Luxury Homes for Rent in Cottage Hill Neighborhood of Winthrop, MA (45 Rentals)

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

property at 5 Fremont St

$2,500 - $3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500 - $3,200

Total Monthly Price
$2,500 - $3,200

1 To 2 Bedroom Condos for Rent

Available Now

5 Fremont St

WinthropMA02152
property at 600 Shirley St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

1 Bedroom, 2 Bath Condo for Rent

Available Now

600 Shirley St, Unit 1

600 Shirley 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 400 Governors Dr

$2,700

Total Monthly Price

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

2 Bedroom, 1 Bath Condo for Rent

Available Now

400 Governors Dr

WinthropMA02152
property at 235 Washington Ave

$2,875

Total Monthly Price

Total Monthly Price

Base Rent
$2,875

Total Monthly Price
$2,875

2 Bedroom, 1 Bath Condo for Rent

Available Now

235 Washington Ave

WinthropMA02152
property at 63 Coral Ave

$3,000

Total Monthly Price

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

3 Bedroom, 1 Bath Condo for Rent

Available Now

63 Coral Ave

WinthropMA02152

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property at 61 Coral Ave

$3,000

Total Monthly Price

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

3 Bedroom, 1 Bath Condo for Rent

Available Now

61 Coral Ave

WinthropMA02152
property at 35 Perkins St

$3,000

Total Monthly Price

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

35 Perkins St

WinthropMA02152
property at 585 Shirley St

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 2 Bath Condo for Rent

Available Now

585 Shirley St

WinthropMA02152
property at 50 Trident Ave

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Condo for Rent

Available Now

50 Trident Ave

WinthropMA02152
property at 36 Sturgis St

$3,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

3 Bedroom, 2 Bath Condo for Rent

Available Now

36 Sturgis St

WinthropMA02152
property at 27 Bowdoin St

$4,000

Total Monthly Price

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

3 Bedroom, 2 Bath Home for Rent

Available Now

27 Bowdoin St

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 Condo for Rent

Available Now

141 Grovers Ave

WinthropMA02152
property at 170 Cliff Ave

$6,000

Total Monthly Price

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

3 Bedroom, 3.5 Bath Townhome for Rent

Available Now

170 Cliff Ave

WinthropMA02152
property at 38 Hawthorn Ave

$3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 1 Bath Condo for Rent

Available Now

38 Hawthorn Ave, Unit 1

38 Hawthorn Ave
WinthropMA02152

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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 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 20 Bradstreet 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 Home for Rent

Available Now

20 Bradstreet Ave

RevereMA02151
property at 1 Orient Ave

$3,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

4 Bedroom, 1 Bath Condo for Rent

Available Sep 1

1 Orient Ave, Unit 2

1 Orient Ave
BostonMA02128
property at 31 Faywood Ave

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

31 Faywood Ave, Unit 3

31 Faywood Ave
BostonMA02128
property at 90 Gladstone St

$4,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

4 Bedroom, 2 Bath Condo for Rent

Available Now

90 Gladstone St, Unit 1

90 Gladstone St
BostonMA02128
property at 103 Saint Andrew Rd

$4,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300

4 Bedroom, 2 Bath Condo for Rent

Available Now

103 Saint Andrew Rd, Unit 1

103 Saint Andrew Rd
BostonMA02128
property at 77 Faywood Ave

$5,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,100

Total Monthly Price
$5,100

4 Bedroom, 2.5 Bath Home for Rent

Available Sep 1

77 Faywood Ave

BostonMA02128

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property at 11 Walley St

$2,795 - $4,200

Total Monthly Price

Total Monthly Price

Base Rent
$2,795

Total Monthly Price
$2,795

1 To 3 Bedroom Rentals

Available Now

11 Walley St

BostonMA02128
property at 1129 Saratoga St

$2,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,850

Total Monthly Price
$2,850

2 Bedroom, 1 Bath Townhome for Rent

Available Now

1129 Saratoga St

BostonMA02128
property at 1008 Bennington St

$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

1008 Bennington St

BostonMA02128
property at 73 Barnes Ave

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

2 Bedroom, 1 Bath Townhome for Rent

Available Now

73 Barnes Ave

BostonMA02128
property at 16 Boardman St

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

2 Bedroom, 2 Bath Condo for Rent

Available Now

16 Boardman St

BostonMA02128
property at 1000 Winthrop Ave

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 2 Bath Condo for Rent

Available Now

1000 Winthrop Ave

RevereMA02151
property at 280 Endicott Ave

$4,200

Total Monthly Price

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

3 Bedroom, 2 Bath Condo for Rent

Available Now

280 Endicott Ave

RevereMA02151
property at 61 Montmorenci Ave

$4,700

Total Monthly Price

Total Monthly Price

Base Rent
$4,700

Total Monthly Price
$4,700

5 Bedroom, 2 Bath Home for Rent

Available Now

61 Montmorenci Ave

BostonMA02128
property at 77 Faywood Ave

$5,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,100

Total Monthly Price
$5,100

4 Bedroom, 2.5 Bath Home for Rent

Available Now

77 Faywood Ave

BostonMA02128

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

property at 120 Gladstone St

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 1 Bath Condo for Rent

Available Now

120 Gladstone St, Unit 3

120 Gladstone St
BostonMA02128

Cottage Hill, Winthrop, MA Local Guide

Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

Read Article
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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.

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Pet Friendly Lifestyle
Cottage Hill, Winthrop, MA

Ranked #3

Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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Frequently Asked Questions about Cottage Hill

What type of rentals are currently available in Cottage Hill?

There are currently 101 Apartments for Rent in Cottage Hill, MA with pricing that ranges from $1,200 to $4,775. There are also 74 Single Family Homes for rent, Condos, and Townhome rentals currently available in Cottage Hill ranging from $1,595 to $6,000.

What is the current price range for Rental Homes in Cottage Hill?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Cottage Hill ranges from $1,595 to $6,000 with an average monthly rent of $3,372.

How much are larger Three and Four Bedroom Rentals in Cottage Hill?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Cottage Hill range from $2,250 to $4,775, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 to $6,000. Four Bedroom Single-Family rentals are also available starting from $3,700 and Four Bedroom Apartments start at $3,600.

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.

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