
Luxury Apartments for Rent in the Cottage Hill Neighborhood of Winthrop, MA (84 Rentals)
The most luxurious Apartments in the Cottage Hill area of Winthrop with high-end amenities, features, and finishes.


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953 Shirley St, Unit 2

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411 Shirley St, Unit 2

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92 Winthrop Shore Dr, Unit 2

5 Fremont St

600 Shirley St, Unit 1

92 Winthrop Shore Dr, Unit 2

370 Main St, Unit 2

87 Winthrop Shore Dr, Unit 2

70 Cottage Park Rd, Unit 1
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1040 Shirley St

5 Fremont St

68 Fremont St

125 Brookfield Rd

33-35 Cutler St

26 Forrest St

107 Winthrop St
20 Beacon St

46 Washington Ave

573 Shirley St
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Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

271 Shirley St

31-33 Pleasant St

180 Shirley St

400 Governors Dr

235 Washington Ave

63 Coral Ave

61 Coral Ave

35 Perkins St

585 Shirley St

50 Trident Ave
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36 Sturgis St

27 Bowdoin St

141 Grovers Ave

170 Cliff Ave

38 Hawthorn Ave, Unit 1

Fort Heath Apartments

Sora

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Amaya

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11 Boardman St, Unit 2

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1021 Winthrop Ave, Unit #2
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Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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85 Gladstone St, Unit 85 Gladstone Street

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172 Endicott Ave, Unit 2

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82 Gladstone St, Unit 2

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44 Ashley St, Unit #2

15 Walley St, Unit 206

1030 Bennington St, Unit 5

20 Bradstreet Ave

1 Orient Ave, Unit 2

31 Faywood Ave, Unit 3

90 Gladstone St, Unit 1
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
Cottage Hill, Winthrop, MA Local Guide

How much does it cost to rent an apartment in Cottage Hill?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Cottage Hill Studio Apartments | $2,566 | $1,595 | $2,910 |
| Cottage Hill 1 Bedroom Apartments | $2,662 | $1,200 | $4,269 |
| Cottage Hill 2 Bedroom Apartments | $3,150 | $2,195 | $4,256 |
| Cottage Hill 3 Bedroom Apartments | $3,281 | $2,250 | $4,775 |
| Cottage Hill 4 Bedroom Apartments | $4,090 | $3,600 | $4,650 |
Browse Apartments in this Neighborhood
There are currently 84 rentals with your search options within a 2 mile radius of the Cottage Hill Neighborhood of Winthrop, MA.
See all Apartments in WinthropExplore Winthrop
Cottage Hill, Winthrop, MA Local Guide
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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 ArticleQuick 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.
Pet Friendly LifestyleCottage Hill, Winthrop, MA
Ranked #3
Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
4.0Pet Friendly
Best Local Schools in Cottage Hill, Winthrop, MA
Arthur T. Cummings Elementary School
School data provided by Great Schools
Frequently Asked Questions about Cottage Hill
How much are Studio apartments in Cottage Hill?
There are currently 24 Studio Apartments in Cottage Hill with rent ranges from $1,595 to $2,910 with an average price of $2,566.
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 $4,269 with an average monthly rent of $2,662.
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 $2,195 to $4,256. Today's average rental price for Two Bedrooms here is $3,150.
How expensive are Cottage Hill Three Bedroom Apartments?
There are currently 22 Three Bedroom Apartments listings available in Cottage Hill on ApartmentHomeLiving.com. The pricing ranges from $2,250 to $4,775 - averaging $3,281 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

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
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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
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.

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 I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.