Single Family Residence at 1066 Hillside St, Milton MA 02186
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 2 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 3 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 4 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 5 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 6 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 7 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 8 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 9 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 10 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 11 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 12 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 13 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 14 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 15 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 16 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 17 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 18 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 19 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 20 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 21 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 22 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 23 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 24 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 25 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 26 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 27 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 28 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 29 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 30 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 31 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 32 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 33 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 34 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 35 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 36 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 37 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 38 of 39
Single Family Residence at 1066 Hillside St, Milton MA 02186, photo 39 of 39
39 photos

$987,000

1066 Hillside St, Milton MA 02186
Milton, MA 02186
Listed by Bridget Conroy
Bedrooms
4
Bathrooms
1.5
Living area
2,232 sqft
Year built
1965

About this home

This spacious 9-room home on Hillside Street offers 4 bedrooms in one of Milton's most coveted settings, nestled at the edge of the Blue Hills Reservation. With miles of trails, open space, and stunning natural scenery right outside your door, the location is truly special. The generous layout gives buyers real flexibility to update and personalize, with good bones and a highly desirable address to build from. The property includes a pool currently in need of repair, presenting a great opportunity to create a standout outdoor space on your own terms. Milton is known for its excellent schools, beautiful neighborhoods, and easy access to Boston, and Hillside Road delivers all of it. For a buyer with vision and an eye for value, this is a rare chance to put your stamp on a property where nature and neighborhood come together beautifully.

Highlights

ViewPrivate poolFireplace

Property details

MLS
MLS Property Information Network
MLS #
73519606
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
160
On market date
May 14, 2026
Stories
N/A
Total bathrooms
1.5
Garage spaces
2
Parking spaces
7
Lot size
0.46 acres
Loading map…

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
Lt Peter M Hansen
2.04 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
534
Student:teacher ratio
15.7:1
District
Canton
Middle
Wm H Galvin Middle
2.01 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
790
Student:teacher ratio
13.0:1
District
Canton
High
Blue Hills Regional Vocational Technical
1.75 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
917
Student:teacher ratio
11.6:1
District
Blue Hills Regional Vocational Technical

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).

45
Somewhat walkable
out of 100
EPA National Walkability Index
11.8 / 20 -- Above average walkable
Google Places amenity density
23 / 100
Restaurants & cafes1
Grocery stores0
Parks1
Schools1
Transit stops6
Pharmacies0

Market position

How this listing compares to current activity in Milton, from live MLS data.

On the market 160 days -- 83 more days than Milton's current average of 77 days.
For reference, the median list price across 145 active listings in Milton right now is $875,000.

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
$6,094/mo
$197,400 down
$789,600 loan
Principal & interest$5,121
Property tax (est.)$823
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated August 27, 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.