5,497

Stephenson, VA Homes

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  • /43

    $625,000

    • 4 Beds
    • 3 Baths
    • 2,996 Sq Ft

    1564 Perry Rd, Winchester, VA 22602

    Discover the perfect blend of comfort and contemporary living in this stunning detached home, nestled on a generous 1.35-acre lot. Built in 2009, this residence boasts a modern architectural style that harmonizes with its serene surroundings, offering a peaceful retreat from the hustle and bustle of everyday life. Step inside to find a spacious layout that invites you to create lasting memories.

    Nate Vogel Century 21 Redwood Realty

    1564 Perry Rd, Winchester, VA 22602
  • /2

    $346,900 Sold Oct 14, 2025

    111 Comanche Trail, Winchester, VA 22602

    • 3 Beds
    • 2 Baths
    • 1,422 Sq Ft
    • Built 1992

    Last Sold Summary

    • $244/SF
    • 2 Days On Market

    Current Estimated Value $350,086

    Last Listing Agent George Glaize George W. Glaize, Jr., Inc. REALTOR

    111 Comanche Trail, Winchester, VA 22602
    • /6

      Not Listed For Sale

      0 Bobcat Trail, Gore, VA 22637

      0 Bobcat Trail, Gore, VA 22637

      Last Sold Summary

      • 22 Days On Market
      • Last Sold Price $77,000
      • Feb 26, 2025

      Last Listing Agent Andy Austin Double A Auction & Realty

  • /35

    $525,000 Pending

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

    157 Oak Dr, Winchester, VA 22603

    STOP THE PRESSES!! This PRICE ADJUSTMENT is not a typo! The weather is warmer and Spring is in the air.... This home is ready for YOU! Welcome home to 157 Oak Dr. in Winchester, VA—an inviting property offering comfort, thoughtful updates, and a peaceful setting. This home has been refreshed with luxury vinyl plank flooring throughout most of the home and fresh paint, creating a clean,

    Phyllis Guthrie Keller Williams Realty

    157 Oak Dr, Winchester, VA 22603
  • /6

    $15,000 Sold Aug 29, 2025

    Lot 152 Fire Tower Trail, Shawneeland, VA 22602

    • Land
    • 33,976 Sq Ft
    • $19,231 per Acre

    Last Sold Summary

    • 5 Days On Market

    Last Listing Agent Gina Griffith MarketPlace REALTY

    Lot 152 Fire Tower Trail, Shawneeland, VA 22602
    • /5

      Not Listed For Sale

      0 Bobcat Trail Unit 2500019, Winchester, VA 22602

      0 Bobcat Trail Unit 2500019, Winchester, VA 22602

      Last Sold Summary

      • 58 Days On Market
      • Last Sold Price $77,000
      • Feb 26, 2025

      Last Listing Agent Andy Austin Double A Auction & Realty

  • /7

    $23,900

    • Land
    • 27,878 Sq Ft
    • $37,344 per Acre

    Lot 9 Dogwood Trail, Back Creek, VA 22602

    Come see the views in this mountain community, potential building lot .64 acres, build your possible full or part time home or just recreational use. Hard top roads, road maintenance & amenities. Fishing, boating, Beach area, 2 recreational park areas, picnic pavilion, fishing ponds, baseball field, basketball hoops. Take a ride to the top & enjoy all the wonderful Mountain Views. Peaceful &

    Gina Griffith MarketPlace REALTY

    Lot 9 Dogwood Trail, Back Creek, VA 22602
  • /15

    $159,900 Sold Jul 29, 2025

    236 Doe Trail, Winchester, VA 22602

    • 1 Bed
    • 1 Bath
    • 861 Sq Ft
    • Built 1971

    Last Sold Summary

    • $186/SF
    • 222 Days On Market

    Current Estimated Value $179,133

    Last Listing Agent Liz McDonald Dandridge Realty Group, LLC

    236 Doe Trail, Winchester, VA 22602
    • /13

      Not Listed For Sale

      0 Back Creek Rd Unit VAFV2022922, Gore, VA 22637

      0 Back Creek Rd Unit VAFV2022922, Gore, VA 22637

      Last Sold Summary

      • 102 Days On Market
      • Last Sold Price $65,000
      • Mar 31, 2025

      Last Listing Agent Karl Achstetter Keller Williams Realty

  • /20

    $399,900 New Construction

    • 3 Beds
    • 3 Baths
    • 1,914 Sq Ft

    103 Tonto Trail, Winchester, VA 22602

    Current Shawneeland Inventory208 Beaver Trail210 Beaver Trail212 Falcon Trail211 Inca Trail116 Pinto Trail103 Tonto Trail123 Killbuck TrailStunning 3BR/3BA home on over 1/3 acre lot with available Xfinity internet (not all streets have it). Easy entrance access. Open floor plan features vaulted family room & kitchen. Upgraded kitchen boasts Bonus Granite Island &

    Jim Thomson Realty ONE Group Old Towne

    103 Tonto Trail, Winchester, VA 22602
  • /5

    $90,000 Sold Jul 17, 2025

    310 Burnt Church Rd, Winchester, VA 22603

    • Land
    • 3.5 Acres
    • $25,714 per Acre

    Last Sold Summary

    • 41 Days On Market

    Last Listing Agent Gillian Greenfield Coldwell Banker Premier

    310 Burnt Church Rd, Winchester, VA 22603
    • /9

      Not Listed For Sale

      0 Shenandoah Trail, Winchester, VA 22602

      0 Shenandoah Trail, Winchester, VA 22602

      Last Sold Summary

      • 2 Days On Market
      • Last Sold Price $15,000
      • Dec 19, 2024

      Last Listing Agent Stephanie Feltner Realty ONE Group Old Towne

  • /2

    $7,000

    • Land
    • 0 Sq Ft

    Lot 95 Southwood Dr, Whitacre, VA 22625

    Non Buildable lot in the Lake Holiday community offering access to lake privileges and community amenities. Enjoy boating, swimming, beaches, and shared recreational areas in this gated lake community. Why wait till spring to begin exploring options for summer fun?! Explore all that Lake Holiday has to offer now and be ready to make memories on the lake before summer rolls around.

    Machelle Lewis Impresa Premier Realty LLC

    Lot 95 Southwood Dr, Whitacre, VA 22625
  • /23

    $329,900 Sold Jun 27, 2025

    202 Falcon Trail, Winchester, VA 22602

    • 3 Beds
    • 2 Baths
    • 1,272 Sq Ft
    • Built 1976

    Last Sold Summary

    • $259/SF
    • 23 Days On Market

    Current Estimated Value $325,330

    Last Listing Agent Thomas Luster Epique Realty

    202 Falcon Trail, Winchester, VA 22602
    • /14

      Not Listed For Sale

      0 Doe Trail Unit VAFV2022816, Winchester, VA 22602

      0 Doe Trail Unit VAFV2022816, Winchester, VA 22602

      Last Sold Summary

      • 2 Days On Market
      • Last Sold Price $25,000
      • Jan 30, 2025

      Last Listing Agent Stephanie Feltner Realty ONE Group Old Towne

  • /6

    $200,000

    • Land
    • 5 Acres
    • $40,000 per Acre

    Lot B Cather Ln, Winchester, VA 22602

    Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

    Kaitlyn Behr Samson Properties

    Lot B Cather Ln, Winchester, VA 22602
  • /53

    $475,000 Sold Aug 21, 2025

    669 Dicks Hollow Rd, Winchester, VA 22603

    • 4 Beds
    • 2 Baths
    • 2,012 Sq Ft
    • Built 1950

    Last Sold Summary

    • $236/SF
    • 71 Days On Market

    Current Estimated Value $484,862

    Last Listing Agent Barbera Clausen EXP Realty, LLC

    669 Dicks Hollow Rd, Winchester, VA 22603
    • /4

      Not Listed For Sale

      Lot 16 E Lincoln Estates Subdivision, Winchester, VA 22602

      Lot 16 E Lincoln Estates Subdivision, Winchester, VA 22602

      Last Sold Summary

      • 14 Days On Market
      • Last Sold Price $40,000
      • Jan 17, 2025

      Last Listing Agent Tracy Link Coldwell Banker Premier

  • /50

    $359,900 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,552 Sq Ft

    109 Huron Trail, Winchester, VA 22602

    Discover this inviting 3-bedroom, 2-bath tri‐level home, offering flexible living spaces and a unique layout designed for comfort and creativity. The main level features a bright kitchen and a welcoming living room, setting the tone for easy everyday living. The upper-level hosts three full bedrooms, including a comfortable primary suite with its own ensuite bath, along with a well‐appointed full

    LESLIE WEBB Long & Foster Real Estate, Inc.

    109 Huron Trail, Winchester, VA 22602
  • /98

    $400,000 Sold Feb 13, 2026

    1133 Tomahawk Trail, Winchester, VA 22602

    • 3 Beds
    • 2 Baths
    • 2,325 Sq Ft
    • Built 1975

    Last Sold Summary

    • $172/SF
    • 106 Days On Market

    Current Estimated Value $393,715

    Last Listing Agent Sue Goodwin Long & Foster Real Estate, Inc.

    1133 Tomahawk Trail, Winchester, VA 22602
    • /25

      Not Listed For Sale

      Lot 98 S Lakeview Dr, Whitacre, VA 22625

      Lot 98 S Lakeview Dr, Whitacre, VA 22625

      Last Sold Summary

      • 63 Days On Market
      • Last Sold Price $20,000
      • Jan 24, 2025

      Last Listing Agent Mark Francis ICON Real Estate, LLC

  • /9

    $166,000 Under Contract

    • Land
    • 59.93 Acres
    • $2,770 per Acre

    0 Tomahawk Trail Unit VAFV2033070, Winchester, VA 22602

    UNIQUE 60 ACRE WOODED TRACT within the Great North Mountain Wilderness Area enhanced by County maintained hard surfaced road access and available electricity. The Offering also includes a contiguous half acre building Lot (Shawneeland - Tax ID 49-A05-1-W-1) which is located adjacent to the main tracts access point at the intersection of Tomahawk and Jalapa. Potential forty plus mile views

    Wayne Wilson Thomas and Talbot Estate Properties, Inc.

    0 Tomahawk Trail Unit VAFV2033070, Winchester, VA 22602
  • /65

    $600,000 Sold Oct 31, 2025

    231 Gun Barrel Ln, Winchester, VA 22603

    • 3 Beds
    • 2.5 Baths
    • 3,283 Sq Ft
    • Built 2004

    Last Sold Summary

    • $183/SF
    • 12 Days On Market

    Current Estimated Value $608,655

    Last Listing Agent Dennis Virts RE/MAX Distinctive Real Estate, Inc.

    231 Gun Barrel Ln, Winchester, VA 22603
    • /13

      Not Listed For Sale

      LOT 241 S Lakeview Dr, Whitacre, VA 22625

      LOT 241 S Lakeview Dr, Whitacre, VA 22625

      Last Sold Summary

      • 15 Days On Market
      • Last Sold Price $6,000
      • Oct 30, 2024

      Last Listing Agent Lisa Cox Colony Realty

  • /62

    $715,000 Pending

    • 2 Beds
    • 3 Baths
    • 4,808 Sq Ft

    121 Windrow Ct, Winchester, VA 22602

    Exquisite Home In Frederick County VA. This Custom Built Ranch Style Home Is The Perfect One Level Living Home, With Over 5,000 Finished Square Feet Of Living Space. The Open Living Concept Offers 9+ Foot Ceilings, High Loft Ceiling With Custom Wooden Decorative Beams And Floor To Ceiling Fireplace In Main Living Room With Decorative Wood Trim And Mantle, Kitchen To Living Room Space With Full

    Tracy Link Coldwell Banker Premier

    121 Windrow Ct, Winchester, VA 22602
  • /31

    $254,000 Sold May 28, 2025

    105 Deer Trail, Winchester, VA 22602

    • 2 Beds
    • 2 Baths
    • 800 Sq Ft
    • Built 1973

    Last Sold Summary

    • $318/SF
    • 2 Days On Market

    Current Estimated Value $262,765

    Last Listing Agent Nadeem Helfer Samson Properties

    105 Deer Trail, Winchester, VA 22602
    • /32

      Est $389,684 Not Listed For Sale

      180 Dicks Hollow Rd, Winchester, VA 22603

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 2003
      180 Dicks Hollow Rd, Winchester, VA 22603

      Last Sold Summary

      • 8% Above List Price
      • $268/SF
      • 53 Days On Market
      • Last Sold Price $360,000
      • Sep 27, 2024

      Last Listing Agent Ariel Guzman RE/MAX

  • /6

    $20,000

    • Land
    • 20,037 Sq Ft
    • $43,478 per Acre

    Lot 102 Bow Wood Trail, Winchester, VA 22602

    A Hidden Gem Waiting for YouNestled in the serene countryside of Winchester, Virginia, lies a great treed building lot on the lower side of Shawneeland. This picturesque piece of land offers the perfect blend of seclusion and convenience, making it an ideal location for building your dream home.Enjoy the tranquility and natural beauty of Shawneeland's private parks, perfect for relaxing

    Rick Guthrie Keller Williams Realty

    Lot 102 Bow Wood Trail, Winchester, VA 22602
  • /53

    $604,000 Sold May 23, 2025

    219 Plow Run Ln, Winchester, VA 22602

    • 3 Beds
    • 2 Baths
    • 2,177 Sq Ft
    • Built 2017

    Last Sold Summary

    • $277/SF
    • 99 Days On Market

    Current Estimated Value $621,469

    Last Listing Agent Angela Duncan MarketPlace REALTY

    219 Plow Run Ln, Winchester, VA 22602
    • /42

      Est $267,727 Not Listed For Sale

      293 Poorhouse Rd, Winchester, VA 22603

      • 2 Beds
      • 1 Bath
      • 862 Sq Ft
      • Built 1970
      293 Poorhouse Rd, Winchester, VA 22603

      Last Sold Summary

      • 4% Below List Price
      • $325/SF
      • 62 Days On Market
      • Last Sold Price $280,000
      • Feb 18, 2025

      Last Listing Agent John Scully Colony Realty

  • /29

    $259,900

    • 2 Beds
    • 1 Bath
    • 924 Sq Ft

    111 Genesee Trail, Winchester, VA 22602

    Remodeled rancher on 4 lots totaling 1.41 acres. Cute 2 bedroom 1 bath home freshly painted with new luxury vinyl planking throughout the entire house. Brand new bathroom with tub /shower. Open floor plan with bedrooms on each end of the house for privacy. 2 sheds that convey to store whatever your heart desires. Front deck to be stained as soon as weather permits. Come out and and enjoy all the

    Jacquelyn Rizzari MarketPlace REALTY

    111 Genesee Trail, Winchester, VA 22602
  • /2

    $23,000 Sold Feb 27, 2026

    Lot 60 Susquehanna Trail, Shawneeland, VA 22602

    • Land
    • 10,018 Sq Ft
    • $100,000 per Acre

    Last Sold Summary

    • 2 Days On Market

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

    Lot 60 Susquehanna Trail, Shawneeland, VA 22602
    • /2

      Est $583,797 Not Listed For Sale

      2680 Northwestern Pike, Winchester, VA 22603

      • 3 Beds
      • 6 Baths
      • 2,645 Sq Ft
      • Built 1968
      2680 Northwestern Pike, Winchester, VA 22603

      Last Sold Summary

      • 19% Above List Price
      • $185/SF
      • 0 Days On Market
      • Last Sold Price $490,000
      • May 31, 2023

      Last Listing Agent Emma Kerns MarketPlace REALTY

  • /7

    $200,000

    • Land
    • 5 Acres
    • $40,000 per Acre

    Lot A Cather Ln, Winchester, VA 22602

    Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

    Kaitlyn Behr Samson Properties

    Lot A Cather Ln, Winchester, VA 22602
  • /15

    $52,000 Sold Mar 27, 2026

    LOT 152 Bobcat Trail, Winchester, VA 22602

    • Land
    • 1.3 Acres
    • $40,000 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 81 Days On Market

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

    LOT 152 Bobcat Trail, Winchester, VA 22602
    • /61

      Est $465,792 Not Listed For Sale

      227 Skyview Ln, Winchester, VA 22603

      • 3 Beds
      • 2 Baths
      • 1,311 Sq Ft
      • Built 1926
      227 Skyview Ln, Winchester, VA 22603

      Last Sold Summary

      • 4% Above List Price
      • $342/SF
      • 3 Days On Market
      • Last Sold Price $449,000
      • Sep 16, 2024

      Last Listing Agent Sheila Pack RE/MAX

  • /28

    $399,000

    • 4 Beds
    • 2 Baths
    • 2,031 Sq Ft

    5990 Northwestern Pike, Gore, VA 22637

    *HUGE PRICE IMPROVEMENT – YOUR 10-ACRE OPPORTUNITY AWAITS!This SPRAWLING 9.8-acre estate offers the ultimate rural retreat without sacrificing modern convenience. Stop dreaming of more space and start owning it! Now at a newly improved price point, BRING ALL OFFERS! PRIME LOCATION! Tucked away in a mountain-view sanctuary, yet only 7 minutes from the WV border and 15 minutes from the heart of

    Kristi Massie Story House Real Estate

    5990 Northwestern Pike, Gore, VA 22637
  • /62

    $534,000 Sold Jun 11, 2025

    6880 Northwestern Pike, Gore, VA 22637

    • 4 Beds
    • 2.5 Baths
    • 2,681 Sq Ft
    • Built 1967

    Last Sold Summary

    • $199/SF
    • 6 Days On Market

    Current Estimated Value $546,033

    Last Listing Agent Tracie Clawson ERA Oakcrest Realty, Inc.

    6880 Northwestern Pike, Gore, VA 22637
    • /49

      Est $435,329 Not Listed For Sale

      205 Crinoline Ln, Winchester, VA 22603

      • 3 Beds
      • 2 Baths
      • 1,614 Sq Ft
      • Built 1992
      205 Crinoline Ln, Winchester, VA 22603

      Last Sold Summary

      • 10% Above List Price
      • $246/SF
      • 1 Day On Market
      • Last Sold Price $396,501
      • May 12, 2023

      Last Listing Agent Sheila Pack RE/MAX

  • /62

    $310,000

    • 3 Beds
    • 2 Baths
    • 1,100 Sq Ft

    105 Buckskin Trail, Winchester, VA 22602

    Nestled in the charming Shawneeland community, you will enjoy the mountain views in this delightful ranch-style home which offers a perfect blend of comfort and modern living. With a major renovation completed in 2026, this residence boasts a fresh and inviting atmosphere, ideal for creating lasting memories. The exterior features low-maintenance vinyl siding, complemented exterior lighting that

    Bruce Elsey Long & Foster Real Estate, Inc.

    105 Buckskin Trail, Winchester, VA 22602

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