close
View Me
$1,500Studio Apartments Available Now
2 Elmwood Ave, Unit 13
2 Elmwood AveWinchester, MA 01890
Cheap Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA from $1,400 (55 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winchester Highlands area of Winchester.
close
View Me
$1,9001 Bedroom Apartments Available Now
2 Elmwood Ave, Unit 22
2 Elmwood AveWinchester, MA 01890
200 Swanton St, Unit #704
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit 310
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit 3, Unit 3
200 Swanton St
WinchesterMA01890
close
View Me
$2,050Studio Apartments Available Now
2 Elmwood Ave, Unit 53
2 Elmwood AveWinchester, MA 01890
close
View Me
$2,095
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,095
Total Monthly Price
$2,095
8 Chapin St, Unit 1, Unit 1
8 Chapin StWinchester, MA 01890
close
View Me
$2,095
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,095
Total Monthly Price
$2,095
8 Chapin St, Unit #1J, Unit #1J
8 Chapin StWinchester, MA 01890
close
View Me
$2,150
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,150
Total Monthly Price
$2,150
6 Holland St, Unit 6R, Unit 6R
6 Holland StWinchester, MA 01890
6 Holland St
WinchesterMA01890
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
close
View Me
$2,495
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,495
Total Monthly Price
$2,495
19 Irving St, Unit 3, Unit 3
19 Irving StWinchester, MA 01890
close
View Me
$2,495
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,495
Total Monthly Price
$2,495
19 Irving St, Unit #3-J, Unit #3-J
19 Irving StWinchester, MA 01890
200 Swanton St, Unit #303, Unit #303
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit 704, Unit 704
200 Swanton St
WinchesterMA01890
200 Swanton St
WinchesterMA01890
close
View Me
$1,7001 Bedroom Apartments Available May 15
532 Main St, Unit L
532 Main StWoburn, MA 01801
close
View Me
$1,750 - $2,400
Total Monthly Price12 Month Lease Term
Studio to 2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,750 - $2,400
Total Monthly Price
$1,750 - $2,400
48 Nashua St
48 Nashua StWoburn, MA 01801
close
View Me
$1,780Studio Apartments Available Now
182 Central St, Unit 1
182 Central StStoneham, MA 02180
48 Warren Ave
WoburnMA01801
close
View Me
Rent Specials
$1,950 - $2,600
Plus Fees12 Month Lease Term
1 to 2 Bedroom Apartments Available NowMill Street Gardens
57 Mill StWoburn, MA 01801
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
1 Continental Ct
WoburnMA01801
74 Beach St, Unit Continental Court, Unit Continental Court
74 Beach St
WoburnMA01801
close
View Me
$2,050
Plus Fees1 Month Lease Term
Studio Apartments Available Now2-15 Winn Park
2-15 Winn ParkWoburn, MA 01801
close
View Me
$2,050 - $3,075
Plus Fees12 Month Lease Term
1 to 2 Bedroom Apartments Contact Us For AvailabilityMill Street Heights
59 Mill StWoburn, MA 01801
close
View Me
Rent Specials
$2,141 - $5,251
Total Monthly Price
Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,141 - $5,251
Total Monthly Price
Varies
Hanover Stoneham
95 Maple StStoneham, MA 02180
close
View Me
$2,195
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available May 15Total Monthly Price
Base Rent
$2,195
Total Monthly Price
$2,195
103 Pleasant St, Unit 1, Unit 1
103 Pleasant StWoburn, MA 01801
80 N Warren St
WoburnMA01801
close
View Me
$2,250
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,250
Total Monthly Price
$2,250
25 Arlington Rd, Unit Apt 1-1, Unit Apt 1-1
25 Arlington RdWoburn, MA 01801
39 Montvale Ave
WoburnMA01801
157 Franklin St, Unit 11, Unit 11
157 Franklin St
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.
close
View Me
$2,300 - $2,350
Plus Fees
1 Bedroom Apartments Available Now7 Kilby St
7 Kilby StWoburn, MA 01801
close
View Me
$2,3451 Bedroom Apartments Available Now
68 Mill St, Unit 8
68 Mill StWoburn, MA 01801
close
View Me
$2,350
Plus Fees
2 Bedroom Apartments Available Jul 130 Pomeworth Street
30 Pomeworth StStoneham, MA 02180
close
View Me
$2,380 - $2,800
Plus Fees1 Month Lease Term
Studio to 1 Bedroom Apartments Available Now44 Montvale Avenue
44 Montvale AveWoburn, MA 01801
99 Montvale Ave
WoburnMA01801
close
View Me
Rent Specials
$2,449 - $5,022
Total Monthly Price
Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,449 - $5,022
Total Monthly Price
Varies
The Devon at Weiss Farm
168 Franklin StStoneham, MA 02180
close
View Me
$2,4502 Bedroom Apartments Available Jul 1
50 Mill St, Unit 11
50 Mill StWoburn, MA 01801
close
View Me
$2,4502 Bedroom Apartments Available Jun 1
21 Plympton St
21 Plympton StWoburn, MA 01801
close
View Me
$2,4502 Bedroom Apartments Available Now
82 Mill St, Unit 12
82 Mill StWoburn, MA 01801
close
View Me
$2,4951 Bedroom Apartments Available Now
286 Main St, Unit 209
286 Main StWoburn, MA 01801
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
286 Main St, Unit 209
286 Main St
WoburnMA01801
close
View Me
$2,500
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Jul 1Total Monthly Price
Base Rent
$2,500
Total Monthly Price
$2,500
14 Salem St, Unit 3, Unit 3
14 Salem StWoburn, MA 01801
289 Elm St, Unit 14, Unit 14
289 Elm St
MedfordMA02155
close
View Me
1 Bedroom Apartments
667 Main St
667 Main StWoburn, MA 01801
close
View Me
Studio to 2 Bedroom Apartments
Stoneham House
180-222 Central StStoneham, MA 02180
close
View Me
1 to 2 Bedroom Apartments
411 Main St
411 Main StStoneham, MA 02180
close
View Me
1 Bedroom Apartments
71-73 Winn St
71-73 Winn StWoburn, MA 01801
35 Prospect St
WoburnMA01801
71 Montvale Ave
StonehamMA02180
25 R Auburn St
WoburnMA01801
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.
Winchester Highlands, Winchester, MA Local Guide
Downtown Winchester, Massachusetts by Moonshine4711 is licensed under CC BY-SA 3.0
How much does it cost to rent an apartment in Winchester Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Highlands Studio Apartments | $2,329 | $1,500 | $2,700 |
| Winchester Highlands 1 Bedroom Apartments | $2,920 | $1,700 | $4,365 |
| Winchester Highlands 2 Bedroom Apartments | $3,519 | $2,250 | $5,440 |
| Winchester Highlands 3 Bedroom Apartments | $4,484 | $3,500 | $5,573 |
| Winchester Highlands 4 Bedroom Apartments | $3,650 | $3,100 | $4,150 |
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 55 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
Cheapest Available Winchester Highlands Apartments for Rent
The cheapest available apartment rental in the Winchester Highlands area of Boston, MA is a 1 Bed unit found at Mill Street Gardens priced from $1,950. 2-15 Winn Park has the second lowest priced unit, which is a Studio apartment currently listed from $2,050. Here are the most affordable Winchester Highlands apartments for rent in Boston, MA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $1,950 |
| 2-15 Winn Park | Studio | Studio,1BA | $2,050 |
| 7 Kilby St | 1 Bedroom | 1BR,1BA | $2,300 |
| 44 Montvale Avenue | Studio | Studio,1BA | $2,380 |
Best Value Apartments for Rent in Winchester Highlands, MA
As of May 08, 2026 the best value apartment in the Winchester Highlands area is the $2.11 price per square foot 10 Webster St Model at 10 Webster St, Unit 1 in the in the North Medford neighborhood starting from $4,150. The second greatest value Winchester Highlands apartment is the 68 Pleasant St Model at 68 Pleasant St, Unit #1 starting at $2,700 with a $2.08 price per square foot in the Wyoming neighborhood. Here is today’s list of the best values for Winchester Highlands apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 10 Webster St, Unit 1 | 10 Webster St | 4BR,2BA | $2.11 |
| 68 Pleasant St, Unit #1 | 68 Pleasant St | 2BR,1BA | $2.08 |
| 286 Main St, Unit 3 | 286 Main St | 2BR,2BA | $2.36 |
| 16 Kilby St, Unit 3 | 16 Kilby St | 4BR,1BA | $2.58 |
| 8 Eastern Ave, Unit 1st floor | 8 Eastern Ave | 2BR,1BA | $2.36 |
| 19 Irving St, Unit 3 | 19 Irving St | 2BR,1BA | $2.50 |
| 159 Main St | 159 Main St | 2BR,2BA | $2.67 |
| 25 Arlington Rd, Unit Apt 1-1 | 25 Arlington Rd | 2BR,1BA | $2.64 |
| Mill Street Gardens | 2 Bedroom | 2BR,1BA | $2.65 |
| 8 Chapin St, Unit 1 | 8 Chapin St | 1BR,1BA | $2.46 |
Frequently Asked Questions about Cheap Winchester Highlands Apartments
What is the Cheapest Studio apartment in Winchester Highlands?
Currently the most affordable Cheap Studio Apartment in Winchester Highlands is at 2-15 Winn Park listed at $2,050.
How much is rent for a Cheap One Bedroom Winchester Highlands Apartment?
The lowest price for a Cheap One Bedroom Winchester Highlands Apartment is $1,950 at Mill Street Gardens.
What is the lowest price for a Cheap Two Bedroom Winchester Highlands Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winchester Highlands is starting from $2,250 at Mill Street Gardens.
What is the most affordable Winchester Highlands Three Bedroom Apartment?
The best deal on a cheap Winchester Highlands Three Bedroom Apartment rental is at Hanover Stoneham and starts from $4,316.
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
Written by: Amelia Ramstead
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
Written by: Amelia Ramstead
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
Written by: Amelia Ramstead
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
A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.
Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.