For sale

$415,000

Est. $2,490/mo —

•

1,714

sq ft

101 Charlton Rd, Winchester, VA 22602

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)

Listing updated: Sep 10, 2026 at 12:47pm

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #VAFV2042768

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.
3 months ago
Rachel Miller
Redfin Premier agent
230 deals

Payment calculator

$2,490 per month

Principal and interest$2,265

Property taxes

HOA dues

Home insurance

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN TODAY, 10AM TO 1PM
$635,000
4 beds2.5 baths3,437 sq ft
104 Yarrow Ct, Winchester, VA 22602
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OPEN TODAY, 11AM TO 2PM
$735,000
3 beds2.5 baths2,572 sq ft
1748 Handley Ave, Winchester, VA 22601
(703) 754-4341
OPEN TODAY, 11AM TO 2PM
$710,000
5 beds3.5 baths3,946 sq ft
110 Bentpath Ct, Winchester, VA 22602
(703) 429-0188
OPEN TODAY, 12PM TO 2PM
$629,900
3 beds2 baths2,077 sq ft
222 Summerfield, Winchester, VA 22602
(540) 773-8475
OPEN TODAY, 12PM TO 2PM
$359,000
3 beds1.5 baths1,710 sq ft
812 Appleseed Ct, Winchester, VA 22601
(540) 931-0144
OPEN TODAY, 1PM TO 3PM
$640,000
3 beds3.5 baths3,889 sq ft
118 Harvester Dr, Lake Frederick, VA 22630
(703) 430-9008
OPEN TODAY, 1:30PM TO 3:30PM
$355,000
2 beds2 baths1,234 sq ft
1847 Melvor Ln, Winchester, VA 22601
(540) 259-4090
OPEN TODAY, 2PM TO 4PM
$400,000
3 beds3 baths1,862 sq ft
123 Nightingale Ave, Stephens City, VA 22655
(703) 754-1770
OPEN TODAY, 2PM TO 4PM
$599,999
4 beds4 baths3,411 sq ft
120 April Ave, Stephens City, VA 22655
(804) 476-9870
OPEN TODAY, 2PM TO 4PM
$550,000
4 beds2.5 baths2,904 sq ft
111 Alliance Ct, Winchester, VA 22602
(571) 386-1075

Around this home

Schools

K - 12
Preschool & daycare

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

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

101 Charlton Rd · $415,000

Strong offer

$415K and above

75% chance or better to win

Why $415K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 58 days.

SALE-TO-LIST

Most homes are selling 1% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Breakfast area
Ceiling fan(s)
Floor plan - traditional
Kitchen with eat-in area
Master bath(s)
Upgraded countertops
Wood floors

Bedrooms
Three bedrooms on upper level
One bedroom on main level
At least one entry-level bedroom

Bathrooms
Two full bathrooms
One half bathroom

Kitchen
Built-in microwave
Dishwasher
Disposal
Stove
Stainless steel appliances
Refrigerator
Upgraded countertops
Eat-in kitchen

Laundry & utility
Washer and dryer included
Laundry hookup

Flooring
Hardwood
Carpet
Luxury vinyl plank

Heating & cooling
Forced air heating
Natural gas heating
Central air conditioning
Electric hot water

Sale and tax history for 101 Charlton Rd

Sale History
Tax History

Date

Event

Price

BRIGHT MLS #VAFV2042768

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

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

+25

Well loved home, over 1700 sq. ft. of very nice living space in Winchester, Frederick County. HW floors main level, large rooms & a main level bedroom with bath access. Upper level master bedroom with half bath, 2 more bedrooms and brand new washer & dryer. Huge eat-in kitchen, hardwood floor & new double oven range. Raised deck overlooks shady yard, a great place to relax & enjoy the setting.

Public Records

Apr 17, 2009

Sold

$189,000

$110/sq ft

MRIS #FV6990542

Apr 21, 2009

Delisted

—

Mar 16, 2009

Contingent

—

Feb 24, 2009

Listed

$110/sq ft

Public Records

May 1, 2003

Sold

$169,900

$99/sq ft

MRIS #FV4460644

Mar 24, 2003

Delisted

—

Mar 21, 2003

Listed

$99/sq ft

MRIS #FV60212C

Feb 10, 1997

Listed

$69/sq ft

Feb 9, 1997

Delisted

—

** 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

Finished Sq. Ft.

1,714

Unfinished Sq. Ft.

—

Total 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 Jul 13, 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

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

Redfin Estimate for 101 Charlton Rd

$412,401

$2,599 under list price of $415K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $358K to $480K.

SOLD SEP 2, 2026
$415,000 Last sold price
3 beds2 baths1,425 sq ft
104 Lloyds Rd, Winchester, VA 22602
$49/sq ft
3 years older
basement
SOLD JUL 14, 2026
$400,000 Last sold price
3 beds2 baths1,390 sq ft
117 Ware Pl, Winchester, VA 22602
$46/sq ft
5 years older
SOLD AUG 7, 2026
$465,000 Last sold price
2 beds2 baths1,800 sq ft
105 Amberfield Ct, Winchester, VA 22602
$16/sq ft
26 years newer
SOLD JUN 22, 2026
$400,000 Last sold price
3 beds2 baths2,148 sq ft
305 Woodrow Rd, Winchester, VA 22602
$56/sq ft
1 year older
SOLD AUG 3, 2026
$358,000 Last sold price
3 beds2 baths1,615 sq ft
114 Woodys Pl, Winchester, VA 22602
$20/sq ft
10 years older
SOLD JUL 24, 2026
$480,000 Last sold price
4 beds2.5 baths2,023 sq ft
102 Brockham Ct, Winchester, VA 22602
$5/sq ft
28 years newer

Rental earnings

Est. $2,024 per month, based on comparable rentals

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