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Point Shirley Homes for Sale

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  • 16 Billows St Unit 2, Winthrop, MA 02152
    16 Billows St Unit 2, Winthrop, MA 02152
    16 Billows St Unit 2, Winthrop, MA 02152
    /16

    $565,000

    • 2 Beds
    • 1 Bath
    • 928 Sq Ft

    16 Billows St Unit 2, Winthrop, MA 02152

    This renovated 2-bedroom, 1-bath condo sits in the heart of Winthrop's Point Shirley, offering single-floor living with vaulted ceilings and skylights that give the space a brightness and openness rarely found at this price point. Natural light pours through every room throughout the day, flowing over hardwood floors that run wall to wall and tie the entire living space together seamlessly. Two

    Reserve Team Reference Real Estate

    16 Billows St Unit 2, Winthrop, MA 02152
  • 51 Undine Ave, Winthrop, MA 02152
    51 Undine Ave, Winthrop, MA 02152
    51 Undine Ave, Winthrop, MA 02152
    /36

    $680,000

    $20K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,250 Sq Ft

    51 Undine Ave, Winthrop, MA 02152

    Experience coastal living in a vibrant beachside community featuring a park with tennis and basketball courts, a dog park, and a scenic shoreline overlooking the Boston skyline. This thoughtfully updated home offers peace of mind with a recently painted exterior, a roof approximately 5 years old, and upgraded electrical and plumbing systems. Inside, you’ll find newer flooring, fresh interior

    The Caceda Team Coldwell Banker Realty - Lynnfield

    51 Undine Ave, Winthrop, MA 02152
  • 1001 Shirley St, Winthrop, MA 02152
    1001 Shirley St, Winthrop, MA 02152
    1001 Shirley St, Winthrop, MA 02152
    /34

    $4,724,900

    • 10 Beds
    • 15 Baths
    • 9,156 Sq Ft

    1001 Shirley St, Winthrop, MA 02152

    Rooted in history & reimagined with intention, The Pearl is a one-of-a-kind five-unit multifamily property by the coast in Winthrop. Formerly a church, the building has been thoughtfully transformed into five distinct loft-style residences, each with its own layout, character & design identity. Original architectural details including exposed beams, hardwood floors, oversized windows & dramatic

    The Legacy Group Serhant

    1001 Shirley St, Winthrop, MA 02152
  • 1001 Shirley St Unit 3, Winthrop, MA 02152
    1001 Shirley St Unit 3, Winthrop, MA 02152
    1001 Shirley St Unit 3, Winthrop, MA 02152
    /26

    $849,900

    • 2 Beds
    • 2.5 Baths
    • 1,551 Sq Ft

    1001 Shirley St Unit 3, Winthrop, MA 02152

    Residence 3 at The Pearl offers a bright, refined take on loft living within a reimagined church conversion. Original hardwood floors, exposed beams, oversized windows, and 15’6” ceilings give the home rare scale and character. The kitchen features white cabinetry, Bosch appliances, green soapstone counters, a waterfall island with seating, farmhouse sink, and architectural hood. The living area

    The Legacy Group Serhant

    1001 Shirley St Unit 3, Winthrop, MA 02152
  • 876 Shirley St Unit 1, Winthrop, MA 02152
    876 Shirley St Unit 1, Winthrop, MA 02152
    876 Shirley St Unit 1, Winthrop, MA 02152
    /30

    $829,999

    • 4 Beds
    • 1.5 Baths
    • 2,000 Sq Ft

    876 Shirley St Unit 1, Winthrop, MA 02152

    Direct Ocean Front Living. Feel like you're on vacation every day! This spacious 2 level,7 room, 4 bed, 2 bath condo is located Directly on Yirrell Beach. The sand in your own back yard. Ocean breeze and sounds of the waves crashing onto the shore, are sure to relax you after a long day.Every day the the view is different. Featuring beautiful cherry hard wood floors, Family room, Formal dining

    Jim Iannuzzi Amo Realty - Boston City Properties

    876 Shirley St Unit 1, Winthrop, MA 02152
  • 1001 Shirley St Unit 2, Winthrop, MA 02152
    1001 Shirley St Unit 2, Winthrop, MA 02152
    1001 Shirley St Unit 2, Winthrop, MA 02152
    /39

    $949,900

    • 2 Beds
    • 2.5 Baths
    • 1,806 Sq Ft

    1001 Shirley St Unit 2, Winthrop, MA 02152

    Rooted in history and shaped by design, this loft at The Pearl offers something truly rare. Original hardwood floors and exposed beams, oversized windows & 15’6” ceilings create a striking sense of scale and atmosphere. The kitchen is both refined and dramatic, appointed with White shaker cabinetry, a Moonstone island, London Smoke quartzite, Bosch appliances, architectural hood, and a farmhouse

    The Legacy Group Serhant

    1001 Shirley St Unit 2, Winthrop, MA 02152
  • 129 Strandway, Winthrop, MA 02152
    129 Strandway, Winthrop, MA 02152
    129 Strandway, Winthrop, MA 02152
    /42

    $1,324,900

    • 4 Beds
    • 3 Baths
    • 2,640 Sq Ft

    129 Strandway, Winthrop, MA 02152

    Discover true beachfront living at 129 Strandway, where every day feels like vacation. Step from your back door directly into the sand and enjoy panoramic ocean views from the heated sunroom. The main level offers an updated kitchen with marble counters, a cozy fireplaced living room, two bedrooms, and a convenient beach-entry bath. The spacious second-floor primary suite provides its own private

    Mark Savage Byrnes Real Estate Group LLC

    129 Strandway, Winthrop, MA 02152
  • 27 Billows St, Winthrop, MA 02152
    27 Billows St, Winthrop, MA 02152
    27 Billows St, Winthrop, MA 02152
    /25

    $855,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,837 Sq Ft

    27 Billows St, Winthrop, MA 02152

    This gut-renovated home delivers three levels of flexible living that is hard to replicate. The sun-filled entryway with built-in bench seating & ceiling fan sets a relaxed tone from the moment you walk in. The open main level flows seamlessly from the living room with hardwood floors, beamed ceilings, and built-in electric fireplace through the dining area with its own wine cooler and into a

    Reserve Team Reference Real Estate

    27 Billows St, Winthrop, MA 02152
Massachusetts Suffolk County Winthrop Point Shirley

Real Estate & Homes for Sale in Point Shirley, Winthrop

Why Live in Point Shirley
Point Shirley is a coastal neighborhood in Winthrop approximately 8 miles from Boston. This beach community offers residents stunning views of the Atlantic Ocean and the Boston skyline. The area has shingle-sided beach bungalows and vinyl-sided multi-story homes, many of which were built in the early 20th century and have been remodeled. The neighborhood has a close-knit feel with full-time residents. Point Shirley Beach and Yirrell Beach provide sandy shores for locals, and Winthrop Boat Launch offers access to the water. Recreational options include the Deer Island Loop Trail, Winthrop Golf Club and Coughlin Park, which features a playground and sports courts. Point Shirley is right across the water from Boston Logan International Airport. Students may attend Winthrop Public Schools or the top-rated Immaculate Conception School. Shopping and dining are available nearby, including local favorites like Winthrop Arms Hotel & Restaurant. Public transportation includes MBTA buses and the seasonal Winthrop Ferry, connecting residents to regional destinations.
Learn more about living in Point Shirley

Point Shirley Home Prices vs. Nearby Winthrop, MA Neighborhoods

Point Shirley Maplewood Highlands Monument Beach Buzzards Bay
Median Home Price
$732,000
$676,500
$635,000
$575,000
Median Sale Price
$625,000
-2% YoY
$639,000
-18% YoY
$540,500
-10% YoY
$499,000
+10% YoY
Median Single Family Price
$680,000
$744,000
$615,450
$595,000
Median Condo Price
$839,949
$382,000
$625,000
$524,900
Total Active Listings
7
3
28
29
Market Conditions
5 Months of Supply
Balanced Market
3 Months of Supply
Seller's Market
3 Months of Supply
Seller's Market
4 Months of Supply
Balanced Market

Frequently Asked Questions

Is Point Shirley a good place to live?
Point Shirley is a good place to live. Point Shirley is considered somewhat bikeable. Point Shirley is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Point Shirley has 3 parks for recreational activities. It has a median age of 47. The average household income is $143,613 which is above the national average. College graduates make up 52.9% of residents. A majority of residents in Point Shirley are home owners, with 27% of residents renting and 73% of residents owning their home. A local real estate agent serving Point Shirley can help you decide if this neighborhood is the right one for you. Learn more on our Point Shirley neighborhood guide.
Is Point Shirley, MA a safe neighborhood?
Point Shirley, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Point Shirley?
The median home price in Point Shirley is $732,000. If you put a 20% down payment of $146,400 and had a 30-year fixed mortgage with an interest rate of 6.43%, your estimated principal and interest payment would be $3,670 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $157K a year to afford the median home price in Point Shirley. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Point Shirley is $144K.
What are the best public schools in Point Shirley?
The best public schools that serve Point Shirley are:
What are the most popular zip codes in Point Shirley, Winthrop, MA?
The most popular zip codes in Point Shirley, Winthrop, MA include 02152, 02128, 02151, 02127 and 02150.
What are the most popular neighborhoods near Point Shirley, Winthrop, MA?
The most popular neighborhoods near Point Shirley, Winthrop, MA are Cottage Hill, Winthrop Beach, Downtown Winthrop, Winthrop Highlands and Harbor View-Orient Heights.
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