249 Pleasant St Winthrop, MA 02152 / 2803

Map
(UPDATED: 09/23/2025)
Property Report

Information about property on 249 Pleasant St, Winthrop MA, 02152-2803. Find out owner contacts, building history, price, neighborhood at Homemetry Address Directory.

Units

Property details of units in this apartment building

#2

  • 743 sqft
  • 1 bed
  • 1 bath

#3

  • 743 sqft
  • 2 beds
  • 1 bath

#1

#E2

Property Details

This is a comfortable multi-family three home, which is situated at 249 Pleasant Street, Winthrop, MA.

Facts

  • Built in 1900
  • Lot size 5,694 sqft
  • Floor size 3,294 sqft
  • Bedrooms 5
  • Bathrooms 2,5
  • Stories 3 story
  • Style Other
  • Heating & Cooling
  • Heat type Hot Water
  • Exterior Home Features
  • Exterior material Wood
  • Exterior walls Wood Siding
  • Roof type Asphalt

Misc

  • Units 2

Householders and Tenants for 249 Pleasant St, Winthrop MA

Possible residents contact details

Person Name Phone Number Additional Info
C Tsiotos Age: 100
617-539-****
Christos Tsiotos Apt # 1
617-846-****
Constantine O Tsiotos Age: 100 Apt # 1
617-846-****
Residential status:
Homeowner
Email:
[email protected]
Constantine Tsitos Apt # 1
617-846-****
Constantion Tsiotos Age: 100 Apt # 1
617-680-****
Residential status:
Renter
Job:
Protective Service Occupations
Dawn M Osborne Age: 55 Apt # 2
617-846-****
Jane Elizabeth Moskowitz Apt # E2
John C Tsiotos Age: 61 Apt # 1
617-846-****
Residential status:
Homeowner
Job:
Protective Service Occupations
Mary J Osborne Apt # 2
617-846-****
Residential status:
Homeowner
N Tsiotos Age: 71 Apt # 1
617-539-****
Pauline C Tsiotos Age: 97 Apt # 1
617-539-****

Units - Who lives at 249 Pleasant St, Winthrop MA

#21 bed, 1 bath, 743 sqft02152-2803
#32 beds, 1 bath, 743 sqft02152-2803
#1N Tsiotos 02152-2803
#E2Jane Elizabeth Moskowitz 02152-2803

Cost estimate history

YearTaxAssessmentMarket
2013 $4,838 $324,500 N/A

Where is 249 Pleasant St, Winthrop MA located on map?

Market Activities

To date, we have no information about market activities in 2025
Jun 2023 Recent Rent
249 Pleasant St #2
Price history :
$1,700
  • Apartment
  • 743 sqft
  • 1 bed
  • 1 bath
Jun 2022 Recent Rent
249 Pleasant St #3
Price history :
$2,200
  • Apartment
  • 743 sqft
  • 2 beds
  • 1 bath

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Pleasant St Fire Incident History

To date, we have no information about fire incidents in 2025
31 Oct 2017 Fuel burner/boiler malfunction, fire confined
361 Pleasant St, Winthrop MA
Property Use —
1 or 2 family dwelling
01 Oct 2017 Building fires
450 Pleasant St, Winthrop MA
Property Use —
1 or 2 family dwelling
12 Jun 2017 Fire, other
550 Pleasant St, Winthrop MA
Property Use —
Multifamily dwellings
Area of Origin —
Machinery room or area; elevator machinery room
First Ignition —
Conveyor belt, drive belt, V-belt
Heat Source —
Heat from powered equipment, other
12 Nov 2016 Brush, or brush and grass mixture fire
163 Pleasant St, Winthrop MA
Property Use —
Graded and cared-for plots of land
Area of Origin —
Courtyard, patio, porch, terrace
First Ignition —
Organic materials, other

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249 Pleasant St incidents registered in FEMA
(Federal Emergency Management Agency)

To date, we have no information about incidents registered in FEMA in 2025
06 Aug 2003 EMS call, excluding vehicle accident with injury
249 Pleasant St, Winthrop MA
Property Use —
1 or 2 family dwelling
14 Feb 2002 EMS call, excluding vehicle accident with injury
249 Pleasant St, Winthrop MA
Property Use —
1 or 2 family dwelling
30 Oct 2001 EMS call, excluding vehicle accident with injury
249 Pleasant St, Winthrop MA
Property Use —
1 or 2 family dwelling

Pleasant St Incidents registered in FEMA
(Federal Emergency Management Agency)

To date, we have no information about incidents registered in FEMA in 2025
09 Dec 2015 Hazardous condition, other
316 Pleasant St, Winthrop MA
Property Use —
Residential street, road or residential driveway
14 Nov 2015 Power line down
44 Pleasant St, Winthrop MA
Property Use —
1 or 2 family dwelling
02 Sep 2014 Gas leak (natural gas or LPG)
363 Pleasant St, Winthrop MA
Property Use —
1 or 2 family dwelling
14 Jul 2014 Electrical wiring/equipment problem, other
550 Pleasant St, Winthrop MA
Property Use —
Multifamily dwellings

View more

Properties Nearby

Street AddressResidens/Landlords
25 Pleasant St, Winthrop, MA 02152-2622
Single Family
  • 4 beds
  • 2.5 baths
  • 1,942 sqft
  • Built in 1900
 Jim Cahillane, S Cahillane
26 Pleasant St, Winthrop, MA 02152-2623
Single Family
  • 5 beds
  • 2 baths
  • 1,948 sqft
  • Built in 1900
 Danielle R Conley, Thomas M Conley
222 Pleasant St, Winthrop, MA 02152-2276
Single Family
  • 5 beds
  • 2 baths
  • 3,494 sqft
  • Built in 1900
 Daniel J Gillis, Deborah Gillis
230 Pleasant St, Winthrop, MA 02152-2277
Single Family
  • 5 beds
  • 2 baths
  • 2,148 sqft
  • Built in 1926
 Jeanette V Donovan, Lacey A Donovan
233 Pleasant St, Winthrop, MA 02152-2224
Multiple Occupancy
  • 4 beds
  • 2 baths
  • 3,002 sqft
  • Built in 1920
 Myriam Andrade, Elizabeth A Benson
239 Pleasant St, Winthrop, MA 02152-2224
Multiple Occupancy
  • 5 beds
  • 3 baths
  • Lot: 4,759 sqft
  • Built in 1920
 Catherine T Earl, Christina Earl
240 Pleasant St, Winthrop, MA 02152-2277
Single Family
  • 4 beds
  • 2.5 baths
  • 2,900 sqft
  • Built in 1894
 Kelly A Dougherty, Michael J Dougherty
254 Pleasant St, Winthrop, MA 02152-2840
Multiple Occupancy
  • 5 beds
  • 2 baths
  • Lot: 9,220 sqft
  • Built in 1850
 Tlp Transportation Corp, W Ancillo
255 Pleasant St, Winthrop, MA 02152-2803
Multiple Occupancy
  • 6 beds
  • 3 baths
  • Lot: 10,436 sqft
  • Built in 1900
 Geoff Ames, Barbara J Calla
260 Pleasant St, Winthrop, MA 02152-2840
Single Family
  • 3 beds
  • 2 baths
  • 2,176 sqft
  • Built in 1900
 Fran Dingle, Frances Dingle

Pleasant Street

Houses for Sale on Pleasant Street (4)

Recently Sold Homes on Pleasant Street (35)

Houses for Rent on Pleasant Street (2)

Winthrop, MA

Houses for Sale on Winthrop, MA (90)

Recently Sold Homes on Winthrop, MA (881)

Houses for Rent on Winthrop, MA (50)

 

FAQ about the house at 249 Pleasant St, Winthrop, MA


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