Vintage homes for sale & real estate in Winthrop, MA

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ABOUT THIS HOME
Vintage Home for sale in Winthrop, MA:
Attention investors, builders, and contractors! A truly rare opportunity awaits at 104-106 Shirley Street, Winthrop. Situated on an impressive double lot spanning over 10,000 square feet, this property offers incredible upside and potential. The existing home features some fire damage, allowing buyers the flexibility to perform selective renovations, execute a partial demo, or complete a full renovation to suit their vision. Double lots of this footprint are nearly impossible to find in Winthrop, making it an ideal project for tradespeople, savvy investors and whoever looking to add substantial value. Located just minutes from beaches, shops, dining, transit, and a short commute into Bosto

$749,974

5 beds2 baths2,520 sq ft

104-106 Shirley St, Winthrop, MA 02152

Minutes from beaches • Double lot • Full renovation

ABOUT THIS HOME
Vintage Home for sale in Winthrop, MA:
This is your chance to live in Winthrop by the sea. This condo is located in a section of Winthrop known as Point Shirley. This condo is surrounded by amenities. The MBTA. bus to Boston or Logan airport stops directly across the street from your front door at the same place the local school bus stops. Winthrop also has a MBTA. water taxi to Boston. It's a fun ride across Boston harbor. The town beach is only a two-minute walk. Just grab your gear leave the car home and have fun. The neighborhood is great for walking and biking either on the beach or on Grandview ave. You will have on site parking plus curbside parking. Winthrop has three yacht clubs two boat marinas and a golf course. It al

$498,500

2 beds1.5 baths1,002 sq ft

1020 Shirley St #1020, Winthrop, MA 02152

On site parking • Curbside parking • Two boat marinas

ABOUT THIS HOME
Vintage Home for sale in Winthrop, MA:
Move right into this beautifully updated two-bedroom, one-bath condominium at 29 Seafoam Ave, located less than 500 feet from Winthrop Beach. Recent upgrades include a fully renovated bathroom, fresh interior paint, updated kitchen, and newly refinished hardwood floors, offering a turnkey opportunity from day one. The move-in ready home also features dedicated laundry, direct access to an exclusive-use covered front and side porch, access to a shared backyard, and assigned parking for two vehicles, a rare find in this coastal community. Positioned in a recreation-lover's paradise, this property is just half a mile from the Winthrop Golf Club and Boston Tennis, and under a mile from the Wint

$425,000

2 beds1 bath861 sq ft

29 Seafoam Ave #1, Winthrop, MA 02152

Dedicated laundry • Updated kitchen • Assigned parking

ABOUT THIS HOME
Vintage Home for sale in Winthrop, MA:
Welcome to 23 Trident Avenue, Unit 1, in the desirable seaside community of Winthrop! This spacious first-floor condominium offers approximately 1,374 square feet of living space, featuring 7 rooms, 3 bedrooms, 1 full bathroom, and a versatile bonus room ideal for a home office, creative space, or additional flex space. Thoughtful improvements by the current owner include a new refrigerator, garbage disposal, ceiling fans, bathroom was repainted, and updated light fixtures. Additional highlights include TWO off-street parking spaces and convenient basement storage, providing valuable extra room for your belongings. Enjoy all that coastal living has to offer with nearby beaches, local restau

$519,000

3 beds1 bath1,374 sq ft

23 Trident #1, Winthrop, MA 02152

Garbage disposal • Ceiling fans • Bonus room

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Winthrop, MA:
Charming, move-in-ready Colonial offering ocean views in a desirable Winthrop location just moments from the newly renovated Winthrop Beach. The inviting main level features a sun-filled living room with a gas fireplace and classic arched doorways, a spacious kitchen overlooking the covered deck and fenced backyard, a formal dining room, a half bath, and a versatile room currently used as a home office. Upstairs, you'll find three spacious bedrooms, a cozy sitting area, and a full bath. A porch roof patio over looking the ocean is a favorite spot to appreciate the views while you sit back and reflect on your day. Perfect ADU potential or in-law space in the lovingly finished and convenientl

$799,900

5 beds2.5 baths2,437 sq ft

43 Dolphin Ave, Winthrop, MA 02152

Covered deck • Adu potential • In-law space

Property at 16 Loring Rd, Winthrop, MA 02152, 2 beds, 1 bath

$569,000

2 beds1 bath1,692 sq ft

16 Loring Rd, Winthrop, MA 02152

Property at 14 Irwin St, Winthrop, MA 02152, 3 beds, 1.5 baths

$665,000

3 beds1.5 baths1,413 sq ft

14 Irwin St, Winthrop, MA 02152

Property at 7 Enfield Rd, Winthrop, MA 02152, 2 beds, 1 bath

$679,900

2 beds1 bath1,144 sq ft

7 Enfield Rd, Winthrop, MA 02152

Property at 129 Strandway, Winthrop, MA 02152, 4 beds, 3 baths

$1,275,000

4 beds3 baths2,599 sq ft

129 Strandway, Winthrop, MA 02152

Property at 15 Ocean #206, Winthrop, MA 02152, 2 beds, 2 baths

$540,000

2 beds2 baths1,295 sq ft

15 Ocean #206, Winthrop, MA 02152

Property at 62 Pleasant St #2, Winthrop, MA 02152, 3 beds, 2 baths

$624,995

3 beds2 baths1,690 sq ft

62 Pleasant St #2, Winthrop, MA 02152

Property at 63 Harbor View Ave, Winthrop, MA 02152, 4 beds, 2 baths

$1,500,000

4 beds2 baths2,852 sq ft

63 Harbor View Ave, Winthrop, MA 02152

Property at 23-25 Fremont St, Winthrop, MA 02152, 6 beds, 3 baths

$1,250,000

6 beds3 baths3,420 sq ft

23-25 Fremont St, Winthrop, MA 02152

Property at 483 Shirley St Unit 6A, Winthrop, MA 02152, 1 bed, 1 bath

$299,900

1 bed1 bath720 sq ft

483 Shirley St Unit 6A, Winthrop, MA 02152

Property at 43 Sagamore Ave #1, Winthrop, MA 02152, 2 beds, 1 bath

$449,900

2 beds1 bath805 sq ft

43 Sagamore Ave #1, Winthrop, MA 02152

Property at 54 Trident Ave #54, Winthrop, MA 02152, 2 beds, 1 bath

$565,995

2 beds1 bath1,614 sq ft

54 Trident Ave #54, Winthrop, MA 02152

Property at 35 Triton Ave, Winthrop, MA 02152, 3 beds, 2 baths

$799,900

3 beds2 baths1,782 sq ft

35 Triton Ave, Winthrop, MA 02152

Property at 217 Pleasant St, Winthrop, MA 02152, 6 beds, 2.5 baths

$947,900

6 beds2.5 baths2,650 sq ft

217 Pleasant St, Winthrop, MA 02152

Property at 94 Winthrop Shore Dr, Winthrop, MA 02152, 2 beds, 3 baths

$1,095,000

2 beds3 baths2,649 sq ft

94 Winthrop Shore Dr, Winthrop, MA 02152

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

$549,000

2 beds1 bath846 sq ft

16 Billows St, Winthrop, MA 02152

Property at 33 Bay View Ave, Winthrop, MA 02152, 3 beds, 1 bath

$580,000

3 beds1 bath931 sq ft

33 Bay View Ave, Winthrop, MA 02152

Property at 84 Tafts Ave, Winthrop, MA 02152, 3 beds, 1.5 baths

$629,000

3 beds1.5 baths1,200 sq ft

84 Tafts Ave, Winthrop, MA 02152

Property at 15 Ocean Ave #203, Winthrop, MA 02152, 2 beds, 2.5 baths

$499,900

2 beds2.5 baths1,210 sq ft

15 Ocean Ave #203, Winthrop, MA 02152

Property at 1001 Shirley St #4, Winthrop, MA 02152, 2 beds, 2.5 baths

$815,000

2 beds2.5 baths1,665 sq ft

1001 Shirley St #4, Winthrop, MA 02152

Property at 194 Washington Ave #4, Winthrop, MA 02152, 2 beds, 2 baths

$540,000

2 beds2 baths756 sq ft

194 Washington Ave #4, Winthrop, MA 02152

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

$349,000

2 beds1 bath677 sq ft

53 Trident Ave #301, Winthrop, MA 02152

Property at 93 1/2 Winthrop Shore Dr, Winthrop, MA 02152, 3 beds, 1.5 baths

$900,000

3 beds1.5 baths1,334 sq ft

93 1/2 Winthrop Shore Dr, Winthrop, MA 02152

Property at 35 Somerset Ave Unit 3A, Winthrop, MA 02152, 2 beds, 2 baths

$529,900

2 beds2 baths969 sq ft

35 Somerset Ave Unit 3A, Winthrop, MA 02152

Property at 25 Locust St #2, Winthrop, MA 02152, 3 beds, 2 baths

$849,000

3 beds2 baths1,770 sq ft

25 Locust St #2, Winthrop, MA 02152

Property at 194 Washington Ave #3, Winthrop, MA 02152, 3 beds, 3 baths

$825,000

3 beds3 baths1,780 sq ft

194 Washington Ave #3, Winthrop, MA 02152

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

$549,000

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 194 Washington Ave #2, Winthrop, MA 02152, 2 beds, 2 baths

$575,000

2 beds2 baths912 sq ft

194 Washington Ave #2, Winthrop, MA 02152

Property at 111 Locust St #2, Winthrop, MA 02152, 3 beds, 1 bath

$525,000

3 beds1 bath1,270 sq ft

111 Locust St #2, Winthrop, MA 02152

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

$2,100,000

5 beds5.5 baths6,224 sq ft

174 Bartlett Rd, Winthrop, MA 02152

Property at 1001 Shirley St #1, Winthrop, MA 02152, 2 beds, 2.5 baths

$965,000

2 beds2.5 baths1,978 sq ft

1001 Shirley St #1, Winthrop, MA 02152

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

$635,000

3 beds2 baths800 sq ft

496 Winthrop St, Winthrop, MA 02152

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

$617,000

3 beds2.5 baths1,510 sq ft

189 Shirley #2, Winthrop, MA 02152

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

$740,000

6 beds2 baths2,000 sq ft

120 Hermon St, Winthrop, MA 02152

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

$350,000

2 beds1 bath649 sq ft

175 Shirley St #5, Winthrop, MA 02152

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

$724,000

3 beds2.5 baths1,800 sq ft

189 Shirley St #1, Winthrop, MA 02152

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Vintage Homes for Sale in Winthrop

There are currently 52 vintage homes for sale in Winthrop at a median listing price of $638K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winthrop stay on the market for 51 days and receive 1 offers. Popular neighborhoods include Logan Airport / Jeffries Point, East Boston, Beachmont, Orient Heights, and Jeffries Point. This map is refreshed with the newest listings in Winthrop every 15 minutes.

In the past month, 19 homes have been sold in Winthrop. In addition to houses in Winthrop, there were also 67 condos, 5 townhouses, and 10 multi-family units for sale in Winthrop last month. Find your dream home in Winthrop 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 Winthrop are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winthrop. Our Winthrop real estate stats and trends will give you more information about home buying and selling trends in Winthrop. If you're looking to sell your home in the Winthrop area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winthrop with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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