
Luxury Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA (28 Rentals)
The most luxurious Apartments in the Winchester Highlands area of Winchester with high-end amenities, features, and finishes.


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10 Webster St, Unit 1

20 Hancock St

415 Washington St

846 Main St

36 Cross St

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The Devon at Weiss Farm
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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Hanover Stoneham

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The Mave

Mill Street Heights

44 Montvale Avenue

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Alta Clara

48 Pleasant Street

Lofts at 307 Main LLC
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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162 Montvale Ave, Unit 162A

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7 Lowell St

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159 Main St

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505 Main St, Unit 1

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286 Main St, Unit 3

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477 Fulton St, Unit F

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107 Belle Ave
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.

39 Cottage St

489 Main St

36 Stevens St

224 Park St

79 Franklin St

59 Mill St

29 Garfield Ave
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
Winchester Highlands, Winchester, MA Local Guide

How much does it cost to rent an apartment in Winchester Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Highlands Studio Apartments | $2,376 | $1,780 | $2,720 |
| Winchester Highlands 1 Bedroom Apartments | $2,753 | $1,850 | $4,195 |
| Winchester Highlands 2 Bedroom Apartments | $3,511 | $2,250 | $4,920 |
| Winchester Highlands 3 Bedroom Apartments | $4,323 | $2,700 | $6,900 |
| Winchester Highlands 4 Bedroom Apartments | $4,500 | $4,150 | $5,200 |
Browse Apartments in this Neighborhood
There are currently 28 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
See all Apartments in WinchesterExplore Winchester
Frequently Asked Questions about Winchester Highlands
How much are Studio apartments in Winchester Highlands?
There are currently 41 Studio Apartments in Winchester Highlands with rent ranges from $1,780 to $2,720 with an average price of $2,376.
What is the current price range for One Bedroom Winchester Highlands Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Winchester Highlands ranges from $1,850 to $4,195 with an average monthly rent of $2,753.
What does renting a Two Bedroom Apartment in Winchester Highlands cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester Highlands range from $2,250 to $4,920. Today's average rental price for Two Bedrooms here is $3,511.
How expensive are Winchester Highlands Three Bedroom Apartments?
There are currently 19 Three Bedroom Apartments listings available in Winchester Highlands on ApartmentHomeLiving.com. The pricing ranges from $2,700 to $6,900 - averaging $4,323 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

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.

Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
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.