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Active Under Contract

105 Randolph Ave

Milton, MA 02186

Offered at$2,195,000

Residential · Active Under Contract · MLS #73565411
Listing Courtesy of Coldwell Banker Realty - Milton | Bridget Conroy

6Bedrooms
5Bathrooms
4,227Square feet
1910Year built

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MLS PIN data

About this home

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.

Property information

Details at a glance

Interior

Rooms
11
Heating
Hot Water, Heat Pump, Natural Gas, Electric
Cooling
Heat Pump
Flooring
Tile, Carpet, Hardwood, Flooring - Hardwood, Flooring - Wood
Fireplaces
4

Building

Style
Single Family Residence
Year built
1910
Garage
1
Parking
7
Foundation
Stone
Roof
Shingle

Land & utilities

Lot size
0.32 acres
Water
Public
Sewer
Public Sewer
Zoning
RB

Financial

Annual taxes
$18,727
Assessment year
2026

Listing history

Price and status timeline

No additional public listing history was supplied for this property.

Property value estimate

An informed starting point

Estimated value$2,271,279

Estimated range $2,091,655$2,450,902

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Automated estimates are not appraisals or guarantees of market value.

Comparable sales

Recent properties for context

Recent comparable sales are not available for this property.

Photo insights

Condition signals

Overall presentationaverage

Generated from listing photography; not a substitute for an inspection.

Local market context

How this home compares in Milton

MetricThis propertyMilton
List price$2,195,000$995,000121% above local
Price / sq ft$519$59713% below local
Days on market153456% below local
Explore homes in Milton

Active city listing statistics from MLS PIN as of September 5, 2026. Asking prices are not completed-sale values.

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Common questions

About 105 Randolph Ave

Can I schedule a private showing?

Yes. Request a tour of 105 Randolph Ave and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.