OFF MARKET

Off market mar 2022 for $505K

$601,541

Est. refi paymentEst. refi $3,376/mo

•

2,463

sq ft

299 Chestnut Trail Rd, Front Royal, VA 22630

About this home

All offers deadline by Monday Feb 28 5pm!! Please attach High Knobs Owners' Association Addendum located in the documents to all offers. The "HOA" fees of $671 are listed as a special tax in the tax record and are part of the real estate taxes. Please see use "Information for Making an Offer" in Documents section. * * BEAUTIFUL log home on private 3.25 acres w/ winter views * * All of this is located in the gated community of High Knob which access to the Appalachian Trail, community swimming pool, and clubhouse * * Hardwood floors, stone wood-burning fireplace & woodstove, many upgrades , kitchen island, double decks, screened porch, paved drive, workshop in huge garage, main lvl master, 2 huge walk-ins * * The oak floors throughout the main and upper levels and cork flooring on lower level * * Roof 2011, HVAC installed 2016 * * Updates include brand new carpet in the main floor primary suite. The dishwasher, water heater, and built-in microwave are all less than 2 years old. Total finished 2462sq * * The septic pumped 2021

Single-familyProperty Type

2001Year Built

3.25 acresLot Size

$244Est. Price/Sq.Ft.

2 car garageParking

Listed by Jin Kim • Mega Realty & Investment Inc

•703-642-6342 (broker)

•megarealty@gmail.com (broker)

Bought with Holly McCaffrey • Berkshire Hathaway HomeServices PenFed Realty

•540-722-9300 (broker)

•winchester@penfedrealty.com (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #VAWR2002348

Redfin Estimate

$601,541

$97K since sold in March 2022$5,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 13.3% higher than the average sale price ($531K) of 6 comparable homes.

SOLD SEP 28, 2026
$394,900
A
3 beds2.5 baths2,146 sq ft
142 Lazy Livin Ln, Front Royal, VA 22630
BOUGHT WITH REDFIN MAY 11, 2026
$375,000
B
3 beds3 baths2,280 sq ft
806 Windy Way, Front Royal, VA 22630
SOLD JUN 26, 2026
$595,000
C
3 beds2 baths2,700 sq ft
2622 Ccc Rd, Linden, VA 22642
SOLD JUN 30, 2026
$729,900
D
4 beds3.5 baths3,240 sq ft
623 Shenandoah Valley Dr, Front Royal, VA 22630
SOLD MAY 7, 2026
$585,000
E
3 beds3 baths2,255 sq ft
241 Lazy Livin Ln, Front Royal, VA 22630
SOLD JUN 18, 2026
$505,000
F
3 beds3 baths2,488 sq ft
703 Cardinal Dr, Front Royal, VA 22630

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$195,928

Est. take-home

List your home with Redfin and save $6,015

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,505/mo

Redfin rental estimate

List your home for rent

Market trends in 22630, VA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.7%

0.3% MoM

Median sale price

$400K

$12K MoM

Avg. days on market

53d

8 days MoM

Recently sold homes

128

35 MoM

New listings for sale

NEW 6 HRS AGO
$292,000
2 beds1 bath1,272 sq ft
38 S Marshall St, Front Royal, VA 22630
(480) 462-5392
OPEN SAT, 11AM TO 1PM
$589,000
3 beds3 baths2,722 sq ft
337 Chestnut Trail Rd, Front Royal, VA 22630
(540) 348-4911
COMING SOON
$370,000
4 beds3 baths2,145 sq ft
405 Warren Ave, Front Royal, VA 22630
(703) 679-1700
$649,900
4 beds3 baths2,652 sq ft
3823 Panhandle Rd, Front Royal, VA 22630
(703) 771-8888
$249,900
3 beds1.5 baths1,518 sq ft
208 E 16th St, Front Royal, VA 22630
(877) 328-4400
$395,000
3 beds2 baths1,310 sq ft
411 Cardinal Dr, Front Royal, VA 22630
(571) 386-1075
$469,900
3 beds2 baths1,600 sq ft
515 Red Bud Ln, Front Royal, VA 22630
(540) 635-4900
$430,000
3 beds3 baths1,674 sq ft
1170 Kesler Rd, Front Royal, VA 22630
(540) 465-3771
COMING SOON
$445,000
3 beds3 baths2,130 sq ft
298 Honey Farm Ln, Front Royal, VA 22630
(703) 378-8810
COMING SOON
$599,000
3 beds3 baths2,345 sq ft
189 Hobbs Knob Rd, Front Royal, VA 22630
(855) 450-0442
See all

Provided by Redfin

Sale history for 299 Chestnut Trail Rd

Date

Event

Price

BRIGHT MLS #VAWR2002348

Mar 23, 2022

Sold

$505,000

$205/sq ft

Feb 28, 2022

Pending

—

Feb 28, 2022

Price Changed

$489,900

$199/sq ft

Feb 26, 2022

Listed

$489,000

$199/sq ft

Public Records

Aug 5, 2021

Sold

$453,500

$184/sq ft

BRIGHT MLS #VAWR143854

Aug 4, 2021

Pending

—

Aug 4, 2021

Sold

$453,500

$184/sq ft

Jul 10, 2021

Contingent

—

Jul 10, 2021

Listed

$450,000

$183/sq ft

Jul 9, 2021

Sold

$453,500

$184/sq ft

Jun 10, 2021

Pending

—

Jun 3, 2021

Listed

$450,000

$183/sq ft

+35

Looking for the charm of a log home on a private lot in a community that is conveniently located to everything? Welcome to 299 Chestnut Trail Rd! This gorgeous home is nestled on over 3 acres of natural beauty complete with walking trails. Relax on one of the many porches or settle in around the stone fireplace that serves as an eye-catching centerpiece. This home boasts two primary suites complete with full baths and huge walk-in closets. The oak floors throughout the main and upper levels and cork flooring on the lower level create a warm, comforting feel. The lower level is plumbed for a wet bar or potential kitchen and has a wood stove for those cold winter days. It also contains a large bonus room that would make a great playroom, home gym, or rec room. A covered breezeway connects the spacious garage to the home for additional storage or tinkering space. Updates include brand new carpet in the main floor primary suite. The dishwasher, water heater, and built-in microwave are all less than a year old. The HVAC was installed in 2016 and has a whole-house humidifier. All outer areas recently stained. All of this is located in the gated community of High Knob which has its own access to the Appalachian Trail, community swimming pool, and clubhouse. Here’s your chance to live where most people can only escape to once in a while.

Join or sign in to view all info

Year

Property tax

Land + Additions

Assessment*

2026

$3,530 (+18.8%)

$79,100 + $541,300

$620,400

2025

$2,972 (+5.7%)

$79,100 + $541,300

$620,400

2024

$2,813 (+8.2%)

$86,300 + $444,400

$530,700

2023

$2,600 (+8.1%)

$86,300 + $444,400

$530,700

2022

$2,406

$86,300 + $444,400

$530,700

2021

$2,406

$75,000 + $292,400

$367,400

2020

$2,406

$75,000 + $292,400

$367,400

2019

$2,406 (+21.2%)

$75,000 + $292,400

$367,400

2018

$1,986 (+1.6%)

$75,000 + $225,900

$300,900

2017

$1,955 (+4.8%)

$75,000 + $225,900

$300,900

2016

$1,865 (−17.5%)

$75,000 + $225,900

$300,900

2014

$2,261

$77,500 + $293,200

$370,700

Tax history for 299 Chestnut Trail Rd

Year

Property tax

Land + Additions

Assessment*

2026

$3,530 (+18.8%)

$79,100 + $541,300

$620,400

2025

$2,972 (+5.7%)

$79,100 + $541,300

$620,400

2024

$2,813 (+8.2%)

$86,300 + $444,400

$530,700

2023

$2,600 (+8.1%)

$86,300 + $444,400

$530,700

2022

$2,406

$86,300 + $444,400

$530,700

2021

$2,406

$75,000 + $292,400

$367,400

2020

$2,406

$75,000 + $292,400

$367,400

2019

$2,406 (+21.2%)

$75,000 + $292,400

$367,400

2018

$1,986 (+1.6%)

$75,000 + $225,900

$300,900

2017

$1,955 (+4.8%)

$75,000 + $225,900

$300,900

2016

$1,865 (−17.5%)

$75,000 + $225,900

$300,900

2014

$2,261

$77,500 + $293,200

$370,700

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

3.5

Stories

1.3

Lot width

—

Lot depth

—

Lot size

3.25 Acres

Year renovated

2011

Sq. Ft.

2,052

Year built

2001

Style

Single Family Residential

County

Warren County

APN

31B1 8 V 33A

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 10, 2026.

Property details

Parking

Parking Information
# of Detached Garage Spaces: 2
Garage Features: Garage - Front Entry
# of Total Garage and Parking Spaces: 2
Has Garage
# of Garage Spaces: 2
Detached Garage

Interior

Bedroom Information
# of Bedrooms On 1st Upper Level: 1
# of Bedrooms On Main Level: 1
# of Bedrooms On 1st Lower Level: 1

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 1
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Full) On 1st Lower Level: 1
# of Bathrooms (Full) On All Upper Levels: 1
# of Bathrooms (Full) On All Lower Levels: 1
# of Bathrooms (Half): 1
# of Bathrooms (Full): 3

Interior Information
Living Area Sq.Ft. Source: Estimated

Fireplace Information
# of Fireplaces: 1

Basement Information
Basement: Yes
Fully Finished

Exterior

Property Information
Total Below Grade Sq. Ft.: 1368
Improvement Assessed Value: $292,400
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Construction Materials: Log
Foundation Details: Wood
Other Structures: Above Grade, Below Grade
Structure Type: Detached

Pool Information
Community Pool

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $75,000

Above Grade Information
Finished Sq.Ft.: 1,779
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft.: 684
Unfinished Sq.Ft. Source: Estimated
Finished Sq.Ft.: 684
Finished Sq.Ft. Source: Estimated

Financial

Tax Information
County Tax: $2,406
Tax Assessed Value: $367,400
Tax Year: 2021
Tax Annual Amount: $2,829

Assessments Information
Year Assessed: 2021

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: On Site Septic
Water Source: Public

Location

Homeowners Association Information
HOA Fee: $671
HOA Fee Frequency: Annually

School Information
School District Name: WARREN COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent

Location Information
Outside City Limits
Directions: * *

Public facts

Beds: 1
Baths: 3.5
Sq. Ft.: 2,052
Stories: 1.3
Lot Size: 3.25 acres
Style: Single Family Residential
Year Built: 2001
Year Renovated: 2011
County: Warren County
APN: 31B1 8 V 33A

Home facts updated by county records on Aug 10, 2026

Around this home

Schools

Hilda J. Barbour Elementary School

Public PreK-5 • Assigned • 3.5mi

6/10

New Warren County Middle School

Public 6-8 • Assigned • 3.2mi

5/10

Warren County High School

Public 9-12 • Assigned • 3.5mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.31% chance of being in a wildfire in next 30 years

3/10 Heat Factor

1 days above 101° expected this year, 1 days in 30 years

2/10 Wind Factor

2% chance of strong winds in next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Front Royal, VA • 22630

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.9 hours in June and 3.9 hours in December, placing it below the U.S. average for solar exposure.

8.9 hrs

3.9 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$572,000 – $692,000

Reach more buyers when you sell with Redfin. Save up to $6,015 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

$29,900

Land— sq ft

Rome Beauty Dr, Linden, VA 22642

(703) 669-0099

$485,000

3 beds2 baths1,590 sq ft

1336 Granny Smith Rd, Linden, VA 22642

(703) 383-3245

$431,000

3 beds3 baths2,814 sq ft

542 Jonathan Rd, Linden, VA 22642

(480) 462-5392

$415,000

3 beds2 baths1,628 sq ft

286 Oregon Hollow Rd, Linden, VA 22642

(540) 635-0400

$404,900

3 beds2 baths1,356 sq ft

1208 Devin Ct, Front Royal, VA 22630

(703) 378-8810

$419,999

4 beds3 baths2,094 sq ft

186 Apple Orchard Dr, Linden, VA 22642

(540) 259-4090

New listings for sale in 22630

NEW 6 HRS AGO

$292,000

2 beds1 bath1,272 sq ft

38 S Marshall St, Front Royal, VA 22630

(480) 462-5392

OPEN SAT, 11AM TO 1PM3D WALKTHROUGH

$589,000

3 beds3 baths2,722 sq ft

337 Chestnut Trail Rd, Front Royal, VA 22630

(540) 348-4911

COMING SOON

$370,000

4 beds3 baths2,145 sq ft

405 Warren Ave, Front Royal, VA 22630

(703) 679-1700

$649,900

4 beds3 baths2,652 sq ft

3823 Panhandle Rd, Front Royal, VA 22630

(703) 771-8888

$249,900

3 beds1.5 baths1,518 sq ft

208 E 16th St, Front Royal, VA 22630

(877) 328-4400

$395,000

3 beds2 baths1,310 sq ft

411 Cardinal Dr, Front Royal, VA 22630

(571) 386-1075

$469,900

3 beds2 baths1,600 sq ft

515 Red Bud Ln, Front Royal, VA 22630

(540) 635-4900

$430,000

3 beds3 baths1,674 sq ft

1170 Kesler Rd, Front Royal, VA 22630

(540) 465-3771

COMING SOON

$445,000

3 beds3 baths2,130 sq ft

298 Honey Farm Ln, Front Royal, VA 22630

(703) 378-8810

Home values near 299 Chestnut Trail Rd

Data from public records.

Address	Redfin Estimate
157 Chestnut Trail Rd, Front Royal, VA 2 Beds \| 2.5 Baths \| 2592 Sq. Ft.	$493,361
310 Chestnut Trail Rd, Front Royal, VA 3 Beds \| 3 Baths \| 2612 Sq. Ft.	$531,558

Address	Redfin Estimate
240 Chestnut Trail Rd, Front Royal, VA 4 Beds \| 3 Baths \| 2509 Sq. Ft.	$551,390
206 Chestnut Trail Rd, Front Royal, VA 4 Beds \| 3 Baths \| 2178 Sq. Ft.	$560,204

Address	Redfin Estimate
332 Chestnut Trail Rd, Front Royal, VA 3 Beds \| 3 Baths \| 1440 Sq. Ft.	$486,493
223 Chestnut Trail Rd, Front Royal, VA 3 Beds \| 3 Baths \| 2742 Sq. Ft.	$559,623

Property information provided by BRIGHT MLS when last listed in 2022. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Front Royal	Agents near me	Richmond, VA homes for sale	Front Royal Housing Market
Houses for sale near me	Arlington, VA homes for sale	McLean, VA homes for sale
Land for sale near me	Alexandria, VA homes for sale	Chesapeake, VA homes for sale
Open Houses near me	Virginia Beach, VA homes for sale	Front Royal Property Records
Condos for sale near me	Fairfax, VA homes for sale	VA New Listings

Winchester homes for sale
Berryville homes for sale
Stephens City homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 22630, VA

Sale history for 299 Chestnut Trail Rd

Tax history for 299 Chestnut Trail Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 22630

Home values near 299 Chestnut Trail Rd

More real estate resources