39 Belknap St, Unit 2
39 Belknap St
SomervilleMA02144
Luxury Homes for Rent in Winchester, MA (286 Rentals) Page 3 of 6
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.
625 Summer St
ArlingtonMA02474
483 Broadway
MedfordMA02155
483 Broadway
MedfordMA02155
11 Mead Rd
ArlingtonMA02474
91 Williams St, Unit 91
91 Williams St
ArlingtonMA02476
625 Summer St
ArlingtonMA02474
21 Jerome St
MedfordMA02155
32 Irvington Rd
SomervilleMA02144
49 Conwell Ave, Unit 2
49 Conwell Ave
SomervilleMA02144
5 Harris Rd, Unit 1
5 Harris Rd
MedfordMA02155
21A Mystic River Rd
MedfordMA02155
18 Moulton Rd
ArlingtonMA02476
77 Adams St
MedfordMA02155
52 Westwood Rd
StonehamMA02180
52 Westwood Rd
StonehamMA02180
107 Spring St
StonehamMA02180
close
View Me
38 Norwich Cir
MedfordMA02155
94 North St
SomervilleMA02144
94 North St, Unit 94
94 North St
SomervilleMA02144
94 North St
SomervilleMA02144
25 Bailey St
SomervilleMA02144
close
View Me
$3,700
Plus Fees
4 Bedroom Apartments Available Jun 1, 2026248 Powder House Blvd
248 Powder House BlvdSomerville, MA 02144
close
View Me
$3,750
Plus Fees
3 Bedroom Apartments Available Jun 1, 2026258 Boston Ave
258 Boston AveMedford, MA 02155
10 Carson Rd
WoburnMA01801
293 Boston Ave, Unit 2
293 Boston Ave
MedfordMA02155
15 Taylor St
MedfordMA02155
47 Webster St, Unit 47
47 Webster St
ArlingtonMA02474
94 North St
SomervilleMA02144
555 Main St
WoburnMA01801
59 Quincy St, Unit 59
59 Quincy St
MedfordMA02155
56 Gordon St, Unit 2
56 Gordon St
SomervilleMA02144
32 Irvington Rd
SomervilleMA02144
59 Quincy St
MedfordMA02155
469 Appleton St
ArlingtonMA02476
40 Brattle St
ArlingtonMA02476
18 Cranston Cir
WoburnMA01801
8 Greenleaf Ave
MedfordMA02155
28 Webster St
MedfordMA02155
18 Arthur G Pernokas Dr
WoburnMA01801
close
View Me
$4,000
Plus Fees
4 Bedroom Apartments Available Jun 1, 202614.5 Fairmount St
14.5 Fairmount StMedford, MA 02155
62 Woods Ave
SomervilleMA02144
10 Pinkham Rd, Unit 2
10 Pinkham Rd
MedfordMA02155
148 George St, Unit 2
148 George St
MedfordMA02155
2012 Symmes Cir, Unit 1
2012 Symmes Cir
ArlingtonMA02474
12 Upland Rd
SomervilleMA02144
10 Pinkham Rd, Unit 2
10 Pinkham Rd
MedfordMA02155
17 Bowman St
LexingtonMA02421
17 Bowman St
LexingtonMA02421
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 Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $2,997 | $2,075 | $5,700 |
| Winchester 3 Bedroom Homes for Rent | $3,878 | $1,200 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $5,151 | $3,300 | $8,000 |
| Winchester 5 Bedroom Homes for Rent | $6,866 | $4,200 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $9,392 | $6,200 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Homes for Rent 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 type of rentals are currently available in Winchester?
There are currently 533 Apartments for Rent in Winchester, MA with pricing that ranges from $1,200 to $9,300. There are also 342 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,100 to $40,000.
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 $1,100 to $40,000 with an average monthly rent of $4,642.
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 $2,500 to $6,900, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,200 to $20,000. Four Bedroom Single-Family rentals are also available starting from $3,300 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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.