16 Kilby St
WoburnMA01801
Luxury Homes for Rent in Winchester, MA (241 Rentals) Page 2 of 5
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.
16 Kilby St
WoburnMA01801
1 Main St
WoburnMA01801
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$2,9502 Bedroom Apartments Available Now
10 Fessenden Rd, Unit 2
10 Fessenden RdArlington, MA 02476
1 Watermill Pl, Unit 112
1 Watermill Pl
ArlingtonMA02476
114 Spy Pond Pkwy, Unit B
114 Spy Pond Pkwy
ArlingtonMA02474
32 Gourley Rd
MedfordMA02155
29 Harvard Ave, Unit 33
29 Harvard Ave
MedfordMA02155
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$3,0002 Bedroom Apartments Available Sep 1
79 Capen St, Unit 2
79 Capen StMedford, MA 02155
56 Gordon St
SomervilleMA02144
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.
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$3,0002 Bedroom Apartments Available Jul 1
10 Davis St, Unit 2
10 Davis StWoburn, MA 01801
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$3,0002 Bedroom Apartments Available Now
92 Sylvia St
92 Sylvia StArlington, MA 02474
65 Woods Ave
SomervilleMA02144
1 Victoria St
SomervilleMA02144
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$3,1003 Bedroom Apartments Available Now
92 Sylvia St, Unit 2
92 Sylvia StArlington, MA 02476
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$3,1002 Bedroom Apartments Available Now
385 Massachusetts Ave, Unit 32
385 Massachusetts AveArlington, MA 02474
380 Place Ln
WoburnMA01801
260 Boston Ave, Unit 1
260 Boston Ave
MedfordMA02155
245 Boston Ave, Unit 3
245 Boston Ave
MedfordMA02155
72 Harlow St, Unit 72
72 Harlow St
ArlingtonMA02474
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.
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$3,3503 Bedroom Apartments Available Sep 1
32 Curtis Ave, Unit 2
32 Curtis AveSomerville, MA 02144
258 Boston Ave
MedfordMA02155
258 Boston Ave, Unit 3
258 Boston Ave
MedfordMA02155
95 Capen St, Unit Apt 1
95 Capen St
MedfordMA02155
1 Victoria St
SomervilleMA02144
33 Harvard St
ArlingtonMA02476
282 Place Ln
WoburnMA01801
14 Kilby St
WoburnMA01801
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$3,4004 Bedroom Apartments Available Sep 1
14 Allen St, Unit 2-3
14 Allen StArlington, MA 02474
227 Boston Ave
MedfordMA02155
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
207 Boston Ave
MedfordMA02155
31 Lyman Ave
MedfordMA02155
7 Greenleaf Ave, Unit 1
7 Greenleaf Ave
MedfordMA02155
88 North St
SomervilleMA02144
62 Newport St, Unit 2
62 Newport St
ArlingtonMA02476
52 Mt Vernon St, Unit 52
52 Mt Vernon St
ArlingtonMA02476
52 Mt Vernon St
ArlingtonMA02476
31 Lyman Ave, Unit 1
31 Lyman Ave
MedfordMA02155
4 Park St, Unit 1
4 Park St
ArlingtonMA02474
124 Forest St, Unit 1
124 Forest St
MedfordMA02155
4 Park St
ArlingtonMA02474
32 Irvington Rd
SomervilleMA02144
35 Stoughton St
MedfordMA02155
219 Forest St
MedfordMA02155
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$3,6004 Bedroom Apartments Available Now
288 Boston Ave, Unit 3
288 Boston AveMedford, MA 02155
5 Harris Rd
MedfordMA02155
62 Newport St, Unit 2
62 Newport St
ArlingtonMA02476
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$3,6503 Bedroom Apartments Available Now
38 George St, Unit 1
38 George StMedford, MA 02155
3 Melo Rd
WoburnMA01801
15 Taylor St, Unit 1
15 Taylor St
MedfordMA02155
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+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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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
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
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.