
Cheap Homes for Rent in Wellesley Square Neighborhood of Wellesley, MA from $1,700 (6 Rentals)
Search the lowest-cost Homes available for rent right now in the Wellesley Square area of Wellesley.


129 North Ave

210 Hillside Ave
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

1932 Washington St

5 General Greene Ave, Unit 6

5 General Greene Ave, Unit 5
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
Wellesley Square, Wellesley, MA Local Guide

How much does it cost to rent a home in Wellesley Square?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Wellesley Square 2 Bedroom Homes for Rent | $2,910 | $2,400 | $4,200 |
| Wellesley Square 3 Bedroom Homes for Rent | $5,132 | $3,650 | $8,750 |
| Wellesley Square 4 Bedroom Homes for Rent | $5,755 | $4,500 | $6,900 |
| Wellesley Square 5 Bedroom Homes for Rent | $8,960 | $7,500 | $10,000+ |
| Wellesley Square 6 Bedroom Homes for Rent | $15,000 | $10,000 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 6 rentals with your search options within a 3 mile radius of the Wellesley Square Neighborhood of Wellesley, MA.
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Wellesley Square, Wellesley, MA Local Guide
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Cheapest Available Wellesley Square Apartments for Rent
 The cheapest available apartment rental in the Wellesley Square area of Boston, MA is a Studio unit found at Commonwealth Residences priced from $2,400. Natick Corner has the second lowest priced unit, which is a 1 Bed apartment currently listed from $2,600. Here are the most affordable Wellesley Square apartments for rent in Boston, MA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Commonwealth Residences | Studio | Studio,1BA | $2,400 |
| Natick Corner | One Bedroom | 1BR,1BA | $2,600 |
| Chestnut Hollow Apartments | 2 Bedroom Senior Apartment | 2BR,1BA | $2,800 |
Best Value Apartments for Rent in Wellesley Square, MA
As of May 31, 2026 the best value apartment in the Wellesley Square area is the $3.48 price per square foot Two Bedroom Model at Phillips Park Apartments in the in the Wellesley Hills neighborhood starting from $4,000. The second greatest value Wellesley Square apartment is the 1-BD Model at 45 E. Central St. starting at $3,200 with a $4.21 price per square foot in the Historic District neighborhood. Here is today’s list of the best values for Wellesley Square apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Phillips Park Apartments | Two Bedroom | 2BR,2BA | $3.48 |
| 45 E. Central St. | 1-BD | 1BR,1BA | $4.21 |
| Woodland Station Apartments | The Riverside | 1BR,1BA | $4.76 |
| Natick Corner | One Bedroom | 1BR,1BA | $3.64 |
| 21 Summer St | 1 Bed | 1BR,1BA | $4.27 |
| Commonwealth Residences | Studio | Studio ,1BA | $5.03 |
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 ArticleReal 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.
Best Local Schools in Wellesley Square, Wellesley, MA
School data provided by Great Schools
Frequently Asked Questions about Wellesley Square
What type of rentals are currently available in Wellesley Square?
There are currently 58 Apartments for Rent in Wellesley Square, MA with pricing that ranges from $1,450 to $35,666. There are also 43 Single Family Homes for rent, Condos, and Townhome rentals currently available in Wellesley Square ranging from $1,700 to $15,000.
What is the current price range for Rental Homes in Wellesley Square?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Wellesley Square ranges from $1,700 to $15,000 with an average monthly rent of $5,983.
How much are larger Three and Four Bedroom Rentals in Wellesley Square?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Wellesley Square range from $3,400 to $6,201, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,650 to $8,750. Four Bedroom Single-Family rentals are also available starting from $4,500 and Four Bedroom Apartments start at $5,400.
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
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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
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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

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.

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.