Luxury Homes for Rent in Winchester, MA (230 Rentals) Page 3 of 5

The most luxurious Homes in Winchester with high-end amenities, features, and finishes.

$3,600

12 Month Lease Term

4 Bedroom, 2 Bath Townhome for Rent

Available Now

Cost Per Sq.Ft.

39 Manning St

MedfordMA02155

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$3,6003 Bedroom Apartments Available Now

175 Boston Ave, Unit #2

175 Boston AveSomerville, MA 02144

Pet Friendly

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$3,6003 Bedroom Apartments Available Now

65 Conwell Ave, Unit #2

65 Conwell AveSomerville, MA 02144

Smoke Free

$3,650

2 Bedroom, 2.5 Bath Townhome for Rent

Available Now

Pet Friendly

14 Schouler Ct

ArlingtonMA02476

$3,700

2 Bedroom, 2.5 Bath Townhome for Rent

Available Now

555 Main St

WoburnMA01801

$3,700

3 Bedroom, 1.5 Bath Townhome for Rent

Available Now

36 Chester Ave

MedfordMA02155

$3,750

2 Bedroom, 2 Bath Townhome for Rent

Available Now

463 Fulton St

MedfordMA02155

$3,800

1 Month Lease Term

3 Bedroom, 1.5 Bath Townhome for Rent

Available Now

Cost Per Sq.Ft.

159 Bedford Rd

WoburnMA01801

$3,800

4 Bedroom, 1.5 Bath Condo for Rent

Available Now

Cost Per Sq.Ft.

45-47 Webster St

ArlingtonMA02474

$3,800

2 Bedroom, 1 Bath Home for Rent

Available Now

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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$3,800

12 Month Lease Term

4 Bedroom, 1.5 Bath Home for Rent

Available Now

321 Washington St

ArlingtonMA02474

$3,850

3 Bedroom, 1.5 Bath Home for Rent

Available Now

Outdoors

25 Essex St

MedfordMA02155

$3,900

3 Bedroom, 1 Bath Condo for Rent

Available Now

12 Lockeland Ave

ArlingtonMA02476

$3,900

2 Bedroom, 1.5 Bath Home for Rent

Available Sep 21

Cost Per Sq.Ft.

27 Buena Vista Rd

ArlingtonMA02476

$3,900

3 Bedroom, 2 Bath Condo for Rent

Available Now

Cost Per Sq.Ft.

100 Place Ln

WoburnMA01801

$3,900

3 Bedroom, 1 Bath Condo for Rent

Available Now

34 Irvington Rd

SomervilleMA02144

$3,900

3 Bedroom, 2 Bath Townhome for Rent

Available Now

132 Grant St

LexingtonMA02420

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$3,9003 Bedroom Apartments Available Now

126 Auburn St, Unit #1

126 Auburn StMedford, MA 02155

Smoke Free

$3,950

3 Bedroom, 1 Bath Home for Rent

Available Now

154 Maple St

LexingtonMA02420

$3,950

12 Month Lease Term

4 Bedroom, 2 Bath Home for Rent

Available Now

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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$3,9954 Bedroom Apartments Available Now

138 W Adams St

138 W Adams StSomerville, MA 02144

$4,000

3 Bedroom, 1.5 Bath Home for Rent

Available Now

42 Rockland Ave

ArlingtonMA02474

$4,000

12 Month Lease Term

3 Bedroom, 1 Bath Condo for Rent

Available Now

Cost Per Sq.Ft.

112 College Ave, Unit 1##

112 College Ave

MedfordMA02155

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$4,0004 Bedroom Apartments Available Now

27 Fairfax St, Unit 1

27 Fairfax StSomerville, MA 02144

$4,000

3 Bedroom, 2 Bath Home for Rent

Available Now

Luxury

53 Dickson Ave

ArlingtonMA02474

$4,000

3 Bedroom, 1.5 Bath Rentals

Available Now

77 Brookings St, Unit 2

77 Brookings St

MedfordMA02155

$4,000

4 Bedroom, 2 Bath Rentals

Available Sep 15

Cost Per Sq.Ft.

89 Burget Ave, Unit 2

89 Burget Ave

MedfordMA02155

$4,000

4 Bedroom, 2 Bath Rentals

Available Oct 1

Cost Per Sq.Ft.

89 Burget Ave, Unit 2

89 Burget Ave

MedfordMA02155

$4,000

1 Month Lease Term

4 Bedroom, 1 Bath Townhome for Rent

Available Now

Cost Per Sq.Ft.

6 Johnson St

WoburnMA01801

$4,000

3 Bedroom, 2 Bath Townhome for Rent

Available Oct 1

1087 Massachusetts Ave

ArlingtonMA02476

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$4,0503 Bedroom Apartments Available Jun 1, 2027

95 Winthrop St

95 Winthrop StMedford, MA 02155

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$4,1004 Bedroom Apartments Available Now

27 Fairfax St, Unit 2

27 Fairfax StSomerville, MA 02144

$4,100

3 Bedroom, 2 Bath Condo for Rent

Available Now

2 Holton St

MedfordMA02155

$4,200

3 Bedroom, 2 Bath Rentals

Available Oct 1

Cost Per Sq.Ft.

89 Burget Ave, Unit 2

89 Burget Ave

MedfordMA02155

$4,200

3 Bedroom, 2 Bath Rentals

Available Now

Cost Per Sq.Ft.

89 Burget Ave, Unit 2

89 Burget Ave

MedfordMA02155

$4,200

12 Month Lease Term

3 Bedroom, 2.5 Bath Townhome for Rent

Available Now

Cost Per Sq.Ft.

2 Glenbrook Ln

ArlingtonMA02474

$4,200

12 Month Lease Term

3 Bedroom, 2 Bath Townhome for Rent

Available Now

Cost Per Sq.Ft.

3 Hamilton Rd

SomervilleMA02144

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$4,2003 Bedroom Apartments Available Jun 1, 2027

2 High St

2 High StSomerville, MA 02144

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$4,2003 Bedroom Apartments Available Jun 1, 2027

144 W Adams St

144 W Adams StSomerville, MA 02144

$4,200

3 Bedroom, 2.5 Bath Townhome for Rent

Available Oct 1

801 Manor Ter

LexingtonMA02420

$4,300

3 Bedroom, 2 Bath Townhome for Rent

Available Now

122 Massachusetts Ave

LexingtonMA02420

$4,300

12 Month Lease Term

2 Bedroom, 1 Bath Home for Rent

Available Oct 1

16 Longfellow Rd

ArlingtonMA02476

$4,300

3 Bedroom, 2 Bath Townhome for Rent

Available Nov 1

2-4 Holton St

MedfordMA02155

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$4,3505 Bedroom Apartments Available Now

249 Boston Ave, Unit 3

249 Boston AveMedford, MA 02155

Furnished

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$4,3503 Bedroom Apartments Available Jun 1, 2027

69 Hillsdale Rd, Unit 1

69 Hillsdale RdMedford, MA 02155

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$4,4004 Bedroom Apartments Available Jun 1, 2027

100 W Adams St, Unit 2

100 W Adams StSomerville, MA 02144

$4,400

12 Month Lease Term

4 Bedroom, 1 Bath Townhome for Rent

Available Now

Luxury

4 Senator Rd

WoburnMA01801

$4,500

4 Bedroom, 2 Bath Rentals

Available Now

Cost Per Sq.Ft.

89 Burget Ave, Unit 2

89 Burget Ave

MedfordMA02155

$4,500

3 Bedroom, 2.5 Bath Home for Rent

Available Now

69 Orchard St

MedfordMA02155

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$4,5003 Bedroom Apartments Available Jun 1, 2027

185 Powder House Blvd, Unit 1

185 Powder House BlvdSomerville, MA 02144

Showing Results 101-150, Page 3 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	$2,996	$1,000	$4,750
Winchester 3 Bedroom Homes for Rent	$3,912	$2,800	$6,500
Winchester 4 Bedroom Homes for Rent	$5,150	$3,450	$8,750
Winchester 5 Bedroom Homes for Rent	$8,353	$4,750	$10,000+
Winchester 6 Bedroom Homes for Rent	$9,609	$6,495	$10,000+

Browse Top Homes for Rent in Winchester

Frequently Asked Questions about Winchester

What type of rentals are currently available in Winchester?

There are currently 445 Apartments for Rent in Winchester, MA with pricing that ranges from $825 to $18,885. There are also 283 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $800 to $18,000.

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 $800 to $18,000 with an average monthly rent of $4,028.

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 $6,718, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $6,500. Four Bedroom Single-Family rentals are also available starting from $3,450 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.