dale Ct, Winchester, VA 22602
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  /7

  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 3,150 Sq Ft
  • Townhouse for Rent

  121 Taft Ave, Winchester, VA 22601

  Charming 2-Bedroom Apartment – Prime Location Near Shenandoah University! This well-maintained 1-level apartment features 2 bedrooms and 1 full bathroom. Enjoy the convenience of a great location—just minutes from Shenandoah University, shopping, dining, and more! WASHER and Dryer in the unit!

  

  Frank Armstrong, IV

  Colony Realty

  (540) 755-3946

  121 Taft Ave, Winchester, VA 22601
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  /89

  $595,000 Sold Aug 08, 2025

  121 Carnmore Dr, Winchester, VA 22602

  • 5 Beds
  • 4 Baths
  • 3,086 Sq Ft
  • Built 2005

  Last Sold Summary

  • $193/SF
  • 103 Days On Market

  Current Estimated Value $599,514

  Last Listing Agent Angela Duncan MarketPlace REALTY

  121 Carnmore Dr, Winchester, VA 22602
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  /29

  Est $589,253 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,011 Sq Ft

  401 Wheatfield Ln, Winchester, VA 22601

  401 Wheatfield Ln, Winchester, VA 22601
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  /39

  $269,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  423 Highland Ave, Winchester, VA 22601

  Charming Winchester Home – Don’t Let This One Slip Away! Welcome to this beautifully refreshed home in the heart of Winchester, offering exceptional value, versatility, and convenience. Thoughtfully updated throughout, this property is move-in ready while still leaving room to make it your own. Enjoy ample off-street parking for up to 8 cars with rear access from West Lane, fresh renovations,

  

  Carlos Soares

  Samson Properties

  (540) 924-3305

  423 Highland Ave, Winchester, VA 22601
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  /12

  $2,200 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

  (540) 781-1596

  21 S Stewart St Unit 4, Winchester, VA 22601
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  /18

  $644,990 Sold Sep 04, 2025

  126 Wagtail Ln, Winchester, VA 22603

  • 3 Beds
  • 2 Baths
  • 3,122 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $207/SF
  • 0 Days On Market

  Brookfield Residential Hiatt Pointe at Snowden Bridge - 55+ Single Family Homes Collection

  126 Wagtail Ln, Winchester, VA 22603
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  /72

  Est $904,934 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,412 Sq Ft

  154 Windsor Ln, Winchester, VA 22602

  154 Windsor Ln, Winchester, VA 22602
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  /11

  $61,900

  • Land
  • 0.69 Acre
  • $89,710 per Acre

  Lots 14 & 15 Glen Ridge Rd, Winchester, VA 22602

  Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 712-6303

  Lots 14 & 15 Glen Ridge Rd, Winchester, VA 22602
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  /12

  $1,700 per month

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • House for Rent

  228 Opequon Ave, Winchester, VA 22601

  coming soon- pictures will be up later today

  

  Frank Armstrong, IV

  Colony Realty

  (540) 766-5892

  228 Opequon Ave, Winchester, VA 22601
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  /7

  $3,000 Sold Mar 03, 2025

  Lot 12 Panther Dr, Winchester, VA 22602

  • Land
  • 0 Acre

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Kaitlyn Behr Samson Properties

  Lot 12 Panther Dr, Winchester, VA 22602
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  /49

  Est $340,985 Not Listed For Sale

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

  313 Pheasant Dr, Winchester, VA 22602

  313 Pheasant Dr, Winchester, VA 22602
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  /11

  $51,900

  • Land
  • 0.34 Acre
  • $152,647 per Acre

  Lot 10 Glen Ridge Rd, Winchester, VA 22602

  Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 732-7734

  Lot 10 Glen Ridge Rd, Winchester, VA 22602
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  /15

  $1,695 per month

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Condo for Rent

  157 10 Brookland Terrace Unit 10, Winchester, VA 22602

  **Showings to start Tuesday January 20th.**Welcome to 157-10 Brookland Terrace! This charming third-floor condo offers an open and airy living space with vaulted ceilings, skylights, and a cozy fireplace—perfect for relaxing. The updated kitchen features freshly painted cabinetry and newer appliances, including a refrigerator, built-in microwave, stove, dishwasher, and garbage disposal. Both

  

  Diego Abregu

  Keller Williams Realty

  (540) 252-3280

  157 10 Brookland Terrace Unit 10, Winchester, VA 22602
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  /80

  $415,000 Sold May 08, 2025

  526 N Braddock St, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,375 Sq Ft
  • Built 1927

  Last Sold Summary

  • $175/SF
  • 5 Days On Market

  Current Estimated Value $445,664

  Last Listing Agent Leah Clowser RE/MAX Roots

  526 N Braddock St, Winchester, VA 22601
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  /79

  Est $670,096 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,110 Sq Ft

  108 Pangborne Ct, Winchester, VA 22602

  108 Pangborne Ct, Winchester, VA 22602

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