Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 2 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 3 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 4 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 5 of 41

+36 more

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 6 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 7 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 8 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 9 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 10 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 11 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 12 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 13 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 14 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 15 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 16 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 17 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 18 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 19 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 20 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 21 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 22 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 23 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 24 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 25 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 26 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 27 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 28 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 29 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 30 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 31 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 32 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 33 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 34 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 35 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 36 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 37 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 38 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 39 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 40 of 41

Single Family Residence at 22 Windsor Rd, Milton MA 02186, Milton, photo 41 of 41

41 photos

$1,795,000

22 Windsor Rd, Milton MA 02186

Milton, MA 02186

Listed by Colleen Foulsham

Bedrooms

Bathrooms

3.5

Living area

4,013 sqft

Year built

1929

About this home

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.

Highlights

Fireplace

Property details

MLS #: 73573740
Property type: Single Family Residence
Subdivision: Columbine Neighborhood
Status: Active
Days on market: 15
On market date: September 9, 2026
Stories: N/A
Total bathrooms: 3.5
Garage spaces: 2
Parking spaces: 6
Lot size: 0.19 acres

Location

Get directions →

Loading map…

Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary

Tucker

0.44 mi away · Grades -1-5

Nearest school -- attendance-zone data not available here

4.0

Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating

Enrollment: 464
Student:teacher ratio: 15.0:1
District: Milton

Middle

Charles S Pierce Middle

0.27 mi away · Grades 6-8

Nearest school -- attendance-zone data not available here

4.0

Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating

Enrollment: 928
Student:teacher ratio: 12.1:1
District: Milton

High

Milton High

0.68 mi away · Grades 9-12

Nearest school -- attendance-zone data not available here

4.0

Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating

Enrollment: 1,106
Student:teacher ratio: 13.8:1
District: Milton

Walkability

Blended score for Milton's center: EPA's National Walkability Index (street network, transit, land-use mix) combined with nearby-amenity density. EPA National Walkability Index only -- nearby-amenity data not cached yet for this area.

Walkable

out of 100

EPA National Walkability Index

12.3 / 20 -- Above average walkable

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

Home price

Down payment

Interest rate

Loan term

Adjust tax / insurance estimates

Property tax

% / yr

Home insurance

/mo

Est. monthly payment

$10,960/mo

$359,000 down

$1,436,000 loan

Principal & interest$9,314

Property tax (est.)$1,496

Home insurance (est.)$150

Similar homes you might like

New

$1,895,000

901 Randolph Ave, Milton MA 02186

Listed by Beth Rooney

$2,149,000

1375 Brush Hill Rd, Milton MA 02186

Milton, 02186

4 bd·3.5 ba·3,804 sqft

15 days on market

Listed by Foster/ Harrington Team

$1,899,000

901 Randolph Ave, Milton MA 02186

Listed by Kimberly Ruiz

$1,595,000

1262 Randolph Ave, Milton MA 02186

Milton, 02186

4 bd·4 ba·3,288 sqft

16 days on market

Listed by Danny Zheng

$1,895,000

375 Atherton Street, Milton MA 02186

Milton, 02186

4 bd·4.5 ba·4,398 sqft

98 days on market

Listed by David Green

$1,500,000

17 Duggan Ln, Milton MA 02186

Milton, 02186

4 bd·1.5 ba·2,960 sqft

100 days on market

$1,495,000

45 Foster Lane, Milton MA 02186

Milton, 02186

4 bd·3.5 ba·2,575 sqft

108 days on market

Pool

Listed by Scott Farrell & Partners

$1,650,000

52 Ridgewood Rd, Milton MA 02186

Milton, 02186

6 bd·4.5 ba·5,077 sqft

113 days on market

Listed by Rebecca Huang

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 12 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.