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58 listings

Homes for Sale in Winthrop, MA

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24 of 58 Listings

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24 of 58 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Active

$975,000

3 bd · 3 ba · 2,100 sqft

200 Main St #1, Winthrop, MA

15Active

$549,000

2 bd · 1 ba · 928 sqft

16 Billows Street #B, Winthrop, MA

19Active

$519,000

1 bd · 1 ba · 974 sqft

1 Seal Harbor Rd #812, Winthrop, MA

Price Reduced31Active

$675,000

3 bd · 3 ba · 1,510 sqft

189 Shirley #2, Winthrop, MA

Price Reduced37Active

$829,900

5 bd · 3 ba · 2,437 sqft

43 Dolphin Ave, Winthrop, MA

42Active

$859,900

2 bd · 2 ba · 1,674 sqft

3 Seal Harbor #336, Winthrop, MA

Price Reduced39Active

$489,900

1 bd · 1 ba · 947 sqft

1 Seal Harbor #210, Winthrop, MA

Price Reduced17Active

$449,900

2 bd · 2 ba · 879 sqft

34R Underhill St #3, Winthrop, MA

42Active

$2,380,000

5 bd · 6 ba · 6,224 sqft

174 Bartlett Road, Winthrop, MA

Price Reduced21Active

$715,000

4 bd · 2 ba · 1,586 sqft

52 Pebble Ave, Winthrop, MA

Price Reduced42Active

$869,900

3 bd · 3 ba · 2,125 sqft

37 Loring Rd., Winthrop, MA

24Active

$725,000

2 bd · 2 ba · 1,113 sqft

140 Shirley Street #250, Winthrop, MA

18Active

$499,900

1 bd · 1 ba · 623 sqft

140 Shirley Street #330, Winthrop, MA

24Active

$589,900

2 bd · 1 ba · 782 sqft

140 Shirley Street #220, Winthrop, MA

29Active

$650,000

3 bd · 2 ba · 800 sqft

496 Winthrop St, Winthrop, MA

20Active

$485,000

1 bd · 2 ba · 591 sqft

600 Shirley St # 7, Winthrop, MA

Price Reduced24Active

$615,000

2 bd · 2 ba · 1,203 sqft

1 Seal Harbor Rd #815, Winthrop, MA

Price Reduced28Active

$499,000

2 bd · 1 ba · 1,006 sqft

52 Trident Ave #52, Winthrop, MA

Price Reduced25Active

$840,000

3 bd · 3 ba · 1,837 sqft

27 Billows St, Winthrop, MA

Price Reduced17Active

$399,900

2 bd · 1 ba · 664 sqft

53 Trident # 303, Winthrop, MA

3Active

$340,000

2 bd · 1 ba · 772 sqft

800 Governors Dr #6, Winthrop, MA

Price Reduced40Active

$1,199,999

4 bd · 4 ba · 1,904 sqft

70 Edgehill Rd, Winthrop, MA

Price Reduced17Active

$299,999

1 bd · 1 ba · 351 sqft

600 Shirley St #11, Winthrop, MA

Price Reduced30Active

$799,999

4 bd · 2 ba · 2,000 sqft

876 Shirley Street #1, Winthrop, MA

1 2 3

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: 2026-09-02 07:06:00 UTC

Winthrop housing market

July 2026

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 10 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 31, 2026

Median sale price: $725,000$467,500–$947,000 typical range
Price per sq. ft.: $372
Sales: 15
Paid in cash: 26.7%

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

Median list price: $649,000

Winthrop, MA community profile

Area: 3.2 sq. mi.

Source: HJN community data

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

New construction
With a pool

Nearby areas

ZIP codes

02135 (123)
02116 (107)
02127 (100)
02128 (98)
02118 (95)
02169 (89)
02155 (82)
02301 (76)

Cities

Boston (1,300)
Newton (174)
Brookline (140)
Brockton (124)
Cambridge (123)
Quincy (122)
Lowell (114)
Somerville (112)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

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: 2026-09-02 07:06:00 UTC

Winthrop, MA Homes for Sale — Page 2 | Realty.com

Nearby areas

ZIP codes

02135 (123)
02116 (107)
02127 (100)
02128 (98)
02118 (95)
02169 (89)
02155 (82)
02301 (76)

Cities

Boston (1,300)
Newton (174)
Brookline (140)
Brockton (124)
Cambridge (123)
Quincy (122)
Lowell (114)
Somerville (112)

Winthrop, MA community profile

Area: 3.2 sq. mi.

Source: HJN community data

Winthrop housing market

July 2026

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 10 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 31, 2026

Median sale price: $725,000$467,500–$947,000 typical range
Price per sq. ft.: $372
Sales: 15
Paid in cash: 26.7%

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

Median list price: $649,000

Homes for sale

Median days on market

24 days

Price trend · Assessor repeat sales, as of Jul 31, 2026

Year-over-year: -14.6%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 14, 2026

Median home size: 1,715 sq. ft.