Winchester, VA Homes

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  $620,000 Coming Soon

  • 5 Beds
  • 3.5 Baths
  • 4,500 Sq Ft

  211 Lynnehaven Dr, Winchester, VA 22602

  Professional Photos Coming Soon! Spacious 5BR 3.5BA Colonial on .33 acre fenced yard. Finished lower level for added comfort. Features Kitchen with island; formal dining area, formal living room, office/den. Spacious primary bedroom with large walk in closet. Across from Greenwood Mill Elem School; great commuter location. Must See to Appreciate!

  Toni Carone Long & Foster Real Estate, Inc.

  211 Lynnehaven Dr, Winchester, VA 22602
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  /31

  $1,500 per month

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Townhouse for Rent

  127-A Peyton St, Winchester, VA 22601

  Gorgeous two story apartment with private entrance in the heart of historic downtown Winchester. Walking distance from the Old Town Winchester pedestrian mall with shops, restaurants, cafes and entertainment and the beautiful Handley library.Huge Two bedroom 1.5 bath Apartment with beautiful details located in the bottom two levels of a four story house built in the early 1890s. This is a

  127-A Peyton St, Winchester, VA 22601
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  /41

  $525,000 Sold Dec 11, 2025

  101 Dutton Place, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 2,517 Sq Ft
  • Built 1967

  Last Sold Summary

  • $209/SF
  • 29 Days On Market

  Last Listing Agent Lisa Behr Coldwell Banker Premier

  101 Dutton Place, Winchester, VA 22601
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  /11

  Est $225,603 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  164 Brookland Ct Unit 11, Winchester, VA 22602

  164 Brookland Ct Unit 11, Winchester, VA 22602
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  $339,990 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  163 Denny Ln, Winchester, VA 22603

  Saturdauy, January 4pm-6pm and Sunday, January 18th 11am-1pm. Excellent outdoor workspace and storage on the east side of Winchester. NO HOA - This property offers a detached two-car carport, a wired shed/workshop, and a wrap-around paved driveway, providing ideal space for vehicles, tools, hobbies, and additional parking. AMAZING LOCATION! Right off of Rt.7 and close proximity to 81, you can't

  Robin Gebhardt EXP Realty, LLC

  163 Denny Ln, Winchester, VA 22603
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  /33

  $2,600 per month

  • 3 Beds
  • 2.5 Baths
  • 1,637 Sq Ft
  • House for Rent

  226 Munsee Cir, Winchester, VA 22602

  Discover modern living at its finest in this stunning 2025-built smart home located near the charming city of Winchester, VA. This beautifully designed residence features three spacious bedrooms and 2.5 elegantly appointed bathrooms, providing ample space for comfort and relaxation. Sync home with your smart device. The open-concept layout seamlessly integrates the living, dining, and kitchen

  Alain Gemond Davies Realty, Inc.

  226 Munsee Cir, Winchester, VA 22602
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  $110,000 Sold Sep 08, 2025

  116-118 W Leicester St, Winchester, VA 22601

  • Land
  • 0.12 Acre
  • $916,667 per Acre

  Last Sold Summary

  • 309 Days On Market

  Current Estimated Value $107,000

  Last Listing Agent Kim Hurst MarketPlace REALTY

  116-118 W Leicester St, Winchester, VA 22601
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  /35

  Est $241,480 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  147 Brookland Ct Unit 6, Winchester, VA 22602

  147 Brookland Ct Unit 6, Winchester, VA 22602
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  /2

  $625,000 Coming Soon

  • 5 Beds
  • 3.5 Baths
  • 3,494 Sq Ft

  127 Kinross Dr, Winchester, VA 22602

  A peaceful setting at the edge of Winchester pairs nicely with everyday convenience in this well-cared-for home. The neighborhood feel is quiet and comfortable, with easy in-and-out access that helps keep daily routines running smoothly, even during peak times. Shopping, dining, and community favorites in Winchester are close by, and nearby commuter routes make it simple to stay connected. Set on

  Sarah Reynolds Keller Williams Realty

  127 Kinross Dr, Winchester, VA 22602
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  /77

  $1,650 per month

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

  342 Fairmont Ave Unit 5 FULLY FURNISHED RENTAL Retro Loves Company, Winchester, VA 22601

  COMPLETELY FURNISHED RENTALPerfect for traveling professionals or students.Furnished one bedroom located behind the beautiful Handley library. This quaint one bedroom apartment is on the 3rd floor of a historic home facing Fairmont Ave. It has terrific views and a spectacular view of fireworks on Apple Blossom, July 4th and New Years Eve. Beautiful details and wainscotting, built in

  342 Fairmont Ave Unit 5 FULLY FURNISHED RENTAL Retro Loves Company, Winchester, VA 22601
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  /2

  $1,300 Sold Aug 18, 2025

  Lot 4 Quail, Winchester, VA 22602

  • Land
  • 0 Acre

  Last Sold Summary

  • 138 Days On Market

  Last Listing Agent Kaitlyn Behr Samson Properties

  Lot 4 Quail, Winchester, VA 22602
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  /17

  Est $248,155 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  157 Brookland Terrace Unit 10, Winchester, VA 22602

  157 Brookland Terrace Unit 10, Winchester, VA 22602
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  $489,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,401 Sq Ft

  107 Tucks Cir, Winchester, VA 22602

  Welcome to this truly special, lovingly maintained one-level home in desirable Pioneer Heights, ideally located just minutes from Route 7 East for an easy commute. Situated on a quiet cul-de-sac, this well-built residence blends timeless charm with thoughtful updates throughout.Major improvements include new granite countertops in the kitchen, updated bathrooms with new vanities, specialty

  Kathrin Donovan Keller Williams Realty

  107 Tucks Cir, Winchester, VA 22602
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  /10

  $1,950 per month

  • 3 Beds
  • 2 Baths
  • 1,178 Sq Ft
  • House for Rent

  2019 Senseny Rd, Winchester, VA 22602

  THIS IS THE ONE! GREAT Commuter Location! This incredibly renovated home to appreciate the owners commitment to detail & quality. Home shows extremely well. Lots of care and attention to detail. Ideally sited on large lot. Hardwood floors, ceramic baths, beautiful cabinets, floored attic for storage. JUST MOVE IN!

  Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  2019 Senseny Rd, Winchester, VA 22602
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  /27

  $369,990 Sold Sep 18, 2025

  106 Pomo Ln, Winchester, VA 22602

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $247/SF
  • 41 Days On Market

  D.R. Horton Retreat at Winding Creek - Townhomes

  106 Pomo Ln, Winchester, VA 22602
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  /18

  Est $237,130 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  115 Brookland Terrace, Winchester, VA 22602

  115 Brookland Terrace, Winchester, VA 22602
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  $519,900

  • 3 Beds
  • 1.5 Baths
  • 2,177 Sq Ft

  216 Fairmont Ave, Winchester, VA 22601

  Classy colonial on the stately Fairmont Avenue with million dollar homes nearby, walking mall in close proximity with a plethora of boutique shops and eateries. The 2000 square feet is designed for comfort and coziness accented by 9ft ceilings, sunlit formal rooms, a well appointed kitchen, spacious bedrooms, adorable loft on 3rd level for a playroom/den/office, and the best part is entering your

  Dave Spence RE/MAX Roots

  216 Fairmont Ave, Winchester, VA 22601
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  /40

  $2,150 per month

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

  1019 Berryville Ave Unit The Queen of Winchester, Winchester, VA 22601

  The Queen of WinchesterTitle: The Queen of Winchester — Spacious 3-Bedroom Retreat with Style & ComfortDescription:Welcome to The Queen of Winchester — a beautifully appointed 3-bedroom, 2-bath residence blending comfort with modern charm. This elegant home features a bright, open-concept living space featuring abundant natural light, stylish finishes, and thoughtful design

  1019 Berryville Ave Unit The Queen of Winchester, Winchester, VA 22601
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  /28

  $490,000 Sold May 20, 2025

  102 Yurok Ct, Winchester, VA 22602

  • 4 Beds
  • 2.5 Baths
  • 1,953 Sq Ft
  • Built 2025

  Last Sold Summary

  • $251/SF
  • 45 Days On Market

  Current Estimated Value $490,886

  Last Listing Agent Tracy Jennings D R Horton Realty of Virginia LLC

  102 Yurok Ct, Winchester, VA 22602
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  /26

  Est $392,798 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  444 Superior Ave, Winchester, VA 22601

  444 Superior Ave, Winchester, VA 22601
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  $200,000

  • Land
  • 5 Acres
  • $40,000 per Acre

  Lot B Cather Ln, Winchester, VA 22602

  Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

  Kaitlyn Behr Samson Properties

  Lot B Cather Ln, Winchester, VA 22602
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  /17

  $2,300 per month

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft
  • Townhouse for Rent

  180 Munsee Cir, Winchester, VA 22602

  ** Move In Special: Approved applicants who move in January 2026 on an 18–28 month lease will receive one month of free rent. ** This brand-new townhome sits in a prime spot just off Route 7, making commuting simple. Inside, you’ll find a bright 4-bed, 3.5-bath layout with a fully upgraded kitchen, granite counters, stainless steel appliances, and a generous island that works well for cooking or

  Rachel Olsen Keller Williams Realty

  180 Munsee Cir, Winchester, VA 22602
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  /41

  $318,000 Sold Jan 09, 2026

  206 Eastside Ln, Winchester, VA 22602

  • 3 Beds
  • 3.5 Baths
  • 1,886 Sq Ft
  • Built 2006

  Last Sold Summary

  • $169/SF
  • 68 Days On Market

  Last Listing Agent Adam Brand Pearson Smith Realty, LLC

  206 Eastside Ln, Winchester, VA 22602
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  /24

  Est $420,051 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,288 Sq Ft

  428 Superior Ave, Winchester, VA 22601

  428 Superior Ave, Winchester, VA 22601
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  /70

  $379,000

  • 3 Beds
  • 2.5 Baths
  • 1,631 Sq Ft

  313 Beaver Trail, Winchester, VA 22602

  Ring in the New Year with the perfect home! Beautiful Craftsman-style home in great Shawneeland location. Over 1600 Finished Square Feet with a Full Unfinished Basement. 3 Bedrooms, 2.5 Baths. Main level Primary Bedroom with Full Bath. Engineered Hardwood flooring in Living Room, Family Room, Dining Area and Kitchen, Upgraded Cabinetry throughout home. Oak Staircase and Railing. Upper Level has 2

  Dana Durr CENTURY 21 New Millennium

  313 Beaver Trail, Winchester, VA 22602
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  /17

  $1,695 per month

  • 3 Beds
  • 1.5 Baths
  • 2,000 Sq Ft
  • Townhouse for Rent

  312 Amherst St, Winchester, VA 22601

  Unique historic duplex in old town Winchester, 3 bedrooms plus extra room for office or storage. Enjoy all of the convenience of living downtown within walking distance to Winchesters Old Town Events, Shops and Dining, Winchester Little Theater and MSV. Over 2000 sq. ft. of space, Newly refinished hardwood throughout. Fresh paint in most rooms. Washer/Dryer, nice size kitchen, front and rear

  312 Amherst St, Winchester, VA 22601
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  /8

  $600,000 Sold Mar 25, 2025

  229 S Pleasant Valley Rd, Winchester, VA 22601

  • Land
  • 3.69 Acres
  • $162,602 per Acre

  Last Sold Summary

  • 629 Days On Market

  Current Estimated Value $493,393

  Last Listing Agent Gillian Greenfield Coldwell Banker Premier

  229 S Pleasant Valley Rd, Winchester, VA 22601
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  /43

  Est $448,892 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,672 Sq Ft

  441 Superior Ave, Winchester, VA 22601

  441 Superior Ave, Winchester, VA 22601
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  $365,000 New Construction

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

  508 Grouse Dr, Winchester, VA 22602

  Nestled in the charming Wilde Acres community, this stunning new construction home, completed in 2025, offers a perfect blend of modern design and traditional comfort. The Colonial architectural style, adorned with durable vinyl siding, invites you into a warm and welcoming space. Step inside to discover a thoughtfully designed interior featuring a traditional floor plan that seamlessly connects

  Steve DuBrueler Coldwell Banker Premier

  508 Grouse Dr, Winchester, VA 22602
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  /15

  $1,400 per month

  • 2 Beds
  • 1 Bath
  • 1,045 Sq Ft
  • House for Rent

  434 Fairmont Ave Unit 1, Winchester, VA 22601

  Price Reduced Come Checkout This First Floor 2 bedroom apartment. Home was renovated 2023, New Kitchen Cabinets, In house Laundry, Full Bath, Large Front Room & Dining Room. Off Street Parking Close to Downtown & Shopping

  Richard Kozlowski Long & Foster Real Estate, Inc.

  434 Fairmont Ave Unit 1, Winchester, VA 22601
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  /35

  $359,641 Sold Nov 14, 2025

  153 Denny, Winchester, VA 22603

  • 3 Beds
  • 3 Baths
  • 1,644 Sq Ft
  • Built 2010

  Last Sold Summary

  • $219/SF
  • 14 Days On Market

  Last Listing Agent Stephanie Ryall Realty ONE Group Old Towne

  153 Denny, Winchester, VA 22603
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  /39

  Est $395,335 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,747 Sq Ft

  417 Superior Ave, Winchester, VA 22601

  417 Superior Ave, Winchester, VA 22601
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  $699,900

  • 4 Beds
  • 3.5 Baths
  • 3,475 Sq Ft

  132 Amherst St, Winchester, VA 22601

  Step back in time with this Beautifully preserved VICTORIAN Brick Home Built in 1880, a true piece of Winchester's history. This is a Registered Historic Property that showcases original architectural details, high ceilings, ornate trim, and original wood floors that reflect the artistry of a bygone era. A Well Designed Addition has allowed for generous space along with modern comfort and

  Jodi Costello ERA Oakcrest Realty, Inc.

  132 Amherst St, Winchester, VA 22601
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  $1,450 per month

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft
  • Townhouse for Rent

  125 Peyton St, Winchester, VA 22601

  Beautiful and spacious- this HUGE two story apartment has architectural charm in a lovely historic, well-established neighborhood in downtown Winchester, Virginia. We are just two short walking blocks from the Old Town Winchester pedestrian mall with shops, restaurants, cafes, museums and entertainment. Excellent location. Excellent neighbors and neighborhood. Located inside a very large

  125 Peyton St, Winchester, VA 22601
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  /72

  $700,000 Sold Oct 29, 2025

  292 Green Spring Rd, Winchester, VA 22603

  • 4 Beds
  • 4.5 Baths
  • 4,320 Sq Ft
  • Built 1990

  Last Sold Summary

  • $162/SF
  • 87 Days On Market

  Last Listing Agent Katie Landi Jordan Samson Properties

  292 Green Spring Rd, Winchester, VA 22603
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  /54

  Est $357,862 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,221 Sq Ft

  444 Imperial St, Winchester, VA 22601

  444 Imperial St, Winchester, VA 22601
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  /17

  $644,990 New Construction

  • 5 Beds
  • 4 Baths
  • 3,828 Sq Ft

  128 Wagtail Ln, Winchester, VA 22603

  Brand New Matisse is Ready for Move In at Hiatt Pointe at Snowden Bridge, a community for those 55 or better! The heart of the home is an open-concept haven, seamlessly blending a gourmet kitchen, dining room, and spacious family room. The kitchen, a chef's dream, features a functional island, abundant storage, Carrrara Mist Quartz counters, burlap and flagstone stained cabinets plus a large

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  128 Wagtail Ln, Winchester, VA 22603
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  /20

  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 1,298 Sq Ft
  • House for Rent

  239 McDonald Rd, Winchester, VA 22602

  Renovated Farmhouse for Rent West of Winchester! This nicely updated and well-maintained 3-bedroom, 2-bath farmhouse features a main-level primary suite, a welcoming white kitchen with stainless steel appliances and new granite countertops, and an open main-level layout with a spacious living room, dining area, second full bath, and a dedicated office/study with space for a mudroom.Set on one

  Rachael Duvall TTR Sotheby's International Realty

  239 McDonald Rd, Winchester, VA 22602
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  /2

  $800,000 Sold Oct 29, 2025

  601 Fall Run Ln, Winchester, VA 22602

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft
  • Built 2022

  Last Sold Summary

  • $368/SF
  • 75 Days On Market

  Last Listing Agent Theo Theologis Slones Real Estate

  601 Fall Run Ln, Winchester, VA 22602
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  /10

  Est $270,510 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 858 Sq Ft

  420 Royal St, Winchester, VA 22601

  420 Royal St, Winchester, VA 22601

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