287 Hillside St, Milton MA 02186
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Sale Statistics
This property sold for 15.7% below the original asking price.
The property spent 53 days on market before selling.
About this home
Experience the grandeur of this elegant 1912 Colonial sited along a private treelined drive. Beautifully designed for the President of Baker Chocolate, this estate is the perfect blend of exquisite period detail & modern amenities. Its magnificence is apparent upon entering, with high ceilings, front to back expansive foyer, a wood paneled family room and signature staircase leading to 5 beds including a third floor walk up suite for guests/au pair/teen. The chef's kitchen with butler's pantry connects to a grand dining room, perfect for entertaining. The beauty of this home extends to the manicured grounds, a gardener's delight with specimen trees and a spectacular gunite pool and views of the Blue Hills. A charming separate building with an historic stone fireplace, lodge room and bowling alley will delight your family and guests. This one of a kind property is located minutes from Boston, Logan Airport, Blue Hills walking/biking trails Milton Center and Milton Academy.
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Property History
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Property Timeline
Sold
Jul 18, 2025Listed for Sale
Apr 9, 2025| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/18/2025 | ✓ Sold | $3,200,000 | - | - | Property sold |
| 04/09/2025 | 🏠 Listed for Sale | $3,400,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $25,545 | $2,303,400 |
Financial Details
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Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
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Nearby Schools
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10 schoolsMiddle Schools
1 schoolHigh Schools
2 schoolsLocation
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Hillside Neighborhood
287 Hillside St, Milton MA 02186
Milton, MA 02186
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