Winchester, VA Homes

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  /30

  $349,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,412 Sq Ft

  2561 Apple Pie Ridge Rd, Winchester, VA 22603

  Welcome home to this beautifully updated rambler, offering comfort, character, and room to grow. The spacious front living room features gleaming hardwood floors and a large picture window that fills the space with natural light.Just off the garage, the remodeled den provides versatile living space perfect for a family room, home office, or recreation area. Recent updates include new drywall,

  

  Brock Harris

  Samson Properties

  2561 Apple Pie Ridge Rd, Winchester, VA 22603
• Explore Winchester

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  /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

  

  230 Spring St, 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 $199,768

  Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.

  303 Barrington Ln, Winchester, VA 22601
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  /29

  Not Listed For Sale

  709 Panther Dr, Winchester, VA 22602

  • 3 Beds
  • 2 Baths
  • 1,217 Sq Ft
  • Built 2025

  709 Panther Dr, Winchester, VA 22602

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Lisa Gill ERA Oakcrest Realty, Inc.
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  /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
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  /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
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  /51

  $425,000

  Sold Jun 10, 2026

  104 Van Buren Place, Winchester, VA 22602

  • 4 Beds
  • 2.5 Baths
  • 1,714 Sq Ft
  • Built 1990

  Last Sold Summary

  • 1% Above List Price
  • $248/SF
  • 6 Days On Market

  Current Estimated Value $420,528

  Last Listing Agent Leah Marabella Realty ONE Group Old Towne

  104 Van Buren Place, Winchester, VA 22602
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  /52

  Not Listed For Sale

  170 Munsee Cir, Winchester, VA 22602

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

  170 Munsee Cir, Winchester, VA 22602

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Brooks Sears Pearson Smith Realty, LLC
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  /48

  $399,900

  $15K PRICE DROP

  • 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

  105 Tye Ct, Winchester, VA 22602
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  /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

  

  424 Ridgewood Ln, 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 $633,932

  Last Listing Agent Scotti Sellers Compass

  101 Arthur Ln, Winchester, VA 22602
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  /12

  Not Listed For Sale

  124 Powhatan Trail, Winchester, VA 22602

  • 3 Beds
  • 3 Baths
  • 1,850 Sq Ft
  • Built 2025

  124 Powhatan Trail, Winchester, VA 22602

  Last Sold Summary

  • 197 Days On Market

  Last Listing Agent Jim Thomson Realty ONE Group Old Towne
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  /32

  $375,000

  $15K PRICE DROP Under Contract

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft

  151 Mccormick Cir Unit 201, Winchester, VA 22602

  Experience Effortless 55+ Living at Winchester Landing – The Sapphire by Ryan Homes Discover the perfect blend of comfort and convenience in the Sapphire model, a spacious single-level condo offering over 1,500 sq. ft. of thoughtfully designed living space. The open-concept layout seamlessly connects a modern kitchen, large island, and bright great room, creating an inviting space ideal for

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  151 Mccormick Cir Unit 201, Winchester, VA 22602
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  /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
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  /70

  $535,000

  Sold Jun 05, 2026

  3691 Green Spring Rd, Winchester, VA 22603

  • 4 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Built 1970

  Last Sold Summary

  • 7% Above List Price
  • $332/SF
  • 1 Day On Market

  Current Estimated Value $526,817

  Last Listing Agent Bailey Cooper RE/MAX Gateway

  3691 Green Spring Rd, Winchester, VA 22603
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  /14

  Est $473,999

  Not Listed For Sale

  2620 Stonegate Dr, Winchester, VA 22601

  • 5 Beds
  • 3 Baths
  • 2,974 Sq Ft
  • Built 1995

  2620 Stonegate Dr, Winchester, VA 22601

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Anthony Adamovich Key Move Properties, LLC.
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  /2

  $500,900

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft

  609 Quartzite Cir, Winchester, VA 22601

  Welcome to 609 Quartzite Circle! A beautifully maintained 4-bedroom, 3-bath home offering a spacious and functional layout designed for modern living. The main level features inviting living spaces, hardwood flooring, and an open kitchen with ample cabinetry and table space. The primary suite includes a walk-in closet and a private bath with a soaking tub, while the finished lower level provides

  

  Walther Vasquez Johnson

  Samson Properties

  609 Quartzite Cir, Winchester, VA 22601
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  Starting at $1,682

  Total Monthly Price

  • 2 - 3 Beds

  121 Fay St, Winchester, VA 22602

  Live on your own terms with Fay Street Apartments. Find the comfort and convenience you crave among our one, two, and three-bedroom residences, on our well-kept premises, and in the nearby, city of Winchester, VA in the Shenandoah Valley. The property is conveniently located near top employers like Shenandoah University and Valley Health System. Our apartments open doors to a myriad of

  Fay Street Apartments

  

  121 Fay St, Winchester, VA 22602
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  /20

  $388,990

  Sold Jul 29, 2026

  110 Sioux Loop, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • 6% Below List Price
  • $206/SF
  • 35 Days On Market

  D.R. Horton Retreat at Winding Creek - Townhomes

  110 Sioux Loop, Winchester, VA 22602
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  /68

  Est $652,647

  Not Listed For Sale

  800 Kennedy Dr, Winchester, VA 22601

  • 5 Beds
  • 4 Baths
  • 2,639 Sq Ft
  • Built 2009

  800 Kennedy Dr, Winchester, VA 22601

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Cindy Greenya Keller Williams Realty
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  /2

  $195,000

  • 3 Beds
  • 1 Bath
  • 932 Sq Ft

  150 Cedar Grove Rd, Winchester, VA 22603

  This property is being sold strictly as-is, where-is. The mobile home on the property is believed to date back to the 1960s and is in need of significant renovation. Previous occupants began updating the home but did not complete the work. The property also features a garage-style building with a work bay and office space equipped with air conditioning, offering excellent potential for storage,

  

  Frank Armstrong, IV

  Colony Realty

  150 Cedar Grove Rd, Winchester, VA 22603
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  /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
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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 $608,928

  Last Listing Agent Angela Duncan MarketPlace REALTY

  121 Carnmore Dr, Winchester, VA 22602
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  /34

  Est $604,988

  Not Listed For Sale

  720 Beehive Way, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 2,571 Sq Ft
  • Built 2006

  720 Beehive Way, Winchester, VA 22601

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Amy Emerson-Kerns Beltway Realty, LLC.
• 

  

  /13

  $274,999

  Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft

  206 Kimberly Way, Winchester, VA 22601

  Beautifully remodeled 2-bedroom, 2.5-bath townhouse that's ready for you to move right in! This home features a stunning updated kitchen with granite countertops and stainless steel appliances, along with modern finishes throughout. Major improvements include a new roof and heat pump installed in 2023, providing added comfort and peace of mind. Spacious living areas, updated bathrooms, and

  

  Frank Armstrong, IV

  Colony Realty

  206 Kimberly Way, Winchester, VA 22601
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  /55

  Starting at $1,795 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

  

  1981 Randolph Place, 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
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  /36

  Est $376,994

  Not Listed For Sale

  511 S Kent St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 1900

  511 S Kent St, Winchester, VA 22601

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Lawrence Lessin Homes By Owner, Inc.
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  /54

  $610,000

  $20K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,120 Sq Ft

  211 Flanagan Dr, Winchester, VA 22602

  Pictures coming soon. Prime Location in Raven Wing!This beautiful Colonial home offers the perfect combination of comfort, convenience, and modern updates. Located in the desirable Raven Wing community, you'll enjoy easy access to schools, shopping, restaurants, and commuter routes.Recent improvements include a new roof (2025), hot water heater (3 years old), sump pump (1.5 years old),

  

  Ned Stock

  Berkshire Hathaway HomeServices PenFed Realty

  211 Flanagan Dr, Winchester, VA 22602
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  /22

  $2,225 Per Month

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

  314 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

  314 E Piccadilly St, 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
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  /47

  Est $530,067

  Not Listed For Sale

  336 Miller St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,865 Sq Ft
  • Built 1941

  336 Miller St, Winchester, VA 22601

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Julie Teets ERA Oakcrest Realty, Inc.
• 

  

  /29

  $325,000

  • 3 Beds
  • 2.5 Baths
  • 1,220 Sq Ft

  280 Sage Cir, Winchester, VA 22603

  Rare end-unit townhome situated on one of the community's desirable homesites, backing to mature trees for exceptional privacy. This spacious three-level home offers an open-concept main level featuring a bright living room, an expansive kitchen with center island, stainless steel appliances, abundant cabinetry, and a dining area with direct access to an oversized composite deck overlooking the

  

  Charlotte Trux

  KW Metro Center

  280 Sage Cir, Winchester, VA 22603
• 

  

  /50

  Starting at $1,722

  Total Monthly Price

  • 2 - 3 Beds

  900-1024 N Braddock St, Winchester, VA 22601

  Welcome to Fort Collier Terrace, an inviting community you'll love being part of. Our apartments in Winchester, VA, come in one, two, and three-bedroom layouts that range from 800 to 1,000 square feet. Aside from the generous living quarters, you'll find everything you need to feel right at home. Located near N Cameron Street and Martinsburg Pike, you're a stone's throw away from the top dining,

  Fort Collier Terrace

  

  900-1024 N Braddock St, Winchester, VA 22601
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  /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 $637,257

  Last Listing Agent Angela Duncan MarketPlace REALTY

  891 Payne Rd, Winchester, VA 22603
• 

  

  /28

  Est $285,477

  Not Listed For Sale

  946 Franklin St, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft
  • Built 1955

  946 Franklin St, Winchester, VA 22601

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Stan Dull The Wiley Companies, Inc.
• 

  /2

  $300,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,386 Sq Ft

  361 E Piccadilly St, Winchester, VA 22601

  In the heart of Winchester with 3 bedrooms and 1 full bath. Hardwood floors, fresh paint, kitchen with granite countertops, appliances, including full-sized washer and dryer. Lots of storage and private fenced backyard. Close to amenities. You don't want to miss this one!

  

  Stacy Martin

  Keller Williams Realty/Lee Beaver & Assoc.

  361 E Piccadilly St, Winchester, VA 22601
• 

  

  /10

  $1,700 Per Month

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

  44 S Loudoun St Unit 12, Winchester, VA 22601

  Charming one-bedroom apartment in the heart of historic downtown Winchester! Located right on the Walking Mall, you’ll be surrounded by local shops, restaurants, and entertainment. This inviting apartment features a spacious living room, an updated kitchen with newer cabinets and stainless steel appliances, convenient in-unit laundry, and one assigned parking space in a private lot. Enjoy

  

  Brock Harris

  Samson Properties

  44 S Loudoun St Unit 12, 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 $294,117

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

  852 Butler Ave, Winchester, VA 22601
• 

  

  /43

  Est $355,327

  Not Listed For Sale

  205 Parkway St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,008 Sq Ft
  • Built 1971

  205 Parkway St, Winchester, VA 22601

  Last Sold Summary

  • 86 Days On Market

  Last Listing Agent Agustin Martinez Spring Hill Real Estate, LLC.

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