Winchester County, VA Homes

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  $425,000

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  823 Woodland Ave, Winchester, VA 22601

  Charming on the outside, modern on the inside Located in a charming, very quiet neighborhood, this home offers the perfect blend of timeless character and a fully modern renovation. Featuring 3 beautifully updated levels, the home showcases new Bruce hardwood flooring throughout with no transitions, creating a seamless, elegant flow and easy mobility. Every detail has been thoughtfully upgraded

  Lenora Zaccur Coldwell Banker Realty

  823 Woodland Ave, Winchester, VA 22601
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  $1,595 Per Month

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Townhouse for Rent

  28 E Pall Mall St, Winchester, VA 22601

  Welcome to 28 E Pall Mall Street, a charming rental located just minutes from the vibrant Old Town Winchester area. This well-maintained home offers the perfect blend of comfort, convenience, and historic charm. Step inside to find spacious living areas filled with natural light, comfortable bedrooms, and a functional layout ideal for everyday living. The home features a bright kitchen with

  tiffany pollard Coldwell Banker Elite

  28 E Pall Mall St, Winchester, VA 22601
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  /36

  $525,000 Sold Nov 14, 2025

  2723 Windwood Dr, Winchester, VA 22601

  • 3 Beds
  • 3 Baths
  • 2,726 Sq Ft
  • Built 1999

  Last Sold Summary

  • $193/SF
  • 38 Days On Market

  Current Estimated Value $527,840

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

  2723 Windwood Dr, Winchester, VA 22601
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  /41

  Est $497,926 Not Listed For Sale

  2060 Taylor Grace Ct, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 1,776 Sq Ft
  • Built 2011

  2060 Taylor Grace Ct, Winchester, VA 22601

  Last Sold Summary

  • 15% Above List Price
  • $244/SF
  • 22 Days On Market

  • Last Sold Price $433,000
  • Aug 07, 2024

  Last Listing Agent Paul Gallagher Colony Realty
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  /24

  $389,990 New Construction

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

  201 Monteith Dr, Winchester, VA 22601

  End Of Row Townhome With 1 Car Garage & Rear Deck! MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level end of row home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended island that seats four at counter height, range

  DRB Homes Builder

  201 Monteith Dr, Winchester, VA 22601
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  $2,400

  Total Monthly Price

  • 3 Beds
  • 2.5 Baths
  • 1,672 Sq Ft
  • House for Rent

  504 N Loudoun St, Winchester, VA 22601

  Beautifully updated 3-bedroom, 2.5-bath home offering 1,672 SF of living space in a prime, highly walkable location just minutes from downtown (500 block of N Loudoun Street).You have the option of fully furnished living areas and partially furnished bedrooms for an additional $150/mo.Optional furnishings include:Large living room sofaDining table with two chairsKitchen

  504 N Loudoun St, Winchester, VA 22601
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  $555,000 Sold Dec 22, 2025

  2307 Stoneridge Rd, Winchester, VA 22601

  • 5 Beds
  • 3.5 Baths
  • 3,280 Sq Ft
  • Built 2016

  Last Sold Summary

  • $169/SF
  • 5 Days On Market

  Current Estimated Value $558,764

  Last Listing Agent Dave Spence RE/MAX Roots

  2307 Stoneridge Rd, Winchester, VA 22601
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  Est $575,558 Not Listed For Sale

  2044 Taylor Grace Ct, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,568 Sq Ft
  • Built 2011

  2044 Taylor Grace Ct, Winchester, VA 22601

  Last Sold Summary

  • 5% Above List Price
  • $154/SF
  • 10 Days On Market

  • Last Sold Price $549,900
  • Jun 28, 2024

  Last Listing Agent Cynthia Lee RE/MAX
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  $389,000 Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,809 Sq Ft

  328 Longview Ave, Winchester, VA 22601

  This ranch home in Winchester City has been meticulously maintained. Beautiful hardwood floors. Dining room can be converted back to a third bedroom, simply install doors that are being stored in the basement. Basement is 75% finished and offers endless possibilities. The remaining 25% provides room for ample storage and/or a workshop. New HVAC installed in 2019, new water heater (2025) has never

  Kelly Bauer Coldwell Banker Premier

  328 Longview Ave, Winchester, VA 22601
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  /13

  $1,599 Per Month

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

  3107 Shawnee Dr Unit 7, Winchester, VA 22601

  NOW ACCEPTING PETS ON A CASE BY CASE BASIS!!Beautifully Renovated Unit Two level townhome*Full size Washer & Dryer*Hardwood like Floors* Huge Brand New Eat-In Kitchen*Granite counters & Stainless Steel Appliances*Spacious bedrooms*Large closets*Individually controlled HVAC and hot water heater*Plenty of parking*1 mile from great shopping on Valley Avenue, 10 minute from downtown Winchester

  Steve DuBrueler Coldwell Banker Premier

  3107 Shawnee Dr Unit 7, Winchester, VA 22601
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  $370,000 Sold May 13, 2025

  520 N Loudoun St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,459 Sq Ft
  • Built 1930

  Last Sold Summary

  • $254/SF
  • 32 Days On Market

  Current Estimated Value $363,018

  Last Listing Agent Dan Whitacre Colony Realty

  520 N Loudoun St, Winchester, VA 22601
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  /24

  Est $335,860 Not Listed For Sale

  456 Imperial St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,722 Sq Ft
  • Built 1962

  456 Imperial St, Winchester, VA 22601

  Last Sold Summary

  • 12% Above List Price
  • $174/SF
  • 76 Days On Market

  • Last Sold Price $300,000
  • Apr 24, 2025

  Last Listing Agent Holly Porter NewTown Realty
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  $80,000

  • Land
  • 5,662 Sq Ft
  • $615,385 per Acre

  520 Highland Ave, Winchester, VA 22601

  Empty lot ready to build a home one. The lot is fully fenced with front and rear gates. The front of the lot meets the sidewalks and road of Highland Ave. The rear of the lot meets a gravel alley way that could give access to off street parking on this lot. Homes in the city are in demand, so don't miss this opportunity. Zoned HR-1Can only be used for single family dwellingsFront setback:

  Michael Sprague Samson Properties

  520 Highland Ave, Winchester, VA 22601
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  $900

  Total Monthly Price

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

  719 S Braddock St Unit Master Bedroom, Winchester, VA 22601

  719 S Braddock St Unit Master Bedroom, Winchester, VA 22601
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  /50

  $465,000 Sold Jul 10, 2025

  350 Lanny Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 2,371 Sq Ft
  • Built 1967

  Last Sold Summary

  • $196/SF
  • 22 Days On Market

  Current Estimated Value $452,298

  Last Listing Agent Sheila Pack RE/MAX Roots

  350 Lanny Dr, Winchester, VA 22601
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  Est $414,167 Not Listed For Sale

  444 Superior Ave, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 2008

  444 Superior Ave, Winchester, VA 22601

  Last Sold Summary

  • 15% Above List Price
  • $220/SF
  • 28 Days On Market

  • Last Sold Price $359,000
  • Jul 30, 2024

  Last Listing Agent Kathryn Symenow CENTURY 21 New Millennium
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  $80,000

  • Land
  • 3,484 Sq Ft
  • $1,000,000 per Acre

  24 N Pleasant Valley Rd, Winchester, VA 22601

  Ready for building! Clear open lot that is ready for a home to be built. Winchester City is the fastest growing city in the state and homes are in high demand. Don't miss your opportunity. Property has road front access as well as a gravel alley in the rear that could be used for access to off street parking.Zoned MR - medium density residential districtCan only be used for single family

  Michael Sprague Samson Properties

  24 N Pleasant Valley Rd, Winchester, VA 22601
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  $2,500 Per Month

  • 2 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • Townhouse for Rent

  7 N Loudoun St Unit 1/2, Winchester, VA 22601

  Want to be in all the action on the Old Town walking mall, in a two story loft over the quiet Winchester Book Gallery just steps from restaurants, shops, and activities? The sprawling living area is perfect to create little nooks for gatherings, a reading space, and more. The original wood floors gleam and there is tons of built in storage space. The gourmet kitchen features stainless appliances,

  Misty Weaver Samson Properties

  7 N Loudoun St Unit 1/2, Winchester, VA 22601
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  $460,000 Sold Aug 07, 2025

  2620 Stonegate Dr, Winchester, VA 22601

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

  Last Sold Summary

  • $155/SF
  • 10 Days On Market

  Current Estimated Value $458,883

  Last Listing Agent Anthony Adamovich Key Move Properties, LLC.

  2620 Stonegate Dr, Winchester, VA 22601
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  Est $417,450 Not Listed For Sale

  428 Superior Ave, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 2,288 Sq Ft
  • Built 1967

  428 Superior Ave, Winchester, VA 22601

  Last Sold Summary

  • 2% Below List Price
  • $186/SF
  • 4 Days On Market

  • Last Sold Price $425,000
  • Jul 18, 2024

  Last Listing Agent Devin Moore Innovation Properties, LLC
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  /25

  $249,990 Pending

  • 3 Beds
  • 1 Bath
  • 985 Sq Ft

  212 Shawnee Ave, Winchester, VA 22601

  Some homes are finished. Others are opportunities. This one is the second kind, and it’s the kind that doesn’t come around often in a location like this. From the outside, it already has what you can’t easily create. A stone-front cottage look, a covered front porch, and a presence that feels welcoming the moment you see it. It’s the kind of curb appeal that draws people in without trying too

  Alexander Bracke Real Broker, LLC

  212 Shawnee Ave, Winchester, VA 22601
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  $1,700

  Total Monthly Price

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

  342 Fairmont Ave Apt Unit Comfortable In-Towner, Winchester, VA 22601

  COMPLETELY FURNISHED RENTAL.Perfect for traveling professionals or students or those renovating or selling a home and are in limbo until the new home is ready. Cozy and stylish one bedroom apartment in the heart of downtown, historic Winchester. This completely furnished apartment has everything you need for a short or extended stay. Linens, pots, pans, plates, glasses, utensils,

  342 Fairmont Ave Apt Unit Comfortable In-Towner, Winchester, VA 22601
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  $438,000 Sold May 08, 2026

  21 W Pall Mall St, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 1,805 Sq Ft
  • Built 1930

  Last Sold Summary

  • 3% Above List Price
  • $243/SF
  • 10 Days On Market

  Current Estimated Value $426,065

  Last Listing Agent Allyson Lenz Compass

  21 W Pall Mall St, Winchester, VA 22601
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  Est $439,541 Not Listed For Sale

  441 Superior Ave, Winchester, VA 22601

  • 2 Beds
  • 2 Baths
  • 1,672 Sq Ft
  • Built 1998

  441 Superior Ave, Winchester, VA 22601

  Last Sold Summary

  • 5% Above List Price
  • $251/SF
  • 1 Day On Market

  • Last Sold Price $420,000
  • Dec 30, 2024

  Last Listing Agent Curtis Siever NextHome Realty Select
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  $364,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  707 E Cork St, Winchester, VA 22601

  Charming Colonial in Winchester, VA 3 Bedrooms | 2.5 Baths with additional rooms Step into timeless charm with this beautifully maintained Colonial featuring gleaming hardwood floors throughout, including a stunning custom square inlay design that adds character you simply won’t find in today’s homes.The home offers two full baths full of personality — one with a beautifully tiled shower and

  Jaclyn Michelle Berkshire Hathaway HomeServices PenFed Realty

  707 E Cork St, Winchester, VA 22601
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  $1,375 Per Month

  • 2 Beds
  • 1.5 Baths
  • 995 Sq Ft
  • Condo for Rent

  3103 Shawnee Dr Unit 11, Winchester, VA 22601

  Two level townhome*Stackable Washer & Dryer* New Carpet and Freshly painted* Eat-In Kitchen*Spacious bedrooms*Large closets*Individually controlled HVAC and hot water heater*Plenty of parking*1 mile from great shopping on Valley Avenue, 10 minute from downtown Winchester and 9 minute from Shenandoah University* Additional Charge of $25 per person for water, sewer and trash that is billed monthly.

  Ashley Crabill Coldwell Banker Premier

  3103 Shawnee Dr Unit 11, Winchester, VA 22601
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  $650,000 Sold Jul 10, 2025

  19 E Boscawen St, Winchester, VA 22601

  • 3 Beds
  • 4 Baths
  • 2,639 Sq Ft
  • Built 1900

  Last Sold Summary

  • $246/SF
  • 79 Days On Market

  Current Estimated Value $496,211

  Last Listing Agent Jen Moore ERA Oakcrest Realty, Inc.

  19 E Boscawen St, Winchester, VA 22601
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  Est $399,835 Not Listed For Sale

  417 Superior Ave, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,747 Sq Ft
  • Built 1964

  417 Superior Ave, Winchester, VA 22601

  Last Sold Summary

  • 10% Above List Price
  • $209/SF
  • 79 Days On Market

  • Last Sold Price $365,000
  • Oct 30, 2023

  Last Listing Agent Bruce Elsey Long & Foster Real Estate, Inc.
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  $257,500

  • 3 Beds
  • 1 Bath
  • 1,404 Sq Ft

  332 Opequon Ave, Winchester, VA 22601

  Adorable ranch home with great potential - TLC needed. The home has a large family room for entertainment, a rear patio for outside relaxation, and a fully fenced yard. Laminate flooring throughout the home with carpet in the family room. Selling as-is. Inspections for informational purposes only. The home is located downtown within close proximity to shopping, restaurants, Jim Barnett Park, and

  Renee Waymire Samson Properties

  332 Opequon Ave, Winchester, VA 22601
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  $1,975

  Total Monthly Price

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

  342 Fairmont Ave Unit 3, Winchester, VA 22601

  Gorgeous, large, fully furnished two bedroom apartment.Amazing location in beautiful well-established neighborhood. Just two short walking blocks to the Old Town Winchester pedestrian mall with shops, restaurants, cafes and entertainment.Located inside an 1840s hstoric house, this two bedroom apartment features original hardwood floors, high ceilings, crown molding, large windows,

  342 Fairmont Ave Unit 3, Winchester, VA 22601
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  /38

  $449,990 Sold Sep 18, 2025

  1823 Reese Ct, Winchester, VA 22601

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

  Move in Ready Sold Summary

  • $238/SF
  • 6 Days On Market

  D.R. Horton Abrams Crossing at Meadow Branch

  1823 Reese Ct, Winchester, VA 22601
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  /54

  Est $360,310 Not Listed For Sale

  444 Imperial St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,221 Sq Ft
  • Built 1959

  444 Imperial St, Winchester, VA 22601

  Last Sold Summary

  • $295/SF
  • 43 Days On Market

  • Last Sold Price $360,000
  • Dec 08, 2023

  Last Listing Agent Alexandra Brown Spring Hill Real Estate, LLC.
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  $319,900 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,699 Sq Ft

  2956 Grace St, Winchester, VA 22601

  **Brand new carpet and paint on main level** Welcome to 2956 Grace Street, this 3-bedroom 1-bath ranch-style home offers a functional layout designed for everyday living, paired with the added benefit of a fullt equipped guest suite. Whether you are accomodating extended family, hosting long-term guests or exploring rental potential, this home provides flexibility to fit a variety of

  Carolyn Young Samson Properties

  2956 Grace St, Winchester, VA 22601
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  $1,750 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft
  • Townhouse for Rent

  2906 Sorrell Ct, Winchester, VA 22601

  2-bedroom, 1.5-bathroom townhome located in Winchester, VA. The main level features a functional layout with a convenient half bath, while upstairs offers two well-sized bedrooms and a full bathroom. The property is situated for easy access to shopping, dining, and everyday amenities. Applicants must meet minimum credit and income requirements—no prior evictions.

  Marisa Varley ERA Oakcrest Realty, Inc.

  2906 Sorrell Ct, Winchester, VA 22601
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  $265,000 Sold Sep 09, 2025

  2301 Tower Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1989

  Last Sold Summary

  • $276/SF
  • 90 Days On Market

  Current Estimated Value $267,289

  Last Listing Agent Clint Pierpoint NextHome Realty Select

  2301 Tower Ave, Winchester, VA 22601
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  Est $267,401 Not Listed For Sale

  420 Royal St, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 858 Sq Ft
  • Built 1962

  420 Royal St, Winchester, VA 22601

  Last Sold Summary

  • 30% Above List Price
  • $240/SF
  • 14 Days On Market

  • Last Sold Price $206,000
  • Jun 09, 2023

  Last Listing Agent Julissa Rodriguez Vaze Realty
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  $369,900

  • 3 Beds
  • 1.5 Baths
  • 1,366 Sq Ft

  517 Dunlap St, Winchester, VA 22601

  Welcome to 517 Dunlap St — a beautifully renovated 3-bedroom, 1.5-bath home set on a nicely sized, fully fenced lot in the heart of Winchester, where modern updates meet everyday comfort and a backyard designed for making the most of every season, complete with your own private pool.The main level welcomes you with a bright and inviting layout, where the living and dining spaces flow

  Carolyn Young Samson Properties

  517 Dunlap St, Winchester, VA 22601
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  $1,395

  Total Monthly Price

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

  2640 Valley Ave Unit All Utilities Included, Winchester, VA 22601

  If interested, please call, we do not respond to email or requests. 1 Bedroom 1 Bath 600 sqft. $1395/Month 1 Year Lease. All Utilities Included. First and Security Due at Signing. Stove, dishwasher, fridge, washer, and dryer provided inside unit. Individual Unit Central heat and air. No Smoking. No Pets. $35 Application Fee. Meticulously

  2640 Valley Ave Unit All Utilities Included, Winchester, VA 22601
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  $350,000 Sold Jul 09, 2025

  1109 Opequon Ave, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1978

  Last Sold Summary

  • $292/SF
  • 4 Days On Market

  Current Estimated Value $342,468

  Last Listing Agent Stephanie Ryall Realty ONE Group Old Towne

  1109 Opequon Ave, Winchester, VA 22601
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  Est $387,615 Not Listed For Sale

  3128 Papermill Rd, Winchester, VA 22601

  • 3 Beds
  • 3 Baths
  • 1,970 Sq Ft
  • Built 2002

  3128 Papermill Rd, Winchester, VA 22601

  Last Sold Summary

  • 21% Above List Price
  • $163/SF
  • 9 Days On Market

  • Last Sold Price $321,000
  • Feb 29, 2024

  Last Listing Agent Natalie Dalecky ERA Oakcrest Realty, Inc.

Showing Results 161 - 200, Page 5 of 18