
Cheap Apartments for Rent in the Wellesley Hills Neighborhood of Wellesley, MA from $1,600 (21 Rentals)
Search the lowest-cost Apartments available for rent right now in the Wellesley Hills area of Wellesley.


Ardemore At Wellesley

Room in Shared 5 bed/2.5 bath home

Room in Shared 5 bed/2 bath home

Room in Shared 5 bed/2.5 bath home

Rosemary Lake Apartments

2366 Commonwealth Ave
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.

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282 Grove St, Unit 9

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286 Grove St, Unit 3

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53 Wyman St

25 Westfield Rd, Unit 1

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16 Lafayette Rd

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1024 Chestnut St, Unit 2A

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1595 Commonwealth Ave
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.

56 Eliot St

Total Monthly Price
25 Westfield Rd, Unit STU W. Newton

63 Oak St

77 Wyman St

Concord Street Apartments

57 Eliot St

Golda Meir House 62+ Senior Housing
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.
Wellesley Hills, Wellesley, MA Local Guide

How much does it cost to rent an apartment in Wellesley Hills?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Wellesley Hills Studio Apartments | $2,593 | $2,471 | $2,776 |
| Wellesley Hills 1 Bedroom Apartments | $2,939 | $1,900 | $3,741 |
| Wellesley Hills 2 Bedroom Apartments | $3,851 | $2,400 | $5,411 |
| Wellesley Hills 3 Bedroom Apartments | $4,442 | $3,000 | $8,049 |
| Wellesley Hills 4 Bedroom Apartments | $5,216 | $4,250 | $5,750 |
Browse Apartments in this Neighborhood
There are currently 21 rentals with your search options within a 3 mile radius of the Wellesley Hills Neighborhood of Wellesley, MA.
See all Apartments in WellesleyExplore Wellesley
Wellesley Hills, Wellesley, MA Local Guide
- Nearby Wellesley neighborhoods
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Cheapest Available Wellesley Hills Apartments for Rent
 The cheapest available apartment rental in the Wellesley Hills area of Boston, MA is a Studio unit found at The Nines priced from $2,471. New Falls Apartments has the second lowest priced unit, which is a 2 Beds apartment currently listed from $2,776. Here are the most affordable Wellesley Hills apartments for rent in Boston, MA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Nines | A | Studio,1BA | $2,471 |
| New Falls Apartments | 2 Bedroom Garden | 2BR,1BA | $2,776 |
| Chestnut Hollow Apartments | 1 Bedroom Senior Apartment | 1BR,1BA | $2,950 |
Best Value Apartments for Rent in Wellesley Hills, MA
As of March 11, 2026 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 282 Grove St Model at 282 Grove St, Unit 9 starting at $2,300 with a $0.23 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 Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 2044 Beacon St, Unit 2 | 2044 Beacon St | 4BR,4BA | $0.54 |
| 282 Grove St, Unit 9 | 282 Grove St | 1BR,1BA | $0.23 |
| 286 Grove St, Unit 3 | 286 Grove St | 1BR,1BA | $0.24 |
| 27 Gammons Rd | 27 Gammons Rd | 5BR,4.5BA | $2.00 |
| 829 Chestnut St | 829 Chestnut St | 5BR,4.5BA | $2.36 |
| 2044 Beacon St, Unit 2 | 2044 Beacon St | 4BR,4BA | $2.75 |
| 44 High St, Unit 1 | 44 High St | 4BR,2BA | $3.04 |
| New Falls Apartments | 2 Bedroom Townhouse | 2BR,1.5BA | $2.24 |
| 27 Oakwood Rd, Unit 2 | 27 Oakwood Rd | 3BR,1BA | $2.50 |
| 1383 Washington St | 1383 Washington St | 3BR,1BA | $3.00 |
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 ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
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.
Pet Friendly LifestyleWellesley Hills, Wellesley, MA
Ranked #5
Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
4.0Pet Friendly
Best Local Schools in Wellesley Hills, Wellesley, MA
School data provided by Great Schools
Frequently Asked Questions about Cheap Wellesley Hills Apartments
What is the Cheapest Studio apartment in Wellesley Hills?
Currently the most affordable Cheap Studio Apartment in Wellesley Hills is at The Nines listed at $2,471.
How much is rent for a Cheap One Bedroom Wellesley Hills Apartment?
The lowest price for a Cheap One Bedroom Wellesley Hills Apartment is $2,950 at Chestnut Hollow Apartments.
What is the lowest price for a Cheap Two Bedroom Wellesley Hills Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Wellesley Hills is starting from $2,776 at New Falls Apartments.
What is the most affordable Wellesley Hills Three Bedroom Apartment?
The best deal on a cheap Wellesley Hills Three Bedroom Apartment rental is at The Nines and starts from $7,199.
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
Written by: Amelia Ramstead
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.

A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
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
Written by: Amelia Ramstead
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
Written by: Amelia Ramstead
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

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.