105 Randolph Ave Milton MA 02186 | MLS #73565411

105 Randolph Ave
Milton, MA, 02186
$2,195,000
6 Beds
4 Baths
4,227 SqFt
0.32 Acres
$2,195,000
105 Randolph Ave
Milton, MA, 02186
MLS #73565411 image #0
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

Price:
$2,195,000
MLS #:
73565411
Status:
Active Under Contract
Beds:
6
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Milton Hill
Neighborhood:
miltonhill
Listed Date:
Aug 19, 2026
Finished Sq Ft:
4,227
Total Sq Ft:
4,227
Lot Size:
14,022 sqft / 0.32 acres (approx)
Year Built:
1910
ColonialPoolTennisMilton HillMiltonhillMilton HillGloverPierceMilton High

Schools

Elementary School:
Glover
Middle School:
Pierce
High School:
Milton High

Interior

Above Grade Finished Area
3896
Appliances
Gas Water Heater, Range, Oven, Dishwasher, Disposal, Refrigerator, Washer, Dryer, Range Hood
Bathrooms
3 Full Bathrooms, 2 Half Bathrooms
Below Grade Finished Area
331
Cooling
Heat Pump
Fireplaces Total
4
Flooring
Tile, Carpet, Hardwood, Flooring – Hardwood, Flooring – Wood
Heating
Hot Water, Heat Pump, Natural Gas, Electric
Interior Features
Closet, Bedroom, Entry Hall, Sun Room, Wet Bar
Laundry Features
In Basement, Electric Dryer Hookup

Exterior

Accessibility Features
No
Architectural Style
Colonial
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
Construction Materials
Frame
Covered Spaces
1
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
Fencing
Fenced
Garage Spaces
1
Lot Features
Corner Lot, Level
Open Parking Spaces
6
Open Parking YN
1
Parking Features
Detached, Garage Faces Side, Off Street, Driveway
Parking Spots
7
Parking Total
7
Patio And Porch Features
Porch, Porch – Enclosed, Deck, Patio
Roof
Shingle
Spa Features
Private
Window Features
Skylight(s)

Financial

Tax Year
2026
Taxes
$18,727
Need more info?
Ask a Question
Ready to go see it?
Schedule a Showing
Marie Andrews

Marie Andrews

RealtorĀ®, Broker/Owner, GBREB, Notary Public

Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…

More About Marie

Mortgage Calculator

 

Map

Current real estate data for Single Family in Milton as of Aug 31, 2026
55
Single Family Listed
85
Avg DOM
566
Avg $ / SqFt
$2,071,478
Avg List Price

Community

Similar Listings Nearby

broker reciprocity
MLS# 73519240broker reciprocity
135 Street Milton
Milton, MA

$2,725,000

3.4 miles away

broker reciprocity
MLS# 73513398broker reciprocity
151 Dorchester Street
Quincy, MA

$2,690,000

3.8 miles away

broker reciprocity
MLS# 73511761broker reciprocity
244 L St # 3
Boston, MA

$2,399,000

4.8 miles away

broker reciprocity
MLS# 73530127broker reciprocity
24 Sigourney St # 2
Boston, MA

$2,295,000

3.4 miles away

broker reciprocity
MLS# 73545367broker reciprocity
181 I Street
Boston, MA

$2,285,000

4.8 miles away

broker reciprocity
MLS# 73568180broker reciprocity
5 Moss Hill Rd
Boston, MA

$2,249,999

4.3 miles away

broker reciprocity
MLS# 73533526broker reciprocity
84 Post Island Road
Quincy, MA

$2,249,900

4.8 miles away

broker reciprocity
MLS# 73524195broker reciprocity
2 Brownson Terrace
Boston, MA

$2,195,000

3.9 miles away

broker reciprocity
MLS# 73528328broker reciprocity
145 Dorchester St
Quincy, MA

$2,150,000

3.8 miles away

Property Summary

    Located in the Milton Hill subdivision, 105 Randolph Ave Milton MA is a Single Family for sale in Milton, MA, 02186. It is listed for $2,195,000 and features 6 beds, 4 baths, and has approximately 4,227 square feet of living space, and was originally constructed in 1910. The current price per square foot is $519. The average price per square foot for Single Family listings in Milton is $566. The average listing price for Single Family in Milton is $2,071,478. To schedule a showing of MLS#73565411 at 105 Randolph Ave in Milton, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
105 Randolph Ave
Milton, MA