264 Webster St
BostonMA02128
Luxury Homes for Rent in Winthrop, MA (243 Rentals) Page 2 of 5
The most luxurious Homes in Winthrop with high-end amenities, features, and finishes.
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$2,770
Total Monthly Price
1 Bedroom Apartments Available Mar 27, 2026Total Monthly Price
Base Rent
$2,400
Required Monthly Fees
$370
Total Monthly Price
$2,770
340 Bremen St
340 Bremen StBoston, MA 02128
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188 Chelsea St, Unit 1
188 Chelsea St
BostonMA02128
194 Paris St, Unit 1
194 Paris St
BostonMA02128
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156 Porter St
BostonMA02128
175 Cottage St
ChelseaMA02150
66 Thornton St
RevereMA02151
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
58 Agawam St
RevereMA02151
175 Cottage St
ChelseaMA02150
630 Bennington St, Unit 3
630 Bennington St
BostonMA02128
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198 Chelsea St, Unit 1
198 Chelsea St
BostonMA02128
80 Chelsea St
BostonMA02128
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70 Frankfort St
BostonMA02128
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77 Morris St, Unit 1
77 Morris St
BostonMA02128
119 Lexington St, Unit 3R
119 Lexington St
BostonMA02128
138 Marginal St, Unit 2
138 Marginal St
BostonMA02128
1 Chelsea Ter, Unit 2
1 Chelsea Ter
BostonMA02128
77 Byron St
BostonMA02128
132 Marginal St
BostonMA02128
214-216-216 E Eagle St
BostonMA02128
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$2,850
Plus Fees
3 Bedroom Apartments Available Now151-153 Meridian St.
151-153-153 Meridian StBoston, MA 02128
349 Sumner St, Unit 3
349 Sumner St
BostonMA02128
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156 Chelsea St
BostonMA02128
77 Byron St, Unit 2
77 Byron St
BostonMA02128
75 Morris St, Unit 1
75 Morris St
BostonMA02128
193-195 Chelsea St
BostonMA02128
193-195-195 Chelsea St
BostonMA02128
147 Princeton St, Unit 118-3
147 Princeton St
BostonMA02128
117 Orleans St, Unit 2-bed 1-bath unit 1
117 Orleans St
BostonMA02128
326 Chelsea St
BostonMA02128
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343 Sumner St
BostonMA02128
349 Sumner St, Unit 3
349 Sumner St
BostonMA02128
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173 Trenton St, Unit 1
173 Trenton St
BostonMA02128
249 Lexington St, Unit 9
249 Lexington St
BostonMA02128
249 Lexington St
BostonMA02128
29 Chelsea St
BostonMA02128
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333 Lee Burbank Hwy
RevereMA02151
113 Orleans St, Unit 1
113 Orleans St
BostonMA02128
Winthrop, MA Local Guide
View of Winthrop, Massachusetts from the northeast by Sean 2015 is licensed under Internal
How much does it cost to rent a home in Winthrop?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winthrop 2 Bedroom Homes for Rent | $3,065 | $2,100 | $4,500 |
| Winthrop 3 Bedroom Homes for Rent | $3,622 | $2,800 | $5,500 |
| Winthrop 4 Bedroom Homes for Rent | $3,980 | $3,200 | $4,800 |
| Winthrop 5 Bedroom Homes for Rent | $5,339 | $3,900 | $7,995 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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Frequently Asked Questions about Winthrop
What type of rentals are currently available in Winthrop?
There are currently 626 Apartments for Rent in Winthrop, MA with pricing that ranges from $1,100 to $8,632. There are also 286 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winthrop ranging from $1,500 to $7,995.
What is the current price range for Rental Homes in Winthrop?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winthrop ranges from $1,500 to $7,995 with an average monthly rent of $3,415.
How much are larger Three and Four Bedroom Rentals in Winthrop?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winthrop range from $2,600 to $5,556, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $5,500. Four Bedroom Single-Family rentals are also available starting from $3,200 and Four Bedroom Apartments start at $3,000.
Expert Rental Resources
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.
Helpful Local Expert Guides
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.
A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!
Explore Like a Local: The Insider's Guide to Boston
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Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
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Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips
How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips
Written by: Justin Habersaat
Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!