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

OFF MARKET

$429,564

•

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 $429,564.

Single-familyProperty Type

1880Year Built

4,356 sq ftLot Size

$464Est. Price/Sq.Ft.

4 spacesParking

Source:Public Records

Redfin Estimate

$429,564

$3,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 25.5% 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 JAN 20, 2026
$570,000
D
3 beds1 bath1,182 sq ft
87 Hermon St, Winthrop, MA 02152
SOLD MAY 18, 2026
$500,000
E
2 beds1 bath1,100 sq ft
5 Bates St, Revere, MA 02151
SOLD NOV 12, 2025
$670,000
F
2 beds1 bath961 sq ft
25 Faun Bar Ave, Winthrop, MA 02152

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$407,275

Est. take-home

List your home with Redfin and save $2,148

Rent

$2,545/mo

Redfin rental estimate

List your home for rent

Market trends in 02152, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.2%

+0.5% MoM

Median sale price

$620K

$21K MoM

Avg. days on market

38d

7 days MoM

Recently sold homes

9 MoM

New listings for sale

NEW 16 HRS AGO
$650,000
3 beds1 bath931 sq ft
33 Bay View Ave, Winthrop, MA 02152
$539,000
1 bed1 bath1,368 sq ft
60 Hermon St #3, Winthrop, MA 02152
$649,000
3 beds1.5 baths1,200 sq ft
84 Tafts Ave, Winthrop, MA 02152
$739,000
3 beds2 baths1,428 sq ft
8 Siren St, Winthrop, MA 02152
$710,000
4 beds2 baths1,193 sq ft
542 Shirley St, Winthrop, MA 02152
$419,900
1 bed1 bath525 sq ft
22 Pauline St #5, Winthrop, MA 02152
$399,900
1 bed1 bath500 sq ft
22 Pauline St #3, Winthrop, MA 02152
$865,000
2 beds2.5 baths1,806 sq ft
1001 Shirley St #2, Winthrop, MA 02152
$998,900
6 beds2.5 baths3,263 sq ft
217 Pleasant St, Winthrop, MA 02152
$479,900
2 beds1 bath1,056 sq ft
2 Edgar Ter #3, 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

$409,000 – $494,000

Reach more buyers when you sell with Redfin. Save up to $4,296 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

NEW 16 HRS AGO

$650,000

3 beds1 bath931 sq ft

33 Bay View Ave, Winthrop, MA 02152

$660,000

3 beds2.5 baths1,777 sq ft

3 London Ct, East Boston, MA 02128

$650,000

3 beds2 baths800 sq ft

496 Winthrop St, Winthrop, MA 02152

$698,000

2 beds1.5 baths1,522 sq ft

2 Porter Ave, Revere, MA 02151

NEW CONSTRUCTION

$1,425,000

4 beds4 baths3,000 sq ft

11 Billow Ave #11, Revere, MA 02151

$669,999

3 beds1 bath1,250 sq ft

51 Undine Ave, Winthrop, MA 02152

New listings for sale in 02152

NEW 16 HRS AGO

$650,000

3 beds1 bath931 sq ft

33 Bay View Ave, Winthrop, MA 02152

$539,000

1 bed1 bath1,368 sq ft

60 Hermon St #3, Winthrop, MA 02152

$649,000

3 beds1.5 baths1,200 sq ft

84 Tafts Ave, Winthrop, MA 02152

$739,000

3 beds2 baths1,428 sq ft

8 Siren St, Winthrop, MA 02152

$710,000

4 beds2 baths1,193 sq ft

542 Shirley St, Winthrop, MA 02152

$419,900

1 bed1 bath525 sq ft

22 Pauline St #5, Winthrop, MA 02152

$399,900

1 bed1 bath500 sq ft

22 Pauline St #3, Winthrop, MA 02152

$865,000

2 beds2.5 baths1,806 sq ft

1001 Shirley St #2, Winthrop, MA 02152

$998,900

6 beds2.5 baths3,263 sq ft

217 Pleasant St, 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.	$902,033
41 Cutler St Apt 1, Winthrop, MA 1 Beds \| 1 Baths \| 672 Sq. Ft.	$337,044

Address	Redfin Estimate
30 Cutler St, Winthrop, MA 6 Beds \| 3 Baths \| 2423 Sq. Ft.	$1,016,409
41 Cutler St Apt 2, Winthrop, MA 2 Beds \| 1 Baths \| 658 Sq. Ft.	$357,801

Address	Redfin Estimate
40 Cutler St, Winthrop, MA 5 Beds \| 2 Baths \| 1660 Sq. Ft.	$721,328
41 Cutler St Apt 3, Winthrop, MA 1 Beds \| 1 Baths \| 672 Sq. Ft.	$378,639

More real estate resources

Cities
Zip Codes
Neighborhoods
Minor Civil Divisions
Popular Searches

Boston homes for sale
Newton homes for sale
Winthrop Town homes for sale

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Winthrop	Agents near me	Quincy, MA homes for sale	Winthrop Housing Market
Houses for sale near me	Boston, MA homes for sale	Brookline, MA homes for sale
Land for sale near me	Newton, MA homes for sale	Arlington, MA homes for sale
Open Houses near me	Cambridge, MA homes for sale	Winthrop Property Records
Condos for sale near me	Lexington, MA homes for sale	MA New Listings

02128 homes for sale
02151 homes for sale
02152 homes for sale