Cottage Hill, MA homes for sale & real estate

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42 Harborview Ave #2, Winthrop, MA 02152
42 Harborview Ave #2, Winthrop, MA 02152
42 Harborview Ave #2, Winthrop, MA 02152
ABOUT THIS HOME
Cottage Hill, MA Homes for Sale
Live by the water and soak in ocean, harbor, and Boston skyline views from this renovated 3-bed, 1.5-bath condo on Cottage Hill! Spanning the full second floor with 1,165 sf, this sunlit home features double bay windows, hardwood floors, and an open layout for easy living and entertaining. The updated kitchen boasts gas cooking, granite counters, and stainless appliances. Enjoy central AC, in-unit laundry, private basement storage, and a pet-friendly association with low HOA fees. Relax on your private deck, grill in the shared yard, and take advantage of nearby beaches, restaurants, shops, and the water shuttle. Easy on-street parking. Come see the views and this beautiful home at the open

$630,000

3 beds1.5 baths1,166 sq ft

42 Harborview Ave #2, Winthrop, MA 02152

Harbor views • Renovated condo • Open layout

25 Charles St, Winthrop, MA 02152
25 Charles St, Winthrop, MA 02152
25 Charles St, Winthrop, MA 02152
ABOUT THIS HOME
Cottage Hill, MA Homes for Sale
Welcome to this beautifully updated 3-bedroom, 1.5-bath home just two houses away from Winthrop Beach. This inviting home offers the perfect blend of comfort, style, and seaside living. Bright and spacious open-concept first floor, ideal for entertaining and everyday living with a convenient half bath off of the living room and sliders off of the dining room]. Upstairs are 3 spacious bedrooms, one features a private balcony with views of the beach—your own personal retreat to unwind and take in the sea breeze. Each bedroom is equipped with individually controlled electric heat, offering personalized comfort year-round. The brand new full bathroom is a true spa-like oasis, complete wit

$739,999

3 beds1.5 baths1,994 sq ft

25 Charles St, Winthrop, MA 02152

Double vanity • In-ground pool • Private balcony

600 Shirley St #15, Winthrop, MA 02152
600 Shirley St #15, Winthrop, MA 02152
600 Shirley St #15, Winthrop, MA 02152

$340,000

0 beds1 bath338 sq ft

600 Shirley St #15, Winthrop, MA 02152

$297 HOA • 2 parking spots • Built 1900

3D WALKTHROUGH

100 Cottage Ave, Winthrop, MA 02152
100 Cottage Ave, Winthrop, MA 02152
100 Cottage Ave, Winthrop, MA 02152
ABOUT THIS HOME
Cottage Hill, MA Homes for Sale
Ideally located just steps from the Winthrop Yacht Club, The Landing, local restaurants, and both Winthrop and Yirrell Beach, this spacious single-family home offers stunning water views and a clear line to Boston’s skyline. The first level features a unique and expansive layout with a formal living and dining room anchored by a double-sided fireplace wrapped in lava-rock, plus two additional rooms perfect for a family room, guest room, or home office. The updated eat-in kitchen includes a convenient half bath with in-unit laundry and plenty of cabinet space with a Wolf Cooktop, Miele dishwasher and newer range. The upstairs offers three spacious bedrooms including an expansive oversi

$854,900

3 beds2.5 baths2,293 sq ft

100 Cottage Ave, Winthrop, MA 02152

Water views • Future expansion • In-unit laundry

OPEN SAT, 12PM TO 1PM3D WALKTHROUGH

24 Winthrop Shore Dr #2, Winthrop, MA 02152
24 Winthrop Shore Dr #2, Winthrop, MA 02152
24 Winthrop Shore Dr #2, Winthrop, MA 02152
ABOUT THIS HOME
Cottage Hill, MA Homes for Sale
WELCOME TO OCEAN FRONT LIVING ON WINTHROP BEACH. OCEAN VIEWS , OCEAN VIEWS, OCEAN VIEWS ! Wake up every morning and sit and enjoy the beautiful views of Winthrop Beach and the sun rising. Large Massport Windows that let in a ton of sunlight , step out of your door and put your feet in the sand ! This WELL MAINTAINED TOP CORNER UNIT condo boasts scenic views, hardwood thru out, newer tiled bath, freshly painted , 2020 NEW ROOF, FRONT SIDING , AND HOT WATER HEATER. Plenty of private storage in basement, bedrooms can be switched around and extra room can be office space or child bedroom. JUST MOVE RIGHT IN . Come see what Winthrop has to offer , many great restaurants, bars, beaches, waking

$434,000

2 beds1 bath900 sq ft

24 Winthrop Shore Dr #2, Winthrop, MA 02152

Office space • Hot water heater • Private storage

Property at 600 Shirley St #3, Winthrop, MA 02152, 2 beds, 2 baths

$549,900

2 beds2 baths773 sq ft

600 Shirley St #3, 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

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OPEN SAT, 2:30PM TO 4PMVIDEO TOUR

916 Shirley #1, Winthrop, MA 02152
916 Shirley #1, Winthrop, MA 02152
916 Shirley #1, Winthrop, MA 02152
ABOUT THIS HOME
Cottage Hill, MA Homes for Sale
At 916 Shirley, we redefine coastal luxury living with our exceptional collection of waterfront condos. Immerse yourself in the essence of waterfront living-breathe in the salty ocean air, bask in the warmth of the sun, & let every wave carry you closer to serenity. Here you will find 3 bedrooms, 2.5 bathrooms, 3 private outdoor decks, 3 levels of finished living space, 2 parking spaces, EV Charger, extra flex space in the basement for office or gym. Enjoy Skyline Views & Sunsets on your private primary deck. Our vision is to provide a seamless experience by showcasing exquisitely crafted residences with open-concept living spaces, high-end finishes, and breathtaking waterfront v

$1,200,000

3 beds2.5 baths1,700 sq ft

916 Shirley #1, Winthrop, MA 02152

4,740 sq ft lot • $350 HOA • Car-dependent

876 Shirley #1, Winthrop, MA 02152
876 Shirley #1, Winthrop, MA 02152
876 Shirley #1, Winthrop, MA 02152

$829,999

4 beds2 baths2,000 sq ft

876 Shirley #1, Winthrop, MA 02152

$450 HOA • Car-dependent

Average home prices near Cottage Hill, MA

Cities

Neighborhoods

Logan Airport / Jeffries Point homes for sale
$725,000
Point Shirley homes for sale
Downtown Winthrop homes for sale
$699,900
East Boston homes for sale
$699,000
Beachmont homes for sale
$799,900
Orient Heights homes for sale
$632,000
Harbor View-Orient Heights homes for sale
$679,000
Jeffries Point homes for sale
$725,000
Whinthrop Highlands homes for sale
$749,999

Cottage Hill, MA real estate trends

All Home Types trends in Cottage Hill, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$520,000

-3.7% YoY | Jul 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jul 2025

Growth

% YoY

Cottage Hill, MA

$520,000

-3.7%

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