
4 Bedroom Luxury Apartments for Rent in Winchester, MA (298 Rentals)


80 Orchard St, Unit Apt 2

62 Woods Ave, Unit 2

112 College Ave, Unit U2

37 Sterling St, Unit #2
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

3 Hamilton Rd, Unit #2

37 Sterling St, Unit 2

3 Hamilton Rd, Unit 2

16 Chetwynd Rd, Unit 2

10 Greenleaf Ave, Unit 1

1 Victoria St, Unit 2
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.

1 Victoria St, Unit 2

217 Arlington St, Unit 1

314 Massachusetts Ave, Unit 2

3 Hamilton Rd, Unit PH

2 Hamilton Rd, Unit 2

12 Raymond Ave, Unit 1

314 Massachusetts Ave

476 Fulton St, Unit T

17 Tesla Ave, Unit #2

136 Burget Ave

476 Fulton St, Unit T

476 Fulton St, Unit A
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.

3 Hamilton Rd, Unit 2

232 Fulton St, Unit A

232 Fulton St, Unit T

25 Belknap St, Unit 1

1 Victoria St, Unit 2

314 Massachusetts Ave, Unit 2

3 Hamilton Rd, Unit 2

24 Belknap St, Unit 3

1 Victoria St, Unit 2T
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

1 Victoria St, Unit 2A

314 Massachusetts Ave, Unit 2

64 Chetwynd Rd, Unit 2

50 Curtis Ave, Unit 1

127 Monument St, Unit 1

299 Alewife Brook Pky, Unit 2

128 Monument St

120 Jerome St

232 Fulton St, Unit 1
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 | $2,176 | $1,300 | $5,256 |
Winchester 1 Bedroom Apartments | $2,594 | $1,020 | $6,923 |
Winchester 2 Bedroom Apartments | $3,296 | $1,750 | $8,856 |
Winchester 3 Bedroom Apartments | $3,747 | $2,800 | $7,500 |
Winchester 4 Bedroom Apartments | $4,407 | $3,000 | $5,750 |
Winchester 5 Bedroom Apartments | $5,325 | $4,000 | $6,900 |
Winchester 6 Bedroom Apartments | $6,860 | $4,500 | $9,900 |
Explore Winchester
Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
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Quick Rent Budget Calculator
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.
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 37 Studio Apartments in Winchester with rent ranges from $1,300 to $5,256 with an average price of $2,176.
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 $1,020 to $6,923 with an average monthly rent of $2,594.
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 $8,856. Today's average rental price for Two Bedrooms here is $3,296.
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 $7,500 - averaging $3,747 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.

The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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.