Property

Winchester, VA 22602 109 Cheshire Court

109 Cheshire Court Winchester, VA - Image 1109 Cheshire Court Winchester, VA - Image 2109 Cheshire Court Winchester, VA - Image 3
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Presented By: Keller Williams Realty
  • MLS# VAFV2042366
  • 06/11/2026
  • Request Tour
  • Request Info
  • Beds • 3
  • Full/Half Baths • 3 / 1
  • SQFT • 2,615

Home Details

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.
Presented By: Keller Williams Realty

Interior Features for 109 Cheshire Court

Bedrooms

Bedrooms Count All Upper Levels3
Bedrooms Count Upper Level 13
Total Bedrooms3

Bathrooms

Bathrooms Half Main Level1
Bathrooms Full Upper Level 12
Bathrooms Full Lower Level 11
Bathrooms Full All Upper Levels2
Bathrooms Full All Lower Levels1
Bathrooms Count Upper Level 12.00
Bathrooms Count Lower Level 11.00
Bathrooms Count All Upper Levels2
Bathrooms Count All Lower Levels1
Half Baths1
Total Baths4

Other Interior Features

LivingAreaSourceAssessor
Below Grade Unfin Area UnitsSquare Feet
Below Grade Unfin SQFT390
Below Grade Unfin SQFT SourceAssessor
Above Grade Finished Area2009
Above Grade Finished Area SourceAssessor
Above Grade Finished Area Unit TypeSquare Feet
BasementWalkout Level
Basement (Y/N)Yes
Below Grade Finished Area606
Below Grade Finished Area SourceAssessor
Below Grade Finished Area Unit TypeSquare Feet
Central Air Y/NYes
Fireplace Y/NYes
FlooringCarpet, Hardwood, Tile/Brick
Heating FuelElectric
Heating Y/NYes
Hot WaterElectric
Interior AmenitiesBathroom - 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, K
Total Fireplaces1

General for 109 Cheshire Court

AccessibilityNone
AppliancesCooktop, Dishwasher, Disposal, Humidifier, Refrigerator, Stove, Oven - Wall, Microwave, Dryer - Front Loading, Washer - Front Loading, Oven - Double, Water Heater
Architectural StyleTraditional
Assoc Fee Paid PerMonthly
Association AmenitiesBasketball Courts, Pickleball Courts, Tot Lots/Playground, Picnic Area
Association NameFIELDSTONE COMMUNITY ASSSOCIATION
Bathrooms Count Main Level1.00
CityWINCHESTER
Condo/Coop Association fee Y/NNo
Construction MaterialsStone
Contingency TypeHome Inspection
Cool FuelElectric
CoolingCentral A/C
CountyFREDERICK
DirectionsFrom 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 th
Full Baths3
Garage Y/NNo
HOAYes
HOA Fee$110.00
HeatingHeat Pump(s)
Home Warranty Y/NYes
Legal SubdivisionFIELDSTONE
Levels3
Living Area2615
Location TypeCorner Lot/Unit
Lot Size Square Feet4356.00
Lot Size UnitsSquare Feet
New ConstructionNo
Other StructuresAbove Grade, Below Grade
OwnershipFee Simple
Patio/Porch FeaturesDeck(s), Patio(s)
Possession0-30 Days CD
Price Per Sq Ft Total AG216.53
Property ConditionExcellent
Property TypeResidential
School DistrictFREDERICK COUNTY PUBLIC SCHOOLS
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive Under Contract
StatusACTIVE UNDER CONTRACT
Structure TypeEnd of Row/Townhouse
Subdivision NameFIELDSTONE
Tax Annual Amount2120.0
Tax Assessed Value441600.0
Tax Lot26
Tax Year2025
Total SQFT3005
Vacation Rental Y/NNo
Virtual TourClick here
Water Access Y/NNo
Year Built2007
Year Built SourceAssessor
ZoningRP

Exterior for 109 Cheshire Court

FencingFully
Foundation DetailsSlab
Land Assessed Value68000.00
Land Use Code100R
Lot FeaturesPremium, Backs to Trees
Lot Size Acres0.10
Lot Size SourceAssessor
Navigable Water Y/NNo
PoolNo Pool
Total Parking Spaces2
Type of ParkingDriveway
Water Oriented Y/NNo
Water SourcePublic
Water View Y/NNo
Waterfront Y/NNo

Additional Details

Price History

Schools

Middle School N/A
High School Millbrook High School
Elementary School Redbud Run Elementary School

Tina Torres

Broker/Owner
Price $435,000
MLS#VAFV2042366
List Date 06/11/2026
Property Type Contingent
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