Luxury Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA (71 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Lifestyle Matching SearchDone
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

The most luxurious Apartments in the Winchester Highlands area of Winchester with high-end amenities, features, and finishes.

close
View Me
10 Webster St, Unit 1
$3,700
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700
4 Bedroom Apartment Available Aug 15

10 Webster St, Unit 1

10 Webster StWinchester, MA 01890
Cost Per Sq.Ft.
  • Smoke Free
property at 270 Cross St

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 4 Bath Home for Rent

Available Sep 1

270 Cross St

WinchesterMA01890
property at 161 Highland Ave

$8,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,500

Total Monthly Price
$8,500

6 Bedroom, 2.5 Bath Home for Rent

Available Now

161 Highland Ave

WinchesterMA01890
property at 10-12-12 Webster St

$3,700

Total Monthly Price

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

4 Bedroom, 1.5 Bath Home for Rent

Available Now

10-12-12 Webster St

WinchesterMA01890
property at 926 Main St

$2,900

Total Monthly Price

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Home for Rent

Available Sep 1

926 Main St

WinchesterMA01890
property at 63-65 Harvard St

$3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 2 Bath Townhome for Rent

Available Now

63-65 Harvard St

WinchesterMA01890
property at 22 Baldwin St

$4,500

Total Monthly Price

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

3 Bedroom, 2 Bath Home for Rent

Available Aug 10

22 Baldwin St

WinchesterMA01890
property at 488 Washington St

$4,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,650

Total Monthly Price
$4,650

4 Bedroom, 1.5 Bath Home for Rent

Available Now

488 Washington 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

property at 17 Churchill Rd

$5,500

Total Monthly Price

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

5 Bedroom, 3.5 Bath Home for Rent

Available Aug 15

17 Churchill Rd

WinchesterMA01890
property at 111 Highland Ave

$5,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

3 Bedroom, 2.5 Bath Home for Rent

Available Now

111 Highland Ave

WinchesterMA01890
property at 270 Cross St

$6,000

Total Monthly Price

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 4 Bath Home for Rent

Available Sep 1

270 Cross St

WinchesterMA01890
property at 31 Fells Rd

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

3 Bedroom, 2 Bath Home for Rent

Available Now

31 Fells Rd

WinchesterMA01890
property at 60 Graystone Circle

$6,500

Total Monthly Price

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

3 Bedroom, 2.5 Bath Townhome for Rent

Available Now

60 Graystone Circle

WinchesterMA01890
property at 18 Grant Rd

$6,995

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,995

Total Monthly Price
$6,995

4 Bedroom, 2.5 Bath Home for Rent

Available Now

18 Grant Rd

WinchesterMA01890
property at 161 Highland Ave

$8,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,500

Total Monthly Price
$8,500

6 Bedroom, 2 Bath Home for Rent

Available Now

161 Highland Ave

WinchesterMA01890
property at 63 Holland St

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

2 Bedroom, 1 Bath Home for Rent

Available Now

63 Holland St

WinchesterMA01890
close
View Me
Hanover Stoneham
Rent Specials
$2,256 - $5,628
Total Monthly Price

Total Monthly Price

Base Rent
$2,256 - $5,628

Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

Hanover Stoneham

95 Maple StStoneham, MA 02180
Luxury
  • Verified
  • Customer Reviewed
  • Utilities Included

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.

close
View Me
The Mave
Rent Specials
$2,695 - $5,350
Total Monthly Price1 Month Lease Term

Total Monthly Price

Base Rent
$2,695 - $5,350

Total Monthly Price
Varies
1 to 2 Bedroom Apartments Available Now

The Mave

225 Fallon RdStoneham, MA 02180
Family Friendly
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
Alta Clara
$2,830 - $5,604
Total Monthly Price

Total Monthly Price

Base Rent
$2,830 - $5,604

Total Monthly Price
Varies
1 to 2 Bedroom Apartments Available Now

Alta Clara

21 Executive DrStoneham, MA 02180
Family Friendly
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
48 Nashua St, Unit 2
$2,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500
2 Bedroom Apartment Available Now

48 Nashua St, Unit 2

48 Nashua StWoburn, MA 01801
Cost Per Sq.Ft.
  • Smoke Free
close
View Me
722 Highland Ave, Unit 2
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
3 Bedroom Apartment Available Now

722 Highland Ave, Unit 2

722 Highland AveMalden, MA 02148
Cost Per Sq.Ft.
  • Smoke Free

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.

property at 289 Elm St

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 2 Bath Condo for Rent

Available Now

289 Elm St, Unit 14

289 Elm St
MedfordMA02155
property at 177 Central St

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Now

177 Central St

StonehamMA02180
property at 300 Park Terrace Dr

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Aug 15

300 Park Terrace Dr, Unit 343

300 Park Terrace Dr
StonehamMA02180
property at 73 Main St

$3,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

3 Bedroom, 1.5 Bath Home for Rent

Available Sep 1

73 Main St

WoburnMA01801
property at 555 Main St

$3,350

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,350

Total Monthly Price
$3,350

2 Bedroom, 2.5 Bath Townhome for Rent

Available Oct 1

555 Main St

WoburnMA01801
property at 40 Campbell St

$3,855

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,855

Total Monthly Price
$3,855

4 Bedroom, 2 Bath Home for Rent

Available Oct 1

40 Campbell St

WoburnMA01801
property at 6 Johnson St

$4,000

Total Monthly Price1 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

4 Bedroom, 1 Bath Townhome for Rent

Available Now

6 Johnson St

WoburnMA01801
property at 479 Fulton St

$5,295

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,295

Total Monthly Price
$5,295

5 Bedroom, 4.5 Bath Condo for Rent

Available Now

479 Fulton St

MedfordMA02155
property at 64 Newcomb Rd

$15,000

Total Monthly Price1 Month Lease Term

Total Monthly Price

Base Rent
$15,000

Total Monthly Price
$15,000

5 Bedroom, 4 Bath Home for Rent

Available Now

64 Newcomb Rd

StonehamMA02180

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.

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.

Frequently Asked Questions about Winchester Highlands

How much are Studio apartments in Winchester Highlands?

There are currently 38 Studio Apartments in Winchester Highlands with rent ranges from $2,050 to $3,001 with an average price of $2,510.

What is the current price range for One Bedroom Winchester Highlands Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Winchester Highlands ranges from $1,695 to $4,070 with an average monthly rent of $2,937.

What does renting a Two Bedroom Apartment in Winchester Highlands cost?

The monthly rent prices of Two Bedroom Apartments currently available in Winchester Highlands range from $2,400 to $5,350. Today's average rental price for Two Bedrooms here is $3,636.

How expensive are Winchester Highlands Three Bedroom Apartments?

There are currently 15 Three Bedroom Apartments listings available in Winchester Highlands on ApartmentHomeLiving.com. The pricing ranges from $2,800 to $5,628 - averaging $4,831 for the location.

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

decorative image for Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move article

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.

decorative image for What It Really Costs to Live in Boston: A Local Renter's Guide article

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.

decorative image for Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities article

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!

decorative image for Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert   article

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

decorative image for First Apartment Regrets: Real Renters Share What They'd Do Differently article

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.

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

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.

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention   article

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.

decorative image for How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide article

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.