
Luxury Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA (58 Rentals)
The most luxurious Homes in the Winchester Highlands area of Winchester with high-end amenities, features, and finishes.


270 Cross St

171 Swanton St

345 Washington St, Unit 1

345 Washington St

271 Washington St

270 Cross St

8 Charles Rd

115 Washington St

24-26-26 Kirk St
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

64 Highland Ave

476 Fulton St

476 Fulton St

476 Fulton St, Unit 476

476 Fulton St

476 Fulton St, Unit 476

476 Fulton St

476 Fulton St

476 Fulton St, Unit #0

476 Fulton St

476 Fulton St

476 Fulton St

477 Fulton St, Unit T

480 Fulton St

470 Fulton St, Unit 301

476 Fulton St

482 Fulton St

476 Fulton St

482 Fulton St

479 Fulton St, Unit #0

480 Fulton St, Unit 478

476 Fulton St

477 Fulton St

476 Fulton St

696 Fulton St

39 Winford Way, Unit 1

8 Vera Ln

25 Arlington Rd, Unit 3

68 Central St

289 Elm St, Unit 14

474 Fulton St

476 Fulton St

472 Fulton St

478 Fulton St

39 Beacon St

8 Lee St

201 Main St

8 Stephanie Cir

52 High St

10 Stephanie Cir
Winchester Highlands, Winchester, MA Local Guide

How much does it cost to rent a home in Winchester Highlands?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Winchester Highlands 2 Bedroom Homes for Rent | $2,831 | $2,500 | $3,800 |
Winchester Highlands 3 Bedroom Homes for Rent | $3,375 | $2,800 | $4,200 |
Winchester Highlands 4 Bedroom Homes for Rent | $5,281 | $4,800 | $6,000 |
Winchester Highlands 5 Bedroom Homes for Rent | $5,920 | $2,800 | $7,000 |
Browse Homes for Rent in this Neighborhood
There are currently 58 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
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Winchester Highlands, Winchester, MA Local Guide
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Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 148 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,750 to $7,135. There are also 65 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,895 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 $1,895 to $7,000 with an average monthly rent of $3,608.
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 $7,135, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $4,200. Four Bedroom Single-Family rentals are also available starting from $4,800 and Four Bedroom Apartments start at $4,200.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.

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.

Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.

Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.