For Sale83d on market
157 Oak Dr
Winchester, VA, 22603 • 22603 • Frederick County
$525,000
$230/sqft
-$25,000 since Mar 30, 2026
Down payment assistance available
4Beds
3Baths
2,280Sqft
5 acLot
1989Built
Property DNA
Trees/Woods Views
Trees/Woods
Colonial Style
Built 1989 · 37 years of history
Westwood Terrace
22603
1 Fireplace
Wood Burning
Above Grade
Above Grade
2-Car Garage
Storage · Garage Faces Front · Inside Entrance · Garage Door Opener · Driveway · Attached
Premium Finishes
Bathroom - Walk-In Shower · Walk-In Closet(s)
Hardwood & Wood Floors
Quality flooring throughout
This home is getting attention
Listed 83 days ago · 4,515 views · 209 saves
Market activity
Demand and pricing signals for this listing
4,515 views
People checking out this listing
209 saves
Buyers have saved this home
83 days on market
Established listing
$230/sqft
Price per square foot
Selling Soon Prediction
ModerateThis home ranks in the top 36% of listings most likely to go under contract soon, based on market activity and demand signals.
Likelihood score
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About this home
Single Family · Built 1989
STOP THE PRESSES!! This PRICE ADJUSTMENT is not a typo! The weather is warmer and Spring is in the air.... This home is ready for YOU! Welcome home to 157 Oak Dr. in Winchester, VA—an inviting property offering comfort, thoughtful updates, and a peaceful setting. This home has been refreshed with luxury vinyl plank flooring throughout most of the home and fresh paint, creating a clean, move-in-ready feel. Be Sure to Watch The Video to Experience Even More of This Home! The primary suite has been remodeled, including an updated bathroom and walk-in closet, creating a comfortable retreat. A large bonus room over the 2-car garage offers endless possibilities—home office, playroom, gym, or guest space. But wait, there is more! The garage has built in work benches and tool storage. The home features dual-zoned heating and cooling for added comfort, with the upper-level heat pump replaced in 2021, as well as a new water filtration system installed in 2022. Surrounded by trees for privacy, this property offers a serene setting while remaining just minutes from Winchester’s medical facilities, restaurants, and shopping. Convenient access to I-81 makes commuting easy. Do Not Miss Your Opportunity to Tour This Home! Call Your Agent or The Listing Agent Today
Standout features identified
Our analysis highlights updated bathroom, fresh paint, and walk-in closet as key attractions of this home.
Estimated monthly payment
Based on current rates
$3,286/month
Principal & Interest$2,561
Property Tax$525
Insurance$175
HOA$25
Down payment20% ($105,000)
3%50%
Est. 6.16% rate · 30yr fixed · $420,000 loan
Full calculator →Virtual Tour
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At a glance
Key facts and listing details
TypeSingle Family Residence
Year Built1989
HeatingHeat Pump, Zoned, Electric
CoolingCentral Air, Electric
Parking2 Attached Garage spaces
HOA$300 annually
Lot5 Acres
Days on Zillow83 Days
Price/sqft$230
Property
Home typeSingle Family
Sub-typeSingle Family Residence
StyleColonial
ConditionExcellent
Year built1989
Stories2
Systems
HeatingHeat Pump, Zoned, Electric
CoolingCentral Air, Electric
ConstructionVinyl Siding
Water / SewerWell / On Site Septic, Septic < # of BR
Parking & Outdoor
ParkingStorage, Garage Faces Front, Inside Entrance, Garage Door Opener, Driveway, Attached
Garage2 spaces
Fireplaces1
FencingInvisible
Lot5 Acres
Location & Tax
Neighborhood22603
ZoningRA
Annual tax$1,848
Parcel4074
Bathrooms & Fees
Full baths2
HOA$25/mo
Features & details
16 categories of property features
Interior Features
Interior
Additional Stairway
Bathroom - Walk-In Shower
Bathroom - Tub Shower
Ceiling Fan(s)
Central Vacuum
Breakfast Area
Dining Area
Family Room Off Kitchen
Pantry
Primary Bath(s)
Walk-In Closet(s)
Appliances
Microwave
Dishwasher
Disposal
Dryer
Oven/Range - Electric
Refrigerator
Washer
Extra Refrigerator/Freezer
Water Treat System
Electric Water Heater
Flooring
Hardwood
Luxury Vinyl
Wood
Heating
Heat Pump
Zoned
Electric
Cooling
Central Air
Electric
Laundry
Main Level
Fireplace
Wood Burning
Windows
Bay/Bow
Vinyl Clad
Accessibility
None
Exterior Features
Parking
Storage
Garage Faces Front
Inside Entrance
Garage Door Opener
Driveway
Attached
Construction
Vinyl Siding
Lot Features
Backs to Trees
Landscaped
Wooded
Views
Trees/Woods
Pool Features
None
Utilities
Satellite Internet Service
Other Internet Service
Other Structures
Above Grade
Room details
13 rooms detailed
Primary Bedroom
Upper15×14 ft210 sqft
Ceiling Fan(s)Flooring - Luxury Vinyl PlankWalk-In Closet(s)
Bedroom2
Upper11×9 ft99 sqft
Ceiling Fan(s)Flooring - Luxury Vinyl Plank
Bedroom3
Upper12×12 ft144 sqft
Flooring - Luxury Vinyl PlankCeiling Fan(s)
Bedroom4
Upper12×11 ft132 sqft
Flooring - Luxury Vinyl PlankCeiling Fan(s)
Primary Bathroom
Upper9×8 ft72 sqft
Flooring - SlateBathroom - Stall Shower
Bathroom2
Upper9×8 ft72 sqft
Bathroom - Tub Shower
Listing insights
Market data and value estimates
StatusFor Sale
Days on market83
Est. value$521,400
Est. rent$2,844/mo
Tax rate0.42%
Price/sqft$230
On marketJan 15, 2026
PostedJan 15, 2026
Last sold$396,000
MLS updatedApr 2, 2026
Tour days9
Views4,515
Favorites209
How are the schools in Winchester?
3 schools rated nearby
Location
Winchester, VA, 22603
Price history
8 events
DateEventPrice$/sqftSource
Mar 30, 2026Price Change$525,000$230Bright MLS
Mar 15, 2026Price Change$550,000$241Bright MLS
Feb 22, 2026Price Change$579,900$254Bright MLS
Jan 15, 2026Listed For Sale$590,000$259Bright MLS
Aug 31, 2021Sold$396,000$174Bright MLS
Jul 20, 2021Pending Sale$384,900$169Bright MLS
Jul 15, 2021Listed For Sale$384,900$169Bright MLS
Mar 24, 2000Sold$178,000$78Public Record
Price Change$525,000
Mar 30, 2026•$230/sqft•Bright MLS
Price Change$550,000
Mar 15, 2026•$241/sqft•Bright MLS
Price Change$579,900
Feb 22, 2026•$254/sqft•Bright MLS
Listed For Sale$590,000
Jan 15, 2026•$259/sqft•Bright MLS
Sold$396,000
Aug 31, 2021•$174/sqft•Bright MLS
Pending Sale$384,900
Jul 20, 2021•$169/sqft•Bright MLS
Listed For Sale$384,900
Jul 15, 2021•$169/sqft•Bright MLS
Sold$178,000
Mar 24, 2000•$78/sqft•Public Record
Tax history
24 years of records
YearTax paidAssessed value
Apr 8, 2025$1,848$384,900
Apr 8, 2024$1,645$322,500
Apr 8, 2023$1,645$322,500
Apr 8, 2022$1,668$273,500
Apr 8, 2021$834$273,500
Apr 8, 2020$1,548$253,800
Apr 8, 2019$3,096$253,800
Apr 8, 2018$1,463$239,800
Apr 8, 2017$1,439$239,800
Apr 8, 2016$1,276$212,600
Apr 8, 2015$1,191$212,600
Apr 8, 2014$635$204,100
Apr 8, 2013—$204,100
Apr 8, 2012—$217,100
Apr 8, 2011—$217,100
Apr 8, 2010—$253,700
Apr 8, 2009—$253,700
Apr 8, 2008—$259,500
Apr 8, 2007—$259,500
Apr 8, 2006—$259,500
Apr 8, 2005—$259,500
Apr 8, 2003—$182,000
Apr 8, 2002—$182,000
Apr 8, 2001—$182,000
Nearby homes
Neighborhood details
Local context around this listing
Winchester, VA • Frederick County
Nearby cities
Clear BrookCross JunctionGoreMiddletownStar TanneryStephens CityStephensonWhite Post
Nearby zip codes
2260122602226032260422638
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