Location

Nearby schools

School ratings (A+ to F) from HJN community data.

St Mary of the Hills School
PK-8 · Regular
192 students · 9.1:1 student–teacher
0.1 mi
Charles S Pierce Middle School
6-8 · Regular · Milton School District
1,002 students · 11.6:1 student–teacher
Charles S Pierce Middle School school rating: B 0.3 mi
Tucker
PK-5 · Regular · Milton School District
454 students · 12.8:1 student–teacher
Tucker school rating: B- 0.5 mi
Glover
KG-5 · Regular · Milton School District
593 students · 14.3:1 student–teacher
Glover school rating: A 0.5 mi
Milton High School
9-12 · Regular · Milton School District
1,083 students · 12.4:1 student–teacher
Milton High School school rating: A+ 0.7 mi
Ellison / Parks Early Education School
EE-3 · Regular · Boston School District
190 students · 9.8:1 student–teacher
Ellison / Parks Early Education School school rating: D+ 0.8 mi
Kipp Academy Boston Charter School
KG-8 · Regular · Knowledge is Power Program Academy Boston Charter School
646 students · 13.6:1 student–teacher
Kipp Academy Boston Charter School school rating: C 0.9 mi
Mildred Avenue K-8 School
KG-8 · Regular · Boston School District
601 students · 10.6:1 student–teacher
Mildred Avenue K-8 School school rating: D+ 1.0 mi

Nearby places

Within 2 miles of this home: 17 restaurants and cafés, 4 grocery stores, 39 parks and green spaces, and 36+ transit stops.

Place data from OpenStreetMap.

Food & drink

Right Taste Jamaican Restaurant
River Street
0.6 mi
Burger King
Cummins Highway
0.7 mi
El Barrio Mexican Grill
Mexican restaurant · Central Avenue
0.8 mi
Coffee Break Cafe
Central Avenue
0.8 mi
Stevie's Milton
Central Avenue
0.8 mi
Steel & Rye
American restaurant · Eliot Street
0.8 mi
The Ice Creamsmith
1.1 mi
Madre Osteria Bar & Resturant
Italian restaurant · Wharf Street
1.1 mi

Groceries

America's Food Basket
Cummins Highway
0.7 mi
Star Market
River Street
1.1 mi
Price Rite
River Street
1.1 mi
Stop & Shop
American Legion Highway
1.8 mi

Parks & recreation

John L. Kelly Field
0.1 mi
Shields Park
0.3 mi
Turners Pond
0.4 mi
Turner's Pond
0.4 mi
Ryan Playground
0.6 mi
Neponset Esplanade Park
0.6 mi
Kennedy Playground
0.6 mi
Brush Hill Road Playground
0.7 mi

Transit

Brook Rd @ Windsor Rd
0.1 mi
Brook Rd opp Windsor Rd
0.1 mi
Brook Rd @ Standish Rd
0.1 mi
250 Brook Rd
0.2 mi
Opp 250 Brook Rd
0.2 mi
Brook Rd @ Lincoln St
0.2 mi
Brook Rd @ Brandon Rd
0.2 mi
Central Ave and Allerton
0.2 mi

Flock cameras and license-plate readers near 44 Windsor Road, Milton

This home
Flock Safety reader
Gunshot detector
Rings at ½ mile and 1 mile. Basemap © OpenMapTiles © OpenStreetMap contributors.
Open the Milton camera map

4 devices mapped within 1 mile of this home: 3 license-plate readers and 1 gunshot detector; 3 of them identified as Flock Safety devices. None within ½ mile. Nearest: 0.6 mi northwest.

Mapped devices by type and distance from this home
Device type	Within ½ mi	Within 1 mi
License-plate readers	0	3
of which Flock Safety	0	3
Gunshot detectors	0	1

Community-reported via OpenStreetMap; may be incomplete. Data as of Oct 24, 2026. © OpenStreetMap contributors (ODbL)

About these devices

License-plate readers (ALPR) are fixed cameras that photograph passing vehicles and read their plates. Records are typically shared with the agency or association that operates the camera.

Flock Safety is a company whose plate-reader cameras are used by police departments, cities, HOAs and businesses. Its devices are usually solar-powered and pole-mounted.

Gunshot detectors are acoustic sensors that listen for gunfire and report its estimated location.

The 02186 market

Homes for sale: 50
Median list price: $949,000

Similar homes nearby

See all in 02186

Sources for the nearby listings shown on this page

MLS Property Information Network (MLS PIN): The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-10-22 16:20:00 UTC

Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

No listing photos

44 Windsor Road, Milton MA 02186

5

Beds

3.5

Baths

2,610

Sqft

1929

Year built

Estimated value: $1,510,293

Range $1,459,768 – $1,560,818 · as of August 30, 2026

How this estimate has moved

ATTOM automated valuation model · 54 published estimates over 6.7 years · shaded band is the model's own published low-to-high range

$1,036,514 January 2020$1,510,293 August 2026

Highest reading $1,667,923 in November 2025; lowest $1,001,772 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.

Public records

5 beds
3.5 baths
2,610 sqft
9,466 sqft lot
Built 1929
Stories: 2
Use: RESIDENTIAL
APN MILT M:E B:056 L:8

Estimate your monthly payment

Home price

Down payment (20%)

$302,059

Loan term

Interest rate (%)

Property tax (%/yr)

Home insurance ($/yr)

HOA ($/mo)

Estimated monthly payment

$9,801/mo

Principal & interest$8,300

Property tax$1,384

Home insurance$117

Loan amount $1,208,234. Estimate only — your actual rate and payment depend on credit, location, and lender.

Tax history

2025 roll

Land: $567,500
Structure: $667,000
Assessed total: $1,234,500
County market value: $1,443,335
Property tax billed: $13,691

Sale & deed history

March 31, 2017Arm's-length$975,000
October 7, 2015Arm's-lengthCash$900,000
April 27, 2015Arm's-length—
May 19, 2006Arm's-length$725,000