
Homes for Rent in Winchester, MA (273 Rentals) Page 2 of 6


151 Walsh St

124 Forest St, Unit 1, Unit 1

48 Forest St, Unit 106, Unit 106

93 Capen St, Unit 2, Unit 2

5 Harris Rd

77 Lyman Ave, Unit 2, Unit 2

38 George St, Unit 1, Unit 1

38 George St

59 Quincy St, Unit 59, Unit 59
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

45 Lyman Ave

89 Sherwood Rd

123 Winthrop St

123 Winthrop St

171 Forest St, Unit SF, Unit SF

476 Fulton St

476 Fulton St

14 Fairmount St

355 Boston Ave, Unit 1, Unit 1

476 Fulton St

10 Pinkham Rd, Unit 2##, Unit 2##

217 Arlington St

480 Fulton St, Unit 478, Unit 478

217 Arlington St, Unit 1, Unit 1

217 Arlington St

476 Fulton St, Unit 476, Unit 476

57 Quincy St, Unit 57, Unit 57

112 College Ave, Unit 87, Unit 87

136 Burget Ave

120 Jerome St

232 Fulton St, Unit 2, Unit 2

128 Monument St, Unit 126, Unit 126

120 Jerome St

120 Jerome St

120 Jerome St

140 Jerome St

128 Monument St

120 Jerome St

120 Jerome St

120 Jerome St, Unit 1, Unit 1

232 Fulton St, Unit 232, Unit 232

120 Jerome St, Unit 120, Unit 120

232 Fulton St, Unit T, Unit T

14 Sturtevant Ter, Unit 1, Unit 1

157 Franklin St, Unit A11, Unit A11

39 Cottage St, Unit 1, Unit 1

36 Gould St

64 Newcomb Rd

92 Emerson Gardens Rd

17 Dow St
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 | $3,001 | $2,299 | $4,900 |
| Winchester 3 Bedroom Homes for Rent | $4,160 | $2,600 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $4,928 | $3,300 | $7,950 |
| Winchester 5 Bedroom Homes for Rent | $7,323 | $1,275 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,488 | $5,497 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $12,000 | $10,000 | $10,000+ |
Browse Top Homes for Rent in Winchester
Explore Winchester
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 480 Apartments for Rent in Winchester, MA with pricing that ranges from $1,110 to $17,921. There are also 268 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,275 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 $1,275 to $28,000 with an average monthly rent of $5,511.
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 $3,300 and Four Bedroom Apartments start at $1,150.
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

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
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
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.