Luxury Apartments for Rent in Winchester, MA (327 Rentals) Page 2 of 7

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

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29 Capen St
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
2 Bedroom Apartment Available Now

29 Capen St

29 Capen StMedford, MA 02155
Affordability
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22 Bradlee Rd
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
2 Bedroom Apartment Available Now

22 Bradlee Rd

22 Bradlee RdMedford, MA 02155
Affordability
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29 Capen St
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
2 Bedroom Apartment Available Now

29 Capen St

29 Capen StMedford, MA 02155
Affordability
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50 Hamilton St, Unit 2
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Now

50 Hamilton St, Unit 2

50 Hamilton StMedford, MA 02155
Affordability
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96 Conwell Ave, Unit 2
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Nov 1

96 Conwell Ave, Unit 2

96 Conwell AveSomerville, MA 02144
Affordability

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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67 Orchard St, Unit 1
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Nov 1

67 Orchard St, Unit 1

67 Orchard StMedford, MA 02155
Affordability
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60 Hamilton St, Unit 1
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Nov 1

60 Hamilton St, Unit 1

60 Hamilton StMedford, MA 02155
Affordability
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29 Capen St, Unit #2
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
2 Bedroom Apartment Available Now

29 Capen St, Unit #2

29 Capen StMedford, MA 02155
Cost Per Sq.Ft.
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1 Victoria St, Unit #1A
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
2 Bedroom Apartment Available Now

1 Victoria St, Unit #1A

1 Victoria StSomerville, MA 02144
Cost Per Sq.Ft.
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66 North St
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
2 Bedroom Apartment Available Now

66 North St

66 North StSomerville, MA 02144
Affordability
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294 Boston Ave, Unit 1
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Nov 1

294 Boston Ave, Unit 1

294 Boston AveMedford, MA 02155
Affordability
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224 Arlington St
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Nov 1

224 Arlington St

224 Arlington StMedford, MA 02155
Affordability
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9 Irving St, Unit 1
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Now

9 Irving St, Unit 1

9 Irving StMedford, MA 02155
Affordability

Boston's Best Affordable Neighborhoods

Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead

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49 Conwell Ave, Unit 2
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Now

49 Conwell Ave, Unit 2

49 Conwell AveSomerville, MA 02144
Cost Per Sq.Ft.
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49 Conwell Ave, Unit 2
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Now

49 Conwell Ave, Unit 2

49 Conwell AveSomerville, MA 02144
Cost Per Sq.Ft.
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59 Quincy St, Unit 1
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Nov 1

59 Quincy St, Unit 1

59 Quincy StMedford, MA 02155
Furnished
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50 Marion Rd, Unit 1
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
2 Bedroom Apartment Available Now

50 Marion Rd, Unit 1

50 Marion RdArlington, MA 02474
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48 Chester Ave, Unit 1
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Nov 1

48 Chester Ave, Unit 1

48 Chester AveMedford, MA 02155
Affordability
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293 Boston Ave, Unit 2
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Nov 1

293 Boston Ave, Unit 2

293 Boston AveMedford, MA 02155
Affordability
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48 Summer St, Unit 1
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Dec 1

48 Summer St, Unit 1

48 Summer StMedford, MA 02155
Cost Per Sq.Ft.
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69 Conwell Ave, Unit 1
$3,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100
3 Bedroom Apartment Available Now

69 Conwell Ave, Unit 1

69 Conwell AveSomerville, MA 02144
Affordability
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34 Sunset Rd, Unit 2
$3,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100
3 Bedroom Apartment Available Now

34 Sunset Rd, Unit 2

34 Sunset RdSomerville, MA 02144
Affordability
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234 Fulton St, Unit 1
$3,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100
3 Bedroom Apartment Available Now

234 Fulton St, Unit 1

234 Fulton StMedford, MA 02155
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34 Sunset Rd, Unit 2
$3,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100
3 Bedroom Apartment Available Nov 1

34 Sunset Rd, Unit 2

34 Sunset RdSomerville, MA 02144
Affordability
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34 Sunset Rd, Unit 2
$3,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100
3 Bedroom Apartment Available Now

34 Sunset Rd, Unit 2

34 Sunset RdSomerville, MA 02144
Affordability
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34 Sunset Rd, Unit 2
$3,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100
3 Bedroom Apartment Available Now

34 Sunset Rd, Unit 2

34 Sunset RdSomerville, MA 02144
Affordability
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14 Belknap St, Unit 2
$3,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100
3 Bedroom Apartment Available Now

14 Belknap St, Unit 2

14 Belknap StSomerville, MA 02144
Cost Per Sq.Ft.
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14 Belknap St, Unit 3
$3,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100
3 Bedroom Apartment Available Now

14 Belknap St, Unit 3

14 Belknap StSomerville, MA 02144
Cost Per Sq.Ft.
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108 W Quincy St, Unit 108
$3,150
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,150

Total Monthly Price
$3,150
3 Bedroom Apartment Available Now

108 W Quincy St, Unit 108

108 W Quincy StSomerville, MA 02144
Affordability
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73 Gordon St, Unit 1
$3,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200
3 Bedroom Apartment Available Now

73 Gordon St, Unit 1

73 Gordon StSomerville, MA 02144
Affordability
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39 Wildwood Ave, Unit 39 Wildwood
$3,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200
3 Bedroom Apartment Available Dec 1

39 Wildwood Ave, Unit 39 Wildwood

39 Wildwood AveArlington, MA 02476
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136 Sharon St
$3,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200
2 Bedroom Apartment Available Now

136 Sharon St

136 Sharon StMedford, MA 02155
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79 Conwell Ave, 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 Jun 1, 2026

79 Conwell Ave, Unit 1

79 Conwell AveSomerville, MA 02144
Affordability
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89 Hillsdale Rd, 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

89 Hillsdale Rd, Unit 1

89 Hillsdale RdMedford, MA 02155
Cost Per Sq.Ft.

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

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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Apartment Common Area Rules: What Renters Need to Know

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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.

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How to Negotiate Your Apartment Lease and Save Money

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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.