
1066 Hillside St Milton — Photo 1 of 39
Recent Drop: $213,000
$987,000
1066 Hillside St, Milton, MA 02186
Milton, MA 02186
Beds
4
Baths
1.5
SqFt
2,232
Style
Single Family
Built
1965
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.
Market Value Analysis
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Milton, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Range • Dishwasher • Refrigerator • Washer • Dryer
Neighborhood
Public Transportation • Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails
Geography
Property History
$987,000
Was $1,200,000
Aug 23, 2026
MLS® 73519606
$1,200,000
May 14, 2026
MLS® 73519606
$407,000
Sep 17, 2010
MLS® 71045914
$429,900
Mar 11, 2010
MLS® 71045914
Population
28,735
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$188K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
15.1%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Norfolk County
1,524 housing units permitted in the last 12 months (+52% vs the prior 12 months) — 1,030 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '26)
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 2,232 sq ft principal dwelling). Lot size: 19,998 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Bridget Conroy
Listing Office: Coldwell Banker Realty - Milton
MLS® Number: 73519606
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