Single Family Residence at 55 Parkwood Drive, Milton MA 02186, Milton
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$5,995,000

55 Parkwood Drive, Milton MA 02186
Milton, MA 02186
Listed by Kevin G. Keating
Bedrooms
7
Bathrooms
8.5
Living area
9,320 sqft
Year built
1915

About this home

Experience the pinnacle of Milton living at this 1915 French Colonial masterpiece. Set on nearly three acres at the foot of the Blue Hills Reservation, this legacy estate offers a rare blend of privacy and prestige. The grounds are an entertainer’s dream, featuring an in-ground pool, pool house, and a two-story, five-bay garage with an attached vintage greenhouse. Spanning 9,000+ sq. ft., the residence boasts seven bedrooms, ten bathrooms, and nine fireplaces. The main level offers grand formal spaces, including a mahogany-paneled library and a sophisticated office. The chef’s culinary suite is a masterwork of marble and high-end gas ranges. Retreat to the palatial primary wing—a four-room haven with dual baths and expansive views. The finished lower level adds versatility with twin fitness studios and a private lounge and office. Located eight miles from Boston and Logan, enjoy a country-manor lifestyle near world-class Milton Academy. A rare architectural gem. Welcome home!

Highlights

Private poolFireplace

Property details

MLS
MLS Property Information Network
MLS #
73519804
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
151
On market date
May 15, 2026
Stories
N/A
Total bathrooms
8.5
Garage spaces
6
Parking spaces
21
Lot size
2.77 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Cunningham School
2.34 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
617
Student:teacher ratio
12.6:1
District
Milton
Middle
Charles S Pierce Middle
2.38 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
928
Student:teacher ratio
12.1:1
District
Milton
High
Milton High
2 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,106
Student:teacher ratio
13.8:1
District
Milton

Walkability

Blended score for Milton's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

52
Somewhat walkable
out of 100
EPA National Walkability Index
13.0 / 20 -- Above average walkable
Google Places amenity density
33 / 100
Restaurants & cafes1
Grocery stores1
Parks2
Schools1
Transit stops17
Pharmacies0

Mortgage calculator

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Est. monthly payment
$36,253/mo
$1,199,000 down
$4,796,000 loan
Principal & interest$31,107
Property tax (est.)$4,996
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 21 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.