Is Chester Gap, VA quiet?

As of early 2026, 100% of users say it's quiet

Is Chester Gap, VA dog-friendly?

As of early 2026, 100% of users say it's dog friendly

Is there wildlife in Chester Gap, VA?

As of early 2026, 100% of users say there's wildlife

Do kids play outside in Chester Gap, VA?

As of early 2026, 83% of users say kids play outside

Are yards well-kept in Chester Gap, VA?

As of early 2026, 83% of users say yards are well-kept

Is a car needed in Chester Gap, VA?

As of early 2026, 80% of users say car is needed

Does Chester Gap, VA show holiday spirit?

As of early 2026, 60% of users say there's holiday spirit

Would people walk alone at night in Chester Gap, VA?

As of early 2026, 60% of users say people would walk alone at night

Do residents of Chester Gap, VA plan to stay at least 5 years?

As of early 2026, 50% of users say they plan to stay for at least 5 years

Is parking easy in Chester Gap, VA?

As of early 2026, 50% of users say parking is easy

Are neighbors friendly in Chester Gap, VA?

As of early 2026, 43% of users say neighbors are friendly

Is Chester Gap, VA walkable to restaurants?

As of early 2026, 29% of users say it's walkable to restaurants

Are there community events in Chester Gap, VA?

As of early 2026, 20% of users say there are community events

Are the streets well-lit in Chester Gap, VA?

As of early 2026, 17% of users say streets are well-lit

What is 81 Headwaters Rd estimated to be worth?

Trulia's estimated value for 81 Headwaters Rd in Chester Gap, VA is $450,300 .

What is the price history for 81 Headwaters Rd?

81 Headwaters Rd in Chester Gap, VA last sold for $279,900 in January 2019.

Is Chester Gap a buyer's or seller's market?

Chester Gap is currently a balanced market, based on recent for-sale activity.

What are the closest schools to 81 Headwaters Rd?

The closest schools to 81 Headwaters Rd in Chester Gap, VA are Rappahannock County Elementary School (Pre-K/Middle, rated 6/10), Rappahannock County High School (Middle, rated 5/10).

Does 81 Headwaters Rd have air conditioning?

Yes, 81 Headwaters Rd in Chester Gap, VA has air conditioning.

Does 81 Headwaters Rd have laundry facilities?

Yes, 81 Headwaters Rd in Chester Gap, VA has in-unit laundry.

OFF MARKET

$450,300

Trulia Estimate

3 Beds
2 Baths
1,872 sqft (on 1 acre)

81 Headwaters Rd, Chester Gap, VA 22623

Est. Refi. Payment $2,705/mo*

Refinance Your Home

Currently Off Market - Sold Jan 31, 2019 for $279,900

Home Value

Trulia Estimate

$450K

Since last month

$1K (-0.3%)

Since last year

$6K (+1.4%)

Since last sale

$170K (+60.6%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +72% in the last 10 years

Month	Estimated value
2026
September 2026	$450K
August 2026	$451K
July 2026	$455K
June 2026	$457K
May 2026	$461K
April 2026	$460K
March 2026	$454K
February 2026	$445K
January 2026	$426K
2025
December 2025	$436K
November 2025	$435K
October 2025	$435K
September 2025	$443K
August 2025	$441K
July 2025	$445K
June 2025	$434K
May 2025	$435K
April 2025	$434K
March 2025	$428K
February 2025	$425K
January 2025	$424K
2024
December 2024	$425K
November 2024	$421K
October 2024	$427K
September 2024	$425K
August 2024	$431K
July 2024	$431K
June 2024	$433K
May 2024	$437K
April 2024	$426K
March 2024	$423K
February 2024	$421K
January 2024	$408K
2023
December 2023	$410K
November 2023	$404K
October 2023	$403K
September 2023	$405K
August 2023	$404K
July 2023	$409K
June 2023	$408K
May 2023	$406K
April 2023	$405K
March 2023	$398K
February 2023	$390K
January 2023	$382K
2022
December 2022	$384K
November 2022	$390K
October 2022	$395K
September 2022	$396K
August 2022	$396K
July 2022	$399K
June 2022	$401K
May 2022	$403K
April 2022	$398K
March 2022	$393K
February 2022	$378K
January 2022	$374K
2021
December 2021	$376K
November 2021	$380K
October 2021	$380K
September 2021	$377K
August 2021	$377K
July 2021	$378K
June 2021	$382K
May 2021	$318K
April 2021	$314K
March 2021	$312K
February 2021	$312K
January 2021	$307K
2020
December 2020	$307K
November 2020	$305K
October 2020	$301K
September 2020	$300K
August 2020	$299K
July 2020	$298K
June 2020	$297K
May 2020	$297K
April 2020	$293K
March 2020	$292K
February 2020	$292K
January 2020	$291K
2019
December 2019	$290K
November 2019	$290K
October 2019	$295K
September 2019	$294K
August 2019	$292K
July 2019	$290K
June 2019	$288K
May 2019	$287K
April 2019	$285K
March 2019	$283K
February 2019	$281K
January 2019	$266K
2018
December 2018	$267K
November 2018	$267K
October 2018	$266K
September 2018	$270K
August 2018	$270K
July 2018	$287K
June 2018	$282K
May 2018	$267K
April 2018	$266K
March 2018	$265K
February 2018	$265K
January 2018	$265K
2017
December 2017	$273K
November 2017	$273K
October 2017	$271K
September 2017	$273K
August 2017	$284K
July 2017	$291K
June 2017	$294K
May 2017	$299K
April 2017	$261K
March 2017	$264K
February 2017	$263K
January 2017	$262K
2016
December 2016	$257K
November 2016	$255K
October 2016	$259K
September 2016	$262K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
438 Highridge Rd, Front Royal, VA	0.25	Single-Family Home	$315,000	10/22/25	3	2	1,304
147 Blue Ridge Ave, Chester Gap, VA	0.07	Single-Family Home	$400,000	07/15/26	4	3	2,912
7 Red Haven Ln, Chester Gap, VA	0.41	Single-Family Home	$395,000	12/08/25	3	2	1,448
600 Highridge Rd, Front Royal, VA	0.38	Single-Family Home	$485,000	07/14/26	3	2	1,420
175 Mountain Heights Rd, Front Royal, VA	0.43	Single-Family Home	$340,000	02/06/26	2	2	1,416
126 Locust Tree Ln, Front Royal, VA	0.46	Single-Family Home	$405,000	03/27/26	3	3	1,672
275 Mountain Heights Rd, Front Royal, VA	0.50	Single-Family Home	$366,000	10/07/25	2	1.5	2,100
227 Mountain Heights Rd, Front Royal, VA	0.46	Single-Family Home	$470,000	07/31/26	3	2.5	2,576
37 Headwaters Rd #41, Chester Gap, VA	0.14	Single-Family Home	$450,000	02/12/26	5	4	2,800
944 Highridge Rd, Front Royal, VA	0.76	Single-Family Home	$275,000	07/23/26	3	1.5	1,212

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.

Address	Distance	Price	Bed	Bath	Sqft	Status
147 Blue Ridge Ave, Chester Gap, VA 22623	0.07	$400,000	4	3	2,912	Recently Sold
37 Headwaters Rd #41, Chester Gap, VA 22623	0.14	$450,000	5	4	2,800	Recently Sold
60 Headwaters Rd, Chester Gap, VA 22623	0.13	$565,900	3	2.5	2,312	Off Market
144 Skyway Ln, Chester Gap, VA 22623	0.23	$347,900	3	2	2,208	Off Market
Lee Ridge Ln, Chester Gap, VA 22623	0.27	-	-	-	-	Off Market
Lot 27 Skyway Dr, Chester Gap, VA 22623	0.28	$436,600	3	2	1,400	Off Market
Highland Way, Chester Gap, VA 22623	0.29	-	-	-	-	Off Market
16 Headwaters Rd, Chester Gap, VA 22623	0.27	$304,000	2	2	1,000	Recently Sold
Headwaters Rd, Chester Gap, VA 22623	0.26	-	-	-	-	Off Market
130 Highland Way, Chester Gap, VA 22623	0.29	$460,000	3	3	3,000	Recently Sold
129 Skyway Ln, Chester Gap, VA 22623	0.30	$401,300	3	2	1,344	Off Market
128 Blue Ridge Ave, Chester Gap, VA 22623	0.31	$305,200	3	2	1,128	Off Market

Local Information

Map ViewExplore the area around 81 Headwaters Rd.
Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1988

1 acre lot

1,872 sqft

$241/sqft

About this House

This single-family home is located at 81 Headwaters Rd, Chester Gap, VA. 81 Headwaters Rd is in Chester Gap, VA and in ZIP code 22623. This property has 3 bedrooms, 2 bathrooms and approximately 1,872 sqft of floor space. This property has a lot size of 1 acre and was built in 1988.

81 Headwaters Rd, Chester Gap, VA 22623 is a 3 bedroom, 2 bathroom, 1,872 sqft single-family home built in 1988. It last sold for $279,900 on Jan 31, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $450,300, with a rent estimate of $2,372/month.

Home Details for 81 Headwaters Rd

Interior Features
Interior Details BasementNumber of Rooms: 7
Heating & Cooling Heating: Baseboard, Forced Air, Heat Pump, StoveAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility Stories: 1Floors: Carpet, Linoleum Vinyl
Appliances & Utilities DishwasherDryerRefrigeratorWasher
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: CompositionDeckExterior: WoodFoundation Type: Other
Parking & Garage Parking: None

Property Information
Year Built Year Built: 1988
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 1 acre

Price and Tax history

Date	Event	Price
Jan 31, 2019 Source: N/A	Sold	$279,900
Aug 8, 2018 Source: Agent Provided	PriceChange	$279,900 Price decreased by 3%
May 26, 2018 Source: Agent Provided	Listed For Sale	$289,900
Nov 11, 2017 Source: Agent Provided	ListingRemoved	$289,500
Aug 2, 2017 Source: Agent Provided	PriceChange	$289,500 Price decreased by 3%
May 10, 2017 Source: Agent Provided	Listed For Sale	$299,500

Year	Property tax	Tax assessment
2025	$2,088	$331,400

Additional Cost

Market trends in Chester Gap

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

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Available listings

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Around this home

Rappahannock County Elementary School
PK-7
Public
457 Students
Rappahannock County Public Schools
6/10
GreatSchools Rating
Parent Rating Average
I have had the same experience as the previous parent, as my child was in a very high performing Fairfax County school for kindergarten and first grade, before moving to Rappahannock County. She is now in 7th grade at RCES (the county is too small for a middle school!), and is very happy and successful. Her SOL grades are about as high as they can be, and she has a lot of expanded opportunities with the well-run gifted program. Also, the school has an excellent Farm-to-Table program, and has just renovated the courtyard to include experimental areas for plants and insects, as well as a new pottery kiln. They have also just built a new STEM/STEAM lab. The school is looking great! Our new superintendent is a real jewel.
Parent Review
6y ago
5 Reviews

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 Chester Gap

At least 3 Trulia users voted on each feature.

100 % Say it's quiet
100 % Say it's dog friendly
100 % Say there's wildlife
83 % Say kids play outside
83 % Say yards are well-kept
80 % Say car is needed
60 % Say there's holiday spirit
60 % Say people would walk alone at night
50 % Say they plan to stay for at least 5 years
50 % Say parking is easy
43 % Say neighbors are friendly
29 % Say it's walkable to restaurants
20 % Say there are community events
17 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.

Catkensho
Resident
6y ago
"Fire department events Halloween hayrides. Christmas party. Spring and fall events all fun! Applacisn trail "
0
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Catkensho
Resident
6y ago
"Rappahannock artisan trail, lots of wineries nearby. Fire department has events throughout the year. "
0
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Catkensho
Resident
8y ago
"It’s dog friendly but no leash law here. You must be careful to not let your dog run loose. There are bears and other critters. Fence your yard. "
1
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 81 Headwaters Rd

What is 81 Headwaters Rd estimated to be worth?
Trulia's estimated value for 81 Headwaters Rd in Chester Gap, VA is $450,300.
What is the price history for 81 Headwaters Rd?
81 Headwaters Rd in Chester Gap, VA last sold for $279,900 in January 2019.
Is Chester Gap a buyer's or seller's market?
Chester Gap is currently a balanced market, based on recent for-sale activity.
What are the closest schools to 81 Headwaters Rd?
The closest schools to 81 Headwaters Rd in Chester Gap, VA are Rappahannock County Elementary School (Pre-K/Middle, rated 6/10), Rappahannock County High School (Middle, rated 5/10).
Does 81 Headwaters Rd have air conditioning?
Yes, 81 Headwaters Rd in Chester Gap, VA has air conditioning.
Does 81 Headwaters Rd have laundry facilities?
Yes, 81 Headwaters Rd in Chester Gap, VA has in-unit laundry.

Apartments for Rent

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PET FRIENDLY
FURNISHED
$2,700/mo
2 bd
1 ba
Address Not Disclosed,
Front Royal, VA 22630
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Chester Gap
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Off Market Homes Near 81 Headwaters Rd

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SOLD
SEP 17, 2026
$325,000
3 bd
2 ba
1,776 sqft
1420 John Marshall Hwy,
Front Royal, VA 22630
Millennium Realty Group Inc.
SOLD
SEP 16, 2026
$369,000
3 bd
2 ba
1,056 sqft
641 Salt Lick Rd,
Front Royal, VA 22630
MarketPlace REALTY
SOLD
SEP 3, 2026
$329,000
2 bd
2 ba
1,490 sqft
1233 Summit Point Dr,
Front Royal, VA 22630
Samson Properties
SOLD
SEP 2, 2026
$399,999
3 bd
1.5 ba
1,728 sqft
205 Alpine Dr,
Front Royal, VA 22630
DMV Realty, INC.
SOLD
AUG 28, 2026
$600,000
4 bd
3 ba
2,952 sqft
17 Owens Ct,
Front Royal, VA 22630
Keller Williams Realty/Lee Beaver & Assoc.
SOLD
AUG 28, 2026
$265,000
2 bd
1.5 ba
1,200 sqft
8 Biggs Dr,
Front Royal, VA 22630
NextHome Realty Select
SOLD
AUG 27, 2026
$510,000
4 bd
3 ba
3,664 sqft
648 Creek Rd,
Front Royal, VA 22630
Long & Foster Real Estate, Inc.
SOLD
AUG 18, 2026
$379,000
2 bd
2 ba
1,120 sqft
180 Crest Ln,
Front Royal, VA 22630
Samson Properties
SOLD
AUG 11, 2026
$425,000
3 bd
2 ba
1,450 sqft
377 Windy Way,
Front Royal, VA 22630
Samson Properties
SOLD
AUG 7, 2026
$304,000
2 bd
2 ba
1,000 sqft
16 Headwaters Rd,
Chester Gap, VA 22623
Mint Realty
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Chester Gap
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Homes for sale near 81 Headwaters Rd

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0.5 ACRES
$369,900
4 bd
2 ba
2,304 sqft
115 Chester Gap Rd,
Chester Gap, VA 22623
Weichert Realtors - Blue Ribbon
1.41 ACRES
$385,000
3 bd
2.5 ba
2,208 sqft
28 High Spruce Rd,
Front Royal, VA 22630
Keller Williams Realty
1.68 ACRES
$474,900
4 bd
3 ba
2,514 sqft
4507 Remount Rd,
Front Royal, VA 22630
RLAH @properties
NEW CONSTRUCTION
1 ACRE
$509,900
3 bd
2 ba
1,420 sqft
Lot-85A Oriole Ct,
Front Royal, VA 22630
RE/MAX Real Estate Connections
NEW CONSTRUCTION
0.33 ACRES
$439,000
3 bd
2.5 ba
1,500 sqft
Apache Trl,
Chester Gap, VA 22623
Keller Williams Realty
NEW CONSTRUCTION
1.03 ACRES
$509,900
3 bd
2 ba
1,300 sqft
83A Oriole Ct,
Front Royal, VA 22630
RE/MAX Real Estate Connections
NEW CONSTRUCTION
0.8 ACRES
$509,900
3 bd
2 ba
1,520 sqft
Lot-83A Oriole Ct,
Front Royal, VA 22630
RE/MAX Real Estate Connections
3.25 ACRES
$410,000
4 bd
2 ba
1,808 sqft
673 Creek Rd,
Front Royal, VA 22630
United Real Estate Horizon
0.91 ACRES
$470,000
4 bd
3 ba
2,188 sqft
1033 Mountain Heights Rd,
Front Royal, VA 22630
Keller Williams Realty
1.12 ACRES
$500,000
4 bd
2.5 ba
1,568 sqft
15 Oak Heights Rd,
Front Royal, VA 22630
Pearson Smith Realty, LLC
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Chester Gap
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