For sale

Price cut: $900 (6/15)

$699,900

23 Shepard Ct #U23, Winchester, MA 01890

3beds

1,380sqft

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Condex

Built in 1890

-- sqft lot

$-- Zestimate^®

$507/sqft

$100/mo HOA

What's special

Storage shedMature landscapingSun-filled homeHardwood floors throughoutUpdated kitchen and baths

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.

35 days

2,719

130

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Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 4
Full bathrooms: 2
1/2 bathrooms: 2

Primary bedroom

Level: Second
Area: 181.25
Dimensions: 15 x 12.08

Bedroom 2

Level: Second
Area: 107.14
Dimensions: 11.08 x 9.67

Bedroom 3

Level: Third
Area: 216.19
Dimensions: 15.08 x 14.33

Bathroom 1

Features: Bathroom - Half
Level: Second
Area: 18.67
Dimensions: 4.67 x 4

Bathroom 2

Features: Bathroom - Full
Level: Third
Area: 32.5
Dimensions: 7.5 x 4.33

Bathroom 3

Features: Bathroom - Full
Level: Basement

Dining room

Level: First

Kitchen

Level: First
Area: 168.75
Dimensions: 15 x 11.25

Living room

Level: First
Width: 11.25

Heating

Central

Cooling

Ductless

Appliances

Included: Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer
Laundry: In Basement

Features

Entrance Foyer
Flooring: Wood, Tile
Windows: Insulated Windows
Has basement: Yes
Has fireplace: No

Interior area

Total structure area: 1,380
Total interior livable area: 1,380 sqft
Finished area above ground: 990
Finished area below ground: 390

Property

Parking

Total spaces: 2
Parking features: Off Street
Uncovered spaces: 2

Features

Patio & porch: Porch, Deck, Patio
Exterior features: Porch, Deck, Patio, Storage, Garden

Details

Parcel number: M:013 B:0662 L:0,4634455
Zoning: RG

Construction

Type & style

Home type: MultiFamily
Property subtype: Condex
Attached to another structure: Yes

Condition

Year built: 1890
Major remodel year: 2018

Utilities & green energy

Electric: 220 Volts, Circuit Breakers, 100 Amp Service
Sewer: Public Sewer
Water: Public

Community & HOA

Community

Features: Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Bike Path, Public School

HOA

Services included: Insurance
HOA fee: $100 monthly

Location

Region: Winchester

Financial & listing details

Price per square foot: $507/sqft
Tax assessed value: $518,300
Annual tax amount: $5,748
Date on market: 6/5/2026

Estimated market value

Not available

Estimated sales range

Not available

Price history

Date	Event	Price
6/15/2026	Price change	$699,000-0.1%$507/sqft
Source: MLS PIN #73530954 Report a problem
6/15/2026	Price change	$699,900-6.6%$507/sqft
Source: MLS PIN #73530920 Report a problem
6/5/2026	Listed for sale	$749,000$543/sqft
Source: MLS PIN #73530920 Report a problem

Public tax history

Tax history is unavailable.

Monthly payment

Est. payment

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All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.

HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.

Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.

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