105 Randolph Ave, Milton, MA 02186
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$2,195,000
6 Beds
5 Baths
4227 SQFT
0.32 Acre
HOA: N/A

Property Description

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 Details tap to expand

Amenities

  • Bike Path
  • Conservation Area
  • Golf Course
  • Highway Access
  • House of Worship
  • Marina
  • Medical Facility
  • Park
  • Public School
  • Public Transportation
  • Shopping
  • Swimming Pool
  • T-Station
  • Tennis Court
  • University
  • Walk/Jog Trails

Kitchen, Dining, and Appliances

  • Kitchen Dimensions: 16X23
  • Balcony / Deck, Bathroom - Half, Breakfast Bar / Nook, Closet/Cabinets - Custom Built, Countertops - Stone/Granite/Solid, Deck - Exterior, Dining Area, Exterior Access, Flooring - Hardwood, Lighting - Overhead, Open Floor Plan, Wet bar
  • Dishwasher, Disposal, Dryer, Range, Refrigerator, Vent Hood, Wall Oven, Washer
  • Dining Room Dimensions: 14'10"X15'8"
  • Dining Room Level: First Floor
  • Dining Room Features: Exterior Access, Fireplace, Flooring - Hardwood, Lighting - Sconce, Open Floor Plan

Bathrooms

  • Full Baths: 3
  • Half Baths 2
  • Master Bath: 1
  • Bathroom 1 Dimensions: 6'6"X4'2"
  • Bathroom 1 Level: First Floor
  • Bathroom 1 Features: Bathroom - Half
  • Bathroom 2 Dimensions: 6'10"X7'7"
  • Bathroom 2 Level: Second Floor
  • Bathroom 2 Features: Bathroom - Double Vanity/Sink, Bathroom - Full
  • Bathroom 3 Dimensions: 8'2"X8'4"
  • Bathroom 3 Level: Second Floor
  • Bathroom 3 Features: Bathroom - Full

Bedrooms

  • Bedrooms: 6
  • Master Bedroom Dimensions: 30'10"X15'8"
  • Master Bedroom Level: Second Floor
  • Master Bedroom Features: Bathroom - Full, Closet - Double, Closet - Walk-in, Closet/Cabinets - Custom Built, Lighting - Sconce, Window(s) - Bay/Bow/Box
  • Bedroom 2 Dimensions: 12'1"X15'1"
  • Bedroom 2 Level: Second Floor
  • Master Bedroom Features: Closet, Flooring - Hardwood, Lighting - Sconce
  • Bedroom 3 Dimensions: 11'2"X12'8"
  • Bedroom 3 Level: Second Floor
  • Master Bedroom Features: Closet

Other Rooms

  • Total Rooms: 11
  • Living Room Dimensions: 13'10"X10'1"
  • Living Room Level: First Floor
  • Living Room Features: Closet, Closet/Cabinets - Custom Built, Crown Molding, Fireplace, Flooring - Hardwood, Lighting - Sconce
  • Family Room Dimensions: 19'10"X14'10"
  • Family Room Level: First Floor
  • Family Room Features: Closet, Closet/Cabinets - Custom Built, Exterior Access, Fireplace, Flooring - Hardwood, Lighting - Sconce, Open Floor Plan, Skylight, Window(s) - Bay/Bow/Box
  • Laundry Room Features: Concrete Floor, Full, Interior Access, Partially Finished, Sump Pump, Walk Out

Utilities

  • Heating: Electric, Gas, Heat Pump, Hot Water Radiators
  • Heat Zones: 10
  • Hot Water: Natural Gas
  • Cooling: Heat Pump
  • Cooling Zones: 10
  • Utility Connections: for Electric Dryer, for Gas Range
  • Water: City/Town Water
  • Sewer: City/Town Sewer

Garage & Parking

  • Garage Parking: Detached, Side Entry
  • Garage Spaces: 1
  • Parking Features: Improved Driveway, Off-Street
  • Parking Spaces: 7

Interior Features

  • Square Feet: 4227
  • Fireplaces: 4
  • Accessability Features: No

Construction

  • Year Built: 1910
  • Type: Detached
  • Style: Colonial
  • Construction Type: Frame
  • Foundation Info: Fieldstone
  • Roof Material: Asphalt/Fiberglass Shingles
  • Flooring Type: Hardwood, Tile, Wall to Wall Carpet
  • Lead Paint: Unknown
  • Warranty: No

Exterior & Lot

  • Lot Description: Corner, Level
  • Exterior Features: Deck, Decorative Lighting, Fenced Yard, Garden Area, Hot Tub/Spa, Patio, Pool - Inground Heated, Porch, Professional Landscaping, Stone Wall, Storage Shed
  • Road Type: Public

Other Information

  • MLS ID# 73565411
  • Last Updated: 08/19/26
  • HOA: No
  • Reqd Own Association: Unknown
  • Terms: Seller W/Participate

Property History tap to expand

Date Event Price Price/Sq Ft Source
08/19/2026New$2,195,000$519MLSPIN

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Seller's Representative: Bridget Conroy, Coldwell Banker Realty - Milton
Sub Agent Compensation: n/a
Buyer Agent Compensation: n/a
Facilitator Compensation: n/a
Compensation Based On: n/a
Sub-Agency Relationship Offered: No

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MLS PIN data last updated at 2026-08-19 09:55:00

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