Huge Price Drop – Best Value in the Winchester School District! Beautifully maintained townhouse-style condex offering 3 levels of living in a prime Winchester location. This sun-filled home features 3 bedrooms, 2 full baths, 2 half baths, and a flexible third-floor suite perfect as a primary bedroom, guest space, or home office. Recent updates include a 2019 high-efficiency gas boiler, 2019 tankless hot water system, 2023 mini-split cooling system, 2025 new roof, insulated windows, updated kitchen and baths, and hardwood floors throughout. Enjoy a private exclusive-use yard with deck, patio, mature landscaping, storage shed, and 2 off-street parking spaces. Low $100/month condo fee. Ideally located next to Elizabeth C. McDonald Field with tennis courts, sports fields, walking paths, and a new playground, and just minutes to Winchester Center. A rare opportunity and one of the most affordable ways to enjoy top-rated Winchester schools.
This home has been viewed 16 times
Last Checked: June 20th, 2026 at 6:13am (Source: MLS PIN #73530920)
Air Conditioning
Waterview
Lead Paint Free
General Information for 23 Shepard Ct # U23, Winchester MA 01890
Listing ID73530920
Property TypeCondominium
Price699900 ($507.17/SqFt)
Building Style2/3 Family
CityWinchester
CountyMiddlesex
Neighborhood(s)
Total Parking2
Unit Level1
Levels in Unit4
Year Built1890
Year Built SourcePublic Records
Year Renovated2018
Year Built DetailsRenovated Since
Building Construction Status
ZoningRG
Unit Features for 23 Shepard Ct # U23, Winchester MA 01890
Approximate Living Area Total1380
Living Area Includes BasementYes
Rooms9
Bedrooms3
Primary En Suite BathroomYes
BasementFull
Cooling1, Split
LaundryArchway
Fireplaces
Outdoor SpaceNo
FlooringTile
Electric220 Volts
AppliancesRange
Condo Association Features for 23 Shepard Ct # U23, Winchester MA 01890
Pet PolicyAllowed
Building ManagementDeveloper Advisory Board
Building Construction Status
Number of Units2
Units Owner Occupied2
Year Built1890
Year Built DetailsRenovated Since
Year Built SourcePublic Records
Unit Last Renovated2018
WaterPublic
SewerPublic Sewer
Parking Features1
Building Amenities
Disclosures for 23 Shepard Ct # U23, Winchester MA 01890
Lead PaintNone
UFFI
Living Area Includes BasementYes
Living Area Disclosure
Building Area SourceOwner
Special Listing Conditions
ExclusionsSee Disclosures
Compensation Based On
Documents Available
Financial Information for 23 Shepard Ct # U23, Winchester MA 01890
Association Fee
Optional Fee0
Association Fee IncludesLandscaping
Optional Fee Includes
Association Fee FrequencyMonthly
Assessed Value$518,300
Real Estate Tax5748
Tax Year2025
Location Information for 23 Shepard Ct # U23, Winchester MA 01890
Elementary SchoolLynch
Middle SchoolMccall
High SchoolWinchester High
Neighborhood(s)
Area AmenitiesWalk/jog Trails
Contact Information for 23 Shepard Ct # U23, Winchester MA 01890