
Luxury Homes for Rent in Winchester, MA (435 Rentals)Page 6 of 9
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.


2 High St, Unit 2

2 High St, Unit 1

59 Quincy St

59 Quincy St

10 Pinkham Rd, Unit #2

10 Pinkham Rd, Unit 2

49 Conwell Ave

49 Conwell Ave, Unit 2

49 Conwell Ave, Unit 2

49 Conwell Ave, Unit 2

49 Conwell Ave, Unit #2

112 College Ave, Unit 1

49 Conwell Ave, Unit Conwell Ave

28 Wadsworth Rd

91 Williams St, Unit 91

75 Lyman Ave

7 Greenleaf Ave, Unit 1

227 Boston Ave, Unit 1

81 Conwell Ave, Unit 3

45 Orchard St, Unit #0

8 Vera Ln

1 Victoria St

34 Metcalf St, Unit 2

1 Victoria St, Unit 1A

116 Medford St, Unit 1

1 Victoria St, Unit 1A

67 Sterling St

67 Sterling St

258 Boston Ave, Unit 2

258 Boston Ave, Unit 2

258 Boston Ave, Unit 2

32-34 Fessenden Rd, Unit 2

132 Broadway, Unit 1

9 Brookings St, Unit 2

104 Forest St

104 Forest St

104 Forest St, Unit 104

1 Victoria St

9 Gregg St

40 Hamilton St, Unit 2

40 Hamilton St, Unit 2

100 High St, Unit 505

26 Bradlee Rd

100 High St, Unit 505

100 High St, Unit 505

12 Hayes St, Unit 1

37 Westminster Ave, Unit 2

100 High St, Unit 505

15 Patrick St, 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 | $2,940 | $2,300 | $4,000 |
Winchester 3 Bedroom Homes for Rent | $3,912 | $2,800 | $7,200 |
Winchester 4 Bedroom Homes for Rent | $4,875 | $3,200 | $7,250 |
Winchester 5 Bedroom Homes for Rent | $6,169 | $2,800 | $10,000+ |
Winchester 6 Bedroom Homes for Rent | $7,748 | $5,500 | $10,000+ |
Winchester 7 Bedroom Homes for Rent | $11,000 | $10,000 | $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 984 Apartments for Rent in Winchester, MA with pricing that ranges from $1,100 to $11,187. There are also 476 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 $5,142.
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.