
Luxury Homes for Rent in Winchester, MA (470 Rentals)Page 5 of 10
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.


19 Sunset Rd

32 Chetwynd Rd, Unit 2

2 Osgood St, Unit 3

35 Bowdoin St, Unit 35

112 College Ave, Unit U2

6 Rolfe Rd

278 Gray St

120 Massachusetts Ave

2 Swan St

2004 Symmes Cir

80 Quincy St

82 Quincy St, Unit 2

82 Quincy St, Unit 2

14 Barton St, Unit 2

1 Victoria St, Unit 2

6 Perth Rd

6 Perth Rd

201 Winn St

32 Washington St

52 Webster St, Unit 52

100 W Adams St

50 Curtis Ave, Unit 1

10 Greenleaf Ave

266 Boston Ave, Unit 2

50 Curtis Ave, Unit 1

77 Lyman Ave

33 Grafton St, Unit 2

21 Mount Vernon St, Unit 1

221 Boston Ave, Unit 2

227 Boston Ave

215 Boston Ave, Unit 2

119 Burget Ave, Unit 2

217 Boston Ave, Unit #2

217 Boston Ave, Unit 2

217 Boston Ave, Unit 2

217 Boston Ave

3 Hamilton Rd

227 Boston Ave, Unit 2

10 Pinkham Rd, Unit Pinkham rd

10 Pinkham Rd, Unit 2

32 River St

308 Washington St

10 Pinkham Rd, Unit 2

48 Crosby St

27 Michael St

10 Pinkham Rd

10 Pinkham Rd, Unit 2

48 Newcomb St, Unit 48

10 Pinkham Rd, Unit 2
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 | $2,959 | $2,300 | $4,000 |
Winchester 3 Bedroom Homes for Rent | $3,952 | $2,800 | $7,200 |
Winchester 4 Bedroom Homes for Rent | $4,913 | $3,200 | $7,250 |
Winchester 5 Bedroom Homes for Rent | $6,200 | $2,800 | $10,000+ |
Winchester 6 Bedroom Homes for Rent | $7,973 | $5,500 | $10,000+ |
Winchester 7 Bedroom Homes for Rent | $7,975 | $7,975 | $7,975 |
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 998 Apartments for Rent in Winchester, MA with pricing that ranges from $1,100 to $11,187. There are also 507 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,800 to $25,000.
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 $1,800 to $25,000 with an average monthly rent of $4,808.
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 $2,600 to $11,187, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $7,200. Four Bedroom Single-Family rentals are also available starting from $3,200 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.

Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.

Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.