Cheap Apartments for Rent in the Wellesley Square Neighborhood of Wellesley, MA from $1,500 (14 Rentals)

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Search the lowest-cost Apartments available for rent right now in the Wellesley Square area of Wellesley.

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6 Bradford Rd, Unit 6 Bradford
$1,600
Total Monthly Price6 Month Lease Term

Total Monthly Price

Base Rent
$1,600

Total Monthly Price
$1,600
1 Bedroom Apartment Available Nov 1

6 Bradford Rd, Unit 6 Bradford

6 Bradford RdWellesley, MA 02481
Furnished
  • Smoke Free
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Ardemore At Wellesley
1 to 3 Bedroom Apartments

Ardemore At Wellesley

4-6 Cedar StWellesley, MA 02481
  • Utilities Included
property at 52 N Main St

52 N Main St

NatickMA01760

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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.

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57 Eliot St
1 to 2 Bedroom Apartments

57 Eliot St

57 Eliot StNatick, MA 01760

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.

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New Falls Apartments
2 to 4 Bedroom Apartments

New Falls Apartments

2281 Washington StNewton, MA 02462
  • Utilities Included

Wellesley Square, Wellesley, MA Local Guide

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 ListingModel NameBed/BathPriced From
Commonwealth ResidencesOne Bedroom1BR,1BA$2,750
Chestnut Hollow Apartments1 Bedroom Senior Apartment1BR,1BA$2,950
Woodland Station ApartmentsThe Riverside1BR,1BA$3,198
21 Summer St1 Bed1BR,1BA$3,200
Highland Park2 Bed - 2 Bath2BR,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 ListingModel NameBed/BathPrice Per Sq.Ft.
2044 Beacon St, Unit 22044 Beacon St4BR,4BA$0.54
2044 Beacon St, Unit 22044 Beacon St4BR,4BA$0.54
16 Lafayette Rd, Unit 11A16 Lafayette Rd2BR,1BA$0.26
2044 Beacon St, Unit 22044 Beacon St4BR,4BA$2.75
22 Cleveland Rd, Unit 122 Cleveland Rd3BR,1.5BA$2.71
22 Cleveland Rd, Unit 22 Cleveland Rd22 Cleveland Rd3BR,1.5BA$2.73
Hastings VillageLongfellow2BR,2BA$2.97
15 N Main St, Unit 215 N Main St3BR,1BA$2.59
25 Harris Ave, Unit 125 Harris Ave2BR,1BA$2.87
628 Washington St, Unit 3628 Washington St1BR,1BA$3.33

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Pet Friendly Lifestyle
Wellesley Square, Wellesley, MA

Ranked #1

Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

3.0
Pet Friendly

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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.

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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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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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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.

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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.