
Luxury Homes for Rent in Winchester, MA (446 Rentals)Page 3 of 9
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.


14 Fairmount St

76 Curtis St

14 Fairmount St

3 Hamilton Rd, Unit #2

3 Hamilton Rd, Unit 2

3 Hamilton Rd, Unit 2

76 Curtis St, Unit 1

22 Harris Rd, Unit 2

476 Fulton St

477 Fulton St, Unit T

476 Fulton St, Unit 476

3 Hamilton Rd, Unit 2

476 Fulton St

3 Hamilton Rd, Unit 2

3 Hamilton Rd, Unit 2

3 Hamilton Rd, Unit 2

3 Hamilton Rd, Unit 2

3 Hamilton Rd

5 Hamilton Rd

8 Hamilton Rd

217 Arlington, Unit 1

217 Arlington St

217 Arlington St, Unit 1

217 Arlington St, Unit 1

215 Arlington St, Unit 1

217 Arlington St

217 Arlington St, Unit 1

217 Arlington St

215 Arlington St

207 Arlington St

76 Curtis St, Unit 1

123 Winthrop St

298 Mystic St

76 Curtis St, Unit 1

476 Fulton St

23 Ames Ave

12 Upland Rd, Unit 1

29 Chetwynd Rd, Unit 2

19 Sunset Rd, Unit 19

476 Fulton St

476 Fulton St

482 Fulton St

480 Fulton St, Unit 478

476 Fulton St

476 Fulton St

479 Fulton St

217 Arlington St

64 Chetwynd Rd, Unit 1

10 Greenleaf Ave, Unit 1
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.