Whinthrop Highlands, MA homes for sale & real estate

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OPEN SAT, 11AM TO 1PM

72 Sewall Ave, Winthrop, MA 02152
72 Sewall Ave, Winthrop, MA 02152
72 Sewall Ave, Winthrop, MA 02152
ABOUT THIS HOME
Whinthrop Highlands, MA Homes for Sale
Highly desirable location this home is only 16 years old built over its original foundation. this 4-bed, 3.5-bath home spans three levels in Winthrop’s Highlands. The first floor offers an open layout ideal for entertaining, with a spacious kitchen featuring white cabinets and updated countertops flowing into the living and dining rooms. French doors lead to a deck and patio overlooking a large, fenced in backyard. The main suite opens to a private side deck and features a primary bath. Enjoy central air, second-floor laundry, a large basement for storage, a newer furnace and water heater (2022). The top floor offers a ocean views, and there's a hidden beach at the end of the street.

$1,265,000

4 beds3.5 baths2,214 sq ft

72 Sewall Ave, Winthrop, MA 02152

8,487 sq ft lot • Garage • Somewhat walkable

OPEN SAT, 11AM TO 12:30PM

44 Cliff #3, Winthrop, MA 02152
44 Cliff #3, Winthrop, MA 02152
44 Cliff #3, Winthrop, MA 02152
ABOUT THIS HOME
Whinthrop Highlands, 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. Cond

$679,000

3 beds2 baths1,849 sq ft

44 Cliff #3, Winthrop, MA 02152

$440 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
Whinthrop Highlands, MA Homes for Sale
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 right next door. Commuter-friendly locati

$1,400,000

10 beds4 baths4,671 sq ft

45 Highland Ave, Winthrop, MA 02152

5,710 sq ft lot • Very walkable

68-70 Floyd St, Winthrop, MA 02152
68-70 Floyd St, Winthrop, MA 02152
68-70 Floyd St, Winthrop, MA 02152
ABOUT THIS HOME
Whinthrop Highlands, MA Homes for Sale
AMAZING PICTURE POST CARD SETTING FOR THIS BEAUTIFUL HOME IN WINTHROP'S HIGHLANDS LOCATION. .. .. .. .This legal 2 family will appeal to single family Buyers as well. A " younger" home compared to most, this multi-level Contemporary has an open floor plan, eat in kitchen open to a great room with skylights and a slider to the large private yard. The second level has a main suite with private bath and custom walk in closet. There is also another full bath and 2 good size bedrooms. The lower level has a large finished family room, half bath and cedar closet. Unit two has its own private entrance and is perfect for a family member or, is an easy rental with high demand in this curren

$999,900

4 beds3.5 baths3,432 sq ft

68-70 Floyd St, Winthrop, MA 02152

9,001 sq ft lot • Pool • Somewhat walkable

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328-330 Revere St, Winthrop, MA 02152
328-330 Revere St, Winthrop, MA 02152
328-330 Revere St, Winthrop, MA 02152
ABOUT THIS HOME
Whinthrop Highlands, MA Homes for Sale
This property is what the competition see as a "Triple Threat" * TURN KEY * LOCATION & * BIG LOT OF LAND! The first floor's Craftsman style details have had restoration, preserving the stain glass windows, hardwood floors, working wood fireplace, beamed ceilings & built-ins to really embody the character of days gone by. A gas stove with hood vent, & sliders to a deck off the kitchen, makes this space extra special. Generously sized bedrooms & closets with coin laundry are also a part of the perks of this unit. The 2nd floor is vacant and newly renovated. New thermal windows, & scratch proof high grade laminate flooring both with lifetime warranty's

$1,170,000

5 beds2 baths2,151 sq ft

328-330 Revere St, Winthrop, MA 02152

7,959 sq ft lot • Very walkable

Property at 75 Sewall Ave, Winthrop, MA 02152, 3 beds, 2.5 baths

$825,000

3 beds2.5 baths2,112 sq ft

75 Sewall Ave, Winthrop, MA 02152

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OPEN SUN, 12:30PM TO 2PM

500 Governors Dr #9, Winthrop, MA 02152
500 Governors Dr #9, Winthrop, MA 02152
500 Governors Dr #9, Winthrop, MA 02152
ABOUT THIS HOME
Whinthrop Highlands, MA Homes for Sale
Welcome to 500 Governors Drive Unit 9, a spacious and well-maintained 3-bedroom, first-floor condo located in the beautiful coastal town of Winthrop. This unit features a bright and airy open-concept living and dining area, perfect for both relaxing and entertaining. Vinyl flooring runs throughout the entire home, offering a sleek, low-maintenance finish. Set within a well-managed association, residents enjoy peace of mind and a sense of community. Whether you're a first-time buyer, downsizer, or investor, this unit offers comfort, convenience, and value all in one.

$355,000

3 beds1 bath772 sq ft

500 Governors Dr #9, Winthrop, MA 02152

$466 HOA • Community pool • Very walkable

VIDEO TOUR

37-39 Hutchinson St, Winthrop, MA 02152
37-39 Hutchinson St, Winthrop, MA 02152
37-39 Hutchinson St, Winthrop, MA 02152
ABOUT THIS HOME
Whinthrop Highlands, MA Homes for Sale
Endless Potential in Prime Seaside Location – 02152 Welcome to this oversized two-family home located in the highly desirable seaside community of Winthrop, 02152. Perfectly situated on a generous lot, this property offers a rare opportunity for investors, multi-generational living, or owner-occupants looking to customize and create value. Each unit features spacious layouts with room to grow, and the home includes a full unfinished basement—ideal for storage or future expansion. Enjoy the convenience of off-street parking and a private backyard, perfect for outdoor entertaining or quiet relaxation. With its prime location near the ocean, beaches, and all that Winthrop has to of

$899,000

5 beds2 baths2,958 sq ft

37-39 Hutchinson St, Winthrop, MA 02152

5,000 sq ft lot • Very walkable

136 Locust Way, Winthrop, MA 02152
136 Locust Way, Winthrop, MA 02152
136 Locust Way, Winthrop, MA 02152
ABOUT THIS HOME
Whinthrop Highlands, MA Homes for Sale
Well maintained 3 bedroom Colonial just moments from the beach. Large open rooms with lots of natural light. Lots of cabinet space in the super functional kitchen. 1st floor laundry hookups for convenience. 3 full sized bedrooms. Great yard. Nice wrap around porch to enjoy the summer nights. Seller willing to buy down the mortgage rate on this home. PLEASE BOOK SHOWINGS THROUGH SHOWINGTIME.

$624,900

3 beds1 bath1,878 sq ft

136 Locust Way, Winthrop, MA 02152

3,217 sq ft lot • Very walkable

3D WALKTHROUGH

80 Shirley St, Winthrop, MA 02152
80 Shirley St, Winthrop, MA 02152
80 Shirley St, Winthrop, MA 02152
ABOUT THIS HOME
Whinthrop Highlands, MA Homes for Sale
Gorgeous farmhouse revival!!! Coastal vibes flow through this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. Both units boast modern open floor plans. Actual high end finishes throughout for an obvious upscale vibe. Huge kitchens and natural light throughout. Some of the sunniest units you will see. Bathrooms like spas. High ceilings and great flowing layouts that make sense. The convenience of living in East Boston and the blue line nearby, without the congestion and lack of parking. Huge yard and driveway. Brand new heat

$1,100,000

4 beds2 baths2,366 sq ft

80 Shirley St, Winthrop, MA 02152

5,500 sq ft lot • Very walkable

80 Shirley St #1, Winthrop, MA 02152
80 Shirley St #1, Winthrop, MA 02152
80 Shirley St #1, Winthrop, MA 02152
ABOUT THIS HOME
Whinthrop Highlands, MA Homes for Sale
Gorgeous farmhouse revival! Coastal vibes flow throughout this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. The unit boasts a modern open floor plan. Actual high end finishes throughout for an obvious upscale vibe. Huge kitchen and natural light throughout. One of the sunniest units that you will see. High ceilings and a great flowing layout that makes sense. The convenience of living in East Boston and the blue line nearby, without the congestion and lack of parking. Huge yard and driveway. Brand new heating systems, ce

$449,900

1 bed1 bath836 sq ft

80 Shirley St #1, Winthrop, MA 02152

5,500 sq ft lot • $150 HOA • Very walkable

80 Shirley St #2, Winthrop, MA 02152
80 Shirley St #2, Winthrop, MA 02152
80 Shirley St #2, Winthrop, MA 02152
ABOUT THIS HOME
Whinthrop Highlands, MA Homes for Sale
Gorgeous farmhouse revival!!! Coastal vibes flow throughout this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. The unit boasts a modern open floor plan. Actual high end finishes throughout for an obvious upscale vibe. Huge kitchen and natural light throughout. Spa like bathrooms. One of the sunniest units that you will see. High ceilings and a great flowing layout that makes sense. The convenience of living in East Boston and the blue line nearby, without the congestion and lack of parking. Huge yard and driveway. Brand n

$649,900

3 beds2 baths1,252 sq ft

80 Shirley St #2, Winthrop, MA 02152

5,500 sq ft lot • $250 HOA • Very walkable

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

Average home prices near Whinthrop Highlands, MA

Cities

Neighborhoods

Oak Island homes for sale
$569,900
Downtown Revere homes for sale
$739,900
Downtown Winthrop homes for sale
$729,000
East Boston homes for sale
$687,000
Beachmont homes for sale
$799,900
West Revere homes for sale
$675,000
Orient Heights homes for sale
$569,500
Harbor View-Orient Heights homes for sale
$692,000
Jeffries Point homes for sale
$680,000
Crescent Beach homes for sale
$659,000

Whinthrop Highlands, MA real estate trends

All Home Types trends in Whinthrop Highlands, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$655,000

+14.9% YoY | Jun 2025

1 year
3 year
5 year

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

Location

Data

Jun 2025

Growth

% YoY

Whinthrop Highlands, MA

$655,000

+14.9%

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