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. Priced to sell, open to seasonable offers.
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| Year | Land | Building | Total | Change |
|---|---|---|---|---|
| FY2026 | $0 | $675,600 | $675,600 | — |
| Date | Price | Book/Page |
|---|---|---|
| May 1, 2025 | $730,000 | 174/166 |
| Jun 28, 2022 | $502,000 | 166/6 |
Permit history not yet available for this municipality.
Discrepancies found between MLS and assessor records.
| Field | Assessor | MLS | Match |
|---|---|---|---|
| Sqft | 1,512 | 1,380 | ✗ |
| Year built | 1,890 | 1,890 | ✓ |
23 Shepard Ct # U23, Winchester MA 01890
Winchester, MA 01890
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 06/15/2026 | ↓ Price Reduced | $699,000 | $50,000 | - | From $749,000 to $699,000 (-6.7%) |
| 06/05/2026 | 🏠 Listed for Sale | $749,000 | - | - | Original listing |
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