44 Headwaters Rd, Chester Gap, VA 22623
OFF MARKET

$277,700

Trulia Estimate
  • 2 Beds
  • 1 Bath
  • 1,208 sqft (on 11 acres)

44 Headwaters Rd, Chester Gap, VA 22623

Est. Refi. Payment $1,697/mo*
Refinance Your Home
Currently Off Market - Sold Aug 10, 2017 for $115,000

Home Value

Trulia Estimate
$278K
Since last month
Increased$6K (+2.3%)
Since last year
Increased$48K (+20.5%)
Since last sale
Increased$164K (+142.9%)
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 +39% in the last 10 years
MonthEstimated value
2026
September 2026$279K
August 2026$273K
July 2026$274K
June 2026$281K
May 2026$281K
April 2026$275K
March 2026$269K
February 2026$254K
January 2026$224K
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
20 Waterfall Rd, Chester Gap, VA
0.43
Single-Family Home
$318,000
11/21/25
2
1
1,092
16 Headwaters Rd, Chester Gap, VA
0.25
Single-Family Home
$304,000
08/07/26
2
2
1,000
438 Highridge Rd, Front Royal, VA
0.34
Single-Family Home
$315,000
10/22/25
3
2
1,304
224 Mountain Heights Rd, Front Royal, VA
0.57
Single-Family Home
$60,000
04/06/26
2
1
696
144 Hunter Ave, Chester Gap, VA
0.55
Single-Family Home
$215,000
06/05/26
2
1
768
1960 Zachary Taylor Hwy, Front Royal, VA
0.81
Single-Family Home
$210,000
03/23/26
2
1
1,390
7 Red Haven Ln, Chester Gap, VA
0.34
Single-Family Home
$395,000
12/08/25
3
2
1,448
175 Mountain Heights Rd, Front Royal, VA
0.52
Single-Family Home
$340,000
02/06/26
2
2
1,416
147 Blue Ridge Ave, Chester Gap, VA
0.02
Single-Family Home
$400,000
07/15/26
4
3
2,912
14 Summit Point Dr, Front Royal, VA
0.88
Single-Family Home
$200,000
06/23/26
2
1
610

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
0.02
$400,000
4
3
2,912
Recently Sold
37 Headwaters Rd #41, Chester Gap, VA 22623
0.07
$450,000
5
4
2,800
Recently Sold
60 Headwaters Rd, Chester Gap, VA 22623
0.08
$565,900
3
2.5
2,312
Off Market
144 Skyway Ln, Chester Gap, VA 22623
0.16
$347,900
3
2
2,208
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
128 Blue Ridge Ave, Chester Gap, VA 22623
0.22
$305,200
3
2
1,128
Off Market
Lot 27 Skyway Dr, Chester Gap, VA 22623
0.21
$436,600
3
2
1,400
Off Market
Highland Way, Chester Gap, VA 22623
0.23
-
-
-
-
Off Market
129 Skyway Ln, Chester Gap, VA 22623
0.23
$401,300
3
2
1,344
Off Market
16 Headwaters Rd, Chester Gap, VA 22623
0.25
$304,000
2
2
1,000
Recently Sold
Lee Ridge Ln, Chester Gap, VA 22623
0.24
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 44 Headwaters Rd.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1951
11 acre lot
1,208 sqft
$230/sqft

About this House

Very large lot offering a pond and breath taking views. 14.2372 acres per recent survey. The stucco home on property needs work or taken down to rebuild a new home. Motivated sellers! See to appreciate all this lot has to offer. Machine shed. Zoned Village residential. Which means you can build a home on 1 acre lots provided you meet road requirments, well and septic setbacks!
44 Headwaters Rd, Chester Gap, VA 22623 is a 2 bedroom, 1 bathroom, 1,208 sqft single-family home built in 1951. It last sold for $115,000 on Aug 10, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $277,700, with a rent estimate of $1,848/month.

Home Details for 44 Headwaters Rd

Interior Features

Heating & Cooling
Heating: Baseboard, Wall, ElectricHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Softwood
Interior Details
Number of Rooms: 5
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: StuccoFoundation Type: Stone
Parking & Garage
Parking: None

Property Information

Year Built
Year Built: 1951
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 11.00 acres

Price and Tax history

DateEventPrice
Aug 10, 2017
Source: N/A
Sold
$115,000
Jun 26, 2017
Source: Agent Provided
Pending
$115,000
May 24, 2017
Source: Agent Provided
Listed For Sale
$115,000
Aug 3, 2016
Source: Agent Provided
ListingRemoved
$180,000
Jan 12, 2016
Source: Agent Provided
Listed For Sale
$180,000

Market trends in Chester Gap

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

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 44 Headwaters Rd

  • What is 44 Headwaters Rd estimated to be worth?
    Trulia's estimated value for 44 Headwaters Rd in Chester Gap, VA is $277,700.
  • What is the price history for 44 Headwaters Rd?
    44 Headwaters Rd in Chester Gap, VA last sold for $115,000 in August 2017.
  • 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 44 Headwaters Rd?
    The closest schools to 44 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).
  • How big is the lot at 44 Headwaters Rd?
    The lot at 44 Headwaters Rd in Chester Gap, VA is about 11 acres.

Apartments for Rent

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Off Market Homes Near 44 Headwaters Rd

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