Winchester, VA Homes

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  /5

  $250,000 Pending

  • 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

  $1,500 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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  /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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  /7

  Not Listed For Sale

  Lot 11 Panther Dr, Winchester, VA 22602

  Lot 11 Panther Dr, Winchester, VA 22602

  Last Sold Summary

  • 4 Days On Market

  Last Sold Price $3,000

  Last Listing Agent Kaitlyn Behr Samson Properties
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  /23

  $310,000

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft

  27 Jackson Ave, Winchester, VA 22601

  Completely renovated and move-in ready, this charming 3 bedroom, 1 bath home is ideally located just minutes from downtown Winchester's shops, dining, and entertainment. Inside, you'll find beautiful hardwood floors throughout and a brand new kitchen and fully renovated bathroom. Major updates to the home include a new roof, new windows, new HVAC system, new hot water heater and new electric all

  

  Mikiala Whitacre

  ERA Oakcrest Realty, Inc.

  (540) 590-5591

  27 Jackson 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) 318-1292

  21 S Stewart St Unit 4, 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

  Current Estimated Value $196,711

  Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.

  303 Barrington Ln, Winchester, VA 22601
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  /7

  Not Listed For Sale

  Lot 12 Panther Dr, Winchester, VA 22602

  Lot 12 Panther Dr, Winchester, VA 22602

  Last Sold Summary

  • 4 Days On Market

  Last Sold Price $3,000

  Last Listing Agent Kaitlyn Behr Samson Properties
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  /29

  $255,000 Pending

  • 1 Bed
  • 1 Bath
  • 660 Sq Ft

  1208 Rockwood Trail, Winchester, VA 22602

  * All offers must be made by 2/21 by 430pm. * Escape to your private mountain retreat in the heart of the Shenandoah Valley. This 1-bedroom, 1-bath cabin sits atop the mountain just minutes from Winchester, offering panoramic views, crisp Blue Ridge air, and some of the darkest skies in the region—perfect for stargazing.Enjoy easy access to hiking, wildlife, and scenic beauty throughout the

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 269-5294

  1208 Rockwood Trail, Winchester, VA 22602
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  /11

  $1,400 per month

  • 1 Bed
  • 1 Bath
  • 15,699 Sq Ft
  • Condo for Rent

  44 S Loudoun St Unit 9, Winchester, VA 22601

  Charming 1 bedroom, 1 bathroom apartment located on the Historic Downtown walking mall, with access to all of the Shops, restaurants, museums, and more right out the front door! Just minutes from Shenandoah University, Apple Blossom Mall, and Winchester Medical Center. Parking for each unit.

  

  Brock Harris

  Samson Properties

  (540) 516-4753

  44 S Loudoun St Unit 9, 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

  Current Estimated Value $627,639

  Last Listing Agent Scotti Sellers Compass

  101 Arthur Ln, Winchester, VA 22602
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  /5

  Not Listed For Sale

  0 Bobcat Trail Unit 2500019, Winchester, VA 22602

  0 Bobcat Trail Unit 2500019, Winchester, VA 22602

  Last Sold Summary

  • 58 Days On Market

  Last Sold Price $77,000

  Last Listing Agent Andy Austin Double A Auction & Realty
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  /36

  $365,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  127 Shirley St, Winchester, VA 22601

  Comfortable living at this split-foyer home located in the heart of the City of Winchester. On the main level, you’ll find three bedrooms and a full bath. The lower level features a fourth bedroom plus a second full bath — ideal for guests, or a home office. Location is a standout. You’re just minutes from downtown dining, shopping, and community events, and enjoy easy access to schools, parks,

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 802-5087

  127 Shirley St, Winchester, VA 22601
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  /14

  $2,200 per month

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Condo for Rent

  104 S Loudoun St Unit 2, Winchester, VA 22601

  Charming downtown living at it s best! Perfectly located directly on the Historic Downtown Walking Mall. This spacious 2 bedroom 2 bathroom condo features very own washer and dryer, stainless steel appliances, 2 assigned parking spots, HVAC and more. Shops, restaurants, museums, and more only steps from your front door. Check out convenient chic living today!

  

  Brock Harris

  Samson Properties

  (540) 596-5993

  104 S Loudoun St Unit 2, 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 $258,722

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

  151 4 Brookland Terrace, Winchester, VA 22602
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  /12

  Not Listed For Sale

  Lot 21 Cardinal Dr, Winchester, VA 22602

  Lot 21 Cardinal Dr, Winchester, VA 22602

  Last Sold Summary

  • 3 Days On Market

  Last Sold Price $8,500

  Last Listing Agent Kristin Crosby Samson Properties
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  /41

  $345,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,066 Sq Ft

  105 W Oates Ave, Winchester, VA 22601

  This beautifully updated and lovingly maintained home is located in the much loved heart of Winchester. Gleaming hardwood floors welcome you as soon as you enter and that is only the beginning! This sweet home is light filled and happy. Spacious living and dining areas with new recessed lights. The kitchen shines as well with updated lighting, new quartz countertops, sink, coffee bar and

  

  Layne Jensen

  CENTURY 21 New Millennium

  (540) 781-1560

  105 W Oates Ave, Winchester, VA 22601
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  /17

  $2,050 per month

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • House for Rent

  427 Highland Ave, Winchester, VA 22601

  Welcome to this charming single-family home featuring 3 bedrooms and 2 baths in a prime Winchester location. The home offers durable LVP flooring throughout and a modern kitchen equipped with stainless steel appliances. Enjoy the convenience of both rear parking and ample street parking. Ideally located with easy access to Routes 7 and 81 and just minutes from downtown Winchester, shopping,

  

  David Peña

  Corcoran McEnearney

  (540) 253-1314

  427 Highland Ave, Winchester, VA 22601
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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 $520,045

  Last Listing Agent Kimberly Pace EXP Realty, LLC

  113 Old Wagon Rd, Winchester, VA 22602
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  /28

  Not Listed For Sale

  303 Summerfield Dr, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 3,200 Sq Ft
  • Built 2025

  303 Summerfield Dr, Winchester, VA 22602

  Last Sold Summary

  • $259/SF
  • 0 Days On Market

  Last Sold Price $829,161

  Last Listing Agent JP Carr Merrifield Realty, LLC
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  /58

  $999,000 Open Sat 12PM - 3PM

  • 6 Beds
  • 3.5 Baths
  • 3,848 Sq Ft

  240 Glendobbin Rd, Winchester, VA 22603

  Nestled on a picturesque 7-acre lot, this Farmette is just minutes from downtown Winchester, offering the perfect blend of privacy, space, and convenience. Opportunities like this are rare—enjoy the tranquility of country living while remaining in one of the area’s most desirable and accessible locations.Inside, hardwood floors flow throughout the home, beginning with a grand entrance and

  

  Lori Bales

  Keller Williams Realty

  (540) 515-5065

  240 Glendobbin Rd, Winchester, VA 22603
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  /9

  $1,350 per month

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

  235 Kern St, Winchester, VA 22601

  Downtown Winchester location, clean and super cute! This 2 bed/1 bath duplex offers a private, fenced in backyard on the north side of town. Completely renovated in 2022. Available for immediate occupancy. Application fee $50 for everyone 18 or older, no pets, monthly income minimum of $4,050, security deposit is $1350, no previous evictions, judgements, liens, collections; credit score 620+,

  

  Anna Fox

  NextHome Realty Select

  (540) 596-5992

  235 Kern St, 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 $600,612

  Last Listing Agent Angela Duncan MarketPlace REALTY

  121 Carnmore Dr, Winchester, VA 22602
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  /35

  Not Listed For Sale

  620 Cardinal Dr, Winchester, VA 22602

  • 3 Beds
  • 2 Baths
  • 1,217 Sq Ft
  • Built 2024

  620 Cardinal Dr, Winchester, VA 22602

  Last Sold Summary

  • $263/SF
  • 55 Days On Market

  Last Sold Price $320,000

  Last Listing Agent Sheila Pack RE/MAX
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  /15

  $55,000 Pending

  • 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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  /22

  $1,450 per month

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • House for Rent

  224 1/2 Kern St Unit 224 1/2, Winchester, VA 22601

  Newly-renovated 2nd-floor unit in the heart of downtown Winchester! This 2-bedroom, 1 bath unit features a private alleyway in the back of the building that leads to the entrance and stairs to the 2nd floor. There you'll find a fully-remodeled open floor plan kitchen/living space that exits to a private balcony overlooking the street. Luxury vinyl plank flooring, recessed LED lights, fresh paint,

  

  Amy Franzen

  Pearson Smith Realty, LLC

  (540) 386-1583

  224 1/2 Kern St Unit 224 1/2, 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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  /4

  Not Listed For Sale

  110 Yurok Ct, Winchester, VA 22602

  • 5 Beds
  • 3 Baths
  • 2,415 Sq Ft
  • Built 2024

  110 Yurok Ct, Winchester, VA 22602

  Last Sold Summary

  • $207/SF
  • 7 Days On Market

  Last Sold Price $499,990

  Last Listing Agent Tracy Jennings DRH Realty Capital, LLC.
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  /55

  $649,000 Under Contract

  • 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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  /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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  /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 $434,315

  Last Listing Agent Leah Clowser RE/MAX Roots

  526 N Braddock St, Winchester, VA 22601
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  /55

  Not Listed For Sale

  155 Munsee Cir, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft
  • Built 2024

  155 Munsee Cir, Winchester, VA 22602

  Last Sold Summary

  • $222/SF
  • 110 Days On Market

  Last Sold Price $419,990

  Last Listing Agent Tracy Jennings DRH Realty Capital, LLC.
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  /40

  $640,000

  • 6 Beds
  • 3.5 Baths
  • 3,192 Sq Ft

  162 Omps Dr, Winchester, VA 22601

  This exceptional residence is nestled in a popular neighborhood in Winchester, just moments from Winchester Medical Center. With almost 4,000 square feet of refined living space, this 6-bedroom, 3.5-bath home delivers the scale, comfort, and location today’s discerning buyer expects.Designed for both elegant entertaining and everyday ease, the home features expansive living areas filled with

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 274-1014

  162 Omps Dr, Winchester, VA 22601
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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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  /11

  $272,900 Sold Nov 13, 2025

  852 Butler Ave, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,010 Sq Ft
  • Built 1994

  Last Sold Summary

  • $270/SF
  • 5 Days On Market

  Current Estimated Value $277,373

  Last Listing Agent LESLIE WEBB Long & Foster Real Estate, Inc.

  852 Butler Ave, Winchester, VA 22601
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  /55

  Not Listed For Sale

  157 Munsee Cir, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft
  • Built 2024

  157 Munsee Cir, Winchester, VA 22602

  Last Sold Summary

  • $222/SF
  • 101 Days On Market

  Last Sold Price $419,990

  Last Listing Agent Tracy Jennings DRH Realty Capital, LLC.
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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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  /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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  /43

  $355,000 Sold Aug 04, 2025

  120 Seabreeze Ln, Winchester, VA 22602

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

  Last Sold Summary

  • $183/SF
  • 7 Days On Market

  Current Estimated Value $352,245

  Last Listing Agent Bill Fritz RE/MAX Executives

  120 Seabreeze Ln, Winchester, VA 22602
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  /37

  Est $399,526 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

  • 14% Above List Price
  • $200/SF
  • 162 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Eric Kronenwetter RE/MAX

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