Winchester County, VA Homes

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  /3

  $2,300,000

  • Land
  • 3.51 Acres
  • $655,271 per Acre

  1721 Amherst St, Winchester, VA 22601

  3.51 AC of premier commercial land. Directly across the street from the main hospital campus on one of Winchester's main commercial corridors. Ideal for banks, medical offices, retail or restaurants.

  Marie DiLorenzo Oakcrest Commercial LLC.

  1721 Amherst St, Winchester, VA 22601
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  /7

  $1,200 Per Month

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

  434 N Kent St Unit 4, Winchester, VA 22601

  2 bedroom 1 bath 2nd floor rental apartment. This is a month to month lease. Pets considered case by case. Tenant is responsible for electricity and water/sewer. Apply online thru listers website or NVAR or VAR rental application with $50 per person application fee.

  Misty Miller OliveTree Property Group, LLC

  434 N Kent St Unit 4, Winchester, VA 22601
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  /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 $781,774

  Last Listing Agent Sheila Pack RE/MAX Roots

  1001 Armistead St, Winchester, VA 22601
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  /19

  Est $328,598 Not Listed For Sale

  2927 S Pleasant Valley Rd, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft
  • Built 1983

  2927 S Pleasant Valley Rd, Winchester, VA 22601

  Last Sold Summary

  • 6% Above List Price
  • $258/SF
  • 21 Days On Market

  • Last Sold Price $309,900
  • Jan 29, 2024

  Last Listing Agent Anna Fox NextHome Realty Select
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  /70

  $749,500

  • 6 Beds
  • 4 Baths
  • 4,672 Sq Ft

  817 Chelsea Dr, Winchester, VA 22601

  Spacious 5-6-bedroom, 4-bath brick-front rancher with a fully finished basement, offering flexible living space for today’s needs. The main level features a welcoming living room with a tray ceiling & a gas fireplace, a formal dining room with crown molding & chair rail, and a well-appointed kitchen with Corian countertops and a walk-in pantry. The primary suite is conveniently located on the

  Sheila Pack RE/MAX Roots

  817 Chelsea Dr, Winchester, VA 22601
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  /14

  $1,500 Per Month

  • 2 Beds
  • 1.5 Baths
  • 23,305 Sq Ft
  • Condo for Rent

  443 Millwood Ave Unit 5, Winchester, VA 22601

  Clean and updated 2-bedroom, 2-bath apartment ideally located near Shenandoah University and downtown Winchester. Features include a functional floor plan, in-unit washer and dryer, and two full bathrooms for added convenience. One assigned parking space conveys, plus street parking options nearby. Situated above commercial space with close proximity to local restaurants, shops, and major

  Rachel Olsen Keller Williams Realty

  443 Millwood Ave Unit 5, Winchester, VA 22601
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  /12

  $375,000 Sold Jun 30, 2025

  122 E Pall Mall St, Winchester, VA 22601

  • Studio
  • 1,372 Sq Ft
  • Built 1920

  Last Sold Summary

  • $273/SF
  • 13 Days On Market

  Last Listing Agent Kathy Colville Century 21 Redwood Realty

  122 E Pall Mall St, Winchester, VA 22601
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  /21

  Est $322,627 Not Listed For Sale

  2922 S Pleasant Valley Rd, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,060 Sq Ft
  • Built 1986

  2922 S Pleasant Valley Rd, Winchester, VA 22601

  Last Sold Summary

  • 1% Below List Price
  • $307/SF
  • 12 Days On Market

  • Last Sold Price $325,000
  • Aug 22, 2024

  Last Listing Agent Anna Fox NextHome Realty Select
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  /4

  $750,000 Under Contract

  • Land
  • 1.33 Acres
  • $563,910 per Acre

  903 N Loudoun St, Winchester, VA 22601

  Lot 2 is half in Winchester City (tax ID # 134003-35) at 903 N. Loudoun St., & half in Frederick County (tax ID #54-A-50.) Mixed use zoning HR & B2. The county side has a brick residential structure, address 909 Martinsburg Pk, and city half is cleared land/ lot. The total sq ftg is 108,325 (2 & half acres.) Road frontage on Loudoun & Martinsburg PIke is 250 feet. The rear of lot is North

  Wendy Longerbeam Coldwell Banker Elite

  903 N Loudoun St, Winchester, VA 22601
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  /39

  $2,500 Per Month

  • 4 Beds
  • 3.5 Baths
  • 1,920 Sq Ft
  • Townhouse for Rent

  1829 Harvest Dr, Winchester, VA 22601

  Brand new, pristine townhome, spacious end unit. Security system, featuring remote keyless entry and a video doorbell. Kitchen with stainless appliances and large island, opens to dining deck. Conveniently located with easy access to schools, hospital, shopping, services and major commuting thoroughfares. Landscaping maintenance and snow removal provided, city trash pick-up. Landlord requires a

  Dallas Croft Samson Properties

  1829 Harvest Dr, Winchester, VA 22601
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  /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 $262,709

  Last Listing Agent Carlos Soares Samson Properties

  423 Highland Ave, Winchester, VA 22601
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  /23

  Est $351,476 Not Listed For Sale

  2919 S Pleasant Valley Rd, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,388 Sq Ft
  • Built 1990

  2919 S Pleasant Valley Rd, Winchester, VA 22601

  Last Sold Summary

  • 1% Below List Price
  • $256/SF
  • 2 Days On Market

  • Last Sold Price $355,000
  • May 01, 2024

  Last Listing Agent Anna Fox NextHome Realty Select
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  /20

  $319,000

  • 3 Beds
  • 2 Baths
  • 1,362 Sq Ft

  553 Highland Ave, Winchester, VA 22601

  Don't miss taking a LOOK at this property with the new low price of $319K. One Way street = quiet Gorgeous Rehab - you have to see it! Secure Parking off the alley Efficient HVAC mini splits installed Washer and Dryer included

  Teri Domanski Your Home Sold Guaranteed Realty - East LLC

  553 Highland Ave, Winchester, VA 22601
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  /9

  $1,500 Per Month

  • 2 Beds
  • 1 Bath
  • 709 Sq Ft
  • House for Rent

  109 E Pall Mall St, Winchester, VA 22601

  Ready for occupancy! This single family ranch style home offers ew rear deck off the rear, nice size back yard w/ storage shed, central air and heat, separate laundry/mud room, covered front porch, and more. VAR or NVAR rental application with $50 per person application fee or your clients may apply online through listers website. No smoking. Pets case by case.

  Mandie Gladwell OliveTree Property Group, LLC

  109 E Pall Mall St, Winchester, VA 22601
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  /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 $467,039

  Last Listing Agent Dave Spence RE/MAX Roots

  711 S Braddock St, Winchester, VA 22601
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  /19

  Est $330,320 Not Listed For Sale

  2951 S Pleasant Valley Rd, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft
  • Built 1989

  2951 S Pleasant Valley Rd, Winchester, VA 22601

  Last Sold Summary

  • 1% Above List Price
  • $272/SF
  • 4 Days On Market

  • Last Sold Price $326,000
  • Jul 25, 2024

  Last Listing Agent Anna Fox NextHome Realty Select
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  /38

  $319,000

  • 2 Beds
  • 2 Baths
  • 1,382 Sq Ft

  31 E Germain St, Winchester, VA 22601

  IMPROVED PRICING! Nestled in the heart of Winchester City’s Historic District and walkable to shops and restaurants, this charming 2-bedroom, 2-bathroom gem is a rare find! The large front porch has great curb appeal and is the perfect place for outdoor lounging. The home is filled with natural light that illuminates the clean white walls and warm hardwood flooring. The living room flows into the

  Sue-Anne DeBergh Compass

  31 E Germain St, Winchester, VA 22601
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  /5

  $1,050 Per Month

  • 1 Bed
  • 1 Bath
  • 4,672 Sq Ft
  • Condo for Rent

  418 N Loudoun St Unit 3, Winchester, VA 22601

  Historic Downtown Winchester: 2nd floor 1 bedroom apartment AVAILABLE NOW for rent! Water/sewer/trash included, tenant pays electric. No smoking and no animals please. $50 app fee paid by cash or money order or you may apply online thru website.

  Mandie Gladwell OliveTree Property Group, LLC

  418 N Loudoun St Unit 3, Winchester, VA 22601
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  /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 $1,190,972

  Last Listing Agent Natalie Langford ERA Oakcrest Realty, Inc.

  819 Armistead St, Winchester, VA 22601
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  /19

  Est $329,661 Not Listed For Sale

  2947 S Pleasant Valley Rd, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft
  • Built 1986

  2947 S Pleasant Valley Rd, Winchester, VA 22601

  Last Sold Summary

  • 5% Above List Price
  • $263/SF
  • 1 Day On Market

  • Last Sold Price $315,000
  • Mar 15, 2024

  Last Listing Agent Anna Fox NextHome Realty Select
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  /38

  $449,990 New Construction

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

  1819 Reese Ct, Winchester, VA 22601

  1819 Reese Court is a move-in ready 3-level townhome with full brick front in Winchester, VA. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained oak stairs lead you to the main level with LVP flooring. The kitchen is equipped with beautiful quartz countertops, sasparilla cabinets, and stainless-steel appliances. The upper

  D.R. Horton Builder

  1819 Reese Ct, Winchester, VA 22601
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  /21

  $2,750 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,424 Sq Ft
  • House for Rent

  1929 Melvor Ln, Winchester, VA 22601

  This 4-bedroom, 2.5-bath home offers generous room sizes throughout, giving you the space you actually need for everyday living, working from home, or entertaining. Freshly updated with brand-new carpet and fresh paint, the home feels clean, bright, and move-in ready from the moment you walk in.The large primary suite is a true highlight, featuring an expansive layout and a private en-suite

  Bailey Cooper RE/MAX Gateway

  1929 Melvor Ln, Winchester, VA 22601
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  /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 $801,753

  Last Listing Agent Kiran K. Morzaria Parekh Samson Properties

  939 Buckner Dr, Winchester, VA 22601
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  /28

  Est $347,564 Not Listed For Sale

  2943 S Pleasant Valley Rd, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,479 Sq Ft
  • Built 1962

  2943 S Pleasant Valley Rd, Winchester, VA 22601

  Last Sold Summary

  • 1% Above List Price
  • $232/SF
  • 14 Days On Market

  • Last Sold Price $342,500
  • Mar 21, 2025

  Last Listing Agent Anna Fox NextHome Realty Select
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  /31

  $349,000

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  608 Dunlap St, Winchester, VA 22601

  Charming 3-bedroom, 1-bath ranch-style home in a highly convenient Winchester location! This well-maintained home is in great condition and has been freshly painted, offering a clean, move-in ready feel. Featuring beautiful hardwood floors throughout and a fully fenced backyard—perfect for pets, entertaining, or relaxing evenings. Central heating and air conditioning for year-round comfort.

  Richard Butcher Coldwell Banker Premier

  608 Dunlap St, Winchester, VA 22601
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  /30

  $1,850 Per Month

  • 3 Beds
  • 1 Bath
  • 1,280 Sq Ft
  • House for Rent

  540 Bellview Ave, Winchester, VA 22601

  Charming one-level rental located just 5 minutes from historic Old Town Winchester, with convenient access to I-81 for easy commuting. This home features beautiful hardwood floors throughout, a spacious living room with a cozy fireplace, and a formal dining room perfect for entertaining. The kitchen offers direct access to the backyard, making indoor-outdoor living a breeze. Three well-sized

  Heloisa Amar Samson Properties

  540 Bellview Ave, Winchester, VA 22601
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  /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 $461,691

  Last Listing Agent Gillian Greenfield Coldwell Banker Premier

  407 Jefferson St, Winchester, VA 22601
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  /13

  Est $375,984 Not Listed For Sale

  2912 Grace St, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft
  • Built 1994

  2912 Grace St, Winchester, VA 22601

  Last Sold Summary

  • 11% Above List Price
  • $271/SF
  • 24 Days On Market

  • Last Sold Price $338,000
  • May 15, 2023

  Last Listing Agent Liz Rutherford ERA Oakcrest Realty, Inc.
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  /37

  $325,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,053 Sq Ft

  624 Butler Ave, Winchester, VA 22601

  Charming ranch home nestled on a no-through street, offering both privacy and convenience. This well maintained property features 3 beds and 1.5 baths, including a primary suite. Enjoy spacious living in the large family room, perfect for relaxing or entertaining. The home has extensive landscaped with a fully fenced rear yard, ideal for outdoor gatherings, pets, or gardening. A sizeable shed

  Vicki Broy RE/MAX Roots

  624 Butler Ave, Winchester, VA 22601
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  /23

  $3,200 Per Month

  • 4 Beds
  • 3.5 Baths
  • 1,680 Sq Ft
  • House for Rent

  429 Circle Dr, Winchester, VA 22601

  JORGE CABRERA J&C Real Estate Solution, LLC

  429 Circle Dr, Winchester, VA 22601
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  /49

  $528,000 Sold Jun 24, 2025

  645 Beehive Way, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,748 Sq Ft
  • Built 2007

  Last Sold Summary

  • $192/SF
  • 19 Days On Market

  Current Estimated Value $537,790

  Last Listing Agent Laura White ERA Oakcrest Realty, Inc.

  645 Beehive Way, Winchester, VA 22601
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  /25

  Est $334,705 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

  • 20% Above List Price
  • $224/SF
  • 12 Days On Market

  • Last Sold Price $280,000
  • Dec 15, 2023

  Last Listing Agent Anna Fox NextHome Realty Select
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  /11

  $699,900

  • Studio
  • 3,190 Sq Ft

  434 Fairmont Ave, Winchester, VA 22601

  ATTENTION ALL INVESTORS OR FUTURE LANDLORDS COME CHECKOUT THIS MULTI FAMILY 3 UNIT PROPERTY. IT CONSIST OF 2 HOUSES. EACH UNIT IS A 2 BED 1BATH EACH HAVE STOVE REFRIGERATOR MICROWAVE WASHER DRYER. CURRENTLY FULLY RENTED. SO NOW IS YOUR CHANCE TO OWN A TURNKEY RENTAL PROPERTY ALL WELL MAINTAINED WITH OFF STREET PARKING. CLOSE TO DOWNTOWN & SHOPPINGRESTRICTED SHOWINGS. NEW PIC'S COMING SOON.

  Richard Kozlowski Long & Foster Real Estate, Inc.

  434 Fairmont Ave, Winchester, VA 22601
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  /13

  $1,395 Per Month

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

  515 N Loudoun St Unit 2, Winchester, VA 22601

  LANDLORD PAYS UTILITIES - INCLUDING HEAT! Affordable old-fashioned charmer near downtown Winchester. Spacious 1-BR apartment with den in a quaint 4-unit building. Exposed brick and lovely hardwood floors. Living Room. Galley kitchen. Landlord pays heat, electricity, water & sewer, and city trash pick up. Parking in rear. Minimum 1-year lease. Longer lease preferred. Renter's insurance required.

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  515 N Loudoun St Unit 2, Winchester, VA 22601
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  /37

  $429,000 Sold May 09, 2025

  200 E Piccadilly St, Winchester, VA 22601

  • 3 Beds
  • 3.5 Baths
  • 2,052 Sq Ft
  • Built 2022

  Last Sold Summary

  • $209/SF
  • 364 Days On Market

  Current Estimated Value $437,002

  Last Listing Agent Jason Aikens RE/MAX Roots

  200 E Piccadilly St, Winchester, VA 22601
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  /19

  Est $325,974 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

  • 2% Above List Price
  • $266/SF
  • 67 Days On Market

  • Last Sold Price $319,000
  • Aug 01, 2024

  Last Listing Agent Anna Fox NextHome Realty Select
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  /47

  $985,000 Pending

  • 7 Beds
  • 5.5 Baths
  • 6,540 Sq Ft

  1020 Breckinridge Ln, Winchester, VA 22601

  This property exudes luxury multigenerational living in Meadowbranch! • Main level bedroom + bath• 6500 sq ft• Wet bar in primary suite• 3-car garage• No HOA• Backing to trees, and more..... Approximately 6,500 finished square feet of living space! A place to grow, gather, and stay awhile! A brick-paved, rocking chair-worthy, front porch sets the tone, and the charming side

  Sheila Pack RE/MAX Roots

  1020 Breckinridge Ln, Winchester, VA 22601
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  /14

  $1,650 Per Month

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

  1105 Franklin St Unit 1105, Winchester, VA 22601

  2 levels TOWNHOUSE, 2 bathrooms and 2 bedroom with large walking closet, large living room and Eat in kitchen with new Laundry set, near I-81,Rt-70, Rt 50 and medical college, hospital, Amazon & many auto warehouses, TREK & many industrial companies, also 35 minutes to one hour drive for many NOVA SUBURB like Leesburg, Dulles airport, DC Metro, Tyson’s corner and Charleston casino and near by

  Ram Beladia First American Real Estate

  1105 Franklin St Unit 1105, Winchester, VA 22601
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  /3

  $271,000 Sold Jul 01, 2025

  421 Superior Ave, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,197 Sq Ft
  • Built 1965

  Last Sold Summary

  • $226/SF
  • 23 Days On Market

  Current Estimated Value $426,837

  Last Listing Agent Cathy Caniford Crossroads, Realtors

  421 Superior Ave, Winchester, VA 22601
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  /21

  Est $354,002 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

  • $256/SF
  • 18 Days On Market

  • Last Sold Price $355,000
  • Jun 13, 2024

  Last Listing Agent Anna Fox NextHome Realty Select

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