7 Lily Pond Ln
LexingtonMA02420
Luxury Homes for Rent in Winchester, MA (281 Rentals) Page 4 of 6
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.
15 Orchard St
MedfordMA02155
3 Hamilton Rd
SomervilleMA02144
215-217 Boston Ave
MedfordMA02155
1 Victoria St, Unit 2
1 Victoria St
SomervilleMA02144
1 Victoria St, Unit 2
1 Victoria St
SomervilleMA02144
1 Victoria St
SomervilleMA02144
190 North St, Unit 2
190 North St
SomervilleMA02144
190 North St, Unit 2
190 North St
SomervilleMA02144
271 Ridge St
ArlingtonMA02474
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5 Harris Rd, Unit 2
5 Harris Rd
MedfordMA02155
75 Summer St, Unit 1
75 Summer St
MedfordMA02155
50 Curtis Ave, Unit 1
50 Curtis Ave
SomervilleMA02144
5 Harris Rd
MedfordMA02155
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$4,400
Plus Fees
4 Bedroom Apartments Available Jun 1, 202656 Gordon St
56 Gordon StSomerville, MA 02144
5 Harris Rd
MedfordMA02155
86 Orchard St, Unit 1
86 Orchard St
MedfordMA02155
11 Parkway Rd
MedfordMA02155
199 Broadway
ArlingtonMA02474
11 Parkway Rd
MedfordMA02155
22 James St
WoburnMA01801
17 Circle Rd
LexingtonMA02420
14 Barton St, Unit 2
14 Barton St
SomervilleMA02144
62 Woods Ave
SomervilleMA02144
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$4,750
Plus Fees
4 Bedroom Apartments Available Jun 1, 2026288 Boston Ave
288 Boston AveMedford, MA 02155
49 Ripley Rd
MedfordMA02155
195 Forest St
ArlingtonMA02474
112 College Ave, Unit U2
112 College Ave
MedfordMA02155
35 Bowdoin St, Unit 35
35 Bowdoin St
ArlingtonMA02474
19 Sunset Rd
SomervilleMA02144
24 Chetwynd Rd, Unit 1
24 Chetwynd Rd
SomervilleMA02144
65 Conwell Ave, Unit 1
65 Conwell Ave
SomervilleMA02144
14 Fairmount St
MedfordMA02155
40 Marrett Rd
LexingtonMA02421
93 Churchill Ave
ArlingtonMA02476
355 Boston Ave, Unit 1
355 Boston Ave
MedfordMA02155
355 Boston Ave, Unit 1
355 Boston Ave
MedfordMA02155
25 Chetwynd Rd, Unit 24-1
25 Chetwynd Rd
SomervilleMA02144
24 Chetwynd Rd
SomervilleMA02144
46 Sunset Rd, Unit 1
46 Sunset Rd
SomervilleMA02144
301 Alewife Brook Pky, Unit T
301 Alewife Brook Pky
SomervilleMA02144
301 Alewife Brook Pky
SomervilleMA02144
301 Alewife Brook Pky, Unit 301
301 Alewife Brook Pky
SomervilleMA02144
64 Chetwynd Rd, Unit 1
64 Chetwynd Rd
SomervilleMA02144
10 Greenleaf Ave, Unit 1
10 Greenleaf Ave
MedfordMA02155
24 Chetwynd Rd
SomervilleMA02144
217 Arlington St
MedfordMA02155
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 | $3,004 | $2,075 | $5,700 |
| Winchester 3 Bedroom Homes for Rent | $3,869 | $1,200 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $5,192 | $3,300 | $8,000 |
| Winchester 5 Bedroom Homes for Rent | $6,816 | $4,200 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $9,392 | $6,200 | $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 532 Apartments for Rent in Winchester, MA with pricing that ranges from $1,200 to $9,300. There are also 331 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,100 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 $1,100 to $40,000 with an average monthly rent of $4,642.
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 $1,200 to $20,000. Four Bedroom Single-Family rentals are also available starting from $3,300 and Four Bedroom Apartments start at $3,000.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.
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.
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.