Cheap Homes for Rent in Wellesley Hills Neighborhood of Wellesley, MA from $1,600 (23 Rentals)

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Search the lowest-cost Homes available for rent right now in the Wellesley Hills area of Wellesley.

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.

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property at 19 Rosegate Rd

19 Rosegate Rd

NeedhamMA02494
property at 1117 Chestnut St

1117 Chestnut St

NewtonMA02464
property at 9 Higgins St

9 Higgins St, Unit 3

9 Higgins St
AuburndaleMA02466

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.

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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.

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Showing Results 1-23, Page 1 of 1

Wellesley Hills, Wellesley, MA Local Guide

Cheapest Available Wellesley Hills Apartments for Rent

 

The cheapest available apartment rental in the Wellesley Hills area of Boston, MA is a 1 Bed unit found at Chestnut Hollow Apartments priced from $2,850. The Kendrick has the second lowest priced unit, which is a 1 Bed apartment currently listed from $3,100. Here are the most affordable Wellesley Hills apartments for rent in Boston, MA:

Apartment ListingModel NameBed/BathPriced From
Chestnut Hollow Apartments1 Bedroom Senior Apartment1BR,1BA$2,850
The KendrickA21BR,1BA$3,100
Highland Park1 Bed - 1 Bath1BR,1BA$3,200

Best Value Apartments for Rent in Wellesley Hills, MA

As of May 23, 2025 the best value apartment in the Wellesley Hills area is the $0.54 price per square foot 2044 Beacon St Model at 2044 Beacon St, Unit 2 in the in the Wellesley Hills neighborhood starting from $5,400. The second greatest value Wellesley Hills apartment is the 2261 Washington St Model at 2261 Washington St, Unit 1 starting at $3,000 with a $0.30 price per square foot in the Wellesley Hills neighborhood. Here is today’s list of the best values for Wellesley Hills apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
2044 Beacon St, Unit 22044 Beacon St4BR,4BA$0.54
2261 Washington St, Unit 12261 Washington St2BR,1.5BA$0.30
1383 Washington St, Unit 31383 Washington St3BR,1BA$0.36
1383 Washington St, Unit 31383 Washington St3BR,1BA$0.36
1383 Washington St, Unit 31383 Washington St3BR,1BA$0.36
1383 Washington St, Unit 31383 Washington St3BR,1BA$0.36
27 Gammons Rd27 Gammons Rd5BR,4.5BA$2.00
2075 Beacon St, Unit 20752075 Beacon StStudio ,3.5BA$2.38
535 Auburn St, Unit 1535 Auburn St3BR,2BA$2.53
Charles River LandingPlan F (A1CD)1BR,1BA$2.99

Quick Rent Budget Calculator

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Frequently Asked Questions about Wellesley Hills

What type of rentals are currently available in Wellesley Hills?

There are currently 106 Apartments for Rent in Wellesley Hills, MA with pricing that ranges from $1,050 to $23,065. There are also 109 Single Family Homes for rent, Condos, and Townhome rentals currently available in Wellesley Hills ranging from $1,650 to $19,500.

What is the current price range for Rental Homes in Wellesley Hills?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Wellesley Hills ranges from $1,650 to $19,500 with an average monthly rent of $7,552.

How much are larger Three and Four Bedroom Rentals in Wellesley Hills?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Wellesley Hills range from $3,200 to $23,065, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,650 to $5,750. Four Bedroom Single-Family rentals are also available starting from $3,950 and Four Bedroom Apartments start at $5,400.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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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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.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.

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Navigating the Rental Market: Tips for First-Time Renters

Written by: Sandy Baker

Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.