37,023

Winchester, VA Homes

Section Image Section Image
  • /29

    $369,999

    • 3 Beds
    • 2 Baths
    • 1,387 Sq Ft

    2919 S Pleasant Valley Rd, Winchester, VA 22601

    Home Warranty for the Buyer + Bonus for the Buyer’s Agent with a Ratified Contract in September! Welcome to this adorable and beautifully refreshed Cape Cod, ideally located on a quiet street in Winchester City with no HOA! This move-in-ready home offers a comfortable and versatile floor plan, featuring a primary suite on the main level, plus two spacious bedrooms and a second full bathroom

    Patricia Rivas Plata Keller Williams Realty Dulles

    2919 S Pleasant Valley Rd, Winchester, VA 22601
  • /2

    $1,425 Per Month

    • 2 Beds
    • 1 Bath
    • 1,036 Sq Ft
    • House for Rent

    131 S Purcell Ave, Winchester, VA 22601

    This charming Colonial-style home, built in 1920, offers 2 spacious bedrooms and 1 full bathroom, this detached residence is perfect for those seeking a cozy yet functional living space. The property features durable vinyl siding, ensuring low maintenance while maintaining its classic appeal. On-street parking available. Conveniently located near a variety of local amenities. Residents can enjoy

    Rebecca Sims Century 21 Redwood Realty

    131 S Purcell Ave, Winchester, VA 22601
  • /63

    $365,000

    Sold Apr 20, 2026

    508 Grouse Dr, Winchester, VA 22602

    • 3 Beds
    • 2.5 Baths
    • 2,520 Sq Ft
    • Built 2025

    Last Sold Summary

    • $145/SF
    • 104 Days On Market

    Last Listing Agent Steve DuBrueler Coldwell Banker Premier

    508 Grouse Dr, Winchester, VA 22602
    • /37

      Not Listed For Sale

      111 Nootka Way, Winchester, VA 22602

      • 3 Beds
      • 2.5 Baths
      • 1,509 Sq Ft
      • Built 2025
      111 Nootka Way, Winchester, VA 22602

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Brooks Sears Pearson Smith Realty, LLC

  • /70

    $659,900

    • 4 Beds
    • 4.5 Baths
    • 4,271 Sq Ft

    291 Huntersridge Rd, Winchester, VA 22602

    Space, style, and room to live your best life come together in this 4-bedroom, 4.5-bath, 3-level Colonial in desirable Oakdale Crossing. With flexible spaces, great indoor-outdoor living, and a location close to everything Winchester has to offer, this home is ready for whatever comes next.The main level features an open, inviting flow between the kitchen, breakfast room, and family room,

    Laura White ERA Oakcrest Realty, Inc.

    291 Huntersridge Rd, Winchester, VA 22602
  • /17

    $2,400

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    2066 Honeysuckle Ln, Winchester, VA 22601

    Immaculate home now available for rent in sought after ORCHARD HILL SUBDIVISION! 3 spacious bedrooms, ample storage space with several walk in closets, all appliances convey including washer/dryer. Sun room with cathedral ceilings and atrium doors to exit onto the rear brick patio, storage shed, small garden, and so much more! VAR or NVAR rental application with $50 per person application fee

    2066 Honeysuckle Ln, Winchester, VA 22601
  • /58

    $929,200

    Sold Mar 27, 2026

    240 Glendobbin Rd, Winchester, VA 22603

    • 6 Beds
    • 3.5 Baths
    • 3,848 Sq Ft
    • Built 2004

    Last Sold Summary

    • 7% Below List Price
    • $241/SF
    • 8 Days On Market

    Current Estimated Value $953,354

    Last Listing Agent Lori Bales Keller Williams Realty

    240 Glendobbin Rd, Winchester, VA 22603
    • /8

      Not Listed For Sale

      151 Tomahawk Trail, Winchester, VA 22602

      151 Tomahawk Trail, Winchester, VA 22602

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Gina Griffith MarketPlace REALTY

  • /7

    $4,000,000

    Under Contract
    • Land
    • 27.2 Acres
    • $147,059 per Acre

    0 N Frederick Pike Unit VAWI2007698, Winchester, VA 22603

    Unprecedented Development Opportunity, County of Frederick, 27.2 acres in land use plan for high density rezoning (RP) and development (currently zoned RA, will require rezoning). Ideal townhouse and apartment project. Gateway to downtown Old Town Winchester. Public utilities to site. Truly a catalyst development opportunity, located in the fast growing metropolitan area in Virginia. Voted #1

    Gillian Greenfield Coldwell Banker Premier

    0 N Frederick Pike Unit VAWI2007698, Winchester, VA 22603
  • /26

    $1,499 Per Month

    • 2 Beds
    • 1.5 Baths
    • 998 Sq Ft
    • Townhouse for Rent

    1016 Franklin St Unit 5, Winchester, VA 22601

    Beautiful 2 level END Unit Townhome, Cement concrete Long Driveway, Reasonable Rental price , Completely Renovated, close to I-81 exit 315 Rt.7 , walking distance to shopping center and downtown 1 mile, Near Exit 215 of I-81, Rt-7, community is near major highway, Beautiful downtown and blossom mall, school bus stop front of the house and long driveway with private parking and management takes

    Ram Beladia First American Real Estate

    1016 Franklin St Unit 5, Winchester, VA 22601
  • /66

    $360,000

    Sold Apr 10, 2026

    113 Worsham Terrace, Winchester, VA 22602

    • 3 Beds
    • 4 Baths
    • 1,760 Sq Ft
    • Built 2011

    Last Sold Summary

    • $205/SF
    • 3 Days On Market

    Current Estimated Value $361,609

    Last Listing Agent Nicole Lewis Coldwell Banker Premier

    113 Worsham Terrace, Winchester, VA 22602
    • /13

      Not Listed For Sale

      LOT B 4661 Middle Rd, Winchester, VA 22602

      LOT B 4661 Middle Rd, Winchester, VA 22602

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Maureen Cunningham Century 21 Redwood Realty

  • /22

    $269,000

    • Land
    • 42,253 Sq Ft
    • $277,320 per Acre

    823 Armistead St, Winchester, VA 22601

    *** Price shown is for lot only. Seller is willing to assist Buyer in building this beautiful home plandesigned by Seller customized for this lot and optimized for cost effective construction. Closingon the lot may occur upon issuance of the Building Permit in Buyer’s name by the City ofWinchester. ***This modern farmhouse style home includes 5,630 square feet of living space

    Janet Flaherty Keller Williams Realty

    823 Armistead St, Winchester, VA 22601
  • /2

    $1,495

    Total Monthly Price

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

    307 Emily Ln, Winchester, VA 22602

    ** Photos Coming Soon** Charming 1 level 2 bed 1 bath situated in Frederick County Virginia. This apartment has LVP flooring throughout, washer/dryer, dishwasher and above the range microwave. Enjoy morning walks through the great neighborhood and take the pets or children to play at the great little playground. Enjoy the evenings sitting on the back deck surrounded by nature! This is a

    307 Emily Ln, Winchester, VA 22602
  • /25

    $281,000

    Sold Dec 19, 2025

    230 Shenandoah Trail, Winchester, VA 22602

    • 2 Beds
    • 2 Baths
    • 1,393 Sq Ft
    • Built 1975

    Last Sold Summary

    • $202/SF
    • 76 Days On Market

    Current Estimated Value $290,726

    Last Listing Agent Wayne Wilson Thomas and Talbot Estate Properties, Inc.

    230 Shenandoah Trail, Winchester, VA 22602
    • /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.

  • /48

    $389,999

    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft

    709 Dicks Hollow Rd, Winchester, VA 22603

    Exceptional value meets impeccable quality! From the bright, welcoming entryway to the beautifully crafted living spaces, every detail of this home speaks to superior craftsmanship. Perfect for discerning buyers seeking a flawless blend of style and convenience, this property presents a rare window of opportunity. Schedule your showing today and secure this incredible home before it’s gone!

    Fehiber Rosario NBI Realty, LLC

    709 Dicks Hollow Rd, Winchester, VA 22603
  • /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 &

    John Gregory Holmes Samson Properties

    1704 Roberts St Unit 6, Winchester, VA 22601
  • /29

    $374,990

    Sold Jun 02, 2026

    221 Monteith Dr, Winchester, VA 22601

    • 3 Beds
    • 3.5 Baths
    • 1,784 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 9% Below List Price
    • $210/SF
    • 87 Days On Market

    DRB Homes Village at Valor Crossing - Townhomes

    221 Monteith Dr, Winchester, VA 22601
    • /38

      Not Listed For Sale

      116 Webster Ct, Winchester, VA 22603

      • 2 Beds
      • 2 Baths
      • 1,564 Sq Ft
      116 Webster Ct, Winchester, VA 22603

      Last Sold Summary

  • /22

    $384,990

    New Construction $10K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 1,893 Sq Ft

    111 Heirloom Way, Winchester, VA 22603

    Move‐in ready and designed for the life you want to live.Enjoy effortless main‐level living in Hiatt Pointe at Snowden Bridge, a gated 55+ active adult community where comfort meets connection. This low‐maintenance villa offers a serene primary suite and laundry on the entry level, a screened rear porch for relaxing mornings and evenings, and a one‐car garage for everyday

    Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

    111 Heirloom Way, Winchester, VA 22603
  • /13

    $2,495

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,615 Sq Ft
    • House for Rent

    143 S Purcell Ave, Winchester, VA 22601

    Beautiful, fully renovated, 4 bedroom 2 full bath home on a quiet street. This home has a brand new kitchen and 2 new bathrooms, large bedroom on the main level and 3 bedrooms on upper level, all new appliances, water heater, electric update, new HVAC system. Across the street is Daniel Morgan school, Jim Barnett park, a short walk to downtown Winchester, easy access to Rt 7E, 50 E and I81. With

    143 S Purcell Ave, Winchester, VA 22601
  • /2

    $325,000

    Sold Mar 12, 2026

    114 Harrison Ln, Winchester, VA 22602

    • 2 Beds
    • 1 Bath
    • 1,111 Sq Ft
    • Built 1955

    Last Sold Summary

    • 3% Below List Price
    • $293/SF

    Current Estimated Value $339,463

    Last Listing Agent Tracie Clawson ERA Oakcrest Realty, Inc.

    114 Harrison Ln, Winchester, VA 22602
    • /39

      Not Listed For Sale

      320 Russellcroft Rd, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 1,833 Sq Ft
      • Built 1964
      320 Russellcroft Rd, Winchester, VA 22601

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Jeanne Mezzatesta Colony Realty

  • /2

    $215,000

    • Land
    • 26,571 Sq Ft
    • $352,459 per Acre

    40 Huntersridge Rd, Winchester, VA 22602

    A rare offering in the established Oakdale Crossing Community. This 0.61 acre-lot boasts a flat topography, tucked on a quiet cul-de-sac, and framed with large lush trees. Enjoy the perfect blend of seclusion and proximity with a short drive to the Winchester Country Club, Jim Barnett Park, Major shopping & dining, and the downtown walking mall. + prime location for commuters with easy access to

    Jocelyn Tweedie Hunt Country Sotheby's International Realty

    40 Huntersridge Rd, Winchester, VA 22602
  • /15

    $1,450 Per Month

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Condo for Rent

    540 Monticello St Unit 4, Winchester, VA 22601

    Discover this cozy and convenient 2-Bedroom, 1-Bath Rental located right in the heart of Winchester. This upstairs unit features a well-sized Kitchen, comfortable Living Room, 2 Bedrooms, 1 Full Bath, in-until Laundry Room, and a rear porch for your convenience. this home makes everyday living easy. Great city location with easy access to shopping, dining, and more!Perfect for anyone looking

    Laura King MarketPlace REALTY

    540 Monticello St Unit 4, Winchester, VA 22601
  • /11

    $528,057

    Sold Nov 14, 2025

    120 Webster Ct, Winchester, VA 22603

    • 3 Beds
    • 3 Baths
    • 2,264 Sq Ft
    • Built 2025

    Last Sold Summary

    • 4% Below List Price
    • $233/SF
    • 2 Days On Market

    Last Listing Agent Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

    120 Webster Ct, Winchester, VA 22603
    • /24

      Not Listed For Sale

      827 Panther Dr, Winchester, VA 22602

      • 3 Beds
      • 2 Baths
      • 1,217 Sq Ft
      • Built 2025
      827 Panther Dr, Winchester, VA 22602

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.

  • /72

    $565,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,846 Sq Ft

    109 Artillery Rd, Winchester, VA 22602

    Welcome home to this beautifully updated 4-bedroom Colonial situated on a large corner lot in a highly desirable commuter location just off Route 7. From top to bottom, this home has been thoughtfully improved, offering the perfect blend of modern updates and timeless charm. The newly updated kitchen features brand-new quartz countertops, all-new stainless steel appliances, including a gas range

    Traci Shoberg Samson Properties

    109 Artillery Rd, Winchester, VA 22602
  • /52

    $1,695

    Total Monthly Price

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

    2520 Bradford Ct, Winchester, VA 22601

    The Flats of Winchester is an SDF Residential community located in Winchester, VA, offering a blend of renovated 1- and 2-bedroom apartments. The property features front patio gardens throughout, along with a unique landscape that sets it apart from other apartment complexes while preserving the quaint charm of the surrounding communityYour new home comes freshly remodeled and equipped

    2520 Bradford Ct, Winchester, VA 22601
  • /20

    $529,990

    Sold Jan 12, 2026

    109 Sunflower Way, Winchester, VA 22603

    • 3 Beds
    • 2 Baths
    • 2,264 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $234/SF
    • 24 Days On Market

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

    109 Sunflower Way, Winchester, VA 22603
    • /10

      Not Listed For Sale

      Lots 6 & 7 Glen Ridge Rd, Winchester, VA 22602

      Lots 6 & 7 Glen Ridge Rd, Winchester, VA 22602

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.

  • /42

    $619,900

    $5K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,985 Sq Ft

    101 Poe Dr, Winchester, VA 22602

    Welcome 101 Poe Drive! You are going to swoon over this gorgeous, model-quality home located in the desirable Raven Oaks neighborhood. This beauty boasts nearly 2,800 square feet of above-grade living space, complete with four bedrooms, two and a half baths, and an amazing loft area upstairs that is currently being used as an adorable play area. Once you step inside the front door, you’ll

    Kristin Crosby Samson Properties

    101 Poe Dr, Winchester, VA 22602
  • /16

    $1,749 Per Month

    • 3 Beds
    • 1 Bath
    • 938 Sq Ft
    • House for Rent

    265 Opequon Ave, Winchester, VA 22601

    Conveniently Located Ranch home with 3 Bedrooms, 1 Bath, and full unfinished basement on a corner in town lot. Pets on a case by case basis, No Cats. If pets are approved there is a $300.00 Non-refundable pet deposit per pet.

    Steve DuBrueler Coldwell Banker Premier

    265 Opequon Ave, Winchester, VA 22601
  • /80

    $575,000

    Sold Feb 24, 2026

    3782 Wardensville Grade, Winchester, VA 22602

    • 5 Beds
    • 4 Baths
    • 3,432 Sq Ft
    • Built 1985

    Last Sold Summary

    • $168/SF
    • 152 Days On Market

    Current Estimated Value $606,369

    Last Listing Agent Amanda Gulla Preslee Real Estate

    3782 Wardensville Grade, Winchester, VA 22602
    • /10

      Not Listed For Sale

      LOT 8 Glen Ridge Rd, Winchester, VA 22602

      LOT 8 Glen Ridge Rd, Winchester, VA 22602

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.

  • /33

    $447,000

    $3K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,540 Sq Ft

    310 Longview Ave, Winchester, VA 22601

    Discover a stunning blend of Colonial and Contemporary architecture in this exquisite 3-bedroom, 2.5-bathroom residence, built in 2024. Step inside to find luxurious vinyl plank flooring and plush carpeting that exude warmth and sophistication. The gourmet kitchen is a chef's dream, equipped with high-end appliances including a sleek wall oven, cooktop, and energy-efficient refrigerator, ensuring

    Dave Milburn Coldwell Banker Realty

    310 Longview Ave, Winchester, VA 22601
  • /20

    $2,150

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    213 N Kent St, Winchester, VA 22601

    First Month FREE!! Experience walkable downtown living at 213 N. Kent Street in Historic Downtown Winchester, Virginia. This fully renovated upper-level apartment offers three bedrooms, three bathrooms, and more than 1,200 square feet of thoughtfully updated living space just steps from the Winchester Walking Mall.The modern kitchen features updated finishes and appliances, while the

    213 N Kent St, Winchester, VA 22601
  • /20

    $193,000

    Sold Oct 17, 2025

    0 Adams Rd Unit VAFV2034928, Winchester, VA 22603

    • Land
    • 10 Acres
    • $19,300 per Acre

    Last Sold Summary

    • 29 Days On Market

    Last Listing Agent Jeffrey Konrady Realty ONE Group Old Towne

    0 Adams Rd Unit VAFV2034928, Winchester, VA 22603
    • /5

      Not Listed For Sale

      0 0 Unit VAFV2034582, Winchester, VA 22602

      0 0 Unit VAFV2034582, Winchester, VA 22602

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Cathy Durbin Crum Realty, Inc.

Showing Results 241 - 280, Page 7 of 18

How to Buy a Home How to Finance a Home How to Sell a Home