Luxury Homes for Rent in Winthrop, MA (247 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

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

property at 439 Winthrop St

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Now

439 Winthrop St, Unit 1

439 Winthrop St
WinthropMA02152
property at 92 Winthrop Shore Dr

$2,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,750

Total Monthly Price
$2,750

2 Bedroom, 1 Bath Condo for Rent

Available Now

92 Winthrop Shore Dr, Unit 2

92 Winthrop Shore Dr
WinthropMA02152
property at 5 Fremont St

$3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

2 Bedroom, 2 Bath Condo for Rent

Available Now

5 Fremont St, Unit 106

5 Fremont St
WinthropMA02152
property at 1 Seal Harbor Rd

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

2 Bedroom, 2 Bath Condo for Rent

Available Now

1 Seal Harbor Rd

WinthropMA02152
property at 23 Sachem St

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 1.5 Bath Home for Rent

Available Now

23 Sachem St

WinthropMA02152
property at 51 Cutler St

$3,300

Total Monthly Price

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

2 Bedroom, 2 Bath Condo for Rent

Available Now

51 Cutler St

WinthropMA02152
property at 249 Winthrop Shore Dr

$3,350

Total Monthly Price

Total Monthly Price

Base Rent
$3,350

Total Monthly Price
$3,350

2 Bedroom, 1 Bath Condo for Rent

Available Now

249 Winthrop Shore Dr

WinthropMA02152
property at 85 Beach Rd

$3,400

Total Monthly Price4 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

3 Bedroom, 1.5 Bath Home for Rent

Available Now

85 Beach Rd

WinthropMA02152
property at 40 Cottage Park Rd

$3,500

Plus Fees12 Month Lease Term

3 Bedroom, 1 Bath Condo for Rent

Available Now

40 Cottage Park Rd

WinthropMA02152

Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street

Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.

property at 175 Somerset Ave

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Townhome for Rent

Available Now

175 Somerset Ave

WinthropMA02152
property at 143 Grovers Ave

$5,000

Total Monthly Price

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

3 Bedroom, 3 Bath Townhome for Rent

Available Now

143 Grovers Ave

WinthropMA02152
property at 141 Grovers Ave

$5,500

Total Monthly Price

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

3 Bedroom, 3 Bath Townhome for Rent

Available Now

141 Grovers Ave

WinthropMA02152
property at 141 Grovers Ave

$5,500

Plus Fees

3 Bedroom, 3 Bath Home for Rent

Available Now

141 Grovers Ave

WinthropMA02152
property at 104 Princeton St

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 1 Bath Condo for Rent

Available Now

104 Princeton St, Unit 3

104 Princeton St
BostonMA02128
property at 125 London St

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

1 Bedroom, 1 Bath Condo for Rent

Available Now

125 London St, Unit 3

125 London St
BostonMA02128
property at 75 Putnam St

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 1 Bath Condo for Rent

Available Now

75 Putnam St, Unit 1

75 Putnam St
BostonMA02128
property at 55 Chelsea St

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

1 Bedroom, 1 Bath Condo for Rent

Available Now

55 Chelsea St, Unit 3B

55 Chelsea St
BostonMA02128
property at 238 Everett St

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 1 Bath Condo for Rent

Available Now

238 Everett St, Unit 1

238 Everett St
BostonMA02128

Explore Like a Local: The Insider's Guide to Boston

Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.

property at 4 Elbow St

$2,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

2 Bedroom, 1 Bath Condo for Rent

Available Now

4 Elbow St, Unit 1

4 Elbow St
BostonMA02128
property at 15 Walley St

$2,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

1 Bedroom, 1 Bath Condo for Rent

Available Now

15 Walley St, Unit 206

15 Walley St
BostonMA02128
property at 530 Beach St

$2,550

Plus Fees

2 Bedroom, 1 Bath Condo for Rent

Available Now

530 Beach St

RevereMA02151
property at 45 Morris St

$2,575

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,575

Total Monthly Price
$2,575

2 Bedroom, 1 Bath Condo for Rent

Available Now

45 Morris St, Unit 2-bed unit2

45 Morris St
BostonMA02128
property at 200 London St

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Now

200 London St, Unit 2

200 London St
BostonMA02128
property at 88 Gerrish Ave

$2,600

Plus Fees12 Month Lease Term

2 Bedroom, 1 Bath Condo for Rent

Available Now

88 Gerrish Ave, Unit 214

88 Gerrish Ave
ChelseaMA02150
property at 319 Bennington St

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Now

319 Bennington St, Unit 1a

319 Bennington St
BostonMA02128
property at 202 Maverick St

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Now

202 Maverick St, Unit 2R

202 Maverick St
BostonMA02128

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

property at 55 Chelsea St

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

1 Bedroom, 1 Bath Condo for Rent

Available Now

55 Chelsea St, Unit 3B

55 Chelsea St
BostonMA02128
property at 52 Brooks St

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Now

52 Brooks St, Unit 1

52 Brooks St
BostonMA02128
property at 175 Cottage St

$2,600 - $2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

1 To 2 Bedroom Rentals

Available Now

175 Cottage St

ChelseaMA02150
property at 135 Eutaw St

$2,625

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,625

Total Monthly Price
$2,625

1 Bedroom, 1 Bath Condo for Rent

Available Now

135 Eutaw St, Unit 2

135 Eutaw St
BostonMA02128
property at 108 Byron St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Now

108 Byron St, Unit A

108 Byron St
BostonMA02128
property at 231 Maverick St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Now

231 Maverick St, Unit 2L

231 Maverick St
BostonMA02128
property at 26 Chelsea St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

1 Bedroom, 1 Bath Condo for Rent

Available Now

26 Chelsea St, Unit 3

26 Chelsea St
BostonMA02128
property at 26 Chelsea St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

1 Bedroom, 1 Bath Condo for Rent

Available Now

26 Chelsea St, Unit 2

26 Chelsea St
BostonMA02128

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

property at 153 Winthrop Pkwy

$2,650

Total Monthly Price

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Townhome for Rent

Available Jan 1, 2026

153 Winthrop Pkwy

RevereMA02151
property at 42 Everett St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Now

42 Everett St, Unit 2

42 Everett St
BostonMA02128
property at 1030 Bennington St

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

2 Bedroom, 1 Bath Condo for Rent

Available Now

1030 Bennington St, Unit 5

1030 Bennington St
BostonMA02128
property at 1030 Bennington St

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

2 Bedroom, 1 Bath Condo for Rent

Available Now

1030 Bennington St, Unit 5

1030 Bennington St
BostonMA02128
property at 1030 Bennington St

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

2 Bedroom, 1 Bath Condo for Rent

Available Now

1030 Bennington St, Unit 5

1030 Bennington St
BostonMA02128
property at 1030 Bennington St

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

2 Bedroom, 1 Bath Condo for Rent

Available Now

1030 Bennington St, Unit 5

1030 Bennington St
BostonMA02128
property at 264 Webster St

$2,750

Total Monthly Price

Total Monthly Price

Base Rent
$2,750

Total Monthly Price
$2,750

2 Bedroom, 1 Bath Condo for Rent

Available Now

264 Webster St

BostonMA02128

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

Winthrop, MA Local Guide

Boston Neighborhood Guide: Living Near UMass, MGH, and State Street

Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.

Read Article
Decorative image

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

Read Article
Decorative image

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

Read Article
Decorative image

Top Neighborhoods Near Boston Colleges and Universities

Learn About the Best Neighborhoods to Rent Near College Campuses in Boston, MA | Find Boston Off-Campus Student Housing at ApartmentHomeLiving.com

Read Article
Decorative image

Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

decorative image of people with a giant lease agreement

Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Winthrop, MA Rentals by Map

View Map
Winthrop, MA Apartments Map
View Map
Winthrop, MA Rental Homes Map

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 $9,095. There are also 289 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 $3,442.

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 $5,406, 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

decorative image for The 10 Best Affordable Neighborhoods in Boston, MA article

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 A Local Experts Guide to the Top Boston Neighborhoods for College Renters article

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!

decorative image for Explore Like a Local: The Insider's Guide to Boston article

Explore Like a Local: The Insider's Guide to Boston

Written by: Amelia Ramstead

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.

decorative image for Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street article

Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street

Written by: Amelia Ramstead

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

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

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.

decorative image for Apartment Common Area Rules: What Renters Need to Know article

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.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.