Luxury Homes for Rent in Winthrop Highlands Neighborhood of Winthrop, MA (78 Rentals)

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The most luxurious Homes in the Winthrop Highlands area of Winthrop with high-end amenities, features, and finishes.

property at 5 Fremont St

5 Fremont St, Unit 106

5 Fremont St
WinthropMA02152
property at 76 Fremont St

76 Fremont St, Unit #2

76 Fremont St
WinthropMA02152

Boston's Best Affordable Neighborhoods

Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead

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property at 115 Winthrop St

115 Winthrop St

WinthropMA02152
property at 90 Gladstone St

90 Gladstone St, Unit 1

90 Gladstone St
BostonMA02128
property at 90 Gladstone St

90 Gladstone St, Unit 1

90 Gladstone St
BostonMA02128
property at 90 Gladstone St

90 Gladstone St, Unit 1

90 Gladstone St
BostonMA02128
property at 215 Leyden St

215 Leyden St, Unit 1

215 Leyden St
BostonMA02128
property at 48 Winthrop Ave

48 Winthrop Ave, Unit 1

48 Winthrop Ave
RevereMA02151
property at 24 Cummings Ave

24 Cummings Ave, Unit 1

24 Cummings Ave
RevereMA02151
property at 184 Gladstone St

184 Gladstone St

BostonMA02128
property at 14 Leverett Ave

14 Leverett Ave

BostonMA02128
property at 96 Florence Ave

96 Florence Ave, Unit 2

96 Florence Ave
RevereMA02151
property at 82 Gladstone St

82 Gladstone St, Unit 1

82 Gladstone St
BostonMA02128
property at 72 Thornton St

72 Thornton St, Unit 2

72 Thornton St
RevereMA02151
property at 112 Lynnway

112 Lynnway, Unit 1

112 Lynnway
RevereMA02151
property at 39 Winthrop Ave

39 Winthrop Ave, Unit 1

39 Winthrop Ave
RevereMA02151
property at 10 Ocean Ave

10 Ocean Ave, Unit 204

10 Ocean Ave
RevereMA02151
property at 500 Beach St

500 Beach St, Unit 1

500 Beach St
RevereMA02151
Showing Results 1-50, Page 1 of 2

Winthrop Highlands, Winthrop, MA Local Guide

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Frequently Asked Questions about Winthrop Highlands

What type of rentals are currently available in Winthrop Highlands?

There are currently 330 Apartments for Rent in Winthrop Highlands, MA with pricing that ranges from $1,155 to $8,223. There are also 91 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winthrop Highlands ranging from $1,900 to $5,200.

What is the current price range for Rental Homes in Winthrop Highlands?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Winthrop Highlands ranges from $1,900 to $5,200 with an average monthly rent of $3,267.

How much are larger Three and Four Bedroom Rentals in Winthrop Highlands?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Winthrop Highlands range from $2,600 to $5,406, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $3,700. Four Bedroom Single-Family rentals are also available starting from $3,700 and Four Bedroom Apartments start at $3,700.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

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The 10 Best Affordable Neighborhoods in Boston, MA

Written by: Amelia Ramstead

Boston is known for its exciting combination of early American history and modern high-tech universities and employers.

decorative image for Renting Smart: Lease Basics Every Renter Needs article

Renting Smart: Lease Basics Every Renter Needs

Written by: Christine Leonard, Esq.

Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

decorative image for Battling the Butts: Your Guide to the Reality of Smoke-Free Renting article

Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

Written by: Andrea Lee Negroni, JD

While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.

decorative image for Understanding Amenity Fees: Know Where You Might Be Able to Save Money article

Understanding Amenity Fees: Know Where You Might Be Able to Save Money

Written by: Amber Kanuckel

With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.