22 Windsor Road

Milton MA 02186

4013 sq. ft.

8407 sq. ft.

Single-Family

Last sold for $2,015,000

Colleen Foulsham, last sold this property on 23 October 2026 after 43 days on market.

Overview

Located in Milton’s desirable Columbine neighborhood, this fully renovated four-bedroom Dutch Colonial offers exceptional design and incredible indoor-outdoor living. The magazine-worthy interior features a classic New England-style kitchen with soapstone countertops and Wolf and Sub-Zero appliances. A spacious breakfast nook with French doors to the backyard and formal dining room with patio access create an ideal setting for entertaining. The home offers two full and three half baths, plus finished attic and lower-level spaces. The showstopping garage doubles as an inviting lounge with a gas fireplace, wet bar and half bath while retaining its garage functionality. Complete with central air, gas heat and a backyard designed for gathering. Close to Kelly Field, Turner’s Pond, Glover School and Milton Academy, and minutes to the Trolley Line for convenient access to Boston. This is the one-of-a-kind Milton dream home you’ve been waiting for—completely finished and truly move-in ready.

Features

4 bedrooms

5 bathrooms

6 carspaces

4 open car spaces

2 garage spaces

4013 sq. ft. floor area

8407 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Milton over the last 12 months, the estimated median property value of 22 Windsor Road is $1.22m.

Median value

$1.22m

Estimated value range

$715k - $2.9m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Milton. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 22 Windsor Road

2026

Sold

$2,015,000

23 Oct 2026 by Colleen Foulsham, of FC Realty Group

2004

Sold

$559,000

28 May 2004 by Matthew Freeman, of Kelley & Rege Properties, Inc.

Happy sellers in Milton

We have insufficient information to provide an overview of customer satisfaction for Milton. Viewing the agent profiles, reviews and sales for Milton can provide insights for this location.