
Luxury Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA (53 Rentals)
The most luxurious Homes in the Winchester Highlands area of Winchester with high-end amenities, features, and finishes.


60 Lake St

848 Main St

10 Farrow St

35 Vine St

60 Lake St

104 Wendell St

192 Cross St

271 Washington St

10 Farrow St

10 Hillcrest Pkwy

211 Forest St

54 Wedgemere Ave

22 James St

289 Elm St, Unit 14

29 Arlington Rd, Unit 01

133 Franklin St, Unit 502

22 Central St, Unit A

107 Belle Ave

107 Belle Ave

107 Belle Ave

107 Belle Ave

107 Belle Ave

107 Belle Ave

40 Campbell St

10 Harvard Street Ext

13 Garfield Ave

479 Fulton St

480 Fulton St, Unit 478

476 Fulton St, Unit 476

476 Fulton St

477 Fulton St, Unit T

3 Boline Pl

1 Boline Pl

22 Green St

100 Fellsview Terrace

373 Salem St

200 Park Terrace Dr

19 Allen St

20 Marble St

2 Clark St

305 Salem St

200 Ledgewood Dr

107 Belle Ave

295 W Wyoming Ave

10 Gould St

7-9 Stephanie Cir

10 Harvard Street Extension

1 Mauriello Dr
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 | $2,795 | $2,200 | $3,750 |
Winchester Highlands 3 Bedroom Homes for Rent | $3,672 | $2,900 | $4,800 |
Winchester Highlands 4 Bedroom Homes for Rent | $5,459 | $3,825 | $8,000 |
Winchester Highlands 5 Bedroom Homes for Rent | $6,411 | $4,600 | $10,000+ |
Winchester Highlands 6 Bedroom Homes for Rent | $13,500 | $10,000 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 53 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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Pet Friendly LifestyleWinchester Highlands, Winchester, MA
Ranked #2
Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.5Pet Friendly
Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 117 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,550 to $7,500. There are also 70 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,200 to $13,500.
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 $1,200 to $13,500 with an average monthly rent of $5,080.
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.

The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.