Prominently positioned on Pleasant Street, this custom 1927 home is rich in character and timeless architectural detail while offering wonderful opportunities for personalization. The home blends the charm of yesterday with a thoughtful addition featuring a spacious dining area and family room with a dramatic floor-to-ceiling fieldstone fireplace and striking beamed ceiling—creating a warm and inviting gathering space. Hardwood floors run throughout the home, complemented by classic yesteryear detailing that reflects the craftsmanship of the era. An expansive deck overlooks the beautiful 1.80-acre property, complete with walking trails and natural surroundings ideal for outdoor enjoyment. A barn offers space for one-car parking, storage, or workshop potential. Perfectly located for commuters and convenient to area amenities, this distinctive Milton property presents a rare opportunity to restore, customize, and create your dream home in a sought-after setting.
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| Year | Land | Building | Total | Change |
|---|---|---|---|---|
| FY2025 | $514,100 | $542,500 | $1,069,000 | — |
| Date | Price | Book/Page |
|---|---|---|
| Aug 22, 2016 | $1 | 34383/472 |
Permit history not yet available for this municipality.
Discrepancies found between MLS and assessor records.
| Field | Assessor | MLS | Match |
|---|---|---|---|
| Sqft | 5,965 | 2,930 | ✗ |
| Year built | 1,987 | 1,927 | ✗ |
207 Pleasant Street, Milton MA 02186
Milton, MA 02186
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 05/06/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 05/05/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 03/09/2026 | 🏠 Listed for Sale | $1,725,000 | - | - | Original listing |
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