5,504

Stephenson, VA Homes

Section Image
  • 219 Shenandoah Trail, Winchester, VA 22602
    219 Shenandoah Trail, Winchester, VA 22602
    219 Shenandoah Trail, Winchester, VA 22602
    /30

    $360,000

    Sold Feb 04, 2026

    219 Shenandoah Trail, Winchester, VA 22602

    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft
    • Built 2025

    Last Sold Summary

    • $217/SF
    • 326 Days On Market

    Last Listing Agent Jim Thomson Realty ONE Group Old Towne

    219 Shenandoah Trail, Winchester, VA 22602
    • 127 Arrowhead Trail, Winchester, VA 22602
      127 Arrowhead Trail, Winchester, VA 22602
      127 Arrowhead Trail, Winchester, VA 22602
      /36

      Est $288,647

      Not Listed For Sale

      127 Arrowhead Trail, Winchester, VA 22602

      • 2 Beds
      • 1 Bath
      • 1,296 Sq Ft
      • Built 1994
      127 Arrowhead Trail, Winchester, VA 22602

      Last Sold Summary

      • 30 Days On Market

  • Lot 7 Oak, Winchester, VA 22603
    Lot 7 Oak, Winchester, VA 22603
    /2

    $199,900

    $50K PRICE DROP
    • Land
    • 5.01 Acres
    • $39,900 per Acre

    Lot 7 Oak, Winchester, VA 22603

    Build Your Vision at the End of the LaneDiscover a rare opportunity to create a custom estate in an established community of luxury homes (up to 4,000 sq. ft.). Located at the quiet end of the street, this lot offers the perfect blend of privacy and prestige. Enjoy the peace of a secluded setting without sacrificing convenience—you are minutes from town with effortless access to Route 50.

    Jim Thomson Realty ONE Group Old Towne

    Lot 7 Oak, Winchester, VA 22603
  • 129 Indiana Trail, Winchester, VA 22602
    129 Indiana Trail, Winchester, VA 22602
    129 Indiana Trail, Winchester, VA 22602
    /26

    $385,000

    Sold Mar 27, 2026

    129 Indiana Trail, Winchester, VA 22602

    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft
    • Built 2025

    Last Sold Summary

    • $232/SF
    • 136 Days On Market

    Last Listing Agent Jim Thomson Realty ONE Group Old Towne

    129 Indiana Trail, Winchester, VA 22602
    • 292 Marple Rd, Winchester, VA 22603
      292 Marple Rd, Winchester, VA 22603
      292 Marple Rd, Winchester, VA 22603
      /28

      Est $397,143

      Not Listed For Sale

      292 Marple Rd, Winchester, VA 22603

      • 3 Beds
      • 2 Baths
      • 1,633 Sq Ft
      • Built 1965
      292 Marple Rd, Winchester, VA 22603

      Last Sold Summary

      • 1 Day On Market

  • 121 Cherokee Trail, Winchester, VA 22602
    121 Cherokee Trail, Winchester, VA 22602
    121 Cherokee Trail, Winchester, VA 22602
    /70

    $474,500

    • 3 Beds
    • 3.5 Baths
    • 2,650 Sq Ft

    121 Cherokee Trail, Winchester, VA 22602

    Lake and mountain views, a private in-ground pool, and an adjoining .63-acre lot — this beautifully updated Shawneeland home sits on .37 acres and conveys with an additional .63 acre of record (Tax Map ID #49A031A13A), for approximately 1 acre of mountain privacy. Filled with natural light, the home features hardwood floors, fireplaces throughout, and a renovated kitchen with quartz countertops,

    Sebastian Langenberg Corcoran McEnearney

    121 Cherokee Trail, Winchester, VA 22602
  • 237 Aspen Trail, Winchester, VA 22602
    237 Aspen Trail, Winchester, VA 22602
    237 Aspen Trail, Winchester, VA 22602
    /69

    $675,000

    Sold Jun 27, 2025

    237 Aspen Trail, Winchester, VA 22602

    • 3 Beds
    • 3.5 Baths
    • 3,432 Sq Ft
    • Built 2001

    Last Sold Summary

    • $197/SF
    • 15 Days On Market

    Current Estimated Value $710,446

    Last Listing Agent Sheila Pack RE/MAX Roots

    237 Aspen Trail, Winchester, VA 22602
    • 179 Cedar Grove Rd, Winchester, VA 22603
      179 Cedar Grove Rd, Winchester, VA 22603
      179 Cedar Grove Rd, Winchester, VA 22603
      /29

      Est $105,586

      Not Listed For Sale

      179 Cedar Grove Rd, Winchester, VA 22603

      • Built 1961
      179 Cedar Grove Rd, Winchester, VA 22603

      Last Sold Summary

      • 149 Days On Market

  • 235 Peppermint Spring Ln, Winchester, VA 22603
    235 Peppermint Spring Ln, Winchester, VA 22603
    235 Peppermint Spring Ln, Winchester, VA 22603
    /90

    $485,000

    $32K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 1,962 Sq Ft

    235 Peppermint Spring Ln, Winchester, VA 22603

    Discover Your Private Retreat: 235 Peppermint Spring LaneNestled in the serene landscape of Winchester, Virginia, 235 Peppermint Spring Lane offers a rare combination of spacious country living and modern convenience. This charming single-family home sits on a sprawling 6.67-acre lot, providing a peaceful sanctuary backing to conservation land just minutes from the vibrant energy of historic

    Andrew Hensley Samson Properties

    235 Peppermint Spring Ln, Winchester, VA 22603
  • 261 Middle Ln, Gore, VA 22637
    261 Middle Ln, Gore, VA 22637
    261 Middle Ln, Gore, VA 22637
    /39

    $225,000

    Sold Oct 17, 2025

    261 Middle Ln, Gore, VA 22637

    • 3 Beds
    • 1 Bath
    • 1,004 Sq Ft
    • Built 1950

    Last Sold Summary

    • $224/SF
    • 29 Days On Market

    Current Estimated Value $230,052

    Last Listing Agent Jaime Pinto Funkhouser Real Estate Group

    261 Middle Ln, Gore, VA 22637
    • 150 Marple Rd, Winchester, VA 22603
      150 Marple Rd, Winchester, VA 22603
      150 Marple Rd, Winchester, VA 22603
      /28

      Est $314,680

      Not Listed For Sale

      150 Marple Rd, Winchester, VA 22603

      • 2 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1955
      150 Marple Rd, Winchester, VA 22603

      Last Sold Summary

      • 7 Days On Market

  • 200 Middle Ln, Gore, VA 22637
    200 Middle Ln, Gore, VA 22637
    200 Middle Ln, Gore, VA 22637
    /5

    $250,000

    • 2 Beds
    • 1 Bath
    • 989 Sq Ft

    200 Middle Ln, Gore, VA 22637

    Tucked away on a quiet lane in the Gore countryside, this cozy 2-bedroom, 1-bath cottage offers an affordable entry point into homeownership or a smart addition to any investment portfolio. Built in 1964 and full of classic character, the home features hardwood floors, a metal roof, and a covered porch that invites you to slow down and take in the peaceful surroundings.The 0.37-acre lot

    Shane Bowman RE/MAX Roots

    200 Middle Ln, Gore, VA 22637
  • 113 Deer Trail, Winchester, VA 22602
    113 Deer Trail, Winchester, VA 22602
    113 Deer Trail, Winchester, VA 22602
    /28

    $370,000

    Sold Jun 05, 2026

    113 Deer Trail, Winchester, VA 22602

    • 3 Beds
    • 2 Baths
    • 1,592 Sq Ft
    • Built 1960

    Last Sold Summary

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

    Current Estimated Value $361,176

    Last Listing Agent Caleb Fowler Samson Properties

    113 Deer Trail, Winchester, VA 22602
    • 128 Dunbar Ln, Winchester, VA 22603
      128 Dunbar Ln, Winchester, VA 22603
      128 Dunbar Ln, Winchester, VA 22603
      /45

      Est $332,749

      Not Listed For Sale

      128 Dunbar Ln, Winchester, VA 22603

      • 3 Beds
      • 2 Baths
      • 1,863 Sq Ft
      • Built 1950
      128 Dunbar Ln, Winchester, VA 22603

      Last Sold Summary

      • 5 Days On Market

  • 110 Erie Trail, Winchester, VA 22602
    110 Erie Trail, Winchester, VA 22602
    110 Erie Trail, Winchester, VA 22602
    /61

    $299,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,698 Sq Ft

    110 Erie Trail, Winchester, VA 22602

    Welcome home to your own little slice of peace in the mountains of Winchester. Tucked into the scenic Shawneeland community, 110 Erie Trail offers the kind of charm and privacy that first-time buyers dream about — without sacrificing affordability or convenience.Imagine starting your mornings with coffee surrounded by trees instead of traffic, spending evenings under the stars, and finally

    Katrina Smith Samson Properties

    110 Erie Trail, Winchester, VA 22602
  • 110 Red Fox Trail, Winchester, VA 22602
    110 Red Fox Trail, Winchester, VA 22602
    110 Red Fox Trail, Winchester, VA 22602
    /29

    $275,000

    Sold Jun 11, 2026

    110 Red Fox Trail, Winchester, VA 22602

    • 3 Beds
    • 1.5 Baths
    • 1,230 Sq Ft
    • Built 1971

    Last Sold Summary

    • $224/SF
    • 15 Days On Market

    Current Estimated Value $267,752

    Last Listing Agent Angie Ordonez NextHome Realty Select

    110 Red Fox Trail, Winchester, VA 22602
    • 108 Dunbar Ln, Winchester, VA 22603
      108 Dunbar Ln, Winchester, VA 22603
      108 Dunbar Ln, Winchester, VA 22603
      /33

      Est $333,192

      Not Listed For Sale

      108 Dunbar Ln, Winchester, VA 22603

      • 3 Beds
      • 2.5 Baths
      • 1,450 Sq Ft
      • Built 1961
      108 Dunbar Ln, Winchester, VA 22603

      Last Sold Summary

      • 4 Days On Market

  • 112 Cornstalk Trail, Winchester, VA 22602
    112 Cornstalk Trail, Winchester, VA 22602
    112 Cornstalk Trail, Winchester, VA 22602
    /48

    $380,000

    • 3 Beds
    • 3 Baths
    • 1,276 Sq Ft

    112 Cornstalk Trail, Winchester, VA 22602

    COME TO THE COUNTRY! WELCOME TO THE GOOD LIFE IN THIS RUSTIC MOUNTAIN-LAKE COMMUNITY WITH A BEACH. A short drive to downtown, Winchester Medical Center, restaurants, shopping and services. Lovely and affordable split foyer with 3 bedrooms, 3 full baths, a finished basement and a 2-car garage. Open floor plan. Large living room with vaulted ceiling. Kitchen with breakfast bar, newer stainless

    Teresa Strohmeyer ERA Oakcrest Realty, Inc.

    112 Cornstalk Trail, Winchester, VA 22602
  • 492 Chestnut Grove Rd, Winchester, VA 22603
    492 Chestnut Grove Rd, Winchester, VA 22603
    /2

    $619,000

    Sold May 14, 2026

    492 Chestnut Grove Rd, Winchester, VA 22603

    • 3 Beds
    • 2 Baths
    • 1,548 Sq Ft
    • Built 2005

    Last Sold Summary

    • 5% Below List Price
    • $400/SF

    Current Estimated Value $647,547

    Last Listing Agent Erika De Azagra ERA Oakcrest Realty, Inc.

    492 Chestnut Grove Rd, Winchester, VA 22603
    • 707 Old Bethel Church Rd, Winchester, VA 22603
      707 Old Bethel Church Rd, Winchester, VA 22603
      707 Old Bethel Church Rd, Winchester, VA 22603
      /36

      Est $542,633

      Not Listed For Sale

      707 Old Bethel Church Rd, Winchester, VA 22603

      • 4 Beds
      • 2.5 Baths
      • 2,373 Sq Ft
      • Built 1990
      707 Old Bethel Church Rd, Winchester, VA 22603

      Last Sold Summary

      • 15 Days On Market

  • LOT 115 Rockwood Trail, Back Creek, VA 22602
    LOT 115 Rockwood Trail, Back Creek, VA 22602
    LOT 115 Rockwood Trail, Back Creek, VA 22602
    /12

    $165,000

    • Land
    • 19,166 Sq Ft
    • $375,000 per Acre

    LOT 115 Rockwood Trail, Back Creek, VA 22602

    More Pictures On The Way! Now Offering This Beautiful Lot In Shawneeland VA, Just West Of Winchester! Mountain Top Lot With Great View! Lot Is Cleared, and Neighbors Lot Is Also! Clear View Of The Winchester City Area And Beyond!This .44 Acre Lot Has A Cleared Area With A Standing Shed, A 3 Bedroom Septic Perk, And Power Is Already Run On This Road. Mountain Top Living Includes The Frederick

    Tracy Link Coldwell Banker Premier

    LOT 115 Rockwood Trail, Back Creek, VA 22602
  • 133 Erie Trail, Winchester, VA 22602
    133 Erie Trail, Winchester, VA 22602
    133 Erie Trail, Winchester, VA 22602
    /58

    $346,600

    Sold May 06, 2026

    133 Erie Trail, Winchester, VA 22602

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1996

    Last Sold Summary

    • 5% Below List Price
    • $238/SF
    • 7 Days On Market

    Current Estimated Value $359,181

    Last Listing Agent Tracy Link Coldwell Banker Premier

    133 Erie Trail, Winchester, VA 22602
    • 1040 Dicks Hollow Rd, Winchester, VA 22603
      1040 Dicks Hollow Rd, Winchester, VA 22603
      1040 Dicks Hollow Rd, Winchester, VA 22603
      /29

      Est $333,797

      Not Listed For Sale

      1040 Dicks Hollow Rd, Winchester, VA 22603

      • 3 Beds
      • 1 Bath
      • 1,556 Sq Ft
      • Built 1954
      1040 Dicks Hollow Rd, Winchester, VA 22603

      Last Sold Summary

      • 4 Days On Market

  • 0 Hedrick Ln, Winchester, VA 22602
    0 Hedrick Ln, Winchester, VA 22602
    0 Hedrick Ln, Winchester, VA 22602
    /41

    $88,000

    Sold Jun 11, 2026

    0 Hedrick Ln, Winchester, VA 22602

    • Land
    • 5.1 Acres
    • $17,255 per Acre

    Last Sold Summary

    • 185 Days On Market

    Last Listing Agent Erik Thorpe ERA Valley Realty

    0 Hedrick Ln, Winchester, VA 22602
    • 675 Dicks Hollow Rd, Winchester, VA 22603
      675 Dicks Hollow Rd, Winchester, VA 22603
      675 Dicks Hollow Rd, Winchester, VA 22603
      /32

      Est $311,734

      Not Listed For Sale

      675 Dicks Hollow Rd, Winchester, VA 22603

      • 3 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1974
      675 Dicks Hollow Rd, Winchester, VA 22603

      Last Sold Summary

      • 5 Days On Market

  • 310 Wardensville Grade, Winchester, VA 22602
    310 Wardensville Grade, Winchester, VA 22602
    310 Wardensville Grade, Winchester, VA 22602
    /38

    $250,000

    Sold Nov 21, 2025

    310 Wardensville Grade, Winchester, VA 22602

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1998

    Last Sold Summary

    • $289/SF
    • 3 Days On Market

    Current Estimated Value $258,264

    Last Listing Agent Tracy Link Coldwell Banker Premier

    310 Wardensville Grade, Winchester, VA 22602
    • 1077 Dicks Hollow Rd, Winchester, VA 22603
      1077 Dicks Hollow Rd, Winchester, VA 22603
      1077 Dicks Hollow Rd, Winchester, VA 22603
      /26

      Est $428,622

      Not Listed For Sale

      1077 Dicks Hollow Rd, Winchester, VA 22603

      • 3 Beds
      • 2 Baths
      • 1,662 Sq Ft
      • Built 1993
      1077 Dicks Hollow Rd, Winchester, VA 22603

      Last Sold Summary

      • 117 Days On Market

  • 110 Braveheart Trail, Winchester, VA 22602
    110 Braveheart Trail, Winchester, VA 22602
    110 Braveheart Trail, Winchester, VA 22602
    /61

    $469,900

    Sold Jun 27, 2025

    110 Braveheart Trail, Winchester, VA 22602

    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft
    • Built 2000

    Last Sold Summary

    • $329/SF
    • 5 Days On Market

    Current Estimated Value $456,771

    Last Listing Agent Susan Raburn Long & Foster Real Estate, Inc.

    110 Braveheart Trail, Winchester, VA 22602
    • 1049 Dicks Hollow Rd, Winchester, VA 22603
      1049 Dicks Hollow Rd, Winchester, VA 22603
      1049 Dicks Hollow Rd, Winchester, VA 22603
      /23

      Est $385,951

      Not Listed For Sale

      1049 Dicks Hollow Rd, Winchester, VA 22603

      • 2 Beds
      • 3 Baths
      • 1,152 Sq Ft
      • Built 1983
      1049 Dicks Hollow Rd, Winchester, VA 22603

      Last Sold Summary

      • 76 Days On Market

  • 140 Doe Trail, Winchester, VA 22602
    140 Doe Trail, Winchester, VA 22602
    140 Doe Trail, Winchester, VA 22602
    /19

    $384,722

    Sold Nov 12, 2025

    140 Doe Trail, Winchester, VA 22602

    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft
    • Built 2025

    Last Sold Summary

    • $232/SF
    • 350 Days On Market

    Last Listing Agent Jim Thomson Realty ONE Group Old Towne

    140 Doe Trail, Winchester, VA 22602
    • 612 Marple Rd, Winchester, VA 22603
      612 Marple Rd, Winchester, VA 22603
      612 Marple Rd, Winchester, VA 22603
      /61

      Est $408,848

      Not Listed For Sale

      612 Marple Rd, Winchester, VA 22603

      • 2 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1981
      612 Marple Rd, Winchester, VA 22603

      Last Sold Summary

      • 2 Days On Market

  • Lot 152 Christie Ln, Whitacre, VA 22625
    Lot 152 Christie Ln, Whitacre, VA 22625
    Lot 152 Christie Ln, Whitacre, VA 22625
    /11

    $6,500

    Sold Jul 18, 2025

    Lot 152 Christie Ln, Whitacre, VA 22625

    • Land
    • 0 Sq Ft

    Last Sold Summary

    • 62 Days On Market

    Last Listing Agent Misty Weaver Samson Properties

    Lot 152 Christie Ln, Whitacre, VA 22625
    • 173 Sanctuary Dr, Winchester, VA 22603
      173 Sanctuary Dr, Winchester, VA 22603
      173 Sanctuary Dr, Winchester, VA 22603
      /38

      Est $296,956

      Not Listed For Sale

      173 Sanctuary Dr, Winchester, VA 22603

      • 3 Beds
      • 1 Bath
      • 864 Sq Ft
      • Built 1966
      173 Sanctuary Dr, Winchester, VA 22603

      Last Sold Summary

      • 137 Days On Market

  • 102 Duwamish Trail, Winchester, VA 22602
    102 Duwamish Trail, Winchester, VA 22602
    102 Duwamish Trail, Winchester, VA 22602
    /51

    $290,000

    Sold Sep 26, 2025

    102 Duwamish Trail, Winchester, VA 22602

    • 2 Beds
    • 4 Baths
    • 2,438 Sq Ft
    • Built 1971

    Last Sold Summary

    • $119/SF
    • 80 Days On Market

    Current Estimated Value $315,507

    Last Listing Agent Dorothy Beach Samson Properties

    102 Duwamish Trail, Winchester, VA 22602
    • 294 Bethel Grange Rd, Winchester, VA 22603
      294 Bethel Grange Rd, Winchester, VA 22603
      294 Bethel Grange Rd, Winchester, VA 22603
      /15

      Est $349,605

      Not Listed For Sale

      294 Bethel Grange Rd, Winchester, VA 22603

      • 3 Beds
      • 1 Bath
      • 1,576 Sq Ft
      • Built 1925
      294 Bethel Grange Rd, Winchester, VA 22603

      Last Sold Summary

      • 51 Days On Market

  • 124 Arrowhead Trail, Winchester, VA 22602
    124 Arrowhead Trail, Winchester, VA 22602
    124 Arrowhead Trail, Winchester, VA 22602
    /57

    $300,000

    Sold Feb 20, 2026

    124 Arrowhead Trail, Winchester, VA 22602

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1976

    Last Sold Summary

    • $240/SF
    • 8 Days On Market

    Current Estimated Value $304,085

    Last Listing Agent Lindsay Barnhart NextHome Realty Select

    124 Arrowhead Trail, Winchester, VA 22602
    • 270 Bethel Grange Rd, Winchester, VA 22603
      270 Bethel Grange Rd, Winchester, VA 22603
      270 Bethel Grange Rd, Winchester, VA 22603
      /17

      Not Listed For Sale

      270 Bethel Grange Rd, Winchester, VA 22603

      • 2 Beds
      • 1 Bath
      • 1,020 Sq Ft
      • Built 1971
      270 Bethel Grange Rd, Winchester, VA 22603

      Last Sold Summary

      • 11 Days On Market

  • 109 Waterside Ln, Cross Junction, VA 22625
    109 Waterside Ln, Cross Junction, VA 22625
    109 Waterside Ln, Cross Junction, VA 22625
    /107

    $495,000

    Sold Mar 20, 2026

    109 Waterside Ln, Cross Junction, VA 22625

    • 3 Beds
    • 3.5 Baths
    • 3,223 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $154/SF
    • 12 Days On Market

    Current Estimated Value $497,247

    Last Listing Agent Lisa Cox Colony Realty

    109 Waterside Ln, Cross Junction, VA 22625
    • 2206 Indian Hollow Rd, Winchester, VA 22603
      2206 Indian Hollow Rd, Winchester, VA 22603
      2206 Indian Hollow Rd, Winchester, VA 22603
      /110

      Est $807,770

      Not Listed For Sale

      2206 Indian Hollow Rd, Winchester, VA 22603

      • 4 Beds
      • 3.5 Baths
      • 3,806 Sq Ft
      • Built 1980
      2206 Indian Hollow Rd, Winchester, VA 22603

      Last Sold Summary

      • 4 Days On Market

  • 4163 Northwestern Pike, Winchester, VA 22603
    4163 Northwestern Pike, Winchester, VA 22603
    4163 Northwestern Pike, Winchester, VA 22603
    /30

    $214,000

    Sold Jun 30, 2025

    4163 Northwestern Pike, Winchester, VA 22603

    • 2 Beds
    • 1.5 Baths
    • 2,064 Sq Ft
    • Built 1930

    Last Sold Summary

    • $104/SF
    • 372 Days On Market

    Current Estimated Value $263,133

    Last Listing Agent Kristina Towns Weichert Realtors - Blue Ribbon

    4163 Northwestern Pike, Winchester, VA 22603

Showing Results 321 - 360, Page 9 of 18

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