Recently Listed Open House 11/13 12pm - 1pm
114 Hillside Street
Milton, MA, 02186 $ 2,700,000
Bedrooms3 Baths3.1 Sq 5,039 Monthly Estimate*
$ 18,648
for $2,700,000 with 3 bedrooms and 3 full baths, 1 half bath. This 5,039 square foot home was built in 2026 on a lot size of 1.07.
There's something wonderful about the prospect of a brand-new home. The anticipation of moving in, settling into familiar routines in new spaces, and watching a house gradually become your own. Everything is ahead of you. At 114 Hillside Street, there's plenty to look forward to. Set among the trees in Milton's Scotts Woods, this newly constructed home makes a striking first impression. Its contemporary architecture is clean and confident, with dramatic windows, handsome exterior details, and a setting that feels wonderfully private. There’s a sense of playfulness in how the house sits among the trees. From inside, you might find yourself feeling as if you've escaped to a treehouse. Albeit a rather spectacular one. Inside, approximately 5,000 square feet spans three finished levels. A soaring two-story living room, expansive windows, wide-plank flooring, and warm, carefully selected finishes define the home's character. The kitchen features a suite of Thermador appliances, while a separate family room, office, and den provide flexibility for everyday life. Upstairs, the generous primary suite opens to an Ipe deck and includes a luxurious ensuite bath. A finished lower level with an expansive recreation room and custom wet bar offers even more room to gather and entertain. There's a certain magic to living among the treetops. Situated among other distinctive estate-style homes in Milton's Scotts Woods, 114 Hillside enjoys a private, wooded setting. Tall windows frame the trees, the second-floor sitting area overlooks the living room below, and the private balcony feels like a perch above it all. For all its woodland charm, the location is wonderfully practical. Milton's shops, restaurants, Milton Academy, top-tier public schools, and the Blue Hills Reservation are close, with Boston's amenities and attractions easily accessible.114 Hillside Street is ready for its first chapter. The rest is yours to write. NOTE: Paving has been completed since the photos were taken, and landscaping is underway.
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Open House
11/13/2026 12:00 PM - 1:00 PM
11/14/2026 12:00 PM - 1:30 PM
11/15/2026 12:00 PM - 1:30 PM
114 Hillside Street Milton, MA
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
Affordability Calculator
- Monthly Principal & Interest
- $18,648
- Monthly Property Taxes
- $8,333,333
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Milton, MA
Average List Price $2,515,627
Percent of Sale Price 7%
About Milton, MA 27,252 Population
4% Since 2002
$ 123,529 Median Income
42.17 Median Age
36% Households with Children
Trends Information provided by ATTOM Data Solutions.
Neighborhood & Schools
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Pricing History| Date | Price | Price Change | Description |
|---|
| 11/11/2026 | $2,700,000 | | Listed Price |