
Luxury Homes for Rent in Winchester, MA (448 Rentals)Page 7 of 9
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.


104 Forest St

104 Forest St

104 Forest St, Unit 104

132 Broadway, Unit 1

40 Hamilton St, Unit 2

40 Hamilton St, Unit 2

26 Bradlee Rd

100 High St, Unit 505

100 High St, Unit 505

37 Westminster Ave, Unit 2

12 Hayes St, Unit 1

100 High St, Unit 505

26 Bradlee Rd, Unit 102

1500 Massachusetts Ave, Unit 1

991 Massachusetts Ave

991 Massachusetts Ave

333 Alewife Brook Pky

333 Alewife Brook Pky, Unit 1

1 Victoria St, Unit 1A

37 Clark St

81 College Ave, Unit 2

4 Golden Ct, Unit 2

43 Orchard St, Unit #0

78 Warren St, Unit 1

20 Burget Ave, Unit T

20 Burget Ave

26 Bradlee Rd, Unit #402

16 Orchard St

349 Boston Ave

26 Bradlee Rd

139 Hillsdale Rd, Unit 2

21 Taft St, Unit 1

53 Fairfax St, Unit 1

34 Holton St, Unit 1

25 Arlington Rd, Unit 3

26 Bradlee Rd, Unit 1

1180 Massachusetts Ave, Unit C

12 Water St, Unit 1

400 Massachusetts Ave, Unit 4

75 Mystic St, Unit 3

64 Main St, Unit 32B

32-34 Fessenden Rd, Unit 3

101 Boston Ave, Unit Boston Ave

9 Circuit St, Unit 1

101 Boston Ave, Unit #1

121 Cambridge Rd, Unit B2

22 Hamilton Rd, Unit #106

125 Pleasant St, Unit 401

4 Colonial Village Dr, Unit 11
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 | $2,992 | $2,300 | $4,200 |
Winchester 3 Bedroom Homes for Rent | $3,972 | $3,000 | $7,200 |
Winchester 4 Bedroom Homes for Rent | $4,837 | $3,200 | $7,360 |
Winchester 5 Bedroom Homes for Rent | $6,594 | $4,200 | $10,000+ |
Winchester 6 Bedroom Homes for Rent | $7,841 | $5,500 | $10,000+ |
Winchester 7 Bedroom Homes for Rent | $9,487 | $7,975 | $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 956 Apartments for Rent in Winchester, MA with pricing that ranges from $1,100 to $11,037. There are also 483 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,750 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 $1,750 to $25,000 with an average monthly rent of $4,999.
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 $2,700 to $11,037, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 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.

Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Written by: Christine Leonard, Esq.
Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.

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.