ClaudiaLavin
Buy
Property SearchSearch all available MLS listingsSet AlertsGet notified about new listingsNeighborhood GuidesExplore local communities & data
Lexington, MA
Arlington, MA
Waltham, MA
Somerville, MA
Burlington, MA
Belmont, MA
View All Neighborhoods →
Featured PropertiesBrowse our exclusive local listings
79 Bedford St
Sell
Home ValuationGet a free, instant estimateMy ListingsBrowse my active market properties
Insights
Resources
Local EventsEvents & local favorites near you
About
Meet the AgentMy background and experienceClient StoriesRead reviews from past clients
Contact Me
Buy
Property Search
Set Alerts
Neighborhood Guides
Lexington, MA
Lexington CenterMeriam HillMunroe HillEast LexingtonFollen HillNorth LexingtonFive FieldsSix Moon HillLiberty Heights
Arlington, MA
Waltham, MA
Somerville, MA
Burlington, MA
Belmont, MA
View All Neighborhoods →
Featured Properties
79 Bedford St
Sell
Home Valuation
My Listings
Insights
Resources
Local Events
About
Meet the Agent
Client Stories
Contact Me

Claudia Lavin

I'm Claudia Lavin Rodriguez, a Lexington, MA real estate agent helping first-time buyers, young professionals and families across Greater Boston — from first search to keys.

Explore

  • Home
  • About
  • Home Search
  • Set Alerts
  • My Active Listings
  • Featured Listings
  • Home Valuation
  • Insights
  • Testimonials
  • Contact
  • Privacy Policy

Contact

  • 7 Langley Road, Newton, MA, 02459
  • (603) 320-2906
  • claudialavin.re@gmail.com

Brokerage

Luxury Realty Partners

© 2026 Claudia Lavin. All rights reserved.
Equal Housing Opportunity. Information deemed reliable but not guaranteed.

  1. Home
  2. Listings
  3. 1066 Hillside St, Milton, MA 02186
Active
95 Days on market
1066 Hillside St Milton — Photo 1 of 39

1066 Hillside St Milton — Photo 1 of 39

$1,200,000

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$538/sqft
Local Avg (Milton)$559/sqft
4% BelowMarket Average

* Analysis is based on 24 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

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.

Full Milton, MA market report ZIP 02186 market data
Listing Provided By

Listing Agent: Bridget Conroy

Listing Office: Coldwell Banker Realty - Milton

MLS® Number: 73519606

Related Insights

View All
Massachusetts Closing Costs: Watch Prepaids & Escrow
Real Estate
Aug 5, 2026

Massachusetts Closing Costs: Watch Prepaids & Escrow

Why Massachusetts Home Prices Stay High in 2026
Real Estate
Jul 29, 2026

Why Massachusetts Home Prices Stay High in 2026

View All Insights

Browse More Homes in Milton

Explore other active listings in the area.

  • 29 Lawrence Rd
    $749,900
    29 Lawrence Rd
    Milton, MA
    4 bd2 ba1,492 sqft
  • 37 Nahanton Ave
    $839,000
    37 Nahanton Ave
Milton, MA
3 bd2 ba1,248 sqft
  • 50 Brush Hill Rd
    $749,900
    50 Brush Hill Rd
    Milton, MA
    3 bd2 ba1,746 sqft
  • 20 Fairbanks Rd
    $750,000
    20 Fairbanks Rd
    Milton, MA
    4 bd2 ba1,416 sqft
  • 24 Victory Avenue
    $1,299,000
    24 Victory Avenue
    Milton, MA
    5 bd3 ba2,980 sqft
  • 147 Canton Avenue
    $1,995,000
    147 Canton Avenue
    Milton, MA
    8 bd5 ba4,500 sqft