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$449,000 Just Listed

  • For Sale
  • Active
  • Townhouse
  • 3 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,005 Sq. Ft.
  • Updated 4 days ago
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This beautifully appointed end-unit townhome is an opportunity not to be missed! The premium lot backing to dense trees is a rare find in this prime location. The main level is perfect for entertaining with tastefully upgraded lighting, large dining and living spaces that lead to the maintenance-free deck with a bonus stone patio and fully fenced back yard. The indoor and outdoor living spaces have been perfectly maximized. Upstairs, the spacious primary suite with walk in closet serves as a private retreat, featuring a large soaking tub, separate walk-in shower, and ample space to unwind. Two additional bedrooms and a full hall bath provide plenty of room for family, guests, or a home office. The fully finished walkout lower level offers exceptional versatility with a flexible recreation area, a family room with an exercise bump out, and a full bathroom. Step out to the patio, where you'll find plenty of space for outdoor entertaining and relaxing in the private backyard setting. The owner has thoughtfully cared for the home and it features a new zone controlled HVAC system, water softener, and hot water heater booster for hot baths and showers all the way to the third floor! As an end-unit home, you'll appreciate the added privacy, natural light, and outdoor space. Residents enjoy neighborhood amenities including pickleball courts, basketball courts, playgrounds, and inviting green spaces that encourage an active and connected lifestyle! Conveniently located near shopping, dining, schools, medical facilities, and major commuter routes, this home offers easy access to all that Winchester has to offer. Enjoy nearby parks, walking trails, historic Old Town Winchester, local wineries, seasonal events, and the charm of the Shenandoah Valley, all just minutes from your doorstep. This home combines comfort, convenience, and lifestyle in one exceptional package.

Full Property Details for 109 Cheshire Ct

General

  • Price: $449,000
  • HOA FEE: $110/month
  • Taxes: $2,120 (2025)
  • Status: Active
  • Type: Townhouse
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAFV2042366
  • Updated: 6/12/2026
  • Added to Site: 6 day(s) ago

Interior

  • Interior Features: Bathroom - Soaking Tub, Breakfast Area, Bathroom - Walk-In Shower, Carpet, Ceiling Fan(s), Combination Dining/Living, Crown Moldings, Dining Area, Family Room Off Kitchen, Floor Plan - Open, Kitchen - Island, Kitchen - Table Space, Recessed Lighting, Walk-in Closet(s), Water Treat System, Window Treatments
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Cooktop, Dishwasher, Disposal, Humidifier, Refrigerator, Stove, Oven - Wall, Microwave, Dryer - Front Loading, Washer - Front Loading, Oven - Double, Water Heater
  • Flooring: Carpet, Hardwood, Tile/Brick

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 1
  • Main - 1/2 Baths: 1
  • Lower Floor Baths: 1
  • Lower - Full Baths: 1

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 3

Additional Information

  • Shared Amenities: Basketball Courts, Pickleball Courts, Tot Lots/Playground, Picnic Area

Exterior

  • Porch/Patio/Deck: Deck(s), Patio(s)

Parking

  • Total Spaces: 2
  • Parking Type: Driveway

Location

  • County: FREDERICK
  • Subdivision: FIELDSTONE
  • Driving Directions: From 81 N Take exit 315. Continue Straight onto State Route 659/Valley Mill Road. Continue Straight onto Channing Drive. Turn left onto Highcliffe Drive. Turn Right onto Cheshire Court. Home is on the left.
  • Location Details: Corner Lot/Unit

School Information

  • School District: Frederick County Public Schools
  • Elementary School: Redbud Run
  • High School: Millbrook

Community

  • Association: Yes
  • Assoc. Name: FIELDSTONE COMMUNITY ASSSOCIATION

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Traditional
  • Structure Type: End of Row/Townhouse
  • Construction: Stone
  • Basement: Yes
  • Basement Desc.: Walkout Level
  • Foundation: Slab
  • Walls/Ceilings: 9'+ Ceilings
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 3,005
  • Sq. Ft. Source: Assessor
  • Living Area: 2,615 Sq. Ft.
  • Finished Above Grnd: 2,009 Sq. Ft.
  • Finished Below Grnd: 606 Sq. Ft.
  • Year Built: 2007
  • Year Built Source: Assessor
  • Property Condition: Excellent

Unit Information

Unit 1

  • Bathrooms-Lower: 1

Lot Features

  • Lot Size (Acres): 0.1
  • Lot Size (Sq. Ft.): 4,356
  • Lot Size Source: Assessor
  • Zoning: RP
  • Lot Description: Premium, Backs to Trees
  • Fencing (Description): Fully

Financial Considerations

  • Price Per Sq. Ft.: $223.49
  • Association Fee: $110
  • Assoc Fee Freq.: Monthly
  • Assessment Year: 2025
  • City/TownTax Freq: Annually
  • County Tax: $2,120
  • County Tax Freq: Annually
  • Tax w/Assessment: $441,600
  • Tax Amount: $2,120
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 2615

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 26

Listed by Keller Williams Realty, Cynthia K. Greenya

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Listing agent

— 109 Cheshire Ct —

  • Cynthia K. Greenya

    Keller Williams Realty

Listing Office Email: kwrickc@gmail.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 109 Cheshire Ct

School District:Frederick County Public Schools, Winchester, VA
NameGradesDistance
Greenwood Mill Elementary School
281 Channing Drive, Winchester, VA 22602
K-50.5 mi
Admiral Richard E. Byrd Middle School
134 Rosa Lane, Winchester, VA 22602
6-84.3 mi
Millbrook High School
251 First Woods Drive, Winchester, VA 22603
9-121.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 109 Cheshire Ct Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/12/2026
Listed
$449,000
40.32%
MLS
11/21/2019
Sold
$319,990
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 109 Cheshire Ct

Year
Property Taxes
Change
Tax Assessment
Change
2024
$992
—
$441,600
14%
2024
$992
-50%
$389,000
—
2023
$1,984
2%
$389,000
22%
2022
$1,943
—
$318,600
—
2021
$1,943
13%
$318,600
13%
2020
$1,724
—
$282,700
—
2019
$1,724
4%
$282,700
4%
2018
$1,662
2%
$272,500
—
2017
$1,635
7%
$272,500
7%
2016
$1,521
7%
$253,500
—
2015
$1,420
17%
$253,500
22%
2014
$1,217
—
$208,000
—
2013
$1,217
—
$208,000
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Keller Williams Realty, Cynthia K. Greenya

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109 Cheshire Court, Winchester, VA 22602 (MLS# VAFV2042366) is a Townhouse property with 3 bedrooms, 3 full bathrooms and 1 partial bathroom. 109 Cheshire Court is currently listed for $449,000 and was received on June 12, 2026. Want to learn more about 109 Cheshire Court? Do you have questions about finding other Townhouse real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

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