Oak Dr, Winchester, VA 22603
Property image
Property image
PENDING
5 ACRES

$125,000

    Oak Dr, Winchester, VA 22603

    Est. Mortgage $773/mo*
    Get Pre-Qualified

    Home Highlights

    HOA
    $25/Monthly
    Listed
    128 days ago

    Local Information

    • Map ViewExplore the area around Oak Dr.
    • Schools1 Preschool School1 Elementary School1 Middle School1 High School
    • Shop & Eat
    -- mins to
    Commute Destination

    About this House

    Enjoy rural living and fun on this building lot in the Westwood Terrace community. This prime building lot is located off of Pinehill Drive at the base of Hunting Ridge. Access is secured via road frontage on paved Oak Drive and graveled Day Drive. Electricity and other utilities are nearby making for cost effective hookups. This land is zoned RA and the topography ranges from mild to steep. Ideal location to build a permanent residence or a weekend getaway for you and the family. Gorgeous views of the surrounding countryside are available from the upper elevations of this tract with some tree clearing. Deer and turkey frequent the area along with small game species. Access to all the amenities and entertainment Winchester has to offer are just a short drive away. No soil work has been done.
    Last check for updates: about 9 hours ago
    Listing courtesy of Chad Pangle, (540) 975-3487
    Whitetail Properties Real Estate, LLC, (217) 285-9000
    Source: Bright MLS, MLS#VAFV2041120

    Home Details for Oak Dr

    Interior Features

    View
    No View

    Exterior Features

    Frontage
    Not on Waterfront
    Water & Sewer
    Sewer: No Septic Approved

    Days on Market

    Days on Market: 128

    Property Information

    Property Type / Style
    Property Type: LandProperty Subtype: Unimproved Land
    Building
    No Additional Parcels
    Property Information
    Parcel Number: 4073

    Price & Status

    Price
    List Price: $125,000
    Status Change & Dates
    Off Market Date: Wed Jun 24 2026Possession Timing: Close Of Escrow

    Active Status

    MLS Status: PENDING

    Location

    Direction & Address
    City: WINCHESTER
    School Information
    Elementary School District: Frederick County Public SchoolsJr High / Middle School District: Frederick County Public SchoolsHigh School District: Frederick County Public Schools

    Agent Information

    Listing Agent
    Listing ID: VAFV2041120

    HOA

    Has an HOAHOA Fee: $300/Annually

    Lot Information

    Lot Area: 5 Acres

    Listing Info

    Special Conditions: Standard

    Offer

    Listing Agreement Type: Exclusive Right To Sell

    Business

    Business Information
    Ownership: Fee Simple

    Miscellaneous

    Mls Number: VAFV2041120

    Additional Information

    Source Internet Automated Valuation Display: YSource Internet Consumer Comment: YSource Internet Entire Listing Display: YSource Internet Address Display: Y

    Around this home

    What Locals Say about Winchester

    At least 465 Trulia users voted on each feature.

    • 84 % Say car is needed

    • 81 % Say it's dog friendly

    • 81 % Say parking is easy

    • 77 % Say yards are well-kept

    • 73 % Say there's holiday spirit

    • 69 % Say kids play outside

    • 64 % Say people would walk alone at night

    • 64 % Say there are sidewalks

    • 59 % Say streets are well-lit

    • 55 % Say it's quiet

    • 52 % Say neighbors are friendly

    • 49 % Say it's walkable to restaurants

    • 49 % Say there's wildlife

    • 48 % Say they plan to stay for at least 5 years

    • 36 % Say it's walkable to grocery stores

    • 28 % Say there are community events

    Sourced by Trulia users. Learn more about our methodology.
    • 7seymours
      "It’s quiet, owners take care of their homes, and it’s safe! And pretty! "
      4
      Flag
    • Hmrtgptw2c
      "I drive to and from work. The city has public transportation with WinReady I think it’s called. There is ride share in the area as well."
      4
      Flag
    • George
      "I’ve only lived here several weeks but am impressed by the people in our neighborhood. Polite and friendly."
      10
      Flag
    • Jessica J Contreras
      "There are no sidewalks or safe areas to walk with pets. Cars go by fast. It would be unsafe to walk. "
      2
      Flag
    • 7seymours
      "We live in a beautiful, safe area with an excellent county school system. Our neighbors have pride and take care of their properties in the Green Spring area"
      10
      Flag
    • Izzy874
      "Apple blossom every single year I love it! The food is amazing, the games, the carnival, and especially the parades and events to go too!"
      4
      Flag
    • Singsongone
      "Lived in this quiet neighborhood little over ten years. Convenient to major highways and bypasses, hospital, doctors, grocery and retail stores, restaurants. Lovely mature trees throughout, some wildlife and one can easily hear morning/evening birds. Residents take pride in the appearance of their homes and yards and look out for one another. "
      5
      Flag
    • Smlrws
      "I’ve lived here for a year and my street is much quieter than I ever expected since I live with a mile of the downtown area. It’s safe. There are many restaurants, coffe shops, hair salons, etc. within walking distance !"
      5
      Flag
    • Kelrendon83
      "Great community for live , safe and good for raise kids and the family can have a good place to visit , some good festivals "
      12
      Flag
    • 7seymours
      "Lived here for 22 yrs. Beautiful, spacious, quiet and good neighbors! We feel safe here with a lot of privacy. Neighbors look out for each other & help each other "
      11
      Flag
    • Gfbzc98z9n
      "It is Quiet and safe while still being just a short trip to the big city. Beautiful downtown walking mall. Great outdoors all around in the Blue Ridge Mountains."
      9
      Flag
    • 7seymours
      "Apple Blossom Festival which is held annually with parades, celebrities, dances, music & arts & crafts. A beautiful weekend during Apple Blossom time with over 250,000 visitors attending this special event in the Shenandoah Valley "
      10
      Flag
    • Trulia User
      "Everyone I have ran into has been nice. Definitely a very family friendly neighborhood. Feels very cozy "
      8
      Flag
    • Morganva
      "Dog friendly, plenty of green space, and lots of dog bag dispensers for cleaning up after the pooch. "
      8
      Flag
    • Bridgetdefoe
      "It’s easy to get around Winchester. Roads are well maintained. Traffic is minimal. You can get about anywhere in Winchester is less than 20 minutes. Rt 7 has become busy as an exception due to people commuting to Loudoun County "
      9
      Flag
    • Isabelle M.
      "Is a nice ride and no traffic in the area, many shopping centers, great area to visit, one of the great hospital in the nation."
      7
      Flag
    • Alliav11%40gmail.com
      "A lot of people have dogs here and they are always waking them. There are a lot of stray cats so if dogs don’t like them beware"
      0
      Flag
    • Gina A.
      "It's just a nice neighborhood to walk. People are always waving and stopping to chat. And they clean up after their dogs"
      4
      Flag
    • Cooda K.
      "It’s a lot It’s a lot I can say I honestly feel like it’s a beautiful place I mean the cabs suck But other than that I feel like it’s a nice expensive place to live 😁 "
      3
      Flag
    • Topeye
      "Very good schools, low crime rate, good jobs. Civic pride. Great long-running annual community festival. Many churches and civic organizations are active. Historic preservation. "
      5
      Flag
    • Rob R.
      "My commute to downtown is usually fairly quick, not too much traffic. Public transportation is not very popular."
      3
      Flag
    • Nickruiz270
      "The commute into Winchester is fairly light but around 5pm it’s when it gets heavy. I would try to avoid all small roads as much as possible and use the highway as much as possible. "
      2
      Flag
    • Careliza81
      "We are just walking distance to the walking mall which has tons of activities throughout the year. There are festivals for most major holidays and apple blossom. "
      3
      Flag
    • Nick A.
      "There is a great community of people here and it’s very welcoming. Living here is home for me and I would recommend moving here if you want to be close to major metropolis and still be near countryside"
      3
      Flag
    • Chels J.
      "Great safe place for kids no strange people more of a older group of people live here. It’s out of the way of the city but seconds from town"
      51
      Flag
    • Brock M.
      "Great area to live and raise a family. Good earnings potential. Great university. Awesome private and public school system."
      2
      Flag
    • Coach_ramos
      "You must drive or carpool. There is a local bus/trolley, but only locally within the city. No rail or subway."
      2
      Flag
    • Leslie H.
      "I commute to Northern Va and Loudoun Co. it’s more brutal each year, especially the return commute. "
      0
      Flag
    • Brad M.
      "Old town feel and downtown is lively. We enjoy being able to walk in a safe environment and walk to restaurants and shops. A great place to live in a historic town. "
      2
      Flag
    • Yesenia R.
      "The community center provides events for all. From all the holidays to special events for fundraisers along with also assisting the community with school supplies. There’s also playgrounds and pools."
      2
      Flag
    • Danielle M.
      "There are no community events in my neighborhood...everyone mostly keeps to themselves with the exception of those of us who have lived here for over thirty years. "
      0
      Flag
    • Erin G. .
      "Nothing special, just a nice neighborhood. Nice and quiet. Friendly folks. Safe for kids to play. Convenient to shopping."
      1
      Flag
    • Samantha F.
      "There is a large park just a few blocks away. Enough room to let a we trained dog off the leash. Walking distance to downtown dog friendly restaurants. "
      0
      Flag
    • Topeye
      "The public library across the street and the pedestrian mall 2 blocks away frequently hold community events."
      1
      Flag
    • Juanita e
      "dog owners would love this area great place to live great county sitting quite schools stores dr.s hospital close malls shopping casinos horse racing car raises movies drive in s close tons restaurants parks city county parks swimming snow skiing within hour"
      0
      Flag
    • Andrea
      "Nothing. Nice area not much for kid s to do no playgrounds or nearby parks but nice for adults "
      0
      Flag
    • Destiny W.
      "There's a big Park perfect for taking your dog. Plus you'll see all kinds of dogs being walked downtown on the waking mall. A few businesses even put a water bowl out for the dogs that walk by"
      2
      Flag
    • Debra T.
      "There is a bus stop only a few minutes from my front door. I know you can take the bus down town! I am not sure about long distance travel!"
      1
      Flag
    • Island4tj
      "The city is relatively safe and the schools are very good. Nice, clean town to live in that’s family-oriented. "
      1
      Flag
    • Ruizy8329
      "The neighborhood provides many sidewalks and grassy areas for peaceful and well lit dog walking. People in the area mostly have pets and those who don’t are usually very good about it. "
      1
      Flag

    Market trends in Winchester

    Last updated July 2026
    Buyer'sMarketSeller'sMarket
    Avg. sale price
    $390K
    $10K    MoM
    Sale-to-List Price
    100.0%
    Price per sq ft
    $222
    $6    MoM
    Available listings
    307
    5    MoM

    Home Value

    Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

    Comparable sales

    These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
    Address
    Distance
    Property Type
    Sold Price
    Sold Date
    Bed
    Bath
    Sqft
    Gun Barrel Ln, Winchester, VA
    1.01
    Lot/Land
    $80,000
    01/20/26
    -
    -
    Gun Barrel Ln, Winchester, VA
    0.98
    Lot/Land
    $80,000
    01/20/26
    -
    -
    1389 Back Mountain Rd, Winchester, VA
    0.55
    Lot/Land
    $1,200,000
    04/24/26
    -
    -
    Lot 6 Deer Run Dr, Winchester, VA
    1.69
    Lot/Land
    $65,000
    11/25/25
    -
    -
    Hedrick Ln, Winchester, VA
    1.76
    Lot/Land
    $88,000
    06/11/26
    -
    -
    33 Quail Run Ln, Winchester, VA
    2.17
    Lot/Land
    $200,000
    12/01/25
    -
    -
    1280 Bobcat Trl, Winchester, VA
    3.00
    Lot/Land
    $119,000
    07/16/26
    -
    -
    440 Iris Ln, Winchester, VA
    3.23
    Lot/Land
    $84,800
    04/10/26
    -
    -
    Lot 31 Pinto Trl, Winchester, VA
    2.77
    Lot/Land
    $16,500
    11/26/25
    -
    -
    Lot 20 Pinto Trl, Winchester, VA
    2.86
    Lot/Land
    $16,500
    11/26/25
    -
    -

    Nearby home prices

    Get a sense of expected prices in the area by checking the value of nearby homes.
    Address
    Distance
    Price
    Bed
    Bath
    Sqft
    Status
    157 Oak Dr, Winchester, VA 22603
    0.05
    $534,000
    4
    2.5
    2,280
    Recently Sold
    5 Oak Dr, Winchester, VA 22603
    0.11
    -
    -
    -
    -
    Off Market
    181 Oak Dr, Winchester, VA 22603
    0.13
    $199,900
    -
    -
    -
    For Sale
    7 Oak Dr, Winchester, VA 22603
    0.28
    $199,900
    -
    -
    -
    For Sale
    232 Devland Dr, Winchester, VA 22603
    0.34
    $636,200
    4
    3.5
    3,578
    Off Market
    159 Devland Dr, Winchester, VA 22603
    0.37
    $428,800
    3
    3
    1,758
    Off Market
    Northwestern Pike And Back Mountain Rd, Winchester, VA 22602
    0.48
    -
    -
    -
    -
    Off Market
    1389 Back Mountain Rd, Winchester, VA 22602
    0.55
    $1,200,000
    -
    -
    -
    Recently Sold
    0 Back Mountain Road, Winchester, VA 22602
    0.57
    -
    -
    -
    -
    Off Market
    4163 Northwestern Pike, Winchester, VA 22603
    0.67
    $227,000
    2
    1.5
    2,064
    Off Market
    510 Devland Dr, Winchester, VA 22603
    0.65
    $714,000
    4
    3
    3,690
    Off Market
    156 Whiskey Bottom Ct, Winchester, VA 22603
    0.68
    $532,600
    3
    2
    -
    Off Market

    Price and Tax history

    DateEventPrice
    Jun 24, 2026
    Source: Bright MLS #VAFV2041120
    		Pending
    $125,000
    May 5, 2026
    Source: Bright MLS #VAFV2041120
    		Contingent
    $125,000
    Apr 24, 2026
    Source: Bright MLS #VAFV2041120
    		Listed For Sale
    $125,000

    LGBTQ Local Legal Protections

    Chad Pangle, Whitetail Properties Real Estate, LLC, (217) 285-9000
    Agent Phone: (540) 975-3487
    The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

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    Frequently asked questions about Oak Dr

    • How big is Oak Dr?
      Oak Dr in Winchester, VA is about 5 acres.
    • What is the price per acre for Oak Dr?
      Oak Dr in Winchester, VA is listed at $125,000, or about $25K per acre.
    • What do residents say about Winchester?
      Residents describe Winchester, VA as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See homes for sale in Winchester, VA.
    • What are the closest schools to Oak Dr?
      The closest schools to Oak Dr in Winchester, VA are Frederick County Middle School (rated 2/10), Indian Hollow Elementary School (Pre-K, rated 5/10), James Wood High School (rated 6/10).
    Oak Dr, Winchester, VA 22603 is a lot/land. This property is currently available for sale and was listed by Bright MLS on Apr 24, 2026. The MLS # for this home is MLS# VAFV2041120.