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Street View
$2,195,000
Monthly Est:$10,925
6 Beds
- 5 Baths
3 full baths + 2 half baths
4,227sqft
105 Randolph Ave, Milton, MA 02186
$2,195,000
$10,925/moEst:
Get Pre-Approved
Single Family Residence
Built in 1910
$-- HOA
0.32 acre lot
$519/sq.ft
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.
- Houzeo last checked: 1 hour ago
- Listing updated: August 26, 2026 at 4:38 pm
- Listing Provided by: Bridget Conroy (617) 308-8073 | Coldwell Banker Realty - Milton (617) 696-4430
- Source: MLS Property Information Network-MA | MLS#: 73565411

Property Details
Status
Active Under Contract
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1910
HOA Fees
-
Finished Area
4,227 sqft
Lot Size
0.32 acre lot
Basement Area
- sqft
MLS Name
MLS Property Information Network
MLS Number
73565411
MLS Status
Contingent
Days on Market
49

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 6
Bathrooms: 5
Interior
Window Features
Skylight(s)
Exterior Features
Balcony / Deck, Porch, Porch Enclosed, Deck, Patio, Pool Inground Heated, Hot Tub/spa, Storage, Professional Landscaping, Decorative Lighting, Fenced Yard, Garden, Stone Wall
Sewer
Public Sewer
Heating
Hot Water, Heat Pump, Natural Gas, Electric
Flooring
Tile, Carpet, Hardwood, Flooring Hardwood, Flooring Wood
Interior Features
Closet, Bedroom, Entry Hall, Sun Room, Wet Bar
Appliances
Gas Water Heater, Range, Oven, Dishwasher, Disposal, Refrigerator, Washer, Dryer, Range Hood
Cooling
Heat Pump
Construction
Year Built
Year Built: 1910
Home type
Single Family Residence
Construction Materials
Frame
Foundation Details
Stone
Architectural Style
Colonial
Roof
Shingle
Utilities & Energy
Utilities
For Gas Range, For Electric Dryer
Fireplace Features
Dining Room, Family Room, Living Room, Bedroom
Parking Features
Detached, Garage Faces Side, Off Street, Driveway
Basement
Full, Partially Finished, Walk Out Access, Interior Entry, Sump Pump, Concrete
Laundry Features
In Basement, Electric Dryer Hookup
Water Source
Public
Pool Features
Pool Inground Heated
Other Features
Subdivision Name
Milton Hill
Patio And Porch Features
Porch, Porch Enclosed, Deck, Patio
Community Features
Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House Of Worship, Marina, Public School, T Station, University
Disclosures
Boiler Replaced In 2002 When Home Was Converted To Gas. Exterior Painted In 2026. Pool Filter, Pump And Heater Replaced In 2025. Roof Replaced In 2020. Fireplace In Bedroom Is Not Currently In Use But Can Be Made To Function. Microwave Is Not Working. Some Of The Windows Are Not Working Properly.
Lot Features
Corner Lot, Level
Price History
| Date | Event | Price |
|---|---|---|
08/26/2026 Source: | Contingent (Active Under Contract) | $2,195,000 $519/sqft |
08/19/2026 Source: | Listed for Sale | $2,195,000 $519/sqft |
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Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Oct 08, 2026, 09:00AM. The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.
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