
Luxury Apartments for Rent in Winchester, MA (260 Rentals) Page 2 of 6
The most luxurious Apartments in Winchester with high-end amenities, features, and finishes.


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293 Boston Ave, Unit 2

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96 Conwell Ave, Unit 2

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29 Capen St, Unit #2

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1 Victoria St, Unit #1A

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29 Capen St, Unit 2

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50 Whitfield Rd, Unit 1

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79 Capen St, Unit 2

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186 Powder House Blvd, Unit 2

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65 Sterling St, Unit 1
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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69 Conwell Ave

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69 Conwell Ave, Unit 1

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1 Victoria St

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376 Massachusetts Ave, Unit 32

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373 Boston Ave

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5 Freeman St, Unit 2

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5 Freeman St, Unit 1

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5 Freeman St, Unit 1

48 Pleasant Street

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73 Gordon St, Unit 1

14 Belknap St

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67 Orchard St, Unit 1

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50 Hamilton St, Unit 2

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26 Bradlee Rd, Unit 05

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92 Sylvia St, Unit 2

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36 Sherman St, Unit 2

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26 Bradlee Rd

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22 Bradlee Rd, Unit 405

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26 Bradlee Rd, Unit 3

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96 Conwell Ave, Unit 2

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96 Conwell Ave, Unit 1

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224 Arlington St

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77 Fairfax St, Unit #1

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258 Boston Ave, Unit 3

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90 North St, Unit 1

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48 Chester Ave, Unit 1

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258 Boston Ave, Unit 2

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Arlington 360

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49 Conwell Ave, Unit 2

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104 W Quincy St, Unit 1

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41 Belknap St, Unit 2

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41 Belknap St, Unit 2

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1 Victoria St, Unit 1A

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258 Boston Ave, Unit 3

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69 Conwell Ave, Unit 1L

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35 Whitfield Rd, Unit #3

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124 Forest St, Unit 1

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148 George St, Unit 2L

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124 Forest St, Unit 1

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124 Forest St, Unit 1
Winchester, MA Local Guide

How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Luxury Studio Apartments | $2,189 | $1,700 | $2,731 |
| Winchester Luxury 1 Bedroom Apartments | $2,692 | $1,600 | $4,355 |
| Winchester Luxury 2 Bedroom Apartments | $3,246 | $2,000 | $5,150 |
| Winchester Luxury 3 Bedroom Apartments | $3,672 | $2,300 | $5,761 |
| Winchester Luxury 4 Bedroom Apartments | $4,450 | $3,300 | $6,000 |
| Winchester 5 Bedroom Apartments | $6,108 | $1,110 | $10,000+ |
| Winchester 6 Bedroom Apartments | $7,151 | $5,300 | $8,437 |
Browse Top Apartments in Winchester
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Frequently Asked Questions about Winchester
How much are Studio apartments in Winchester?
There are currently 105 Studio Apartments in Winchester with rent ranges from $1,700 to $2,731 with an average price of $2,189.
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 $1,600 to $4,355 with an average monthly rent of $2,692.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $2,000 to $5,150. Today's average rental price for Two Bedrooms here is $3,246.
How expensive are Winchester Three Bedroom Apartments?
There are currently 94 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,300 to $5,761 - averaging $3,672 for the location.
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.
Helpful Local Expert Guides

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.

A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!

Explore Like a Local: The Insider's Guide to Boston
Written by: Amelia Ramstead
Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.

Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.