Winthrop, MA Homes

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  /41

  $719,900 Pending

  • 4 Beds
  • 1 Bath
  • 1,964 Sq Ft

  14 Pleasant Park Rd, Winthrop, MA 02152

  WELCOME HOME to 14 Pleasant Park Road...BEEN IN THE SAME FAMILY FOR OVER 17 YEARS!!!...This BEAUTIFUL 4 BEDROOMS/ 1 FULL BATH 'GAMBREL COLONIAL STYLE HOME' is ready for new owners...1st FLOOR offers WELCOMING FOYER w/Hardwood Floors, CHERRY KITCHEN CABINETS w/GRANITE COUNTERS & GRANITE ISLAND w/Tiled Flooring & Recess Lighting, DINING ROOM w/Hardwood Floors, LIVING ROOM w/Hardwood Floors...2nd

  Regina Paratore RE/MAX 360

  14 Pleasant Park Rd, Winthrop, MA 02152
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  /9

  $2,100 total monthly price

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Apartment for Rent

  45 Sturgis St Unit 1, Winthrop, MA 02152

  This is a one bedroom with ALL UTILITIES INCLUDED...tenant only pays for cable/wifi. It is mere steps to Winthrop beach and public transportation is at the corner of the street. There is an eat-in kitchen with new cabinets, stainless appliances and wood laminate flooring. The bedroom is average size with closet and wall-to-wall carpeting. The bathroom has a bathtub and shower. There will be snow

  James Polino Compass

  45 Sturgis St Unit 1, Winthrop, MA 02152
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  /32

  $850,000 Sold Jul 17, 2025

  81 Lowell Rd, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,998 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $425/SF
  • 12 Days On Market

  Current Estimated Value $836,485

  Last Listing Agent Randall Horn Entourage Realty LLC

  81 Lowell Rd, Winthrop, MA 02152
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  /32

  Est $522,837 Not Listed For Sale

  3 Seal Harbor Rd Unit 434, Winthrop, MA 02152

  • 1 Bed
  • 1 Bath
  • 840 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 434, Winthrop, MA 02152

  Last Sold Summary

  • 3% Above List Price
  • $607/SF
  • 43 Days On Market

  Last Sold Price $510,000

  Last Listing Agent Sharon Tallent Compass
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  /35

  $650,000

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  47 Highland Ave, Winthrop, MA 02152

  Wonderful opportunity to own a coastal Winthrop home with tremendous potential. A welcoming mudroom opens to a spacious foyer and a large living and dining area with great flow for everyday living. A bonus front room offers flexible space for a home office, playroom, or an expanded open-concept layout. The kitchen leads directly to the back deck for warm-weather entertaining. Upstairs features

  Elizabeth Ferrara Cottage Hill Real Estate

  47 Highland Ave, Winthrop, MA 02152
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  /10

  $3,200 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  436 Revere St, Winthrop, MA 02152

  Take in the view of the ocean from this single family home. The house has two bedrooms, two bathroom, livingroom and eat-in kitchen/ dinning area. Parking is availiable for two cars. Easy access to Boston from the Orient heights and Beachmont subway station and convenient MBTA buses. Avaliable for midterm Rental

  436 Revere St, Winthrop, MA 02152
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  /42

  $785,000 Sold May 16, 2025

  95 Summit Ave Unit 4, Winthrop, MA 02152

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1890

  Last Sold Summary

  • 7% Above List Price
  • $467/SF
  • 6 Days On Market

  Current Estimated Value $791,917

  Last Listing Agent Joseph Schutt Unit Realty Group, LLC

  95 Summit Ave Unit 4, Winthrop, MA 02152
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  /40

  Est $607,665 Not Listed For Sale

  3 Seal Harbor Rd Unit 232, Winthrop, MA 02152

  • 1 Bed
  • 2 Baths
  • 1,263 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 232, Winthrop, MA 02152

  Last Sold Summary

  • 7% Below List Price
  • $515/SF
  • 12 Days On Market

  Last Sold Price $650,000

  Last Listing Agent Nicole Bettano Lantern Residential
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  /20

  $383,000 Pending

  • 1 Bed
  • 1 Bath
  • 475 Sq Ft

  10 Somerset Ave Unit 403, Winthrop, MA 02152

  The Somerset – Winthrop Center’s Premier Boutique Condo Living by the Sea! This thoughtfully curated collection of 29 modern residences includes studio, 1BR, 1+, and 2BR layouts ,each designed with a clean, coastal aesthetic and high-quality finishes. Inside, open-concept floor plans, quartz countertops, stainless steel appliances, central A/C, and sleek modern design. Most homes include garage

  Charlesgate New Development Team Charlesgate Realty Group, llc

  10 Somerset Ave Unit 403, Winthrop, MA 02152
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  /9

  $2,295 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  100 Quincy Ave Unit 4, Winthrop, MA 02152

  Well maintained building in Winthrop's Upper Highlands. The other tenants in the building are long term tenants and the building has a full time maintenance person. This apartment has a very comfortable ambience with hardwood floors and good room sizes. The kitchen offers a dishwasher, microwave, refrigerator, disposal and very nice quality wood cabinets. The bath is tile and in good condition.

  James Polino Compass

  100 Quincy Ave Unit 4, Winthrop, MA 02152
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  $1,325,000 Sold Aug 15, 2025

  45 Highland Ave, Winthrop, MA 02152

  • 10 Beds
  • 4 Baths
  • 4,671 Sq Ft
  • Built 1900

  Last Sold Summary

  • 5% Below List Price
  • $284/SF
  • 35 Days On Market

  Current Estimated Value $1,348,350

  Last Listing Agent Jonathan Mathews Legacy Realty Advisors LLC

  45 Highland Ave, Winthrop, MA 02152
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  /28

  Est $542,539 Not Listed For Sale

  3 Seal Harbor Rd Unit 231, Winthrop, MA 02152

  • 1 Bed
  • 1.5 Baths
  • 1,033 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 231, Winthrop, MA 02152

  Last Sold Summary

  • 11% Above List Price
  • $474/SF
  • 45 Days On Market

  Last Sold Price $490,000

  Last Listing Agent Lisa Licata-Schepici L.L.S. Realty LLC
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  /15

  $360,000 Pending

  • 1 Bed
  • 1 Bath
  • 725 Sq Ft

  203 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  Oceanfront living just minutes from Boston! This bright first-floor one-bedroom condo sits directly across from Winthrop Beach in a classic seaside building with wraparound porches offering sweeping Atlantic views. With windows on three sides, the 725 sqft home is filled with natural light all day. The living room features hardwood floors and recessed lighting, while the kitchen with white

  Molly Walker Coldwell Banker Realty - Scituate

  203 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
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  /23

  $3,200 total monthly price

  • 2 Beds
  • 1 Bath
  • 958 Sq Ft
  • Condo for Rent

  9 Wilshire St Unit 1, Winthrop, MA 02152

  Welcome to this 2 Bedroom apartment in Winthrop by the Sea. Available May 1stUtilities included : Heat, hot water & electricity! Parking available! Perfect for traveling nurses, Airline workers, digital nomads & traveling professionalsEat in kitchen, laundry & off street parking. 15 Minute walk to the beach, 9 minute drive to Logan Airport, 21 Minute Drive to

  9 Wilshire St Unit 1, Winthrop, MA 02152
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  $777,000 Sold Nov 26, 2025

  32 Hale Ave, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft
  • Built 1920

  Last Sold Summary

  • 11% Below List Price
  • $548/SF
  • 144 Days On Market

  Current Estimated Value $769,845

  Last Listing Agent Sharon Tallent Compass

  32 Hale Ave, Winthrop, MA 02152
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  /42

  Est $981,550 Not Listed For Sale

  218 Cliff Ave, Winthrop, MA 02152

  • 4 Beds
  • 2.5 Baths
  • 2,343 Sq Ft
  • Built 1890

  218 Cliff Ave, Winthrop, MA 02152

  Last Sold Summary

  • 7% Above List Price
  • $393/SF
  • 17 Days On Market

  Last Sold Price $921,000

  Last Listing Agent Christine D'Ambrosio Lantern Residential
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  /21

  $650,000

  • 3 Beds
  • 2.5 Baths
  • 2,278 Sq Ft

  1080 Shirley St, Winthrop, MA 02152

  1080 Shirley St presents a rare two-family property with two separate structures, offering exceptional flexibility for owner-occupants or investors seeking strong rental potential. Ideally located just steps from the ocean in Winthrop, the property enjoys beautiful water views and a true coastal setting. The front unit features a spacious sunroom that fills the home with natural light, along with

  Reserve Team Reference Real Estate

  1080 Shirley St, Winthrop, MA 02152
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  /9

  $2,095 total monthly price

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • Apartment for Rent

  23 Siren St Unit 2, Winthrop, MA 02152

  Winthrop's Point Shirley. Not in the flood zone! Totally renovated apartment. Ocean views in this totally renovated 1 bedroom apartment. Newer kit and bath, newer appliances, flooring and more. There is a cozy deck to relax and enjoy your morning coffee while enjoying the sunshine, ocean views and the ocean breezes. Plenty of yard for your garden. Just move in and enjoy! Available May 1.

  James Polino Compass

  23 Siren St Unit 2, Winthrop, MA 02152
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  /22

  $719,000 Sold Dec 30, 2025

  92 Plummer Ave, Winthrop, MA 02152

  • 3 Beds
  • 1.5 Baths
  • 1,449 Sq Ft
  • Built 1937

  Last Sold Summary

  • $496/SF
  • 5 Days On Market

  Current Estimated Value $711,613

  Last Listing Agent Susan DeFelice Keller Williams Realty Boston-Metro | Back Bay

  92 Plummer Ave, Winthrop, MA 02152
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  /29

  Est $508,040 Not Listed For Sale

  173 Grovers Ave Unit 2, Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1904

  173 Grovers Ave Unit 2, Winthrop, MA 02152

  Last Sold Summary

  • 4% Above List Price
  • $408/SF
  • 78 Days On Market

  Last Sold Price $490,000

  Last Listing Agent Steve Binder Binder Residential
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  /27

  $990,000 Pending

  • 6 Beds
  • 2 Baths
  • 2,212 Sq Ft

  50-52 Wilshire St, Winthrop, MA 02152

  Outstanding Winthrop investment opportunity offering strong income potential in a highly desirable coastal community. This newly renovated two-family property features two spacious units (2BR and 4BR), ideal for owner-occupants seeking rental income or investors looking to expand their portfolio. Both units provide modern living with off-street parking for four vehicles total. Conveniently

  Lou Markakis Lynnway Associates

  50-52 Wilshire St, Winthrop, MA 02152
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  /28

  $2,400 total monthly price

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  25 Pratt St Unit 1, Boston, MA 02134

  Rent:$2,400 / mo.Beds:1 BedBaths:1 BathLaundry:Laundry on SiteUnit Level:1Parking:For Rent, Outdoor, $200 / Month

  25 Pratt St Unit 1, Boston, MA 02134
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  /23

  $369,000 Sold Jul 18, 2025

  203 Winthrop Shore Dr Unit 6, Winthrop, MA 02152

  • 1 Bed
  • 1 Bath
  • 725 Sq Ft
  • Built 1900

  Last Sold Summary

  • 6% Above List Price
  • $509/SF
  • 21 Days On Market

  Current Estimated Value $360,179

  Last Listing Agent Charles Roderick eXp Realty

  203 Winthrop Shore Dr Unit 6, Winthrop, MA 02152
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  /42

  Est $980,821 Not Listed For Sale

  36 Floyd St, Winthrop, MA 02152

  • 4 Beds
  • 2.5 Baths
  • 2,211 Sq Ft
  • Built 1925

  36 Floyd St, Winthrop, MA 02152

  Last Sold Summary

  • 4% Below List Price
  • $464/SF
  • 4 Days On Market

  Last Sold Price $1,025,000

  Last Listing Agent The Reference Group Reference Real Estate
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  /10

  $408,450 Pending

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft

  10 Somerset Ave Unit 404, Winthrop, MA 02152

  Welcome to Unit 404 at The Somerset—a premier boutique condo community in the heart of Winthrop. This thoughtfully designed studio features an open-concept kitchen and living area, perfect for entertaining or relaxing, along with a versatile bonus room with a sliding barn door for flexible use. Enjoy quartz countertops, stainless steel appliances, central A/C, and stylish finishes throughout. The

  Charlesgate New Development Team Charlesgate Realty Group, llc

  10 Somerset Ave Unit 404, Winthrop, MA 02152
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  /41

  $2,600 total monthly price

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • Apartment for Rent

  222 Winthrop Shore Dr Unit 7, Winthrop, MA 02152

  If you're looking for beach living this is a fantastic apartment for you! It is directly across the street from Winthrop Beach with 1 dedicated off-street parking spot. It is a bright, charming 2 bed/1 bath unit with new laminate flooring in the living area and wood parquet floors in each bedroom. The building has a laundry room which is just steps from this unit. You are 10 minutes from a blue

  James Polino Compass

  222 Winthrop Shore Dr Unit 7, Winthrop, MA 02152
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  /32

  $775,000 Sold Jan 30, 2026

  100 Cottage Ave, Winthrop, MA 02152

  • 3 Beds
  • 2.5 Baths
  • 2,293 Sq Ft
  • Built 1915

  Last Sold Summary

  • 12% Below List Price
  • $338/SF
  • 100 Days On Market

  Current Estimated Value $789,597

  Last Listing Agent Reserve Team Reference Real Estate

  100 Cottage Ave, Winthrop, MA 02152
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  /38

  Est $923,855 Not Listed For Sale

  89 Cliff Ave, Winthrop, MA 02152

  • 5 Beds
  • 2.5 Baths
  • 2,697 Sq Ft
  • Built 1900

  89 Cliff Ave, Winthrop, MA 02152

  Last Sold Summary

  • 12% Below List Price
  • $391/SF
  • 3 Days On Market

  Last Sold Price $1,055,000

  Last Listing Agent Erica Gore Century 21 Seaport
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  /20

  $400,000 Pending

  • 2 Beds
  • 1 Bath
  • 662 Sq Ft

  53 Trident Ave Unit 204, Winthrop, MA 02152

  Ideally situated just a few homes from the beach, this two-bedroom, pet-friendly condo offers the perfect opportunity to enjoy coastal living in Winthrop. Thoughtfully updated and well maintained, the home blends modern comforts with an unbeatable seaside location. This home features a refreshed kitchen with brand-new stainless steel appliances and a stylish tile backsplash. One of the bedrooms

  Domenico Barbuto DJB Realty Corporation

  53 Trident Ave Unit 204, Winthrop, MA 02152
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  /25

  $2,750 total monthly price

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Condo for Rent

  92 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  Bright & Modern 2-Bed & Studio in Winthrop – Available Now!Step into this beautifully updated 2-bedroom, 1-bathroom and Studio units in Winthrop, offering tons of natural light and stylish finishes throughout. With hardwood floors and an open layout, this apartment combines comfort and convenience in a prime location.Features you'll love:? Spacious bedrooms – Plenty of room to

  92 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
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  /30

  $950,000 Sold Nov 21, 2025

  40 Cottage Park Rd, Winthrop, MA 02152

  • 5 Beds
  • 3 Baths
  • 2,550 Sq Ft
  • Built 1900

  Last Sold Summary

  • $373/SF
  • 8 Days On Market

  Current Estimated Value $959,266

  Last Listing Agent The Reference Group Reference Real Estate

  40 Cottage Park Rd, Winthrop, MA 02152
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  /31

  Est $882,411 Not Listed For Sale

  92 Quincy Ave, Winthrop, MA 02152

  • 4 Beds
  • 2.5 Baths
  • 2,497 Sq Ft
  • Built 1910

  92 Quincy Ave, Winthrop, MA 02152

  Last Sold Summary

  • 4% Above List Price
  • $338/SF
  • 13 Days On Market

  Last Sold Price $845,000

  Last Listing Agent Leighann Eruzione Lantern Residential
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  $705,000 Open Sat 12:30PM - 1:30PM

  • 3 Beds
  • 1.5 Baths
  • 1,764 Sq Ft

  960 Shirley St, Winthrop, MA 02152

  Saturday open house cancelled due to weather! This well-maintained 3-bedroom, 2-bath home offers comfortable living in a prime Winthrop location. The freshly painted interior features large, well-proportioned rooms throughout. A fully finished lower level adds valuable living space, while the converted garage provides a unique bar and entertainment area. The private, fully fenced patio is perfect

  Bridget Conroy Coldwell Banker Realty - Milton

  960 Shirley St, Winthrop, MA 02152
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  /13

  $2,900 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,050 Sq Ft
  • Apartment for Rent

  585 Shirley St Unit 2, Winthrop, MA 02152

  2 Bed | 1 Bath| Waterfront – Winthrop HarborBeautifully renovated 2-bedroom, 1-bath ground-level apartment located directly on Winthrop Harbor. This open-concept unit features brand-new appliances, new hardwood flooring, and stunning ocean, harbor, and city views. Be the first to enjoy this updated waterfront home offering:• Heat and hot water included• Dishwasher• Private ground-level patio•

  Kevine Kakou Reference Real Estate

  585 Shirley St Unit 2, Winthrop, MA 02152
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  /39

  $538,000 Sold Oct 17, 2025

  12 Sewall Ave Unit 2, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 874 Sq Ft
  • Built 1925

  Last Sold Summary

  • $616/SF
  • 26 Days On Market

  Last Listing Agent Alex Walsh Access

  12 Sewall Ave Unit 2, Winthrop, MA 02152
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  /40

  Est $792,015 Not Listed For Sale

  53 Upland Rd, Winthrop, MA 02152

  • 3 Beds
  • 2.5 Baths
  • 1,516 Sq Ft
  • Built 1961

  53 Upland Rd, Winthrop, MA 02152

  Last Sold Summary

  • 1% Above List Price
  • $518/SF
  • 30 Days On Market

  Last Sold Price $785,000

  Last Listing Agent Louise Touchette Coldwell Banker Realty - Lynnfield
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  /10

  $399,000 Open Sat 10:30AM - 12:30PM

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft

  10 Somerset Ave Unit 304, Winthrop, MA 02152

  LAST STUDIO! Unit 304 at The Somerset—a premier boutique condo community in the heart of Winthrop. This thoughtfully designed studio features an open-concept kitchen and living area, perfect for entertaining or relaxing, along with a versatile bonus room with a sliding barn door for flexible use. Enjoy quartz countertops, stainless steel appliances, central A/C, and stylish finishes throughout.

  Charlesgate New Development Team Charlesgate Realty Group, llc

  10 Somerset Ave Unit 304, Winthrop, MA 02152
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  $2,500 - $3,200 total monthly price

  • 1 - 2 Beds
  • 2 Baths
  • 524 Sq Ft
  • Condo for Rent

  5 Fremont St, Winthrop, MA 02152

  5 Fremont St, Winthrop, MA 02152
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  /39

  $650,000 Sold Sep 30, 2025

  One Seal Harbor Rd Unit 604, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 1,124 Sq Ft
  • Built 1983

  Last Sold Summary

  • $578/SF
  • 8 Days On Market

  Last Listing Agent Marina Tramontozzi True North Realty

  One Seal Harbor Rd Unit 604, Winthrop, MA 02152
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  /36

  Est $687,081 Not Listed For Sale

  404 Revere St, Winthrop, MA 02152

  • 3 Beds
  • 3 Baths
  • 1,563 Sq Ft
  • Built 1900

  404 Revere St, Winthrop, MA 02152

  Last Sold Summary

  • 3% Below List Price
  • $454/SF
  • 21 Days On Market

  Last Sold Price $710,000

  Last Listing Agent Nicole Bettano Lantern Residential

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