1399 Chestnut Grove Road
Description
- Listed by: Emma Catherine Kerns 540.762.9492 emma@mympr.com • MarketPlace REALTY
Recent comparable sales
Median sold price
$420,000
Avg days on market
22
Sale-to-list ratio
98.4%
Winchester, VA
9 comparable properties found
$345,000
Sold 12/08/25
- 3
- Bedrooms
- 2
- Bathrooms
- 1,674
- Square Feet
- 2.67
- Acres
$400,000
Sold 10/24/25
- 3
- Bedrooms
- 2
- Bathrooms
- 1,721
- Square Feet
- 5.01
- Acres
$536,000
Sold 12/17/24
- 3
- Bedrooms
- 2
- Bathrooms
- 1,616
- Square Feet
- 5.04
- Acres
$420,000
Sold 09/22/25
- 3
- Bedrooms
- 2
- Bathrooms
- 1,728
- Square Feet
- 5.58
- Acres
$299,000
Sold 11/21/25
- 3
- Bedrooms
- 1
- Bathrooms
- 1,947
- Square Feet
- 5
- Acres
$465,000
Sold 11/20/24
- 3
- Bedrooms
- 3
- Bathrooms
- 1,960
- Square Feet
- 5
- Acres
$400,000
Sold 09/21/26
- 3
- Bedrooms
- 3
- Bathrooms
- 1,745
- Square Feet
- 2.68
- Acres
Location
Sold By Spring Hill Real Estate, LLC.
$2,065 per month
30 year fixed, 7.03% Interest
$1,975
$90
$0
1Property Information for 1399 Chestnut Grove Road
Property Details
- Taxes: $1,077 / year
- MLS Type: Residential / Fee Simple
- County: Frederick County, VA
- Tax ID Number: 20 3 9
- Ownership: Fee Simple
- Condo Coop Association: No
- HOA: No
- Structure Type: Detached
- Style: Ranch/Rambler
- Levels/Stories: 2
- Waterfront: No
- Views: Trees/Woods, Mountain, Pasture
- Garage: No
- Subdivision: THREE CREEK KNOLLS
- Subdivision: THREE CREEK KNOLLS (FREDERICK VA)
- Legal Subdivision: THREE CREEK KNOLLS
- Central Air: Yes
- Basement: Yes
- Above Grade Finished SQFT: 1,680.00
- Above Grade Fin SQFT Source: Estimated
- Below Grade Finished SQFT: .00
- Below Grade Fin SQFT Source: Assessor
- Below Grade Unfinished SQFT: .00
- Below Grade Unfin SQFT Source: Assessor
- Total Below Grade SQFT: .00
- Total Below Grade SQFT Source: Assessor
- New Construction: No
Building Information
- Stories: 2
- Year Built: 1987
- Lot Size: 5.00 AC / 217,800 SF
Location
- In City Limits: No
- School District Name: FREDERICK COUNTY PUBLIC SCHOOLS
- School District County ID: 121140907577
- SchoolDistrictSource: Listing Agent
- County: FREDERICK
Waterfront / Water Access
- Water View: No
- Water Access: No
- Water Oriented: No
- Navigable Water: No
- Tidal Water: No
- Riparian Rights Y/N: No
Association / Community Info
- Senior Community: No
- Association Recreation Fee Y/N: No
Taxes and Assessment
- Tax Year: 2022
- Tax Assessed Value: $309,518
- Year Assessed: 2025
- County Tax: $1,077
- Improvement Assessed Value: $102,000
- Land Assessed Value: $101,000
- Clean Green Assessed: No
- Land Use Code: 2
- Zoning: RA
- Tax Lot: 9
- School Tax: $0
- Automatically Update Tax Values Y/N: Yes
Lease Information
- Pets Allowed: No
Rooms
- # Bedrooms Count Main Level: 3
- # Bathrooms Count Main Level: 2
- # Bathrooms Full Main Level: 2
- # Bathrooms Half Main Level: 0
- Stories: Main
Building Info
- Total Finished SQFT: 1,680.00
- Total Finished SQFT Source: Estimated
- Tax Total Finished SQFT: .00
- Total SQFT: 1,680.00
- Total SQFT Source: Estimated
- Construction Materials: Vinyl Siding
- Flooring Type: Ceramic Tile, Laminate Plank, Hardwood, Laminated
- Basement Type: Full
- Foundation Details: Wood
- Room and Floor: Bedrooms-Main Level-1, Bedrooms-Main Level-2, Bedrooms-Main Level-3, Bathrooms Full-Main Level-1, Bathrooms Full-Main Level-2
- # Bathrooms Full: 2
- # Bathrooms Half: 0
- Other Structure: Barn
Lot / Land Information
- Lot Size Source: Estimated
- Fencing: Board
- Parcel ID: 18772655
- Ground Rent Exists: No
Parking
- Type Of Parking: Driveway
- Parking Features: Gravel Driveway
Interior Features
- Fireplace: Yes
- Fireplaces Count: 1
- Appliances: Cooktop, Dishwasher, Exhaust Fan, Oven - Single
- Accessibility Features: None
Exterior Features
- Spa: No
- Exterior Features: Outbuilding(s)
- Outdoor Living Structures: Porch(es)
- Pool: No Pool
- Horse: Yes
- Horse Amenities: Paddock, Stable(s), Horses Allowed
Utilities
- Heating: Yes
- Cooling Type: Central A/C
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Electric
- Hot Water: Electric
- Water Source: Well
- Sewer Septic: On Site Septic
Property History for 1399 Chestnut Grove Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Jan 6, 2026 | Closed BRIGHT #VAFV2034530 | $370,000 | — |
| Nov 21, 2025 | Pending BRIGHT #VAFV2034530 | — | |
| Nov 21, 2025 | Active Under Contract BRIGHT #VAFV2034530 | — | |
| Oct 16, 2025 | Price Change BRIGHT #VAFV2034530 | $384,900 | — |
| Sep 16, 2025 | Listed (Active) BRIGHT #VAFV2034530 | — | |
| Sep 12, 2025 | Active Under Contract BRIGHT #VAFV2034530 | — | |
| Aug 28, 2025 | Price Change BRIGHT #VAFV2034530 | $389,000 | — |
| Aug 1, 2025 | Listed (Active) BRIGHT #VAFV2034530 | $395,000 | — |
| Jan 6, 2025 | Closed (Public Record) Public Record #1925857189 | $370,000 | +1.8% / yr |
| Nov 21, 2021 | Expired BRIGHT #VAFV164800 | — | |
| Oct 13, 2021 | Withdrawn BRIGHT #VAFV164800 | — | |
| Sep 21, 2021 | Pending BRIGHT #VAFV164800 | — | |
| Aug 29, 2021 | Price Change BRIGHT #VAFV164800 | $325,000 | — |
| Jul 14, 2021 | Listed (Active) BRIGHT #VAFV164800 | $350,000 | — |
| Jan 9, 2007 | Closed (Public Record) Public Record #281939063 | $268,500 | +196.6% / yr |
| Jan 9, 2007 | Closed BRIGHT #1009609026 | $268,500 | — |
| Oct 13, 2006 | Pending BRIGHT #1009609026 | — | |
| Oct 13, 2006 | Listed (Active) BRIGHT #1009609026 | $268,500 | — |
| Jun 16, 2006 | Closed (Public Record) Public Record #281932946 | $145,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 01/06/2026 | Closed BRIGHT #VAFV2034530 | $370,000 |
| 11/21/2025 | Pending BRIGHT #VAFV2034530 | — |
| 11/21/2025 | Active Under Contract BRIGHT #VAFV2034530 | — |
| 10/16/2025 | Price Change BRIGHT #VAFV2034530 | $384,900 |
| 09/16/2025 | Listed (Active) BRIGHT #VAFV2034530 | — |
| 09/12/2025 | Active Under Contract BRIGHT #VAFV2034530 | — |
| 08/28/2025 | Price Change BRIGHT #VAFV2034530 | $389,000 |
| 08/01/2025 | Listed (Active) BRIGHT #VAFV2034530 | $395,000 |
| 01/06/2025 | Closed (Public Record) Public Record #1925857189 | $370,000 +1.8% / yr |
| 11/21/2021 | Expired BRIGHT #VAFV164800 | — |
| 10/13/2021 | Withdrawn BRIGHT #VAFV164800 | — |
| 09/21/2021 | Pending BRIGHT #VAFV164800 | — |
| 08/29/2021 | Price Change BRIGHT #VAFV164800 | $325,000 |
| 07/14/2021 | Listed (Active) BRIGHT #VAFV164800 | $350,000 |
| 01/09/2007 | Closed (Public Record) Public Record #281939063 | $268,500 +196.6% / yr |
| 01/09/2007 | Closed BRIGHT #1009609026 | $268,500 |
| 10/13/2006 | Pending BRIGHT #1009609026 | — |
| 10/13/2006 | Listed (Active) BRIGHT #1009609026 | $268,500 |
| 06/16/2006 | Closed (Public Record) Public Record #281932946 | $145,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public records
1399 Chestnut Grove Road
Baths
2Total Finished SqFt
1,680 SqFtAbove Grade Finished SqFt
1,680 SqFtStories
1Lot Size
217,800 SqFtStyle
Mobile / Manufactured HomeSchools near 1399 Chestnut Grove Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 |
Rating | School | Distance |
|---|---|---|
Gainesboro Elementary School PublicPK to 5 | ||
Frederick County Middle School Public6 to 8 | ||
James Wood High School Public9 to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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Nearby home values
| Address | Sold price | Beds | Baths | Sqft | Lot (Sqft) |
|---|---|---|---|---|---|
This home: 1399 Chestnut Grove Road, Winchester, VA 22603 | $370,000 | 3 | 2 | 1,680 | 217,800 |
$249,900 | 3 | 2 | 1,512 | 217,800 | |
$228,000 | 3 | 3 | 1,826 | 217,800 | |
– | 3 | 1 | 1,456 | 130,680 | |
$189,900 | 3 | 2 | 1,592 | 225,641 | |
– | 3 | 2.5 | 2,464 | 217,800 | |
– | 3 | 2.5 | 2,830 | 217,800 | |
$328,199 | 3 | 3 | 2,180 | 217,800 | |
– | 2 | 1 | 720 | 848,984 | |
$650,000 | 5 | 4 | 3,356 | 221,720 | |
$399,900 | 3 | 2 | 2,248 | 217,800 | |
$259,000 | 3 | 4 | – | 223,898 | |
– | 3 | 2.5 | 2,335 | 435,600 | |
– | 3 | 2.5 | 1,954 | 219,978 | |
$440,000 | 2 | 3 | 4,448 | 5,620,982 | |
$260,000 | 3 | 3 | 2,164 | 217,800 |
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.
Listing Courtesy of MarketPlace REALTY
© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 01/12/2026 01:03 PM