Luxury Apartments for Rent in Winchester, MA (327 Rentals) Page 3 of 7

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

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65 Sterling St, Unit 1
$3,300
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300
Total Monthly Price
$3,300
3 Bedroom Apartment Available Now

65 Sterling St, Unit 1

65 Sterling StSomerville, MA 02144
Affordability
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258 Boston Ave, Unit 3
$3,300
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300
Total Monthly Price
$3,300
3 Bedroom Apartment Available Now

258 Boston Ave, Unit 3

258 Boston AveMedford, MA 02155
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67 Sterling St, Unit 67
$3,300
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300
Total Monthly Price
$3,300
3 Bedroom Apartment Available Now

67 Sterling St, Unit 67

67 Sterling StSomerville, MA 02144
Affordability
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14 Holton St, Unit 1
$3,300
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300
Total Monthly Price
$3,300
3 Bedroom Apartment Available Now

14 Holton St, Unit 1

14 Holton StMedford, MA 02155
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12 Quincy St
$3,400
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400
Total Monthly Price
$3,400
3 Bedroom Apartment Available Now

12 Quincy St

12 Quincy StMedford, MA 02155
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7 Patrick St, Unit 2
$3,400
Total Monthly Price11 Month Lease Term

Total Monthly Price

Base Rent
$3,400
Total Monthly Price
$3,400
3 Bedroom Apartment Available Now

7 Patrick St, Unit 2

7 Patrick StArlington, MA 02474
  • Smoke Free
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104 W Quincy St, Unit 1
$3,400
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400
Total Monthly Price
$3,400
3 Bedroom Apartment Available Now

104 W Quincy St, Unit 1

104 W Quincy StSomerville, MA 02144
Affordability
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49 Conwell Ave, Unit 2
$3,400
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400
Total Monthly Price
$3,400
3 Bedroom Apartment Available Now

49 Conwell Ave, Unit 2

49 Conwell AveSomerville, MA 02144
Affordability
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59 Quincy St, Unit 1
$3,450
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,450
Total Monthly Price
$3,450
3 Bedroom Apartment Available Now

59 Quincy St, Unit 1

59 Quincy StMedford, MA 02155
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59 Quincy St, Unit 1
$3,450
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,450
Total Monthly Price
$3,450
3 Bedroom Apartment Available Now

59 Quincy St, Unit 1

59 Quincy StMedford, MA 02155
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Arlington 360
$3,495 - $6,953
Total Monthly Price

Total Monthly Price

Base Rent
$3,495 - $6,953
Total Monthly Price
$3,495 - $6,953
Studio to 3 Bedroom Apartments Available Now

Arlington 360

4105 Symmes CirArlington, MA 02474
Pet Friendly
  • Verified
  • Customer Reviewed
  • Utilities Included
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167 Sharon St
$3,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500
Total Monthly Price
$3,500
4 Bedroom Apartment Available Now

167 Sharon St

167 Sharon StMedford, MA 02155
Cost Per Sq.Ft.
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65 Conwell Ave
$3,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600
Total Monthly Price
$3,600
3 Bedroom Apartment Available Now

65 Conwell Ave

65 Conwell AveSomerville, MA 02144
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49 Conwell Ave, Unit 2
$3,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600
Total Monthly Price
$3,600
3 Bedroom Apartment Available Jun 1, 2026

49 Conwell Ave, Unit 2

49 Conwell AveSomerville, MA 02144
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49 Conwell Ave, Unit 2
$3,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600
Total Monthly Price
$3,600
3 Bedroom Apartment Available Jun 1, 2026

49 Conwell Ave, Unit 2

49 Conwell AveSomerville, MA 02144
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49 Conwell Ave, Unit 2
$3,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600
Total Monthly Price
$3,600
3 Bedroom Apartment Available Jun 1, 2026

49 Conwell Ave, Unit 2

49 Conwell AveSomerville, MA 02144
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112 College Ave
$3,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600
Total Monthly Price
$3,600
3 Bedroom Apartment Available Now

112 College Ave

112 College AveMedford, MA 02155
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68 North St
$3,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600
Total Monthly Price
$3,600
3 Bedroom Apartment Available Now

68 North St

68 North StSomerville, MA 02144
  • Smoke Free
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94 North St, Unit 1
$3,695
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,695
Total Monthly Price
$3,695
3 Bedroom Apartment Available Now

94 North St, Unit 1

94 North StSomerville, MA 02144
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248 Powder House Blvd, Unit B
$3,700
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700
Total Monthly Price
$3,700
4 Bedroom Apartment Available Jun 1, 2026

248 Powder House Blvd, Unit B

248 Powder House BlvdSomerville, MA 02144
Cost Per Sq.Ft.
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258 Boston Ave, Unit 2
$3,700
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700
Total Monthly Price
$3,700
3 Bedroom Apartment Available Jun 1, 2026

258 Boston Ave, Unit 2

258 Boston AveMedford, MA 02155
Cost Per Sq.Ft.
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The Legacy at Arlington Center
$3,700 - $4,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700 - $4,100
Total Monthly Price
$3,700 - $4,100
2 Bedroom Apartments Available Now

The Legacy at Arlington Center

438 Massachusetts AveArlington, MA 02474
Outdoors
  • Verified
  • Utilities Included
  • Matterport 3D Tour
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94 North St, Unit 1
$3,795
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,795
Total Monthly Price
$3,795
3 Bedroom Apartment Available Nov 1

94 North St, Unit 1

94 North StSomerville, MA 02144
Cost Per Sq.Ft.
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132 George St, Unit 1
$3,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800
Total Monthly Price
$3,800
3 Bedroom Apartment Available Jun 1, 2026

132 George St, Unit 1

132 George StMedford, MA 02155
Cost Per Sq.Ft.
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132 George St, Unit 1
$3,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800
Total Monthly Price
$3,800
3 Bedroom Apartment Available Jun 1, 2026

132 George St, Unit 1

132 George StMedford, MA 02155
Cost Per Sq.Ft.
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132 George St, Unit 1
$3,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800
Total Monthly Price
$3,800
3 Bedroom Apartment Available Jun 1, 2026

132 George St, Unit 1

132 George StMedford, MA 02155
Cost Per Sq.Ft.
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48 Raymond Ave, Unit 3
$3,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800
Total Monthly Price
$3,800
3 Bedroom Apartment Available Jun 1, 2026

48 Raymond Ave, Unit 3

48 Raymond AveSomerville, MA 02144
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79 Lyman Ave
$3,850
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,850
Total Monthly Price
$3,850
3 Bedroom Apartment Available Jun 1, 2026

79 Lyman Ave

79 Lyman AveMedford, MA 02155
Cost Per Sq.Ft.
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89 Hillsdale Rd, Unit 1
$3,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900
Total Monthly Price
$3,900
3 Bedroom Apartment Available Jun 1, 2026

89 Hillsdale Rd, Unit 1

89 Hillsdale RdMedford, MA 02155
Cost Per Sq.Ft.
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185 Powder House Blvd, Unit 1
$3,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900
Total Monthly Price
$3,900
3 Bedroom Apartment Available Jun 1, 2026

185 Powder House Blvd, Unit 1

185 Powder House BlvdSomerville, MA 02144
Cost Per Sq.Ft.
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38 George St, Unit 1
$3,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900
Total Monthly Price
$3,900
3 Bedroom Apartment Available Jun 1, 2026

38 George St, Unit 1

38 George StMedford, MA 02155
Cost Per Sq.Ft.
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59 Quincy St, Unit NA
$3,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900
Total Monthly Price
$3,900
3 Bedroom Apartment Available Now

59 Quincy St, Unit NA

59 Quincy StMedford, MA 02155
Furnished
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56 Gordon St, Unit 1
$3,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900
Total Monthly Price
$3,900
4 Bedroom Apartment Available Now

56 Gordon St, Unit 1

56 Gordon StSomerville, MA 02144
Showing Results 101-150, Page 3 of 7

Getting Around Winchester, MA

Walk Score®

71 / 100

Very Walkable

Most errands can be accomplished on foot

Bike Score®

67 / 100

Bikeable

Some bike infrastructure

Transit Score®

1 / 100

Minimal Transit

It may be possible to get on a bus

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about Winchester

How much are Studio apartments in Winchester?

There are currently 104 Studio Apartments in Winchester with rent ranges from $1,200 to $2,829 with an average price of $2,166.

What is the current price range for One Bedroom Winchester Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Winchester ranges from $1,395 to $4,195 with an average monthly rent of $2,669.

What does renting a Two Bedroom Apartment in Winchester cost?

The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $2,195 to $5,999. Today's average rental price for Two Bedrooms here is $3,230.

How expensive are Winchester Three Bedroom Apartments?

There are currently 153 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,500 to $6,900 - averaging $3,682 for the location.

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.

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