
Luxury Apartments for Rent in Winchester, MA (227 Rentals) Page 2 of 5
The most luxurious Apartments in Winchester with high-end amenities, features, and finishes.


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Arlington 360

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1 Victoria St

69 Raymond Ave

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69 Raymond Ave, Unit 69

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373 Boston Ave

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63 Newport St, Unit 63 Newport Street

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26 Bradlee Rd, Unit 05

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1 Victoria St, Unit 1A

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26 Bradlee Rd, Unit 3
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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22 Bradlee Rd, Unit 405

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14 Allen St, Unit 2

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77 Fairfax St, Unit #1

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41 Belknap St, Unit 2

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1 Victoria St, Unit 1A

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260 Boston Ave

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35 Upland Rd, Unit 2

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27 Orvis Rd, Unit 27 Orvis Rd

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333 Alewife Brook Pky, Unit 3

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333 Alewife Brook Pky, Unit 2
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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14 Belknap St, Unit 2

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38 George St, Unit 1

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235 Ashcroft Rd

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37 Clark St, Unit B

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68 North St

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112 College Ave

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276 Boston Ave, Unit B1

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79 Conwell Ave, Unit 3

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210 Powder House Blvd, Unit 1

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210 Powder House Blvd, 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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15 Taylor St, Unit 1

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178 Boston Ave, Unit 2

14 Belknap St

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585 High St, Unit Apt. 2

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15 Taylor St

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59 Quincy St

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165 Radcliffe Rd, Unit #169

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49 Sunset Rd, Unit 49

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231 Boston Ave, Unit 1

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118 W Adams St, Unit 118

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56 Gordon St, Unit 2

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56 Gordon St, Unit 2

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10 Pinkham Rd, Unit 2

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117 Burget Ave, Unit 1

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56 Gordon St, Unit 1

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52 Raymond Ave, Unit 2

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125 Hillsdale Rd, Unit 1

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125 Hillsdale Rd, Unit First

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119 Burget Ave

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3 Hamilton Rd, 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 | $2,248 | $1,650 | $2,832 |
| Winchester Luxury 1 Bedroom Apartments | $2,696 | $1,110 | $4,215 |
| Winchester Luxury 2 Bedroom Apartments | $3,356 | $1,995 | $5,440 |
| Winchester Luxury 3 Bedroom Apartments | $3,790 | $950 | $6,297 |
| Winchester Luxury 4 Bedroom Apartments | $4,172 | $2,900 | $5,300 |
| Winchester 5 Bedroom Apartments | $6,088 | $4,200 | $10,000+ |
| Winchester 6 Bedroom Apartments | $6,358 | $950 | $8,400 |
Browse Top Apartments in Winchester
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Frequently Asked Questions about Winchester
How much are Studio apartments in Winchester?
There are currently 103 Studio Apartments in Winchester with rent ranges from $1,650 to $2,832 with an average price of $2,248.
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 $1,110 to $4,215 with an average monthly rent of $2,696.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $1,995 to $5,440. Today's average rental price for Two Bedrooms here is $3,356.
How expensive are Winchester Three Bedroom Apartments?
There are currently 76 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $950 to $6,297 - averaging $3,790 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

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.