
Luxury Homes for Rent in Winchester, MA (211 Rentals) Page 4 of 5
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.


15 Governor Rd

14 Sturtevant Ter

9 Peacock Farm Rd

14 Kings Ct

14 Kings Ct

318 Mystic St

34 Hume Ave, Unit 2

33 Hamilton St

34 Park St

34 Linden St

36 Whittier Rd

10 Greenleaf Ave, Unit 1

217 Arlington St

479 Fulton St

61 Wollaston Ave, Unit 61 Wollaston Ave - 2

30 Peacock Farm Rd

36 Gould St

260 Boston Ave, Unit 2

61 Warren St

11 Raymond Ave

33 Raymond Ave, Unit 2

33 Raymond Ave, Unit 3

18 Curtis Ave, Unit 1

15 Curtis Ave, Unit 1

21 Franklin St

14 Curtis Ave, Unit 2

455 Summer St

27 Emery St, Unit 1

6 Lily Pond Ln

21 Sunset Rd, Unit 2

2 Michael St

52 Hillsdale Rd

15 Bartlett Ave, Unit TH

120 Jerome St, Unit 1

3 Day Cir

18 Winchester Dr

82 Arlmont St

322 Lowell St

559 Winthrop St

15 University Rd

140 Jerome St

230 Fulton St

15 Campbell Rd

14 Sturtevant Terrace, Unit 1

15 Campbell Rd

15 Curtis Ave, Unit 2

16 Curtis Ave, Unit 2

11 Garrison Rd

120 Jerome 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 | $3,079 | $2,400 | $4,250 |
| Winchester 3 Bedroom Homes for Rent | $4,136 | $3,000 | $6,800 |
| Winchester 4 Bedroom Homes for Rent | $5,612 | $3,475 | $10,000+ |
| Winchester 5 Bedroom Homes for Rent | $9,199 | $5,000 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,941 | $6,495 | $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 399 Apartments for Rent in Winchester, MA with pricing that ranges from $1,650 to $20,951. There are also 263 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $985 to $20,000.
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 $985 to $20,000 with an average monthly rent of $5,008.
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 $5,994, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 to $6,800. Four Bedroom Single-Family rentals are also available starting from $3,475 and Four Bedroom Apartments start at $3,300.
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

What It Really Costs to Live in Boston: A Local Renter's Guide
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.

Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com expert for Boston!

Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com expert for Boston, and I’m excited to help you find your next home!

Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Written by: Amelia Ramstead
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

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.

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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.