Set on over 1.4 acres in one of Milton’s most picturesque settings, 268 Highland Street is a timeless brick-front Colonial where elegance, warmth, and unforgettable gatherings have defined this home for decades. From the slate roof and copper downspouts to the sweeping green lawns and mature landscape, every detail reflects classic New England charm. Inside, beautifully updated kitchens and baths blend seamlessly with gracious living spaces designed for entertaining and everyday comfort. A stunning home office overlooks the patio and expansive backyard, creating an inspiring work-from-home retreat. Beyond the main residence sits an extraordinary three-story barn—offering endless possibilities for creative space, storage, hobby use, or potential future ADU opportunities. Rarely does a property offer this combination of character, land, flexibility, and legacy just minutes from Boston.
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| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 06/02/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 06/02/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 05/26/2026 | 🏠 Listed for Sale | $1,895,000 | - | - | Original listing |
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $15,880 | $1,431,900 |
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268 Highland St, Milton MA 02186
Milton, MA 02186
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