Winthrop, MA Homes

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  /21

  $1,030,000

  • 2 Beds
  • 2 Baths
  • 1,975 Sq Ft

  550 Pleasant St Unit 506, Winthrop, MA 02152

  Penthouse Waterfront Luxury at Atlantis Marina – Oversized Boat Slip Included!Experience sophisticated coastal living in this stunning top-floor corner penthouse at Atlantis Marina, offering sweeping water views and panoramic Boston skyline vistas. This rare fifth-floor residence combines luxury, space, and an unbeatable location in the charming seaside town of Winthrop.This exceptional

  Jessica Pumphret Blue Sky Realty

  550 Pleasant St Unit 506, Winthrop, MA 02152
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  /8

  $2,300 total monthly price

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

  23 Tafts Ave Unit 2, Winthrop, MA 02152

  Welcome to 23 Tafts Ave #2! A cozy beach cottage–style apartment in the sought-after Point Shirley neighborhood of Winthrop, available for rent 4/1. This charming 1-bedroom, 1-bath, second-floor unit offers 700 sq ft of recently renovated living space with fresh paint and new flooring throughout. Enjoy abundant natural light and ocean views from the bedroom, plus the unbeatable convenience of

  Ryan Wilson Keller Williams Realty

  23 Tafts Ave Unit 2, Winthrop, MA 02152
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  /25

  $670,000 Sold Sep 16, 2025

  162 Shirley St Unit 164, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,413 Sq Ft
  • Built 1884

  Last Sold Summary

  • 8% Below List Price
  • $474/SF
  • 76 Days On Market

  Current Estimated Value $684,167

  Last Listing Agent Jenny Golic Lantern Residential

  162 Shirley St Unit 164, Winthrop, MA 02152
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  /17

  Est $585,007 Not Listed For Sale

  500 Winthrop St, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 984 Sq Ft
  • Built 1960

  500 Winthrop St, Winthrop, MA 02152

  Last Sold Summary

  • 5% Above List Price
  • $565/SF
  • 24 Days On Market

  Last Sold Price $556,000

  Last Listing Agent Mary Ann Cash Charlesgate Realty Group, llc
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  /26

  $1,650,000

  • 6 Beds
  • 6 Baths
  • 4,122 Sq Ft

  304 Shirley St, Winthrop, MA 02152

  Situated just steps from the sand, 304 Shirley presents a rare opportunity to own a fully occupied 6-unit building in one of Winthrop's most desirable seaside neighborhoods. Each unit is a well-maintained 1-bedroom, offering consistent rental income and strong tenant demand. This beachside property is perfectly positioned near local shops, restaurants, and public transportation, making it a

  Reserve Team Reference Real Estate

  304 Shirley St, Winthrop, MA 02152
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  /38

  $2,100 total monthly price

  • Studio
  • 1 Bath
  • 300 Sq Ft
  • Condo for Rent

  77 Harbor View Ave Unit B, Winthrop, MA 02152

  Welcome to our newly renovated apartment in the beautiful location of Winthrop, MA. This cozy studio apartment offers a modern living space with stunning water views of Boston Harbor and the Atlantic Ocean. The apartment features a mini split AC/Heating system, ensuring a comfortable temperature all year round. Step outside and enjoy the serene atmosphere, with the outdoor fire pit, perfect for

  77 Harbor View Ave Unit B, Winthrop, MA 02152
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  /20

  $625,000 Sold Dec 03, 2025

  184 Woodside Ave Unit 1, Winthrop, MA 02152

  • 3 Beds
  • 1 Bath
  • 1,138 Sq Ft
  • Built 1880

  Last Sold Summary

  • 1% Below List Price
  • $549/SF
  • 12 Days On Market

  Current Estimated Value $614,550

  Last Listing Agent Michael Forcillo Coldwell Banker Peggy Carter Team

  184 Woodside Ave Unit 1, Winthrop, MA 02152
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  /30

  Est $754,968 Not Listed For Sale

  157 Morton St, Winthrop, MA 02152

  • 4 Beds
  • 2 Baths
  • 2,079 Sq Ft
  • Built 1952

  157 Morton St, Winthrop, MA 02152

  Last Sold Summary

  • 7% Above List Price
  • $341/SF
  • 2 Days On Market

  Last Sold Price $708,250

  Last Listing Agent Eclipse Group Cameron Real Estate Group
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  /16

  $1,050,000

  • 2 Beds
  • 2.5 Baths
  • 1,785 Sq Ft

  1001 Shirley St Unit 5, Winthrop, MA 02152

  Welcome to Unit 5 at The Pearl, a boutique coastal residence at 1001 Shirley Street, where refined design meets oceanfront living. This thoughtfully crafted home offers sweeping Atlantic views and a private ocean facing balcony, creating a daily connection to the water that few properties can match. Inside, the space is defined by clean architectural lines, generous ceiling height, and a layout

  Reserve Team Reference Real Estate

  1001 Shirley St Unit 5, Winthrop, MA 02152
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  /9

  $2,900 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Apartment for Rent

  295 Shirley St Unit 1, Winthrop, MA 02152

  Bright and spacious 2 bedroom 1.5 bath deleaded apartment with off -street parking, in-unit laundry and golf course views! The modern and large eat-in kitchen features granite countertops, tile floors and stainless appliances. Both bathrooms are renovated and neutral. Lots of closet space, hardwood floors throughout in this convenient ground floor unit with parking steps to the door. Great

  Erica Gore Century 21 Seaport

  295 Shirley St Unit 1, Winthrop, MA 02152
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  /22

  $570,000 Sold Jan 20, 2026

  87 Hermon St, Winthrop, MA 02152

  • 3 Beds
  • 1 Bath
  • 1,182 Sq Ft
  • Built 1870

  Last Sold Summary

  • 4% Above List Price
  • $482/SF
  • 3 Days On Market

  Current Estimated Value $560,016

  Last Listing Agent James Polino Compass

  87 Hermon St, Winthrop, MA 02152
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  /21

  Est $742,064 Not Listed For Sale

  58 Banks St, Winthrop, MA 02152

  • 3 Beds
  • 3 Baths
  • 1,788 Sq Ft
  • Built 1950

  58 Banks St, Winthrop, MA 02152

  Last Sold Summary

  • 6% Above List Price
  • $391/SF
  • 7 Days On Market

  Last Sold Price $700,000

  Last Listing Agent Realty Boston Team Century 21 Cityside
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  /14

  $829,999

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft

  876 Shirley St Unit 1, Winthrop, MA 02152

  Direct Ocean Front Living. Feel like you're on vacation every day! This spacious 2 level, 7 room, 4 bed, 2 bath condo is located Directly on Yirrell Beach. The sand in your own back yard. Ocean breeze and sounds of the waves crashing onto the shore, are sure to relax you after a long day. Featuring beautiful cherry hard wood floors, Family room, Formal dining room, ( Living room-could be master

  Jim Iannuzzi Amo Realty - Boston City Properties

  876 Shirley St Unit 1, Winthrop, MA 02152
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  /23

  $2,650 total monthly price

  • 2 Beds
  • 1 Bath
  • 9,999 Sq Ft
  • Condo for Rent

  288 Pleasant St Unit 1, Winthrop, MA 02152

  VIRTUAL TOUR AVAILABLE!- 2 Bedroom in Pleasant St Winthrop - Available for April 1st- Heat and Hot Water Included- Laundry in Building- Student-Friendly- Spacious unit with large yard and renovated appliances - Hardwood Floors- Parking included - Public Transportation: Green Line, (B), Sutherland Rd.

  288 Pleasant St Unit 1, Winthrop, MA 02152
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  /27

  $800,000 Sold Jul 14, 2025

  77 Otis St, Winthrop, MA 02152

  • 4 Beds
  • 2 Baths
  • 1,769 Sq Ft
  • Built 1912

  Last Sold Summary

  • 4% Below List Price
  • $452/SF
  • 41 Days On Market

  Current Estimated Value $799,253

  Last Listing Agent Molly Walker Coldwell Banker Realty - Scituate

  77 Otis St, Winthrop, MA 02152
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  /24

  Est $892,467 Not Listed For Sale

  44 Fairview St, Winthrop, MA 02152

  • 5 Beds
  • 2 Baths
  • 2,413 Sq Ft
  • Built 1911

  44 Fairview St, Winthrop, MA 02152

  Last Sold Summary

  • 6% Below List Price
  • $393/SF
  • 12 Days On Market

  Last Sold Price $949,000

  Last Listing Agent Leighann Eruzione Lantern Residential
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  /30

  $639,000 Open Sun 12PM - 1:30PM

  • 2 Beds
  • 1 Bath
  • 1,213 Sq Ft

  51 Harbor View Ave Unit 1, Winthrop, MA 02152

  Harborview Condo with Sweeping ViewsWelcome to The Condos at 51 Harborview. This beautifully renovated condo is perched high on the hill with stunning harbor and city skyline views. Unit 1 features two bedrooms and one bath, including a spacious primary with walk-in closet, and a brand-new kitchen and bath with quartz countertops, tile backsplash, stainless steel appliances, and luxury vinyl

  Susan Doig Donnelly + Co.

  51 Harbor View Ave Unit 1, Winthrop, MA 02152
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  /22

  $3,000 total monthly price

  • 4 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Apartment for Rent

  62 Locust St Unit 1, Winthrop, MA 02152

  DINNING ROOM CAN BE USED AS A BEDROOM. Be the first to live in this beautifully built modern 3/4-bedroom, 1-bath apartment located in the highly desirable coastal town of Winthrop. This fresh new construction features an open-concept layout, bright natural light, and quality finishes throughout. In between, we have the look of a quaint and friendly New England town with shops, parks, inns, and

  Stephane Abelard Block Realty

  62 Locust St Unit 1, Winthrop, MA 02152
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  /31

  $390,000 Sold Sep 10, 2025

  23 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 679 Sq Ft
  • Built 1902

  Last Sold Summary

  • 2% Below List Price
  • $574/SF
  • 5 Days On Market

  Last Listing Agent Mariel Yovino Compass

  23 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
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  /28

  Est $571,189 Not Listed For Sale

  26 Amelia Ave, Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1953

  26 Amelia Ave, Winthrop, MA 02152

  Last Sold Summary

  • 4% Above List Price
  • $501/SF
  • 23 Days On Market

  Last Sold Price $551,000

  Last Listing Agent James Polino Compass
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  /23

  $749,900

  • 2 Beds
  • 2 Baths
  • 1,113 Sq Ft

  140 Shirley St Unit 310, Winthrop, MA 02152

  Special Financing Available (30yr Fixed @ 5.75% No PMI). Discover the perfect blend of modern design and seaside charm at 140 Shirley Street, Winthrop’s newest boutique condominium residence—just steps from the shoreline of Winthrop Beach. This two-bedroom, two-bath home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style and high-end finishes.

  Kovacs Savage Team Byrnes Real Estate Group LLC

  140 Shirley St Unit 310, Winthrop, MA 02152
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  /11

  $1,750 total monthly price

  • Studio
  • 1 Bath
  • 225 Sq Ft
  • Condo for Rent

  90 Winthrop Shore Dr Unit 3, Winthrop, MA 02152

  90 Winthrop Shore Dr Unit 3, Winthrop, MA 02152
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  /41

  $975,000 Sold Feb 04, 2026

  5 Quincy Ave, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 2,820 Sq Ft
  • Built 1917

  Last Sold Summary

  • 3% Above List Price
  • $346/SF
  • 46 Days On Market

  Current Estimated Value $937,129

  Last Listing Agent William Raye William Raveis R.E. & Home Services

  5 Quincy Ave, Winthrop, MA 02152
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  /26

  Est $453,297 Not Listed For Sale

  249 Winthrop Shore Dr Unit 1, Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 940 Sq Ft
  • Built 1900

  249 Winthrop Shore Dr Unit 1, Winthrop, MA 02152

  Last Sold Summary

  • 1% Above List Price
  • $479/SF
  • 12 Days On Market

  Last Sold Price $450,000

  Last Listing Agent Ryan Wilson Keller Williams Realty
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  /21

  $629,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft

  10 Somerset Ave Unit 201, Winthrop, MA 02152

  Welcome to Unit 201 at The Somerset—Winthrop’s premier boutique condo community where coastal charm meets modern design. This spacious 2-bed, 2-bath home features an open-concept layout with a large living/dining area perfect for entertaining or relaxing. A generous kitchen island anchors the space and faces the front of the building, inviting natural light and a welcoming flow. Enjoy quartz

  Charlesgate New Development Team Charlesgate Realty Group, llc

  10 Somerset Ave Unit 201, Winthrop, MA 02152
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  /14

  $3,300 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft
  • Apartment for Rent

  95 Hermon St Unit 1, Winthrop, MA 02152

  Spacious and bright deleaded 3-bedroom apartment located in the heart of Winthrop Center! This large second floor apartment offers the perfect blend of comfort and convenience—just steps from schools, parks, shopping, and restaurants.Enjoy an oversized master bedroom with access to a private balcony, ideal for morning coffee or evening relaxation. The large eat-in kitchen provides plenty of room

  Erica Gore Century 21 Seaport

  95 Hermon St Unit 1, Winthrop, MA 02152
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  /23

  $1,050,000 Sold Jan 05, 2026

  191 Court Rd Unit 3, Winthrop, MA 02152

  • 4 Beds
  • 3.5 Baths
  • 2,575 Sq Ft
  • Built 1920

  Last Sold Summary

  • 2% Below List Price
  • $408/SF
  • 11 Days On Market

  Current Estimated Value $1,050,263

  Last Listing Agent Reserve Team Reference Real Estate

  191 Court Rd Unit 3, Winthrop, MA 02152
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  /29

  Est $768,090 Not Listed For Sale

  239 Winthrop Shore Dr, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,501 Sq Ft
  • Built 1880

  239 Winthrop Shore Dr, Winthrop, MA 02152

  Last Sold Summary

  • 14% Below List Price
  • $597/SF
  • 1 Day On Market

  Last Sold Price $896,000

  Last Listing Agent The Reference Group Reference Real Estate
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  /27

  $1,280,000

  • 6 Beds
  • 3.5 Baths
  • 3,400 Sq Ft

  47 Bellevue Ave, Winthrop, MA 02152

  Introducing coastal living in this luxurious two-family home set on one of Winthrop’s most exclusive seaside streets. Just minutes from downtown Boston, this rare offering blends high-end finishes with exceptional investment potential. Additional in-law/guest suite possibilities create the opportunity for a dynamic property with multiple income streams or an elegant multigenerational retreat.

  Jessica Pumphret Blue Sky Realty

  47 Bellevue Ave, Winthrop, MA 02152
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  /17

  $3,700 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Condo for Rent

  953 Shirley St Unit 2, Winthrop, MA 02152

  Stylish 3-Bedroom Apartment by the shores of Winthrop!!Welcome to your new home in Boston’s vibrant Winthrop neighborhood! This spacious and updated 3-bedroom, 1-bathroom apartment offers comfort and convenience in a prime location. Each bedroom is generously sized, perfect for creating your own personal retreat. The open living area boasts ample natural light, creating a warm and

  953 Shirley St Unit 2, Winthrop, MA 02152
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  /34

  $575,000 Sold Jul 01, 2025

  12 Sewall Ave Unit 1, Winthrop, MA 02152

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

  Last Sold Summary

  • 3% Above List Price
  • $642/SF
  • 6 Days On Market

  Last Listing Agent Jorge Betancur Century 21 Mario Real Estate

  12 Sewall Ave Unit 1, Winthrop, MA 02152
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  /30

  Est $361,825 Not Listed For Sale

  222 Winthrop Shore Dr Unit 3, Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 736 Sq Ft
  • Built 1964

  222 Winthrop Shore Dr Unit 3, Winthrop, MA 02152

  Last Sold Summary

  • 3% Above List Price
  • $476/SF
  • 84 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Antonio Ferreira Gifted Realty Group, LLC
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  /22

  $649,995 Pending

  • 1 Bed
  • 1 Bath
  • 910 Sq Ft

  3 Seal Harbor Rd Unit 133, Winthrop, MA 02152

  Enter coastal luxury living at The Seal Harbor Condominiums! This 1 bed/1 bath unique unit doesn't just offer an unbeatable location- it has been meticulously renovated from top to bottom with premium finishes & custom touches throughout. Updates include new tile flooring, all-new wooden six-panel doors with glass knobs, fully rewired living room, kitchen, and entryway for modern convenience.

  Christine Goldstein Lyv Realty

  3 Seal Harbor Rd Unit 133, Winthrop, MA 02152
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  /8

  $2,200 total monthly price

  • 1 Bed
  • 1 Bath
  • 9,999 Sq Ft
  • Apartment for Rent

  220 Winthrop St Unit 301, Winthrop, MA 02152

  Available NOW! Discover this brand-new, fully renovated one-bedroom, one-bathroom apartment located in Winthrop center. Situated in an elevator building, the apartment features gleaming hardwood floors, an open concept living room filled with natural light, and a sleek kitchen equipped with stainless steel appliances, including a dishwasher, gas stove, refrigerator, and microwave. The spacious

  Mario Fiume Anzalone Realty

  220 Winthrop St Unit 301, Winthrop, MA 02152
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  /30

  $765,000 Sold May 16, 2025

  127 Bowdoin St, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,698 Sq Ft
  • Built 1910

  Last Sold Summary

  • 2% Above List Price
  • $451/SF
  • 22 Days On Market

  Current Estimated Value $782,185

  Last Listing Agent Leighann Eruzione Lantern Residential

  127 Bowdoin St, Winthrop, MA 02152
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  /39

  Est $747,680 Not Listed For Sale

  41 Hawthorn Ave, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 2,224 Sq Ft
  • Built 1954

  41 Hawthorn Ave, Winthrop, MA 02152

  Last Sold Summary

  • $337/SF
  • 3 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Linda Calla Cottage Hill Real Estate
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  /40

  $1,150,000 Pending

  • 6 Beds
  • 2.5 Baths
  • 3,458 Sq Ft

  66 Lowell Rd, Winthrop, MA 02152

  One of a kind. 10+ rooms of meticulousness combining warmth and character. Built 1925 in the New England coastal Maze area, nearby Cottage Park Yacht Club. 3 solid wood entry doors lead to amazing flow on main level with sunny exposures thru oversized windows. Designed by MIT architect John Whitmore. Flood insurance is NOT required in this sought after location. Gas fireplace in living room adds

  Stacey Steck Gibson Sotheby's International Realty

  66 Lowell Rd, Winthrop, MA 02152
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  /7

  $1,750 total monthly price

  • Studio
  • 1 Bath
  • 300 Sq Ft
  • Condo for Rent

  94 Winthrop Shore Dr, Winthrop, MA 02152

  Rent$1,750Avail DateNOW (01/01/2026)BedsStudioBaths1Rent IncludesHot WaterSquare Footage225

  94 Winthrop Shore Dr, Winthrop, MA 02152
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  /28

  $665,000 Sold Jun 18, 2025

  128 Lincoln St, Winthrop, MA 02152

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1966

  Last Sold Summary

  • 11% Above List Price
  • $416/SF
  • 6 Days On Market

  Current Estimated Value $680,745

  Last Listing Agent Carol Henriquez Coldwell Banker Realty - Cambridge

  128 Lincoln St, Winthrop, MA 02152
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  /24

  Est $725,700 Not Listed For Sale

  15 Myrtle Ave, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,687 Sq Ft
  • Built 1890

  15 Myrtle Ave, Winthrop, MA 02152

  Last Sold Summary

  • 9% Below List Price
  • $474/SF
  • 8 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Leighann Eruzione Lantern Residential

Showing Results 161 - 200, Page 5 of 18