Winchester, VA Homes

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  /3

  $445,000

  • 6 Beds
  • 3 Baths
  • 1,917 Sq Ft

  623 Smithfield Ave, Winchester, VA 22601

  Spacious split-foyer home in the heart of Winchester featuring 6 bedrooms and 3 full bathrooms, plus a versatile bonus room in the basement ideal for a variety of uses. Well-maintained and located in a convenient neighborhood with no HOA.

  

  Carlos Soares

  Samson Properties

  (540) 253-3199

  623 Smithfield Ave, Winchester, VA 22601
• Explore Winchester

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  /9

  $1,700 per month

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  15 S Braddock St, Winchester, VA 22601

  Updated one bedroom, one bath apartment behind office building in Downtown Winchester. Includes off street parking and laundry. Tenant pays internet/cable. No pets, no smoking, and credit score of 650 or above is required.

  

  Frank Armstrong, IV

  Colony Realty

  (540) 277-9890

  15 S Braddock St, Winchester, VA 22601
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  $190,000 Sold Nov 25, 2025

  303 Barrington Ln, Winchester, VA 22601

  • 2 Beds
  • 1 Bath
  • 894 Sq Ft
  • Built 1994

  Last Sold Summary

  • $213/SF
  • 86 Days On Market

  Current Estimated Value $203,436

  Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.

  303 Barrington Ln, Winchester, VA 22601
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  Not Listed For Sale

  903 Rockwood Trail, Winchester, VA 22602

  • 3 Beds
  • 2 Baths
  • 1,474 Sq Ft
  • Built 2024

  903 Rockwood Trail, Winchester, VA 22602

  Last Sold Summary

  • $237/SF
  • 177 Days On Market

  • Last Sold Price $350,000
  • Apr 25, 2025

  Last Listing Agent Amber Jenkins Century 21 Redwood Realty
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  /46

  $489,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,698 Sq Ft

  312 W Cecil St, Winchester, VA 22601

  Don’t miss your chance to live on sought-after W. Cecil in this charming, beautifully maintained historic home, just a few blocks from the walking mall. Light-filled and inviting, this home welcomes you with a classic covered front porch and warm hardwood floors that set the tone for the character throughout. The cozy living room features a recently converted gas fireplace, lovely built-ins, and

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 405-6463

  312 W Cecil St, Winchester, VA 22601
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  /16

  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 2,326 Sq Ft
  • House for Rent

  131 Obriens Cir, Winchester, VA 22602

  Available April 1st. Charming ranch style home offers 3-bedrooms, 2 full baths, lower level family room and a fenced yard conveniently located close to I81, Restaurants and Shopping. Perfect commuter location. Spacious living room with hardwood floors, fully equipped eat-in kitchen features peninsula counter with bar stool seating, large dining area with direct access to wood deck; primary

  

  Ken Smith

  Sager Real Estate

  (540) 755-3853

  131 Obriens Cir, Winchester, VA 22602
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  /57

  $625,000 Sold Oct 31, 2025

  101 Arthur Ln, Winchester, VA 22602

  • 5 Beds
  • 3.5 Baths
  • 4,787 Sq Ft
  • Built 2007

  Last Sold Summary

  • $131/SF
  • 5 Days On Market

  Current Estimated Value $642,375

  Last Listing Agent Scotti Sellers Compass

  101 Arthur Ln, Winchester, VA 22602
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  /65

  Est $419,066 Not Listed For Sale

  205 Cobble Stone Dr, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 2,263 Sq Ft
  • Built 2014

  205 Cobble Stone Dr, Winchester, VA 22602

  Last Sold Summary

  • 6% Above List Price
  • $175/SF
  • 6 Days On Market

  • Last Sold Price $397,000
  • Mar 27, 2025

  Last Listing Agent Jeffrey Konrady Realty ONE Group Old Towne
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  /30

  $285,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  704 Watson Ave, Winchester, VA 22601

  Beautifully Maintained Bungalow in a Prime Location! SELLER MOTIVATED! This home offers 2 bedrooms and 1 full bath on the main level, showcasing pride of ownership throughout. Ideally located just blocks from shopping, coffee shops, and all the conveniences the city has to offer, this property combines comfort with unbeatable accessibility. Enjoy a spacious eat-in kitchen with plenty of room for

  

  Carlos Soares

  Samson Properties

  (540) 530-4023

  704 Watson Ave, Winchester, VA 22601
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  /13

  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  21 S Stewart St Unit 2, Winchester, VA 22601

  2 Bedroom Apartment for Rent – Downtown Winchester Great 2nd-floor apartment located in downtown Winchester with 2 bedrooms and 1 bathroom. This home is just a short walk from Old Town Winchester, giving you easy access to local restaurants, shops, and entertainment. The apartment features very spacious bedrooms, a comfortable family room, and a fully enclosed back porch, perfect for relaxing or

  

  Frank Armstrong, IV

  Colony Realty

  (540) 534-4239

  21 S Stewart St Unit 2, Winchester, VA 22601
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  /31

  $280,000 Sold May 08, 2025

  151 4 Brookland Terrace, Winchester, VA 22602

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Built 1998

  Last Sold Summary

  • $239/SF
  • 267 Days On Market

  Current Estimated Value $275,803

  Last Listing Agent Melissa Davis RE/MAX Distinctive Real Estate, Inc.

  151 4 Brookland Terrace, Winchester, VA 22602
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  Est $441,236 Not Listed For Sale

  222 E Piccadilly St, Winchester, VA 22601

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

  222 E Piccadilly St, Winchester, VA 22601

  Last Sold Summary

  • 9% Above List Price
  • $197/SF
  • 595 Days On Market

  • Last Sold Price $404,900
  • May 15, 2024

  Last Listing Agent Jason Aikens RE/MAX
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  $1,499,000

  • Land
  • 2.45 Acres
  • $611,837 per Acre

  821,829,839, and 851 Fox Dr, Winchester, VA 22603

  Location Location Location! 2.45 Acres comprised of 4 Lots with 3 income producing dwellings. Site falls withing the Frederick County Comprehensive Plan for Commercial Uses. Located just off the Route 37 and Route 522 Interchange next to Sheetz and KFC. All Dwellings and Outbuildings are strictly as-is.

  

  Jim Shebest

  Coldwell Banker Realty

  (540) 530-3068

  821,829,839, and 851 Fox Dr, Winchester, VA 22603
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  $2,300 per month

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

  151 Munsee Cir, Winchester, VA 22602

  4 bedroom Smart Home Available in MAY Welcome home to the Retreat at Winding Creek community. This almost new townhome offers the perfect blend of modern living and convenient location. The entry level features a spacious 4th bedroom/rec room with a full ensuite bath, ideal for guests or a home office. The main level boasts a dramatic open floor plan, perfect for entertaining. Enjoy a

  

  Abby Ghanta

  Samson Properties

  (540) 625-1820

  151 Munsee Cir, Winchester, VA 22602
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  $529,000 Sold May 14, 2025

  113 Old Wagon Rd, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 2,828 Sq Ft
  • Built 1999

  Last Sold Summary

  • $187/SF
  • 10 Days On Market

  Current Estimated Value $535,621

  Last Listing Agent Kimberly Pace EXP Realty, LLC

  113 Old Wagon Rd, Winchester, VA 22602
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  Not Listed For Sale

  0 Susquehanna Trail, Winchester, VA 22602

  0 Susquehanna Trail, Winchester, VA 22602

  Last Sold Summary

  • 19 Days On Market

  • Last Sold Price $20,500
  • Nov 22, 2023

  Last Listing Agent Jacob Taylor Blue Valley Real Estate
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  $349,900 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,890 Sq Ft

  113 Christopher Dr, Winchester, VA 22601

  Meticulously maintained 3 bedroom, 1.5 bath home in a convenient in-town Winchester location! This home shows beautifully and features hardwood floors that add warmth and character throughout the main living areas. Spacious bedrooms and updates made over the years make this home functional and livable, while still providing an opportunity to personalize as desired. The partially finished basement

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 318-0527

  113 Christopher Dr, Winchester, VA 22601
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  $1,350 per month

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

  233 Kern St, Winchester, VA 22601

  Downtown Winchester location, full of light and super cute! This 2 bed/1 bath duplex offers a private, fenced in backyard on the north side of town. Completely renovated in 2022. Available for immediate occupancy. Application fee $50 for everyone 18 or older, no pets, monthly income minimum of 3x the monthly rent, security deposit is $1350, no previous evictions, credit score 620+, landlord pays

  

  Anna Fox

  NextHome Realty Select

  (540) 299-2935

  233 Kern St, Winchester, VA 22601
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  $595,000 Sold Aug 08, 2025

  121 Carnmore Dr, Winchester, VA 22602

  • 5 Beds
  • 4 Baths
  • 3,086 Sq Ft
  • Built 2005

  Last Sold Summary

  • $193/SF
  • 103 Days On Market

  Current Estimated Value $611,482

  Last Listing Agent Angela Duncan MarketPlace REALTY

  121 Carnmore Dr, Winchester, VA 22602
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  /20

  Est $436,245 Not Listed For Sale

  206 N Kent St, Winchester, VA 22601

  • 2 Beds
  • 4 Baths
  • 2,160 Sq Ft
  • Built 2022

  206 N Kent St, Winchester, VA 22601

  Last Sold Summary

  • 4% Below List Price
  • $211/SF
  • 0 Days On Market

  • Last Sold Price $455,400
  • Sep 29, 2023

  Last Listing Agent Jason Aikens RE/MAX
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  /40

  $640,000 Under Contract

  • 6 Beds
  • 3.5 Baths
  • 3,192 Sq Ft

  162 Omps Dr, Winchester, VA 22601

  This exceptional residence is nestled in a popular neighborhood in Winchester, just moments from Winchester Medical Center. With almost 4,000 square feet of refined living space, this 6-bedroom, 3.5-bath home delivers the scale, comfort, and location today’s discerning buyer expects.Designed for both elegant entertaining and everyday ease, the home features expansive living areas filled with

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 274-1014

  162 Omps Dr, Winchester, VA 22601
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  /11

  $1,400 per month

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

  44 S Loudoun St Unit 9, Winchester, VA 22601

  Charming 1 bedroom, 1 bathroom apartment located on the Historic Downtown walking mall, with access to all of the Shops, restaurants, museums, and more right out the front door! Just minutes from Shenandoah University, Apple Blossom Mall, and Winchester Medical Center. Parking for each unit.

  

  Brock Harris

  Samson Properties

  (540) 516-4753

  44 S Loudoun St Unit 9, Winchester, VA 22601
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  $644,990 Sold Sep 04, 2025

  126 Wagtail Ln, Winchester, VA 22603

  • 3 Beds
  • 2 Baths
  • 3,122 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $207/SF
  • 0 Days On Market

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

  126 Wagtail Ln, Winchester, VA 22603
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  /43

  Est $624,104 Not Listed For Sale

  405 Lynnehaven Dr, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 3,729 Sq Ft
  • Built 2012

  405 Lynnehaven Dr, Winchester, VA 22602

  Last Sold Summary

  • 6% Above List Price
  • $158/SF
  • 183 Days On Market

  • Last Sold Price $590,000
  • Jan 11, 2024

  Last Listing Agent John Orefice Samson Properties
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  /11

  $61,900

  • Land
  • 30,056 Sq Ft
  • $89,710 per Acre

  Lots 14 & 15 Glen Ridge Rd, Winchester, VA 22602

  Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 712-6303

  Lots 14 & 15 Glen Ridge Rd, Winchester, VA 22602
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  $2,200 per month

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Condo for Rent

  104 S Loudoun St Unit 2, Winchester, VA 22601

  Charming downtown living at it s best! Perfectly located directly on the Historic Downtown Walking Mall. This spacious 2 bedroom 2 bathroom condo features very own washer and dryer, stainless steel appliances, 2 assigned parking spots, HVAC and more. Shops, restaurants, museums, and more only steps from your front door. Check out convenient chic living today!

  

  Brock Harris

  Samson Properties

  (540) 596-5993

  104 S Loudoun St Unit 2, Winchester, VA 22601
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  /15

  $509,990 Sold Mar 11, 2026

  108 Carnation Way, Winchester, VA 22603

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $249/SF
  • 9 Days On Market

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

  108 Carnation Way, Winchester, VA 22603
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  /60

  Est $418,699 Not Listed For Sale

  152 Solara Dr, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 2,300 Sq Ft
  • Built 2017

  152 Solara Dr, Winchester, VA 22602

  Last Sold Summary

  • 5% Above List Price
  • $174/SF
  • 0 Days On Market

  • Last Sold Price $400,000
  • Jun 30, 2023

  Last Listing Agent Deborah Matthews ERA Oakcrest Realty, Inc.
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  /11

  $51,900

  • Land
  • 14,810 Sq Ft
  • $152,647 per Acre

  Lot 10 Glen Ridge Rd, Winchester, VA 22602

  Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 732-7734

  Lot 10 Glen Ridge Rd, Winchester, VA 22602
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  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • House for Rent

  228 Opequon Ave, Winchester, VA 22601

  coming soon- pictures will be up later today

  

  Frank Armstrong, IV

  Colony Realty

  (540) 766-5892

  228 Opequon Ave, Winchester, VA 22601
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  $415,000 Sold May 08, 2025

  526 N Braddock St, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,375 Sq Ft
  • Built 1927

  Last Sold Summary

  • $175/SF
  • 5 Days On Market

  Current Estimated Value $434,654

  Last Listing Agent Leah Clowser RE/MAX Roots

  526 N Braddock St, Winchester, VA 22601
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  Est $293,046 Not Listed For Sale

  201 Fawn Dr, Winchester, VA 22602

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 2014

  201 Fawn Dr, Winchester, VA 22602

  Last Sold Summary

  • 1% Below List Price
  • $267/SF
  • 43 Days On Market

  • Last Sold Price $295,000
  • Nov 20, 2024

  Last Listing Agent Jodi McCallister BHHS PenFed (actual)
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  $389,900

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft

  151 Mccormick Cir Unit 201, Winchester, VA 22602

  Price improvement!! Experience Effortless 55+ Living at Winchester Landing – The Sapphire by Ryan Homes Discover the perfect blend of comfort and convenience in the Sapphire model, a spacious single-level condo offering over 1,500 sq. ft. of thoughtfully designed living space. The open-concept layout seamlessly connects a modern kitchen, large island, and bright great room, creating an inviting

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  (540) 787-2320

  151 Mccormick Cir Unit 201, Winchester, VA 22602
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  $2,400 per month

  • 4 Beds
  • 3.5 Baths
  • 1,960 Sq Ft
  • Townhouse for Rent

  1801 Harvest Dr, Winchester, VA 22601

  Brand new and move-in ready, this attractive three-level end-unit townhome at 1801 Harvest Drive offers modern living in a fantastic Winchester location. Featuring a full brick front and additional sound insulation, this end unit provides both style and comfort. The entry level includes a one-car garage, a private bedroom, and a full bathroom, perfect for guests, a home office, or flexible living

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 619-5461

  1801 Harvest Dr, Winchester, VA 22601
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  /11

  $272,900 Sold Nov 13, 2025

  852 Butler Ave, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,010 Sq Ft
  • Built 1994

  Last Sold Summary

  • $270/SF
  • 5 Days On Market

  Current Estimated Value $285,132

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

  852 Butler Ave, Winchester, VA 22601
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  Est $1,790,122 Not Listed For Sale

  210 Rubinette Way, Winchester, VA 22602

  • 4 Beds
  • 5.5 Baths
  • 7,773 Sq Ft
  • Built 2004

  210 Rubinette Way, Winchester, VA 22602

  Last Sold Summary

  • 2% Above List Price
  • $225/SF
  • 92 Days On Market

  • Last Sold Price $1,750,000
  • Oct 11, 2024

  Last Listing Agent Julie Teets ERA Oakcrest Realty, Inc.
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  $644,900 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,490 Sq Ft

  128 Poe Dr, Winchester, VA 22602

  128 Poe Drive presents one of the largest models offered in the neighborhood, ideally positioned on a desirable corner lot with an expansive side yard in addition to the backyard. Built in 2023 and filled with upgrades, get ready to see one of the best homes in Winchester. Offering over 3,500 square feet with 4 bedrooms plus loft upstairs, including a finished basement, this home provides

  

  MJ Frazier

  Serhant

  (540) 515-5588

  128 Poe Dr, Winchester, VA 22602
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  $2,200 per month

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  21 S Stewart St Unit 4, Winchester, VA 22601

  Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester!Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard—ideal for relaxing or entertaining. You'll also love the generous storage

  

  Frank Armstrong, IV

  Colony Realty

  (540) 318-1292

  21 S Stewart St Unit 4, Winchester, VA 22601
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  $307,000 Sold Mar 26, 2026

  140 Mccormick Cir Unit 302, Winchester, VA 22602

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $266/SF
  • 71 Days On Market

  Last Listing Agent Karl Achstetter Keller Williams Realty

  140 Mccormick Cir Unit 302, Winchester, VA 22602
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  Est $917,804 Not Listed For Sale

  420 N Hayfield Rd, Winchester, VA 22603

  • 4 Beds
  • 5 Baths
  • 4,632 Sq Ft
  • Built 1985

  420 N Hayfield Rd, Winchester, VA 22603

  Last Sold Summary

  • 15% Above List Price
  • $172/SF
  • 21 Days On Market

  • Last Sold Price $799,000
  • Oct 20, 2023

  Last Listing Agent Dan Whitacre Colony Realty

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