Luxury Apartments for Rent in the Cottage Hill Neighborhood of Winthrop, MA (76 Rentals)

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

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181 Winthrop Shore Dr, Unit #2
$2,995
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,995

Total Monthly Price
$2,995
2 Bedroom Apartment Available May 1

181 Winthrop Shore Dr, Unit #2

181 Winthrop Shore DrWinthrop, MA 02152
Cost Per Sq.Ft.
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62 Upland Rd, Unit 3
$3,450
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,450

Total Monthly Price
$3,450
3 Bedroom Apartment Available Mar 1

62 Upland Rd, Unit 3

62 Upland RdWinthrop, MA 02152
Cost Per Sq.Ft.
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 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 76 Fremont St

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

2 Bedroom, 1 Bath Condo for Rent

Available Now

76 Fremont St, Unit 3

76 Fremont St
WinthropMA02152

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 300 Governors Dr

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 1 Bath Home for Rent

Available Now

300 Governors Dr

WinthropMA02152
property at 1100 Governors Dr

$2,550

Total Monthly Price

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

2 Bedroom, 1 Bath Home for Rent

Available Now

1100 Governors Dr

WinthropMA02152
property at 374 Shirley St

$3,100

Total Monthly Price

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

3 Bedroom, 2 Bath Home for Rent

Available Now

374 Shirley St

WinthropMA02152
property at 181 Winthrop Shore Dr

$2,995

Total Monthly Price

Total Monthly Price

Base Rent
$2,995

Total Monthly Price
$2,995

2 Bedroom, 1 Bath Home for Rent

Available Now

181 Winthrop Shore Dr

WinthropMA02152
property at 31 Cutler St

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 1 Bath Home for Rent

Available Now

31 Cutler St

WinthropMA02152
property at 31-33-33 Pleasant Park Rd

$2,600

Total Monthly Price

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom Rentals

Available Now

property at 14 Beach Rd

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 0.5 Bath Home for Rent

Available Now

14 Beach Rd

WinthropMA02152

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.

property at 11 Forrest St

$3,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

4 Bedroom, 2 Bath Home for Rent

Available Now

11 Forrest St

WinthropMA02152
property at 25 Seafoam Ave

$3,600

Total Monthly Price

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

4 Bedroom, 2 Bath Home for Rent

Available Now

25 Seafoam Ave

WinthropMA02152
property at 10 Charles St

$2,600

Total Monthly Price

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

3 Bedroom, 1 Bath Home for Rent

Available Now

10 Charles St

WinthropMA02152
property at 117 Winthrop Shore Dr

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 1 Bath Home for Rent

Available Now

117 Winthrop Shore Dr

WinthropMA02152
property at 5 Fremont St

$2,500 - $3,300

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

1 To 3 Bedroom Rentals

Available Now

5 Fremont St

WinthropMA02152
property at 19 Beach Rd

$2,750

Total Monthly Price

Total Monthly Price

Base Rent
$2,750

Total Monthly Price
$2,750

3 Bedroom, 1 Bath Home for Rent

Available Now

19 Beach Rd

WinthropMA02152
property at 23 Tafts Ave

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

1 Bedroom, 1 Bath Condo for Rent

Available Now

23 Tafts Ave

WinthropMA02152
property at 59 Coral Ave

$2,500 - $3,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 To 4 Bedroom Rentals

Available Now

59 Coral Ave

WinthropMA02152
property at 45 Pleasant St

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

3 Bedroom, 1 Bath Townhome for Rent

Available Now

45 Pleasant St

WinthropMA02152
property at 1 Seal Harbor Rd

$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

1 Seal Harbor Rd

WinthropMA02152

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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 Mar 14

63 Coral Ave

WinthropMA02152
property at 36 Trident Ave

$3,000

Total Monthly Price

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

2 Bedroom, 1 Bath Condo for Rent

Available Now

36 Trident Ave

WinthropMA02152
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 Apr 1

61 Coral Ave

WinthropMA02152
property at 69 Fremont St

$3,100

Total Monthly Price

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

3 Bedroom, 1 Bath Townhome for Rent

Available Now

69 Fremont St

WinthropMA02152
property at 3 Seafoam 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

3 Seafoam Ave

WinthropMA02152
property at 62 Park Ave

$3,700

Total Monthly Price

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

3 Bedroom, 2 Bath Condo for Rent

Available Now

62 Park Ave

WinthropMA02152
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Amaya
Rent Specials
$2,030 - $4,075
Total Monthly Price

Total Monthly Price

Base Rent
$2,030 - $4,075

Total Monthly Price
$2,030 - $4,075
Studio to 2 Bedroom Apartments Available Now

Amaya

50 Salt StRevere, MA 02151
Affordability
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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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120 Gladstone St, Unit #3
$3,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200
3 Bedroom Apartment Available Now

120 Gladstone St, Unit #3

120 Gladstone StBoston, MA 02128
Affordability
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44 Ashley St
$3,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800
4 Bedroom Apartment Available Now

44 Ashley St

44 Ashley StBoston, MA 02128
Affordability
property at 25 Pratt St

$2,150 - $3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,150 - $3,300

Total Monthly Price
$2,150 - $3,300

1 To 3 Bedroom Condos for Rent

Available Now

25 Pratt St

BostonMA02134
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

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

Cottage Hill, Winthrop, MA Local Guide

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
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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
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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.

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 #2

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

How much are Studio apartments in Cottage Hill?

There are currently 28 Studio Apartments in Cottage Hill with rent ranges from $1,650 to $2,705 with an average price of $2,316.

What is the current price range for One Bedroom Cottage Hill Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Cottage Hill ranges from $1,200 to $3,480 with an average monthly rent of $2,734.

What does renting a Two Bedroom Apartment in Cottage Hill cost?

The monthly rent prices of Two Bedroom Apartments currently available in Cottage Hill range from $2,300 to $5,971. Today's average rental price for Two Bedrooms here is $3,173.

How expensive are Cottage Hill Three Bedroom Apartments?

There are currently 16 Three Bedroom Apartments listings available in Cottage Hill on ApartmentHomeLiving.com. The pricing ranges from $2,600 to $4,009 - averaging $3,320 for the location.

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

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A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

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Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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Renting with Roommates: Realistic Expectations for Shared Lease

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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.