52 N Main St, Unit 5
52 N Main St
NatickMA01760
Cheap Homes for Rent in the Wellesley Square Neighborhood of Wellesley, MA from $2,300 (9 Rentals)
Search the lowest-cost Homes available for rent right now in the Wellesley Square area of Wellesley.
210 Hillside Ave
NeedhamMA02494
63 Oak St, Unit 2B
63 Oak St
NeedhamMA02492
37 Centre St
NatickMA01760
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.
37 Centre St
NatickMA01760
1940 Washington St, Unit 207
1940 Washington St
NewtonMA02466
1940 Washington St, Unit 235
1940 Washington St
NewtonMA02466
1282 Central Ave
NeedhamMA02492
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.
283 Hillside Ave, Unit 1
283 Hillside Ave
NeedhamMA02494
Showing Results 1-9, Page 1 of 1
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 | $3,900 | $3,900 | $3,900 |
| Wellesley Square 3 Bedroom Homes for Rent | $4,946 | $3,650 | $8,400 |
| Wellesley Square 4 Bedroom Homes for Rent | $7,569 | $4,000 | $10,000+ |
| Wellesley Square 5 Bedroom Homes for Rent | $13,780 | $4,900 | $10,000+ |
| Wellesley Square 6 Bedroom Homes for Rent | $13,000 | $10,000 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 9 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 July 16, 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 Emerson Model at Hastings Village starting at $3,928 with a $3.42 price per square foot in the Wellesley Hills 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 |
| Hastings Village | Emerson | 2BR,2BA | $3.42 |
| Highland Park | 2 Bed - 2 Bath | 2BR,2BA | $3.38 |
| 13 West Central Street | 2 bed | 2BR,1BA | $3.97 |
| 21 Summer St | 2 Bed | 2BR,2BA | $3.66 |
| 15 Bemis Rd, Unit Apt #2 | 15 Bemis Rd | 2BR,1BA | $3.17 |
| 45 E. Central St. | 1-BD | 1BR,1BA | $4.21 |
| Natick Corner | One Bedroom | 1BR,1BA | $3.64 |
| 198 Concord St, Unit 16 | 198 Concord St | 1BR,1BA | $3.21 |
| 14 Abbott St, Unit 2Rear | 14 Abbott St | 1BR,1BA | $4.63 |
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
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.
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Best Local Schools in Wellesley Square, Wellesley, MA
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Frequently Asked Questions about Wellesley Square
What type of rentals are currently available in Wellesley Square?
There are currently 68 Apartments for Rent in Wellesley Square, MA with pricing that ranges from $1,900 to $7,280. There are also 43 Single Family Homes for rent, Condos, and Townhome rentals currently available in Wellesley Square ranging from $2,300 to $25,000.
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 $2,300 to $25,000 with an average monthly rent of $7,682.
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 $2,850 to $7,280, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,650 to $8,400. Four Bedroom Single-Family rentals are also available starting from $4,000 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.
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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.