4 Quigley Ct
WinchesterMA01890
Luxury Homes for Rent in Winchester, MA (231 Rentals)
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.
400 Cross St
WinchesterMA01890
7 Conant Rd
WinchesterMA01890
11 Elmwood Ave
WinchesterMA01890
20 Lebanon St, Unit 22
20 Lebanon St
WinchesterMA01890
8 Albamont Rd
WinchesterMA01890
12 James St
WinchesterMA01890
113 Cambridge St
WinchesterMA01890
2 Rangeley Rd
WinchesterMA01890
271 Washington St
WinchesterMA01890
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29 Wainwright Rd
WinchesterMA01890
23 Olde Village Dr
WinchesterMA01890
100 Ledgewood Dr, Unit 515
100 Ledgewood Dr
StonehamMA02180
4 Colonial Village Dr
ArlingtonMA02474
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
47 Mystic St, Unit 5A
47 Mystic St
ArlingtonMA02474
10 Pine St
ArlingtonMA02474
1 Old Colony Ln
ArlingtonMA02476
200 Ledgewood Dr
StonehamMA02180
385 Massachusetts Ave
ArlingtonMA02474
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385 Massachusetts Ave
ArlingtonMA02474
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$2,650
Plus Fees
1 Bedroom Apartments Available Feb 2385 Massachusetts Ave
385 Massachusetts AveArlington, MA 02474
385 Massachusetts Ave
ArlingtonMA02474
385 Massachusetts Ave
ArlingtonMA02474
65 Woods Ave
SomervilleMA02144
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
269 Cambridge Rd
WoburnMA01801
269 Cambridge Rd
WoburnMA01801
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$2,700
Plus Fees
1 Bedroom Apartments Available Now1 Sorelle Pl
1 Sorelle PlBurlington, MA 01803
34 Hamilton Rd
ArlingtonMA02474
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22 Norcross St
ArlingtonMA02474
385 Massachusetts Ave
ArlingtonMA02474
385 Massachusetts Ave
ArlingtonMA02474
39 Franklin St
WoburnMA01801
5 Curve St
LexingtonMA02420
67 Greenleaf Ave
MedfordMA02155
5 Curve St
LexingtonMA02420
48 Moulton Rd
ArlingtonMA02476
36 Union St
WoburnMA01801
94 North St
SomervilleMA02144
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92 North St
SomervilleMA02144
67 Fairfax St, Unit 1
67 Fairfax St
SomervilleMA02144
53 Fairfax St, Unit 1
53 Fairfax St
SomervilleMA02144
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$2,900
Plus Fees
2 Bedroom Apartments Available Now69 Raymond Ave
69 Raymond AveSomerville, MA 02144
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$2,900
Plus Fees
2 Bedroom Apartments Available Now82 North St
82 North StMedford, MA 02155
723 Fellsway
MedfordMA02155
12 Gould St
StonehamMA02180
139 Hillsdale Rd, Unit 2
139 Hillsdale Rd
SomervilleMA02144
72 Marshall St
MedfordMA02155
94 North St
SomervilleMA02144
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Winchester, MA Local Guide
Downtown Winchester, Massachusetts by Moonshine4711 is licensed under CC BY-SA 3.0
How much does it cost to rent a home in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $2,878 | $2,075 | $5,580 |
| Winchester 3 Bedroom Homes for Rent | $3,605 | $1,475 | $5,500 |
| Winchester 4 Bedroom Homes for Rent | $5,102 | $3,200 | $8,500 |
| Winchester 5 Bedroom Homes for Rent | $6,723 | $2,800 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,195 | $6,200 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $7,700 | $7,700 | $7,700 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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Winchester, MA Local Guide
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Boston Neighborhood Guide: Living Near UMass, MGH, and State Street
Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.
Read Article
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash 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.
Read ArticleTop Neighborhoods Near Boston Colleges and Universities
Learn About the Best Neighborhoods to Rent Near College Campuses in Boston, MA | Find Boston Off-Campus Student Housing at ApartmentHomeLiving.com
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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Explore Winchester, MA Rentals by Map
See the most popular apartments and homes in Winchester, MA
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 490 Apartments for Rent in Winchester, MA with pricing that ranges from $950 to $9,300. There are also 296 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 $4,770.
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 $2,699 to $6,900, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,475 to $5,500. Four Bedroom Single-Family rentals are also available starting from $3,200 and Four Bedroom Apartments start at $950.
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
Written by: Amelia Ramstead
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.
A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!
Explore Like a Local: The Insider's Guide to Boston
Written by: Amelia Ramstead
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
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
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.
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.