
Luxury Homes for Rent in Winchester, MA (230 Rentals) Page 5 of 5
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.


34 George St

15 Campbell Rd

15 Curtis Ave, Unit 2

15 Campbell Rd

98 W Quincy St, Unit S

16 Curtis Ave, Unit 2

109 North St

23 Edison Ave, Unit 1

120 Jerome St

185 Powder House Blvd, Unit 2

17 Tesla Ave

17 Tesla Ave, Unit 1

107 North St

4 High St

9 Richard Rd

98 W Quincy St, Unit J

146 W Adams St

53 Old Mystic St

76 Canal St

45 Wellesley Rd

45 Wellesley Rd

83 Irving St

22 Hillsdale Rd

25 Falmouth Rd

Total Monthly Price
64 Newcomb Rd, Unit SI FL4-ID1586668P

98 W Quincy St

64 Newcomb Rd

29 Hayes Ln

12 Summit Rd
Winchester, MA Local Guide

How much does it cost to rent a home in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $2,996 | $1,000 | $4,750 |
| Winchester 3 Bedroom Homes for Rent | $3,912 | $2,800 | $6,500 |
| Winchester 4 Bedroom Homes for Rent | $5,150 | $3,450 | $8,750 |
| Winchester 5 Bedroom Homes for Rent | $8,353 | $4,750 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $9,609 | $6,495 | $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 445 Apartments for Rent in Winchester, MA with pricing that ranges from $825 to $18,885. There are also 283 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $800 to $18,000.
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 $800 to $18,000 with an average monthly rent of $4,028.
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 $2,500 to $6,718, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $6,500. Four Bedroom Single-Family rentals are also available starting from $3,450 and Four Bedroom Apartments start at $2,900.
Expert Rental Resources
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.
Helpful Local Expert Guides

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Articles, How-To's, and Tips

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.