287 Hillside St, Milton, MA 02186 - Photo 1

1/1

$3,200,000

Sold
Closed
Single Family
5 Beds
5 Full Baths
1 Partial Bath
6,950 Sq. Ft.
2.52 Acres
3 Car Garage

1/1

Property Description

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.

Full Property Details

Full Property Details for 287 Hillside St

General

Sold For: $3,200,000
Taxes: $25,545 (2025)
Status: Closed
Type: Single Family
Source: MLSPin
MLS ID: 73357166
Added to Site: 282 day(s) ago

Interior

Number of Rooms: 12
Interior Features: Closet, Bedroom, Bonus Room, Bathroom, Home Office, Foyer, Wired for Sound, Elevator
Fireplace: Yes
Number of Fireplaces: 7
Fireplace(s): Dining Room, Family Room, Living Room, Master Bedroom, Bedroom
Appliances: Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Water Treatment, Wine Refrigerator, Range Hood
Flooring: Tile, Hardwood, Flooring - Hardwood

Rooms

Bathrooms

Total Bathrooms: 6
Full Bathrooms: 5
Half Bathrooms: 1
Main - Full Baths: 5
Main - 1/2 Baths: 1
Bathroom 1: Half Bathroom, Stone/Ceramic Tile Flooring, First
Bathroom 2: Full Bathroom, Bathroom Double Vanity/Double Sink, T, Second
Bathroom 3: Bathroom - Full, Bathroom - Tiled With Tub & Shower, Second

Bedrooms

Total Bedrooms: 5
Primary Bedroom: Second
Bedroom 2: Closet, Hardwood Flooring, Second
Bedroom 3: Fireplace, Closet, Hardwood Flooring, Second
Bedroom 4: Fireplace, Closet, Hardwood Flooring, Second

Other Rooms

Living Room: Custom-Built Closet/Cabinets, Hardwood Flooring, French Doors, Crown Molding, 16.00 x 16.00, First, 256 Sq. Ft.
Family Room: Custom-Built Closet/Cabinets, Hardwood Flooring, Recessed Lighting, Crown Molding, 26.00 x 23.00, First, 598 Sq. Ft.
Kitchen: Custom-Built Closet/Cabinets, Hardwood Flooring, Pantry, Stone/Granite/Solid Countertops, Kitchen Island, Breakfast Bar/Nook, Remodeled, 19.00 x 13.00, First, 247 Sq. Ft.
Dining Room: Custom-Built Closet/Cabinets, Hardwood Flooring, Picture Window(s), Crown Molding, Decorative Molding, 18.00 x 17.00, First, 306 Sq. Ft.
Office: Flooring - Hardwood, Second
Laundry: Flooring - Hardwood, Second Floor

Additional Information

Pool: Yes
Pool Description: Pool - Inground Heated
Year Round: Yes

Exterior

Exterior Features: Porch, Pool - Inground Heated, Hot Tub/Spa, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Garden, Horses Permitted, Stone Wall

Parking

Garage: Yes
Attached garage: Yes
Garage Spaces: 3
Total Spaces: 6
Parking Features: Attached, Off Street, Driveway

Location

County: Norfolk
Subdivision: Hillside Neighborhood
Driving Directions: Randolph Ave. to Hillside St.

Heating & Cooling

Cooling Type: Central Air
Heating Type: Forced Air, Steam, Oil
Heating Fuel: Forced Air, Steam, Oil

Utilities

Sewer: Private Sewer
Water: Public

Structural Information

Architectural Style: Colonial
Exterior Const.: Frame
Basement: Yes
Basement Desc.: Unfinished
Roof: Wood
Square Feet: 6,950
Sq. Ft. Source: Public Records
Living Area: 6,950 Sq. Ft.
Year Built: 1912

Lot Features

Lot Size (Acres): 2.52
Lot Dimensions: 2.52
Frontage: Public
Street/Road Desc.: Paved
Fence: Yes
Lot Features: Gentle Sloping
Fencing (Description): Fenced

Financial Considerations

Price Per Sq. Ft.: $460.43
Tax Amount: $25,545
Tax Year: 2025

Disclosures and Reports

Property ID: M:N B:014 L:4B, 134014

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Meet the listing agent

— 287 Hillside St —

Meredith Hall

Email Me

(617) 930-3977 mobile
(617) 696-4430 direct

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NMLS#: 1598647

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Schools

Schools serving 287 Hillside St

School District:Milton School District, Milton, MA

Name	Grades	Distance
Milton High School 25 Gile Road, Milton, MA 02186	9-12	1.8 mi

Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 287 Hillside St

Date

Details

Price

Change

Source

7/18/2025

Sold

$3,200,000

-5.88%

MLS

5/07/2025

Price Reduced

$3,400,000

-10.41%

MLS

4/09/2025

Listed

$3,795,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Condo
Active
Updated 1 day ago

2
Beds
2
Total Baths
1,166
Sq. Ft.

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Condo
Active
Updated 2 days ago

2
Beds
2
Total Baths
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Sq. Ft.

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Updated 1 day ago

2
Beds
2
Total Baths
1,452
Sq. Ft.

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Active
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2
Beds
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Total Baths
1,076
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Single Family
Active
Updated 13 hours ago

4
Beds
2
Total Baths
1,948
Sq. Ft.

Listed by Lu Ouyang (617) 763-0708

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Price Reduced

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Active
Updated 13 hours ago

2
Beds
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Total Bath
684
Sq. Ft.

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Condo
Active
Updated 13 hours ago

2
Beds
2
Total Baths
1,081
Sq. Ft.

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$2,850,000

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Closed

5
Beds
4
Total Baths
4,644
Sq. Ft.

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Single Family
Closed

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Beds
7
Total Baths
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Sq. Ft.

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Sold

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Total Baths
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7
Beds
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Total Baths
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Sq. Ft.

287 Hillside St, Milton, MA 02186 (MLS# 73357166) is a Single Family property that was sold at $3,200,000 on July 18, 2025. This property was listed by Meredith Hall from our Milton Office.Want to learn more about 287 Hillside St? Do you have questions about finding other Single Family real estate for sale in Milton? You can browse all Milton real estate or contact a Coldwell Banker agent to request more information.

287 Hillside St Milton, MA 02186