
2 Bedroom Apartments for Rent in the Wellesley Hills Neighborhood of Wellesley, MA (49 Rentals)


Hastings Village

Highland Park

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Phillips Park Apartments

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15 Bemis Rd, Unit Apt #2

5 Westerly St

Terrazza

Washington House

Linden Square Townhomes
Renting with Roommates: Realistic Expectations for Shared Lease
Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

7 Bethel Rd

Cedar Place

127 Linden St

Wellesley Place

312 Washington St

Ardemore At Wellesley

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Woodland Station Apartments

Total Monthly Price
Chestnut Hollow Apartments

Total Monthly Price
Rosemary Lake Apartments
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.

New Falls Apartments

Total Monthly Price
268 Grove St, Unit U10

Total Monthly Price
1084 Chestnut St, Unit 1084 Chestnut St

Total Monthly Price
9 Keefe Ave, Unit 1

Total Monthly Price
9 Keefe Ave, Unit 1

760 Highland Ave

11 Keefe Ave

11 Keefe Ave, Unit 2

266 Grove St, Unit 1
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

278 Grove St, Unit 3

66 Spring Rd

2300 Commonwealth Ave

1193 Boylston St

266 Grove St

59 Rowe St

61-63-63 Newell Rd

78 Cumberland Rd

One Wingate Way
Renting Smart: Lease Basics Every Renter Needs
Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

52-54 Wyman St

144 Hancock St

Rosemary Ridge

Station at Riverside

996-998 Chestnut St

Woodland Park

Hamilton Highlands

Warren House

59-75 Wyman Street
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

2300 Commonwealth Ave

Concord Street Apartments

57 Eliot St

Golda Meir House 62+ Senior Housing
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 | $3,370 | $2,500 | $5,000 |
| Wellesley Hills 1 Bedroom Apartments | $3,279 | $1,900 | $4,393 |
Wellesley Hills 2 Bedroom Apartments | $4,168 | $2,400 | $6,019 |
| Wellesley Hills 3 Bedroom Apartments | $4,660 | $3,400 | $7,280 |
| Wellesley Hills 4 Bedroom Apartments | $5,200 | $4,250 | $5,950 |
Browse Apartments in this Neighborhood
There are currently 49 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
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Largest Available Wellesley Hills 2 Bedroom Apartments
The largest available 2 Bedroom apartment unit in the Wellesley Hills area of Boston, MA is found at The Nines and is listed at 1,346 square feet priced from $5,974. Here is today’s list of the largest available 2 Bedroom units in the area:
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| The Nines | M | 1,346 Sq Ft | $5,974 |
| Hastings Village | Emerson | 1,150 Sq Ft | $3,928 |
| Woodland Station Apartments | The Woodland | 1,113 Sq Ft | Call for Rates |
| Highland Park | 2 Bed - 2 Bath | 1,110 Sq Ft | $4,750 |
| Phillips Park Apartments | Two Bedroom | 1,000 Sq Ft | $3,500 |
| Woodland Park | 2 Bedroom | 790 Sq Ft | $2,650 |
| 59-75 Wyman Street | 2 Bedroom | 786 Sq Ft | $2,900 |
Cheapest Available Wellesley Hills 2 Bedroom Apartments
Currently the lowest priced 2 Bedroom apartment unit Wellesley Hills of Boston, MA is the 2 Bedroom Model starting from $2,650 at Woodland Park. The average price for all 2 Bedroom apartments in Wellesley Hills is currently $4,168. Here is today’s list of the cheapest available 2 Bedroom options in the area:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Woodland Park | 2 Bedroom | $2,650 |
| Chestnut Hollow Apartments | 2 Bedroom Senior Apartment | $2,800 |
| 59-75 Wyman Street | 2 Bedroom | $2,900 |
| Phillips Park Apartments | Two bedroom | $3,500 |
| Highland Park | 2 Bed - 2 Bath | $3,750 |
| Hastings Village | Emerson | $3,928 |
| The Nines | L | $5,246 |
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.
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How much rent can you afford?
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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 2 Bedroom Wellesley Hills Apartments
What is the Cheapest apartment in Wellesley Hills with 2 Bedroom?
Currently the most affordable 2 Bedroom in Wellesley Hills is at Woodland Park listed at $2,650.
How much is the average rent for a 2 Bedroom Wellesley Hills Apartment?
The average rent for a 2 Bedroom Apartment in Wellesley Hills is $4,168.
What is the largest available 2 Bedroom Wellesley Hills Apartment for rent?
Today's apartment with the most square footage in Wellesley Hills is a 1,346 square feet unit starting from $5,974 at The Nines.
What is the average size for Wellesley Hills 2 Bedroom Apartments for rent?
The average size for a 2 Bedroom rental in Wellesley Hills is currently 1,276 sq ft.
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
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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.