Google street view image for 29 Cutler St Unit R, Winthrop, MA 02152

Off market

$442,737

•

1 ba

•

925

sq ft

29 Cutler St Unit R, Winthrop, MA 02152

About this home

29 Cutler St Unit R is a 925 square foot house on a 4,356 square foot lot with 2 bedrooms and 1 bathroom. Based on Redfin's Winthrop data, we estimate the home's value is $442,737.

Single-familyProperty Type

1880Year Built

4,356 sq ftLot Size

$479Est. Price/Sq.Ft.

4 spacesParking

Source:Public Records

Redfin Estimate

$442,737

$5,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 23.2% lower than the average sale price ($577K) of 6 comparable homes.

SOLD JUN 24, 2026
$600,000
A
3 beds1 bath1,310 sq ft
16 Wave Ave, Revere, MA 02151
SOLD APR 23, 2026
$450,000
B
1 bed1 bath620 sq ft
86 Undine Ave, Winthrop, MA 02152
SOLD JUL 2, 2026
$670,000
C
3 beds1.5 baths1,251 sq ft
91 Marshall St, Winthrop, MA 02152
SOLD MAY 18, 2026
$500,000
D
2 beds1 bath1,100 sq ft
5 Bates St, Revere, MA 02151
SOLD JAN 20, 2026
$570,000
E
3 beds1 bath1,182 sq ft
87 Hermon St, Winthrop, MA 02152
SOLD NOV 12, 2025
$670,000
F
2 beds1 bath961 sq ft
25 Faun Bar Ave, Winthrop, MA 02152

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Earn from this home

Sell

$419,795

Est. take-home

List your home with Redfin and save $2,214

Rent

$2,650/mo

Redfin rental estimate

List your home for rent

Market trends in 02152, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

99.0%

0.9% MoM

Median sale price

$715K

$86K MoM

Avg. days on market

27d

4 days MoM

Recently sold homes

3 MoM

New listings for sale

COMING SOON
$1,995,000
5 beds3.5 baths3,686 sq ft
119 Washington Ave, Winthrop, MA 02152
$519,000
3 beds2 baths1,256 sq ft
173-175 Shirley St #6, Winthrop, MA 02152
3D WALKTHROUGH
$839,000
4 beds3 baths2,204 sq ft
23 Sagamore, Winthrop, MA 02152
$979,000
4 beds2.5 baths2,666 sq ft
316 Bowdoin St, Winthrop, MA 02152
$989,000
3 beds3.5 baths2,180 sq ft
44 Bowdoin St, Winthrop, MA 02152
$339,999
2 beds1 bath772 sq ft
800 Governors Dr #6, Winthrop, MA 02152
$425,000
2 beds1 bath861 sq ft
29 Seafoam Ave #1, Winthrop, MA 02152
$498,500
2 beds1.5 baths1,002 sq ft
1020 Shirley St #1020, Winthrop, MA 02152
$519,000
3 beds1 bath1,374 sq ft
23 Trident #1, Winthrop, MA 02152
See all

Provided by Redfin

Sale history for 29 Cutler St Unit R

As the MLS and public records start to fill up, we'll list the details here.

Year

Property tax

Land + Additions

Assessment*

2023

$2,956

$234,300 + $42,000

$276,300

2022

$2,955 (+0.6%)

$209,300 + $42,000

$251,300

2021

$2,938 (+0.5%)

$186,800 + $44,900

$231,700

2020

$2,924 (+3.9%)

$186,800 + $44,900

$231,700

2019

$2,814 (+7.2%)

$172,200 + $41,300

$213,500

2018

$2,625 (+9.6%)

$147,800 + $37,600

$185,400

2017

$2,396 (+6.0%)

$130,900 + $35,400

$166,300

2016

$2,261 (−23.3%)

$113,800 + $33,300

$147,100

2014

$2,946 (+4.5%)

$128,500 + $60,600

$189,100

2013

$2,819 (+2.9%)

$128,500 + $60,600

$189,100

2012

$2,740 (+3.8%)

$128,500 + $60,600

$189,100

2011

$2,640 (+3.2%)

$128,500 + $62,800

$191,300

2010

$2,559 (+1.9%)

$138,700 + $62,800

$201,500

2009

$2,511

$165,500 + $86,400

$251,900

Tax history for 29 Cutler St Unit R

Year

Property tax

Land + Additions

Assessment*

2023

$2,956

$234,300 + $42,000

$276,300

2022

$2,955 (+0.6%)

$209,300 + $42,000

$251,300

2021

$2,938 (+0.5%)

$186,800 + $44,900

$231,700

2020

$2,924 (+3.9%)

$186,800 + $44,900

$231,700

2019

$2,814 (+7.2%)

$172,200 + $41,300

$213,500

2018

$2,625 (+9.6%)

$147,800 + $37,600

$185,400

2017

$2,396 (+6.0%)

$130,900 + $35,400

$166,300

2016

$2,261 (−23.3%)

$113,800 + $33,300

$147,100

2014

$2,946 (+4.5%)

$128,500 + $60,600

$189,100

2013

$2,819 (+2.9%)

$128,500 + $60,600

$189,100

2012

$2,740 (+3.8%)

$128,500 + $60,600

$189,100

2011

$2,640 (+3.2%)

$128,500 + $62,800

$191,300

2010

$2,559 (+1.9%)

$138,700 + $62,800

$201,500

2009

$2,511

$165,500 + $86,400

$251,900

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

Property details

Interior

Bathroom Information
# of Full Baths: 1

Heating & Cooling
Heating Type: Forced Hot Water

Room Information
# of Rooms: 5

Exterior

Exterior Information
Physical Condition: Fair
Building Style Type: Cottage/Bungalow
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Hip

Property Information
Living Sq. Ft: 925
Gross Sq. Ft: 973
# of Units: 1
# of Stories: 1

Lot Information
# of Buildings: 1
Land Sq. Ft: 4,356
Municipality Name: WINTHROP
Acres: 0.1
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 2
Baths: 1.0
Sq. Ft.: 925
Stories: 1.0
Lot Size: 4,356 square feet
Style: Single Family Residential
Year Built: 1880
Year Renovated: —
County: Suffolk County
APN: 1422868

Home facts updated by county records on Jul 31, 2025

Around this home

Schools

Arthur T. Cummings Elementary School

Public 3-5 • Assigned • 0.7mi

5/10

Winthrop Middle School

Public 6-8 • Assigned • 0.6mi

8/10

Winthrop Senior High School

Public 9-12 • Assigned • 0.6mi

5/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

10/10 Flood Factor

Estimated 80%+ chance of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 96° expected this year, 15 days in 30 years

6/10 Wind Factor

77% 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

Winthrop, MA • 02152

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 9.2 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9.2 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$421,000 – $510,000

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Nearby similar homes

NEW 13 HRS AGO

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New listings for sale in 02152

COMING SOON

$1,995,000

5 beds3.5 baths3,686 sq ft

119 Washington Ave, Winthrop, MA 02152

$519,000

3 beds2 baths1,256 sq ft

173-175 Shirley St #6, Winthrop, MA 02152

3D WALKTHROUGH

$839,000

4 beds3 baths2,204 sq ft

23 Sagamore, Winthrop, MA 02152

$979,000

4 beds2.5 baths2,666 sq ft

316 Bowdoin St, Winthrop, MA 02152

$989,000

3 beds3.5 baths2,180 sq ft

44 Bowdoin St, Winthrop, MA 02152

$339,999

2 beds1 bath772 sq ft

800 Governors Dr #6, Winthrop, MA 02152

$425,000

2 beds1 bath861 sq ft

29 Seafoam Ave #1, Winthrop, MA 02152

$498,500

2 beds1.5 baths1,002 sq ft

1020 Shirley St #1020, Winthrop, MA 02152

$519,000

3 beds1 bath1,374 sq ft

23 Trident #1, Winthrop, MA 02152

Home values near 29 Cutler St Unit R

Data from public records.

Address	Redfin Estimate
26 Cutler St, Winthrop, MA 4 Beds \| 2.5 Baths \| 1832 Sq. Ft.	$909,863
41 Cutler St Apt 1, Winthrop, MA 1 Beds \| 1 Baths \| 672 Sq. Ft.	$327,601

Address	Redfin Estimate
30 Cutler St, Winthrop, MA 6 Beds \| 3 Baths \| 2423 Sq. Ft.	$1,005,457
41 Cutler St Apt 2, Winthrop, MA 2 Beds \| 1 Baths \| 658 Sq. Ft.	$349,005

Address	Redfin Estimate
40 Cutler St, Winthrop, MA 5 Beds \| 2 Baths \| 1660 Sq. Ft.	$733,777
41 Cutler St Apt 3, Winthrop, MA 1 Beds \| 1 Baths \| 672 Sq. Ft.	$336,516

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