
Luxury Homes for Rent in Winchester, MA (461 Rentals)Page 7 of 10
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.


990 Massachusetts Ave, Unit #75

51 Conn St

990 Massachusetts Ave, Unit 75

29 Harvard Ave, Unit 33

100 High St, Unit 505

991 Massachusetts Ave

333 Alewife Brook Pky

1 Victoria St, Unit 1A

1 Victoria St, Unit 1A

37 Clark St

56 Gordon St, Unit 1

81 College Ave, Unit 2

20 Burget Ave

20 Burget Ave, Unit T

4 Golden Ct, Unit 2

16 Orchard St

26 Bradlee Rd

349 Boston Ave

66 North St, Unit 1

139 Hillsdale Rd, Unit 2

53 Fairfax St, Unit 1

34 Holton St, Unit 1

50 Water St, Unit 25

220 Massachusetts Ave, Unit 2

24 South St, Unit 36

1180 Massachusetts Ave, Unit C

12 Water St, Unit 1

400 Massachusetts Ave, Unit 4

75 Mystic St, Unit 3

25 Arlington Rd, Unit 3

9 Circuit St, Unit 1

121 Cambridge Rd, Unit B2

121 Cambridge Rd, Unit 2

12 Conwell Ave

22 High St, Unit 11

10 Pine Ave, Unit 10

289 Elm St, Unit 14

117 Hillsdale Rd
Winchester, MA Local Guide

How much does it cost to rent a home in Winchester?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Winchester 2 Bedroom Homes for Rent | $3,133 | $2,375 | $6,400 |
Winchester 3 Bedroom Homes for Rent | $3,865 | $3,000 | $6,550 |
Winchester 4 Bedroom Homes for Rent | $4,915 | $3,425 | $7,500 |
Winchester 5 Bedroom Homes for Rent | $6,452 | $4,225 | $10,000+ |
Winchester 6 Bedroom Homes for Rent | $7,848 | $4,850 | $10,000+ |
Winchester 7 Bedroom Homes for Rent | $8,497 | $6,995 | $10,000+ |
Browse Top Homes for Rent in Winchester
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Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 810 Apartments for Rent in Winchester, MA with pricing that ranges from $955 to $10,400. There are also 504 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,650 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 $1,650 to $40,000 with an average monthly rent of $4,878.
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 $2,800 to $7,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 to $6,550. Four Bedroom Single-Family rentals are also available starting from $3,425 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.

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.