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1066 Hillside St, Milton MA 02186

Milton, MA 02186
$1,200,000
Est. $7,089/month
4
Beds
1.5
Baths
2,232
Sq Ft
$538
Price/Sq Ft
0.46
Acres
1965
Year Built
2
Garage Spaces
57
Days on Market
Active Listed May 14, 2026 • MLS# 73519606 Copied! • Updated Jun 12, 2026

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.

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Recently Sold Nearby

Property History

Property Timeline

🏠
Listed for Sale
May 15, 2026
$1,200,000
Original listing
Agent: Bridget Conroy Office: Coldwell Banker Realty - Milton

Tax History

Year Taxes Assessment
2025 $9,852 $888,400

Financial Details

Annual Property Tax
$9,852
Tax Year 2025
Assessed Value
$888,400

Facts & Features

2 Car Garage

Home Facts

Type Residential
Style Single Family Residence
Year Built 1965
Living Area 2,232 sq ft
Lot Size 0.46 acres
Bedrooms 4
Full Baths 1
Half Baths 1
Total Rooms 9

Interior

Heating Baseboard, Oil
Cooling Window Unit(s)
Flooring None
Appliances Range, Dishwasher, Refrigerator, Washer, Dryer
Fireplace None
Fireplaces 1
Basement Full
Laundry None
Features None

Exterior

Construction Frame
Architecture Colonial
Roof Shingle
Features Deck, Patio, Pool - Inground, Fenced Yard
Pool In Ground
Spa None
Fencing Fenced
Patio/Porch Deck, Patio
Garage Spaces 2
Has Garage Yes
Features Attached, Off Street, Paved
Total Spaces 7
Electric None
Water Public
Sewer Public Sewer
Gas None
Other None
Annual Tax $9,852
Assessed Value $888,400
Fee Includes None
Amenities None
Optional Fee Includes None
Seller Disclosures The Pool Is Not Functioning. It Needs A New Liner And Wasnt Closed Down Properly Last Season. The Wood Floors Have Pet Damage. A Few Of The Windows Arent Working Or Have Cracked Glass.
Possession None
Accepted Financing Seller W/participate
Structure Type []
Sq Ft Source Public Record
Documents None
County Norfolk
Total market time (incl. prior listings) 29 days

Property Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1965
Bedrooms
4
Full Bathrooms
1
Half Bathrooms
1
Living Area
2,232 sq ft
Total Rooms
9

Room Details

Other Floor

Bathroom1
Bedroom5
Bedroom4
Bedroom3
Dining Room
Kitchen
Bathroom2
Bedroom2
Living Room
Bathroom3
Master Bedroom
Office
Family Room
Master Bathroom
No

Interior Features

Flooring:
Appliances: Range, Dishwasher, Refrigerator, Washer, Dryer
Interior Features:
Windows:
Basement: Full
Laundry:
Security:

Construction & Materials

Style: Colonial
Year Built: 1965
Structure Type:
Exterior Materials: Frame
Roof: Shingle
Foundation: Concrete Perimeter

Heating, Cooling & Utilities

Heating: Baseboard, Oil
Heating Zones: 1
Cooling: Window Unit(s)
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features: Deck, Patio, Pool - Inground, Fenced Yard
Patio & Porch: Deck, Patio
Fencing: Fenced
Other Structures:
Lot Features: Level, Sloped
Road Surface:

Parking & Garage

Garage Spaces: 2
Garage Type: Attached
Total Parking Spaces: 7
Parking Features: Attached, Off Street, Paved

Special Features

Fireplaces: 1
Fireplace Type:
Pool: Private Pool
Pool Features: In Ground
View: Yes
View Type: Scenic View(s)
Community Amenities: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, University

Nearby Schools

School information not available for this location.

Monthly Payment Calculator

Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%

Monthly Payment Breakdown

Principal & Interest $0
Property Tax $821
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo

Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Location

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Neighborhood

1066 Hillside St, Milton MA 02186

Milton, MA 02186

Listing Information

Listing Agent Bridget Conroy
Listing Office Coldwell Banker Realty - Milton
Office Phone 617-696-4430
Agent MLS ID CN230868
Office MLS ID AN6223
Listing Data Updated Jun 12, 2026 12:47 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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