Winchester, VA Homes

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  /36

  $485,000

  $15K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,953 Sq Ft

  111 Haida Ln, Winchester, VA 22602

  ••Welcome to The Retreat at Winding Creek, your haven in Winchester, VA, where luxury meets community living. ••Single Family * Two Level * 2528 Square Feet * 4 Bedrooms , 2.5 Baths * Two Car Garage Check out the 3D Matterport Tour! ••Why wait for a new build when you can have this stunning less than two-year-old home today? You’ll arrive just as the best parts of the neighborhood are opening up.

  

  Pamela Jones

  Long & Foster Real Estate, Inc.

  (540) 698-5940

  111 Haida Ln, Winchester, VA 22602
• Explore Winchester

• 

  

  

  /74

  Starting at $1,700 Plus Fees

  • 1 - 4 Beds

  230 Spring St, Winchester, VA 22601

  Modern designs, elegant finishes, and the most desirable amenities await you at the area's newest apartment home living destination, the Local. Our Winchester apartments come in one, two, three, and four-bedroom floorplans, each featuring spacious and adaptable layouts. Various interior extras adorn them including an open floorplan concept, walk-in closets, in-unit washers/dryers, and more. As a

  The Local

  (434) 443-7642

  

  230 Spring St, Winchester, VA 22601
• 

  

  

  /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 $199,508

  Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.

  303 Barrington Ln, Winchester, VA 22601
• 

  

  

  /55

  Not Listed For Sale

  169 Munsee Cir, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft
  • Built 2025

  169 Munsee Cir, Winchester, VA 22602

  Last Sold Summary

  • 77 Days On Market
• 

  

  

  /74

  $659,900

  $9K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,429 Sq Ft

  119 Thompson Ct, Winchester, VA 22602

  Welcome to your dream home in the highly sought-after Twin Lakes Overlook community! This stunning 4-bedroom, 3.5-bathroom brick-front colonial offers nearly 4,200 square feet of meticulously designed, finished living space across three expansive levels. The main level welcomes you with sophisticated finishes, including a dedicated study with custom built-in cabinetry and a formal dining room

  

  Jodi Cilley

  Realty ONE Group Old Towne

  (540) 730-1462

  119 Thompson Ct, Winchester, VA 22602
• 

  

  /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

  (540) 516-3301

  312 E Piccadilly St, Winchester, VA 22601
• 

  

  /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 $642,029

  Last Listing Agent Scotti Sellers Compass

  101 Arthur Ln, Winchester, VA 22602
• 

  

  /33

  Est $353,275

  Not Listed For Sale

  125 Monticello Square, Winchester, VA 22602

  • 3 Beds
  • 4 Baths
  • 1,740 Sq Ft
  • Built 2009

  125 Monticello Square, Winchester, VA 22602

  Last Sold Summary

  • 61 Days On Market
• 

  

  /66

  $450,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,530 Sq Ft

  229 Garber Ln, Winchester, VA 22602

  Welcome to 229 Garber Lane — Where Historic Charm Meets Prime Commercial Opportunity. Classic charm resides in this uniquely positioned B-2 commercially zoned property offering exceptional flexibility for renovation, redevelopment, or continued residential use. Situated on 1.65± prime acres, this property is surrounded by other B-2 zoned parcels and boasts outstanding visibility from I-81, making

  

  Jodi Cilley

  Realty ONE Group Old Towne

  (540) 515-4991

  229 Garber Ln, Winchester, VA 22602
• 

  

  /38

  Starting at $1,837 Plus Fees

  • 1 - 3 Beds

  424 Ridgewood Ln, Winchester, VA 22601

  Welcome to Meadow Branch, where luxury and convenience are standard. Our community offers beautiful 1,2 and 3 bedroom apartment homes. Community means convenience and at Meadow Branch, everything you need is nearby. We conveniently located adjacent to Winchester Medical Center and 2 miles from Old Town Winchester.

  Denstock Meadow Branch LLC

  (540) 502-3204

  

  424 Ridgewood Ln, Winchester, VA 22601
• 

  

  /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 $618,227

  Last Listing Agent Angela Duncan MarketPlace REALTY

  121 Carnmore Dr, Winchester, VA 22602
• 

  

  /80

  Est $441,402

  Not Listed For Sale

  2820 Baldwin St, Winchester, VA 22601

  • 5 Beds
  • 3 Baths
  • 3,128 Sq Ft
  • Built 1965

  2820 Baldwin St, Winchester, VA 22601

  Last Sold Summary

  • 9 Days On Market
• 

  

  /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

  (540) 974-1542

  Lot 7 Cedar Creek Grade, Winchester, VA
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  /34

  $2,100 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,369 Sq Ft
  • Townhouse for Rent

  6 E Cecil St, Winchester, VA 22601

  Charming Historic 2-Bedroom Rental Just Two Blocks from the Loudoun Street Walking Mall! Live steps from downtown in this beautifully appointed duplex featuring 2-bedrooms and an additional small office/den upstairs. The home is full of historic character and modern comfort, boasting original hardwood floors, soaring ceilings, and timeless architectural charm throughout. A dedicated dining room

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 251-7132

  6 E Cecil St, Winchester, VA 22601
• 

  

  /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
• 

  

  /37

  Est $287,505

  Not Listed For Sale

  353 Shawnee Ave, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft
  • Built 1983

  353 Shawnee Ave, Winchester, VA 22601

  Last Sold Summary

  • 24 Days On Market
• 

  

  /32

  $449,000

  • 4 Beds
  • 4.5 Baths
  • 1,913 Sq Ft

  315 National Ave, Winchester, VA 22601

  Fully reimagined for modern living while preserving its timeless charm, this stunning 1910 home in the heart of Downtown Winchester offers the perfect blend of character, luxury, and value. Completely renovated from top to bottom, every detail has been thoughtfully updated—delivering the feel of new construction within a classic architectural setting.This spacious residence features 4

  

  Carlos Soares

  Samson Properties

  (540) 787-2197

  315 National Ave, Winchester, VA 22601
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  /46

  Starting at $1,675 Plus Fees

  • 1 - 3 Beds

  1981 Randolph Place, Winchester, VA 22601

  Welcome to Stuart Hill Apartments — comfortable living in scenic Winchester, VA. Nestled in the picturesque Shenandoah Valley and just minutes from Historic Downtown Winchester, dining, shopping, Shenandoah University, and Winchester Medical Center, this well-maintained community offers spacious 1-, 2-, and 3-bedroom homes with full-size in-unit washers and dryers, generous closet space, and

  Stuart Hill

  (540) 546-6430

  

  1981 Randolph Place, Winchester, VA 22601
• 

  

  /15

  $509,990

  Sold Mar 11, 2026

  108 Carnation Way, Winchester, VA 22603

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $249/SF
  • 9 Days On Market

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

  108 Carnation Way, Winchester, VA 22603
• 

  

  /69

  Est $493,518

  Not Listed For Sale

  256 Parkway St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,028 Sq Ft
  • Built 1940

  256 Parkway St, Winchester, VA 22601

  Last Sold Summary

  • 3 Days On Market
• 

  

  /30

  $325,000

  Open Sat 10AM - 12PM Coming Soon

  • 4 Beds
  • 2 Baths
  • 1,273 Sq Ft

  629 National Ave, Winchester, VA 22601

  Beautifully charming and completely move-in ready, this updated 4-bedroom, 2-bath home offers the perfect blend of style, comfort, and functionality. Step inside to find updated flooring and an open-concept main living area designed for today's lifestyle. The heart of the home is the stunning kitchen, featuring granite countertops, white cabinetry, updated fixtures, and a spacious center island

  

  Walther Vasquez Johnson

  Samson Properties

  (540) 889-0898

  629 National Ave, Winchester, VA 22601
• 

  

  /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
• 

  

  /84

  $618,000

  Sold Jun 08, 2026

  891 Payne Rd, Winchester, VA 22603

  • 4 Beds
  • 3.5 Baths
  • 2,849 Sq Ft
  • Built 1973

  Last Sold Summary

  • 12% Below List Price
  • $217/SF
  • 33 Days On Market

  Current Estimated Value $692,116

  Last Listing Agent Angela Duncan MarketPlace REALTY

  891 Payne Rd, Winchester, VA 22603
• 

  

  /28

  Est $421,206

  Not Listed For Sale

  1203 Valley Ave, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,001 Sq Ft
  • Built 1920

  1203 Valley Ave, Winchester, VA 22601

  Last Sold Summary
• 

  

  /24

  $260,000

  $5K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,068 Sq Ft

  103 E Germain St, Winchester, VA 22601

  Welcome home to 103 E Germain St, a rare end-of-row townhouse combining the historic elegance of downtown Winchester with the modern ease of late-80s construction. Whether you are a first-time buyer looking for a move-in ready home or a savvy investor looking for a high-demand rental with excellent yield potential, this property ticks every single box. Flooded with natural light, the main level

  

  Jodi Cilley

  Realty ONE Group Old Towne

  (540) 924-1926

  103 E Germain St, Winchester, VA 22601
• 

  

  /50

  Starting at $1,856 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

  (540) 837-6802

  

  1864 Old Jube Square, Winchester, VA 22601
• 

  

  /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 $295,672

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

  852 Butler Ave, Winchester, VA 22601
• 

  

  /57

  Est $497,648

  Not Listed For Sale

  151 Morning Glory Dr, Winchester, VA 22602

  • 4 Beds
  • 2.5 Baths
  • 2,532 Sq Ft
  • Built 1992

  151 Morning Glory Dr, Winchester, VA 22602

  Last Sold Summary

  • 17 Days On Market
• 

  

  /11

  $61,900

  • Land
  • 30,056 Sq Ft
  • $89,710 per Acre

  Lots 11 & 12 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) 698-4594

  Lots 11 & 12 Glen Ridge 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

  (540) 534-4239

  21 S Stewart St Unit 2, 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
• 

  

  /44

  Not Listed For Sale

  1182 Greenwood Rd, Winchester, VA 22602

  • 2 Beds
  • 2 Baths
  • 920 Sq Ft
  • Built 1977

  1182 Greenwood Rd, Winchester, VA 22602

  Last Sold Summary

  • 48 Days On Market
• 

  

  /48

  $415,000

  • 3 Beds
  • 2.5 Baths
  • 1,970 Sq Ft

  105 Tye Ct, Winchester, VA 22602

  Enjoy townhouse living with a view at 105 Tye Ct.! This desirable end-unit townhouse overlooks the neighborhood instead of facing rows of neighboring townhomes, offering a more open and private feel. Only 3 years old, this former model home features upgraded finishes and custom touches not found in many of the other units. Featuring 3 bedrooms, 2.5 bathrooms, and a finished basement, this home

  

  Frank Armstrong, IV

  Colony Realty

  (540) 730-2203

  105 Tye Ct, Winchester, VA 22602
• 

  

  /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

  (540) 773-2474

  

  2351 Quinn Ct, Winchester, VA 22601
• 

  

  /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 $356,101

  Last Listing Agent Bill Fritz RE/MAX Executives

  120 Seabreeze Ln, Winchester, VA 22602
• 

  

  /77

  Est $436,614

  Not Listed For Sale

  137 Waterloo Ct, Winchester, VA 22602

  • 4 Beds
  • 2 Baths
  • 1,956 Sq Ft
  • Built 1949

  137 Waterloo Ct, Winchester, VA 22602

  Last Sold Summary

  • 27 Days On Market
• 

  

  /65

  $379,900

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  317 Gray Ave, Winchester, VA 22601

  Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage appeal and contemporary comfort. The home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom, along with a recently finished attic that offers flexible additional living space. The primary suite includes a beautifully

  

  Matthew Abregu

  Keller Williams Realty

  (540) 701-3590

  317 Gray Ave, Winchester, VA 22601
• 

  

  /14

  $1,350 Per Month

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

  550 N Loudoun St Unit 4, Winchester, VA 22601

  Beautifully renovated in 2022, this charming 1 bedroom, 1 bathroom apartment with bonus room or office 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 June 14, 2026. Pets are considered on a

  

  Robert Adams

  Weichert Realtors - Blue Ribbon

  (540) 503-4407

  550 N Loudoun St Unit 4, Winchester, VA 22601
• 

  

  /56

  $612,225

  Sold Mar 25, 2026

  119 Hydrangea Way, Winchester, VA 22602

  • 4 Beds
  • 3 Baths
  • 2,865 Sq Ft
  • Built 2025

  Last Sold Summary

  • $214/SF
  • 210 Days On Market

  Last Listing Agent Brooks Sears Pearson Smith Realty, LLC

  119 Hydrangea Way, Winchester, VA 22602
• 

  

  /66

  Est $730,786

  Not Listed For Sale

  125 Killaney Ct, Winchester, VA 22602

  • 5 Beds
  • 4.5 Baths
  • 4,692 Sq Ft
  • Built 2005

  125 Killaney Ct, Winchester, VA 22602

  Last Sold Summary

  • 0 Days On Market

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