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$4,400
Plus Fees
4 Bedroom Apartments Available Jun 1, 202656 Gordon St
56 Gordon StSomerville, MA 02144
Luxury Homes for Rent in Winchester, MA (262 Rentals) Page 4 of 6
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.
28 Theresa Ave
LexingtonMA02420
50 Curtis Ave, Unit 1
50 Curtis Ave
SomervilleMA02144
5 Harris Rd
MedfordMA02155
185 Mystic St
ArlingtonMA02474
207 Boston Ave, Unit A
207 Boston Ave
MedfordMA02155
17 Circle Rd
LexingtonMA02420
14 Barton St, Unit 2
14 Barton St
SomervilleMA02144
49 Ripley Rd
MedfordMA02155
49 Ripley Rd
MedfordMA02155
49 Ripley Rd
MedfordMA02155
195 Forest St
ArlingtonMA02474
17 Circle Rd
LexingtonMA02420
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$4,600
Plus Fees
4 Bedroom Apartments Available Jun 1, 2026288 Boston Ave
288 Boston AveMedford, MA 02155
62 Woods Ave
SomervilleMA02144
2 Osgood St, Unit 1
2 Osgood St
SomervilleMA02143
112 College Ave, Unit U2
112 College Ave
MedfordMA02155
112 College Ave, Unit U2
112 College Ave
MedfordMA02155
35 Bowdoin St, Unit 35
35 Bowdoin St
ArlingtonMA02474
19 Sunset Rd
SomervilleMA02144
65 Conwell Ave, Unit Unit 1
65 Conwell Ave
SomervilleMA02144
14 Fairmount St
MedfordMA02155
77 North St
SomervilleMA02144
93 Churchill Ave
ArlingtonMA02476
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40 Brattle St
ArlingtonMA02476
33 Ashcroft Rd
MedfordMA02155
16 Chetwynd Rd
SomervilleMA02144
40 Brattle St
ArlingtonMA02476
46 Sunset Rd, Unit 1
46 Sunset Rd
SomervilleMA02144
355 Boston Ave, Unit 1
355 Boston Ave
MedfordMA02155
301 Alewife Brook Pky
SomervilleMA02144
301 Alewife Brook Pky, Unit 301
301 Alewife Brook Pky
SomervilleMA02144
10 Greenleaf Ave, Unit 1
10 Greenleaf Ave
MedfordMA02155
64 Chetwynd Rd, Unit 1
64 Chetwynd Rd
SomervilleMA02144
476 Fulton St, Unit Unit 478
476 Fulton St
MedfordMA02155
478 Fulton St
MedfordMA02155
101 Richmond Rd
BelmontMA02478
217 Arlington St
MedfordMA02155
479 Fulton St
MedfordMA02155
480 Fulton St, Unit 478
480 Fulton St
MedfordMA02155
42 Sunset Rd, Unit #2
42 Sunset Rd
SomervilleMA02144
70 Curtis St
SomervilleMA02144
76 Orchard St
MedfordMA02155
159 Allston St
MedfordMA02155
135 Maple St
LexingtonMA02420
90 Monument St
MedfordMA02155
76 Curtis St, Unit 1
76 Curtis St
SomervilleMA02144
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$5,600
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4 Bedroom Apartments Available Jun 1, 202650 Upland Rd
50 Upland RdSomerville, MA 02144
31 Raymond Ave, Unit 3
31 Raymond Ave
SomervilleMA02144
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 | $2,908 | $2,175 | $5,700 |
| Winchester 3 Bedroom Homes for Rent | $3,678 | $2,800 | $5,500 |
| Winchester 4 Bedroom Homes for Rent | $5,061 | $3,300 | $8,000 |
| Winchester 5 Bedroom Homes for Rent | $6,508 | $2,800 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,897 | $5,000 | $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.
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 488 Apartments for Rent in Winchester, MA with pricing that ranges from $1,000 to $9,300. There are also 310 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,500 to $40,000.
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 $1,500 to $40,000 with an average monthly rent of $4,852.
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 $2,500 to $6,900, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $5,500. Four Bedroom Single-Family rentals are also available starting from $3,300 and Four Bedroom Apartments start at $1,000.
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
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.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.