
Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA (64 Rentals)


2 Elmwood Ave

2 Elmwood Ave

2 Elmwood Ave

4 Quigley Ct

21 Park Ave

271 Washington St

7 Conant Rd

200 Swanton St

11 Elmwood Ave
Boston's Best Affordable Neighborhoods
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400 Cross St

2 Rangeley Rd

113 Cambridge St

8 Albamont Rd

20 Lebanon St, Unit 22

200 Swanton St

120 Fellsview Ter, Unit 123

9 Washington Ave

100 Ledgewood Dr, Unit 515

264 Main St
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.

39 Cottage St, Unit 1

14 Church Ave, Unit Unit 2A

27 Arlington Rd, Unit 5

177 Central St

200 Park Terrace Dr, Unit 222

289 Elm St, Unit 14

289 Elm St, Unit 14

12 Davis St

841 Fellsway W

60 Haines St
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Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

60 Haines St

165 Gaston St

476 Fulton St, Unit Unit 478

476 Fulton St

480 Fulton St, Unit 478

476 Fulton St, Unit 476

476 Fulton St

107 Belle Ave, Unit 107

107 Belle Ave

182 Central St
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.

52 Mill St

489 Main St

60 Haines St

99 Garfield Ave

71 Montvale Ave

200 Ledgewood Dr

12 Gould St

35 Prospect St

56 Warren Ave

36 Union St
Winchester Highlands, Winchester, MA Local Guide

How much does it cost to rent a home in Winchester Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Highlands 2 Bedroom Homes for Rent | $2,801 | $2,075 | $5,350 |
| Winchester Highlands 3 Bedroom Homes for Rent | $3,324 | $2,500 | $4,200 |
| Winchester Highlands 4 Bedroom Homes for Rent | $4,810 | $3,990 | $5,300 |
| Winchester Highlands 5 Bedroom Homes for Rent | $5,323 | $2,800 | $7,000 |
Browse Homes for Rent in this Neighborhood
There are currently 64 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
Explore Winchester
Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 122 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,780 to $6,900. There are also 64 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,850 to $7,000.
What is the current price range for Rental Homes in Winchester Highlands?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester Highlands ranges from $1,850 to $7,000 with an average monthly rent of $3,366.
How much are larger Three and Four Bedroom Rentals in Winchester Highlands?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester Highlands range from $2,700 to $6,900, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $4,200. Four Bedroom Single-Family rentals are also available starting from $3,990 and Four Bedroom Apartments start at $4,150.
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.
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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.