NickBiondo
Buy
Property SearchSearch all available MLS listingsSet AlertsGet notified about new listingsNeighborhood GuidesExplore local communities & data
Needham, MA
Wellesley, MA
Dover, MA
Westwood, MA
Dedham, MA
Natick, MA
View All Neighborhoods →
Featured PropertiesBrowse our exclusive local listings
9 Weld St
27 Harold W Bishop B...
45 Circuit Rd
Sell
Home ValuationGet a free, instant estimateMy ListingsBrowse my active market properties
Insights
Resources
ResourcesHelpful guides and toolsLocal EventsEvents & local favorites near you
About
Meet the AgentMy background and experience
Contact Me
Buy
Property Search
Set Alerts
Neighborhood Guides
Needham, MA
Needham CenterNeedham HeightsNeedham JunctionCharles River VillageBirds HillBroadmeadow
Wellesley, MA
Dover, MA
Westwood, MA
Dedham, MA
Natick, MA
View All Neighborhoods →
Featured Properties
9 Weld St
27 Harold W Bishop B...
45 Circuit Rd
Sell
Home Valuation
My Listings
Insights
Resources
Resources
Local Events
About
Meet the Agent
Contact Me

Nick Biondo

I'm Nick Biondo, a Needham, MA real estate agent helping young and growing families find the right suburban home across MetroWest Boston — from first search to closing.

Explore

  • Home
  • About
  • Home Search
  • Set Alerts
  • My Active Listings
  • Featured Listings
  • Home Valuation
  • Insights
  • Resources
  • Contact
  • Privacy Policy

Contact

  • 10 Lincoln St, Newton, MA, 02461
  • (480) 540-2772
  • nick@commonwealthstandard.com

Brokerage

Commonwealth Standard Realty Advisors

© 2026 Nick Biondo. All rights reserved.
Equal Housing Opportunity. Information deemed reliable but not guaranteed.

  1. Home
  2. Listings
  3. 105 Randolph Ave, Milton, MA 02186
Active
7 Days on market
105 Randolph Ave Milton — Photo 1 of 35

105 Randolph Ave Milton — Photo 1 of 35

$2,195,000

105 Randolph Ave, Milton, MA 02186

Milton, MA 02186 — Milton Hill

Beds

6

Baths

4

SqFt

4,227

Style

Single Family

Built

1910

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.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$519/sqft
Local Avg (Milton)$599/sqft
13% BelowMarket Average

* Analysis is based on 23 actively listed and recently sold comparable properties strictly within Milton, MA.

Property Details

Financials

Original Price$2,195,000
Annual Taxes$18,727

Parking

Garage1
Off-Street7

Interior Specifications

Total Rooms11
Fireplaces4
FlooringTile, Carpet, Hardwood, Flooring - Hardwood, Flooring - Wood
BasementFull, Partially Finished, Walk-Out Access, Interior Entry, Sump Pump, Concrete

Climate & Utilities

HeatingHot Water, Heat Pump, Natural Gas, Electric
CoolingHeat Pump
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationStone
ZoningRB

Property & Lot

Acres0.32
SqFt Lot14,022
Lot FeaturesCorner Lot, Level

Amenities & Appliances

Gas Water Heater • Range • Oven • Dishwasher • Disposal • Refrigerator • Washer • Dryer • Range Hood

Neighborhood

Public Transportation • Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails

Geography

Floorplan Breakdown

Structural Layout

Third
Bedroom 5
Second
Master BedroomBedroom 2Bedroom 3Bedroom 4Bathroom 2Bathroom 3
First
Living RoomDining RoomFamily RoomBathroom 1
Main,First
Kitchen
Living Room
Lvl First

13.8 x 10.11

Closet, Closet/Cabinets - Custom Built, Flooring - Hardwood, Lighting - Sconce, Crown Molding

Dining Room
Lvl First

14.8 x 15.7

Flooring - Hardwood, Exterior Access, Open Floorplan, Lighting - Sconce

Kitchen
Lvl Main,First

16 x 23

Bathroom - Half, Closet/Cabinets - Custom Built, Flooring - Hardwood, Dining Area, Balcony / Deck, Countertops - Stone/Granite/Solid, Wet Bar, Breakfast Bar / Nook, Deck - Exterior, Exterior Access, Open Floorplan, Lighting - Overhead

Family Room
Lvl First

19.8 x 14.8

Skylight, Closet, Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Bay/Bow/Box, Exterior Access, Open Floorplan, Lighting - Sconce

Master Bedroom
Lvl Second

30.8 x 15.7

Bathroom - Full, Walk-In Closet(s), Closet/Cabinets - Custom Built, Window(s) - Bay/Bow/Box, Lighting - Sconce, Closet - Double

Bedroom 2
Lvl Second

12.1 x 15.11

Bedroom 3
Lvl Second

11.2 x 12.7

Closet

Bedroom 4
Lvl Second

12.2 x 9.9

Skylight, Vaulted Ceiling(s), Closet, Flooring - Hardwood, Flooring - Wall to Wall Carpet, Half Vaulted Ceiling(s)

Bedroom 5
Lvl Third

20.9 x 12.3

Walk-In Closet(s)

Bathroom 1
Lvl First

6.5 x 4.2

Bathroom - Half

Bathroom 2
Lvl Second

6.8 x 7.6

Bathroom - Full, Bathroom - Double Vanity/Sink

Bathroom 3
Lvl Second

8.2 x 8.3

Bathroom - Full

Population

28,735

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$188K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

15.1%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Norfolk County

1,189 housing units permitted in the last 12 months (+21% vs the prior 12 months) — 706 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 4,227 sq ft principal dwelling). Lot size: 14,022 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Full Milton, MA market report ZIP 02186 market data
Listing Provided By

Listing Agent: Bridget Conroy

Listing Office: Coldwell Banker Realty - Milton

MLS® Number: 73565411

Related Insights

View All
Massachusetts Fall Housing Market Gives Buyers Room
Real Estate
Aug 17, 2026

Massachusetts Fall Housing Market Gives Buyers Room

Closing Costs in MA for Buyers and Sellers
Real Estate
Aug 3, 2026

Closing Costs in MA for Buyers and Sellers

MetroWest MA Buyers Face High Prices and Fast Sales
Real Estate
Jul 27, 2026

MetroWest MA Buyers Face High Prices and Fast Sales

View All Insights

Browse More Homes in Milton

Explore other active listings in the area.

  • 355 Brush Hill Road
    $1,225,000
    355 Brush Hill Road
    Milton, MA
    3 bd3 ba3,182 sqft
  • 1066 Hillside St
    $987,000
    1066 Hillside St
Milton, MA
4 bd2 ba2,232 sqft
  • 165 Thacher
    $800,000
    165 Thacher
    Milton, MA
    2 bd2 ba1,574 sqft
  • 1200 Brook Road
    $895,000
    1200 Brook Road
    Milton, MA
    3 bd2 ba1,760 sqft
  • 45 Wendell Park
    $1,099,000
    45 Wendell Park
    Milton, MA
    4 bd2 ba2,100 sqft
  • 52 Meagher Ave
    $650,000
    52 Meagher Ave
    Milton, MA
    3 bd2 ba1,123 sqft