Downtown Winthrop, MA homes for sale & real estate

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NEW 17 HRS AGO

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
UPSCALE 2 BEDROOM, 2 BATH TOP FLOOR UNIT WITH ROOFTOP EXCLUSIVE OUTDOOR DECK. .. .. .A two year old renovation and a must see! Bright sun-filled condo with a spacious kitchen/living room combo with plenty of cabinets and huge center island with pretty pendant lighting. .. .. .perfect for entertaining and personal enjoyment. Two large bedrooms, one with it's own full bath and the other bath has a corner shower stall and stackable laundry. Beautiful hardwood floors throughout, stainless appliances, central air conditioning, recessed lighting, pet friendly and off street parking! * * * * OPEN HOUSE SUN. 9/21 from 2:30-3:30 * * * *

$529,900

2 beds2 baths800 sq ft

35 Somerset Ave #6, Winthrop, MA 02152

Corner shower stall • Huge center island • Top floor unit

3D WALKTHROUGH

ABOUT THIS HOME
Downtown Winthrop, 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

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Welcome to 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. The Somerset offers exceptional amenities, including a fitness room, elevator, and a cozy resident lounge ideal for remote work or casual gatherings. Just moments from sandy beaches, waterfront parks, and local restaurants—with easy access to downtown Boston via the Blue Line or seasonal fe

$414,000

1 bed1 bath546 sq ft

10 Somerset #304, Winthrop, MA 02152

Quartz countertops • Open-concept kitchen • Elevator

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
THIS INCREDIBLE AND PRIVATE LOCATION OFFERS SO MUCH NATURAL BEAUTY. .. .. .. .Stunning Winthrop harbor views from this totally renovated 3 BR, 2 full bath seaside single with garage. Quality upgrades, Open Floor plan, crown moldings, stunning accent wall and amazing oversized windows that invite in amazing views and natural sunlight! Beautiful quartz kitchen with dual cabinet colors, Stainless appliances and center island all makes for an ideal set up for entertaining. Gorgeous designer baths with rain shower fixtures, black accent hardware throughout, and new golden oak floors all make this home a place you will want for your own. A bonus room in the basement adds to the generous living s

$924,900

3 beds2 baths1,905 sq ft

12 Winthrop St, Winthrop, MA 02152

Totally renovated • Stainless appliances • Quartz kitchen

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Welcome to this well-maintained 2-family property located in the desirable Lower Highlands neighborhood of Winthrop by the Sea. This home is just a short stroll to the beach, shops and local dining! Perfect for homeowners seeking rental income or investors alike! The main unit features 3 bedrooms, 1 bathroom, and a bright, open, inviting living area. A finished family room and half bath on the lower level provide additional space for entertaining, relaxing, or working from home. The second unit, conveniently located on the lower level, offers 1 bedroom and 1 full bath, ideal for extended family, guests, or rental opportunities. Enjoy outdoor living with a large front deck perfect for entert

$850,000

4 beds2.5 baths2,000 sq ft

89-91 Sagamore Ave, Winthrop, MA 02152

Finished family room • Large front deck • 5,000 sq ft lot

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 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 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 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 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 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 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 80 Shirley St, Winthrop, MA 02152, 4 beds, 2 baths

$1,050,000

4 beds2 baths2,366 sq ft

80 Shirley St, 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 80 Shirley St #2, Winthrop, MA 02152, 3 beds, 2 baths

$599,000

3 beds2 baths1,252 sq ft

80 Shirley St #2, 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 80 Shirley St #1, Winthrop, MA 02152, 1 bed, 1 bath

$449,900

1 bed1 bath836 sq ft

80 Shirley St #1, Winthrop, MA 02152

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ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Welcome home to 41 Sargent Street. Set on one of Winthrop’s most desirable picturesque tree-lined streets and just a short walk to the ocean, this 3 Bed, 2 Bath lovely Colonial is just waiting to be lovingly restored for it's next chapter. Offering convenience and charm and a thoughtful flow throughout. With a large sun-filled kitchen, 1st floor laundry & full bath, and a vast & versatile living space, the possibilities are endless. Hardwood floors lie hidden beneath the carpet, ready to shine again. Upstairs you'll find generously sized bedrooms, another full bath, plus a walk-up attic for even more potential. Start your day with coffee on the charming covered porch, then

$559,900

3 beds2 baths1,724 sq ft

41 Sargent St, Winthrop, MA 02152

5,993 sq ft lot • Very walkable

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
15 Ocean Dr #105 delivers flexible two-level living with dramatic ceiling height and oversized windows just minutes to the beach. Newly renovated with 2 luxurious full baths, in-unit laundry, central A/C, one deeded parking, and access to a common roof deck. Smart layout features a main kitchen on the upper level and a lower-level kitchenette with a separate entrance-ideal for guests, work-from-home, or a private retreat. Well-maintained building; water & sewer included in condo fee. Easy and fast commute to Boston and Logan Airport. Prime walkable location near Winthrop Beach, Norman Playground, local restaurants, Winthrop Golf Club, and the marina’s waterfront views.

$449,900

2 beds2 baths1,460 sq ft

15 Ocean Dr #105, Winthrop, MA 02152

$416 HOA • Community pool • Somewhat walkable

ABOUT THIS HOME
Downtown Winthrop, 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

5,282 sq ft lot • Garage • Very walkable

ABOUT THIS HOME
Downtown Winthrop, 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

$400 HOA • Somewhat walkable

ABOUT THIS HOME
Downtown Winthrop, 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

$237 HOA • Very walkable

ABOUT THIS HOME
Downtown Winthrop, 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

5,300 sq ft lot • 2 garage spots • Very walkable

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 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 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 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 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 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 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 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 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 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 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

Average home prices near Downtown Winthrop, MA

Cities

Neighborhoods

Logan Airport / Jeffries Point homes for sale
$737,000
Admirals Hill homes for sale
East Boston homes for sale
$719,000
Beachmont homes for sale
$724,998
Maverick Square homes for sale
$662,500
West Revere homes for sale
$612,450
Orient Heights homes for sale
$665,000
Jeffries Point homes for sale
$720,000
Crescent Beach homes for sale
$592,000
Whinthrop Highlands homes for sale
$925,000

Downtown Winthrop, MA real estate trends

All Home Types trends in Downtown Winthrop, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$839,500

+29.4% 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

Downtown Winthrop, MA

$839,500

+29.4%

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