
Luxury Homes for Rent in Winchester, MA (446 Rentals)Page 5 of 9
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.


82 Quincy St, Unit 2

100 W Adams St

62 Woods Ave

64 Woods Ave

50 Curtis Ave, Unit 1

10 Greenleaf Ave

266 Boston Ave, Unit 2

50 Curtis Ave, Unit 1

77 Lyman Ave

1 Victoria St, Unit 2

1 Victoria St, Unit 2

1 Victoria St, Unit 2

221 Boston Ave, Unit 2

227 Boston Ave

119 Burget Ave, Unit 2

217 Boston Ave, Unit 2

3 Hamilton Rd

30 Touro Ave

130 Capen St, Unit 130

12 Upland Rd

2012 Symmes Cir, Unit 1

10 Pinkham Rd, Unit 2

10 Pinkham Rd, Unit 2

10 Pinkham Rd, Unit 2

59 Quincy St, Unit 1

10 Pinkham Rd, Unit 2

59 Quincy St

10 Pinkham Rd, Unit 2

7 Hillside Ave, Unit 3

10 Pinkham Rd, Unit 2

12 Bellevue St, Unit 1

49 Adams St, Unit 49

50 Hamilton St, Unit 2

50 Hamilton St

44 Upland Rd, Unit 1

59 Quincy St

32 Irvington Rd

56 Gordon St

56 Gordon St, Unit 2

59 Quincy St, Unit 59

30 Chetwynd Rd, Unit 1

59 Quincy St, Unit 1

290 Boston Ave, Unit 2

59 Quincy St

32 Irvington Rd

21 Belknap St, Unit 2

17 University Ave, Unit 17

15 Taylor St, Unit 1

47 Webster St, Unit 47
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 | $3,145 | $2,375 | $6,400 |
Winchester 3 Bedroom Homes for Rent | $3,860 | $3,000 | $5,950 |
Winchester 4 Bedroom Homes for Rent | $4,912 | $3,425 | $7,500 |
Winchester 5 Bedroom Homes for Rent | $6,412 | $4,225 | $10,000+ |
Winchester 6 Bedroom Homes for Rent | $7,848 | $4,850 | $10,000+ |
Winchester 7 Bedroom Homes for Rent | $8,997 | $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 806 Apartments for Rent in Winchester, MA with pricing that ranges from $955 to $10,400. There are also 497 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 $4,957.
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 $5,950. 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.