close
View Me
$7,0005 Bedroom Apartments Available Jun 1, 2027
34 George St
34 George StMedford, MA 02155
Apartments for Rent in Winchester, MA (542 Rentals) Page 6 of 11
close
View Me
$4,3505 Bedroom Apartments Available Now
249 Boston Ave, Unit 3
249 Boston AveMedford, MA 02155
close
View Me
$3,3903 Bedroom Apartments Available Sep 1
127 Hillsdale Rd
127 Hillsdale RdSomerville, MA 02144
close
View Me
$3,3003 Bedroom Apartments Available Sep 1
333 Alewife Brook Pkwy, Unit 2
333 Alewife Brook PkwySomerville, MA 02144
close
View Me
$4,2003 Bedroom Apartments Available Jun 1, 2027
2 High St
2 High StSomerville, MA 02144
close
View Me
$3,2003 Bedroom Apartments Available Sep 1
111 North St, Unit 2
111 North StSomerville, MA 02144
close
View Me
$3,7003 Bedroom Apartments Available Jun 1, 2027
102 W Adams St, Unit 1
102 W Adams StSomerville, MA 02144
close
View Me
$3,6003 Bedroom Apartments Available Now
14 Belknap St, Unit 2
14 Belknap StSomerville, MA 02144
close
View Me
$7,2006 Bedroom Apartments Available Jun 1, 2027
109 North St
109 North StSomerville, MA 02144
close
View Me
$8,4006 Bedroom Apartments Available Jun 1, 2027
146 W Adams St
146 W Adams StSomerville, MA 02144
close
View Me
$5,8004 Bedroom Apartments Available Jun 1, 2027
22 Curtis Ave, Unit 2
22 Curtis AveSomerville, MA 02144
close
View Me
$7,5005 Bedroom Apartments Available Jun 1, 2027
185 Powder House Blvd, Unit 2
185 Powder House BlvdSomerville, MA 02144
close
View Me
$4,5003 Bedroom Apartments Available Jun 1, 2027
185 Powder House Blvd, Unit 1
185 Powder House BlvdSomerville, MA 02144
close
View Me
$7,2005 Bedroom Apartments Available Jun 1, 2027
15 Curtis Ave, Unit 2
15 Curtis AveSomerville, MA 02144
close
View Me
$5,7004 Bedroom Apartments Available Jun 1, 2027
15 Curtis Ave, Unit 1
15 Curtis AveSomerville, MA 02144
close
View Me
$5,4004 Bedroom Apartments Available Jun 1, 2027
36 Sunset Rd, Unit 2
36 Sunset RdSomerville, MA 02144
close
View Me
$4,1004 Bedroom Apartments Available Sep 1
27 Fairfax St, Unit 2
27 Fairfax StSomerville, MA 02144
close
View Me
$4,0004 Bedroom Apartments Available Sep 1
27 Fairfax St, Unit 1
27 Fairfax StSomerville, MA 02144
close
View Me
$5,6004 Bedroom Apartments Available Jun 1, 2027
24 Chetwynd Rd, Unit 1
24 Chetwynd RdSomerville, MA 02144
6 Wildwood Ln
StonehamMA02180
16 Walnut St
ArlingtonMA02476
119 Burget Ave
MedfordMA02155
1 Lincoln St
StonehamMA02180
390 Massachusetts Ave
LexingtonMA02420
65 Winn St
WoburnMA01801
1080 Massachusetts Ave
ArlingtonMA02476
2 Peabody Rd
StonehamMA02180
754 Massachusetts Ave
LexingtonMA02420
80 Cambridge Rd
WoburnMA01801
32 Paul Revere Rd
ArlingtonMA02476
49 Prospect St
WoburnMA01801
53 Oakland St
MedfordMA02155
79 Curtis St
SomervilleMA02144
283 Alewife Brook Pkwy
SomervilleMA02144
46-48-48 Cleveland St
ArlingtonMA02474
2500 Mystic Valley Pkwy
MedfordMA02155
154 Summer St
ArlingtonMA02474
32 Century St
MedfordMA02155
1357 Massachusetts Ave
ArlingtonMA02476
51 Winter St
ArlingtonMA02474
87 Woods Ave
SomervilleMA02144
245 Broadway
ArlingtonMA02474
118-120 Paul Revere Rd
ArlingtonMA02476
32 Gourley Rd
MedfordMA02155
167 Summer St
ArlingtonMA02474
129 Madison Ave
ArlingtonMA02474
34 George St
MedfordMA02155
930 Massachusetts Ave
ArlingtonMA02476
19-21-21 Mt Vernon St
ArlingtonMA02476
17 Governors Ave
MedfordMA02155
Showing Results 251-300, Page 6 of 11
Winchester, MA Local Guide
How much does it cost to rent an apartment in Winchester?
| 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 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Apartments in Winchester
Explore Winchester
Let everyone know!
Do you know the Winchester area?
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 Review
Frequently Asked Questions about Winchester
What is the current pricing and availability for apartments for rent in Winchester, MA?
As 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.
What Winchester neighborhoods have the most available apartments?
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.
How much are Studio apartments in Winchester?
There are currently 103 Studio Apartments in Winchester with rent ranges from $1,725 to $3,350 with an average price of $2,381.
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 $825 to $4,070 with an average monthly rent of $2,611.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $1,100 to $5,441. Today's average rental price for Two Bedrooms here is $3,265.
How expensive are Winchester Three Bedroom Apartments?
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.
Expert Rental Resources
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.
Helpful Local Expert Guides
Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
What It Really Costs to Live in Boston: A Local Renter's Guide
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com expert for Boston!
Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert
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!
Articles, How-To's, and Tips
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
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.
First Apartment Regrets: Real Renters Share What They'd Do Differently
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.
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
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.
Apartment Occupancy Rates: Renter Attraction vs Renter Retention
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.