
Luxury Homes for Rent in Winchester, MA (241 Rentals) Page 4 of 5
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.


14 Hamilton Rd, Unit 14

27 Fairfax St, Unit 2

299 Alewife Brook Pkwy, Unit 2

2 Osgood St, Unit 1

33 Raymond Ave

12 Headland Way

33 Raymond Ave, Unit 3

33 Raymond Ave, Unit 2

72 Cambridge Rd

12 Barton St

49 Oakland St, Unit 2

171 Forest St, Unit SF

83 Orient Ave

190 North St

190 North St, Unit 2

39 Newland Rd

14 Fairmount St

6 Highland Ave

34 Park St

355 Boston Ave, Unit 1

301 Alewife Brook Pky

301 Alewife Brook Pky

34 Linden St

10 Greenleaf Ave, Unit 1

14 Kings Ct

14 Kings Ct

10 Pinkham Rd, Unit 2##

217 Arlington St

37 Fountain Rd

61 Wollaston Ave, Unit 61 Wollaston Ave - 2

15 Taylor St, Unit A

31 Raymond Ave

195 Forest St

30 Peacock Farm Rd

133 High Haith Rd

36 Gould St

260 Boston Ave, Unit 2

76 Curtis St, Unit 1

6 Burlwood Ln

133 Winthrop St

19 Sunset Rd

15 Trotting Horse Dr

2 Summer Hill Cir

186 Salem St

60 Powder House Rd

157 Boston Ave

17 Tesla Ave

14 Curtis Ave, Unit 2

101 Richmond 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 | $3,079 | $2,100 | $4,500 |
| Winchester 3 Bedroom Homes for Rent | $4,117 | $2,500 | $8,000 |
| Winchester 4 Bedroom Homes for Rent | $5,153 | $1,350 | $10,000+ |
| Winchester 5 Bedroom Homes for Rent | $8,904 | $4,325 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $10,901 | $6,200 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $8,400 | $5,300 | $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 409 Apartments for Rent in Winchester, MA with pricing that ranges from $950 to $10,993. There are also 289 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,050 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 $1,050 to $28,000 with an average monthly rent of $5,582.
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 $950 to $6,297, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $8,000. Four Bedroom Single-Family rentals are also available starting from $1,350 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

The 10 Best Affordable Neighborhoods in Boston, MA
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A Local Experts Guide to the Top Boston Neighborhoods for College Renters
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Explore Like a Local: The Insider's Guide to Boston
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Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.

Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
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Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.