37 Headwaters Rd, Chester Gap, VA 22623
OFF MARKET

$455,100

Trulia Estimate
  • 2 Beds
  • 1 Bath
  • 1,992 sqft (on 1.60 acres)

37 Headwaters Rd, Chester Gap, VA 22623

Est. Refi. Payment $2,616/mo*
Refinance Your Home

Home Value

Trulia Estimate
$455K
Since last month
Decreased$2K (-0.4%)
Since last year
Increased$278K (+157.1%)
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 +320% in the last 10 years
MonthEstimated value
2026
August 2026$455K
August 2026$455K
July 2026$457K
June 2026$460K
May 2026$457K
April 2026$455K
March 2026$452K
February 2026$450K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
37 Headwaters Rd #41, Chester Gap, VA
0.02
Single-Family Home
$450,000
02/12/26
5
4
2,800
20 Waterfall Rd, Chester Gap, VA
0.36
Single-Family Home
$318,000
11/21/25
2
1
1,092
147 Blue Ridge Ave, Chester Gap, VA
0.11
Single-Family Home
$400,000
07/15/26
4
3
2,912
438 Highridge Rd, Front Royal, VA
0.40
Single-Family Home
$315,000
10/22/25
3
2
1,304
7 Red Haven Ln, Chester Gap, VA
0.36
Single-Family Home
$395,000
12/08/25
3
2
1,448
275 Mountain Heights Rd, Front Royal, VA
0.63
Single-Family Home
$366,000
10/07/25
2
1.5
2,100
175 Mountain Heights Rd, Front Royal, VA
0.57
Single-Family Home
$340,000
02/06/26
2
2
1,416
1960 Zachary Taylor Hwy, Front Royal, VA
0.72
Single-Family Home
$210,000
03/23/26
2
1
1,390
16 Headwaters Rd, Chester Gap, VA
0.17
Single-Family Home
$304,000
08/07/26
2
2
1,000
224 Mountain Heights Rd, Front Royal, VA
0.61
Single-Family Home
$60,000
04/06/26
2
1
696

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
37 Headwaters Rd #41, Chester Gap, VA 22623
0.02
$450,000
5
4
2,800
Recently Sold
60 Headwaters Rd, Chester Gap, VA 22623
0.02
$560,200
3
2.5
2,312
Off Market
147 Blue Ridge Ave, Chester Gap, VA 22623
0.11
$400,000
4
3
2,912
Recently Sold
144 Skyway Ln, Chester Gap, VA 22623
0.20
$349,400
3
2
2,208
Off Market
16 Headwaters Rd, Chester Gap, VA 22623
0.17
$304,000
2
2
1,000
Recently Sold
128 Blue Ridge Ave, Chester Gap, VA 22623
0.19
$292,400
3
2
1,128
Off Market
Highland Way, Chester Gap, VA 22623
0.21
-
-
-
-
Off Market
130 Highland Way, Chester Gap, VA 22623
0.21
$460,000
3
3
3,000
Recently Sold
Highland Way, Chester Gap, VA 22623
0.23
-
-
-
-
Off Market
115 Chester Gap Rd, Chester Gap, VA 22623
0.21
$369,900
4
2
2,304
For Sale
Lot 27 Skyway Dr, Chester Gap, VA 22623
0.24
$439,000
3
2
1,400
Off Market
Headwaters Rd, Chester Gap, VA 22623
0.23
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 37 Headwaters Rd.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1978
1.6 acre lot
1,992 sqft
$228/sqft

About this House

2 homes on one lot. Live in one and have income from the other! Beautiful views 7 miles to Front Royal. Easy commute to I-66 Tenant can move with notice. Homes need a little work but well worth it at this price. Great investment!!
37 Headwaters Rd, Chester Gap, VA 22623 is a 2 bedroom, 1 bathroom, 1,992 sqft single-family home built in 1978. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $455,100, with a rent estimate of $1,826/month.

Home Details for 37 Headwaters Rd

Interior Features

Interior Details
BasementNumber of Rooms: 5
Heating & Cooling
Heating: Baseboard, WallAir ConditioningCooling System: WallHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Softwood
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: VinylFoundation Type: Concrete BlockPatio
Parking & Garage
Parking: None

Property Information

Year Built
Year Built: 1978
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 1.60 acres

Price and Tax history

DateEventPrice
Nov 23, 2017
Source: Agent Provided
ListingRemoved
$140,000
May 24, 2017
Source: Agent Provided
Listed For Sale
$140,000

Market trends in Chester Gap

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
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Around this home

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
    "Fire department events Halloween hayrides. Christmas party. Spring and fall events all fun! Applacisn trail "
    0
    Flag
  • Catkensho
    "Rappahannock artisan trail, lots of wineries nearby. Fire department has events throughout the year. "
    0
    Flag
  • Catkensho
    "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 37 Headwaters Rd

  • What is 37 Headwaters Rd estimated to be worth?
    Trulia's estimated value for 37 Headwaters Rd in Chester Gap, VA is $455,100.
  • Is Chester Gap a buyer's or seller's market?
    Chester Gap is currently a seller's market, based on recent for-sale activity.
  • What are the closest schools to 37 Headwaters Rd?
    The closest schools to 37 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 37 Headwaters Rd have air conditioning?
    Yes, 37 Headwaters Rd in Chester Gap, VA has air conditioning.
  • How big is the lot at 37 Headwaters Rd?
    The lot at 37 Headwaters Rd in Chester Gap, VA is about 1.6 acres.

Apartments for Rent

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Off Market Homes Near 37 Headwaters Rd

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