Point Shirley, MA homes for sale & real estate

15 homes

Sort:

Recommended

NEW CONSTRUCTION

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Build your Point Shirley home on a lot that already has Winthrop Zoning Board approval for a single family. The zoning work is finished, so you can go straight to design and permitting. Go up two or three stories and the upper floors open to ocean views and a clear line to the Boston skyline. Mornings on the water, evenings watching the city lights, and Logan and downtown Boston only minutes away. Located beside 54 Otis St. Also offered as land MLS 73594294. Fully approved lot for single family build, variance recorded with registry of deeds.

$379,000

Studio— baths— sq ft

Lot 190 Otis St, Winthrop, MA 02152

Boston skyline • Minutes away • Ocean views

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Historic loft at The Pearl with soaring ceilings, oversized windows, and original wood details. kitchen with premium appliances and stone surfaces. Private deck off the primary suite with radiant heated bath. Two off-street parking spaces, private storage, secure entry. Come and enjoy what Winthrop has to offer, beaches, paths, cafes, a golf course, public pickleball & tennis courts with easy Boston access. Unit is listed for sale and lease!

$865,000

2 beds2.5 baths1,806 sq ft

1001 Shirley St #2, Winthrop, MA 02152

Private deck • Historic loft • Off street parking

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
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

LISTED BY REDFIN3D & VIDEO TOUR

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Welcome to your ultimate beachfront oasis in Winthrop, where every day feels like a permanent getaway with direct access from your back door straight into the sand. This stunning home features an inviting, fireplaced living room, a kitchen boasting sleek marble countertops and tile flooring, a convenient main-floor full bath and an outdoor shower for rinsing off after the beach, and two flexible bedrooms ideal for guests, children, or a home office. Take in breathtaking ocean sunrises over morning coffee from the year-round heated sunroom, and retreat upstairs to a spacious primary suite complete with its own private bath. The finished lower level functions as a fully separate suite—a

$1,275,000

4 beds3 baths2,599 sq ft

129 Strandway, Winthrop, MA 02152

Beachfront oasis • Marble countertops • Outdoor shower

OPEN TODAY, 11:30AM TO 1PMFLOOR PLAN

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
The street name—Harbor View Avenue—says it all! A home any sea captain would be proud to call home! Rare opportunity to own a distinctive multi-family property perched at one of Winthrop’s highest elevations, with sweeping panoramic views of the ocean and Boston Harbor and Skyline. Enjoy spectacular sunrises, sunsets, passing boats, and refreshing ocean breezes from this exceptional coastal setting. Classic Hardie Board siding adds timeless New England character, while public stairs just steps away provide convenient access to Yirrell Beach and its shoreline walks. The flexible multi-family layout offers excellent options for an owner-occupant, multi-generational living, o

$1,500,000

4 beds2 baths2,852 sq ft

63 Harbor View Ave, Winthrop, MA 02152

Elevated location • Panoramic views • Beach access

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

$619,000

3 beds1.5 baths1,200 sq ft

84 Tafts Ave, 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 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 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 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 16 Billows St Unit B, Winthrop, MA 02152, 2 beds, 1 bath

$499,000

2 beds1 bath928 sq ft

16 Billows St Unit B, Winthrop, MA 02152

Property at 876 Shirley St #1, Winthrop, MA 02152, 4 beds, 1.5 baths

$795,999

4 beds1.5 baths2,000 sq ft

876 Shirley St #1, 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 51 Undine Ave, Winthrop, MA 02152, 3 beds, 1 bath

$659,800

3 beds1 bath1,250 sq ft

51 Undine Ave, Winthrop, MA 02152

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

COMING SOONFLOOR PLAN

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Truly exceptional waterfront Victorian, with glorious views of Crystal Cove and direct private access to Boston Harbor and beyond, is historic yet fresh, sophisticated yet wonderfully livable! Head out on your boat to explore beaches and islands, restaurants and bars, or relax and enjoy spectacular water views from almost every room. The bespoke water-facing chef's kitchen, with a welcoming island, bar sink and beverage fridge, coffee bar, and suite of Bosch appliances, is an inviting place to gather, cook and linger. Adjacent, the family room beckons, sliding doors bring the outdoors in, and connect to a deck just steps to your own beach. Natural light changes with the day and seasons; the

$1,995,000

5 beds3.5 baths3,686 sq ft

119 Washington Ave, Winthrop, MA 02152

Hardwood flooring • Roof deck • 400-amp electrical

NEW CONSTRUCTION

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Welcome to 28 Thornton Park, a stunning new-construction luxury townhouse in the heart of Winthrop. Spread across three thoughtfully designed levels, this home blends timeless architectural character with the comfort and quality of brand-new construction, all just minutes from Boston. The lower level basement is great height and could be finished. The sun-filled first floor is made for living and entertaining. Graceful arches, custom details and walls of windows fill the open layout with beautiful natural light. The gorgeous living room features soaring cathedral ceilings and flows into the dining area and a chef's kitchen designed for everyday cooking and holiday gatherings alike. Large sl

$949,000

3 beds3.5 baths2,000 sq ft

28 Thornton Park Unit B, Winthrop, MA 02152

Lower level basement • New construction • True primary suite

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Welcome to 14 Irwin Street, a charming single-family home in one of Winthrop’s inviting residential neighborhoods. Offering approximately 1,413 square feet of living space, this classic two-story home features 3 bedrooms, 1.5 bathrooms, and 7 total rooms, providing a comfortable foundation for your next chapter. Enjoy the best of Winthrop’s coastal lifestyle with the beach just a short walk away at the end of the street. Plus, with a bus stop just steps away, public transportation is conveniently accessible for an easier daily commute. From morning walks by the water to summer afternoons at the beach, this location makes everyday living feel a little more special. Set on an appr

$665,000

3 beds1.5 baths1,413 sq ft

14 Irwin St, Winthrop, MA 02152

5,000 sq ft lot • 3 parking spots • Built 1900

OPEN TODAY, 11:30AM TO 1PMVIDEO TOUR

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Welcome to The Somerset unit 205, an elevated boutique condominium in the heart of Winthrop, where refined modern living meets a relaxed coastal lifestyle. This beautifully designed 1+ bedroom, 1-bath residence features an open-concept layout with sophisticated finishes, including a sleek kitchen with quartz countertops and stainless steel appliances. Central A/C and elevator access add everyday comfort, while the building’s fitness room and inviting common area create an effortless sense of community. Ideally located near Winthrop’s beaches, waterfront, shops, restaurants, and cafés, The Somerset offers a stylish coastal retreat with convenient access to downtown Boston.

$491,900

1 bed1 bath691 sq ft

10 Somerset #205, Winthrop, MA 02152

Quartz countertops • Boutique condominium • Fitness room

OPEN TODAY, 1PM TO 2PM

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
THIS ONE FEELS LIKE A SINGLE FAMILY HOME!!! Off in the distance you will enjoy spectacular sunsets over the water in this beautifully renovated and spacious two-level condominium offering 3 bedrooms, 2 full baths and an open layout ideal for ease of living and outside enjoy exclusive to this unit yard space with deck, paver patio and fire pit. Highlights include new paint, lighting, an updated kitchen, updated baths, central air, in-unit laundry, a striking staircase and more of those ocean views from various windows. Commuting is easy with the Boston bus line nearby, providing access to the T in approximately 15 minutes and Boston in about 30. The Winthrop Ferry offers another convenient o

$624,995

3 beds2 baths1,690 sq ft

62 Pleasant St #2, Winthrop, MA 02152

Updated baths • In-unit laundry • Updated kitchen

3D WALKTHROUGH

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
* * $20k in seller credits available * * Gut renovated and converted in 2020, this upper-level 2-bedroom, 2-bath condo at 34 Underhill Street brings new construction finishes to one of Winthrop's most sought-after pockets. The white shaker kitchen is fitted with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including electric cooking. Wide plank hardwood floors & high ceilings run throughout, and recessed lighting and energy efficient mini-split systems keep the space comfortable year-round. The primary bedroom includes a custom walk-in closet with built-in shelving and drawers and direct access to a full bath. Upstairs positioning me

$465,000

2 beds2 baths903 sq ft

34 Underhill St #4, Winthrop, MA 02152

Quartz countertops • White shaker kitchen • Gold hardware

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

$939,000

6 beds2.5 baths2,650 sq ft

217 Pleasant St, 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 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

$2,100,000

5 beds5.5 baths6,224 sq ft

174 Bartlett Rd, 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

Average home prices near Point Shirley, MA

Cities

Neighborhoods

Logan Airport / Jeffries Point homes for sale
$667,000
South Boston homes for sale
$1,199,999
East Boston homes for sale
$709,000
Beachmont homes for sale
$894,900
Orient Heights homes for sale
$749,900
Harbor View-Orient Heights homes for sale
$687,450
Jeffries Point homes for sale
$669,500
South Boston Waterfront homes for sale
$1,449,999
Whinthrop Highlands homes for sale
$599,000
Winthrop Beach homes for sale
$549,948

More to explore in Point Shirley, MA

How to buy a house in Point Shirley, 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

8 Redfin agents serving Point Shirley

150

Deals*

4.8

Satisfaction

1316

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.