
Cheap Apartments for Rent in Winchester, MA from $1,400 (76 Rentals)
Search the lowest-cost Apartments available for rent right now in Winchester.


160 Swanton St, Unit #713

2 Elmwood Ave

Brattle Drive Apartments

16 Flagg St

Leisure Lane Apartments
Boston's Best Affordable Neighborhoods
Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead

23 Burlington St

393 Massachusetts Ave, Unit Studio VERY CLEAN

998 Massachusetts Ave, Unit 5

7 Brattle Dr, Unit 1 BED 1 BATH

163 Summer St

219 Massachusetts Ave, Unit 1

4 Menotomy Rd

555 Main St

880 Massachusetts Ave, Unit 1 BED VERY CLEANNN

201 Forest St, Unit 2C

11 Allen St

1011 Massachusetts Ave, Unit 2
Winchester, MA Local Guide

How much does it cost to rent an apartment in Winchester?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Cheap Winchester Studio Apartments | $2,496 | $1,650 | $5,214 |
Cheap Winchester 1 Bedroom Apartments | $2,782 | $1,500 | $6,807 |
Cheap Winchester 2 Bedroom Apartments | $3,283 | $1,900 | $8,935 |
Cheap Winchester 3 Bedroom Apartments | $3,727 | $2,600 | $10,000+ |
Cheap Winchester 4 Bedroom Apartments | $4,563 | $3,249 | $5,750 |
Winchester 5 Bedroom Apartments | $5,546 | $4,000 | $7,800 |
Winchester 6 Bedroom Apartments | $7,439 | $1,800 | $9,900 |
Browse Top Apartments in Winchester
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Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
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Cheapest Available Winchester Apartments for Rent
 Apartment Listing | Model Name | Bed/Bath | Priced From |
---|---|---|---|
Leisure Lane Apartments | studio | Studio,1BA | $1,705 |
Best Value Apartments for Rent in Winchester, MA
As of March 16, 2025 the best value apartment in the Winchester area is the $0.23 price per square foot 78 Decatur St Model at 78 Decatur St, Unit 3 in the in the East Arlington neighborhood starting from $2,300. The second greatest value Winchester apartment is the 1011 Massachusetts Ave Model at 1011 Massachusetts Ave, Unit 2 starting at $2,295 with a $0.23 price per square foot in the Rock Meadow neighborhood. Here is today’s list of the best values for Winchester apartments based on price per square foot:
Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
---|---|---|---|
78 Decatur St, Unit 3 | 78 Decatur St | 1BR,1BA | $0.23 |
1011 Massachusetts Ave, Unit 2 | 1011 Massachusetts Ave | 1BR,1BA | $0.23 |
47 Orchard St, Unit 3 | 47 Orchard St | 3BR,1BA | $0.27 |
79 Capen St, Unit 1 | 79 Capen St | 2BR,1BA | $0.27 |
77 Fairfax St, Unit B | 77 Fairfax St | Studio ,1BA | $0.20 |
101 Boston Ave, Unit 1 | 101 Boston Ave | 2BR,1BA | $0.26 |
101 Boston Ave, Unit 1 | 101 Boston Ave | 2BR,1BA | $0.26 |
95 W Adams St, Unit 1 | 95 W Adams St | 2BR,1BA | $0.25 |
96 W Adams St, Unit 2 | 96 W Adams St | 2BR,1BA | $0.26 |
101 Boston Ave, Unit 1 | 101 Boston Ave | 2BR,1BA | $0.26 |
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Getting Around Winchester, MA
Walk Score®
71 / 100
Very Walkable
Most errands can be accomplished on foot
Bike Score®
67 / 100
Bikeable
Some bike infrastructure
Transit Score®
1 / 100
Minimal Transit
It may be possible to get on a bus
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Cheap Winchester Apartments
What is the Cheapest Studio apartment in Winchester?
Currently the most affordable Cheap Studio Apartment in Winchester is at Leisure Lane Apartments listed at $1,705.
How much is rent for a Cheap One Bedroom Winchester Apartment?
The lowest price for a Cheap One Bedroom Winchester Apartment is $1,905 at Leisure Lane Apartments.
What is the lowest price for a Cheap Two Bedroom Winchester Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winchester is starting from $2,195 at Leisure Lane Apartments.
What is the most affordable Winchester Three Bedroom Apartment?
The best deal on a cheap Winchester Three Bedroom Apartment rental is at and starts from $2,600.
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.

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.

Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

What to Know About Fees and Fines When Renting
Written by: Trey Huguley
When it comes to renting a new apartment or home there can be a number of fees that you will want to keep in mind going into the process.

Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.