
Luxury Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA (69 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, Unit 1

200 Swanton St, Unit #303, Unit #303

2 George Rd

5 Sheridan Cir, Unit 5, Unit 5

9 Mt Vernon St

26 Lebanon St

10-12-12 Webster St

31 Irving St

8 Richardson St
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18 Grant Rd

31 Fells Rd

34 Glen Rd

200 Swanton St, Unit 635, Unit 635

200 Swanton St, Unit 237, Unit 237

Total Monthly Price
The Devon at Weiss Farm

Total Monthly Price
Hanover Stoneham

Total Monthly Price
The Mave

44 Montvale Avenue

Mill Street Heights
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Mill Street Gardens

Total Monthly Price
Alta Clara

79 Montvale Ave

Total Monthly Price
538 Main St, Unit 2, Unit 2

Total Monthly Price
21 Davis St, Unit 2, Unit 2

Total Monthly Price
159 Main St

Total Monthly Price
8 Eastern Ave, Unit 1st floor, Unit 1st floor

Total Monthly Price
68 Pleasant St, Unit #1, Unit #1

Total Monthly Price
14 Salem St, Unit 3, Unit 3

Total Monthly Price
286 Main St, Unit 3, Unit 3
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Total Monthly Price
16 Kilby St, Unit 3, Unit 3

Total Monthly Price
107 Belle Ave

289 Elm St, Unit 14, Unit 14

289 Elm St, Unit 1, Unit 1

39 Cottage St, Unit 1, Unit 1

40 Sturges St, Unit 1, Unit 1

151 Walsh St

11 Garfield Ave

476 Fulton St

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

476 Fulton St

480 Fulton St, Unit 478, Unit 478

36 Gould St

476 Fulton St, Unit 476, Unit 476

64 Newcomb Rd

Total Monthly Price
3 Chapel Way, Unit SI ID1387521P

16 Kilby St

550 Main St

198 Franklin St

137 Franklin St
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 | $2,329 | $1,500 | $2,700 |
| Winchester Highlands 1 Bedroom Apartments | $2,920 | $1,700 | $4,365 |
| Winchester Highlands 2 Bedroom Apartments | $3,519 | $2,250 | $5,440 |
| Winchester Highlands 3 Bedroom Apartments | $4,484 | $3,500 | $5,573 |
| Winchester Highlands 4 Bedroom Apartments | $3,650 | $3,100 | $4,150 |
Browse Apartments in this Neighborhood
There are currently 69 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 39 Studio Apartments in Winchester Highlands with rent ranges from $1,500 to $2,700 with an average price of $2,329.
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 $1,700 to $4,365 with an average monthly rent of $2,920.
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 $5,440. Today's average rental price for Two Bedrooms here is $3,519.
How expensive are Winchester Highlands Three Bedroom Apartments?
There are currently 15 Three Bedroom Apartments listings available in Winchester Highlands on ApartmentHomeLiving.com. The pricing ranges from $3,500 to $5,573 - averaging $4,484 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
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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!

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Articles, How-To's, and Tips

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
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This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

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Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

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.