29 Harvard Ave, Unit 33
29 Harvard Ave
MedfordMA02155
Luxury Homes for Rent in Winchester, MA (211 Rentals) Page 2 of 5
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.
2500 Mystic Valley Pkwy
MedfordMA02155
1 Watermill Pl
ArlingtonMA02476
close
View Me
$3,0003 Bedroom Apartments Available Sep 1
34 Hume Ave, Unit 1
34 Hume AveMedford, MA 02155
20 Bryant St
WoburnMA01801
close
View Me
$3,0002 Bedroom Apartments Available Now
10 Davis St, Unit 2
10 Davis StWoburn, MA 01801
close
View Me
$3,0002 Bedroom Apartments Available Sep 1
79 Capen St, Unit 2
79 Capen StMedford, MA 02155
close
View Me
$3,1003 Bedroom Apartments Available Now
92 Sylvia St, Unit 2
92 Sylvia StArlington, MA 02476
47 Curtis Ave, Unit 3
47 Curtis Ave
SomervilleMA02144
39-41 Forest St
ArlingtonMA02476
Explore Like a Local: The Insider's Guide to Boston
Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.
21 Harold St, Unit 2
21 Harold St
MedfordMA02155
21 Royall St, Unit 3B1B on 2nd FL
21 Royall St
MedfordMA02155
132 Emerson Gardens Rd
LexingtonMA02420
380 Place Ln
WoburnMA01801
52 Mt Vernon St, Unit 52
52 Mt Vernon St
ArlingtonMA02476
56 Emerson Gardens Rd
LexingtonMA02420
282 Place Ln
WoburnMA01801
2500 Mystic Valley Pky, Unit 805
2500 Mystic Valley Pky
MedfordMA02155
52 Clark St, Unit 1
52 Clark St
MedfordMA02155
close
View Me
$3,2002 Bedroom Apartments Available Aug 15
2500 Mystic Valley Pkwy, Unit #805
2500 Mystic Valley PkwyMedford, MA 02155
Boston's Best Affordable Neighborhoods
Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead
close
View Me
$3,2002 Bedroom Apartments Available Sep 1
96 Capen St, Unit #2
96 Capen StMedford, MA 02155
245 Boston Ave, Unit 3
245 Boston Ave
MedfordMA02155
close
View Me
$3,3003 Bedroom Apartments Available Now
72 Bower St, Unit #1
72 Bower StMedford, MA 02155
47 Curtis Ave, Unit 1
47 Curtis Ave
SomervilleMA02144
333 Alewife Brook Pky, Unit 2
333 Alewife Brook Pky
SomervilleMA02144
61 Dudley St
ArlingtonMA02476
35 Bowker St
LexingtonMA02421
15 Quincy St
MedfordMA02155
close
View Me
$3,3003 Bedroom Apartments Available Sep 1
333 Alewife Brook Pkwy, Unit 2
333 Alewife Brook PkwySomerville, MA 02144
31 Lyman Ave, Unit 1
31 Lyman Ave
MedfordMA02155
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
31 Lyman Ave
MedfordMA02155
72 Harlow St, Unit 72
72 Harlow St
ArlingtonMA02474
555 Main St
WoburnMA01801
close
View Me
$3,350Studio Apartments Available Now
72 Harlow St, Unit 1
72 Harlow StArlington, MA 02474
258 Boston Ave
MedfordMA02155
close
View Me
$3,3903 Bedroom Apartments Available Sep 1
127 Hillsdale Rd
127 Hillsdale RdSomerville, MA 02144
close
View Me
$3,4003 Bedroom Apartments Available Sep 1
186 Powder House Blvd, Unit 4
186 Powder House BlvdSomerville, MA 02144
993 Massachusetts Ave
LexingtonMA02420
991 Massachusetts Ave
LexingtonMA02420
close
View Me
$3,4004 Bedroom Apartments Available Sep 1
14 Allen St, Unit 2-3
14 Allen StArlington, MA 02474
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
42 Belknap St
SomervilleMA02144
533-535-535 Main St
StonehamMA02180
12 Stevens St
MedfordMA02155
36 Carroll Rd
WoburnMA01801
12 Anna Rd
WoburnMA01801
28 Scituate St
ArlingtonMA02476
4 Park St, Unit 1
4 Park St
ArlingtonMA02474
4 Park St
ArlingtonMA02474
106 Boston Ave
MedfordMA02155
165 Cambridge Rd
WoburnMA01801
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
Showing Results 51-100, Page 2 of 5
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+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Homes for Rent in Winchester
Explore Winchester
Let everyone know!
Do you know the Winchester area?
If you’re an expert on all things Winchester, tell us what you love (and don't) by rating it and writing a review.
Write a Review
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.