Must see! sprawling 2-3 family beautifully renovated & expanded home offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr bedrm & full bath, plus a flexible suite w/ kitchenette, sitting room & full bath. Upstairs offers 3 add' bedrooms & a full bath. The finished lower level includes a family room, office, exercise space, bonus room w/ walkout, workshop, storage & cedar closet. Additional highlights include an oversized 2-car garage with EV charger, elevator lift, solar array, & direct access to the apartment featuring vaulted ceilings, gas fireplace, full kitchen, laundry & private deck. Set on an oversized level lot with mature landscaping, deck, patio & gazebo on a quiet cul-de-sac!
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| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/06/2026 | ↓ Price Reduced | $1,999,000 | $100,000 | - | From $2,099,000 to $1,999,000 (-4.8%) |
| 06/02/2026 | ↓ Price Reduced | $2,099,000 | $101,000 | - | From $2,200,000 to $2,099,000 (-4.6%) |
| 04/24/2026 | 🏠 Listed for Sale | $2,200,000 | - | - | Original listing |
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $25,122 | $2,265,300 |
16 & 16A Glenwood Ave, Winchester MA 01890
Winchester, MA 01890
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