Active

128 Days on market

55 Parkwood Drive Milton — Photo 1 of 41

$5,995,000

55 Parkwood Drive, Milton, MA 02186

Milton, MA 02186

Investor Analysis

Beds

Baths

8.5

SqFt

9,320

Style

Single Family

Built

1915

Experience the pinnacle of Milton living at this 1915 French Colonial masterpiece. Set on nearly three acres at the foot of the Blue Hills Reservation, this legacy estate offers a rare blend of privacy and prestige. The grounds are an entertainer’s dream, featuring an in-ground pool, pool house, and a two-story, five-bay garage with an attached vintage greenhouse. Spanning 9,000+ sq. ft., the residence boasts seven bedrooms, ten bathrooms, and nine fireplaces. The main level offers grand formal spaces, including a mahogany-paneled library and a sophisticated office. The chef’s culinary suite is a masterwork of marble and high-end gas ranges. Retreat to the palatial primary wing—a four-room haven with dual baths and expansive views. The finished lower level adds versatility with twin fitness studios and a private lounge and office. Located eight miles from Boston and Logan, enjoy a country-manor lifestyle near world-class Milton Academy. A rare architectural gem. Welcome home!

Market Value Analysis

This Property

Size (SqFt) →Price →

This Property$643/sqft

Local Avg (Milton)$523/sqft

23% AboveMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Milton, MA.

Financials

Original Price$5,995,000

Annual Taxes$38,228

Parking

Garage6

Off-Street21

Interior Specifications

Total Rooms12

Fireplaces9

FlooringWood, Tile, Carpet, Marble, Stone / Slate, Flooring - Hardwood, Flooring - Stone/Ceramic Tile

BasementFull, Finished, Walk-Out Access, Garage Access

Climate & Utilities

HeatingBaseboard, Natural Gas, Fireplace(s), Fireplace

CoolingCentral Air, 3 or More

WaterPublic

SewerPublic Sewer

Building & Exterior

ConstructionFrame

RoofShingle

FoundationGranite

ZoningRA

Property & Lot

Acres2.77

SqFt Lot120,661

Lot FeaturesCleared, Gentle Sloping

Amenities & Appliances

Gas Water Heater • Range • Oven • Dishwasher • Disposal • Trash Compactor • Microwave • Indoor Grill • Refrigerator • Washer • Dryer • Range Hood

Neighborhood

Pool • Medical Facility • Bike Path • Conservation Area • Highway Access • House of Worship

Geography

Floorplan Breakdown

Structural Layout

Third

Bedroom 3Bedroom 4Bedroom 5Bathroom 3

Second

Primary BedroomBedroom 2Bathroom 1Bathroom 2

First

Office

Main,First

Living RoomDining RoomKitchenFamily Room

Living Room

Lvl Main,First

17 x 15

Flooring - Hardwood, French Doors, Exterior Access, Recessed Lighting

Dining Room

Lvl Main,First

20 x 17

Flooring - Hardwood, French Doors, Recessed Lighting

Kitchen

Lvl Main,First

38 x 22

Bathroom - Half, Flooring - Stone/Ceramic Tile, Dining Area, Countertops - Stone/Granite/Solid, Deck - Exterior, Recessed Lighting, Stainless Steel Appliances

Office

Lvl First

15 x 15

Fireplace, Flooring - Hardwood, Recessed Lighting

Family Room

Lvl Main,First

23 x 20

Flooring - Stone/Ceramic Tile, Cable Hookup, Recessed Lighting

Primary Bedroom

Lvl Second

20 x 16

Bathroom - Full, Flooring - Hardwood, Deck - Exterior, Recessed Lighting

Bedroom 2

Lvl Second

18 x 15

Bedroom 3

Lvl Third

13 x 10

Closet, Flooring - Wall to Wall Carpet, Recessed Lighting

Bedroom 4

Lvl Third

23 x 17

Closet, Flooring - Hardwood

Bedroom 5

Lvl Third

20 x 15

Fireplace, Closet, Flooring - Hardwood

Bathroom 1

Lvl Second

Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Jacuzzi / Whirlpool Soaking Tub

Bathroom 2

Lvl Second

Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Jacuzzi / Whirlpool Soaking Tub

Bathroom 3

Lvl Third

Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Jacuzzi / Whirlpool Soaking Tub, Recessed Lighting

Property History

Listed

$5,995,000

May 15, 2026

MLS® 73519804

Terminated

$5,995,000

Nov 29, 2025

MLS® 73397591

Listed

$5,995,000

Jun 27, 2025

MLS® 73397591

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

1,524 housing units permitted in the last 12 months (+52% vs the prior 12 months) — 1,030 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '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 9,320 sq ft principal dwelling). Lot size: 120,661 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: Kevin G. Keating

Listing Office: Keating Brokerage

MLS® Number: 73519804