1066 Hillside St, Milton, MA, 02186
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.
Getting Around
Car-Dependent
Minimal Transit
Somewhat BikeableSchools
Construction
Condition
- Year built: 1965
Materials
- Foundation: Concrete Perimeter
- Roof: Shingle
- Construction materials: Frame
Type & Style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Range,Dishwasher,Refrigerator,Washer,Dryer
Basement
- Has basement: Yes
- Basement: Full
Bedrooms & Bathrooms
- Bedrooms: 4
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
Features
- Number of fireplaces: 1
- Fireplace: Yes
- Finished area above ground: 2,232
Heating & Cooling
- Heating features: Baseboard,Oil
- Cooling features: Window Unit(s)
Interior Area
- Total structure area: 2,232
- Total interior livable area: 2,232 sqft
Master Bathroom
- Features: No
Property
Details
- Parcel number: 133840
- Zoning: RB
Features
- Private pool: Yes
- Pool features: In Ground
- Patio & porch: Deck,Patio
- Exterior features: Deck,Patio,Pool - Inground,Fenced Yard
- Fencing: Fenced
- Has view: Yes
- View description: Scenic View(s)
Lot
- Lot size: 0.46 Acres
- Features: Level,Sloped
Parking
- Total spaces: 7
- Parking features: Attached,Off Street,Paved
- Has garage: Yes
- Attached garage spaces: 2
- Covered spaces: 2
- Has uncovered spaces: Yes
- Uncovered spaces: 5
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Tsunami
How This Home’s Risks Compare
FEMA Declared Disasters Across Massachusetts Counties
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $6,067 | $72,804 |
| Home Insurance * | $290 | $3,480 |
| Property Taxes | $1,087 | $13,044 |
| Electricity | $440 | $5,281 |
| Total | $7,884 | $94,608 |
Income You'd Need if You Spent...
Massachusetts FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-05-15 | Listed for sale | $1,200,000 |
| 2010-10-29 | Sold | $407,000 |
| 2010-09-09 | Price change | $429,900 |
| 2010-06-08 | Price change | $449,000 |
| 2010-05-05 | Price change | $479,000 |
| 2010-03-13 | Listed for sale | $499,000 |
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