
Luxury Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA (36 Rentals)
The most luxurious Homes in the Winchester Highlands area of Winchester with high-end amenities, features, and finishes.


2 George Rd

5 Sheridan Cir, Unit 5, Unit 5

31 Irving St

8 Richardson St

18 Grant Rd

31 Fells Rd

34 Glen Rd

200 Swanton St, Unit 635, Unit 635
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

200 Swanton St, Unit 237, Unit 237

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
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.

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

39 Franklin St

4 Kilby St
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.

1 Main St

6 Stratton Dr

16 Kilby St

380 Place Ln

7 Carol St

18 Eaton Ave

99 Garfield Ave

17 St Denis Ave

7 Spring Ct
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 a home in Winchester Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Highlands 2 Bedroom Homes for Rent | $2,794 | $2,300 | $4,500 |
| Winchester Highlands 3 Bedroom Homes for Rent | $4,240 | $2,500 | $8,000 |
| Winchester Highlands 4 Bedroom Homes for Rent | $4,578 | $3,100 | $7,900 |
| Winchester Highlands 5 Bedroom Homes for Rent | $15,497 | $5,995 | $10,000+ |
| Winchester Highlands 6 Bedroom Homes for Rent | $5,497 | $5,497 | $5,497 |
| Winchester Highlands 7 Bedroom Homes for Rent | $12,000 | $10,000 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 36 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 125 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,500 to $12,505. There are also 62 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,890 to $25,000.
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 $1,890 to $25,000 with an average monthly rent of $6,099.
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 $3,500 to $5,573, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $8,000. Four Bedroom Single-Family rentals are also available starting from $3,100 and Four Bedroom Apartments start at $3,100.
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

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
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.