No photos available for this listing

$5,995,000

55 Parkwood Drive, Milton MA 02186
Milton, MA 02186
Listed by Kevin G. Keating
Bedrooms
7
Bathrooms
7.3
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 #
73519804
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
N/A
On market date
N/A
Stories
N/A
Garage spaces
6
Lot size
2.77 acres
Loading map…

Nearby schools

Within 10 miles · public school directory data (NCES)

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

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
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

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated May 19, 2026.

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.