Vintage homes for sale & real estate in 02152, MA

48 homes + 1 early access

Sort:

Recommended

OPEN TODAY, 11AM TO 12:30PMFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 02152, MA:
The perfect blend of comfort, convenience, and affordability! Whether you’re a first-time homebuyer, looking to downsize, or searching for an alternative to condo living, this charming 4-bedroom home offers the space you need with the low-maintenance lifestyle you want all just one block from the beach. The main level features a comfortable bedroom and full bathroom with a convenient walk-in shower, making one-floor living a great option for a variety of needs. You’ll also find main-level laundry, an eat-in kitchen, a convenient mudroom off the entryway to store shoes and umbrellas, and split-unit heating and cooling for year-round comfort. Upstairs are three additional generous

$710,000

4 beds2 baths1,193 sq ft

542 Shirley St, Winthrop, MA 02152

Eat in kitchen • Main level laundry • Great closet space

OPEN TODAY, 11AM TO 1PM

ABOUT THIS HOME
Vintage Home for sale in 02152, MA:
This meticulously maintained 3-bedroom, 2 full bath home sits on a private corner lot in Winthrop's coveted Point Shirley neighborhood. The main level offers two distinct living areas, a fireplace, eat-in kitchen, a full bathroom and a bedroom or home office. Featuring two spacious bedrooms, the upper level also provides a generous walk-in closet, a second full bath and glimpses of the ocean and Boston Harbor from three windows. The walk-out lower level includes a spacious family room or guest area with two closets, plus utility, storage, laundry area and extra space for a future third bath. Move-in ready with a brand-new retaining wall and expanded driveway. Short distance from Yirrell Bea

$739,000

3 beds2 baths1,428 sq ft

8 Siren St, Winthrop, MA 02152

Walk-in closet • Private corner lot • Expanded driveway

OPEN SUN, 12PM TO 1:30PM

ABOUT THIS HOME
Vintage Home for sale in 02152, MA:
Open House This Weekend! Sunday 8/30/26 12:00-1:30pm A fantastic value for this home. Its an opportunity to make it your own. Spacious and beautifully updated, 6-bedroom, 2.5-bath home with the perfect blend of classic character & modern efficiency, all located in the wonderful seaside community of Winthrop by the Sea. Featuring gleaming hardwood floors throughout, newer windows 2 fireplaces giving warmth & charm to the living spaces. Extensive updates include all new mechanical systems including elec. wiring, FWA furnace, cent A/C, on-demand HW, mini-split heat pump/AC units, plumbing lighting, all providing peace of mind for years to come. Generous space, new paint & p

$998,900

6 beds2.5 baths3,263 sq ft

217 Pleasant St, Winthrop, MA 02152

Fwa furnace • 2 fireplaces • Cent a/c

OPEN TODAY, 2PM TO 4PM

ABOUT THIS HOME
Vintage Home for sale in 02152, MA:
A rare opportunity to own a beachside home in this highly desirable coastal neighborhood! This 3 bdrm, 1 3/4 bath Beach Bungalow is the perfect condo alternative! The Main BDRM & FR have been fully renovated offering a Classic timeless design! New doors, recessed lighting, smooth ceilings, custom trim & crown molding, walk in closet, built in seating/cabinet, custom made covers for radiators, fireplace w/ wood mantel & shiplap on the walls! Entertain friends, grill, relax on your NEWLY BUILT expansive rear deck w/ steps to the beach! Embrace all that living in beach community offers~ Catch a Sunrise, Swimming, Surfing, Sunbathe or Boating! Eat in kitchen w/ water views off

$649,000

3 beds1.5 baths1,200 sq ft

84 Tafts Ave, Winthrop, MA 02152

Fully renovated • Water views • Cedar closets

ABOUT THIS HOME
Vintage Home for sale in 02152, MA:
Oversized one bedroom condo in Winthrop's historic Playmakers building, just minutes from Winthrop Center. This bright, modern unit features an open concept living space with cathedral ceilings and hardwood floors throughout. The kitchen offers a large island, stone countertops, stainless steel appliances, a gas stove, and a wine chiller. A spacious bedroom and office sit on the primary floor, with ladders leading up to two additional multi-use loft spaces. Stacked washer and dryer in unit. One off-street parking spot. Steps to public transportation, parks, tennis courts, and less than a half mile to the beach.

$539,000

1 bed1 bath1,368 sq ft

60 Hermon St #3, Winthrop, MA 02152

Stone countertops • Cathedral ceilings • Large island

Property at 2 Edgar Ter #3, Winthrop, MA 02152, 2 beds, 1 bath

$479,900

2 beds1 bath1,056 sq ft

2 Edgar Ter #3, Winthrop, MA 02152

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

$865,000

2 beds2.5 baths1,806 sq ft

1001 Shirley St #2, Winthrop, MA 02152

Property at 26 George St, Winthrop, MA 02152, 4 beds, 4 baths

$799,000

4 beds4 baths2,910 sq ft

26 George St, Winthrop, MA 02152

Property at 43 Dolphin Ave, Winthrop, MA 02152, 5 beds, 2.5 baths

$829,900

5 beds2.5 baths2,437 sq ft

43 Dolphin Ave, Winthrop, MA 02152

Property at 12 Sewall Ave Unit 2B, Winthrop, MA 02152, 2 beds, 2 baths

$555,000

2 beds2 baths874 sq ft

12 Sewall Ave Unit 2B, Winthrop, MA 02152

Property at 546 Shirley St, Winthrop, MA 02152, 4 beds, 2.5 baths

$765,000

4 beds2.5 baths1,933 sq ft

546 Shirley St, Winthrop, MA 02152

Property at 175 Shirley St #5, Winthrop, MA 02152, 2 beds, 1 bath

$374,999

2 beds1 bath649 sq ft

175 Shirley St #5, Winthrop, MA 02152

Property at 69 Summit Ave #1, Winthrop, MA 02152, 1 bed, 1 bath

$369,000

1 bed1 bath1,000 sq ft

69 Summit Ave #1, Winthrop, MA 02152

Property at 189 Shirley St #1, Winthrop, MA 02152, 3 beds, 2.5 baths

$758,000

3 beds2.5 baths1,800 sq ft

189 Shirley St #1, Winthrop, MA 02152

Property at 283 Revere St #2, Winthrop, MA 02152, 3 beds, 1 bath

$549,000

3 beds1 bath1,788 sq ft

283 Revere St #2, Winthrop, MA 02152

Property at 92 Lincoln St #2, Winthrop, MA 02152, 2 beds, 1 bath

$459,900

2 beds1 bath1,153 sq ft

92 Lincoln St #2, Winthrop, MA 02152

Property at 52 Pebble Ave, Winthrop, MA 02152, 4 beds, 1.5 baths

$715,000

4 beds1.5 baths1,586 sq ft

52 Pebble Ave, Winthrop, MA 02152

Property at 21 Hutchinson St #2, Winthrop, MA 02152, 2 beds, 2.5 baths

$629,000

2 beds2.5 baths1,463 sq ft

21 Hutchinson St #2, Winthrop, MA 02152

Property at 229 Washington Ave Unit 3A, Winthrop, MA 02152, 1 bed, 1 bath

$219,999

1 bed1 bath350 sq ft

229 Washington Ave Unit 3A, Winthrop, MA 02152

Property at 174 Bartlett Rd, Winthrop, MA 02152, 5 beds, 5.5 baths

$2,380,000

5 beds5.5 baths6,224 sq ft

174 Bartlett Rd, Winthrop, MA 02152

Property at 34R Underhill St #3, Winthrop, MA 02152, 2 beds, 2 baths

$449,900

2 beds2 baths879 sq ft

34R Underhill St #3, Winthrop, MA 02152

Property at 16 Billows St Unit B, Winthrop, MA 02152, 2 beds, 1 bath

$549,000

2 beds1 bath928 sq ft

16 Billows St Unit B, Winthrop, MA 02152

Property at 37 Loring Rd, Winthrop, MA 02152, 3 beds, 2.5 baths

$869,900

3 beds2.5 baths2,125 sq ft

37 Loring Rd, Winthrop, MA 02152

Property at 189 Shirley #2, Winthrop, MA 02152, 3 beds, 2.5 baths

$675,000

3 beds2.5 baths1,510 sq ft

189 Shirley #2, Winthrop, MA 02152

Property at 89R Upland, Winthrop, MA 02152, 4 beds, 2.5 baths

$1,399,000

4 beds2.5 baths2,475 sq ft

89R Upland, Winthrop, MA 02152

Property at 153 Locust St, Winthrop, MA 02152, 4 beds, 2 baths

$715,000

4 beds2 baths1,963 sq ft

153 Locust St, Winthrop, MA 02152

Property at 120 Hermon St, Winthrop, MA 02152, 6 beds, 2 baths

$780,000

6 beds2 baths2,000 sq ft

120 Hermon St, Winthrop, MA 02152

Property at 27 Billows St, Winthrop, MA 02152, 3 beds, 2.5 baths

$840,000

3 beds2.5 baths1,837 sq ft

27 Billows St, Winthrop, MA 02152

Property at 118 Sunnyside Ave, Winthrop, MA 02152, 4 beds, 2 baths

$895,000

4 beds2 baths1,755 sq ft

118 Sunnyside Ave, Winthrop, MA 02152

Property at 496 Winthrop St, Winthrop, MA 02152, 3 beds, 2 baths

$650,000

3 beds2 baths800 sq ft

496 Winthrop St, Winthrop, MA 02152

Property at 70 Edgehill Rd, Winthrop, MA 02152, 4 beds, 3.5 baths

$1,199,999

4 beds3.5 baths1,904 sq ft

70 Edgehill Rd, Winthrop, MA 02152

Property at 53 Trident Ave #301, Winthrop, MA 02152, 2 beds, 1 bath

$385,000

2 beds1 bath677 sq ft

53 Trident Ave #301, Winthrop, MA 02152

Property at 52 Trident Ave #52, Winthrop, MA 02152, 2 beds, 1 bath

$499,000

2 beds1 bath1,006 sq ft

52 Trident Ave #52, Winthrop, MA 02152

Property at 32 Irwin St, Winthrop, MA 02152, 6 beds, 4 baths

$1,100,000

6 beds4 baths2,949 sq ft

32 Irwin St, Winthrop, MA 02152

Property at 600 Shirley St #11, Winthrop, MA 02152, 1 bed, 1 bath

$299,999

1 bed1 bath351 sq ft

600 Shirley St #11, Winthrop, MA 02152

Property at 47 Highland Ave, Winthrop, MA 02152, 3 beds, 1.5 baths

$599,000

3 beds1.5 baths1,728 sq ft

47 Highland Ave, Winthrop, MA 02152

Property at 43 Loring Rd, Winthrop, MA 02152, 3 beds, 1.5 baths

$939,900

3 beds1.5 baths2,371 sq ft

43 Loring Rd, Winthrop, MA 02152

Property at 600 Shirley St #7, Winthrop, MA 02152, 1 bed, 1.5 baths

$485,000

1 bed1.5 baths591 sq ft

600 Shirley St #7, Winthrop, MA 02152

Property at 50 Main St, Winthrop, MA 02152, 6 beds, 2 baths

$799,986

6 beds2 baths2,560 sq ft

50 Main St, Winthrop, MA 02152

Property at 100 Sargent St, Winthrop, MA 02152, 6 beds, 5.5 baths

$1,450,000

6 beds5.5 baths5,278 sq ft

100 Sargent St, Winthrop, MA 02152

Property at 66 Sunnyside Ave, Winthrop, MA 02152, 5 beds, 2 baths

$999,888

5 beds2 baths2,635 sq ft

66 Sunnyside Ave, Winthrop, MA 02152

Viewing page 1 of 2

Vintage Homes for Sale in 02152

There are currently 49 vintage homes for sale in 02152 at a median listing price of $682K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 02152 stay on the market for 49 days and receive 1 offers. This map is refreshed with the newest listings in 02152 every 15 minutes.

In the past month, 14 homes have been sold in 02152. In addition to houses in 02152, there were also 47 condos, 4 townhouses, and 12 multi-family units for sale in 02152 last month. Find your dream home in 02152 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 02152 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 02152. If you're looking to sell your home in the 02152 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 02152 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for 02152, MA

Nearby Zip Codes

Cities

Nearby Zip Codes with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in 02152, MA

How to buy a house in 02152, 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

9 Redfin agents serving 02152

172

Deals*

4.8

Satisfaction

1413

Homes closed*

* Data from the last year

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

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: 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, 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

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

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.