SOLD OCT 30, 2026

Sold on oct 2026

$415,000

•

1,714

sq ft

101 Charlton Rd, Winchester, VA 22602

Track this home’s value and nearby sales activity

About this home

NEW PRICE! Welcome to 101 Charlton Road, a charming 4-bedroom, 2.5-bath Cape Cod situated on a desirable corner lot. This well-maintained home features a main-level primary suite and beautiful hardwood floors throughout the main living areas. The spacious kitchen is equipped with stainless steel appliances, a center island, breakfast nook, and flows seamlessly into the separate dining room and inviting living room, perfect for everyday living and entertaining. Upstairs, you'll find three additional bedrooms, 1.5 baths, and the convenience of an upper-level laundry room. Enjoy outdoor living in the fenced backyard complete with a storage shed, rear deck, and plenty of space for pets, gardening, or gatherings. Relax on the welcoming covered front porch and enjoy the convenience of being just minutes from Historic Old Town Winchester, Shenandoah University, Winchester Medical Center, shopping, dining, local wineries, parks, and easy access to Routes 7, 50, and I-81 for commuting. All sizes are approximate.

Single-familyProperty Type

1998Year Built

$242Price/Sq.Ft.

$16/moHOA Dues

Listed by RoxAnn Grimes • RE/MAX Roots

•540-686-7362 (broker)

Bought with Bowen Murphy • Samson Properties

•703-378-8810 (broker)

•donnysamson@samsonpropeties.net (broker)

Bought with Jason Cheperdak • Samson Properties

•703-378-8810 (broker)

•donnysamson@samsonproperties.net (broker)

Redfin checked: a minute ago

•Source:BRIGHT MLS #VAFV2042768

Redfin Estimate

$416,164

$1,164 since sold in October 2026$21K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 9.1% lower than the average sale price ($458K) of 6 comparable homes.

SOLD SEP 18, 2026
$405,000
A
4 beds2 baths1,696 sq ft
116 Charlton Rd, Winchester, VA 22602
SOLD AUG 24, 2026
$393,000
B
4 beds2 baths1,838 sq ft
106 Plantation Dr, Winchester, VA 22602
SOLD JUL 29, 2026
$450,000
C
4 beds3 baths2,230 sq ft
107 Orchid Ct, Winchester, VA 22602
SOLD SEP 11, 2026
$470,000
D
4 beds3 baths2,366 sq ft
104 Foxglove Dr, Winchester, VA 22602
SOLD JUN 18, 2026
$553,847
E
4 beds2.5 baths2,400 sq ft
111 Old Wagon Rd, Winchester, VA 22602
SOLD MAY 22, 2026
$475,000
F
4 beds2.5 baths2,092 sq ft
228 Cavalry Dr, Winchester, VA 22602

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Market trends in 22602, VA

Last updated October 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

98.7%

0.3% MoM

Median sale price

$415K

$34K MoM

Avg. days on market

63d

3 days MoM

Recently sold homes

148

8 MoM

New listings for sale

$535,000
4 beds3.5 baths2,430 sq ft
500 Canyon Rd, Winchester, VA 22602
(540) 665-0360
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3 beds2 baths2,528 sq ft
170 Mount Vista Dr, Winchester, VA 22602
(540) 686-7362
$1,149,000
5 beds4.5 baths4,712 sq ft
1293 Gough Rd, Winchester, VA 22602
(703) 361-1188
OPEN NOV 21, 11AM TO 1PM
$465,000
3 beds2.5 baths2,122 sq ft
109 Harvard Dr, Winchester, VA 22602
(703) 669-0099
$524,900
4 beds2.5 baths3,262 sq ft
236 Asbury Rd, Winchester, VA 22602
(540) 665-0700
$205,000
3 beds2 baths1,333 sq ft
100 Buffalo Trl, Winchester, VA 22602
(888) 278-5840
OPEN SAT, 12PM TO 2PM
$549,000
4 beds2.5 baths3,284 sq ft
113 Teaberry Dr, Winchester, VA 22602
(540) 773-8475
COMING SOON
$419,900
4 beds3 baths3,160 sq ft
106 Country Club Cir, Winchester, VA 22602
(540) 662-0323
$1,459,000
5 beds4.5 baths4,336 sq ft
1074 Merrimans Ln, Winchester, VA 22602
(540) 662-0323
$600,000
6 beds4.5 baths4,050 sq ft
135 Mascouten St, Winchester, VA 22602
(540) 662-4500
See all

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Rental estimate

Est. $2,102 per month, based on comparable rentals

Redfin agents who toured

Charming Cape Cod-style home featuring a main-level bedroom with an adjoining full bath accessible from the hallway. Upstairs, one bedroom includes a private half bath, while the other two bedrooms share a full bath in the hallway.
4 months ago
Rachel Miller
Redfin Premier agent
236 deals

Sale and tax history for 101 Charlton Rd

Sale History
Tax History

Date

Event

Price

BRIGHT MLS #VAFV2042768

Oct 30, 2026

Sold

$415,000

$242/sq ft

Sep 21, 2026

Contingent

—

Aug 24, 2026

Price Changed

$415,000

$242/sq ft

Jul 18, 2026

Price Changed

$420,000

$245/sq ft

Jul 8, 2026

Price Changed

$425,000

$248/sq ft

Jun 22, 2026

Listed

$429,900

$251/sq ft

Jun 18, 2026

Coming Soon

$429,900

$251/sq ft

BRIGHT MLS #VAFV152044

Sep 13, 2019

Sold

$242,500

$141/sq ft

Aug 16, 2019

Pending

—

Aug 5, 2019

Contingent

—

Jul 31, 2019

Listed

$247,000

$144/sq ft

+20

Public Records

Sep 23, 2013

Sold

$225,000

$131/sq ft

MRIS #FV8120635

Sep 23, 2013

Sold

$215,000

$125/sq ft

Aug 12, 2013

Pending

—

Jul 31, 2013

Price Changed

$125/sq ft

Jun 28, 2013

Listed

$128/sq ft

+25

BRIGHT MLS #1003595934

Sep 23, 2013

Sold

$215,000

$125/sq ft

Aug 10, 2013

Listing Removed

—

Jun 28, 2013

Listed

$214,900

$125/sq ft

Public Records

Apr 17, 2009

Sold

$189,000

$110/sq ft

MRIS #FV6990542

Mar 16, 2009

Contingent

—

Public Records

May 1, 2003

Sold

$169,900

$99/sq ft

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2026

$1,763 (+10.4%)

$103,000 + $229,660

$332,660

2025

$1,597 (+14.1%)

$103,000 + $229,660

$332,660

2024

$1,399

$87,000 + $187,400

$274,400

2023

$1,399 (+3.0%)

$87,000 + $187,400

$274,400

2022

$1,358

$67,000 + $155,700

$222,700

2021

$1,358 (+5.8%)

$67,000 + $155,700

$222,700

2020

$1,284

$67,000 + $143,500

$210,500

2019

$1,284 (+8.0%)

$67,000 + $143,500

$210,500

2018

$1,189 (+1.7%)

$67,000 + $143,500

$210,500

2017

$1,169 (+11.6%)

$67,000 + $127,900

$194,900

2016

$1,048 (+9.7%)

$67,000 + $127,900

$194,900

2014

$955

$49,500 + $113,800

$163,300

Public record

Public record
Zoning

Beds

Baths

2.5

Stories

1.7

Lot width

—

Lot depth

—

Lot size

0.3 Acres

Year renovated

2015

Sq. Ft.

1,714

Year built

1998

Style

Single Family Residential

County

Frederick County

APN

55I 1 4 267

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 23, 2026.

Residential Performance District

Part 402 is intended to provide for a compatible mixture of quality residential housing types within the Urban Development Area, consistent with the residential land use policies of the Comprehensive Plan. The plan identifies basic land use characteristics which are to be encouraged: Efficient land use patterns that create high-quality neighborhoods that are attractive and pedestrian oriented; Densities that promote a compact and efficient use of land; Reduced housing and public facility costs; Energy efficient housing and housing patterns; Sustainable and environmentally sensitive land use.; It is the intent of this Part 402 to allow a mixture of housing types on the land within an approved master development plan. Within this Part 402, the permitted development percentages and densities for all housing types are identified. The master development plan shall specify the amount and percentages of all proposed housing types.

Permitted uses

Include but are not limited to:

Religious facility
Housing-Group
Housing-Single unit
Housing-Multiple units
Housing-Senior
Infrastructure
Public service
Educational/school
Fire house
Library

Property details

Parking

Parking Information
Driveway

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On 1st Upper Level: 3
# of Bedrooms On Main Level: 1

Bathroom Information
# of Bathrooms (Half) On 1st Upper Level: 1
# of Bathrooms (Full) On 1st Upper Level: 1
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Half) On All Upper Levels: 1
# of Bathrooms (Full) On All Upper Levels: 1
# of Bathrooms (Half): 1
# of Bathrooms (Full): 2

Interior Information
Appliances: Built-In Microwave, Dishwasher, Disposal, Dryer, Refrigerator, Stainless Steel Appliances, Stove, Washer
Flooring Type: Carpet, Hardwood, Luxury Vinyl Plank
Interior Features: Breakfast Area, Carpet, CeilngFan(s), Entry Level Bedroom, Floor Plan - Traditional, Kitchen - Eat-In, Master Bath(s), Upgraded Countertops, Wood Floors
Living Area Sq.Ft. Source: Assessor

Room Information
Laundry Type: Hookup

Basement Information
Basement: No

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $229,660
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Construction Materials: Vinyl Siding
Foundation Details: Crawl Space
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Deck(s), Porch(es)
Structure Type: Detached
Other Structures: Shed

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $103,000

Above Grade Information
Finished Sq.Ft.: 1,714
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
County Tax: $1,597
Tax Assessed Value: $332,660
Tax Year: 2025
Tax Annual Amount: $1,597

Assessments Information
Year Assessed: 2025

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
Forced Air
Heating Fuel: Natural Gas
Hot Water: Electric
Sewer Septic: Public Sewer
Water Source: Public

Location

Homeowners Association Information
HOA Fee: $190
HOA Fee Frequency: Annually

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

Location Information
Outside City Limits
Directions: Senseny Road to left on Greenwood Rd. - Right on Woodrow Rd. - Left on Charlton Rd.

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 1,714
Stories: 1.7
Lot Size: 0.3 acres
Style: Single Family Residential
Year Built: 1998
Year Renovated: 2015
County: Frederick County
APN: 55I 1 4 267

Home facts updated by county records on Oct 23, 2026

Around this home

Schools

Greenwood Mill Elementary School

Public PreK-5 • Assigned • 0.2mi

4/10

Admiral Richard E. Byrd Middle School

Public 6-8 • Assigned • 4.0mi

5/10

Millbrook High School

Public 9-12 • Assigned • 1.5mi

4/10

Provided by GreatSchools

Climate risks

1/10 Flood Factor

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

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 101° expected this year, 17 days in 30 years

2/10 Wind Factor

2% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Winchester, VA • 22602

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

80/ 100

Very good sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.2 hrs

5.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$396,000 – $479,000

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Home values near 101 Charlton Rd

Data from public records.

Address	Redfin Estimate
107 Charlton Rd, Winchester, VA 4 Beds \| 3 Baths \| 2222 Sq. Ft.	$444,292
109 Charlton Rd, Winchester, VA 4 Beds \| 2.5 Baths \| 1714 Sq. Ft.	$371,231
104 Charlton Rd, Winchester, VA 3 Beds \| 2 Baths \| 1400 Sq. Ft.	$383,066
216 Woodrow Rd, Winchester, VA 3 Beds \| 2 Baths \| 1400 Sq. Ft.	$378,721
300 Woodrow Rd, Winchester, VA 4 Beds \| 3 Baths \| 2234 Sq. Ft.	$453,539
218 Woodrow Rd, Winchester, VA 3 Beds \| 2 Baths \| 1298 Sq. Ft.	$390,934
103 Rebecca Dr, Winchester, VA 3 Beds \| 2 Baths \| 1923 Sq. Ft.	$386,225

Address	Redfin Estimate
105 Charlton Rd, Winchester, VA 3 Beds \| 2 Baths \| 1354 Sq. Ft.	$385,365
103 Charlton Rd, Winchester, VA 4 Beds \| 2.5 Baths \| 2125 Sq. Ft.	$458,336
106 Charlton Rd, Winchester, VA 3 Beds \| 2 Baths \| 2158 Sq. Ft.	$368,521
212 Woodrow Rd, Winchester, VA 3 Beds \| 2 Baths \| 1400 Sq. Ft.	$380,491
105 Rebecca Dr, Winchester, VA 3 Beds \| 2.5 Baths \| 1910 Sq. Ft.	$410,403
102 Ladyslipper Dr, Winchester, VA 4 Beds \| 2.5 Baths \| 2149 Sq. Ft.	$492,147
304 Woodrow Rd, Winchester, VA 4 Beds \| 3 Baths \| 1657 Sq. Ft.	$420,565

Address	Redfin Estimate
108 Charlton Rd, Winchester, VA 3 Beds \| 2 Baths \| 1895 Sq. Ft.	$422,113
102 Charlton Rd, Winchester, VA 3 Beds \| 2 Baths \| 1876 Sq. Ft.	$420,780
103 Ladyslipper Dr, Winchester, VA 3 Beds \| 2.5 Baths \| 1760 Sq. Ft.	$432,929
435 Lilys Way, Winchester, VA 4 Beds \| 2.5 Baths \| 2629 Sq. Ft.	$472,968
301 Woodrow Rd, Winchester, VA 4 Beds \| 2.5 Baths \| 1714 Sq. Ft.	$402,600
103 May Cir, Winchester, VA 3 Beds \| 2 Baths \| 1298 Sq. Ft.	$396,883
302 Woodrow Rd, Winchester, VA 3 Beds \| 2 Baths \| 1992 Sq. Ft.	$400,874

Property information provided by BRIGHT MLS when last listed in 2026. This data may not match . Learn more.

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101 Charlton Rd, Winchester, VA 22602

Is this your home?

About this home

Redfin Estimate

Market trends in 22602, VA

Homeowner tools

Redfin agents who toured

Sale and tax history for 101 Charlton Rd

Public record

Property details

Parking

Interior

Exterior

Financial

Utilities

Location

Public facts

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 22602

Home values near 101 Charlton Rd

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