Point Shirley, MA homes for sale & real estate

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NEW 22 HRS AGOHOT HOME

88 Grand View Ave, Winthrop, MA 02152
88 Grand View Ave, Winthrop, MA 02152
88 Grand View Ave, Winthrop, MA 02152
ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Welcome to the beach! Enjoy breathtaking sunset views over the city your nightly show from home. This charming property is a perfect condo alternative offering rare first-floor living. The open layout features a brand-new kitchen with polished quartz countertops, two bedrooms, and a beautifully renovated full bath. The second bedroom includes in-unit laundry for added convenience. Step out to a large back deck, perfect for summer nights, overlooking a fenced yard with a new shed and freshly paved driveway. Up the rustic charming open wood staircase to find new carpeting and a flexible space ideal for an office or guest area, plus a third-floor loft for additional storage. Just minutes to th

$665,000

2 beds1 bath1,262 sq ft

88 Grand View Ave, Winthrop, MA 02152

3,607 sq ft lot • Car-dependent

NEW 31 HRS AGO

32 Hale Ave, Winthrop, MA 02152
32 Hale Ave, Winthrop, MA 02152
32 Hale Ave, Winthrop, MA 02152
ABOUT THIS HOME
Point Shirley, MA Homes for Sale
A spectacular hilltop home with unmatched 360° views. A once-in-a-lifetime opportunity to own this exceptional hilltop property offering panoramic views of the Atlantic Ocean, Boston Harbor, Winthrop Harbor, and the Boston skyline. Ocean views from every room and all three decks make this home truly one of a kind. Steeped in history, this site was purposely chosen by Patriot troops during the Revolutionary War as a fortification point to best view the British Ships in the ocean and Boston Harbor—commemorated today by a historic marker at the front of the property. Fully updated and move-in ready. This home features: whole-house A/C, a cozy wood stove insert, spacious main suite wi

$875,000

3 beds2 baths1,418 sq ft

32 Hale Ave, Winthrop, MA 02152

3,879 sq ft lot • Car-dependent

993 Shirley St, Winthrop, MA 02152
993 Shirley St, Winthrop, MA 02152
993 Shirley St, Winthrop, MA 02152
ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Located near Yirrell Beach, this updated single-family home is ready for its next chapter. Inside, you’ll find an open-concept layout with gorgeous hardwood floors that flow throughout. The modern kitchen is a standout, complete with a shiplap ceiling, granite countertops, and stainless-steel appliances-perfect for daily living and entertaining. The first floor offers one bedroom and a versatile bonus room, perfect to use as a second bedroom, home office, playroom, or whatever fits your lifestyle. A full bath on this level adds convenience and comfort. Upstairs features four bedrooms and two full baths, plus additional flex space ideal for guests, hobbies, or remote work. Large window

$839,000

5 beds3 baths2,184 sq ft

993 Shirley St, Winthrop, MA 02152

3,800 sq ft lot • Car-dependent

50 Triton Ave, Winthrop, MA 02152
50 Triton Ave, Winthrop, MA 02152
50 Triton Ave, Winthrop, MA 02152
ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Updated 2 bedroom, 2 bathroom bungalow located in the picturesque Point Shirley neighborhood of Winthrop. This detached single family home, boasting more than 1,300 square feet of living space, was recently renovated throughout to include wood-look porcelain tile, a brand new kitchen with stainless steel appliances and quartz countertops, a brand new master bathroom with a walk in shower including a pebble-stone shower floor and brand new central A/C and heat. This home includes an in unit side-by-side washer and dryer in a dedicated laundry room as well. Walk to beautiful Yirrell Beach in just 6 minutes. Enjoy an afternoon barbecue in your own beautifully manicured private back yard. MBTA

$649,000

2 beds2 baths1,361 sq ft

50 Triton Ave, Winthrop, MA 02152

4,073 sq ft lot • Car-dependent

600 Shirley St #3, Winthrop, MA 02152
600 Shirley St #3, Winthrop, MA 02152
600 Shirley St #3, Winthrop, MA 02152
ABOUT THIS HOME
Point Shirley, MA Homes for Sale
“The Cove at 600” was converted in 2022 and is located on the site of the historic Crystal Cove Hotel with breathtaking views of the Boston Skyline and the Atlantic Ocean. Unit 3, located on the side of the building with a private entrance, exclusive use patio and exclusive use deck at the front of the building offers many ways to take in the view and the sea air. The open concept living room and dining room are bright and airy. The front bedroom is currently used as an office with striking views of the Boston Skyline. The main bedroom features an en-suite ¾ bath with beautiful tiled shower. This unit has baseboard heat and 3 mini splits for a/c. Full Size, in-unit laundr

$549,900

2 beds2 baths773 sq ft

600 Shirley St #3, Winthrop, MA 02152

$695 HOA • Somewhat walkable

Property at 77 Otis St, Winthrop, MA 02152, 4 beds, 2 baths

$814,500

4 beds2 baths1,769 sq ft

77 Otis St, Winthrop, MA 02152

Property at 64 Moore St, Winthrop, MA 02152, 4 beds, 3 baths

$799,000

4 beds3 baths1,777 sq ft

64 Moore St, Winthrop, MA 02152

Property at 138 Grandview Ave, Winthrop, MA 02152, 3 beds, 1.5 baths

$779,000

3 beds1.5 baths1,792 sq ft

138 Grandview Ave, Winthrop, MA 02152

Property at 600 Shirley St #16, Winthrop, MA 02152, 2 beds, 2 baths

$525,000

2 beds2 baths865 sq ft

600 Shirley St #16, Winthrop, MA 02152

Property at 208 Grand View Ave #208, Winthrop, MA 02152, 2 beds, 1 bath

$419,900

2 beds1 bath836 sq ft

208 Grand View Ave #208, Winthrop, MA 02152

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

$415,000

1 bed2 baths604 sq ft

600 Shirley St #1, Winthrop, MA 02152

Property at 1079 Shirley St, Winthrop, MA 02152, 4 beds, 2 baths

$745,000

4 beds2 baths1,660 sq ft

1079 Shirley St, Winthrop, MA 02152

Property at 1077 Shirley St, Winthrop, MA 02152, 2 beds, 1 bath

$420,000

2 beds1 bath540 sq ft

1077 Shirley St, Winthrop, MA 02152

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Nearby homes that match your criteria

247 Washington Ave #9, Winthrop, MA 02152
247 Washington Ave #9, Winthrop, MA 02152
247 Washington Ave #9, Winthrop, MA 02152
ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Beautiful corner end-unit condominium in the desirable Nautilus Building offering panoramic views of Boston, the marina, Winthrop Yacht Club, and Elks from every room. This spacious 2-bedroom, 2-bathroom condominium features a private balcony that spans the entire length of the unit, perfect for relaxing and watching the boats go by. Inside this bright and airy unit, is a white kitchen, hardwood floors and large open-concept living and dining area ideal for entertaining. Both bedrooms are spacious with ample closets and one includes an en-suite bath Enjoy the breeze from the ocean or comfort from your built in air conditioning. The professionally managed Nautilus Condominium is an elevator

$520,000

2 beds2 baths1,116 sq ft

247 Washington Ave #9, Winthrop, MA 02152

$542 HOA • Somewhat walkable

175 Pleasant St, Winthrop, MA 02152
175 Pleasant St, Winthrop, MA 02152
175 Pleasant St, Winthrop, MA 02152
ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Step into timeless charm with this stately 1896 Colonial Revival nestled on a corner lot. Brimming with original detail, this non-conforming two-family offers a flexible layout across 8+ elegant rooms. The grand staircase, French doors, high ceilings, and two fireplaces bring character and warmth throughout. Enjoy four spacious second-floor bedrooms, a sun-soaked landing with a large picture window, and a finished attic with three bonus rooms. A charming butler’s stairwell connects the upper level to the heart of the home—an updated kitchen with Brazilian teak floors, granite island, newer cabinets, and first-floor mudroom. A bonus first-floor room with ensuite bathroom offers v

$949,000

4 beds3 baths4,101 sq ft

175 Pleasant St, Winthrop, MA 02152

5,978 sq ft lot • 2 garage spots • Very walkable

265 Washington Ave Unit 2A, Winthrop, MA 02152
265 Washington Ave Unit 2A, Winthrop, MA 02152
265 Washington Ave Unit 2A, Winthrop, MA 02152
ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Looking for the perfect balance of city convenience and suburban tranquility? This newly renovated 1-bedroom, 1-bathroom condo is just a quick ride to the Orient Heights T stop, making your commute to downtown Boston easy. Plus, you're only 5 minutes from Boston Logan Airport, perfect for travel. Enjoy stunning views of the Boston skyline and harbor right from your door. Stroll to nearby oceanfront beaches where you can relax and unwind by the water whenever you wish. The condo offers a bright, open living space with modern finishes, ideal for a busy professional. Enjoy 2 private entrances! Updates: new kitchen, new bathroom, refinished hardwood floors, tile, new windows, updated electric,

$289,500

1 bed1 bath400 sq ft

265 Washington Ave Unit 2A, Winthrop, MA 02152

$307 HOA • Somewhat walkable

3 Buckthorn #2, Winthrop, MA 02152
3 Buckthorn #2, Winthrop, MA 02152
3 Buckthorn #2, Winthrop, MA 02152
ABOUT THIS HOME
Point Shirley, MA Homes for Sale
Tucked away on a quiet street, this home boasts stately features and has been meticulously renovated. From the elegant newel post to the timeless kitchen details, nothing was overlooked. During the condo conversion, preserving the home's original integrity was a priority. The first floor offers 2 bedrooms, laundry, and a full bath with marble tile floors. The sunlit living room, complete with a fireplace, opens to the dining room and the first of two decks, offering ocean views. The second deck is covered, perfect for rainy days. The kitchen features high-end appliances and classic white cabinetry. Upstairs, find 2 more bedrooms, including a primary with a large walk-in closet and full bath

$799,000

4 beds2 baths1,870 sq ft

3 Buckthorn #2, Winthrop, MA 02152

$334 HOA • Community pool • Very walkable

Average home prices near Point Shirley, MA

Cities

Neighborhoods

Logan Airport / Jeffries Point homes for sale
$849,000
South Boston homes for sale
$1,275,000
East Boston homes for sale
$699,900
Beachmont homes for sale
$799,900
Orient Heights homes for sale
$585,000
Harbor View-Orient Heights homes for sale
$699,450
Jeffries Point homes for sale
$825,000
D Street-West Broadway homes for sale
$1,412,000
Whinthrop Highlands homes for sale
$675,200
Winthrop Beach homes for sale
$599,900

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