Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.
Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.
Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.
Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead
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.
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Studio Apartments | $2,381 | $1,725 | $3,350 |
| Winchester 1 Bedroom Apartments | $2,611 | $825 | $4,070 |
| Winchester 2 Bedroom Apartments | $3,265 | $1,100 | $5,441 |
| Winchester 3 Bedroom Apartments | $3,776 | $2,500 | $6,471 |
| Winchester 4 Bedroom Apartments | $4,651 | $3,200 | $6,750 |
| Winchester 5 Bedroom Apartments | $6,853 | $4,350 | $10,000+ |
| Winchester 6 Bedroom Apartments | $7,195 | $1,000 | $9,600 |
If you’re an expert on all things Winchester, tell us what you love (and don't) by rating it and writing a review.
Write a ReviewAs of today, August 29, 2026, there are currently 542 available Winchester apartments priced from $825 to $19,900, with an average monthly rent of $3,446.
There are 3 neighborhoods in the Winchester area with available listings as of today. The three neighborhoods with the most options are Kendall Square with 5,841 listings, West End Boston with 5,203 listings, and North Station with 4,692 listings.
There are currently 103 Studio Apartments in Winchester with rent ranges from $1,725 to $3,350 with an average price of $2,381.
Today's rental pricing for One Bedroom Apartments in Winchester ranges from $825 to $4,070 with an average monthly rent of $2,611.
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $1,100 to $5,441. Today's average rental price for Two Bedrooms here is $3,265.
There are currently 95 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,500 to $6,471 - averaging $3,776 for the location.
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.
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com expert for Boston!
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com expert for Boston, and I’m excited to help you find your next home!
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.
We'll check your Winchester review to ensure it meets our Review Guidelines.
Thank you!
