Winchester County, VA Homes

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  /36

  $320,000

  • 3 Beds
  • 3 Baths
  • 1,281 Sq Ft

  115 S Purcell Ave, Winchester, VA 22601

  Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. Great investment opportunity! Currently tenant-occupied, offering

  Matthew Berry MarketPlace REALTY

  115 S Purcell Ave, Winchester, VA 22601
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  /10

  $1,499 Per Month

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

  3107 Shawnee Dr Unit 11, Winchester, VA 22601

  *** NOW ACCPETING PETS ON 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 and

  Steve DuBrueler Coldwell Banker Premier

  3107 Shawnee Dr Unit 11, Winchester, VA 22601
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  /64

  $615,900 Sold Jan 05, 2026

  400 Handley Ave, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,575 Sq Ft
  • Built 1928

  Last Sold Summary

  • $239/SF
  • 12 Days On Market

  Current Estimated Value $590,067

  Last Listing Agent Jeff Boppe Long & Foster Real Estate, Inc.

  400 Handley Ave, Winchester, VA 22601
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  /22

  Est $302,150 Not Listed For Sale

  313 Summit Ave, Winchester, VA 22601

  • 2 Beds
  • 1 Bath
  • 954 Sq Ft
  • Built 1951

  313 Summit Ave, Winchester, VA 22601

  Last Sold Summary

  • 6% Above List Price
  • $299/SF
  • 25 Days On Market

  • Last Sold Price $285,000
  • Jul 30, 2024

  Last Listing Agent Susan Wathen EXP Realty, LLC
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  /9

  $150,000

  • Land
  • 18,295 Sq Ft
  • $357,143 per Acre

  1322 Vanceright Cir, Winchester, VA 22601

  Tucked away on a quiet cul-de-sac, this 0.4174-acre lot offers a fantastic opportunity to build your dream home in a highly desirable Winchester location. Enjoy the convenience of being just minutes from Handley High School and the charm, dining, and shopping of downtown Winchester. The property features a 30' easement, allowing for access while still providing ample space for your vision. With

  John Scully Colony Realty

  1322 Vanceright Cir, Winchester, VA 22601
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  /14

  $1,395

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Townhouse for Rent

  224 East St, Winchester, VA 22601

  2 Bedroom 1 Bath townhome with freshly refinished hardwood floors throughout, updated kitchen and bath, full unfinished basement, washer/dryer hookup and a great little play area for the kids. Convenient location! Pet friendlyOil heat 2 Bedroom 1 Bath

  224 East St, Winchester, VA 22601
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  /45

  $515,000 Sold Jul 29, 2025

  331 Ridge Ave, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 1,881 Sq Ft
  • Built 1965

  Last Sold Summary

  • $274/SF
  • 15 Days On Market

  Current Estimated Value $517,621

  Last Listing Agent Lori Bales Keller Williams Realty

  331 Ridge Ave, Winchester, VA 22601
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  /29

  Est $304,888 Not Listed For Sale

  2917 First St, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft
  • Built 1952

  2917 First St, Winchester, VA 22601

  Last Sold Summary

  • 11% Above List Price
  • $220/SF
  • 90 Days On Market

  • Last Sold Price $275,000
  • Mar 07, 2024

  Last Listing Agent James King RE/MAX
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  /17

  $215,000

  • Land
  • 15,681 Sq Ft
  • $597,222 per Acre

  506 Fairmont Ave, Winchester, VA 22601

  NEW CITY LOT! This newly configured lot in the heart of downtown Winchester has been expanded and is ready for you to build your dream home. Featuring a width of approximately 100 feet, you have plenty of space to accommodate nearly any home of your choice. As a bonus, the driveway will be on the neighboring lot, which allows even more buildable space. Additionally, you do not have to worry about

  Dan Whitacre Colony Realty

  506 Fairmont Ave, Winchester, VA 22601
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  /8

  $1,350 Per Month

  • 1 Bed
  • 1 Bath
  • 2,058 Sq Ft
  • Condo for Rent

  36 S Cameron St Unit 2, Winchester, VA 22601

  Charming 1-bedroom, 1-bath apartment located in the heart of historic downtown Winchester! This inviting home features a bright living room with beautiful built-in shelving and passthrough openings to the kitchen, creating an open and connected feel. The updated kitchen includes stainless steel appliances, a stylish tiled backsplash, granite countertops, and crisp white cabinetry. Enjoy the

  James King RE/MAX Roots

  36 S Cameron St Unit 2, Winchester, VA 22601
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  /30

  $285,000 Sold Jan 30, 2026

  1116 Opequon Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft
  • Built 1972

  Last Sold Summary

  • $242/SF
  • 19 Days On Market

  Current Estimated Value $282,181

  Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.

  1116 Opequon Ave, Winchester, VA 22601
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  /31

  Est $289,263 Not Listed For Sale

  2944 Second St, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 850 Sq Ft
  • Built 1953

  2944 Second St, Winchester, VA 22601

  Last Sold Summary

  • 14% Above List Price
  • $298/SF
  • 126 Days On Market

  • Last Sold Price $253,300
  • Jun 09, 2023

  Last Listing Agent Amira Wali Spring Hill Real Estate, LLC.
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  /55

  $545,000

  • 3 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  308 Ridge Ave, Winchester, VA 22601

  Charming all-brick ranch offering comfortable one-level living in a highly convenient location! This well-maintained home features 3 bedrooms and 2 baths on the main level, along with a spacious living room highlighted by a cozy fireplace. A formal dining room provides the perfect space for entertaining, while the kitchen offers ample workspace and connects conveniently to the main-level laundry

  John Scully Colony Realty

  308 Ridge Ave, Winchester, VA 22601
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  /32

  $1,495

  Total Monthly Price

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

  2550 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

  2550 Bradford Ct, Winchester, VA 22601
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  /28

  $304,900 Sold Oct 02, 2025

  2923 S Pleasant Valley Rd, Winchester, VA 22601

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

  Last Sold Summary

  • $355/SF
  • 3 Days On Market

  Current Estimated Value $301,904

  Last Listing Agent Anna Fox NextHome Realty Select

  2923 S Pleasant Valley Rd, Winchester, VA 22601
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  /19

  Est $324,614 Not Listed For Sale

  2928 First St, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,472 Sq Ft
  • Built 1972

  2928 First St, Winchester, VA 22601

  Last Sold Summary

  • 22% Above List Price
  • $180/SF
  • 11 Days On Market

  • Last Sold Price $265,000
  • Aug 25, 2023

  Last Listing Agent Kimberly Schroeder Long & Foster Real Estate, Inc.
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  /97

  $510,000

  • 4 Beds
  • 2.5 Baths
  • 1,798 Sq Ft

  720 S Kent St, Winchester, VA 22601

  Welcome to the beautifully preserved American Foursquare where music legend Patsy Cline once lived with her mother—and later, with her husband, Charlie Dick. Built in 1931, this four-bedroom, one-and-a-half-bath home blends timeless character with thoughtful updates, all wrapped in the charm of one of Winchester’s most historic neighborhoods. Inside, you’ll find nearly 1,800 square feet of living

  Krissy Cruse Pearson Smith Realty, LLC

  720 S Kent St, Winchester, VA 22601
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  /10

  $2,195 Per Month

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft
  • House for Rent

  122 Morningside Dr, Winchester, VA 22601

  This home Features 3 bedrooms - 1 full bath. Finished attic for possibility for an additional bedroom or use as office space or rec room. Unfinished basement for lots of storage. Rear deck. Off street parking. No Cats, Dogs case by case with non-refundable pet deposit. $50 application fee per applicant. Oil Heat, and washer/dryer are as is

  Ashley Crabill Coldwell Banker Premier

  122 Morningside Dr, Winchester, VA 22601
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  /28

  $300,000 Sold Mar 26, 2026

  501 Battle Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,789 Sq Ft
  • Built 1946

  Last Sold Summary

  • $168/SF
  • 28 Days On Market

  Current Estimated Value $298,134

  Last Listing Agent Susan Caulfield Pearson Smith Realty, LLC

  501 Battle Ave, Winchester, VA 22601
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  /31

  Est $265,560 Not Listed For Sale

  545 Armour Dale, Winchester, VA 22601

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft
  • Built 1954

  545 Armour Dale, Winchester, VA 22601

  Last Sold Summary

  • 3% Below List Price
  • $353/SF
  • 10 Days On Market

  • Last Sold Price $275,000
  • May 01, 2025

  Last Listing Agent Laura King MarketPlace REALTY
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  /58

  $299,900

  • 2 Beds
  • 2 Baths
  • 1,227 Sq Ft

  510 N Pleasant Valley Rd, Winchester, VA 22601

  New Price! Welcome to 510 N Pleasant Valley Rd. Well-maintained home - Roof-2019 / Copper Plumbing 2010 / Electrical Panel 2024 / HVAC 2026 / Gas FP 2013 / Hot Water Heater 2022 / Windows 2004 / Sewer Line 2013 - many updates completed. Home offering comfort, convenience, and lifestyle appeal in the heart of Winchester. This home features 2 spacious bedrooms and 2 full bathrooms, features a

  RoxAnn Grimes RE/MAX Roots

  510 N Pleasant Valley Rd, Winchester, VA 22601
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  /9

  $1,300

  Total Monthly Price

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

  1114 Allen Dr, Winchester, VA 22601

  Discover the ultimate convenience at 1114 Allen Dr., a place that truly has it all, WATER INCLUDED. This exceptional downstairs apartment offers a prime location just minutes away from Rt. 7 and 81, with downtown and Shenandoah University equally nearby. Hardwood floors throughout and an abundance of natural light create an inviting and cozy atmosphere that will make you feel right at home. With

  1114 Allen Dr, Winchester, VA 22601
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  /19

  $226,000 Sold Jul 03, 2025

  521 1/2 N Loudoun St, Winchester, VA 22601

  • 4 Beds
  • 1.5 Baths
  • 1,277 Sq Ft
  • Built 1936

  Last Sold Summary

  • $177/SF
  • 6 Days On Market

  Current Estimated Value $276,613

  Last Listing Agent Barton Chasler Realty ONE Group Old Towne

  521 1/2 N Loudoun St, Winchester, VA 22601
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  /8

  Est $250,632 Not Listed For Sale

  521 Monticello St, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft
  • Built 1981

  521 Monticello St, Winchester, VA 22601

  Last Sold Summary

  • 19% Above List Price
  • $197/SF
  • 4 Days On Market

  • Last Sold Price $210,000
  • May 10, 2024

  Last Listing Agent Ned Stock BHHS PenFed (actual)
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  /30

  $375,000 Coming Soon

  • 4 Beds
  • 3 Baths
  • 1,916 Sq Ft

  317 N Kent St, Winchester, VA 22601

  An amazing totally renovated 1820 home in the heart of downtown/historic district!! This home features: 4bedrooms, 3 full baths, remodeled gourmet kitchen, refinished hardwood floors, barn style doors, deluxeprimary bath, and so much more.

  Clark Smith Samson Properties

  317 N Kent St, Winchester, VA 22601
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  /20

  $2,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,626 Sq Ft
  • House for Rent

  30 N Euclid Ave, Winchester, VA 22601

  COMMUTER CONVENIENT AND MOVE-IN READY. WHY RENT A TOWNHOUSE WHEN YOU CAN LIVE IN THIS BEAUTIFUL, SPACIOUS SINGLE-FAMILY HOME! In-town convenience. Near downtown, I-81, and Routes 7 and 50. Spacious 3-BR Colonial with open floor plan, large rooms. Hardwood floors main level. Open floor plan. Great room with gas log fireplace. Primary bedroom with vaulted ceiling and private bathroom. One-car

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  30 N Euclid Ave, Winchester, VA 22601
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  /35

  $334,900 Sold Nov 25, 2025

  2225 Harrison St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1955

  Last Sold Summary

  • $258/SF
  • 42 Days On Market

  Current Estimated Value $331,824

  Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.

  2225 Harrison St, Winchester, VA 22601
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  /22

  Est $255,806 Not Listed For Sale

  514 Armour Dale, Winchester, VA 22601

  • 2 Beds
  • 1 Bath
  • 765 Sq Ft
  • Built 1955

  514 Armour Dale, Winchester, VA 22601

  Last Sold Summary

  • 3% Above List Price
  • $325/SF
  • 4 Days On Market

  • Last Sold Price $249,000
  • Oct 31, 2024

  Last Listing Agent Katy Kidwell Burch Real Estate Group, LLC
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  /10

  $449,000

  • Land
  • 3,920 Sq Ft
  • $4,988,889 per Acre

  1 N Braddock St, Winchester, VA 22601

  Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

  Gillian Greenfield Coldwell Banker Premier

  1 N Braddock St, Winchester, VA 22601
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  /32

  $1,425

  Total Monthly Price

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

  2555 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

  2555 Bradford Ct, Winchester, VA 22601
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  /28

  $287,000 Sold Aug 05, 2025

  946 Franklin St, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft
  • Built 1955

  Last Sold Summary

  • $199/SF
  • 34 Days On Market

  Current Estimated Value $282,836

  Last Listing Agent Stan Dull The Wiley Companies, Inc.

  946 Franklin St, Winchester, VA 22601
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  /71

  Est $352,254 Not Listed For Sale

  517 Armour Dale, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 1,600 Sq Ft
  • Built 1935

  517 Armour Dale, Winchester, VA 22601

  Last Sold Summary

  • 12% Below List Price
  • $250/SF
  • 3 Days On Market

  • Last Sold Price $400,000
  • Jun 14, 2024

  Last Listing Agent John Ashton Equity Realty
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  /45

  $465,000

  • 3 Beds
  • 2.5 Baths
  • 2,293 Sq Ft

  3137 Eton Place, Winchester, VA 22601

  Welcome to The Lofts at Creekside! Better than new and absolutely breathtaking, this four-level interior townhome delivers style, space, and an unbeatable lifestyle—all within walking distance to top-rated restaurants, shopping, and the historic Kernstown Battlefield. Offering 3 bedrooms and 2.5 baths, the home features a chic upper-level loft that opens to a stunning private terrace, perfect for

  Laura White ERA Oakcrest Realty, Inc.

  3137 Eton Place, Winchester, VA 22601
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  /17

  $1,545 Per Month

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

  609 Smithfield Ave, Winchester, VA 22601

  For Lease – Available Immediately! Don’t miss this charming three-level end-unit townhouse, ideally located just minutes from downtown Winchester and Shenandoah University. Enjoy convenient access to shopping, dining, schools, recreational activities, and major commuter routes.This well-maintained home features two spacious bedrooms and one full bath, along with beautiful hardwood floors that

  Tracy Jewell Samson Properties

  609 Smithfield Ave, Winchester, VA 22601
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  /66

  $685,000 Sold Oct 29, 2025

  2530 Goldenfield Ln, Winchester, VA 22601

  • 4 Beds
  • 5 Baths
  • 5,903 Sq Ft
  • Built 2005

  Last Sold Summary

  • $116/SF
  • 21 Days On Market

  Current Estimated Value $708,249

  Last Listing Agent Dave Spence RE/MAX Roots

  2530 Goldenfield Ln, Winchester, VA 22601
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  /46

  Est $525,173 Not Listed For Sale

  605 Kernstown Ct, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,568 Sq Ft
  • Built 1997

  605 Kernstown Ct, Winchester, VA 22601

  Last Sold Summary

  • 8% Above List Price
  • $189/SF
  • 14 Days On Market

  • Last Sold Price $485,000
  • Jul 19, 2024

  Last Listing Agent Omar Gonzalez Real Living at Home
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  /10

  $273,000

  • 2 Beds
  • 2.5 Baths
  • 1,280 Sq Ft

  2967 Sorrell Ct, Winchester, VA 22601

  This diamond in the rough has solid bones and plenty of potential for the right buyer. The HVAC system is only two years old, the water heater is brand new, and both full bathrooms have already been updated. The home could use some fresh paint, and the dishwasher is currently not working, but the major systems are in great shape—making this an excellent opportunity for a starter home or

  Jamie Cook Treck Realty LLC

  2967 Sorrell Ct, Winchester, VA 22601
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  /21

  $1,300 Per Month

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

  105 N Loudoun St Unit 3, Winchester, VA 22601

  Welcome home to 105 N Loudoun St. This is the apartment you've been searching for! This fantastic second floor apartment is above the Village Square restaurant, on the walking mall. This unit has so much charm and character, look at those builtins. Minutes to Shenandoah University. Includes 1 assigned parking spot downtown! Shared washer and dryer a few steps from your door step. Water, Sewer,

  Chris Roszko Colony Realty

  105 N Loudoun St Unit 3, Winchester, VA 22601
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  /51

  $450,000 Sold Nov 21, 2025

  609 Crystal Ct, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,868 Sq Ft
  • Built 1990

  Last Sold Summary

  • $157/SF
  • 31 Days On Market

  Current Estimated Value $451,619

  Last Listing Agent Tiffany Hunter ERA Oakcrest Realty, Inc.

  609 Crystal Ct, Winchester, VA 22601
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  /38

  Est $508,291 Not Listed For Sale

  3022 Saratoga Dr, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft
  • Built 2000

  3022 Saratoga Dr, Winchester, VA 22601

  Last Sold Summary

  • 4% Above List Price
  • $212/SF
  • 42 Days On Market

  • Last Sold Price $489,000
  • Jul 29, 2024

  Last Listing Agent Brett Sowder RE/MAX

Showing Results 241 - 280, Page 7 of 18