Downtown Winthrop, MA homes for sale & real estate

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OPEN SAT, 11AM TO 12:30PM

94 Lincoln St #2, Winthrop, MA 02152
94 Lincoln St #2, Winthrop, MA 02152
94 Lincoln St #2, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
This charming, move-in-ready 2-bed, 1-bath condo in a gorgeous brownstone building offers historic character and modern convenience just minutes from downtown Boston! Beautiful original hardwood floors and bay window add warmth and timeless appeal. Both bedrooms are generously sized and filled with natural light. The second bedroom has a walk-in closet. The spacious, eat-in kitchen features tile flooring, Corian countertops, and direct access to a peaceful, private deck. Two oversized hall closets provide excellent storage options. Additional storage and shared laundry are conveniently located in the basement. Enjoy Ingleside Park at your doorstep, or take a short stroll to Donovan's Beach,

$450,000

2 beds1 bath1,165 sq ft

94 Lincoln St #2, Winthrop, MA 02152

$300 HOA • Built 1900

OPEN SUN, 12:30PM TO 2PM

500 Governors Dr #9, Winthrop, MA 02152
500 Governors Dr #9, Winthrop, MA 02152
500 Governors Dr #9, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Welcome to 500 Governors Drive Unit 9, a spacious and well-maintained 3-bedroom, first-floor condo located in the beautiful coastal town of Winthrop. This unit features a bright and airy open-concept living and dining area, perfect for both relaxing and entertaining. Vinyl flooring runs throughout the entire home, offering a sleek, low-maintenance finish. Set within a well-managed association, residents enjoy peace of mind and a sense of community. Whether you're a first-time buyer, downsizer, or investor, this unit offers comfort, convenience, and value all in one.

$355,000

3 beds1 bath772 sq ft

500 Governors Dr #9, Winthrop, MA 02152

$466 HOA • Parking • Community pool

3 Buckthorn Ter #2, Winthrop, MA 02152
3 Buckthorn Ter #2, Winthrop, MA 02152
3 Buckthorn Ter #2, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Tucked away on a quiet street, this home boasts stately features and has been meticulously renovated. From the elegant newel post to the timeless kitchen details, nothing was overlooked. During the condo conversion, preserving the home's original integrity was a priority. The first floor offers 2 bedrooms, laundry, and a full bath with marble tile floors. The sunlit living room, complete with a fireplace, opens to the dining room and the first of two decks, offering ocean views. The second deck is covered, perfect for rainy days. The kitchen features high-end appliances and classic white cabinetry. Upstairs, find 2 more bedrooms, including a primary with a large walk-in closet and full bath

$760,000

4 beds2 baths1,870 sq ft

3 Buckthorn Ter #2, Winthrop, MA 02152

$334 HOA • Parking • Built 1900

OPEN TODAY, 4:30PM TO 6PM

10 Somerset Unit U201, Winthrop, MA 02152
10 Somerset Unit U201, Winthrop, MA 02152
10 Somerset Unit U201, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Welcome to Unit 201 at The Somerset—Winthrop’s premier boutique condo community where coastal charm meets modern design. This spacious 2-bed, 2-bath home features an open-concept layout with a large living/dining area perfect for entertaining or relaxing. A generous kitchen island anchors the space and faces the front of the building, inviting natural light and a welcoming flow. Enjoy quartz countertops, stainless steel appliances, central A/C, and stylish finishes throughout. The Somerset offers garage parking, a fitness room, elevator access, and a cozy resident lounge ideal for remote work or casual connection. Close proximity to sandy beaches, waterfront parks, and local res

$629,000

2 beds2 baths1,036 sq ft

10 Somerset Unit U201, Winthrop, MA 02152

$466 HOA • Built 2022 • Listed 6 days

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37-39 Hutchinson St, Winthrop, MA 02152
37-39 Hutchinson St, Winthrop, MA 02152
37-39 Hutchinson St, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Endless Potential in Prime Seaside Location – 02152 Welcome to this oversized two-family home located in the highly desirable seaside community of Winthrop, 02152. Perfectly situated on a generous lot, this property offers a rare opportunity for investors, multi-generational living, or owner-occupants looking to customize and create value. Each unit features spacious layouts with room to grow, and the home includes a full unfinished basement—ideal for storage or future expansion. Enjoy the convenience of off-street parking and a private backyard, perfect for outdoor entertaining or quiet relaxation. With its prime location near the ocean, beaches, and all that Winthrop has to of

$899,000

5 beds2 baths2,958 sq ft

37-39 Hutchinson St, Winthrop, MA 02152

5,000 sq ft lot • 3 parking spots • Built 1920

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

$899,000

4 beds3.5 baths2,350 sq ft

136 Pauline St, Winthrop, MA 02152

Property at 123 Buchanan St, Winthrop, MA 02152, 4 beds, 1.5 baths

$588,888

4 beds1.5 baths1,785 sq ft

123 Buchanan St, Winthrop, MA 02152

Property at 115 Almont St, Winthrop, MA 02152, 5 beds, 3 baths

$995,500

5 beds3 baths3,272 sq ft

115 Almont St, Winthrop, MA 02152

Property at 56 Main St, Winthrop, MA 02152, 4 beds, 2 baths

$799,900

4 beds2 baths2,103 sq ft

56 Main St, Winthrop, MA 02152

Property at 19 Banks St, Winthrop, MA 02152, 3 beds, 1 bath

$735,000

3 beds1 bath1,269 sq ft

19 Banks St, Winthrop, MA 02152

Property at 60 Waldemar Ave, Winthrop, MA 02152, 3 beds, 1 bath

$729,000

3 beds1 bath1,548 sq ft

60 Waldemar Ave, Winthrop, MA 02152

Property at 143 Morton St, Winthrop, MA 02152, 4 beds, 2.5 baths

$799,900

4 beds2.5 baths2,447 sq ft

143 Morton St, Winthrop, MA 02152

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

$560,000

2 beds2 baths823 sq ft

35 Somerset Ave #6, Winthrop, MA 02152

Property at 136 Locust Way, Winthrop, MA 02152, 3 beds, 1 bath

$624,900

3 beds1 bath1,878 sq ft

136 Locust Way, Winthrop, MA 02152

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

$1,100,000

4 beds2 baths2,366 sq ft

80 Shirley St, 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

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

$649,900

3 beds2 baths1,252 sq ft

80 Shirley St #2, Winthrop, MA 02152

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Nearby homes that match your criteria

4 Circuit, Winthrop, MA 02152
4 Circuit, Winthrop, MA 02152
4 Circuit, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Prime corner lot in one of Winthrop’s most desirable neighborhoods! This home has great bones and is ready for new owners to make it their own. With an ideal layout, the second floor offers the perfect space for a primary suite with walk-in closet and full bath. The first floor features a spacious living room, with the opportunity to open up the kitchen and dining area for a large island and modern flow. A side entry leads into a generous mudroom with potential for custom storage. The backyard is perfect for a patio, outdoor kitchen, and entertaining. The garage could be connected to the home with a breezeway. Once renovated, this home could be worth $1.2M+. The price reflects the upd

$735,000

4 beds1 bath2,327 sq ft

4 Circuit, Winthrop, MA 02152

4,100 sq ft lot • Garage • Built 1920

OPEN TODAY, 4:30PM TO 6PM

100 Cottage Ave, Winthrop, MA 02152
100 Cottage Ave, Winthrop, MA 02152
100 Cottage Ave, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Ideally located just steps from the Winthrop Yacht Club, The Landing, local restaurants, and both Winthrop and Yirrell Beach, this spacious single-family home offers stunning water views and a clear line to Boston’s skyline. The first level features a unique and expansive layout with a formal living and dining room anchored by a double-sided fireplace wrapped in lava-rock, plus two additional rooms perfect for a family room, guest room, or home office. The updated eat-in kitchen includes a convenient half bath with in-unit laundry and plenty of cabinet space with a Wolf Cooktop, Miele dishwasher and newer range. The upstairs offers three spacious bedrooms including an expansive oversi

$879,900

3 beds2.5 baths2,293 sq ft

100 Cottage Ave, Winthrop, MA 02152

4,570 sq ft lot • Garage • Built 1915

72 Sewall Ave, Winthrop, MA 02152
72 Sewall Ave, Winthrop, MA 02152
72 Sewall Ave, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Highly desirable location this home is only 16 years old built over its original foundation. this 4-bed, 3.5-bath home spans three levels in Winthrop’s Highlands. The first floor offers an open layout ideal for entertaining, with a spacious kitchen featuring white cabinets and updated countertops flowing into the living and dining rooms. French doors lead to a deck and patio overlooking a large, fenced in backyard. The main suite opens to a private side deck and features a primary bath. Enjoy central air, second-floor laundry, a large basement for storage, a newer furnace and water heater (2022). The top floor offers a ocean views, and there's a hidden beach at the end of the street.

$1,265,000

4 beds3.5 baths2,214 sq ft

72 Sewall Ave, Winthrop, MA 02152

8,487 sq ft lot • Garage • Built 2009

3D WALKTHROUGH

500 Shirley St, Winthrop, MA 02152
500 Shirley St, Winthrop, MA 02152
500 Shirley St, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Located just 3.5 miles from the game-changing Suffolk Downs redevelopment, this fantastic two-family home offers incredible long-term upside in one of the fastest-growing areas north of Boston. The project promises millions of square feet of new housing, retail, parks, and life science space—adding immense value & convenience to the surrounding neighborhoods. Just steps from the beach, this income-generating property has been a strong rental performer—ideal for investors or owner-occupants. In the last 9 years, the home has seen MAJOR updates including a 200-amp electrical service upgrade, new front deck and revamped rear deck, a full renovation of Unit 2 (kitchen, floorin

$829,900

4 beds2 baths2,088 sq ft

500 Shirley St, Winthrop, MA 02152

4,150 sq ft lot • Garage • Built 1900

OPEN FRI, 6PM TO 7:30PM

94 Circuit Rd, Winthrop, MA 02152
94 Circuit Rd, Winthrop, MA 02152
94 Circuit Rd, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Step inside this farmhouse-style gem and feel right at home. The first floor offers a spacious layout featuring a cozy eat-in kitchen with stainless steel appliances, a formal dining room, and a full bath with direct access to the backyard, perfect for easy pool days. Hardwood floors flow throughout, adding warmth and charm to every room. Character shines at every turn with thoughtful details that make everyday living feel extra special. Upstairs, you’ll find three comfortable bedrooms and a second full bath. The primary bedroom features two closets, offering plenty of space to create a private retreat. Outside is where the magic happens, your own private pool oasis awaits. The pool h

$899,000

3 beds2 baths1,831 sq ft

94 Circuit Rd, Winthrop, MA 02152

6,500 sq ft lot • Garage • Pool

OPEN TODAY, 4:30PM TO 6PM

10 Somerset #408, Winthrop, MA 02152
10 Somerset #408, Winthrop, MA 02152
10 Somerset #408, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Step into a spacious 1-bedroom + den home at The Somerset, Winthrop’s newest boutique condo community blending coastal charm with modern comfort. This thoughtfully designed layout offers an open-concept living space, a versatile den ideal for a home office or guest room, and a walk-in closet in the bedroom. Enjoy upscale finishes throughout—quartz countertops, stainless steel appliances, central A/C, and sleek modern details. This elevator building features a fitness room, resident lounge, and most units include garage parking. Select homes also offer private decks for your own outdoor escape. Located in the heart of Winthrop, just minutes from beaches, neighborhood shops, and

$539,900

1 bed1 bath767 sq ft

10 Somerset #408, Winthrop, MA 02152

$427 HOA • Built 2022 • Listed 14 days

Property at 44 Cliff #3, Winthrop, MA 02152, 3 beds, 2 baths

$679,000

3 beds2 baths1,849 sq ft

44 Cliff #3, Winthrop, MA 02152

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

$679,000

2 beds2 baths971 sq ft

148 Winthrop Shore Dr #5, Winthrop, MA 02152

Property at 45 Highland Ave, Winthrop, MA 02152, 10 beds, 4 baths

$1,400,000

10 beds4 baths4,671 sq ft

45 Highland Ave, Winthrop, MA 02152

Property at 68-70 Floyd St, Winthrop, MA 02152, 4 beds, 3.5 baths

$999,900

4 beds3.5 baths3,432 sq ft

68-70 Floyd St, 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

Property at 247 Washington Ave #9, Winthrop, MA 02152, 2 beds, 2 baths

$520,000

2 beds2 baths1,116 sq ft

247 Washington Ave #9, Winthrop, MA 02152

Property at 10 Somerset #405, Winthrop, MA 02152, 1 bed, 1 bath

$551,633

1 bed1 bath683 sq ft

10 Somerset #405, Winthrop, MA 02152

Property at 230 Crescent Ave, Revere, MA 02151, 5 beds, 2 baths

$899,000

5 beds2 baths2,154 sq ft

230 Crescent Ave, Revere, MA 02151

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 35 Somerset Unit 5A, Winthrop, MA 02152, 2 beds, 2 baths

$599,000

2 beds2 baths969 sq ft

35 Somerset Unit 5A, Winthrop, MA 02152

Property at 162 Shirley, Winthrop, MA 02152, 3 beds, 2 baths

$699,000

3 beds2 baths1,413 sq ft

162 Shirley, Winthrop, MA 02152

Property at 25 Pearl Ave, Revere, MA 02151, 3 beds, 1 bath

$579,000

3 beds1 bath1,052 sq ft

25 Pearl Ave, Revere, MA 02151

Property at 600 Shirley St #16, Winthrop, MA 02152, 2 beds, 2 baths

$525,000

2 beds2 baths865 sq ft

600 Shirley St #16, 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

Oak Island homes for sale
$569,850
East Boston homes for sale
$699,000
Beachmont homes for sale
$799,900
Maverick Square homes for sale
$699,000
West Revere homes for sale
$499,000
Orient Heights homes for sale
$569,450
Jeffries Point homes for sale
$802,000
Crescent Beach homes for sale
$659,000
D Street-West Broadway homes for sale
$1,499,500
Whinthrop Highlands homes for sale
$912,450

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)

$705,000

-0.7% YoY | Jun 2025

1 year
3 year
5 year

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

Location

Data

Jun 2025

Growth

% YoY

Downtown Winthrop, MA

$705,000

-0.7%

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