Room in Shared 5 bed/2.5 bath home, Unit B
337 Central St
BostonMA02466
Cheap Homes for Rent in the Wellesley Hills Neighborhood of Wellesley, MA from $1,000 (11 Rentals)
Search the lowest-cost Homes available for rent right now in the Wellesley Hills area of Wellesley.
Room in Shared 5 bed/2.5 bath home, Unit C
337 Central St
BostonMA02466
Room in Shared 5 bed/2.5 bath home, Unit D
337 Central St
BostonMA02466
Room in Shared 5 bed/2.5 bath home, Unit A
337 Central St
BostonMA02466
210 Hillside Ave
NeedhamMA02494
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.
63 Oak St, Unit 2B
63 Oak St
NeedhamMA02492
266 Grove St
NewtonMA02466
266 Grove St, Unit 1
266 Grove St
NewtonMA02466
59 Rowe St
NewtonMA02466
760 Highland Ave
NeedhamMA02494
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.
278 Grove St, Unit 3
278 Grove St
NewtonMA02466
Showing Results 1-11, Page 1 of 1
Wellesley Hills, Wellesley, MA Local Guide
How much does it cost to rent a home in Wellesley Hills?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Wellesley Hills 2 Bedroom Homes for Rent | $3,197 | $2,700 | $4,050 |
| Wellesley Hills 3 Bedroom Homes for Rent | $4,982 | $3,350 | $8,400 |
| Wellesley Hills 4 Bedroom Homes for Rent | $6,882 | $3,595 | $10,000+ |
| Wellesley Hills 5 Bedroom Homes for Rent | $9,097 | $1,025 | $10,000+ |
| Wellesley Hills 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 11 rentals with your search options within a 3 mile radius of the Wellesley Hills Neighborhood of Wellesley, MA.
Explore 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 1 Bed unit found at Woodland Park priced from $2,350. Chestnut Hollow Apartments has the second lowest priced unit, which is a 2 Beds apartment currently listed from $2,800. Here are the most affordable Wellesley Hills apartments for rent in Boston, MA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Woodland Park | 1 Bedroom | 1BR,1BA | $2,350 |
| Chestnut Hollow Apartments | 2 Bedroom Senior Apartment | 2BR,1BA | $2,800 |
| 59-75 Wyman Street | 2 Bedroom | 2BR,1BA | $2,900 |
Best Value Apartments for Rent in Wellesley Hills, MA
As of July 12, 2026 the best value apartment in the Wellesley Hills area is the $2.00 price per square foot 27 Gammons Rd Model at 27 Gammons Rd in the in the Wellesley Hills neighborhood starting from $12,000. The second greatest value Wellesley Hills apartment is the 44 High St Model at 44 High St, Unit 1 starting at $4,250 with a $3.04 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. |
|---|---|---|---|
| 27 Gammons Rd | 27 Gammons Rd | 5BR,4.5BA | $2.00 |
| 44 High St, Unit 1 | 44 High St | 4BR,2BA | $3.04 |
| 1383 Washington St | 1383 Washington St | 3BR,1BA | $3.00 |
| 69 Saco St | 69 Saco St | 3BR,1.5BA | $3.29 |
| Highland Park | 2 Bed - 2 Bath | 2BR,2BA | $3.38 |
| 287 Elliot St, Unit 11 | 287 Elliot St | 1BR,1BA | $2.10 |
| 15 Bemis Rd, Unit Apt #2 | 15 Bemis Rd | 2BR,1BA | $3.17 |
| 1024 Chestnut St, Unit 2A | 1024 Chestnut St | 1BR,1BA | $3.27 |
| Woodland Park | 1 Bedroom | 1BR,1BA | $3.21 |
| 198 Concord St, Unit 16 | 198 Concord St | 1BR,1BA | $3.21 |
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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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 Wellesley Hills
What type of rentals are currently available in Wellesley Hills?
There are currently 83 Apartments for Rent in Wellesley Hills, MA with pricing that ranges from $1,900 to $12,000. There are also 75 Single Family Homes for rent, Condos, and Townhome rentals currently available in Wellesley Hills ranging from $1,025 to $25,000.
What is the current price range for Rental Homes in Wellesley Hills?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Wellesley Hills ranges from $1,025 to $25,000 with an average monthly rent of $6,700.
How much are larger Three and Four Bedroom Rentals in Wellesley Hills?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Wellesley Hills range from $3,400 to $7,280, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,350 to $8,400. Four Bedroom Single-Family rentals are also available starting from $3,595 and Four Bedroom Apartments start at $4,250.
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 Expert's 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
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.
Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
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.