12,853

Winchester County, VA Homes

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  • /61

    $424,000

    $35K PRICE DROP Pending
    • 6 Beds
    • 3 Baths
    • 1,552 Sq Ft

    2250 Roosevelt Blvd, Winchester, VA 22601

    Charming Cape Cod nestled in a quiet residential neighborhood, just minutes from Route 11 and I-81 for easy commuting. This light-filled home welcomes you with a bright living room featuring a stunning stone fireplace as its centerpiece. The cabinet-packed kitchen is the heart of the home and offers granite countertops and a bar-height peninsula that opens seamlessly to the living room . The main

    Heloisa Amar Samson Properties

    2250 Roosevelt Blvd, Winchester, VA 22601
  • /26

    $2,250 Per Month

    • 3 Beds
    • 2 Baths
    • 1,725 Sq Ft
    • House for Rent

    2141 Valley Ave, Winchester, VA 22601

    Renovated cape cod on Valley Avenue with 3 bedrooms and 2 full baths (tiled showers), open kitchen living concept, fresh new paint, Luxury Vinyl Plank flooring throughout, HVAC, and large parking area with side yard. Brand new Quartz countertops, cabinets, and appliances. Rentspree application required and pets case by case but no more than two animals will be accepted. Owner/Agent

    Dave Spence RE/MAX Roots

    2141 Valley Ave, Winchester, VA 22601
  • /2

    $565,000

    Sold Sep 16, 2025

    183 Omps Dr, Winchester, VA 22601

    • 4 Beds
    • 2.5 Baths
    • 2,617 Sq Ft
    • Built 1985

    Last Sold Summary

    • $216/SF

    Current Estimated Value $599,382

    Last Listing Agent Stuart Wolk ERA Oakcrest Realty, Inc.

    183 Omps Dr, Winchester, VA 22601
    • /39

      Est $611,558

      Not Listed For Sale

      2938 S Pleasant Valley Rd, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,376 Sq Ft
      • Built 1960
      2938 S Pleasant Valley Rd, Winchester, VA 22601

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Danielle Snapp Coldwell Banker Premier

  • /54

    $725,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,453 Sq Ft

    622 Tennyson Ave, Winchester, VA 22601

    Available now in One of Winchester's Most Sought-After Locations. Opportunities like this don't come along often. Nestled on one of the most desirable streets in Winchester, just behind John Handley High School, this charming Cape Cod offers the perfect blend of character, comfort, and location. Lovingly maintained and full of curb appeal, this delightful four-bedroom, two-and-a-half-bath home

    Janet Flaherty Keller Williams Realty

    622 Tennyson Ave, Winchester, VA 22601
  • /12

    $2,100 Per Month

    • 3 Beds
    • 1 Bath
    • 2,781 Sq Ft
    • Condo for Rent

    107 Morgan St, Winchester, VA 22601

    3 bedroom 1 bath apartment on the 2nd and 3rd floors. Spacious with lots of light. Great location. No pets.Tenant is responsible for all utilities.This unit includes the detached 1 car garage and use of the driveway. In addition on street parking is available.

    Kenny Ritenour Samson Properties

    107 Morgan St, Winchester, VA 22601
  • /43

    $398,000

    Sold Mar 26, 2026

    216 W Cedarmeade Ave, Winchester, VA 22601

    • 3 Beds
    • 2 Baths
    • 1,823 Sq Ft
    • Built 1967

    Last Sold Summary

    • $218/SF
    • 1 Day On Market

    Current Estimated Value $407,476

    Last Listing Agent Sheila Pack RE/MAX Roots

    216 W Cedarmeade Ave, Winchester, VA 22601
    • /25

      Est $347,049

      Not Listed For Sale

      2817 Papermill Rd, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,248 Sq Ft
      • Built 1989
      2817 Papermill Rd, Winchester, VA 22601

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Anna Fox NextHome Realty Select

  • /23

    $419,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,094 Sq Ft

    126 Swansong Place, Winchester, VA 22603

    Exceptional value for a 4‐bedroom END‐UNIT townhome is ready for move‐in! Brand‐new construction offers modern style and comfort with oak stairs with upgraded railings and durable LVP flooring throughout the main level. Backing to open space in the newest section of Snowden Bridge, this spacious home includes a flexible entry‐level bedroom with full bath, a bright open‐concept main living area,

    Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

    126 Swansong Place, Winchester, VA 22603
  • /18

    $2,199 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,504 Sq Ft
    • Townhouse for Rent

    413 Tevis St, Winchester, VA 22601

    NEWER UNIT HAS AN OPEN KITCHEN WITH GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, LED LIGHTING AND 1 USB/OUTLET COMBO IN KITCHEN. WHOLE HOUSE WINDOW TREATMENTS INCLUDED, WASHER/DRYER AND PROGRAMABLE THERMOSTAT. RENT INCLUDES EXTERIOR LAWN CARE AND SNOW REMOVAL. WASHER AND DRYER INCLUDED. VERY NEAR TO 1-81 AND ALL SHOPPING

    Rajesh Cheruku FAB Realty LLC

    413 Tevis St, Winchester, VA 22601
  • /28

    $350,000

    Sold Jul 06, 2026

    113 Christopher Dr, Winchester, VA 22601

    • 3 Beds
    • 1.5 Baths
    • 1,890 Sq Ft
    • Built 1966

    Last Sold Summary

    • $185/SF
    • 59 Days On Market

    Current Estimated Value $349,318

    Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.

    113 Christopher Dr, Winchester, VA 22601
    • /19

      Est $339,413

      Not Listed For Sale

      2918 S Pleasant Valley Rd, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,199 Sq Ft
      • Built 1981
      2918 S Pleasant Valley Rd, Winchester, VA 22601

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Anna Fox NextHome Realty Select

  • /30

    $379,900

    • 2 Beds
    • 1.5 Baths
    • 1,186 Sq Ft

    711 E Cork St, Winchester, VA 22601

    This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

    Marco Novillo Spring Hill Real Estate, LLC.

    711 E Cork St, Winchester, VA 22601
  • /25

    $2,400 Per Month

    • 4 Beds
    • 3.5 Baths
    • Townhouse for Rent

    241 Monteith Dr, Winchester, VA 22601

    Welcome to this stunning new construction 3-level townhome offering 4 bedrooms, 3.5 baths, and a 1-car garage with extra storage space, perfectly situated on a premium homesite backing to mature trees for added privacy and peaceful views. The entry level features a versatile fourth bedroom with a private full bath and walk-in shower, making it ideal as a guest suite, home office, or recreation

    Denise Finley Pearson Smith Realty, LLC

    241 Monteith Dr, Winchester, VA 22601
  • /74

    $794,000

    Sold Aug 27, 2025

    1001 Armistead St, Winchester, VA 22601

    • 5 Beds
    • 4 Baths
    • 4,295 Sq Ft
    • Built 2005

    Last Sold Summary

    • $185/SF
    • 4 Days On Market

    Current Estimated Value $817,824

    Last Listing Agent Sheila Pack RE/MAX Roots

    1001 Armistead St, Winchester, VA 22601
    • /21

      Est $366,365

      Not Listed For Sale

      2915 S Pleasant Valley Rd, Winchester, VA 22601

      • 3 Beds
      • 2 Baths
      • 1,388 Sq Ft
      • Built 1990
      2915 S Pleasant Valley Rd, Winchester, VA 22601

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Anna Fox NextHome Realty Select

  • /22

    $599,950

    $25K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,948 Sq Ft

    446 N Loudoun St, Winchester, VA 22601

    Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking

    Lawrence Lessin Homes By Owner, Inc.

    446 N Loudoun St, Winchester, VA 22601
  • /2

    $1,595 Per Month

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Townhouse for Rent

    346 Gray Ave, Winchester, VA 22601

    This charming Colonial townhouse, built in 1930 and set for a major renovation in 2026, offers a unique blend of historic character and modern comfort. With three spacious bedrooms and a full bathroom, this home is perfect for those seeking a cozy retreat. The inviting hardwood and luxury vinyl plank flooring throughout enhances the warmth of the space. Located in a vibrant neighborhood, you'll

    Brandon Pifer Pifer Realty, LLC

    346 Gray Ave, Winchester, VA 22601
  • /39

    $270,000

    Sold Jan 21, 2026

    423 Highland Ave, Winchester, VA 22601

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 1930

    Last Sold Summary

    • $208/SF
    • 44 Days On Market

    Current Estimated Value $278,701

    Last Listing Agent Carlos Soares Samson Properties

    423 Highland Ave, Winchester, VA 22601
    • /38

      Est $275,033

      Not Listed For Sale

      2945 Sorrell Ct, Winchester, VA 22601

      • 2 Beds
      • 1.5 Baths
      • 1,332 Sq Ft
      • Built 2000
      2945 Sorrell Ct, Winchester, VA 22601

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Carolyn Waymack Crum Realty, Inc.

  • /42

    $569,000

    $10K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,108 Sq Ft

    2532 Middle Rd, Winchester, VA 22601

    Welcome to this stunning, custom-built Craftsman-style home that perfectly balances contemporary elegance with everyday functionality. Located in a prime, highly convenient Winchester location, this property immediately captivates with its striking curb appeal, highlighted by a large covered front porch and a classic architectural silhouette. Step inside to discover an immaculate interior bathed

    Dan Whitacre Colony Realty

    2532 Middle Rd, Winchester, VA 22601
  • /8

    $1,595 Per Month

    • 3 Beds
    • 1 Bath
    • 900 Sq Ft
    • Townhouse for Rent

    0 S Cameron St, Winchester, VA 22601

    This charming Colonial townhouse, built in 1930 and set for a major renovation in 2024, offers a unique blend of historic character and modern comfort. With three spacious bedrooms and a full bathroom, this home is perfect for those seeking a cozy retreat. The end-of-row design provides added privacy and natural light, enhancing the inviting atmosphere. Located in a vibrant neighborhood, you'll

    Brandon Pifer Pifer Realty, LLC

    0 S Cameron St, Winchester, VA 22601
  • /34

    $450,000

    Sold Oct 17, 2025

    711 S Braddock St, Winchester, VA 22601

    • 3 Beds
    • 3.5 Baths
    • 2,052 Sq Ft
    • Built 2016

    Last Sold Summary

    • $219/SF
    • 7 Days On Market

    Current Estimated Value $491,083

    Last Listing Agent Dave Spence RE/MAX Roots

    711 S Braddock St, Winchester, VA 22601
    • /18

      Est $281,088

      Not Listed For Sale

      2947 Sorrell Ct, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,332 Sq Ft
      • Built 2001
      2947 Sorrell Ct, Winchester, VA 22601

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Laura White ERA Oakcrest Realty, Inc.

  • /50

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft

    1004 Pennsylvania Ave, Winchester, VA 22601

    Charming, Updated Rancher in the Heart of Winchester! Welcome home to this impeccably maintained 3-bedroom, 2-bath ranch offering the perfect blend of comfort, character, and convenience—all on one level! From the moment you arrive, you'll appreciate the pride of ownership and thoughtful updates throughout. The spacious kitchen is the heart of the home, offering abundant cabinetry and room to

    Traci Shoberg Samson Properties

    1004 Pennsylvania Ave, Winchester, VA 22601
  • /14

    $1,499 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,047 Sq Ft
    • Townhouse for Rent

    1111 Franklin St, Winchester, VA 22601

    2 levels TOWNHOUSE, 2 bathrooms and 2 bedroom with large walking closet, large living room and Eat in kitchen with laundry hook up, located near I-81,Rt-7 leesburg access, Rt 50 and medical college, hospital, Amazon & many auto warehouses, TREK & many other industrial companies, also 35 minutes to one hour drive for many NOVA SUBURB like Leesburg, Dulles airport, DC Metro, Tyson’s corner and

    Ram Beladia First American Real Estate

    1111 Franklin St, Winchester, VA 22601
  • /105

    $1,149,000

    Sold Feb 20, 2026

    819 Armistead St, Winchester, VA 22601

    • 5 Beds
    • 3.5 Baths
    • 5,262 Sq Ft
    • Built 1989

    Last Sold Summary

    • 4% Below List Price
    • $218/SF
    • 1 Day On Market

    Current Estimated Value $1,198,503

    Last Listing Agent Natalie Langford ERA Oakcrest Realty, Inc.

    819 Armistead St, Winchester, VA 22601
    • /16

      Est $297,693

      Not Listed For Sale

      2975 Sorrell Ct, Winchester, VA 22601

      • 2 Beds
      • 2.5 Baths
      • 1,880 Sq Ft
      • Built 1990
      2975 Sorrell Ct, Winchester, VA 22601

      Last Sold Summary

      Last Listing Agent Sarah Reynolds Keller Williams Realty

  • /46

    $310,000

    $10K PRICE DROP Pending
    • 3 Beds
    • 1 Bath
    • 1,250 Sq Ft

    2917 First St, Winchester, VA 22601

    Welcome home to this charming stone rancher, perfectly situated on a fantastic lot adorned with gorgeous, mature trees and a lush, expansive yard. Step inside to find a spacious living room bathed in natural light, featuring rich hardwood flooring and a cozy stone fireplace that serves as the room's centerpiece. The effortless layout flows seamlessly into the kitchen and formal dining room,

    Dan Whitacre Colony Realty

    2917 First St, Winchester, VA 22601
  • /11

    $1,149 Per Month

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

    1704 Roberts St Unit 6, Winchester, VA 22601

    RECENTLY RENOVATED, ALL-BRICK BUILDING THAT WAS COMPLETELY REDONE OVER LAST SEVERAL YEARS * UNIT HAS NEWER STAINLESS-STEEL APPLIANCES AND NEWER VINYL-PLANK FLOORING * EXTERIOR OF BUILDING WAS PAINTED IN 2018. NEW WINDOWS, NEW GUTTERS AND NEW ROOF ADDED IN 2018. ALL NEW ELECTRIC SERVICE IN 2018, ALSO * AWESOME KITCHEN W/NEWER CABINETS & GRANITE C'TOPS * REDONE BATH W/CERAMIC TILE FLOORS & TUB

    John Gregory Holmes Samson Properties

    1704 Roberts St Unit 6, Winchester, VA 22601
  • /44

    $782,000

    Sold Oct 03, 2025

    939 Buckner Dr, Winchester, VA 22601

    • 5 Beds
    • 4.5 Baths
    • 6,122 Sq Ft
    • Built 2000

    Last Sold Summary

    • $128/SF
    • 46 Days On Market

    Current Estimated Value $883,986

    Last Listing Agent Kiran K. Morzaria Parekh Samson Properties

    939 Buckner Dr, Winchester, VA 22601
    • /23

      Est $294,734

      Not Listed For Sale

      2950 Sorrell Ct, Winchester, VA 22601

      • 3 Beds
      • 3.5 Baths
      • 1,280 Sq Ft
      • Built 1990
      2950 Sorrell Ct, Winchester, VA 22601

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Maria Jaimes Millennium Realty Group Inc.

  • /25

    $260,000

    $60K PRICE DROP Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,222 Sq Ft

    317 Fairview Ave, Winchester, VA 22601

    Price improvement - Motivated sellers - bring offers! Fully Renovated SFH in Historic Winchester! Prime location. Just minutes from charming Historic Downtown Winchester featuring local shops, restaurants, entertainment, and more! Beautifully Updated throughout. This charming home offers bright, inviting living spaces with modern finishes and thoughtfully updates designed for comfortable everyday

    Donna Lutkins Real Broker, LLC

    317 Fairview Ave, Winchester, VA 22601
  • /32

    $1,995 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,558 Sq Ft
    • House for Rent

    916 S Loudoun St, Winchester, VA 22601

    3 bedroom and 2 1/2 bath 2 story house. Kitchen featuring a large island and pantry. LVP flooring throughout the home. There is a separate laundry room with washer and dryer. The primary bedroom has a large walk-in closet with an additional closet for more storage as well as dual vanities in the bathroom, featuring a standing shower. Heat pump with central air conditioning. Storage shed. Driveway

    Barbara Gaul Jim Barb Realty, Inc.

    916 S Loudoun St, Winchester, VA 22601
  • /42

    $464,000

    Sold Apr 13, 2026

    407 Jefferson St, Winchester, VA 22601

    • 3 Beds
    • 3 Baths
    • 2,805 Sq Ft
    • Built 1950

    Last Sold Summary

    • 3% Below List Price
    • $165/SF
    • 64 Days On Market

    Current Estimated Value $464,418

    Last Listing Agent Gillian Greenfield Coldwell Banker Premier

    407 Jefferson St, Winchester, VA 22601
    • /47

      Est $470,371

      Not Listed For Sale

      2894 Packer St, Winchester, VA 22601

      • 4 Beds
      • 2.5 Baths
      • 2,460 Sq Ft
      • Built 2006
      2894 Packer St, Winchester, VA 22601

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Renzo Falla RE/MAX Real Estate Connections

  • /2

    $325,000

    $40K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,678 Sq Ft

    719 National Ave, Winchester, VA 22601

    Priced to sell! A true Federal‐style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it features high ceilings, original hardwood floors, solid wood doors and trim, and a beautiful covered front porch—timeless details that showcase the home’s enduring character. Designed with good bones and a layout that adapts to many

    Windy Harris Hunt Country Sotheby's International Realty

    719 National Ave, Winchester, VA 22601
  • /20

    $1,295 Per Month

    • 1 Bed
    • 1 Bath
    • 3,267 Sq Ft
    • Condo for Rent

    515 N Loudoun St Unit 3, Winchester, VA 22601

    LANDLORD PAYS UTILITIES - INCLUDING HEAT! Affordable old-fashioned charmer near downtown Winchester. Cozy 1-bedroom apartment in a quaint 4-unit building. Hardwood floors. Living room. Galley kitchen. Landlord pays heat, electricity, water and sewer, and city trash pick-up. Parking in rear. Minimum 1-year lease. Longer lease preferred. Renter's insurance required. No smoking or vaping. Pets

    Teresa Strohmeyer ERA Oakcrest Realty, Inc.

    515 N Loudoun St Unit 3, Winchester, VA 22601
  • /52

    $347,500

    Sold Apr 09, 2026

    217 Myrtle Ave, Winchester, VA 22601

    • 3 Beds
    • 1 Bath
    • 907 Sq Ft
    • Built 1961

    Last Sold Summary

    • 7% Below List Price
    • $383/SF
    • 50 Days On Market

    Current Estimated Value $343,178

    Last Listing Agent Pamela Foltz Realty ONE Group Old Towne

    217 Myrtle Ave, Winchester, VA 22601
    • /46

      Est $470,290

      Not Listed For Sale

      201 Russelcroft Rd, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 3,066 Sq Ft
      • Built 1970
      201 Russelcroft Rd, Winchester, VA 22601

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Dorothy Vance The KW Collective

Showing Results 321 - 360, Page 9 of 18

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