22 High St, Unit 14
22 High St
MedfordMA02155
Cheap Homes for Rent in Winchester, MA from $1,800 (82 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
147 Pleasant St, Unit B
147 Pleasant St
WoburnMA01801
21 Bradlee Rd
MedfordMA02155
157 Franklin St, Unit Jutta Donahue
157 Franklin St
StonehamMA02180
385 Massachusetts Ave
ArlingtonMA02474
47 Broadway
ArlingtonMA02474
129 Pleasant St
ArlingtonMA02476
7 Harris Cir
ArlingtonMA02474
26 Heath Rd
ArlingtonMA02474
19 Arizona Ter, Unit 4
19 Arizona Ter
ArlingtonMA02474
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
19 Arizona Ter
ArlingtonMA02474
19 Arizona Ter, Unit 4
19 Arizona Ter
ArlingtonMA02474
7 Bartlett Ave
ArlingtonMA02476
2 Elmwood Ave
WinchesterMA01890
35 Prospect St
WoburnMA01801
14 Dudley St, Unit 6
14 Dudley St
ArlingtonMA02476
7 Brattle Dr, Unit 1
7 Brattle Dr
ArlingtonMA02474
7 Brattle Dr
ArlingtonMA02474
200 Swanton St, Unit 704
200 Swanton St
WinchesterMA01890
12 Arizona Terrace
ArlingtonMA02474
3 Brattle Dr
ArlingtonMA02474
14 Old Colony Ln
ArlingtonMA02476
211 Forest St, Unit 1
211 Forest St
ArlingtonMA02474
64 Forest St
MedfordMA02155
9 Wildwood Rd
MedfordMA02155
49 Broadway, Unit #6
49 Broadway
ArlingtonMA02474
14 Brattle Ln, Unit 31
14 Brattle Ln
ArlingtonMA02474
1 Brattle Dr
ArlingtonMA02474
114 Pleasant St
ArlingtonMA02476
12 Totman Dr
WoburnMA01801
35 Vine St
WinchesterMA01890
7 Arizona Ter, Unit 2
7 Arizona Ter
ArlingtonMA02474
32 Hamilton Rd
ArlingtonMA02474
27 Arlington Rd, Unit 5
27 Arlington Rd
WoburnMA01801
31 Arlington Rd, Unit 5
31 Arlington Rd
WoburnMA01801
91 Hillsdale Rd, Unit 2A
91 Hillsdale Rd
MedfordMA02155
79 Capen St
MedfordMA02155
422 High St, Unit 30
422 High St
MedfordMA02155
2 Elmwood Ave
WinchesterMA01890
20 Hamilton Rd
ArlingtonMA02474
1 Watermill Pl
ArlingtonMA02476
20 Hamilton Rd, Unit 201
20 Hamilton Rd
ArlingtonMA02474
2 Elmwood Ave
WinchesterMA01890
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
10 Pine Ave, Unit 10
10 Pine Ave
ArlingtonMA02474
190 High St, Unit 109
190 High St
MedfordMA02155
30 Early Ave, Unit 1
30 Early Ave
MedfordMA02155
19 Canal St, Unit 2
19 Canal St
MedfordMA02155
28 Maple Ave, Unit 1
28 Maple Ave
MedfordMA02155
125 Pleasant St, Unit 401
125 Pleasant St
ArlingtonMA02476
Winchester, MA Local Guide
Downtown Winchester, Massachusetts by Moonshine4711 is licensed under CC BY-SA 3.0
How much does it cost to rent a home in Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $2,955 | $2,300 | $4,000 |
| Winchester 3 Bedroom Homes for Rent | $3,956 | $2,800 | $7,200 |
| Winchester 4 Bedroom Homes for Rent | $4,915 | $3,200 | $7,250 |
| Winchester 5 Bedroom Homes for Rent | $6,200 | $2,800 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $7,978 | $5,500 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $7,975 | $7,975 | $7,975 |
Browse Top Homes for Rent in Winchester
Explore Winchester
Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Winchester Apartments for Rent
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Leisure Lane Apartments | studio | Studio,1BA | $1,795 |
Best Value Apartments for Rent in Winchester, MA
As of April 05, 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 |
| 77 Fairfax St, Unit B | 77 Fairfax St | Studio ,1BA | $0.20 |
| 77 Gordon St, Unit #1 | 77 Gordon St | 2BR,2BA | $0.23 |
| 78 Gordon St, Unit #1 | 78 Gordon St | 2BR,2BA | $0.23 |
| 36 Montvale Ave | 36 Montvale Ave | 2BR,1BA | $0.18 |
| 54 West St, Unit #19 | 54 West St | 1BR,1BA | $0.18 |
| 3 Forest St, Unit #202 | 3 Forest St | 1BR,1BA | $0.18 |
| 95 W Adams St, Unit 1 | 95 W Adams St | 2BR,1BA | $0.25 |
| 47 Harvard Ave | 47 Harvard Ave | 2BR,1BA | $0.26 |
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Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 1029 Apartments for Rent in Winchester, MA with pricing that ranges from $1,100 to $11,187. There are also 469 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,800 to $25,000.
What is the current price range for Rental Homes in Winchester?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester ranges from $1,800 to $25,000 with an average monthly rent of $4,809.
How much are larger Three and Four Bedroom Rentals in Winchester?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester range from $2,600 to $11,187, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $7,200. Four Bedroom Single-Family rentals are also available starting from $3,200 and Four Bedroom Apartments start at $3,000.
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.
Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.
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.