Luxury Apartments for Rent in Winchester, MA (331 Rentals) Page 5 of 7

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

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104 W Adams St, Unit 2
$5,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000
Total Monthly Price
$5,000
4 Bedroom Apartment Available Jun 1, 2026

104 W Adams St, Unit 2

104 W Adams StSomerville, MA 02144
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62 Woods Ave, Unit 2
$5,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500
Total Monthly Price
$5,500
5 Bedroom Apartment Available Jun 1, 2026

62 Woods Ave, Unit 2

62 Woods AveSomerville, MA 02144
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132 George St, Unit 2
$5,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500
Total Monthly Price
$5,500
5 Bedroom Apartment Available Now

132 George St, Unit 2

132 George StMedford, MA 02155
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80 Broadway
Rent Specials
$5,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500
Total Monthly Price
$5,500
2 Bedroom Apartments Available Now

80 Broadway

80 BroadwayArlington, MA 02474
Furnished
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  • Utilities Included
  • Matterport 3D Tour
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141 George St, Unit 1
$5,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500
Total Monthly Price
$5,500
5 Bedroom Apartment Available Jun 1, 2026

141 George St, Unit 1

141 George StMedford, MA 02155
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24 Chetwynd Rd, Unit 1
$5,550
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,550
Total Monthly Price
$5,550
4 Bedroom Apartment Available Jun 1, 2026

24 Chetwynd Rd, Unit 1

24 Chetwynd RdSomerville, MA 02144
Cost Per Sq.Ft.
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19 Sunset Rd, Unit 1
$5,600
Total Monthly Price24 Month Lease Term

Total Monthly Price

Base Rent
$5,600
Total Monthly Price
$5,600
4 Bedroom Apartment Available Jun 1, 2026

19 Sunset Rd, Unit 1

19 Sunset RdSomerville, MA 02144
Cost Per Sq.Ft.
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86 Quincy St, Unit 2
$5,650
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,650
Total Monthly Price
$5,650
4 Bedroom Apartment Available Jun 1, 2026

86 Quincy St, Unit 2

86 Quincy StMedford, MA 02155
Cost Per Sq.Ft.
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76 Curtis St, Unit 1
$5,729
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,729
Total Monthly Price
$5,729
5 Bedroom Apartment Available Now

76 Curtis St, Unit 1

76 Curtis StSomerville, MA 02144
Cost Per Sq.Ft.
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3 Hamilton Rd, Unit #2
$5,945
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,945
Total Monthly Price
$5,945
6 Bedroom Apartment Available Now

3 Hamilton Rd, Unit #2

3 Hamilton RdSomerville, MA 02144
Cost Per Sq.Ft.
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5 Hamilton Rd, Unit 1
$5,945
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,945
Total Monthly Price
$5,945
6 Bedroom Apartment Available Now

5 Hamilton Rd, Unit 1

5 Hamilton RdSomerville, MA 02144
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3 Hamilton Rd, Unit #2
$6,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200
Total Monthly Price
$6,200
6 Bedroom Apartment Available Now

3 Hamilton Rd, Unit #2

3 Hamilton RdSomerville, MA 02144
Cost Per Sq.Ft.
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14 Fairmount St, Unit 14.5
$6,250
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,250
Total Monthly Price
$6,250
5 Bedroom Apartment Available Now

14 Fairmount St, Unit 14.5

14 Fairmount StMedford, MA 02155
Cost Per Sq.Ft.
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14 Fairmount St, Unit 14.5
$6,250
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,250
Total Monthly Price
$6,250
5 Bedroom Apartment Available Now

14 Fairmount St, Unit 14.5

14 Fairmount StMedford, MA 02155
Cost Per Sq.Ft.
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14 Fairmount St, Unit 14.5
$6,250
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,250
Total Monthly Price
$6,250
5 Bedroom Apartment Available Now

14 Fairmount St, Unit 14.5

14 Fairmount StMedford, MA 02155
Cost Per Sq.Ft.
  • Smoke Free
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123 Winthrop St, Unit 1
$6,250
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,250
Total Monthly Price
$6,250
5 Bedroom Apartment Available Jun 1, 2026

123 Winthrop St, Unit 1

123 Winthrop StMedford, MA 02155
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80 Curtis St, Unit 1
$6,300
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,300
Total Monthly Price
$6,300
6 Bedroom Apartment Available Now

80 Curtis St, Unit 1

80 Curtis StSomerville, MA 02144
Cost Per Sq.Ft.
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24 Chetwynd Rd
$6,375
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,375
Total Monthly Price
$6,375
5 Bedroom Apartment Available Jun 1, 2026

24 Chetwynd Rd

24 Chetwynd RdSomerville, MA 02144
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14 Dow St, Unit 2
$6,375
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,375
Total Monthly Price
$6,375
5 Bedroom Apartment Available Now

14 Dow St, Unit 2

14 Dow StSomerville, MA 02144
Cost Per Sq.Ft.
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14 Dow St, Unit 2
$6,375
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,375
Total Monthly Price
$6,375
5 Bedroom Apartment Available Jun 1, 2026

14 Dow St, Unit 2

14 Dow StSomerville, MA 02144
Cost Per Sq.Ft.
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185 Powder House Blvd, Unit 2
$6,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500
Total Monthly Price
$6,500
5 Bedroom Apartment Available Jun 1, 2026

185 Powder House Blvd, Unit 2

185 Powder House BlvdSomerville, MA 02144
Cost Per Sq.Ft.
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57 Quincy St
$6,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500
Total Monthly Price
$6,500
5 Bedroom Apartment Available Now

57 Quincy St

57 Quincy StMedford, MA 02155
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136 Burget Ave
$6,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500
Total Monthly Price
$6,500
5 Bedroom Apartment Available Now

136 Burget Ave

136 Burget AveMedford, MA 02155
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136 Burget Ave
$6,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500
Total Monthly Price
$6,500
5 Bedroom Apartment Available Now

136 Burget Ave

136 Burget AveMedford, MA 02155
Cost Per Sq.Ft.
  • Smoke Free
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80 Curtis St, Unit House
$6,550
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,550
Total Monthly Price
$6,550
6 Bedroom Apartment Available Now

80 Curtis St, Unit House

80 Curtis StSomerville, MA 02144
Cost Per Sq.Ft.
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16 Chetwynd Rd, Unit 1
$6,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,600
Total Monthly Price
$6,600
6 Bedroom Apartment Available Now

16 Chetwynd Rd, Unit 1

16 Chetwynd RdSomerville, MA 02144
Cost Per Sq.Ft.
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4 High St
$6,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,600
Total Monthly Price
$6,600
6 Bedroom Apartment Available Jun 1, 2026

4 High St

4 High StSomerville, MA 02144
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76 Curtis St, Unit 1
$6,640
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,640
Total Monthly Price
$6,640
5 Bedroom Apartment Available Jun 1, 2026

76 Curtis St, Unit 1

76 Curtis StSomerville, MA 02144
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24 Greenleaf Ave, Unit 2
$6,750
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,750
Total Monthly Price
$6,750
5 Bedroom Apartment Available Jun 1, 2026

24 Greenleaf Ave, Unit 2

24 Greenleaf AveMedford, MA 02155
Cost Per Sq.Ft.
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24 Greenleaf Ave, Unit 2
$6,750
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,750
Total Monthly Price
$6,750
5 Bedroom Apartment Available Jun 1, 2026

24 Greenleaf Ave, Unit 2

24 Greenleaf AveMedford, MA 02155
Cost Per Sq.Ft.
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59 Sunset Rd, Unit 2
$7,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,500
Total Monthly Price
$7,500
5 Bedroom Apartment Available Jun 1, 2026

59 Sunset Rd, Unit 2

59 Sunset RdSomerville, MA 02144
Cost Per Sq.Ft.
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17 Tesla Ave
$7,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,800
Total Monthly Price
$7,800
6 Bedroom Apartment Available Now

17 Tesla Ave

17 Tesla AveMedford, MA 02155
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19 Shirley Rd, Unit 19
$8,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,000
Total Monthly Price
$8,000
4 Bedroom Apartment Available Now

19 Shirley Rd, Unit 19

19 Shirley RdMedford, MA 02155
Cost Per Sq.Ft.
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17 Tesla Ave, Unit #2
$8,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,100
Total Monthly Price
$8,100
6 Bedroom Apartment Available Now

17 Tesla Ave, Unit #2

17 Tesla AveMedford, MA 02155
Cost Per Sq.Ft.
  • Smoke Free
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80 Curtis St, Unit 1
$8,437
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,437
Total Monthly Price
$8,437
6 Bedroom Apartment Available Jun 1, 2026

80 Curtis St, Unit 1

80 Curtis StSomerville, MA 02144
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40 George St
$8,450
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,450
Total Monthly Price
$8,450
6 Bedroom Apartment Available Jun 1, 2026

40 George St

40 George StMedford, MA 02155
Cost Per Sq.Ft.
property at 269 Cambridge Rd

269 Cambridge Rd

WoburnMA01801
property at 361 Alewife Brook Pkwy

361 Alewife Brook Pkwy

SomervilleMA02144
property at 79 Franklin St

79 Franklin St

StonehamMA02180
property at 19 Lincoln St

19 Lincoln St

MedfordMA02155
property at 21-23-23 Bow St

21-23-23 Bow St

ArlingtonMA02474
Showing Results 201-250, Page 5 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 152 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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