
Cheap Apartments for Rent in the Wellesley Square Neighborhood of Wellesley, MA from $1,500 (14 Rentals)
Search the lowest-cost Apartments available for rent right now in the Wellesley Square area of Wellesley.


410 Washington St

67 Loker St

Rosemary Lake Apartments

26 N Main St

52 N Main St
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.

12 Walnut St
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

1315 Highland Ave
Wellesley Square, Wellesley, MA Local Guide

How much does it cost to rent an apartment in Wellesley Square?
Bedroom | Average Price | Cheapest Price | Highest Price |
---|---|---|---|
Wellesley Square Studio Apartments | $1,650 | $1,650 | $1,650 |
Wellesley Square 1 Bedroom Apartments | $3,061 | $1,600 | $9,023 |
Wellesley Square 2 Bedroom Apartments | $3,585 | $2,150 | $8,849 |
Wellesley Square 3 Bedroom Apartments | $4,400 | $2,898 | $6,491 |
Wellesley Square 4 Bedroom Apartments | $5,185 | $3,600 | $5,600 |
Browse Apartments in this Neighborhood
There are currently 14 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 1 Bed unit found at Commonwealth Residences priced from $2,750. Chestnut Hollow Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $2,950. Here are the most affordable Wellesley Square apartments for rent in Boston, MA:
Apartment Listing | Model Name | Bed/Bath | Priced From |
---|---|---|---|
Commonwealth Residences | One Bedroom | 1BR,1BA | $2,750 |
Chestnut Hollow Apartments | 1 Bedroom Senior Apartment | 1BR,1BA | $2,950 |
Woodland Station Apartments | The Riverside | 1BR,1BA | $3,198 |
21 Summer St | 1 Bed | 1BR,1BA | $3,200 |
Highland Park | 2 Bed - 2 Bath | 2BR,2BA | $3,750 |
Best Value Apartments for Rent in Wellesley Square, MA
As of September 18, 2025 the best value apartment in the Wellesley Square 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 Square apartment is the 2044 Beacon St Model at 2044 Beacon St, Unit 2 starting at $5,400 with a $0.54 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. |
---|---|---|---|
2044 Beacon St, Unit 2 | 2044 Beacon St | 4BR,4BA | $0.54 |
2044 Beacon St, Unit 2 | 2044 Beacon St | 4BR,4BA | $0.54 |
16 Lafayette Rd, Unit 11A | 16 Lafayette Rd | 2BR,1BA | $0.26 |
2044 Beacon St, Unit 2 | 2044 Beacon St | 4BR,4BA | $2.75 |
22 Cleveland Rd, Unit 1 | 22 Cleveland Rd | 3BR,1.5BA | $2.71 |
22 Cleveland Rd, Unit 22 Cleveland Rd | 22 Cleveland Rd | 3BR,1.5BA | $2.73 |
Hastings Village | Longfellow | 2BR,2BA | $2.97 |
15 N Main St, Unit 2 | 15 N Main St | 3BR,1BA | $2.59 |
25 Harris Ave, Unit 1 | 25 Harris Ave | 2BR,1BA | $2.87 |
628 Washington St, Unit 3 | 628 Washington St | 1BR,1BA | $3.33 |
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Pet Friendly LifestyleWellesley Square, Wellesley, MA
Ranked #1
Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.0Pet Friendly
Best Local Schools in Wellesley Square, Wellesley, MA
School data provided by Great Schools
Frequently Asked Questions about Cheap Wellesley Square Apartments
How much is rent for a Cheap One Bedroom Wellesley Square Apartment?
The lowest price for a Cheap One Bedroom Wellesley Square Apartment is $2,750 at Commonwealth Residences.
What is the lowest price for a Cheap Two Bedroom Wellesley Square Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Wellesley Square is starting from $3,200 at Commonwealth Residences.
What is the most affordable Wellesley Square Three Bedroom Apartment?
The best deal on a cheap Wellesley Square Three Bedroom Apartment rental is at Highland Park and starts from $4,950.
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.

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.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!

The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.