
Luxury Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA (67 Rentals)
The most luxurious Apartments in the Winchester Highlands area of Winchester with high-end amenities, features, and finishes.


Total Monthly Price
10 Webster St, Unit 1

171 Swanton St

10-12-12 Webster St

35 Vine St

31 Irving St

60 Lake St

7 Conant Rd

63-65 Harvard St

16 Richardson St
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33 Nelson St

63 Holland St

67 Church St

41 Cross St

488 Washington St

31 Fells Rd

17 Churchill Rd

18 Grant Rd

34 Glen Rd

59 Wedgemere Ave
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Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

200 Swanton St, Unit T37

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The Devon at Weiss Farm

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Hanover Stoneham

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The Mave

44 Montvale Avenue

Mill Street Heights

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Alta Clara

Mill Street Gardens

Lofts at 307 Main LLC

79 Montvale Ave
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Total Monthly Price
159 Main St

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25 Arlington Rd, Unit Apt #3 6

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14 Salem St, Unit 3

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286 Main St, Unit 3

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16 Kilby St, Unit 3

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10 Davis St, Unit 10

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107 Belle Ave

289 Elm St, Unit 14

74 Beach St, Unit 6-12

295 W Wyoming Ave, Unit 1A
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40 Sturges St, Unit 1

841 Fellsway W

479 Fulton St

64 Newcomb Rd

Total Monthly Price
3 Chapel Way, Unit SI ID1387521P

36 Gould St

10 Davis St, Unit 2

286 Main St, Unit 206

16 Kilby St

99 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 | $2,356 | $1,700 | $2,700 |
| Winchester Highlands 1 Bedroom Apartments | $2,971 | $1,850 | $4,215 |
| Winchester Highlands 2 Bedroom Apartments | $3,664 | $2,200 | $5,440 |
| Winchester Highlands 3 Bedroom Apartments | $3,839 | $950 | $6,317 |
| Winchester Highlands 4 Bedroom Apartments | $3,550 | $2,900 | $4,000 |
Browse Apartments in this Neighborhood
There are currently 67 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 42 Studio Apartments in Winchester Highlands with rent ranges from $1,700 to $2,700 with an average price of $2,356.
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 $4,215 with an average monthly rent of $2,971.
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 $2,200 to $5,440. Today's average rental price for Two Bedrooms here is $3,664.
How expensive are Winchester Highlands Three Bedroom Apartments?
There are currently 14 Three Bedroom Apartments listings available in Winchester Highlands on ApartmentHomeLiving.com. The pricing ranges from $950 to $6,317 - averaging $3,839 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

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
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There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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.