5,481

Stephenson, VA Homes

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  • /18

    $425,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 1.5 Baths
    • 2,164 Sq Ft

    164 Bethel Grange Rd, Winchester, VA 22603

    This well-built all-brick home is offered for the first time since its construction and is situated on nearly an acre of land in a peaceful rural setting, just minutes from Winchester. Featuring main-level living, this home provides added convenience and functionality with a full basement that offers additional space for customization. The main level boasts newly refinished solid oak flooring

    Sarah Reynolds Keller Williams Realty

    164 Bethel Grange Rd, Winchester, VA 22603
  • /36

    $385,000 Sold Oct 20, 2025

    790 McDonald Rd, Winchester, VA 22602

    • 3 Beds
    • 2 Baths
    • 1,215 Sq Ft
    • Built 1966

    Last Sold Summary

    • $317/SF
    • 4 Days On Market

    Current Estimated Value $380,572

    Last Listing Agent Brian Doman Preslee Real Estate

    790 McDonald Rd, 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

      Last Listing Agent Mark Francis ICON Real Estate, LLC

  • /41

    $449,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,898 Sq Ft

    607 S Lakeview Dr, Cross Junction, VA 22625

    BIG price adjustment! Get it while it lasts! Brand-new construction at 607 South Lakeview Dr. offers a perfect blend of modern comfort, thoughtful design, and scenic surroundings. Construction is complete—this home is truly turnkey and move-in ready.Step inside to discover a desirable open floor plan designed for both comfortable living and effortless entertaining. The main level features a

    Carolyn Young Samson Properties

    607 S Lakeview Dr, Cross Junction, VA 22625
  • /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 $341,148

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

    111 Comanche Trail, Winchester, VA 22602
    • /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

      Last Listing Agent Lisa Cox Colony Realty

  • /35

    $550,000

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

    157 Oak Dr, Winchester, VA 22603

    NEW PRICE ALERT! 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, move-in-ready feel. Be Sure to Watch The Video to Experience Even More of This Home!The primary suite has been

    Phyllis Guthrie Keller Williams Realty

    157 Oak Dr, Winchester, VA 22603
  • /33

    $70,000 Sold Apr 14, 2025

    LOT 38 Southwood Dr, Whitacre, VA 22625

    • Land
    • 0.47 Acre
    • $148,936 per Acre

    Last Sold Summary

    • 3 Days On Market

    Last Listing Agent Lisa Cox Colony Realty

    LOT 38 Southwood Dr, Whitacre, VA 22625
    • /32

      Est $404,282 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

      • 12% Above List Price
      • $268/SF
      • 53 Days On Market

      Last Sold Price $360,000

      Last Listing Agent Ariel Guzman RE/MAX

  • /81

    $456,500

    • 3 Beds
    • 2 Baths
    • 2,094 Sq Ft

    101 Delaware Trail, Winchester, VA 22602

    Welcome to 101 Delaware Trail, a thoughtfully updated home nestled in the highly desirable Shawneeland community of Winchester, VA. Nearly the entire home has been updated, both inside and out, creating a fresh and modern living experience. Interior improvements include new flooring throughout (excluding existing wood flooring), an updated kitchen featuring Taj Mahal quartzite countertops, a

    Michael Putnam EXP Realty, LLC

    101 Delaware Trail, Winchester, VA 22602
  • /6

    $15,000 Sold Aug 29, 2025

    Lot 152 Fire Tower Trail, Shawneeland, VA 22602

    • Land
    • 0.78 Acre
    • $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
    • /44

      Est $325,999 Not Listed For Sale

      208 Poorhouse Rd, Winchester, VA 22603

      • 3 Beds
      • 1 Bath
      • 1,124 Sq Ft
      • Built 1950
      208 Poorhouse Rd, Winchester, VA 22603

      Last Sold Summary

      • 36% Above List Price
      • $214/SF
      • 9 Days On Market

      Last Sold Price $240,000

      Last Listing Agent Coral Dickinson Century 21 Redwood Realty

  • /15

    $399,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    7 Comanche Trail, Winchester, VA 22602

    Discover your dream home on a spacious, level lot, available for an end-of-April completion. This stunning new construction boasts a generous 3-bedroom, 2-full-bathroom layout, featuring an impressive list of builder upgrades included at no extra cost. Enjoy elegant hardwood flooring installed throughout the entire home, including all bedrooms, and classic tile in the baths. The gourmet kitchen

    Jim Thomson Realty ONE Group Old Towne

    7 Comanche Trail, Winchester, 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 $177,259

    Last Listing Agent Liz McDonald Dandridge Realty Group, LLC

    236 Doe Trail, Winchester, VA 22602
    • /42

      Est $281,313 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

      • $325/SF
      • 62 Days On Market

      Last Sold Price $280,000

      Last Listing Agent John Scully Colony Realty

  • /26

    $399,900 Under Contract

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

    129 Indiana Trail, Winchester, VA 22602

    I am done! Large lot on private street with valley views and private. HW floors entire main floor and stairs, tile floors in all baths, BUILDER BONUS HARDWOOD TO INCLUDE BEDROOMS (no carpet in house), UPGRADED CABINETS, GRANITE COUNTERTOPS IN KITCHEN. New Colonial home. 3 bed, 2.5 full baths, open floor plan, family rm, Kitchen w/ island and breakfast rm & sep. dining rm, Lg owner suite & true

    Jim Thomson Realty ONE Group Old Towne

    129 Indiana 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
    • /2

      Est $599,423 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

      • 22% Above List Price
      • $185/SF
      • 0 Days On Market

      Last Sold Price $490,000

      Last Listing Agent Emma Kerns MarketPlace REALTY

  • /2

    $390,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,148 Sq Ft

    4675 N Frederick Pike, Winchester, VA 22603

    COMING SOON! Enjoy peaceful country living with this 3-Bedroom, 1-Bath Rancher situated on nearly 7 unrestricted acres in beautiful Frederick County, VA! This Home features convenient one-level living, a full Unfinished Basement offering abundant storage or future expansion potential, a covered carport, and a deck perfect for enjoying the surrounding countryside. With nearly 7 acres of open

    Laura King MarketPlace REALTY

    4675 N Frederick Pike, Winchester, VA 22603
  • /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 $327,793

    Last Listing Agent Thomas Luster Epique Realty

    202 Falcon Trail, Winchester, VA 22602
    • /61

      Est $454,338 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

      • 1% Above List Price
      • $342/SF
      • 3 Days On Market

      Last Sold Price $449,000

      Last Listing Agent Sheila Pack RE/MAX

  • /27

    $399,900 New Construction

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

    107 Pinto Trail, Winchester, VA 22602

    3-17-26 almost done. Hurry! Level lot in the subdivision with views and privacy. "Brand New & Fully Loaded: Your Dream Home Awaits"The best value proposition in the subdivision! This stunning new construction offers 3 bedrooms, 3 full baths, and a 2-car side-load garage with excellent curb appeal. Comcast/Xfinity available on this street.Enjoy a flowing, open-concept design with a vaulted

    Jim Thomson Realty ONE Group Old Towne

    107 Pinto Trail, 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 $477,505

    Last Listing Agent Barbera Clausen EXP Realty, LLC

    669 Dicks Hollow Rd, Winchester, VA 22603
    • /37

      Est $213,113 Not Listed For Sale

      625 Round Hill Rd, Winchester, VA 22602

      • 2 Beds
      • 1 Bath
      • 902 Sq Ft
      • Built 1941
      625 Round Hill Rd, Winchester, VA 22602

      Last Sold Summary

      • 18% Above List Price
      • $200/SF
      • 3 Days On Market

      Last Sold Price $180,000

      Last Listing Agent Dallas Croft Samson Properties

  • /19

    $379,900 New Construction

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

    1619 Tomahawk Trail, Winchester, VA 22602

    Discover the best value for square footage in this stunning 3 bed, 3 bath home. Perched on over half an acre with panoramic mountain views. Enjoy an open floor plan, vaulted kitchen, hardwood floors throughout the main level & bedrooms, and a huge finished rec room. Builder bonuses include granite counters, kitchen island, and upgraded cabinets. Side-load 2-car garage & paved drive. A must-see!

    Jim Thomson Realty ONE Group Old Towne

    1619 Tomahawk 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 $409,200

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

    1133 Tomahawk Trail, Winchester, VA 22602
    • /49

      Est $432,998 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

      • 9% Above List Price
      • $246/SF
      • 1 Day On Market

      Last Sold Price $396,501

      Last Listing Agent Sheila Pack RE/MAX

  • /7

    $23,900

    • Land
    • 0.64 Acre
    • $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
  • /16

    $6,250 Sold Apr 18, 2025

    Lot 207 Southwood Dr, Whitacre, VA 22625

    • Land
    • 0 Acre

    Last Sold Summary

    • 1 Day On Market

    Last Listing Agent Misty Weaver Samson Properties

    Lot 207 Southwood Dr, Whitacre, VA 22625
    • /47

      Est $272,714 Not Listed For Sale

      178 Mount Vista Dr, Winchester, VA 22602

      • 3 Beds
      • 2 Baths
      • 1,625 Sq Ft
      • Built 1955
      178 Mount Vista Dr, Winchester, VA 22602

      Last Sold Summary

      • 1% Above List Price
      • $166/SF
      • 4 Days On Market

      Last Sold Price $270,000

      Last Listing Agent Kristen Kerns Roberts Realty Group, LLC

  • /2

    $7,000

    • Land
    • 0 Acre

    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
  • /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 $601,215

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

    231 Gun Barrel Ln, Winchester, VA 22603
    • /63

      Est $356,386 Not Listed For Sale

      716 Round Hill Rd, Winchester, VA 22602

      • 3 Beds
      • 2 Baths
      • 2,173 Sq Ft
      • Built 1940
      716 Round Hill Rd, Winchester, VA 22602

      Last Sold Summary

      • 10% Above List Price
      • $150/SF
      • 3 Days On Market

      Last Sold Price $325,000

      Last Listing Agent James Hartung RE/MAX

  • /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
  • /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
    • /41

      Est $445,618 Not Listed For Sale

      978 Round Hill Rd, Winchester, VA 22602

      • 3 Beds
      • 3 Baths
      • 1,970 Sq Ft
      • Built 2023
      978 Round Hill Rd, Winchester, VA 22602

      Last Sold Summary

      • 3% Above List Price
      • $221/SF
      • 20 Days On Market

      Last Sold Price $434,500

      Last Listing Agent Erick Erdal Long & Foster Real Estate, Inc.

  • /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
  • /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 $608,352

    Last Listing Agent Angela Duncan MarketPlace REALTY

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

      Est $277,582 Not Listed For Sale

      164 Singhass Rd, Winchester, VA 22602

      • 2 Beds
      • 1 Bath
      • 990 Sq Ft
      • Built 1956
      164 Singhass Rd, Winchester, VA 22602

      Last Sold Summary

      • 29% Above List Price
      • $217/SF
      • 38 Days On Market

      Last Sold Price $215,000

      Last Listing Agent Tanya Vergara Hoffman Realty

  • /62

    $715,000 Under Contract

    • 3 Beds
    • 3.5 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

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