Winthrop Town, MA homes for sale & real estate

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NEW 5 HRS AGO

ABOUT THIS HOME
Winthrop Town, MA Homes for Sale
Welcome to the "Maze!" This Whittemore designed home is solidly built and filled with character and charm. With great bones and endless potential, this 4+ bedroom, 2.5 bath single is the perfect canvas to create space you've been dreaming of, all in one of Winthrop's most sought after locations. Some of the wonderful features include a wood-burning fireplace, bright eat in kitchen with appliances, 1/2 bath and french doors leading to a first floor home office. There are four bedrooms on the second floor and a full bath with loads of storage. Do you desire more space? Up to the third floor, you'll find another bedroom and a spacious unfinished room. The partially finished basemen

$780,000

5 beds2.5 baths1,923 sq ft

62 Lowell Rd, Winthrop, MA 02152

Off street parking • Eat in kitchen • 5,282 sq ft lot

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Winthrop Town, MA Homes for Sale
LOWEST PRICED CONDO IN WINTHROP. If you’ve been looking for a 1 bed 1 bath condo in the heart of Winthrop Shore, look no further. Conveniently located next to some of the best restaurants & shops in town, and only a street away from Winthrop Beach. HOA fee includes heat, hot water, and much more. Come make this hidden gem your own - and yes your pets are welcome! Just minutes from Boston, a commuters dream. Don't miss it.

$290,000

1 bed1 bath550 sq ft

483 Shirley St #4, Winthrop, MA 02152

Next to shops • Minutes from boston • Next to restaurants

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Winthrop Town, MA Homes for Sale
This two-level corner unit offers a rare blend of comfort and convenience in a well-constructed building just minutes from Boston. The open layout features a modern kitchen, gas fireplace, and hardwood floors throughout, with a freshly painted interior that feels move-in ready. Two outdoor spaces—a private roof deck and patio—extend your living options, while deeded parking plus abundant visitor parking add everyday ease. The home includes a full bath, half bath, and in-unit washer/dryer for practicality. Enjoy a short commute to downtown Boston, Logan Airport, and oceanfront access, making this location ideal for both work and leisure.

$585,000

1 bed1.5 baths1,039 sq ft

142 Pleasant St #2, Winthrop, MA 02152

Gas fireplace • Private roof deck • Corner unit

OPEN FRI, 4PM TO 6PM3D WALKTHROUGH

ABOUT THIS HOME
Winthrop Town, MA Homes for Sale
Welcome to 59 Crescent St in Winthrop. This well-kept bungalow offers 1,716 square feet of living space with 3 bedrooms and 2.5 bathrooms. The first floor includes a large living room with skylights, bay windows, hardwood floors, and recessed lighting, a dining area, and an updated kitchen with granite counters, stainless steel appliances, and a gas stove. Upstairs, you will find comfortable bedrooms with hardwood floors and a modern full bath. Outdoor space features a brand new deck, fenced yard, enclosed porch, and off-street parking. The home sits on a 6,125 square foot lot at the end of a quiet, dead-end street with few neighboring homes, providing added privacy. Just a short distance t

$729,900

3 beds2.5 baths1,716 sq ft

59 Crescent St, Winthrop, MA 02152

Brand new deck • Fenced yard • Large living room

OPEN SUN, 11AM TO 12:30PM

ABOUT THIS HOME
Winthrop Town, MA Homes for Sale
Borrowing inspiration from Nantucket and Martha's Vineyard, this single family home in the seaside town of Winthrop is a classic coastal New England residence. Recently renovated, this three bedroom, two bath home is impeccably designed; from the fireplace that first greets you in the living room to the soaking tub in the spa-like bathroom. An overly spacious kitchen with quartz countertops and stainless steel appliances lends itself to great times cooking and entertaining with friends and family; and the primary bedroom suite is the perfect cozy retreat. Located in the desirable "Maze' area, this home is close to several beaches, quaint shops and restaurants in Winthrop's Center and j

$899,900

3 beds2 baths1,883 sq ft

44 Birch Rd, Winthrop, MA 02152

Quartz countertops • Soaking tub • Spacious kitchen

Property at 10 Somerset #304, Winthrop, MA 02152, 1 bed, 1 bath

$414,000

1 bed1 bath546 sq ft

10 Somerset #304, Winthrop, MA 02152

Property at 144 Quincy Ave, Winthrop, MA 02152, 5 beds, 4 baths

$1,800,000

5 beds4 baths3,866 sq ft

144 Quincy Ave, Winthrop, MA 02152

Property at 900 Shirley St, Winthrop, MA 02152, 2 beds, 1 bath

$499,900

2 beds1 bath1,015 sq ft

900 Shirley St, Winthrop, MA 02152

Property at 2 Deane Ave, Winthrop, MA 02152, 4 beds, 2.5 baths

$925,000

4 beds2.5 baths2,397 sq ft

2 Deane Ave, Winthrop, MA 02152

Property at 12 Winthrop St, Winthrop, MA 02152, 3 beds, 2 baths

$924,900

3 beds2 baths1,905 sq ft

12 Winthrop St, Winthrop, MA 02152

Property at 23 Nahant Ave, Winthrop, MA 02152, 2 beds, 2 baths

$1,380,000

2 beds2 baths2,455 sq ft

23 Nahant Ave, Winthrop, MA 02152

Property at 23 Trident Ave #2, Winthrop, MA 02152, 4 beds, 1 bath

$499,900

4 beds1 bath1,369 sq ft

23 Trident Ave #2, Winthrop, MA 02152

Property at 279 Shirley St #2, Winthrop, MA 02152, 3 beds, 1 bath

$589,000

3 beds1 bath1,105 sq ft

279 Shirley St #2, Winthrop, MA 02152

Property at 42 Harborview Ave #2, Winthrop, MA 02152, 3 beds, 1.5 baths

$630,000

3 beds1.5 baths1,166 sq ft

42 Harborview Ave #2, Winthrop, MA 02152

Property at 66 Lowell Rd, Winthrop, MA 02152, 5 beds, 2.5 baths

$1,175,000

5 beds2.5 baths3,458 sq ft

66 Lowell Rd, Winthrop, MA 02152

Property at 89-91 Sagamore Ave, Winthrop, MA 02152, 4 beds, 2.5 baths

$850,000

4 beds2.5 baths2,000 sq ft

89-91 Sagamore Ave, Winthrop, MA 02152

Property at 10 Somerset #309, Winthrop, MA 02152, 1 bed, 1 bath

$569,160

1 bed1 bath729 sq ft

10 Somerset #309, Winthrop, MA 02152

Property at 174 Winthrop St #2, Winthrop, MA 02152, 3 beds, 2.5 baths

$739,900

3 beds2.5 baths1,973 sq ft

174 Winthrop St #2, Winthrop, MA 02152

Property at 191 Cottage Park Rd, Winthrop, MA 02152, 6 beds, 3.5 baths

$1,799,000

6 beds3.5 baths4,455 sq ft

191 Cottage Park Rd, Winthrop, MA 02152

Property at 16 Pebble Ave, Winthrop, MA 02152, 2 beds, 1 bath

$424,950

2 beds1 bath866 sq ft

16 Pebble Ave, Winthrop, MA 02152

Property at 550 Pleasant St #307, Winthrop, MA 02152, 1 bed, 1 bath

$549,900

1 bed1 bath1,153 sq ft

550 Pleasant St #307, Winthrop, MA 02152

Property at 212 Winthrop Shore Dr #1, Winthrop, MA 02152, 3 beds, 1.5 baths

$549,000

3 beds1.5 baths1,290 sq ft

212 Winthrop Shore Dr #1, Winthrop, MA 02152

Property at 800 Governors Dr #6, Winthrop, MA 02152, 2 beds, 1 bath

$340,000

2 beds1 bath772 sq ft

800 Governors Dr #6, Winthrop, MA 02152

Property at 916 Shirley #1, Winthrop, MA 02152, 3 beds, 2.5 baths

$1,200,000

3 beds2.5 baths1,700 sq ft

916 Shirley #1, Winthrop, MA 02152

Property at 54 Villa Ave #2, Winthrop, MA 02152, 3 beds, 2.5 baths

$861,000

3 beds2.5 baths2,115 sq ft

54 Villa Ave #2, Winthrop, MA 02152

Property at 50-52 Wilshire St, Winthrop, MA 02152, 5 beds, 2 baths

$1,300,000

5 beds2 baths2,212 sq ft

50-52 Wilshire St, Winthrop, MA 02152

Property at 10 Somerset #308, Winthrop, MA 02152, 1 bed, 1 bath

$602,436

1 bed1 bath774 sq ft

10 Somerset #308, Winthrop, MA 02152

Property at 181 Grovers Ave, Winthrop, MA 02152, 3 beds, 1.5 baths

$749,999

3 beds1.5 baths1,454 sq ft

181 Grovers Ave, Winthrop, MA 02152

Property at 600 Shirley St #15, Winthrop, MA 02152, 1 bath

$340,000

0 beds1 bath338 sq ft

600 Shirley St #15, Winthrop, MA 02152

Property at 191 Court Rd #3, Winthrop, MA 02152, 4 beds, 3.5 baths

$1,200,000

4 beds3.5 baths2,575 sq ft

191 Court Rd #3, Winthrop, MA 02152

Property at 1001 Shirley #3, Winthrop, MA 02152, 2 beds, 2.5 baths

$979,000

2 beds2.5 baths1,561 sq ft

1001 Shirley #3, Winthrop, MA 02152

Property at 10 Somerset #406, Winthrop, MA 02152, 2 beds, 2 baths

$655,000

2 beds2 baths985 sq ft

10 Somerset #406, Winthrop, MA 02152

Property at 1 Seal Harbor Rd #215, Winthrop, MA 02152, 2 beds, 2 baths

$630,000

2 beds2 baths1,203 sq ft

1 Seal Harbor Rd #215, Winthrop, MA 02152

Property at 24 Winthrop Shore Dr #2, Winthrop, MA 02152, 2 beds, 1 bath

$415,000

2 beds1 bath900 sq ft

24 Winthrop Shore Dr #2, Winthrop, MA 02152

Property at 3 Buckthorn Ter #2, Winthrop, MA 02152, 4 beds, 2 baths

$750,000

4 beds2 baths1,870 sq ft

3 Buckthorn Ter #2, Winthrop, MA 02152

Property at 54 Townsend, Winthrop, MA 02152, 4 beds, 2 baths

$650,000

4 beds2 baths1,483 sq ft

54 Townsend, Winthrop, MA 02152

Property at 100 Cottage Ave, Winthrop, MA 02152, 3 beds, 2.5 baths

$854,900

3 beds2.5 baths2,293 sq ft

100 Cottage Ave, Winthrop, MA 02152

Property at 136 Pauline St, Winthrop, MA 02152, 4 beds, 3.5 baths

$870,000

4 beds3.5 baths2,350 sq ft

136 Pauline St, Winthrop, MA 02152

Property at 148 Winthrop Shore Dr #5, Winthrop, MA 02152, 2 beds, 2 baths

$669,009

2 beds2 baths971 sq ft

148 Winthrop Shore Dr #5, Winthrop, MA 02152

Property at 876 Shirley #1, Winthrop, MA 02152, 4 beds, 2 baths

$829,999

4 beds2 baths2,000 sq ft

876 Shirley #1, Winthrop, MA 02152

Property at 328-330 Revere St, Winthrop, MA 02152, 5 beds, 2 baths

$1,170,000

5 beds2 baths2,151 sq ft

328-330 Revere St, Winthrop, MA 02152

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Average home prices near Winthrop Town, MA

Cities

Neighborhoods
Zip Codes

Logan Airport / Jeffries Point homes for sale
$725,000
Point Shirley homes for sale
Downtown Winthrop homes for sale
$699,900
East Boston homes for sale
$719,000
Beachmont homes for sale
$725,000
Orient Heights homes for sale
$627,000
Harbor View-Orient Heights homes for sale
$685,000
Jeffries Point homes for sale
$720,000
Whinthrop Highlands homes for sale
$1,047,500
Winthrop Beach homes for sale
$549,000

Winthrop Town, MA real estate trends

All Home Types trends in Winthrop Town, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$697,500

-3.8% YoY | Aug 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Aug 2025

Growth

% YoY

Winthrop Town, MA

$697,500

-3.8%

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