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.
For sale
$1,200,000
1066 Hillside St, Milton, MA 02186
4beds
2,232sqft
:
Get pre-qualified$7,345/mo
Single Family Residence
Built in 1965
0.46 Acres Lot
$1,194,500 Zestimate®
$538/sqft
$-- HOA
What's special
Generous layout
- 87 days |
- 1,051 |
- 37 |
Zillow last checked:
Listing updated:
Listed by:
Bridget Conroy 617-308-8073,
Coldwell Banker Realty - Milton 617-696-4430
Source: MLS PIN,MLS#: 73519606
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
Primary bathroom
- Features: No
Heating
- Baseboard, Oil
Cooling
- Window Unit(s)
Appliances
- Included: Range, Dishwasher, Refrigerator, Washer, Dryer
Features
- Basement: Full
- Number of fireplaces: 1
Interior area
- Total structure area: 2,232
- Total interior livable area: 2,232 sqft
- Finished area above ground: 2,232
Property
Parking
- Total spaces: 7
- Parking features: Attached, Off Street, Paved
- Attached garage spaces: 2
- Uncovered spaces: 5
Features
- Patio & porch: Deck, Patio
- Exterior features: Deck, Patio, Pool - Inground, Fenced Yard
- Has private pool: Yes
- Pool features: In Ground
- Fencing: Fenced
- Has view: Yes
- View description: Scenic View(s)
Lot
- Size: 0.46 Acres
- Features: Level, Sloped
Details
- Parcel number: 133840
- Zoning: RB
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Concrete Perimeter
- Roof: Shingle
Condition
- Year built: 1965
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: 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
HOA
- Has HOA: No
Location
- Region: Milton
Financial & listing details
- Price per square foot: $538/sqft
- Tax assessed value: $888,400
- Annual tax amount: $9,852
- Date on market: 5/14/2026
- Listing terms: Seller W/Participate
Estimated market value
$1,194,500
$1.13M - $1.25M
$5,250/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/15/2026 | Listed for sale | $1,200,000+194.8%$538/sqft |
Source: MLS PIN #73519606 Report a problem | ||
| 10/29/2010 | Sold | $407,000-5.3%$182/sqft |
Source: Public Record Report a problem | ||
| 9/9/2010 | Price change | $429,900-4.3%$193/sqft |
Source: Sally Koss #71045914 Report a problem | ||
| 6/8/2010 | Price change | $449,000-6.3%$201/sqft |
Source: Sally Koss #71045914 Report a problem | ||
| 5/5/2010 | Price change | $479,000-4%$215/sqft |
Source: Sally Koss #71045914 Report a problem | ||
| 3/13/2010 | Listed for sale | $499,000$224/sqft |
Source: Sally Koss #71045914 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $9,852 +3.9% | $888,400 +2.3% |
| 2024 | $9,481 +1.1% | $868,200 +5.6% |
| 2023 | $9,374 -0.2% | $822,300 +9.2% |
| 2022 | $9,394 +2.5% | $753,300 +8% |
| 2021 | $9,161 +0.6% | $697,700 +0.5% |
| 2020 | $9,104 +8.4% | $693,900 +8.9% |
| 2019 | $8,397 +13.5% | $637,100 +19% |
| 2018 | $7,397 +6.9% | $535,600 +5% |
| 2017 | $6,918 +7.5% | $510,200 +7% |
| 2016 | $6,437 -1% | $476,800 +2.3% |
| 2015 | $6,500 +1.1% | $466,300 +8.7% |
| 2014 | $6,432 +2% | $429,100 |
| 2013 | $6,308 +2.4% | $429,100 |
| 2012 | $6,158 -13.4% | $429,100 -15.1% |
| 2011 | $7,112 -0.8% | $505,500 -5.8% |
| 2010 | $7,166 +12.9% | $536,800 -0.7% |
| 2009 | $6,348 +3.9% | $540,700 -3.1% |
| 2008 | $6,111 +1% | $558,100 |
| 2007 | $6,050 +6.8% | $558,100 |
| 2006 | $5,665 +7.5% | $558,100 +11.6% |
| 2005 | $5,271 -0.1% | $500,100 +14.9% |
| 2004 | $5,276 +3.3% | $435,300 |
| 2003 | $5,106 -5.5% | $435,300 +35.9% |
| 2002 | $5,402 +22.7% | $320,200 +33.1% |
| 1999 | $4,404 | $240,500 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 02186
Nearby schools
GreatSchools rating
- 6/10Tucker Elementary SchoolGrades: PK-5Distance: 3.7 mi
- 8/10Charles S Pierce Middle SchoolGrades: 6-8Distance: 3.7 mi
- 10/10Milton High SchoolGrades: 9-12Distance: 3.2 mi
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A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
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