Point Shirley, MA homes for sale & real estate

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OPEN SAT, 11AM TO 12:30PMFLOOR PLAN

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Welcome to 33 Bay View Ave, a charming coastal bungalow offering the perfect blend of comfort, convenience, and seaside living in Winthrop. This 3-bedroom, 1-bath home features hardwood floors, a bright and inviting living space, dedicated dining area, and a functional kitchen with new appliances. Enjoy water views and take advantage of the spacious fenced in yard, ideal for entertaining, gardening, or relaxing outdoors. Additional highlights include an enclosed porch, wood deck, patio, first-floor laundry, and off street parking. Located just moments from the beach, parks, walking and biking trails, public transportation, and all that Winthrop has to offer. A great opportunity to enjoy the

$625,000

3 beds1 bath931 sq ft

33 Bay View Ave, Winthrop, MA 02152

Water views • Wood deck • Enclosed porch

3D WALKTHROUGH

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. Special developer pricing now offered at 775,000 Seller reserves the right to accept, reject, or counter any offer and may request highest and best. Pricing and terms subject to change without notice. Buyers are encouraged to submit their strongest offer promptly.

$775,000

2 beds2.5 baths1,551 sq ft

1001 Shirley St #3, Winthrop, MA 02152

Private deck • Historic loft • Premium appliances

OPEN SAT, 10AM TO 12PM

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
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! Spacious kitchen w/ water views o

$649,000

3 beds1.5 baths1,200 sq ft

84 Tafts Ave, Winthrop, MA 02152

Fully renovated • Water views • Cedar closets

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. Special developer pricing now offered at 865,000.00 Seller reserves the right to accept, reject, or counter any offer and may request highest and best. Pricing and terms subject to change without notice. Buyers are encouraged to submit their strongest offer promptly.

$865,000

2 beds2.5 baths1,806 sq ft

1001 Shirley St #2, Winthrop, MA 02152

Private deck • Historic loft • Premium appliances

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Cape-style home in Point Shirley, steps from the beach and within Winthrop's most walkable stretch of coastline. Built in 1900 and updated with a remodeled kitchen featuring granite counters and recessed lighting, plus a remodeled full bath with a tiled tub and shower. Original hardwood floors run through the main level and all four bedrooms, paired with bay windows that bring in natural light and water views. The main level includes a living room with a fireplace, a formal dining room, and a sunroom that opens to a screened porch. Central air and forced air heat keep the home comfortable year-round. A full basement with sump pump offers storage and utility space, and a paved driveway provi

$715,000

4 beds1.5 baths1,586 sq ft

52 Pebble Ave, Winthrop, MA 02152

Remodeled kitchen • Bay windows • Tiled tub

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 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

$659,900

3 beds1 bath1,250 sq ft

51 Undine Ave, 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 876 Shirley St #1, Winthrop, MA 02152, 4 beds, 1.5 baths

$799,999

4 beds1.5 baths2,000 sq ft

876 Shirley St #1, Winthrop, MA 02152

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

$1,324,900

4 beds3 baths2,640 sq ft

129 Strandway, Winthrop, MA 02152

Property at 600 Shirley #4, Winthrop, MA 02152, 1 bed, 2 baths

$384,888

1 bed2 baths585 sq ft

600 Shirley #4, Winthrop, MA 02152

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ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Stop throwing away money on rent and start building equity in the heart of Winthrop’s vibrant seaside community! This isn't just a condo; it’s your gateway to a coastal lifestyle without the premium price tag. Step inside this move-in-ready, first-floor gem and you’ll immediately notice the fresh, modern energy. The entire space has been reimagined with sleek new vinyl flooring and a stunning quartz kitchen that’s just waiting for your first dinner party. With four rooms total, you get the benefit of a spacious primary bedroom plus a dedicated, good-sized office—perfect for the remote professional or anyone needing that extra creative space. Life here is all ab

$309,900

1 bed1 bath720 sq ft

483 Shirley St Unit 6A, Winthrop, MA 02152

Vinyl flooring • Quartz kitchen • Dedicated office

OPEN SAT, 12PM TO 2PM

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Welcome to coastal living at its best — where ocean views meet beautiful golf course views, and the beach is just a five-minute walk from your front door. Fully rebuilt in 2025, this exceptional first-floor 2-bedroom, 2-bath residence offers the rare combination of brand-new luxury, thoughtful design, and an incredible Winthrop-by-the-Sea location. Every detail was carefully considered, creating a home that feels elegant, comfortable, and effortless. Step inside to gleaming hardwood floors, beautiful natural light, and an inviting open living space. The chef’s kitchen is beautifully designed with quality finishes, generous workspace and storage, creating a perfect setting for co

$550,000

2 beds2 baths756 sq ft

194 Washington Ave #4, Winthrop, MA 02152

Spa-like bathrooms • First-floor living • Ocean views

OPEN SAT, 12PM TO 2PM

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Welcome to coastal living at its best — where ocean views meet beautiful golf course views, and the beach is just a five-minute walk from your front door. Fully rebuilt in 2025, this exceptional first-floor 2-bedroom, 2-bath residence offers the rare combination of brand-new luxury, thoughtful design, and an incredible Winthrop-by-the-Sea location. Every detail was carefully considered, creating a home that feels elegant, comfortable, and effortless. Step inside to gleaming hardwood floors, beautiful natural light, and an inviting open living space. The chef’s kitchen is beautifully designed with quality finishes, generous workspace and storage, creating a perfect setting for co

$600,000

2 beds2 baths912 sq ft

194 Washington Ave #2, Winthrop, MA 02152

First-floor living • Ocean views • Spa-like bathroom

OPEN SAT, 12PM TO 2PM

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Welcome to coastal living at its best — where ocean views meet sweeping golf course views, and the beach is just a five-minute walk from your front door. Fully rebuilt in 2025, this exceptional 3-bedroom, 3-bath residence offers the rare combination of brand-new luxury, thoughtful design, and an incredible Winthrop-by-the-Sea location. Every detail was carefully considered, creating a home that feels elegant, comfortable, and effortless. Step inside to gleaming hardwood floors and beautiful natural light flowing through the open living space. At the heart of the home is a chef’s kitchen with a large center island, quality finishes, and plenty of room to gather, cook, entertain,

$850,000

3 beds3 baths1,780 sq ft

194 Washington Ave #3, Winthrop, MA 02152

Spa-like bathrooms • Tankless hot water • Ocean views

OPEN SAT, 11AM TO 12:30PM

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Welcome to 190 Pleasant Street, a spacious two-family home offering approximately 4,251 square feet of living space across three levels. Featuring 13 total rooms, seven bedrooms, two full bathrooms and two half bathrooms, this property presents an excellent opportunity for an owner-occupant, investor or multigenerational household. Each unit offers generous living space, while the home’s flexible layout provides plenty of potential to customize and add value. Conveniently located near Winthrop’s beaches, local shops, restaurants, public transportation and Boston. Bring your vision and discover everything this well-located two-family property has to offer!

$949,000

7 beds3 baths4,251 sq ft

190 Pleasant St, Winthrop, MA 02152

Flexible layout • Two family home • Local shops

OPEN SUN, 11AM TO 12:30PMFLOOR PLAN

ABOUT THIS HOME
Point Shirley, MA Homes for Sale
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

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

$998,900

6 beds2.5 baths3,263 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

$2,380,000

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

Property at 142 Pleasant St #12, Winthrop, MA 02152, 2 beds, 1.5 baths

$595,000

2 beds1.5 baths1,141 sq ft

142 Pleasant St #12, Winthrop, MA 02152

Average home prices near Point Shirley, MA

Cities

Neighborhoods

Logan Airport / Jeffries Point homes for sale
$669,000
South Boston homes for sale
$1,200,000
East Boston homes for sale
$749,937
Beachmont homes for sale
$554,725
Orient Heights homes for sale
$880,000
Harbor View-Orient Heights homes for sale
$749,937
Jeffries Point homes for sale
$669,500
South Boston Waterfront homes for sale
$1,450,000
Whinthrop Highlands homes for sale
$600,000
Winthrop Beach homes for sale
$512,400

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