
Luxury Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA (42 Rentals)
The most luxurious Homes in the Winchester Highlands area of Winchester with high-end amenities, features, and finishes.


35 Vine St

31 Irving St

60 Lake St

7 Conant Rd

63-65 Harvard St

16 Richardson St

63 Holland St
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.

33 Nelson St

67 Church St

41 Cross St

488 Washington St

31 Fells Rd

17 Churchill Rd

18 Grant Rd

34 Glen Rd
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
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59 Wedgemere Ave

200 Swanton St, Unit T37

289 Elm St, Unit 14

74 Beach St, Unit 6-12

40 Sturges St, Unit 1

295 W Wyoming Ave, Unit 1A

841 Fellsway W

479 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.

64 Newcomb Rd

Total Monthly Price
3 Chapel Way, Unit SI ID1387521P

36 Gould St

10 Davis St, Unit 2

286 Main St, Unit 206

16 Kilby St

39 Franklin St

558 Main 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.

220 Central St

202 Central St

16 Kilby St

1 Main St

20 Bryant St

282 Place Ln

6 Philips Rd

50 Belle Ave
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

186 Salem St

28 Park Ave
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 | $2,999 | $2,400 | $4,200 |
| Winchester Highlands 3 Bedroom Homes for Rent | $4,013 | $2,500 | $6,500 |
| Winchester Highlands 4 Bedroom Homes for Rent | $6,221 | $2,900 | $10,000+ |
| Winchester Highlands 5 Bedroom Homes for Rent | $12,381 | $5,295 | $10,000+ |
| Winchester Highlands 7 Bedroom Homes for Rent | $11,000 | $10,000 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 42 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 113 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $950 to $11,016. There are also 54 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,900 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 $1,900 to $25,000 with an average monthly rent of $6,435.
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 $950 to $6,704, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $6,500. Four Bedroom Single-Family rentals are also available starting from $2,900 and Four Bedroom Apartments start at $2,900.
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
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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
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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
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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

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
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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.

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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.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.