177 Central St
StonehamMA02180
Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA (175 Rentals) Page 2 of 4
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
300 Park Terrace Dr, Unit 343
300 Park Terrace Dr
StonehamMA02180
6 Johnson St
WoburnMA01801
555 Main St
WoburnMA01801
479 Fulton St
MedfordMA02155
close
View Me
$2,6002 Bedroom Apartments Available Now
66 Mill St, Unit 8
66 Mill StWoburn, MA 01801
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
$2,5002 Bedroom Apartments Available Now
50 Mill St, Unit 5
50 Mill StWoburn, MA 01801
close
View Me
$5,4976 Bedroom Apartments Available Now
36 Gould St
36 Gould StStoneham, MA 02180
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.
close
View Me
$2,5002 Bedroom Apartments Available Now
62 Mill St, Unit 6
62 Mill StWoburn, MA 01801
close
View Me
$8,759
Total Monthly Price
5 Bedroom Apartments Available Dec 26Total Monthly Price
Base Rent
$8,328
Required Monthly Fees
$431
Total Monthly Price
$8,759
3 Chapel Way, Unit SI ID1387521P
3 Chapel WayStoneham, MA 02180
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
2 Peabody Rd
StonehamMA02180
50 Lee St
StonehamMA02180
39 Montvale Ave
WoburnMA01801
49 Prospect St
WoburnMA01801
99 Garfield Ave
WoburnMA01801
80 N Warren St
WoburnMA01801
10 Davis St
WoburnMA01801
146 Marble St
StonehamMA02180
533-535-535 Main St
StonehamMA02180
35 Arlington St
WoburnMA01801
20 Bryant St
WoburnMA01801
426 Main St
StonehamMA02180
27 Highland St
WoburnMA01801
22 Emerson St
StonehamMA02180
4 Rowe St
StonehamMA02180
35 Prospect St
WoburnMA01801
74 Beach St
WoburnMA01801
1 Main St
WoburnMA01801
182 Central St
StonehamMA02180
15 Wason St
MedfordMA02155
555 Main St
WoburnMA01801
28 Park Ave
MedfordMA02155
50 Belle Ave
MedfordMA02155
100 Place Ln
WoburnMA01801
380 Place Ln
WoburnMA01801
282 Place Ln
WoburnMA01801
74 Beach St, Unit 5-1
74 Beach St
WoburnMA01801
84 Franklin St, Unit 2
84 Franklin St
StonehamMA02180
close
View Me
1 to 3 Bedroom Apartments
Montvale Condominiums
100-200 Ledgewood DrStoneham, MA 02180
close
View Me
2 Bedroom Apartments
Sterling Hill Stoneham
11 Executive DrStoneham, MA 02180
close
View Me
3 Bedroom Apartments
474-482 Main St
474-482 Main StWoburn, MA 01801
close
View Me
Studio Apartments
Park Terrace
291 W Wyoming AveStoneham, MA 02180
close
View Me
1 to 2 Bedroom Apartments
The Willows at Winchester
7 Conant RdWinchester, MA 01890
close
View Me
2 to 3 Bedroom Apartments
The Village
171 Swanton StWinchester, MA 01890
Showing Results 51-100, Page 2 of 4
Winchester Highlands, Winchester, MA Local Guide
How much does it cost to rent an apartment in Winchester Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Highlands Studio Apartments | $2,510 | $2,050 | $3,001 |
| Winchester Highlands 1 Bedroom Apartments | $2,937 | $1,695 | $4,070 |
| Winchester Highlands 2 Bedroom Apartments | $3,636 | $2,400 | $5,350 |
| Winchester Highlands 3 Bedroom Apartments | $4,831 | $2,800 | $5,628 |
| Winchester Highlands 4 Bedroom Apartments | $3,600 | $3,500 | $3,700 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
How much does it cost to rent a home in Winchester Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| 2 Bedroom Homes | $2,896 | $2,300 | $3,700 |
| 3 Bedroom Homes | $4,783 | $2,900 | $6,500 |
| 4 Bedroom Homes | $5,532 | $2,850 | $10,000+ |
| 5 Bedroom Homes | $8,598 | $5,295 | $10,000+ |
| 6 Bedroom Homes | $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 Apartments in this Neighborhood
There are currently 175 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
See all Apartments in WinchesterExplore 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 is the current pricing and availability for apartments for rent in the Winchester Highlands area of Winchester, MA?
As of today, August 07, 2026, there are currently 175 available Winchester Highlands apartments priced from $1,695 to $20,951, with an average monthly rent of $3,317.
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
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.