Downtown Winthrop, MA homes for sale & real estate

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OPEN SAT, 10:30AM TO 12PM

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
LAST STUDIO! 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

$399,000

1 bed1 bath546 sq ft

10 Somerset Unit 304S, Winthrop, MA 02152

Quartz countertops • Open-concept kitchen • Elevator

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
OPPORTUNITY KNOCKS. .. .. .. Two family with large yard is located right on the bus line with a very short ride to the T to Boston. There are 6 off street parking spaces! Some renovations as of 2001. The owner's unit is on the second and third floors with an open floor plan and lots of natural lighting. It contains a living room, dining area, kitchen, bath and one bedroom. The top floor consists of a sprawling main bedroom large enough to become 2 rooms. There are Boston skyline and marina views from the the top floor. The owner's unit has a great layout and good size rooms with lots of windows and laundry area of the kitchen. The first floor unit consists of a living room, kitchen, bath an

$799,900

4 beds2 baths2,103 sq ft

56 Main St, Winthrop, MA 02152

Natural lighting • Open floor plan • Off street parking

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Priced Well Below Market Price - Experience the best of coastal living just minutes from Boston—close to the city without the high prices! This bright and spacious home features soaring ceilings, abundant natural light, large rooms, and hardwood floors. The traditional dining room with a built-in cabinet adds classic charm, while the fully applianced kitchen offers warm wood cabinetry and an oversized pantry. Enjoy morning coffee or evening breezes on either of two private porches. Each unit includes its own washer and dryer in the basement, and the pet-friendly building is well-maintained with a low condo fee. Perfectly located near Winthrop’s beautiful beaches, scenic trails,

$399,000

2 beds1 bath1,092 sq ft

9 Atlantic St #2, Winthrop, MA 02152

Built-in cabinet • Private porches • Oversized pantry

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
WELCOME HOME to 14 Pleasant Park Road. .. BEEN IN THE SAME FAMILY FOR OVER 17 YEARS!!!. .. This BEAUTIFUL 4 BEDROOMS/ 1 FULL BATH 'GAMBREL COLONIAL STYLE HOME' is ready for new owners. .. 1st FLOOR offers WELCOMING FOYER w/ Hardwood Floors, CHERRY KITCHEN CABINETS w/ GRANITE COUNTERS & GRANITE ISLAND w/ Tiled Flooring & Recess Lighting, DINING ROOM w/ Hardwood Floors, LIVING ROOM w/ Hardwood Floors. .. 2nd FLOOR offers 3 Good sized BEDROOMS w/ Hardwood Floors, FULL TILED BATH w/ Shower Stall & Separate Soaking Tub w/ Tile Flooring, 2nd Floor LAUNDRY ROOM w/ Hardwood Floors. .. 3rd Floor offers BEDROOM w/ Walk-In Closet & BRAND NEW W/ W CARPET. .. FRESH NEW PAINT THRO

$724,900

4 beds1 bath1,964 sq ft

14 Pleasant Park Rd, Winthrop, MA 02152

Full tiled bath • Granite island • Welcoming foyer

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Move in ready, bright top floor 2 bedroom corner unit with lots of natural light! Freshly painted, beautiful sparkling hardwood floors throughout! White painted kitchen cabinets with newer appliances that include SS refrigerator, stove, dishwasher, and disposal. Two new built in wall a/c units. Newly rebuilt balcony with a partial Marsh water view. Governors Park is located in the small town of Winthrop, surrounded by the Atlantic Ocean and Boston Harbor with miles of beaches, marinas, yacht clubs and a 9 hole golf course! Additional amenities include all new schools, new athletic field and numerous renowned restaurants. Convenient Bus stop at the entrance of this complex takes you to t

$369,900

2 beds1 bath782 sq ft

800 Governors Dr #30, Winthrop, MA 02152

Newer appliances • Natural light • Corner unit

Property at 10 Somerset #201, Winthrop, MA 02152, 2 beds, 2 baths

$629,000

2 beds2 baths1,036 sq ft

10 Somerset #201, Winthrop, MA 02152

Property at 441 Winthrop St, Winthrop, MA 02152, 6 beds, 2 baths

$749,900

6 beds2 baths2,454 sq ft

441 Winthrop St, Winthrop, MA 02152

Property at 550 Pleasant St #506, Winthrop, MA 02152, 2 beds, 2 baths

$1,087,000

2 beds2 baths1,975 sq ft

550 Pleasant St #506, Winthrop, MA 02152

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

$1,075,000

5 beds2 baths2,212 sq ft

50-52 Wilshire St, Winthrop, MA 02152

Property at 35 Somerset Ave #6, Winthrop, MA 02152, 2 beds, 2 baths

$509,900

2 beds2 baths800 sq ft

35 Somerset Ave #6, 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

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ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
First time on the market in more than 50 years. Enjoy gorgeous water views from this extra spacious 2 family home located in sought after Highlands neighborhood. Unit 1 features 5 rooms, including a large L-shaped living room with fireplace, formal dining room with china cabinet, eat-in kitchen, 2 bedrooms, full bath and front and rear porches. Unit 2 features a big living room with fireplace, formal dining room, open to the eat-in-kitchen. There's 2 spacious bedrooms, a full tiled bath, front and rear porches, and a large, walk-up third floor finished space. Other features include a huge basement, beautiful hardwood floors, high ceilings, loads of natural light, nice yard and a big 4 car d

$1,125,000

4 beds2 baths2,908 sq ft

169 Grovers Ave, Winthrop, MA 02152

Huge basement • Formal dining room • Eat-in kitchen

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
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. Enjoy updated electric, beautiful updated countertops, top-of-the-line appliances, new plumbing fixtures, sun-filled rooms, wood restored fireplaces, front/back porches, fenced in yard and flexible layouts designed for comfort and value. Coastal breezes, nearby beaches, marinas, and shoreline pa

$1,280,000

6 beds3.5 baths3,093 sq ft

47 Bellevue Ave, Winthrop, MA 02152

Updated electric • In law guest suite • Two family home

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Coastal living in Winthrop! This 2 bed 1 bath condo offers many updates including NEW roof and siding (2025), NEW furnace for gas cooking (2024). Additional conveniences include, in-unit laundry 2023, and 1 off street parking spot! Located just steps away from the shoreline, beaches, local restaurants, and Winthrop's vibrant coastal community. Showings begin at open houses Saturday 12/6 11-1230 and Sunday 12/7 11-1230.

$389,900

2 beds1 bath667 sq ft

53 Trident Ave #103, Winthrop, MA 02152

New furnace • New siding • Off street parking

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ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Welcome to the Highlands, Winthrop’s most coveted neighborhood where modern design meets sweeping Boston views. This renovated home rises high on the hill with sunlit interiors, wide white oak floors, and timeless details throughout. The main level offers an open layout with a living room and fireplace, Thermador-Pro kitchen with island, beverage bar, and pantry, plus a dining area that opens to a skyline deck. A first-floor bedroom, full bath, and mudroom add versatility. Upstairs features three bedrooms, including a luxe primary suite with Juliet balcony, walk-in closet, and a spa bath with steam shower, soaking tub, heated floors, and double vanity. The lower level provides a compl

$1,699,900

5 beds4 baths3,866 sq ft

144 Quincy Ave, Winthrop, MA 02152

Renovated home • Modern design • Beverage bar

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Belle Mer is a newer built 16 unit condo association just on the outskirts of vibrant Winthrop Center, Nearby bountiful dining options, a best of North Shore boutique, coffee shops, fitness studios, book store, and unlimited conveniences. The unit is completely modernized with a timeless aesthetic. Seldom available, modern design 2 level floor plan with oversized windows, dramatic tall ceilings, exquisite appointments, 2 bedrooms, 2 bathrooms, charming window seats and ultimately desired PRIVATE front and back entries and assigned parking space 25. The association has curated wonderful professionally landscaped grounds creating a beautiful ambience nearby Boston Harbor. Hardwood floors, rec

$599,000

2 beds1.5 baths1,141 sq ft

142 Pleasant St #12, Winthrop, MA 02152

Chef ready kitchen • Oversized windows • $300 HOA

OPEN SAT, 10:30AM TO 12PM

ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Welcome to Unit 405 at The Somerset, a premier boutique condominium community in the heart of Winthrop. This well-designed 1-bedroom residence offers a spacious bedroom with a generous closet and an open-concept kitchen and living area that’s perfect for both entertaining and unwinding. The home features quartz countertops, stainless steel appliances, central A/C, and modern, stylish finishes throughout. Residents of The Somerset enjoy exceptional on-site amenities, including a fitness room, elevator, and a warm, inviting lounge ideal for remote work or casual gatherings. Located near sandy beaches, waterfront parks, and popular local dining—and offering convenient access to dow

$551,633

1 bed1 bath683 sq ft

10 Somerset #405, Winthrop, MA 02152

Warm inviting lounge • Waterfront parks • Generous closet

Property at 37 Trident Ave, Winthrop, MA 02152, 8 beds, 3 baths

$1,300,000

8 beds3 baths3,708 sq ft

37 Trident Ave, Winthrop, MA 02152

Property at 28 Pearl Ave #3, Winthrop, MA 02152, 3 beds, 1 bath

$545,000

3 beds1 bath1,280 sq ft

28 Pearl Ave #3, Winthrop, MA 02152

Property at 10 Beach Rd #1, Winthrop, MA 02152, 3 beds, 1 bath

$559,000

3 beds1 bath1,377 sq ft

10 Beach Rd #1, Winthrop, MA 02152

Property at 66 Lowell Rd, Winthrop, MA 02152, 6 beds, 2.5 baths

$1,150,000

6 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 600 Shirley St #3, Winthrop, MA 02152, 2 beds, 2 baths

$549,900

2 beds2 baths773 sq ft

600 Shirley St #3, Winthrop, MA 02152

Property at 600 Shirley St #1, Winthrop, MA 02152, 1 bed, 2 baths

$415,000

1 bed2 baths604 sq ft

600 Shirley St #1, Winthrop, MA 02152

Average home prices near Downtown Winthrop, MA

Cities

Neighborhoods

Belingham Square homes for sale
$499,999
East Boston homes for sale
$678,800
Beachmont homes for sale
$499,900
Maverick Square homes for sale
$659,000
West Revere homes for sale
$687,000
Orient Heights homes for sale
$734,361
Jeffries Point homes for sale
$700,000
South Boston Waterfront homes for sale
$1,499,000
Crescent Beach homes for sale
$535,000
Whinthrop Highlands homes for sale
$837,500

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)

$740,000

+18.9% YoY | Nov 2025

1 year
3 year
5 year

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

Location

Data

Nov 2025

Growth

% YoY

Downtown Winthrop, MA

$740,000

+18.9%

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