8

Point Shirley Homes for Sale

Section Image
  • 86 Undine Ave, Winthrop, MA 02152
    86 Undine Ave, Winthrop, MA 02152
    86 Undine Ave, Winthrop, MA 02152
    /4

    $500,000

    • 1 Bed
    • 1 Bath
    • 620 Sq Ft

    86 Undine Ave, Winthrop, MA 02152

    This offering is about the land, the view, and the opportunity to own an affordable single-family property in an exceptional location. Located in Point Shirley, one of Winthrop’s most sought after waterfront neighborhoods, this shovel ready property sits above the Atlantic with wide open views of the ocean, Boston skyline, and the iconic Winthrop water tower. Walkable to the beach, yacht clubs,

    Reserve Team Reference Real Estate

    86 Undine Ave, Winthrop, MA 02152
  • 86 Undine Ave, Winthrop, MA 02152
    86 Undine Ave, Winthrop, MA 02152
    86 Undine Ave, Winthrop, MA 02152
    /11

    $1,350,000

    • 3 Beds
    • 2.5 Baths
    • 2,250 Sq Ft

    86 Undine Ave, Winthrop, MA 02152

    This offering is about the land and the view. Located in Point Shirley, one of Winthrop’s most sought after waterfront neighborhoods, this shovel ready site sits above the Atlantic with wide open views of the ocean, Boston skyline, and the iconic Winthrop water tower. Walkable to the beach, yacht clubs, Winthrop Landing, and the ferry, with an easy commute back to the city. The existing structure

    Reserve Team Reference Real Estate

    86 Undine Ave, Winthrop, MA 02152
  • 86L Undine Ave, Winthrop, MA 02152
    86L Undine Ave, Winthrop, MA 02152
    86L Undine Ave, Winthrop, MA 02152
    /4

    $500,000

    • Land
    • 0.09 Acre
    • $5,555,556 per Acre

    86L Undine Ave, Winthrop, MA 02152

    This offering is about the land and the view. Located in Point Shirley, one of Winthrop’s most sought after waterfront neighborhoods, this shovel ready site sits above the Atlantic with wide open views of the ocean, Boston skyline, and the iconic Winthrop water tower. Walkable to the beach, yacht clubs, Winthrop Landing, and the ferry, with an easy commute back to the city. The existing structure

    Reserve Team Reference Real Estate

    86L Undine Ave, Winthrop, MA 02152
  • 1001 Shirley St Unit 5, Winthrop, MA 02152
    1001 Shirley St Unit 5, Winthrop, MA 02152
    1001 Shirley St Unit 5, Winthrop, MA 02152
    /16

    $1,050,000

    • 2 Beds
    • 2.5 Baths
    • 1,785 Sq Ft

    1001 Shirley St Unit 5, Winthrop, MA 02152

    Welcome to Unit 5 at The Pearl, a boutique coastal residence at 1001 Shirley Street, where refined design meets oceanfront living. This thoughtfully crafted home offers sweeping Atlantic views and a private ocean facing balcony, creating a daily connection to the water that few properties can match. Inside, the space is defined by clean architectural lines, generous ceiling height, and a layout

    Reserve Team Reference Real Estate

    1001 Shirley St Unit 5, 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
    /14

    $849,999

    • 4 Beds
    • 2 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. Featuring beautiful cherry hard wood floors, Family room, Formal dining room, ( Living room-could be master

    Jim Iannuzzi Amo Realty - Boston City Properties

    876 Shirley St Unit 1, 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

    Kovacs Savage Team Byrnes Real Estate Group LLC

    129 Strandway, Winthrop, MA 02152
  • 1001 Shirley St Unit 1, Winthrop, MA 02152
    1001 Shirley St Unit 1, Winthrop, MA 02152
    1001 Shirley St Unit 1, Winthrop, MA 02152
    /25

    $1,125,000

    • 2 Beds
    • 2.5 Baths
    • 1,978 Sq Ft

    1001 Shirley St Unit 1, Winthrop, MA 02152

    As the flagship residence at The Pearl, Unit 1 showcases one of the most spacious layouts in the collection, blending ocean views with striking modern details. Steps from the shoreline in Winthrop’s Point Shirley, it spans two levels with hardwood floors, soaring cathedral beamed ceilings, and a fireplace that anchors the living room while a second warms the primary suite. The chef’s kitchen is

    Reserve Team Reference Real Estate

    1001 Shirley St Unit 1, 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
    /21

    $939,900

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

    1001 Shirley St Unit 3, Winthrop, MA 02152

    Once a cornerstone of the Point Shirley community, this former church has been completely reimagined into five striking townhomes that blend architectural soul with modern precision. The Pearl is a bold statement... Thoughtful design, coastal light, and space that actually feels like home. Unit 3 offers over 1,500 square feet across two levels with an open main floor that feels expansive but

    Reserve Team Reference Real Estate

    1001 Shirley St Unit 3, 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

Frequently Asked Questions

Is Point Shirley a good place to live?
Point Shirley is a good place to live. Point Shirley is considered very car-dependent and 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 1 park 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 27.2% of residents renting and 72.8% 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 $677,500. If you put a 20% down payment of $135,500 and had a 30-year fixed mortgage with an interest rate of 6.09%, your estimated principal and interest payment would be $3,280 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $141K 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, Cottage Park, Winthrop Beach, Downtown Winthrop and Winthrop Highlands.

Home Trends in Point Shirley, MA

On average, homes in Point Shirley, Winthrop sell after 47 days on the market compared to the national average of 54 days. The median sale price for homes in Point Shirley, Winthrop over the last 12 months is $620,000, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$620,000
Median Single Family Sale Price
$637,500
Median Townhouse Sale Price
$605,000
Median 2 Bedroom Sale Price
$939,900
Average Price Per Sq Ft
$505
Number of Homes for Sale
6
Last 12 months Home Sales
21
Months of Supply
3.40
Median List Price
$677,500
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-3%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group