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$589,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 3,303 Sq. Ft.
  • 2 Car Garage
  • Updated 17 hours ago

Next open house:

Open House: 11:00 AM - 1:00 PM

Saturday 10/3 11:00 AM - 1:00 PM

337 Chestnut Trail Road,Front Royal, VA 22630

337 Chestnut Trail RoadFront RoyalVA22630

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This beautiful chalet sits on 2.5 private, park-like acres with a large usable yard, seasonal mountain views, and plenty of space to enjoy the outdoors. And while the setting is beautiful, there's just as much to love inside. The kitchen has been completely reimagined with beautiful custom cabinetry, granite countertops, a large center island, newer appliances, and tile flooring that continues into the dining room. The great room has all the character you want in a chalet, with soaring wood ceilings, a wall of windows, and a stone gas fireplace. The windows fill the room with natural light and bring the outdoors right into the living space. And there's a nice surprise beneath the carpet in the living room and hallway. Hardwood floors are already in place underneath. There are two bedrooms and an updated full bath on the main level, while the upper level is home to the primary suite. The primary bath has also been beautifully updated with a large walk-in shower, extra-deep soaking tub, and double-sink vanity. The finished walkout lower level feels like a living space of its own, with large windows that bring in plenty of natural light, a full bath, surround sound, and walk-in access directly from the two-car garage. There's also a bonus room that would make a great home office, hobby room, or other flex space. It's a great setup for guests, extended family, entertaining, or simply having a separate place to spread out. Outside, there's plenty of room to enjoy the natural surroundings and privacy of 2.5 acres, whether you envision a garden, space for the dogs to run, or simply a quiet place to unwind. The large deck offers both covered and open areas for enjoying the setting and seasonal mountain views. Some of the most important updates aren't necessarily the glamorous ones. The roof was replaced in 2017 with 50-year shingles, and the home also has a Bosch HVAC system, 100-gallon hybrid water heater, and Cummins whole-house generator. These are big-ticket improvements that are nice to know are already in place. And of course, you'll have all the benefits of living in the gated community of High Knob, with a community pool, clubhouse, tennis and pickleball courts, playground, walking trails, private access to the Appalachian Trail, and more.

Full Property Details for 337 Chestnut Trail Rd

General

  • Price: $589,000
  • Taxes: $3,919 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAWR2015592
  • Updated: 10/2/2026
  • Added to Site: 1 day(s) ago

Interior

  • Interior Features: Family Room Off Kitchen, Kitchen - Island, Primary Bath(s), Pantry, Recessed Lighting, Upgraded Countertops
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Stone
  • Appliances: Built-In Microwave, Dishwasher, Refrigerator, Stove

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 1
  • Main - Full Baths: 1
  • Lower Floor Baths: 1
  • Lower - Full Baths: 1

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 1
  • Bedrooms Main & Up: 2

Additional Information

  • Shared Amenities: Basketball Courts, Club House, Common Grounds, Community Center, Gated Community, Jog/Walk Path, Meeting Room, Party Room, Picnic Area, Pool - Outdoor, Tennis Courts, Tot Lots/Playground
  • Shared Pool: Yes
  • Pool: Yes

Exterior

  • Porch/Patio/Deck: Deck(s), Porch(es), Wrap Around

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Features: Asphalt Driveway
  • Parking Type: Attached Garage
  • Garage Description: Garage - Side Entry

Location

  • County: WARREN
  • Subdivision: HIGH KNOB
  • Driving Directions: Enter the community from High Knob Rd not Massanutten Mountain Rd which some GPS systems will try to utilize. Gated Community. You will need an agent to give you access.

School Information

  • School District: Warren County Public Schools
  • Elementary School: Hilda J. Barbour
  • Middle School: Warren County High School
  • High School: Warren County

Community

  • Assoc. Fees Include: Common Area Maintenance, Pool(s), Recreation Facility, Road Maintenance, Security Gate, Snow Removal

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Septic = # of BR
  • Water: Public

Structural Information

  • Architectural Style: Chalet
  • Structure Type: Detached
  • Construction: Cedar
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Fully Finished, Garage Access, Interior Access, Outside Entrance
  • Foundation: Concrete Perimeter
  • Roof: Architectural Shingle
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 3,303
  • Sq. Ft. Source: Estimated
  • Living Area: 2,722 Sq. Ft.
  • Finished Above Grnd: 1,851 Sq. Ft.
  • Finished Below Grnd: 871 Sq. Ft.
  • Year Built: 2001
  • Year Built Source: Estimated
  • Property Condition: Excellent

Unit Information

Unit 1

  • Bathrooms-Lower: 1

Lot Features

  • Lot Size (Acres): 2.51
  • Lot Size (Sq. Ft.): 109,336
  • Lot Size Source: Estimated
  • Street/Road Desc.: Paved
  • Zoning: R

Financial Considerations

  • Price Per Sq. Ft.: $318.21
  • Assessment Year: 2025
  • County Tax: $3,190
  • County Tax Freq: Annually
  • Tax w/Assessment: $560,700
  • Tax Amount: $3,919
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple

Listed by Samson Properties, Lori Oaks

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Listing agent

— 337 Chestnut Trail Rd —

  • Lori Oaks

    Samson Properties

Listing Office Email: dsamson@samsonproperties.net

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 337 Chestnut Trail Rd

School District:Warren County Public Schools
NameGradesDistance
Hilda J. Barbour Elementary School
290 Westminster Drive, Front Royal, VA 22630
PK-53.6 mi
New Warren County Middle School
522 Heritage Drive, Front Royal, VA 22630
6-83.2 mi
Warren County High School
155 Westminster Drive, Front Royal, VA 22630
9-123.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 337 Chestnut Trail Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/01/2026
Listed
$589,000
86.98%
MLS
10/07/2014
Sold
$315,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 337 Chestnut Trail Rd

Year
Property Taxes
Change
Tax Assessment
Change
2026
$3,190
19%
$560,700
—
2025
$2,686
-2%
$560,700
8%
2024
$2,741
-47%
$517,100
—
2022
$5,171
63%
$517,100
41%
2022
$3,167
3%
$365,500
—
2020
$3,061
1%
$365,500
—
2019
$3,045
12%
$365,500
16%
2018
$2,715
3%
$315,200
-3%
2016
$2,645
—
$326,600
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 337 Chestnut Trail Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Samson Properties, Lori Oaks

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337 Chestnut Trail Road, Front Royal, VA 22630 (MLS# VAWR2015592) is a Single Family property with 3 bedrooms and 3 full bathrooms. 337 Chestnut Trail Road is currently listed for $589,000 and was received on October 01, 2026. Want to learn more about 337 Chestnut Trail Road? Do you have questions about finding other Single Family real estate for sale in Front Royal? You can browse all Front Royal real estate or contact a Coldwell Banker agent to request more information.

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