
Cheap Apartments for Rent in the Wellesley Hills Neighborhood of Wellesley, MA from $1,600 (27 Rentals)
Search the lowest-cost Apartments available for rent right now in the Wellesley Hills area of Wellesley.


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628 Washington St, Unit 3

Ardemore At Wellesley

Room in Shared 5 bed/2.5 bath home

Room in Shared 5 bed/2 bath home

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Rosemary Lake Apartments
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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979 Chestnut St

278 Grove St

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282 Grove St, Unit 06

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282 Grove St, Unit 9

282 Grove St

282 Grove 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.

286 Grove St

1026 Chestnut St

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1026 Chestnut St, Unit 2A

286 Grove St

Total Monthly Price
286 Grove St, Unit 3

25 Westfield Rd, Unit 1
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.

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1024 Chestnut St, Unit 2A

278 Grove St

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1595 Commonwealth Ave

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25 Westfield Rd, Unit STU W. Newton

Concord Street Apartments

57 Eliot St
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

Woodland Park

Golda Meir House 62+ Senior Housing

100 Rosemary Way
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 | $2,829 | $2,500 | $3,090 |
| Wellesley Hills 1 Bedroom Apartments | $2,884 | $1,900 | $3,695 |
| Wellesley Hills 2 Bedroom Apartments | $3,814 | $2,400 | $5,602 |
| Wellesley Hills 3 Bedroom Apartments | $4,297 | $3,000 | $7,910 |
| Wellesley Hills 4 Bedroom Apartments | $5,225 | $4,250 | $5,500 |
Browse Apartments in this Neighborhood
There are currently 27 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
 | Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Woodland Park | 1 Bedroom | 1BR,1BA | $2,100 |
Best Value Apartments for Rent in Wellesley Hills, MA
As of January 24, 2026 the best value apartment in the Wellesley Hills area is the $0.23 price per square foot 282 Grove St Model at 282 Grove St, Unit 9 in the in the Wellesley Hills neighborhood starting from $2,300. The second greatest value Wellesley Hills apartment is the 286 Grove St Model at 286 Grove St, Unit 3 starting at $2,350 with a $0.24 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. |
|---|---|---|---|
| 282 Grove St, Unit 9 | 282 Grove St | 1BR,1BA | $0.23 |
| 286 Grove St, Unit 3 | 286 Grove St | 1BR,1BA | $0.24 |
| 53 Wyman St, Unit A-11 | 53 Wyman St | 2BR,1BA | $0.27 |
| 16 Lafayette Rd, Unit 11A | 16 Lafayette Rd | 2BR,1BA | $0.29 |
| 45 Wyman St, Unit #3 | 45 Wyman St | 2BR,1BA | $0.31 |
| 2044 Beacon St, Unit 2 | 2044 Beacon St | 4BR,4BA | $0.54 |
| 27 Gammons Rd | 27 Gammons Rd | 5BR,4.5BA | $2.00 |
| 829 Chestnut St | 829 Chestnut St | 5BR,4.5BA | $2.36 |
| New Falls Apartments | 2 Bedroom Townhouse | 2BR,1.5BA | $2.24 |
| 1026 Chestnut St, Unit 2A | 1026 Chestnut St | 1BR,1BA | $2.35 |
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 a cheap apartment in Wellesley Hills?
A cheap apartment is any apartment up to the 30% percentile of cost for the area, which in Wellesley Hills is under $2,100.
What is the price of a cheap apartment in Wellesley Hills?
The cheapest apartment in Wellesley Hills is Woodland Park which is listed at $2,100, while the average apartment in Wellesley Hills costs $10,250.
What types of apartments are the cheapest in Wellesley Hills?
Student, low-income, and by-the-bed apartments are typically the cheapest rentals in most cities, though they require qualifying criteria to rent. There are 2 regular apartments in Wellesley Hills that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.
How do the prices of cheap apartments compare to the average apartment in Wellesley Hills?
Cheap apartments in Wellesley Hills have an average cost of $148 which is $10,102 cheaper than the average rent for all rentals in Wellesley Hills.
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
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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.

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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

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.

Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.