Downtown Winthrop, MA homes for sale & real estate

12 homes

Sort:

Recommended

OPEN SAT, 11AM TO 12PM

10 Somerset #403, Winthrop, MA 02152
10 Somerset #403, Winthrop, MA 02152
10 Somerset #403, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Welcome to The Somerset—Winthrop’s newest boutique condo development! This collection of 29 thoughtfully designed homes offers studios, 1-bed, 1+ bed, and 2-bedroom layouts with quality finishes and a coastal vibe. Enjoy open-concept living, stainless steel appliances, quartz countertops, central A/C, and stylish modern touches. Most units include garage parking, and select homes feature private decks. The elevator building also offers a fitness room and a welcoming common area—perfect for relaxing or enjoying a coffee. Ideally located in the heart of Winthrop, just a short distance from sandy beaches, local shops, and an easy commute to downtown Boston.

$383,000

1 bed1 bath475 sq ft

10 Somerset #403, Winthrop, MA 02152

$253 HOA

OPEN SAT, 11AM TO 1PM

509 Pleasant St, Winthrop, MA 02152
509 Pleasant St, Winthrop, MA 02152
509 Pleasant St, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Welcome to 509 Pleasant, where coastal charm meets modern chic. This 3 bed/2 bath cottage style home is located in the ideal spot for both beach and city lovers. It features a smart system including Nest thermostat and Ring doorbell, a newer roof, recessed lighting, two fireplaces, a walk-in closet, in-built cabinets, a fully finished basement, a bonus room ideal for a playroom or gym, and an updated gorgeous wet bar and seating area! There is a large mudroom upon entry of the home, and ample room for storage. The sizeable patio is ideal for additional parking or to entertain your friends and family this summer. Located across the street from a marina, around the corner from parks and rest

$829,999

3 beds2 baths2,000 sq ft

509 Pleasant St, Winthrop, MA 02152

4,370 sq ft lot

OPEN SUN, 12PM TO 2PM3D WALKTHROUGH

80 Shirley St, Winthrop, MA 02152
80 Shirley St, Winthrop, MA 02152
80 Shirley St, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Coastal vibes flow through this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. Both units boast modern open floor plans. Actual high end finishes throughout for an obvious upscale vibe. Huge kitchens and natural light throughout. Some of the sunniest units you will see. Bathrooms like spas. High ceilings and great flowing layouts that make sense. The convenience of living in East Boston and the blue line nearby, without the congestion and lack of parking. Huge yard and driveway. Brand new heating systems, central A/C, upgr

$1,100,000

4 beds2 baths2,366 sq ft

80 Shirley St, Winthrop, MA 02152

5,500 sq ft lot

OPEN SUN, 12PM TO 2PM

80 Shirley St #1, Winthrop, MA 02152
80 Shirley St #1, Winthrop, MA 02152
80 Shirley St #1, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Coastal vibes flow throughout this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. The unit boasts a modern open floor plan. Actual high end finishes throughout for an obvious upscale vibe. Huge kitchen and natural light throughout. One of the sunniest units that you will see. High ceilings and a great flowing layout that makes sense. The convenience of living in East Boston and the blue line nearby, without the congestion and lack of parking. Huge yard and driveway. Brand new heating systems, central A/C, upgraded plumbing

$449,900

1 bed1 bath836 sq ft

80 Shirley St #1, Winthrop, MA 02152

5,500 sq ft lot • $150 HOA

OPEN SUN, 12PM TO 2PM

80 Shirley St #2, Winthrop, MA 02152
80 Shirley St #2, Winthrop, MA 02152
80 Shirley St #2, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Coastal vibes flow throughout this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. The unit boasts a modern open floor plan. Actual high end finishes throughout for an obvious upscale vibe. Huge kitchen and natural light throughout. Spa like bathrooms. One of the sunniest units that you will see. High ceilings and a great flowing layout that makes sense. The convenience of living in East Boston and the blue line nearby, without the congestion and lack of parking. Huge yard and driveway. Brand new heating systems, central A/

$649,900

3 beds2 baths1,252 sq ft

80 Shirley St #2, Winthrop, MA 02152

5,500 sq ft lot • $250 HOA

Property at 96-98 Woodside Ave, Winthrop, MA 02152, 4 beds, 2 baths

$899,000

4 beds2 baths2,124 sq ft

96-98 Woodside Ave, Winthrop, MA 02152

Property at 175 Pleasant St, Winthrop, MA 02152, 4 beds, 3 baths

$989,000

4 beds3 baths4,101 sq ft

175 Pleasant 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 86 Chester Ave, Winthrop, MA 02152, 6 beds, 2.5 baths

$1,099,000

6 beds2.5 baths2,692 sq ft

86 Chester Ave, Winthrop, MA 02152

Property at 114 Bowdoin St #114, Winthrop, MA 02152, 4 beds, 2 baths

$659,000

4 beds2 baths2,054 sq ft

114 Bowdoin St #114, Winthrop, MA 02152

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

$570,000

2 beds2 baths823 sq ft

35 Somerset Ave #6, Winthrop, MA 02152

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

$799,000

4 beds2 baths1,870 sq ft

3 Buckthorn #2, Winthrop, MA 02152

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

Within 1 mile

OPEN SAT, 12PM TO 1:30PM

92 Winthrop Shore Dr #2, Winthrop, MA 02152
92 Winthrop Shore Dr #2, Winthrop, MA 02152
92 Winthrop Shore Dr #2, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
* * * OPEN HOUSE Sat & Sun 12-1:30pm * * * Experience the serenity of coastal living in this inviting oceanside condo. Awaken each morning to breathtaking sunrises and the soothing sound of waves. This bright and airy home features gleaming hardwood floors throughout, encompassing a well-appointed kitchen, open-concept living and dining areas, three comfortable bedrooms, and a full bathroom. Enjoy the ocean breeze from your front windows, and unwind on the rear deck as the sun sets over the treetops. With deeded off-street parking and additional public parking nearby, convenience is at your doorstep. Located within walking distance to the local golf course & town center shop

$450,000

3 beds1 bath1,245 sq ft

92 Winthrop Shore Dr #2, Winthrop, MA 02152

$375 HOA

19 Orlando Ave, Winthrop, MA 02152
19 Orlando Ave, Winthrop, MA 02152
19 Orlando Ave, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Welcome to this timeless 8-room Whittemore Colonial, perfectly situated in the heart of the highly sought-after Cottage Park neighborhood. This spacious home offers 4 bedrooms, 2.5 baths, and the charm and character of classic architecture paired with modern updates. The main level features a gracious LR with a cozy fireplace, a formal DR highlighted by a stunning leaded glass built-in china cabinet, and an updated kitchen with SS appliances and island. A convenient 1/2 bath completes the first floor. Upstairs, you'll find a generously sized primary BDRM along with two additional BDRMS and a full bath. The 3rd floor offers a 4th BDRM and an additional room that could be easily finished. Low

$950,000

4 beds2.5 baths2,470 sq ft

19 Orlando Ave, Winthrop, MA 02152

6,185 sq ft lot

OPEN TODAY, 5:30PM TO 7PM

162 Shirley, Winthrop, MA 02152
162 Shirley, Winthrop, MA 02152
162 Shirley, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Don’t miss this rare opportunity to own a well-priced single-family home in the heart of Winthrop by the Sea, under a 5-minute walk to both the beach and Winthrop Middle/High School. This charming home features 3 bedrooms and 2 full baths. The second floor also offers room for expansion to add a 4th bedroom, sellers are including the architectural plans. The main level boasts new appliances, granite countertops, and newer central air and heating (installed within the past 5 years). Enjoy outdoor living with a quaint backyard patio and a large enclosed front lawn with an enclosed white fence — ideal for entertaining, pets, or gardening. Additional features include 4 off-street ta

$729,000

3 beds2 baths1,413 sq ft

162 Shirley, Winthrop, MA 02152

4,520 sq ft lot

OPEN SAT, 11:30AM TO 1PM

30 Crystal Cove Ave #2, Winthrop, MA 02152
30 Crystal Cove Ave #2, Winthrop, MA 02152
30 Crystal Cove Ave #2, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Nestled in Winthrop’s sought-after Crystal Cove neighborhood, this beautifully maintained two-level condo perfectly combines timeless character with stylish comfort. A grand staircase serves as the home’s architectural showpiece, adding elegance and a sense of grandeur. The sun-filled unit features an updated kitchen, two bedrooms and renovated bathrooms offering modern finishes and functionality. The oversized living room sparkles with views of the marina and Boston skyline. Upstairs is a true retreat bedroom featuring skylights, gleaming floors and another bathroom. Throughout the home, original hardwood floors lend warmth and classic appeal. Step outside to your private deck

$524,900

2 beds2 baths1,219 sq ft

30 Crystal Cove Ave #2, Winthrop, MA 02152

$275 HOA

25 Pearl Ave, Revere, MA 02151
25 Pearl Ave, Revere, MA 02151
25 Pearl Ave, Revere, MA 02151
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
We are pleased to present a compelling investment opportunity at 25 Pearl Avenue in Revere, Massachusetts. This property offers significant potential for developers and investors seeking to capitalize on the growing demand in the Revere market. Presenting an exceptional investment or redevelopment opportunity just steps from Short Beach in Revere’s coveted Beachmont neighborhood. This single-family parcel sits on a 6,534 sq ft lot (0.15 acres) in the RB zoning district. The lot’s generous dimensions and prime location—mere minutes to Logan Airport, downtown Boston, and Revere Beach—make it an ideal candidate for a custom single-family build, two-family redevelopment,

$615,000

3 beds1 bath1,052 sq ft

25 Pearl Ave, Revere, MA 02151

6,499 sq ft lot • Community pool

27 Crystal Cove Ave, Winthrop, MA 02152
27 Crystal Cove Ave, Winthrop, MA 02152
27 Crystal Cove Ave, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Nestled in the heart of Winthrop Head, this 4bed, 2bath Colonial blends timeless charm with a prime location just moments from multiple beaches and the scenic Winthrop Golf Club. Enjoy sweeping ocean views from the spacious front porch—an ideal spot for coffee or evening sunsets. Enter inside to a welcoming foyer featuring a bay window, fireplace & gleaming HW floors that flow seamlessly into a formal dining room perfect for entertaining. The kitchen includes a butler's pantry, offering ample storage and prep space. Upstairs, you’ll find four bedrooms and a full bath, w/ 2 addt'l bonus rooms on the third floor—perfect for a home office or guest space. The finished ba

$865,000

4 beds2 baths2,412 sq ft

27 Crystal Cove Ave, Winthrop, MA 02152

4,174 sq ft lot • Garage

Property at 265 Washington Ave Unit 2A, Winthrop, MA 02152, 1 bed, 1 bath

$299,500

1 bed1 bath400 sq ft

265 Washington Ave Unit 2A, Winthrop, MA 02152

Property at 105 Circuit Rd, Winthrop, MA 02152, 5 beds, 2.5 baths

$879,900

5 beds2.5 baths2,065 sq ft

105 Circuit Rd, Winthrop, MA 02152

Property at 10 Somerset #401, Winthrop, MA 02152, 1 bed, 1 bath

$555,000

1 bed1 bath684 sq ft

10 Somerset #401, Winthrop, MA 02152

Property at 5 Waveway Ave, Winthrop, MA 02152, 6 beds, 6 baths

$1,780,000

6 beds6 baths4,122 sq ft

5 Waveway 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 23 Trident Ave Unit 3, Winthrop, MA 02152, 3 beds, 1 bath

$535,000

3 beds1 bath1,353 sq ft

23 Trident Ave Unit 3, Winthrop, MA 02152

Property at 23 Trident Ave Unit 2, Winthrop, MA 02152, 3 beds, 1 bath

$520,000

3 beds1 bath1,369 sq ft

23 Trident Ave Unit 2, Winthrop, MA 02152

Property at 226 Court Rd #226, Winthrop, MA 02152, 4 beds, 2 baths

$735,000

4 beds2 baths1,986 sq ft

226 Court Rd #226, Winthrop, MA 02152

Property at 18 Leverett Ave Unit 9B, Boston, MA 02128, 2 beds, 1.5 baths

$579,000

2 beds1.5 baths972 sq ft

18 Leverett Ave Unit 9B, Boston, MA 02128

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

$549,000

2 beds2 baths865 sq ft

600 Shirley St #16, Winthrop, MA 02152

Property at 76 Pearl Ave, Revere, MA 02151, 4 beds, 3 baths

$649,986

4 beds3 baths1,507 sq ft

76 Pearl Ave, Revere, MA 02151

Property at 121 Circuit Rd, Winthrop, MA 02152, 5 beds, 3 baths

$1,200,000

5 beds3 baths3,100 sq ft

121 Circuit Rd, Winthrop, MA 02152

Property at 10 Somerset #206, Winthrop, MA 02152, 2 beds, 1.5 baths

$639,815

2 beds1.5 baths985 sq ft

10 Somerset #206, Winthrop, MA 02152

Property at 12 Sewall Ave #3, Winthrop, MA 02152, 1 bed, 1 bath

$474,900

1 bed1 bath742 sq ft

12 Sewall Ave #3, Winthrop, MA 02152

Average home prices near Downtown Winthrop, MA

Cities

Neighborhoods

Logan Airport / Jeffries Point homes for sale
$799,000
Downtown Revere homes for sale
$999,900
East Boston homes for sale
$699,000
Beachmont homes for sale
$814,000
Maverick Square homes for sale
$699,000
West Revere homes for sale
$612,450
Orient Heights homes for sale
$579,000
Jeffries Point homes for sale
$728,000
Crescent Beach homes for sale
$644,950
Whinthrop Highlands homes for sale
$760,200

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)

$655,000

-12.1% YoY | Apr 2025

1 year
3 year
5 year

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

Location

Data

Apr 2025

Growth

% YoY

Downtown Winthrop, MA

$655,000

-12.1%

See more Downtown Winthrop, MA market insights

More to explore in Downtown Winthrop, MA

How to buy a house in Downtown Winthrop, MA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Massachusetts

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Become a Lender Partner

Subsidiaries

Rent.

ApartmentGuide

Bay Equity Home Loans

Title Forward

Countries

United States

Canada

Updated January 2023: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, TITLE FORWARD, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.