Winchester, VA Homes

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  $54,900

  • Land
  • 0.73 Acre
  • $75,205 per Acre

  LOTS 7 & 8 Manor Dr, Winchester, VA 22602

  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 someone who wants to be in a community, but still have some space between neighbors. Lots 7 & 8 are being sold

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 565-5562

  LOTS 7 & 8 Manor Dr, Winchester, VA 22602
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  /7

  $995 per month

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

  1816 Valley Ave Unit 3, Winchester, VA 22601

  We are okay with Short term or Yearly lease.Freshly Remodeled Studio Apartment available. Centered in the heart of Winchester, walking distance to shops, restaurants, and entertainment. Utilities and WIFI are included at no charge. No pets allowed. Come and enjoy all of what Winchester has to offer. $995 per Month or $275 per Week. Handicap Ramp for easily access to the unit. On-site

  Raj Patel Ikon Realty - Ashburn

  1816 Valley Ave Unit 3, Winchester, VA 22601
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  /44

  $515,000 Sold Nov 21, 2025

  • 2,368 Sq Ft
  • $217/SF
  • 67 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1989

  420 Westside Station Dr, Winchester, VA 22601

  Location Location. This is not your standard cookie cutter home. This meticulously maintained contemporary home is minutes from Winchester Medical Center and less than a mile to Rt. 37. Hardwood floors throughout the property. Beautiful new deck overlooks spacious backyard that backs to trees. Property offers a living room that serves as a perfect office. Kitchen features granite counters and

  Kelly Bauer Coldwell Banker Premier

  420 Westside Station Dr, Winchester, VA 22601
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  /45

  Est $360,096 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,470 Sq Ft

  121 W Virginia Pkwy, Winchester, VA 22601

  121 W Virginia Pkwy, Winchester, VA 22601
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  /3

  $674,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,954 Sq Ft

  Lot 23 Williamson, Winchester, VA 22602

  The Drexel home design is a spacious and versatile single-family home designed to suit a variety of lifestyles. With 3,213 finished square feet, the Drexel offers generous living space that can be customized to meet your needs. It features main-level living with three bedrooms, including a private master suite with a walk-in closet and en-suite bathroom, along with two full bathrooms and a 2-car

  

  Maronda Homes

  Builder

  Lot 23 Williamson, Winchester, VA 22602
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  $1,050 - $1,300 per month

  North Winchester Apartments

  1 - 2 Beds

  800 Thomas Ct, Winchester, VA 22601

  Now Leasing: 1 & 2 Bedroom Apartments Available Now! In-unit washer and dryerWater and garbage includedEnjoy a serene, peaceful settingDon't miss out—these are first come, first serve!

  800 Thomas Ct, Winchester, VA 22601
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  /69

  $340,000 Sold Nov 21, 2025

  • 1,293 Sq Ft
  • $263/SF
  • 66 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1942

  301 Liberty Ave, Winchester, VA 22601

  Welcome to 301 Liberty Ave, FALL IN LOVE with this charming all brick colonial residence situated in the heart of downtown Winchester. Just blocks away from the scenic walking mall you’ll discover an array of quaint shops, restaurants and the renowned Apple Blossom Parade route. This meticulously fully remodeled home boasts three spacious bedrooms and two luxurious bathrooms and is ready for a

  John Ashton Equity Realty

  301 Liberty Ave, Winchester, VA 22601
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  /66

  Est $604,072 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,930 Sq Ft

  3392 Back Mountain Rd, Winchester, VA 22602

  3392 Back Mountain Rd, Winchester, VA 22602
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  /10

  $619,880 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,191 Sq Ft

  107 Malbec 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

  107 Malbec Rd, Winchester, VA 22602
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  /17

  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,004 Sq Ft
  • Townhouse for Rent

  121 Longstreet Ave, Winchester, VA 22603

  3br 2bath single level duplex located minutes from I81 and route 7. Hardwood flooring throughout with vinyl plank flooring in bathrooms and kitchen. Washer and dryer hookup. Requirements to qualify: (1) minimum $90k annual household income, (2) Good credit, (3) Good Landlord reference Please contact listing agent for application. $47 application fee per applicant

  Courtney Spaid Crum Realty, Inc.

  121 Longstreet Ave, Winchester, VA 22603
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  /58

  $644,000 Sold Nov 21, 2025

  • 4,144 Sq Ft
  • $155/SF
  • 69 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1988

  108 Katie Ln, Winchester, VA 22602

  Big price drop! Bring all offers!Welcome to 108 Katie Lane in beautiful Stonebrook Farms. This classic brick home has space, charm, and a setting that feels like home the moment you pull up. With five large bedrooms, including a comfortable primary suite, there is room for everyone. The main level features an open floor plan with hardwood floors throughout, creating a warm and welcoming feel.

  Sharon Farinholt Realty ONE Group Old Towne

  108 Katie Ln, Winchester, VA 22602
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  /5

  Est $190,389 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,508 Sq Ft

  197 Dairy Corner Place, Winchester, VA 22602

  197 Dairy Corner Place, Winchester, VA 22602
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  /11

  $624,880 New Construction

  • 2 Beds
  • 2 Baths
  • 2,658 Sq Ft

  159 Williamson Rd, Winchester, VA 22602

  

  Maronda Homes

  Builder

  159 Williamson Rd, Winchester, VA 22602
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  /17

  $500 - $2,000 per month

  Brookfield Corporate Apartments

  1 - 2 Beds

  548 Brookfield Dr, Winchester, VA 22601

  We are excited to share that we are under new ownership and management, and we're eager to welcome new guests to our community.Located at 500 Brookfield Drive, Winchester, VA 22601, Brookfield Corporate Apartments offers spacious, fully furnished one and two-bedroom apartments. Each apartment is designed with your comfort in mind and comes equipped with linens, kitchenware, two TVs with

  548 Brookfield Dr, Winchester, VA 22601
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  $430,000 Sold Nov 21, 2025

  • 1,313 Sq Ft
  • $327/SF
  • 55 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  116 Route 1288, Winchester, VA 22602

  BRAND NEW HOME. FULLY FINISHED. No HOA. Discover the charm of this stunning new construction home in the desirable Asbury Terrace community.. This exquisite Colonial-style residence boasts a thoughtful layout with 3 spacious bedrooms and 2.5 luxurious bathrooms, including a master suite featuring a relaxing soaking tub and walk-in closet. The heart of the home is the modern kitchen, perfect for

  Elcy Pereira Elcy & Co. Realty, LLC.

  116 Route 1288, Winchester, VA 22602
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  /37

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,052 Sq Ft

  216 E Piccadilly St, Winchester, VA 22601

  216 E Piccadilly St, Winchester, VA 22601
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  /13

  $200,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,430 Sq Ft

  163 Cabin Ln, Winchester, VA 22603

  Discover the potential in this 3 bedroom, 2 bath home on 6.10 unrestricted acres, the perfect opportunity for buyers looking to create their own country retreat. The home is in need of significant work and is being sold AS IS. Outside, you’ll find a detached garage with an apartment above, ideal for guests, rental income, or multi-generational living. Multiple sheds provide ample storage for

  

  Kerry Wysong

  Long & Foster Real Estate, Inc.

  (540) 709-8545

  163 Cabin Ln, Winchester, VA 22603
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  /13

  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 1,823 Sq Ft
  • House for Rent

  1701 Brandon Dr, Winchester, VA 22601

  Great home in fantastic location., Walking distance to Handley. Nice fenced rear yard, great deck. Laundry on first level. Quartz counter top. Two Fireplaces not operational. Large finished room in basement. LOT of storage and shelving in unfinished portion of basement. Great building under deck for mowers and outside storage. Extremely convenient quiet street. Pets on case by case basis. All

  Jeff Webber Long & Foster Real Estate, Inc.

  1701 Brandon Dr, Winchester, VA 22601
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  $250,000 Sold Nov 21, 2025

  • 864 Sq Ft
  • $289/SF
  • 3 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1998

  310 Wardensville Grade, Winchester, VA 22602

  10/2 seller has received multiple offers*****no more showings....Nestled in a serene rural setting, this charming ranch-style home offers a perfect blend of comfort and tranquility. Built in 1998, this well-maintained residence features a traditional floor plan that invites you to unwind and enjoy life. With two cozy bedrooms and a full bathroom equipped with a tub shower, this home is designed

  Tracy Link Coldwell Banker Premier

  310 Wardensville Grade, Winchester, VA 22602
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  /21

  Est $316,201 Not Listed For Sale

  • Studio
  • 539 Sq Ft

  3464 Papermill Rd, Winchester, VA 22602

  3464 Papermill Rd, Winchester, VA 22602
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  /6

  $55,000 Pending

  • Land
  • 5.23 Acres
  • $10,516 per Acre

  0 0 Shockeysville Rd, Winchester, VA 22603

  Embrace the serenity of nature on this 5.23-acre wooded lot, offering the perfect blend of privacy, beauty, and possibility. Tucked away in a peaceful setting, this property features a picturesque pond, creating an ideal backdrop for your future home, weekend getaway, or recreational escape. Whether you're dreaming of building a custom home, setting up a private retreat, or simply investing in

  

  Kerry Wysong

  Long & Foster Real Estate, Inc.

  (540) 329-2751

  0 0 Shockeysville Rd, Winchester, VA 22603
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  /33

  $1,750 - $1,850 per month

  Madison Village Apartments (Winchester)

  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

  110 Bulmer Loop, Winchester, VA 22602
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  /53

  $349,000 Sold Nov 21, 2025

  • 1,416 Sq Ft
  • $246/SF
  • 6 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1963

  96 Molden Dr, Winchester, VA 22601

  Introducing this thoughtfully-updated 3-bedroom, 1-full bath brick rancher offering true turnkey living in a highly desirable location! Featuring modern upgrades and a partially finished basement, this home provides comfort and style. The centralized location is incredibly convenient, situated just steps from Daniel Morgan Middle School and only minutes from all the shopping, dining, parks, and

  Dan Whitacre Colony Realty

  96 Molden Dr, Winchester, VA 22601
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  /2

  Est $233,738 Not Listed For Sale

  • Studio

  128 Rappahannock Trail, Winchester, VA 22602

  128 Rappahannock Trail, Winchester, VA 22602
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  /2

  $365,000 Coming Soon

  • 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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  /8

  $1,595 per month

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Townhouse for Rent

  202 E Whitlock Ave, Winchester, VA 22601

  Experience the charm of this beautifully renovated end-of-row townhouse in the heart of the City of Winchester, available for lease starting November 19, 2025. This residence, originally built in 1956, will undergo a major renovation, ensuring modern luxury meets classic elegance. With three spacious bedrooms and a full bath, this home is designed for comfort and style. The partially finished

  Brandon Pifer Pifer Realty, LLC

  202 E Whitlock Ave, Winchester, VA 22601
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  /38

  $299,000 Sold Nov 21, 2025

  • 1,947 Sq Ft
  • $154/SF
  • 6 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1978

  266 Pond View Ln, Winchester, VA 22603

  Discover peace and privacy at 266 Pond View Lane. Nestled on 5 scenic acres, this property offers the perfect retreat from the hustle and bustle— A wrap-around gravel driveway welcomes you home, providing plenty of space for parking and easy access to the attached garage! Step inside to find 3 spacious bedrooms, 1 full bathroom, formal dining & 3 spacious living areas! The kitchen offers plenty

  Lisa Behr Coldwell Banker Premier

  266 Pond View Ln, Winchester, VA 22603
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  /3

  Not Listed For Sale

  2902 Valley Ave, Winchester, VA 22601

  2902 Valley Ave, Winchester, VA 22601
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  /58

  $445,000 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 2,176 Sq Ft

  125 Alliance Ct, Winchester, VA 22602

  Welcome to this beautifully maintained home located in the highly sought-after Freedom Manor community in Winchester, VA! Ideally situated just minutes from shopping, dining, and everyday conveniences—with quick access to I-81—this home offers the perfect combination of comfort, functionality, and location.Inside, the main level features stylish and durable luxury vinyl plank (LVP)

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  (540) 730-2810

  125 Alliance Ct, Winchester, VA 22602
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  /2

  $1,600 - $1,800 per month

  Apartment for Rent

  1 - 2 Beds

  148 N Loudoun St, Winchester, VA 22601

  Beautiful 1 and 2 bedroom fully furnished apartments. Located directly on the old town walking mall. Washer dryer included in the unit. On site parking.

  148 N Loudoun St, Winchester, VA 22601
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  /55

  $580,000 Sold Nov 21, 2025

  • 3,516 Sq Ft
  • $165/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1995

  1039 Hiatt Rd, Winchester, VA 22603

  If you’re seeking space, convenience, and a tranquil setting in the Whitacre Farm section of Winchester then this property delivers! Set on nearly 6 private acres, this 3-bedroom, 2-bath home offers peaceful wooded surroundings and incredible views from the top of the lot. Inside, you will find ALL rooms are generously sized with plenty of natural light creating a warm, comfortable layout. The

  Janet Flaherty Keller Williams Realty

  1039 Hiatt Rd, Winchester, VA 22603
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  /34

  Est $383,591 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,460 Sq Ft

  310 Mountain Falls Blvd, Winchester, VA 22602

  310 Mountain Falls Blvd, Winchester, VA 22602
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  /24

  $299,900 Under Contract

  • 2 Beds
  • 1 Bath
  • 858 Sq Ft

  525 E Cork St, Winchester, VA 22601

  Beautiful and affordable Gem in the middle of Winchester City.Private, fully fenced yard with extra parking and storage. Updated A/C and two year old roof.

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 900-1951

  525 E Cork St, Winchester, VA 22601
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  /18

  $1,900 per month

  • 3 Beds
  • 2 Baths
  • 1,687 Sq Ft
  • Townhouse for Rent

  1984 Cidermill Ln, Winchester, VA 22601

  This exceptionally maintained 3-bedroom, 2-bath semi-attached home offers both comfort and convenience. Ideally located in the Orchard Hill neighborhood, off Jubal Early Drive, offering easy commuter access, minutes to Downtown Winchester, grocery, retail and restaurants.This home is welcoming, filled with natural light with a flowing floor plan. The first floor features lovely hardwood

  Rachael Duvall TTR Sotheby's International Realty

  1984 Cidermill Ln, Winchester, VA 22601
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  $905,264 Sold Nov 20, 2025

  • 3,675 Sq Ft
  • $246/SF
  • 103 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2025

  219 Taggart Dr, Winchester, VA 22602

  Main Level Living in Raven Pointe on one of 9 lots left! The ever-popular Tracey model with a side load 3-car garage. Home features a flexible floorpan that allows for maximum customization. Home features include large, open kitchen, vaulted ceilings in the living room (12'+), an adjacent sunroom, covered porch with Trex decking, tile showers in all baths and much more. This is a customizable

  JP Carr Merrifield Realty, LLC

  219 Taggart Dr, Winchester, VA 22602
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  /38

  Est $347,032 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,380 Sq Ft

  1172 Purcell Ln, Winchester, VA 22603

  1172 Purcell Ln, Winchester, VA 22603
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  /50

  $425,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  220 Chestnut Grove Rd, Winchester, VA 22603

  Experience the best of country living with this charming 2-Bedroom, 1-Bath Rancher nestled on 15 unrestricted acres in beautiful Frederick County, VA. Perfect as a full-time residence, weekend retreat, or potential farm, this property offers the peace and privacy of rural life while still being within easy reach of town conveniences.Step inside to find a cozy and move-in ready Home featuring

  

  Laura King

  MarketPlace REALTY

  (540) 351-9580

  220 Chestnut Grove Rd, Winchester, VA 22603
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  /25

  $1,605 - $1,800 per month

  HARRISON PLAZA RESIDENTIAL

  1 - 2 Beds

  2310 Valor Dr, Winchester, VA 22601

  Harrison Plaza is a new mixed-use development located at the intersection of Hope Drive and Valor Drive in the heart of Winchester, VA. This three-building community offers 70 one- and two-bedroom spacious modern apartments minutes away from local shopping centers, restaurants, and entertainment venues.Interior features include an open floor plan with stylish cabinets, granite countertops,

  2310 Valor Dr, Winchester, VA 22601
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  $515,000 Sold Nov 20, 2025

  • 2,529 Sq Ft
  • $204/SF
  • 17 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2001

  223 Cavalry Dr, Winchester, VA 22602

  Nestled in a prestigious eastside enclave, this exquisite residence offers an unparalleled blend of sophistication and convenience, mere minutes from Winchester’s vibrant core—perfect for discerning commuters. A meticulously landscaped exterior ushers you into a breathtaking open-concept interior, where timeless elegance meets modern comfort. ***MAIN LEVEL: The heart of the home is a soaring

  Timothy Shamblin Coldwell Banker Premier

  223 Cavalry Dr, Winchester, VA 22602
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  Est $498,702 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,479 Sq Ft

  1960 Siler Rd, Winchester, VA 22603

  1960 Siler Rd, Winchester, VA 22603

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