1066 Hillside St Milton — Photo 1 of 39
Recent Drop: $213,000
$987,000
Investment Analysis — 1066 Hillside St
Milton, MA 02186
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 4-bedroom in 02186 carries an estimated $3,390/mo in gross rent — about a 2.13% cap rate and $21,065/yr in estimated NOI at the $987,000 list price. Adjust every assumption in the calculator below.
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.
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.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Range • Dishwasher • Refrigerator • Washer • Dryer
Neighborhood
Public Transportation • Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails
Geography
Property History
$987,000
Was $1,200,000
Aug 23, 2026
MLS® 73519606
$1,200,000
May 14, 2026
MLS® 73519606
$407,000
Sep 17, 2010
MLS® 71045914
$429,900
Mar 11, 2010
MLS® 71045914
Listing Agent: Bridget Conroy
Listing Office: Coldwell Banker Realty - Milton
MLS® Number: 73519606