148 Jeb Dr, Winchester, VA 22602
Property image
Property image
SOLD
DEC 23, 2025

$665,000

Currently Off Market - Sold Dec 23, 2025 for $665,000 (22,067% above list price)
  • 3 Beds
  • 4 Baths
  • 3,000 sqft
  • 3 Beds
  • 4 Baths
  • 3,000 sqft

148 Jeb Dr, Winchester, VA 22602

Home Highlights

Property Type
Single-Family Home
Living Area
3,000 sqft
Price/Sqft
$222/sqft
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 148 Jeb Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Beautiful Country Home on 5 Acres Great Room, Sunroom, Library & Finished Basement

Escape to peaceful country living in this beautifully updated 3+ bedroom home with stunning views and abundant natural light throughout.

Freshly painted and move-in ready, this spacious home offers:

3 generously sized bedrooms, plus a basement room suitable for use as a 4th bedroom

4 full bathrooms

Bright sunroom perfect for morning coffee or relaxing evenings

Private library/home office

Hardwood floors throughout

Full finished basement with large recreation room

Expansive windows with gorgeous views

Recently updated interior

The open, light-filled layout creates a warm and welcoming atmosphere, ideal for both everyday living and entertaining. The finished basement provides excellent additional living space perfect for a media room, game room, or guest area.

Located in a highly desirable area with excellent schools, this property offers the tranquility of country living while still being conveniently accessible to town amenities.

Enjoy privacy, space, and comfort all in one exceptional rental.

Please TEXT with questions or to schedule a showing.

Renter responsible for electric and gas. Property is on well and septic system. HOA fees paid by owner.
148 Jeb Dr, Winchester, VA 22602 is a 3 bedroom, 4 bathroom, 3,000 sqft single-family home. It last sold for $665,000 on Dec 23, 2025 (22,067% above the $3,000 asking price). More recently, it was listed as a rental in February 2026 with an asking price of $3,000 per month. That rental listing was removed on March 31, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $689,000, with a rent estimate of $3,219/month.

Home Details for 148 Jeb Dr

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: Central AirHeating Fuel: Heat Pump
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Exterior Features

Parking & Garage
Parking: Attached, On Site

Price & Status

Price
Price Per Sqft: $222/sqft

Comparable Sales for 148 Jeb Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
478 Brookneil Dr, Winchester, VA
0.35
Single-Family Home
$582,500
12/03/25
4
3.5
3,296 sqft
756 Brookneil Dr, Winchester, VA
0.31
Single-Family Home
$805,000
10/17/25
4
3.5
3,942 sqft
278 Rubinette Way, Winchester, VA
0.47
Single-Family Home
$800,000
05/19/26
3
3.5
2,577 sqft
137 Stonebrook Rd, Winchester, VA
0.46
Single-Family Home
$705,000
02/03/26
4
4
3,783 sqft
138 Old Forest Cir, Winchester, VA
0.50
Single-Family Home
$568,300
06/26/26
4
3.5
2,661 sqft
140 Stonebrook Rd, Winchester, VA
0.53
Single-Family Home
$677,500
08/27/26
4
3
3,300 sqft
314 Greenfield Ave, Winchester, VA
0.51
Single-Family Home
$576,000
07/13/26
4
2.5
2,520 sqft
162 Janes Way, Winchester, VA
0.55
Single-Family Home
$770,000
02/25/26
4
3.5
4,461 sqft
108 Katie Ln, Winchester, VA
0.58
Single-Family Home
$644,000
11/21/25
5
3.5
4,144 sqft

Nearby homes

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Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Mar 31, 2026
Source: Zillow Rentals
ListingRemoved
$3,000
Feb 23, 2026
Source: Zillow Rentals
Listed For Rent
$3,000
Dec 23, 2025
Source: N/A
Sold
$665,000

Frequently asked questions about 148 Jeb Dr

  • What is 148 Jeb Dr estimated to be worth?
    Trulia's estimated value for 148 Jeb Dr in Winchester, VA is $689,000.
  • What is the price history for 148 Jeb Dr?
    148 Jeb Dr in Winchester, VA last sold for $665,000 in December 2025.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $390K. That is up $10K from the prior month.
  • Does 148 Jeb Dr have air conditioning?
    Yes, 148 Jeb Dr in Winchester, VA has air conditioning.
  • Does 148 Jeb Dr have laundry facilities?
    Yes, 148 Jeb Dr in Winchester, VA has in-unit laundry.

Homes for rent near 148 Jeb Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
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Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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