1399 Chestnut Grove Rd Winchester, VA 22603
Property details
About 1399 Chestnut Grove Rd
One Level home on a private 5 acre lot. Bring your horses, goats, chickens - this is the perfect farmette! Absolutely beautiful setting that includes a paddock and a barn/shed. New roof April 2025. New Laminate flooring in kitchen. Only 10 minutes from downtown Winchester and convenient to grocery, farmers’ markets, and the hospital. House is full of character and has an open floor plan! The spacious family room has hardwood floors, a wood beam and brick surround fireplace. Eat-in-kitchen and large master bathroom. Unfinished basement offers an abundance of possibilities .
Highlights
(ACTIVE)
Summary
- Full Bathrooms: 2
- Appliances: Cooktop, Dishwasher, Exhaust Fan, Oven
- Basement: Yes
- Flooring Type: Ceramic Tile, Laminate Plank, Hardwood, Laminated
- Total Bedroom Count: 3
- Parking: Gravel Driveway, Driveway
- View: Trees/Woods, Mountain(s), Pasture
- Exterior: Outbuilding(s)
- Architectural Style: Ranch/Rambler
- Heating: Heat Pump
- Cooling: Central Air
- List Price: $395,000
- Price/SqFt: $235
- Annual Tax Amount: $542
- Tax Year: 2024
- Directions: Located off 522 North on Chestnut Grove Road.
- Year Built: 1987
- Stories: 2
- Living Area: 1,680 SqFt
- Lot Size: 5 Acres
- MLS Number: VAFV2034530
- MLS Name: BRIGHT
- Office Name: MarketPlace REALTY
- Office Phone: (540) 450-2747
- Office Email: contactus@mympr.com
- Listing Agent: Emma Catherine Kerns
- Agent Phone: (540) 762-9492
- Agent Email: emma@mympr.com
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Last updated on: 8/2/2025, 8:45:32 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Price information
Property sales
| Date | Event | Price |
|---|---|---|
| Apr 22, 2010 | Home Sold | $73,000 |
| Jan 16, 2007 | Home Sold | $268,500 |
| Jun 28, 2006 | Home Sold | $145,000 |
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2024 | $212,700 | $542 |
| 2023 | $212,700 | $1,084 |
| 2022 | $176,500 | $1,076 |
| 2021 | $176,500 | $1,076 |
| 2020 | $176,300 | $1,075 |
| 2019 | $176,300 | $966 |
| 2018 | $158,400 | $966 |
| 2017 | $158,400 | $950 |
History based on county public records data.
Nearby schools
2
Gainesboro Elementary School
Public District PK-5
2.4 mi
•4651 N Frederick Pike
5
Indian Hollow Elementary School
Public District PK-5
5.3 mi
•1548 N Hayfield Rd
3
Apple Pie Ridge Elementary School
Public District PK-5
6.5 mi
•349 Apple Pie Ridge Rd
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $57,632. The most common annual income of people living in Winchester, VA is between $35k-100k. Most families are married, no kids. Typical level of education for residents in this area is high school diploma.
How much money do the neighbors make?
What level of education do the neighbors have?
What types of families live nearby?
Are the neighbors home owners or renters?
How old are people in this area?
What do the neighbors do for fun?
Hunting
Figure Skating
NASCAR
Where do the neighbors shop?
Dick's Sporting Goods
Dillards
Wal-Mart
Where do the neighbors go to eat?
Texas Roadhouse
Cracker Barrel
Hardee's
What do the neighbors drive?
Subaru
Cadillac
Ram
What do the neighbors listen to?
New Country
News/Talk/Information
Classic Country
Frequently asked questions
About 1399 Chestnut Grove Rd
The listing price of 1399 Chestnut Grove Rd property is $395,000.
The property 1399 Chestnut Grove Rd is a house located in Winchester, Virginia, 22603.
Active Listing: 1399 Chestnut Grove Rd is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 1399 Chestnut Grove Rd are: Gainesboro Elementary School (GreatSchools Rating 2/10), Indian Hollow Elementary School (GreatSchools Rating 5/10), Apple Pie Ridge Elementary School (GreatSchools Rating 3/10), Frederick County Middle School (GreatSchools Rating 2/10), James Wood Middle School (GreatSchools Rating 3/10), Mountain Ridge Middle School (GreatSchools Rating 3/10), James Wood High School (GreatSchools Rating 5/10), John Handley High School (GreatSchools Rating 3/10), Millbrook High School (GreatSchools Rating 4/10).
According to the records, the last property tax for 2024 is $542 (source: MLS/based on county public records data).
The last sale was on April 22, 2010 for $73,000 (source: MLS/tax record).
The property at 1399 Chestnut Grove Rd has 3 bedrooms and 2 bathrooms.
The property 1399 Chestnut Grove Rd is 1,680 SqFt (source: MLS/tax record).
The year of construction for 1399 Chestnut Grove Rd is 1987.
This home is located at 1399 Chestnut Grove Rd in Winchester, VA and zip code 22603. This 1,680 square foot home, which was built in 1987, sits on a 5.00 acre lot. Features: 3 bedrooms, 2 bathrooms. It has been listed on Rocket Homes since August 1, 2025 and is currently priced at $395,000.
In July 2025 in Winchester, VA there were 54.6% more homes for sale than in June. In July 2025 median list price was $465,000 and the average listing age was 71 days.