Beautifully updated home offers generous living spaces & a seamless, open flow. Sun-filled living &dining areas feature hardwood floors, elegant detailing, & a fireplace that creates an inviting atmosphere. The kitchen is thoughtfully designed with quartz countertops, custom cabinetry, stainless appliances, wine chiller, & large island that opens to the dining area, which flows into the family room with direct access outdoors - ideal for yard access & entertaining. French doors between the kitchen, dining, & family room help to create a quieter, more private setting for the bedroom & formal living areas. The primary suite provides a private retreat with a full bath, while three additional bedrooms & full bath complete this level. A finished walk-out lower level adds versatility with a fireplace playroom, 5th bedroom, full bath, & laundry - great for guests or multi-generational living. Landscaped grounds & inviting outdoor areas, complemented by an attached garage & ample parking
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| Year | Land | Building | Total | Change |
|---|---|---|---|---|
| FY2026 | $1,040,300 | $544,900 | $1,585,200 | — |
| Date | Price | Book/Page |
|---|---|---|
| Jul 20, 1994 | $395,000 | 24714/85 |
Permit history not yet available for this municipality.
Discrepancies found between MLS and assessor records.
| Field | Assessor | MLS | Match |
|---|---|---|---|
| Sqft | 4,040 | 3,271 | ✗ |
| Year built | 1,963 | 1,963 | ✓ |
29 Pilgrim Dr, Winchester MA 01890
Winchester, MA 01890
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 04/15/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 04/14/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 03/25/2026 | 🏠 Listed for Sale | $1,749,000 | - | - | Original listing |
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