1066 Hillside St, Milton MA 02186
Milton, MA 02186
$1,200,000
Est. $7,089/month
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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
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 05/15/2026 | 🏠 Listed for Sale | $1,200,000 | - | - | Original listing |
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
Parking
Garage Spaces
2
Has Garage
Yes
Features
Attached, Off Street, Paved
Total Spaces
7
Utilities
Electric
None
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$9,852
Assessed Value
$888,400
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
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.
Additional Details
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
Floor Layout
Interactive room guide
Floor Layout
Finished Area
2,232 sq ft above grade
FeaturesNo
Display Options
Outdoor Areas
PoolIn Ground
Patio & porchDeck, Patio
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
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 District
Milton School District local
A+
School Safety
2024-25
0.3%
Low
0.2%
Suspensions
0.1%
In-School
0.1%
Emergency
5.2% below state avg
Elementary Schools
3 schools
Thacher Montessori School
1.2 mi
Grades PK-08
Blue Hill Montessori School
1.8 mi
Grades PK-K
Judge Rotenberg School
2.0 mi
Grades PK-12
Middle Schools
3 schools
A
William H. Galvin Middle School
2.0 mi
|
#55 of 352
|
Score: 55.8
Improved 7 spots from last year
-2.4 below state avg
716 students
Diverse
Grades 06-08
C-
Randolph Community Middle School
2.7 mi
|
#295 of 352
|
Score: 31.8
Dropped 48 spots from last year
-26.4 below state avg
640 students
Diverse
Diverse Student Body
Grades 06-08
Lumen Verum Academy
3.4 mi
Grades 06-08
High Schools
3 schools
B+
Blue Hills Regional Vocational Technical School
1.6 mi
|
#132 of 346
|
Score: 57.1
Dropped 21 spots from last year
-1.1 below state avg
910 students
Diverse
Strong AP Program
High Graduation Rate
Career Tech Programs
College Ready Curriculum
Grades 09-12
Beacon Scholastic Academy
2.6 mi
Grades 06-12
A+
Milton High School
3.2 mi
|
#22 of 346
|
Score: 73.1
Improved 4 spots from last year
+14.9 above state avg
1,083 students
Diverse
21 sports
• 2,432 athletes
Strong AP Program
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 09-12
Learn about these ratings
Monthly Payment Calculator
Monthly Payment
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Principal, interest, taxes & insurance
Loan Amount
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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
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Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo
Payment Over Time
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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