4 Bedroom Apartments for Rent in Winchester, MA (311 Rentals)

37 Sterling St, Unit #2

3 Hamilton Rd, Unit #2

37 Sterling St, Unit 2

10 Greenleaf Ave, Unit 1

3 Hamilton Rd, Unit 2

217 Arlington St, Unit 1
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

16 Chetwynd Rd, Unit 2

1 Victoria St, Unit 2

1 Victoria St, Unit 2

476 Fulton St, Unit T

3 Hamilton Rd, Unit PH

2 Hamilton Rd, Unit 2

17 Tesla Ave, Unit #2

476 Fulton St, Unit A

12 Raymond Ave, 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.

136 Burget Ave

476 Fulton St, Unit T

232 Fulton St, Unit T

232 Fulton St, Unit A

3 Hamilton Rd, Unit 2

25 Belknap St, Unit 1

1 Victoria St, Unit 2

1 Victoria St, Unit 2A

1 Victoria St, Unit 2T
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.

314 Massachusetts Ave, Unit 2

3 Hamilton Rd, Unit 2

127 Monument St, Unit 1

24 Belknap St, Unit 3

314 Massachusetts Ave

128 Monument St

120 Jerome St

64 Chetwynd Rd, Unit 2

50 Curtis Ave, Unit 1

232 Fulton St, Unit 1
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

299 Alewife Brook Pky, Unit 2

299 Alewife Brook Pky, Unit 2T

476 Fulton St, Unit 1

120 Jerome St, Unit 1

217 Arlington St, Unit 1

314 Massachusetts Ave, Unit 2

314 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 |
---|---|---|---|
Winchester Studio Apartments | $2,159 | $1,595 | $2,850 |
Winchester 1 Bedroom Apartments | $2,640 | $1,450 | $7,415 |
Winchester 2 Bedroom Apartments | $3,298 | $1,750 | $9,644 |
Winchester 3 Bedroom Apartments | $3,769 | $2,800 | $8,000 |
Winchester 4 Bedroom Apartments | $4,467 | $3,000 | $5,750 |
Winchester 5 Bedroom Apartments | $5,405 | $4,000 | $7,800 |
Winchester 6 Bedroom Apartments | $6,897 | $5,990 | $9,900 |
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Winchester, MA Local Guide
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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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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 Winchester
How much are Studio apartments in Winchester?
There are currently 35 Studio Apartments in Winchester with rent ranges from $1,595 to $2,850 with an average price of $2,159.
What is the current price range for One Bedroom Winchester Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Winchester ranges from $1,450 to $7,415 with an average monthly rent of $2,640.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $1,750 to $9,644. Today's average rental price for Two Bedrooms here is $3,298.
How expensive are Winchester Three Bedroom Apartments?
There are currently 175 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,800 to $8,000 - averaging $3,769 for the location.
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.

Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.

Navigating the Rental Market: Tips for First-Time Renters
Written by: Sandy Baker
Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.