390 Fellsway W, Unit 5A
390 Fellsway W
MedfordMA02155
Cheap Homes for Rent in Winchester, MA from $1,700 (54 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
147 Pleasant St, Unit B
147 Pleasant St
WoburnMA01801
22 High St, Unit 14
22 High St
MedfordMA02155
21 Bradlee Rd
MedfordMA02155
129 Pleasant St
ArlingtonMA02476
49 Broadway
ArlingtonMA02474
47 Broadway
ArlingtonMA02474
47 Broadway
ArlingtonMA02474
11 Old Colony Ln
ArlingtonMA02476
43 Pomeworth St, Unit 34
43 Pomeworth St
StonehamMA02180
Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.
43 Pomeworth St
StonehamMA02180
7 Harris Cir
ArlingtonMA02474
26 Heath Rd
ArlingtonMA02474
19 Arizona Ter, Unit 4
19 Arizona Ter
ArlingtonMA02474
19 Arizona Ter
ArlingtonMA02474
4 Brattle Dr
ArlingtonMA02474
17 Arizona Ter, Unit 11
17 Arizona Ter
ArlingtonMA02474
2 Elmwood Ave
WinchesterMA01890
2 Elmwood Ave
WinchesterMA01890
2 Elmwood Ave
WinchesterMA01890
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
14 Dudley St, Unit 6
14 Dudley St
ArlingtonMA02476
7 Brattle Dr, Unit 1
7 Brattle Dr
ArlingtonMA02474
11 Brattle Dr
ArlingtonMA02474
200 Swanton St
WinchesterMA01890
4 Nixon Ln, Unit 1W
4 Nixon Ln
StonehamMA02180
2 Elmwood Ave
WinchesterMA01890
898 Massachusetts Ave
ArlingtonMA02476
16 Old Colony Ln, Unit 12
16 Old Colony Ln
ArlingtonMA02476
3 Old Colony Ln, Unit 8
3 Old Colony Ln
ArlingtonMA02476
12 Brattle Dr
ArlingtonMA02474
49 Broadway, Unit #6
49 Broadway
ArlingtonMA02474
9 Wildwood Rd
MedfordMA02155
35 Prospect St
WoburnMA01801
1 Brattle Dr
ArlingtonMA02474
215 Massachusetts Ave
ArlingtonMA02474
12 Brattle Dr
ArlingtonMA02474
1 Brattle Dr
ArlingtonMA02474
14 Brattle Ln, Unit 31
14 Brattle Ln
ArlingtonMA02474
94 Harlow St
ArlingtonMA02474
12 Totman Dr
WoburnMA01801
7 Arizona Ter, Unit 2
7 Arizona Ter
ArlingtonMA02474
35 Vine St
WinchesterMA01890
385 Massachusetts Ave
ArlingtonMA02474
1 Watermill Pl
ArlingtonMA02476
79 Capen St
MedfordMA02155
27 Arlington Rd, Unit 5
27 Arlington Rd
WoburnMA01801
31 Arlington Rd, Unit 5
31 Arlington Rd
WoburnMA01801
114 Pleasant St
ArlingtonMA02476
22 Hamilton Rd, Unit #106
22 Hamilton Rd
ArlingtonMA02474
112 Decatur St
ArlingtonMA02474
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 | $3,023 | $2,300 | $4,200 |
| Winchester 3 Bedroom Homes for Rent | $3,933 | $3,000 | $6,900 |
| Winchester 4 Bedroom Homes for Rent | $4,955 | $3,425 | $10,000+ |
| Winchester 5 Bedroom Homes for Rent | $6,472 | $4,225 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $7,793 | $5,500 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $8,997 | $6,995 | $10,000+ |
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 26, 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 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 |
| 67 Forest St, Unit 235 | 67 Forest St | 1BR,1BA | $0.23 |
| 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 932 Apartments for Rent in Winchester, MA with pricing that ranges from $1,300 to $11,077. There are also 502 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,750 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 $1,750 to $25,000 with an average monthly rent of $4,932.
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 $2,800 to $11,077, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 to $6,900. Four Bedroom Single-Family rentals are also available starting from $3,425 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.
Rise of Digital Nomads: Remote Work Tips for Apartment Renters
Written by: Brandie Parton
As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.
Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Written by: Christine Leonard, Esq.
Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.