Active
118 Days on market
1066 Hillside St Milton — Photo 1 of 39

1066 Hillside St Milton — Photo 1 of 39

Recent Drop: $213,000

$1,200,000
$987,000

$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

This Property
Size (SqFt) →Price →
This Property$442/sqft
Local Avg (Milton)$561/sqft
21% BelowMarket Average

* Analysis is based on 23 actively listed and recently sold comparable properties strictly within Milton, MA.

Property Details

Financials

Original Price$1,200,000
Annual Taxes$9,852

Parking

Garage2
Off-Street7

Interior Specifications

Total Rooms9
Fireplaces1
Flooring--
BasementFull

Climate & Utilities

HeatingBaseboard, Oil
CoolingWindow Unit(s)
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningRB

Property & Lot

Acres0.46
SqFt Lot19,998
Lot FeaturesLevel, Sloped

Amenities & Appliances

Range • Dishwasher • Refrigerator • Washer • Dryer

Neighborhood

Public Transportation • Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails

Geography

Property History

Price Drop
$987,000

Was $1,200,000

Aug 23, 2026

MLS® 73519606

Listed
$1,200,000

May 14, 2026

MLS® 73519606

Sold
$407,000

Sep 17, 2010

MLS® 71045914

Listed
$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

1,189 housing units permitted in the last 12 months (+21% vs the prior 12 months) — 706 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '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 Provided By

Listing Agent: Bridget Conroy

Listing Office: Coldwell Banker Realty - Milton

MLS® Number: 73519606

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