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Winthrop Highlands Homes for Rent

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  • 50 Cliff Ave Unit 1, Winthrop, MA 02152
    50 Cliff Ave Unit 1, Winthrop, MA 02152
    50 Cliff Ave Unit 1, Winthrop, MA 02152
    /32

    $4,600 per month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Apartment for Rent

    50 Cliff Ave Unit 1, Winthrop, MA 02152

    Step into this stunning luxury 3-bedroom apartment that perfectly blends modern design with serene waterfront living. As you enter, you’re greeted by an open-concept living space bathed in natural light, with floor-to-ceiling windows offering breathtaking water views from nearly every room.The chef-inspired kitchen is outfitted with top-of-the-line stainless steel appliances, sleek quartz

    Agent Photo

    Albeiro Lopera

    United Brokers

    (617) 993-6604

    50 Cliff Ave Unit 1, Winthrop, MA 02152
  • 141 Grovers Ave Unit 141, Winthrop, MA 02152
    141 Grovers Ave Unit 141, Winthrop, MA 02152
    141 Grovers Ave Unit 141, Winthrop, MA 02152
    /23

    $5,500 per month

    • 3 Beds
    • 3 Baths
    • 2,400 Sq Ft
    • Apartment for Rent

    141 Grovers Ave Unit 141, Winthrop, MA 02152

    Winthrop, MA (Winthrop Highlands) Water-Front Luxury 3 Bedrooms, 3 Baths Townhouse For Rent - August 1, 2025; FEATURES: 2400 Square Feet Of Beautiful Living Space; Stainless Steel Appliances (stove/refrigerator/dishwasher/microwave); Granite Counter-tops & Kitchen Island; Elegant Cherry Cabinets; Gleaming Hardwood Floor & Ceramic Tile Floors; Central Heating And Air-Conditioning; Fire Place,

    Agent Photo

    Herman Davis

    Metro North Realty, LLC

    (857) 855-4545

    141 Grovers Ave Unit 141, Winthrop, MA 02152
  • 141 Grovers Ave, Winthrop, MA 02152
    141 Grovers Ave, Winthrop, MA 02152
    141 Grovers Ave, Winthrop, MA 02152
    /20

    $5,500 per month

    • 3 Beds
    • 3 Baths
    • 2,400 Sq Ft
    • Townhouse for Rent

    141 Grovers Ave, Winthrop, MA 02152

    Gorgeous Water-Front Luxury 3 Bedrooms, 3 Baths Townhouse For Rent - Available August 1, 2025FEATURES:2400 Square Feet Of Beautiful Living SpaceStainless Steel Appliances (stove/refrigerator/dishwasher/microwave)Granite Counter-tops & Kitchen IslandElegant Cherry Cabinets Gleaming Hardwood Floor & Ceramic Tile FloorsCentral Heating And Air-ConditioningFire

    141 Grovers Ave, Winthrop, MA 02152
  • 1 Pond St Unit 2F, Winthrop, MA 02152
    1 Pond St Unit 2F, Winthrop, MA 02152
    1 Pond St Unit 2F, Winthrop, MA 02152
    /12

    $2,300 per month

    • 1 Bed
    • 1 Bath
    • 850 Sq Ft
    • Apartment for Rent

    1 Pond St Unit 2F, Winthrop, MA 02152

    **AVAILABLE NOW** This is a spacious 1 bedroom/ 1 bath apartment with a private balcony overlooking the beautifully kept grounds of Fort Heath! It is recently remodeled with new laminate flooring throughout as well as new countertops in the kitchen. The unit includes a gas stove, dishwasher and refrigerator. It boasts new kitchen cabinets and a new vanity in bathroom as well as a walk-in closet

    James Polino Compass

    1 Pond St Unit 2F, Winthrop, MA 02152
  • 82 Temple Ave Unit 1, Winthrop, MA 02152
    82 Temple Ave Unit 1, Winthrop, MA 02152
    82 Temple Ave Unit 1, Winthrop, MA 02152
    /8

    $1,500 per month

    • 1 Bed
    • 1 Bath
    • 1,300 Sq Ft
    • Condo for Rent

    82 Temple Ave Unit 1, Winthrop, MA 02152

    1 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

    82 Temple Ave Unit 1, Winthrop, MA 02152
  • 1 Pond St Unit 3K, Winthrop, MA 02152
    1 Pond St Unit 3K, Winthrop, MA 02152
    1 Pond St Unit 3K, Winthrop, MA 02152
    /12

    $2,300 per month

    • 1 Bed
    • 1 Bath
    • 850 Sq Ft
    • Apartment for Rent

    1 Pond St Unit 3K, Winthrop, MA 02152

    **AVAILABLE NOW** This is a spacious 1 bedroom/ 1 bath apartment with a private balcony overlooking the beautifully kept grounds of Fort Heath! It is recently remodeled with new laminate flooring throughout as well as new countertops in the kitchen. The unit includes a gas stove, dishwasher and refrigerator. It boasts new kitchen cabinets and a new vanity in bathroom as well as a walk-in closet

    James Polino Compass

    1 Pond St Unit 3K, Winthrop, MA 02152
  • 108 Quincy Ave Unit 3, Winthrop, MA 02152
    108 Quincy Ave Unit 3, Winthrop, MA 02152
    108 Quincy Ave Unit 3, Winthrop, MA 02152
    /26

    $2,800 per month

    • 2 Beds
    • 1 Bath
    • 9,999 Sq Ft
    • Condo for Rent

    108 Quincy Ave Unit 3, Winthrop, MA 02152

    2 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

    108 Quincy Ave Unit 3, Winthrop, MA 02152
  • 158 Highland Ave Unit 1, Winthrop, MA 02152
    158 Highland Ave Unit 1, Winthrop, MA 02152
    158 Highland Ave Unit 1, Winthrop, MA 02152
    /15

    $3,400 per month

    • 2 Beds
    • 1 Bath
    • 1,376 Sq Ft
    • Apartment for Rent

    158 Highland Ave Unit 1, Winthrop, MA 02152

    Available now, this stunning apartment in desirable Winthrop Highlands is not your average rental. Featuring high ceilings and hardwood floors throughout, the home offers a spacious and elegant layout with a formal living room, formal dining room, and a sunroom that’s perfect as a home office. The fully applianced granite kitchen includes stainless steel appliances, ideal for both everyday

    Erica Gore Century 21 Seaport

    158 Highland Ave Unit 1, Winthrop, MA 02152
  • 45 Highland Ave Unit 3, Winthrop, MA 02152
    45 Highland Ave Unit 3, Winthrop, MA 02152
    45 Highland Ave Unit 3, Winthrop, MA 02152
    /20

    $3,900 per month

    • 5 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Apartment for Rent

    45 Highland Ave Unit 3, Winthrop, MA 02152

    Spanning the 2nd and 3rd floors, this enormous 5-bedroom, 2-bathroom unit features 2 porches (1 in the front, 1 in the back), fire place, dishwasher, paved off street parking in the driveway and much more. The property directly abuts Crest Ave Park, offering green space right next door. Commuter-friendly location with easy access to Boston and points North/South via major routes. Public transit

    Sarah Strangie Keller Williams Realty Boston-Metro | Back Bay

    45 Highland Ave Unit 3, Winthrop, MA 02152
Massachusetts Suffolk County Winthrop Winthrop Highlands

Homes for Rent in Winthrop Highlands, Winthrop

Why Live in Winthrop Highlands
Winthrop Highlands, a picturesque neighborhood surrounded by water on three sides, is known for its stunning natural beauty and close-knit community. Residents enjoy breathtaking sunrises and sunsets over the Atlantic Ocean, with opportunities to see the full moon rise over the horizon. The area is ideal for outdoor enthusiasts, offering activities such as boating, fishing, surfing, and jogging. Halford Beach and Highlands Beach provide convenient water access, while Fort Heath Park on Grovers Cliff is a popular spot for dog walking and occasional concerts. The neighborhood also features the Pond Street Playground and the John Joseph Kilmartin Pathway for recreational activities. Winthrop Highlands is characterized by its historic single-family homes, including Cape Cods, colonials, and the occasional Victorian, most of which were built around the turn of the 20th century. The neighborhood's streets are peaceful and well-established, with slightly larger lots compared to other parts of town. The local restaurant scene is vibrant, with notable spots like the Winthrop Arms Hotel and Restaurant, Jac’s Café, Antique Table Restaurant, and Bridges Nepali Cuisine. Families in the area benefit from highly rated schools, including William P. Gorman Fort Banks Elementary School, Winthrop Middle School, and Winthrop High School, all recognized for their strong academic performance. The neighborhood's proximity to Downtown Boston, just 10 miles away via U.S. Route 145, and the ferry service less than 2 miles away, make commuting convenient. Additionally, Boston Logan International Airport is just over 5 miles from the neighborhood. With its low crime risk compared to the national average, Winthrop Highlands offers a serene and engaging environment for its residents.
Learn more about living in Winthrop Highlands

Frequently Asked Questions

What are the most popular neighborhoods for renters near Winthrop Highlands?
The most popular neighborhoods for renters near Winthrop Highlands are Downtown Winthrop, Winthrop Beach, Beachmont, Cottage Hill and Harbor View-Orient Heights.
What are the most popular zip codes for renters near Winthrop Highlands?
The most popular zip codes for renters near Winthrop Highlands are 02152, 02151, 02128, 02150 and 01908.
How to Rent a Home

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