Homes Under $500K in Winthrop, MA

Hide Map

17 Listings

Map

17 Listings

Open house Sun, Oct 4 · 10:30 AM27

17 listings

Homes Under $500K in Winthrop, MA

Hide Map

17 Listings

Map

Homes Under $500K in Winthrop, MA

17 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Open house Sun, Oct 4 · 10:30 AM27

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Active

$349,900

2 bd · 1 ba · 811 sqft

900 Governors Dr #37, Winthrop, MA

Brandon Dervishian · Lyv Realty

15Active

$260,000

1 bd · 1 ba · 667 sqft

100 Governors Drive #2, Winthrop, MA

Pat Sullivan · Century 21 Seaport

25Active

$459,900

2 bd · 1 ba · 805 sqft

43 Sagamore Ave #1, Winthrop, MA

Katelyn E. Sullivan · Coldwell Banker Realty - Boston

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Open house Sun, Oct 4 · 10:30 AM10Active

$309,900

1 bd · 1 ba · 720 sqft

483 Shirley St. #6a, Winthrop, MA

Sharon Tallent · Compass

17Active

$475,000

2 bd · 2 ba · 903 sqft

34 Underhill Street #4, Winthrop, MA

Reserve Team · Reference Real Estate

18Active

$499,900

1 bd · 1 ba · 623 sqft

130 Shirley Street #330, Winthrop, MA

Open house Sun, Oct 4 · 11:00 AM18Active

$473,900

1 bd · 1 ba · 693 sqft

10 Somerset U.305, Winthrop, MA

Charlesgate New Development Team · Charlesgate Realty Group, llc

Open house Sun, Oct 4 · 12:00 PM19Active

$399,900

1 bd · 1 ba · 500 sqft

22 Pauline St. #3, Winthrop, MA

Highland Group · Compass

Open house Sun, Oct 4 · 12:00 PM20Active

$419,900

1 bd · 1 ba · 525 sqft

22 Pauline St. #5, Winthrop, MA

Highland Group · Compass

14Active

$350,000

2 bd · 1 ba · 649 sqft

175 Shirley Street #5, Winthrop, MA

7Active

$219,999

1 bd · 1 ba · 350 sqft

229 Washington Ave #3a, Winthrop, MA

Price ReducedOpen house Sun, Oct 4 · 11:00 AM10Active

$397,900

1 bd · 1 ba · 546 sqft

10 Somerset #U304, Winthrop, MA

Charlesgate New Development Team · Charlesgate Realty Group, llc

Price ReducedOpen house Sun, Oct 4 · 11:00 AM15Active

$499,000

2 bd · 1 ba · 928 sqft

16 Billows Street #B, Winthrop, MA

Reserve Team · Reference Real Estate

Price ReducedOpen house Sun, Oct 4 · 11:00 AM20Active

$499,000

1 bd · 1 ba · 974 sqft

1 Seal Harbor Rd #812, Winthrop, MA

Peggie Gilbert · Coldwell Banker Peggy Carter Team

Price Reduced39Active

$479,900

1 bd · 1 ba · 947 sqft

1 Seal Harbor #210, Winthrop, MA

Rita Angelesco · LAER Realty Partners

Price Reduced26Active

$365,000

2 bd · 1 ba · 677 sqft

53 Trident Ave #301, Winthrop, MA

Amanda Woodward · Coldwell Banker Realty - Boston

3Active

$340,000

2 bd · 1 ba · 772 sqft

800 Governors Dr #6, Winthrop, MA

Listing data & MLS disclosures

MLS Property Information Network (MLS PIN): The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-10-03 07:05:00 UTC

Winthrop housing market

September 2026 · This period is still settling

Selling at 98.2% of asking price

Buyers here are paying below asking. MLS · 16 sales · as of Sep 25, 2026

Homes on the market · MLS, as of Sep 25, 2026–Sep 27, 2026

Median list price: $620,000
Homes for sale: 68
Median days on market: 47 days

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 10, 2026

Median home size: 1,880 sq. ft.

Winthrop, MA community profile

Area: 3.2 sq. mi.

Source: HJN community data

Explore Winthrop homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Listing data & MLS disclosures

MLS Property Information Network (MLS PIN): The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-10-03 07:05:00 UTC

Winthrop, MA community profile

Area: 3.2 sq. mi.

Source: HJN community data

Winthrop housing market

September 2026 · This period is still settling

Selling at 98.2% of asking price

Buyers here are paying below asking. MLS · 16 sales · as of Sep 25, 2026

Homes on the market · MLS, as of Sep 25, 2026–Sep 27, 2026

Median list price: $620,000
Homes for sale: 68
Median days on market: 47 days

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 10, 2026

Median home size: 1,880 sq. ft.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Winthrop housing market

Homes on the market · MLS, as of Sep 25, 2026–Sep 27, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 10, 2026

Winthrop, MA community profile

Explore Winthrop homes

Your local brokerage

Listing data & MLS disclosures

Winthrop, MA community profile

Winthrop housing market

Homes on the market · MLS, as of Sep 25, 2026–Sep 27, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 10, 2026