270 Cross St
WinchesterMA01890
Luxury Homes for Rent in the Winchester Highlands Neighborhood of Winchester, MA (45 Rentals)
The most luxurious Homes in the Winchester Highlands area of Winchester with high-end amenities, features, and finishes.
161 Highland Ave
WinchesterMA01890
171 Swanton St
WinchesterMA01890
63-65 Harvard St
WinchesterMA01890
22 Baldwin St
WinchesterMA01890
488 Washington St
WinchesterMA01890
17 Churchill Rd
WinchesterMA01890
111 Highland Ave
WinchesterMA01890
270 Cross St
WinchesterMA01890
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
31 Fells Rd
WinchesterMA01890
60 Graystone Circle
WinchesterMA01890
18 Grant Rd
WinchesterMA01890
161 Highland Ave
WinchesterMA01890
63 Holland St
WinchesterMA01890
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
177 Central St
StonehamMA02180
300 Park Terrace Dr, Unit 343
300 Park Terrace Dr
StonehamMA02180
73 Main St
WoburnMA01801
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
555 Main St
WoburnMA01801
40 Campbell St
WoburnMA01801
6 Johnson St
WoburnMA01801
479 Fulton St
MedfordMA02155
64 Newcomb Rd
StonehamMA02180
close
View Me
$20,951
Total Monthly Price
5 Bedroom Apartments Available Oct 22Total Monthly Price
Base Rent
$19,884
Required Monthly Fees
$1,067
Total Monthly Price
$20,951
64 Newcomb Rd, Unit SI FL4-ID1586668P
64 Newcomb RdStoneham, MA 02180
close
View Me
$5,4976 Bedroom Apartments Available Now
36 Gould St
36 Gould StStoneham, MA 02180
close
View Me
$2,6002 Bedroom Apartments Available Now
66 Mill St, Unit 8
66 Mill StWoburn, MA 01801
close
View Me
$2,5002 Bedroom Apartments Available Now
50 Mill St, Unit 5
50 Mill StWoburn, MA 01801
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
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.
close
View Me
$2,5002 Bedroom Apartments Available Now
62 Mill St, Unit 6
62 Mill StWoburn, MA 01801
close
View Me
$2,5002 Bedroom Apartments Available Now
68 Mill St, Unit 11
68 Mill StWoburn, MA 01801
6 Cross St
WoburnMA01801
28 Park Ave
MedfordMA02155
144 E Border Rd
MaldenMA02148
27 Highland St
WoburnMA01801
146 Marble St
StonehamMA02180
20 Bryant St
WoburnMA01801
1 Main St
WoburnMA01801
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.
4 Rowe St
StonehamMA02180
380 Place Ln
WoburnMA01801
282 Place Ln
WoburnMA01801
533-535-535 Main St
StonehamMA02180
555 Main St
WoburnMA01801
100 Place Ln
WoburnMA01801
15 Wason St
MedfordMA02155
50 Belle Ave
MedfordMA02155
28 Park Ave
MedfordMA02155
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.
Showing Results 1-45, Page 1 of 1
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 | $2,896 | $2,300 | $3,700 |
| Winchester Highlands 3 Bedroom Homes for Rent | $4,783 | $2,900 | $6,500 |
| Winchester Highlands 4 Bedroom Homes for Rent | $5,532 | $2,850 | $10,000+ |
| Winchester Highlands 5 Bedroom Homes for Rent | $8,598 | $5,295 | $10,000+ |
| Winchester Highlands 6 Bedroom Homes for Rent | $8,500 | $8,500 | $8,500 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 45 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
Explore Winchester
Let everyone know!
Do you know the Winchester Highlands area?
If you’re an expert on all things Winchester Highlands, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 116 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,695 to $20,951. There are also 59 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,800 to $15,000.
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 $1,800 to $15,000 with an average monthly rent of $4,167.
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 $2,800 to $5,628, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,900 to $6,500. Four Bedroom Single-Family rentals are also available starting from $2,850 and Four Bedroom Apartments start at $3,500.
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
Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
What It Really Costs to Live in Boston: A Local Renter's Guide
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com expert for Boston!
Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com expert for Boston, and I’m excited to help you find your next home!
Articles, How-To's, and Tips
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.
Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
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.