Recently Listed Open House 8/21 1pm - 2pm
105 Randolph Ave
Milton, MA, 02186 $ 2,195,000
Bedrooms6 Baths3.2 Sq 4,227 Monthly Estimate*
$ 13,859
for $2,195,000 with 6 bedrooms and 3 full baths, 2 half baths. This 4,227 square foot home was built in 1910 on a lot size of 0.32.
This is the Milton Hill home you have been waiting for! Character abounds and the gardens are stunning. The layout flexes with whatever stage of life walks through it. The first floor is anchored by fireplaces. There is a gas fireplace in each of the living spaces and a wood burning fireplace in the dining room, so the main level has four different places to gather and each one has a reason to sit down. Ceilings are high, windows are tall, and the original detail is still here. The kitchen is ready for its next chapter, and the footprint is the gift. There is genuine room to work with, enough for the island, the second sink, and the double ovens without borrowing an inch from anywhere else. Six bedrooms and four baths across three levels give every generation a floor of its own, whether that means a guest suite, a home office with a door that closes, a playroom, or all three. Wood floors run under the second floor carpeting. The primary has its own bath. The rest of the baths are all in working order and ready to take whatever finishes you have in mind. The systems have been handled. The home has been converted to gas, and mini splits run throughout, so every level stays comfortable through a July afternoon and a January night without a single window unit. Then there is the yard, and it is the moment. Water spills over a waterfall into the pool, the flower gardens frame it, and the stone tower of St. Michael's Church rises just beyond the property line. It reads like a courtyard in Europe and it sits on one of Milton's most recognizable streets. The equipment behind it is all new, with a new filter system, a new heater, and new pumps, so the season starts when you say it does and runs as long as you want it to. The gardens have been planted and tended for years, the kind of maturity you cannot buy new. They climb the stone terraces behind the pool with steps winding up through the beds. A deck off the back steps down to the terrace and the pool patio, and a walkout below sits a few steps from the water with a full fifth bathroom right there, so nobody tracks through the house in a wet suit. Pines and cedars close the property in on all sides. Outdoor living here is not a patio and a grill. It is a destination. Minutes to Milton Village, the Trolley to the Red Line, Milton Academy, Cunningham Park, the Blue Hills, and downtown Boston.
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Open House
8/21/2026 1:00 PM - 2:00 PM
8/22/2026 10:00 AM - 11:30 AM
105 Randolph Ave 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
List ByBridget ConroyListing Agent
Coldwell Banker Realty - MiltonBroker
Affordability Calculator
- Monthly Principal & Interest
- $13,859
- Monthly Property Taxes
- $1,561
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% 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 $2,221,315
Percent of Sale Price 1%
About Milton, MA 27,252 Population
4% Since 2002
$ 123,529 Median Income
42.17 Median Age
36% Households with Children
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Pricing History| Date | Price | Price Change | Description |
|---|
| 8/19/2026 | $2,195,000 | | Listed Price |