Downtown Winthrop, MA homes for sale & real estate

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17 Edgehill Rd, Winthrop, MA 02152
17 Edgehill Rd, Winthrop, MA 02152
17 Edgehill Rd, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Welcome home to 17 Edgehill Road! Nestled in a desirable waterfront community, this spacious single-family is located steps from the harbor & home to some of the most incredible sunset views at Donovan's Beach! Along with being a shoreline neighborhood, Edgehill is known for its charming surroundings next to the lovely Ingleside Park. Here you'll find the kind of space & living that encompasses spending time together. Gather on the1st floor with a large enclosed porch, roomy foyer, bright & sunny kitchen, flexible open living & dining room, & sunroom overlooking your backyard oasis with Gunite pool. Upstairs is 4 bedrooms, full bath, & walk up attic access.

$849,900

5 beds3 baths2,114 sq ft

17 Edgehill Rd, Winthrop, MA 02152

5,027 sq ft lot • Pool • Very walkable

OPEN SAT, 11AM TO 12:30PM

123 Buchanan St, Winthrop, MA 02152
123 Buchanan St, Winthrop, MA 02152
123 Buchanan St, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Step back in time, a stately 19th-century home ready to be restored and reimagined. This 4-bedroom, 1.5-bath is rich with character—featuring original beamed ceilings, ornamental exterior wood trim, and timeless architectural details that set the stage for a stunning transformation. Located near Winthrop Golf Club, High School, and the coastal beauty of Boston’s shoreline, this home offers a rare opportunity for commuters and history lovers alike. Enjoy the charm of small-town living with easy access to the city—a perfect choice for those priced out of Boston but still craving its energy and culture. Inside, the home offers a true canvas of preserved historical features aw

$588,888

4 beds1.5 baths1,785 sq ft

123 Buchanan St, Winthrop, MA 02152

5,053 sq ft lot • Very walkable

OPEN THU, 4PM TO 6PM

26 Enfield Rd, Winthrop, MA 02152
26 Enfield Rd, Winthrop, MA 02152
26 Enfield Rd, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Charming two-family in desirable area of Winthrop. Steps away from Ingleside Park's playground, roller hockey court and baseball field. The restaurants of Winthrop's center are close proximity as well. Great opportunity on one of the nicest streets in Winthrop.

$849,900

5 beds2 baths2,494 sq ft

26 Enfield Rd, Winthrop, MA 02152

5,227 sq ft lot • 2 garage spots • Very walkable

OPEN SUN, 11AM TO 12:30PM

56 Main St, Winthrop, MA 02152
56 Main St, Winthrop, MA 02152
56 Main St, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
OPPORTUNITY KNOCKS. .. .. .. Two family with large yard located right on the bus line with a very short ride to the T to Boston. There are 6 off street parking spaces! The home was gutted in 2001. The owner's unit is on the second and third floors with an open floor plan and loads of natural lighting. It contains a living room, dining area, kitchen, bath and bedroom on the second floor and a sprawling master bedroom on the third floor. There are Boston skyline and marina views from the third floor master bedroom. The owner's unit has a very nice ambiance to it. The first floor unit consists of a living room, kitchen, bath and two bedrooms. There are separate utilities with gas heat. NEXT SH

$799,900

4 beds2 baths2,103 sq ft

56 Main St, Winthrop, MA 02152

6,051 sq ft lot • Somewhat walkable

OPEN THU, 5PM TO 6:30PM

10 Somerset #201, Winthrop, MA 02152
10 Somerset #201, Winthrop, MA 02152
10 Somerset #201, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
The Somerset – Winthrop Center’s Premier Boutique Condo Living by the Sea! This thoughtfully curated collection of 29 modern residences includes studio, 1BR, 1+, and 2BR layouts , each designed with a clean, coastal aesthetic and high-quality finishes. Inside, open-concept floor plans, quartz countertops, stainless steel appliances, central A/C, and sleek modern design. Most homes include garage parking, and select units feature private decks, perfect for enjoying the ocean breeze. The building itself offers convenient amenities like an elevator, fitness center, and a welcoming common lounge—ideal for working remotely or catching up with neighbors over coffee. Moments from

$663,609

2 beds2 baths1,036 sq ft

10 Somerset #201, Winthrop, MA 02152

$466 HOA • Very walkable

Property at 19 Banks St, Winthrop, MA 02152, 3 beds, 1 bath

$735,000

3 beds1 bath1,269 sq ft

19 Banks St, Winthrop, MA 02152

Property at 60 Waldemar Ave, Winthrop, MA 02152, 3 beds, 1 bath

$729,000

3 beds1 bath1,548 sq ft

60 Waldemar Ave, Winthrop, MA 02152

Property at 143 Morton St, Winthrop, MA 02152, 4 beds, 2.5 baths

$825,000

4 beds2.5 baths2,447 sq ft

143 Morton St, Winthrop, MA 02152

Property at 35 Somerset Ave #6, Winthrop, MA 02152, 2 beds, 2 baths

$560,000

2 beds2 baths823 sq ft

35 Somerset Ave #6, Winthrop, MA 02152

Property at 136 Locust Way, Winthrop, MA 02152, 3 beds, 1 bath

$654,900

3 beds1 bath1,878 sq ft

136 Locust Way, Winthrop, MA 02152

Property at 80 Shirley St, Winthrop, MA 02152, 4 beds, 2 baths

$1,100,000

4 beds2 baths2,366 sq ft

80 Shirley St, Winthrop, MA 02152

Property at 80 Shirley St #1, Winthrop, MA 02152, 1 bed, 1 bath

$449,900

1 bed1 bath836 sq ft

80 Shirley St #1, Winthrop, MA 02152

Property at 80 Shirley St #2, Winthrop, MA 02152, 3 beds, 2 baths

$649,900

3 beds2 baths1,252 sq ft

80 Shirley St #2, Winthrop, MA 02152

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OPEN THU, 5:30PM TO 7:30PM

44 Cliff #3, Winthrop, MA 02152
44 Cliff #3, Winthrop, MA 02152
44 Cliff #3, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Welcome to this expansive 1,850 sq ft condo that lives like a single-family home, perfectly perched in the highly desirable Winthrop Highlands. Enjoy breathtaking panoramic ocean views from not one, but two private decks. Inside, you're greeted by sun-drenched spaces, soaring ceilings, and a wide open floor plan that makes entertaining effortless. The modern eat-in kitchen features direct access to a large fenced-in yard, perfect for pets, gardening, or outdoor relaxation. The flexible second floor offers endless possibilities — use it as a spacious family room and guest suite with full bath, or transform it into a luxurious primary retreat with a walk-in closet and ensuite bath. Addi

$679,000

3 beds2 baths1,849 sq ft

44 Cliff #3, Winthrop, MA 02152

$440 HOA • Somewhat walkable

148 Winthrop Shore Dr #5, Winthrop, MA 02152
148 Winthrop Shore Dr #5, Winthrop, MA 02152
148 Winthrop Shore Dr #5, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Welcome to your slice of coastal paradise just outside of Boston. Nestled in the quaint seaside town of Winthrop, this stunning condo offers an unparalleled living experience with exceptional water views. Step inside to discover a meticulously designed space, with an open-concept layout that seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere flooded with natural light and picturesque vistas of the shimmering waterfront. 02152 is conveniently located just outside of Boston, this condo's location offers easy access to the city's amenities while providing a peaceful escape from the hustle and bustle.

$679,000

2 beds2 baths971 sq ft

148 Winthrop Shore Dr #5, Winthrop, MA 02152

$290 HOA • Somewhat walkable

92 Winthrop Shore Dr #2, Winthrop, MA 02152
92 Winthrop Shore Dr #2, Winthrop, MA 02152
92 Winthrop Shore Dr #2, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
This bright and sunny second-floor unit offers optimal ocean and sunrise views. Featuring three bedrooms and hardwood floors throughout, the condo includes a private deck off the main bedroom and a rear deck off the kitchen—perfect for soaking in the morning light and sea breeze. Additional highlights include deeded parking, basement storage and in-unit laundry. Ideally located just 15 minutes from downtown Boston and Logan Airport, with easy access by car, ferry, or the Blue Line, this home offers the perfect blend of comfort, convenience, and coastal charm. Pets are welcome!

$449,000

3 beds1 bath1,245 sq ft

92 Winthrop Shore Dr #2, Winthrop, MA 02152

$375 HOA • Somewhat walkable

3D WALKTHROUGH

45 Highland Ave, Winthrop, MA 02152
45 Highland Ave, Winthrop, MA 02152
45 Highland Ave, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
* * * OPEN HOUSE SAT 12-1:30pm * * * Incredible investment opportunity in the heart of the Highlands! This oversized 3-family property is has been generating strong income with potential for more. One unit is available for an owner occupant or savvy investor looking to maximize cashflow. Walk-out ground level 2-bedroom apartment. First-floor 2-bedroom unit with an additional office, living room, and dining room. Owner’s unit, spanning the 2nd and 3rd floors, this enormous 5-bedroom, 2-bathroom unit can be delivered vacant for owner occupancy or new tenants. Enjoy a paved driveway with ample off-street parking. The property directly abuts Crest Ave Park, offering green space

$1,400,000

10 beds4 baths4,671 sq ft

45 Highland Ave, Winthrop, MA 02152

5,710 sq ft lot • Very walkable

3D WALKTHROUGH

235 Washington Ave #6, Winthrop, MA 02152
235 Washington Ave #6, Winthrop, MA 02152
235 Washington Ave #6, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
WELCOME HOME TO THE WINTHROP CHAMBERS CONDOMINIUM. Penthouse level - 2 bed, 1 bath unit with open floor plan. The views are incredible, whether it be of Lewis Lake and/or the Harbor/City, you will not be disappointed. There are coin operated washer/dryers in the building as well as a storage closet. The condo fee includes heat and hot water and this unit controls its own heat. Enjoy the back patio which is set up with high top table/chairs, gas grills for your use and your very own private beach. Parking is nearby at the Municipal lot. You are steps to the bus line which takes you directly to the Blue Line. Seasonal ferry is a few minute walk. Lots of great restaurants, walking trails and s

$375,000

2 beds1 bath860 sq ft

235 Washington Ave #6, Winthrop, MA 02152

$429 HOA • Somewhat walkable

57 Cutler St, Winthrop, MA 02152
57 Cutler St, Winthrop, MA 02152
57 Cutler St, Winthrop, MA 02152
ABOUT THIS HOME
Downtown Winthrop, MA Homes for Sale
Have you heard the waves crashing from 57 Cutler Street? Sitting just one home back from the ocean, this tastefully updated 3 bed/2 bath is ready for the next lucky owners to call it home. With many updates recently completed (interior paint, upgraded back deck, dishwasher, refinished hardwoods etc. ) all you have to do is unpack your boxes & live your best life oceanside. Kick off your shoes in the mudroom and experience the calm of an open layout living area made for relaxing or entertaining. The eat-in kitchen perfectly situated in the back of the home is fully renovated with a seaside view from your kitchen sink. Off the kitchen, head out onto the back deck & yard- great for

$805,000

3 beds2 baths1,750 sq ft

57 Cutler St, Winthrop, MA 02152

2,600 sq ft lot • Somewhat walkable

Property at 328-330 Revere St, Winthrop, MA 02152, 5 beds, 2 baths

$1,170,000

5 beds2 baths2,151 sq ft

328-330 Revere St, Winthrop, MA 02152

Property at 247 Washington Ave #9, Winthrop, MA 02152, 2 beds, 2 baths

$520,000

2 beds2 baths1,116 sq ft

247 Washington Ave #9, Winthrop, MA 02152

Property at 5 Pearl Ave #2, Winthrop, MA 02152, 2 beds, 1 bath

$449,900

2 beds1 bath812 sq ft

5 Pearl Ave #2, Winthrop, MA 02152

Property at 10 Somerset #405, Winthrop, MA 02152, 1 bed, 1 bath

$551,633

1 bed1 bath683 sq ft

10 Somerset #405, Winthrop, MA 02152

Property at 230 Crescent Ave, Revere, MA 02151, 5 beds, 2 baths

$899,000

5 beds2 baths2,154 sq ft

230 Crescent Ave, Revere, MA 02151

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 35 Somerset Unit 5A, Winthrop, MA 02152, 2 beds, 2 baths

$599,000

2 beds2 baths969 sq ft

35 Somerset Unit 5A, Winthrop, MA 02152

Property at 162 Shirley, Winthrop, MA 02152, 3 beds, 2 baths

$699,000

3 beds2 baths1,413 sq ft

162 Shirley, Winthrop, MA 02152

Property at 25 Pearl Ave, Revere, MA 02151, 3 beds, 1 bath

$579,000

3 beds1 bath1,052 sq ft

25 Pearl Ave, Revere, MA 02151

Property at 5 Waveway Ave, Winthrop, MA 02152, 6 beds, 6 baths

$1,700,000

6 beds6 baths4,122 sq ft

5 Waveway 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 12 Sewall Ave #3, Winthrop, MA 02152, 1 bed, 1 bath

$419,000

1 bed1 bath742 sq ft

12 Sewall Ave #3, Winthrop, MA 02152

Property at 12 Sewall Ave #2, Winthrop, MA 02152, 2 beds, 2 baths

$539,000

2 beds2 baths825 sq ft

12 Sewall Ave #2, Winthrop, MA 02152

Property at 43 Loring Rd, Winthrop, MA 02152, 3 beds, 1.5 baths

$949,000

3 beds1.5 baths1,900 sq ft

43 Loring Rd, Winthrop, MA 02152

Average home prices near Downtown Winthrop, MA

Cities

Neighborhoods

Downtown Revere homes for sale
$704,900
Belingham Square homes for sale
$507,000
East Boston homes for sale
$687,000
Beachmont homes for sale
$799,900
West Revere homes for sale
$687,450
Orient Heights homes for sale
$564,000
Jeffries Point homes for sale
$749,500
Crescent Beach homes for sale
$614,500
D Street-West Broadway homes for sale
$1,399,000
Whinthrop Highlands homes for sale
$689,950

Downtown Winthrop, MA real estate trends

All Home Types trends in Downtown Winthrop, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$705,000

-10.7% YoY | May 2025

1 year
3 year
5 year

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

Location

Data

May 2025

Growth

% YoY

Downtown Winthrop, MA

$705,000

-10.7%

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