
Luxury Homes for Rent in Winchester, MA (251 Rentals) Page 3 of 6
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.


38 George St

14 Belknap St, Unit 1, Unit 1

2 High St, Unit 1, Unit 1

7 Carol St

58 Conwell Ave

62 Newport St, Unit 2

149 North St, Unit 1, Unit 1

212 Cambridge Rd

15 Taylor St, Unit 1B

15 Taylor St, Unit #1

15 Taylor St, Unit 1

56 Gordon St, Unit 1, Unit 1

59 Quincy St, Unit 59, Unit 59

56 Gordon St, Unit 2, Unit 2

32 Irvington Rd

30 Adams St, Unit 2

2012 Symmes Cir, Unit 1, Unit 1

34 Sunset Rd, Unit 2, Unit 2

11 Woodbury St

99 Garfield Ave

45 Lyman Ave

3 Hamilton Rd

19 Adams St

63 Foster St

1 Victoria St, Unit 2, Unit 2

89 Sherwood Rd

33 Chetwynd Rd, Unit 2, Unit 2

30 Touro Ave

50 Curtis Ave

288 Boston Ave

33 Chetwynd Rd, Unit 2

11 Garfield Ave

27 Fairfax St, Unit 1

123 Winthrop St

123 Winthrop St

30 Touro Ave, Unit 1, Unit 1

3 Greenview Rd

8 Hamilton Rd

171 Forest St, Unit SF, Unit SF

1 College Ave

227 Boston Ave, Unit 2

22 James St

27 Fairfax St, Unit 2

476 Fulton St, Unit Unit 2, Unit Unit 2

62 Woods Ave

18 Charles St

14-16 Hamilton Rd, Unit 14

14 Barton St, Unit 2, Unit 2

2 Osgood St, Unit 1, Unit 1
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 | $2,987 | $2,299 | $4,500 |
| Winchester 3 Bedroom Homes for Rent | $4,209 | $2,600 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $4,886 | $3,100 | $7,900 |
| Winchester 5 Bedroom Homes for Rent | $6,894 | $1,250 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,526 | $5,497 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $8,800 | $5,600 | $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 474 Apartments for Rent in Winchester, MA with pricing that ranges from $1,110 to $12,929. There are also 313 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,250 to $28,000.
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 $1,250 to $28,000 with an average monthly rent of $5,062.
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 $6,034, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $16,000. Four Bedroom Single-Family rentals are also available starting from $3,100 and Four Bedroom Apartments start at $3,100.
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

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This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

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This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

Maximizing Your Refund: Essential Tax Tips for Renters
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Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
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Renting your next home can feel thrilling and overwhelming at the same time.