OFF MARKET

Off Market Oct 2015 for $900K

$1,705,738

Est. refi paymentEst. refi $2,731/mo

•

2,353

sq ft

44 Windsor Rd, Milton, MA 02186

About this home

Have you been looking and looking? You just hit the jackpot! This pristine brick and slate roof home, in the sought-after Columbine-Cliff neighborhood, is hitting the market! It features high ceilings and well-proportioned rooms that flow seamlessly for comfortable family living. Enjoy both formal and casual entertaining either indoors, or on an oversized outdoor patio, surrounded by beautifully landscaped gardens. You will appreciate how meticulously the home has been cared for, including thoughtful renovations that add to its dynamic flow. This home is located just a short walk from popular locales such as The Plate, Steel & Rye, and 88 Wharf. Other walkable conveniences include public transportation, prestigious Milton Public and private schools, tennis courts, and library. It is in close proximity to The Blue Hills Reservation, a popular urban escape featuring hiking, biking, skiing, and swimming and it is just 8 miles out of downtown Boston. Welcome to Milton and to 44 Windsor Rd.

Single-familyProperty Type

1929Year Built

9,464 sq ftLot Size

$725Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Marta Rodriguez Gamboa • Coldwell Banker Residential Brokerage - Milton - Adams St.

Bought with Marta Rodriguez Gamboa • Coldwell Banker Residential Brokerage - Milton - Adams St.

Redfin checked: a few seconds ago

•Source:MLS PIN #71887898

Redfin Estimate

$1,705,738

$806K since sold in October 2015$3,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 27% higher than the average sale price ($1.34M) of 6 comparable homes.

SOLD MAY 28, 2026
$834,000
A
5 beds2.5 baths2,000 sq ft
27 Ellison Ave, Mattapan, MA 02126
SOLD JUL 24, 2026
$1,280,000
B
4 beds1.5 baths2,486 sq ft
3 Windsor Rd, Milton, MA 02186
SOLD JUN 2, 2026
$1,170,000
C
4 beds2 baths1,969 sq ft
434 Brook Rd, Milton, MA 02186
SOLD MAY 1, 2026
$1,570,000
D
4 beds2.5 baths2,544 sq ft
30 Ridge Rd, Milton, MA 02186
SOLD JUL 30, 2026
$1,635,000
E
3 beds2.5 baths2,339 sq ft
60 Marilyn Rd, Milton, MA 02186
SOLD APR 28, 2026
$1,570,000
F
4 beds2.5 baths2,782 sq ft
44 Allen Cir, Milton, MA 02186

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Earn from this home

Sell

$1,071,202

Est. take-home

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Refinance

Est. cash available

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Rent

$5,671/mo

Redfin rental estimate

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Market trends in 02186, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

104.6%

0.5% MoM

Median sale price

$1.0M

$40K MoM

Avg. days on market

20d

0 days MoM

Recently sold homes

17 MoM

New listings for sale

OPEN FRI, 11:30AM TO 12:30PM
$1,050,000
3 beds2.5 baths1,946 sq ft
61 Elm St, Milton, MA 02186
OPEN FRI, 5:30PM TO 7PM
$1,100,000
3 beds2.5 baths2,000 sq ft
785 Brook Rd, Milton, MA 02186
OPEN SAT, 12PM TO 1:30PM
$950,000
4 beds2.5 baths1,641 sq ft
45 Adanac Rd, Milton, MA 02186
OPEN TODAY, 4:30PM TO 6PM
$699,000
3 beds1.5 baths1,350 sq ft
66 Ferncroft Rd, Milton, MA 02186
OPEN FRI, 11AM TO 12:30PM
$1,225,000
3 beds3 baths3,182 sq ft
355 Brush Hill Rd, Milton, MA 02186
$1,099,000
4 beds1.5 baths2,100 sq ft
45 Wendell Park, Milton, MA 02186
OPEN SUN, 1PM TO 2:30PM
$839,000
3 beds1.5 baths1,248 sq ft
37 Nahanton Ave, Milton, MA 02186
See all

Provided by Redfin

Sale history for 44 Windsor Rd

Date

Event

Price

MLS PIN #71887898

Oct 7, 2015

Sold

$900,000

$382/sq ft

Aug 18, 2015

Pending

—

Aug 11, 2015

Listed

$889,000

$378/sq ft

MLS PIN #70317495

May 19, 2006

Sold

$725,000

$308/sq ft

Mar 28, 2006

Listing Removed

—

Jan 19, 2006

Listed

$749,000

$318/sq ft

1920’s charm with soaring ceilings, hardwood floors, & 3 true floors of living space. Impressive master suite, master bath and private deck area. Generous bedroom space spread over 2 floors. Custom painting, fabric wallpaper, slate roofing and steel frame construction. Bonus 2 car garage all set on prof. landscaped lot w/oversized brick patio. Dressed to the nines and ready for entertaining, this handsome brick colonial is located in most desirable Columbine neighborhood.

Public Records

May 25, 1993

Sold

$250,000

$106/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$12,775 (+3.9%)

$514,800 + $605,800

$1,120,600

2022

$12,294 (+3.6%)

$514,800 + $471,100

$985,900

2021

$11,872 (+1.4%)

$455,500 + $448,700

$904,200

2020

$11,704 (+2.5%)

$451,100 + $441,000

$892,100

2019

$11,417 (+6.7%)

$438,000 + $428,200

$866,200

2018

$10,697 (+6.9%)

$355,500 + $419,100

$774,600

2017

$10,007 (+7.8%)

$338,600 + $399,400

$738,000

2016

$9,283 (+7.4%)

$296,300 + $391,300

$687,600

2015

$8,643 (−3.4%)

$254,000 + $366,000

$620,000

2014

$8,948 (+2.0%)

$254,000 + $342,900

$596,900

2013

$8,774 (+4.8%)

$254,000 + $342,900

$596,900

2012

$8,376 (+3.4%)

$254,000 + $329,700

$583,700

2011

$8,104 (+0.5%)

$254,000 + $322,000

$576,000

2010

$8,066 (+12.8%)

$282,200 + $322,000

$604,200

2009

$7,152

$282,200 + $327,000

$609,200

Tax history for 44 Windsor Rd

Year

Property tax

Land + Additions

Assessment*

2023

$12,775 (+3.9%)

$514,800 + $605,800

$1,120,600

2022

$12,294 (+3.6%)

$514,800 + $471,100

$985,900

2021

$11,872 (+1.4%)

$455,500 + $448,700

$904,200

2020

$11,704 (+2.5%)

$451,100 + $441,000

$892,100

2019

$11,417 (+6.7%)

$438,000 + $428,200

$866,200

2018

$10,697 (+6.9%)

$355,500 + $419,100

$774,600

2017

$10,007 (+7.8%)

$338,600 + $399,400

$738,000

2016

$9,283 (+7.4%)

$296,300 + $391,300

$687,600

2015

$8,643 (−3.4%)

$254,000 + $366,000

$620,000

2014

$8,948 (+2.0%)

$254,000 + $342,900

$596,900

2013

$8,774 (+4.8%)

$254,000 + $342,900

$596,900

2012

$8,376 (+3.4%)

$254,000 + $329,700

$583,700

2011

$8,104 (+0.5%)

$254,000 + $322,000

$576,000

2010

$8,066 (+12.8%)

$282,200 + $322,000

$604,200

2009

$7,152

$282,200 + $327,000

$609,200

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

9,583 Sq. Ft.

Year renovated

—

Sq. Ft.

2,610

Year built

1929

Style

Single Family Residential

County

Norfolk County

APN

129656

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 21, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 7
Parking Features: Detached, Garage Door Opener, Storage, Paved Drive, Off Street

Interior

Master Bedroom Information
Level: Second
Features: Walk-In Closet(s),Closet/Cabinets - Custom Built,Flooring - Hardwood,Balcony / Deck,Deck - Exterior

Bedroom #2 Information
Level: Second

Bedroom #3 Information
Level: Second

Bedroom #4 Information
Level: Third

Bedroom #5 Information
Level: Third

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Living Room Information
Level: First
Features: Flooring - Hardwood

Dining Room Information
Level: First
Features: Flooring - Hardwood

Kitchen Information
Level: First
Features: Ceiling Fan(s),Coffered Ceiling(s),Closet/Cabinets - Custom Built,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Kitchen Island,Cabinets - Upgraded,Recessed Lighting,Remodeled,Stainless Steel Appliances,Gas Stove

Basement Information
Basement: Full, Partially Finished

Laundry Information
Laundry Features: In Basement

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1
Fireplace Features: Living Room

Interior Features
# of Rooms (Total): 9
Window Features: Screens
Flooring: Wood, Tile, Stone / Slate
Interior Features: Den, Great Room, Wired for Sound

Exterior

Building Information
Building Area (Total): 2,353
Foundation Details: Stone, Granite
Construction Materials: Brick, See Remarks
Year Built Source: Public Records
Year Built Details: Approximate
Color: Brick

Exterior Features
Fencing: Fenced
Roof: Slate, Other
Patio And Porch Features: Deck, Patio
Exterior Features: Deck, Patio, Sprinkler System, Screens, Fenced Yard

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.22
Lot Features: Level
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $8,643
Tax Year: 2015

Utilities

Utility Information
Utilities: for Gas Range
Sewer: Public Sewer
Water Source: Public
Electric: 100 Amp Service

Heating & Cooling
Has Heating
Heating: Hot Water, Natural Gas

Location

Location Information
Directions: Hinckley Road to Windsor or Brook Road to Windsor
UnparsedAddress: 44 Windsor Road, Milton MA 02186

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Stable(s), Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, University

Public facts

Beds: 5
Baths: 3.5
Sq. Ft.: 2,610
Stories: 2.0
Lot Size: 9,583 square feet
Style: Single Family Residential
Year Built: 1929
Year Renovated: —
County: Norfolk County
APN: 129656

Home facts updated by county records on Jul 21, 2023

Other

Listing Information
Exclusions: Dining Room & Den Chandeliers And Living Room Sconces.
StandardStatus: Closed

Around this home

Schools

Tucker Elementary School

Public PreK-5 • Assigned • 0.5mi

6/10

Charles S Pierce Middle School

Public 6-8 • Assigned • 0.3mi

8/10

Milton High School

Public 9-12 • Assigned • 0.7mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.31% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 96° expected this year, 14 days in 30 years

6/10 Wind Factor

64% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Milton, MA • 02186

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.62M – $1.96M

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New listings for sale in 02186

OPEN FRI, 11:30AM TO 12:30PM

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61 Elm St, Milton, MA 02186

OPEN FRI, 5:30PM TO 7PM

$1,100,000

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785 Brook Rd, Milton, MA 02186

OPEN SAT, 12PM TO 1:30PM

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45 Adanac Rd, Milton, MA 02186

OPEN TODAY, 4:30PM TO 6PM

$699,000

3 beds1.5 baths1,350 sq ft

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OPEN FRI, 11AM TO 12:30PM

$1,225,000

3 beds3 baths3,182 sq ft

355 Brush Hill Rd, Milton, MA 02186

$1,099,000

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OPEN SUN, 1PM TO 2:30PM

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Home values near 44 Windsor Rd

Data from public records.

Address	Redfin Estimate
54 Windsor Rd, Milton, MA 6 Beds \| 3.5 Baths \| 4008 Sq. Ft.	$1,901,824
26 Windsor Rd, Milton, MA 4 Beds \| 1.5 Baths \| 2367 Sq. Ft.	$1,394,808

Address	Redfin Estimate
16 Windsor Rd, Milton, MA 4 Beds \| 1.5 Baths \| 1904 Sq. Ft.	$1,245,446
32 Windsor Rd, Milton, MA 4 Beds \| 1.5 Baths \| 2068 Sq. Ft.	$1,404,958

Address	Redfin Estimate
22 Windsor Rd, Milton, MA 4 Beds \| 2 Baths \| 2021 Sq. Ft.	$1,410,926
38 Windsor Rd, Milton, MA 4 Beds \| 1.5 Baths \| 2226 Sq. Ft.	$1,296,535

Property information provided by MLS PIN when last listed in 2015. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 02186, MA

Sale history for 44 Windsor Rd

Tax history for 44 Windsor Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02186

Home values near 44 Windsor Rd

More real estate resources