close
View Me
1 Bedroom Apartments
Elmwood Apartments
2 Elmwood AveWinchester, MA 01890
Cheap Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA from $1,450 (31 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winchester Highlands area of Winchester.
200 Swanton St, Unit 240
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit 708
200 Swanton St
WinchesterMA01890
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit 313
200 Swanton St
WinchesterMA01890
close
View Me
$1,750
Total Monthly Price
Base Rent$1,750
Total Monthly Price$1,750
37 Arlington St, Unit 2F
37 Arlington StWoburn, MA 01801
close
View Me
$1,795
Total Monthly Price
Base Rent$1,795
Total Monthly Price$1,795
103 Pleasant St, Unit 2
103 Pleasant StWoburn, MA 01801
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
close
View Me
$1,850
Total Monthly Price
Base Rent$1,850
Total Monthly Price$1,850
224 Main St, Unit 2
224 Main StWoburn, MA 01801
close
View Me
Rent Specials
$1,950 - $2,600
Total Monthly Price
Base Rent$1,950 - $2,600
Total Monthly Price$1,950 - $2,600
Mill Street Gardens
57 Mill StWoburn, MA 01801
close
View Me
$1,950 - $2,375
Total Monthly Price
Base Rent$1,950 - $2,375
Total Monthly Price$1,950 - $2,375
2-15 Winn Park
2-15 Winn ParkWoburn, MA 01801
close
View Me
$1,995
Total Monthly Price
Base Rent$1,995
Total Monthly Price$1,995
23 Summer St, Unit B
23 Summer StWoburn, MA 01801
close
View Me
$1,995
Total Monthly Price
Base Rent$1,995
Total Monthly Price$1,995
628 Main St, Unit 4
628 Main StWoburn, MA 01801
35 Prospect St, Unit 311
35 Prospect St
WoburnMA01801
close
View Me
$2,000
Total Monthly Price
Base Rent$2,000
Total Monthly Price$2,000
43 Mc Cormack St, Unit 1
43 Mc Cormack StMalden, MA 02148
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
close
View Me
$2,100
Total Monthly Price
Base Rent$2,100
Total Monthly Price$2,100
48 Garfield Ave, Unit Woburn Apartment
48 Garfield AveWoburn, MA 01801
close
View Me
$2,2001 Bedroom Apartments Available Now
78 Mill St, Unit 10
78 Mill StWoburn, MA 01801
close
View Me
$2,2001 Bedroom Apartments Available Nov 1
70 Mill St, Unit 6
70 Mill StWoburn, MA 01801
close
View Me
$2,3001 Bedroom Apartments Available Now
70 Mill St, Unit 10
70 Mill StWoburn, MA 01801
close
View Me
$2,300 - $2,350
Total Monthly Price
Base Rent$2,300 - $2,350
Total Monthly Price$2,300 - $2,350
7-1 Kilby St
7 Kilby StWoburn, MA 01801
close
View Me
$2,3001 Bedroom Apartments Available Oct 1
70 Mill St, Unit 2
70 Mill StWoburn, MA 01801
13 Center St
WoburnMA01801
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
1 Bedroom Apartments
667 Main St
667 Main StWoburn, MA 01801
close
View Me
1 to 2 Bedroom Apartments
411 Main St
411 Main StStoneham, MA 02180
74 Beach St, Unit 5-1
74 Beach St
WoburnMA01801
74 Beach St
WoburnMA01801
close
View Me
1 Bedroom Apartments
71-73 Winn St
71-73 Winn StWoburn, MA 01801
84 Franklin St, Unit 2
84 Franklin St
StonehamMA02180
close
View Me
Studio to 2 Bedroom Apartments
Stoneham House
180-222 Central StStoneham, MA 02180
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.
33 Montvale Ave
WoburnMA01801
39 Montvale Ave
WoburnMA01801
305 Salem St
WoburnMA01801
Showing Results 1-31, Page 1 of 1
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 | $2,506 | $1,950 | $2,964 |
| Winchester Highlands 1 Bedroom Apartments | $2,947 | $1,750 | $4,070 |
| Winchester Highlands 2 Bedroom Apartments | $3,559 | $2,375 | $5,354 |
| Winchester Highlands 3 Bedroom Apartments | $4,890 | $3,200 | $7,312 |
| Winchester Highlands 4 Bedroom Apartments | $3,900 | $3,700 | $4,100 |
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 31 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 Elmwood Apartments priced from $1,900. Mill Street Gardens has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,950. Here are the most affordable Winchester Highlands apartments for rent in Boston, MA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Elmwood Apartments | Studio 265sf | 1BR, 1BA | $1,900 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR, 1BA | $1,950 |
| 2-15 Winn Park | Studio | Studio, 1BA | $1,950 |
| 7-1 Kilby St | 1 Bedroom | 1BR, 1BA | $2,300 |
| 30 Pomeworth Street | 2BR/1.0BA | 2BR, 1BA | $2,395 |
Best Value Apartments for Rent in Winchester Highlands, MA
As of September 22, 2026 the best value apartment in the Winchester Highlands area is the $1.93 price per square foot 2BR/2.5BA Model at Pomeworth Corner in the Nobility Hill neighborhood starting from $3,295. The second greatest value Winchester Highlands apartment is the 286 Main St Model at 286 Main St, Unit 3 in the Walnut Hill neighborhood starting at $2,995 with a $2.36 price per square foot. 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. |
|---|---|---|---|
| Pomeworth Corner | 2BR/2.5BA | 2BR, 2.5BA | $1.93 |
| 286 Main St, Unit 3 | 286 Main St | 2BR, 2BA | $2.36 |
| 48 Nashua St, Unit 2 | 48 Nashua St | 2BR, 1BA | $2.16 |
| 48 Pleasant Street | 2BR/1.5BA | 2BR, 1.5BA | $2.92 |
| 32 Pond St, Unit 2 | 32 Pond St | 2BR, 1BA | $2.40 |
| 25 Arlington Rd, Unit Apt #3 6 | 25 Arlington Rd | 2BR, 1BA | $2.86 |
| Mill Street Gardens | 2 Bedroom | 2BR, 1BA | $2.65 |
| 103 Pleasant St, Unit 2 | 103 Pleasant St | 1BR, 1BA | $2.24 |
| 43 Mc Cormack St, Unit 1 | 43 Mc Cormack St | Studio, 1BA | $2.67 |
| 628 Main St, Unit 4 | 628 Main St | 1BR, 1BA | $2.77 |
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 $1,950.
How much is rent for a Cheap One Bedroom Winchester Highlands Apartment?
The lowest price for a Cheap One Bedroom Winchester Highlands Apartment is $1,900 at Elmwood Apartments.
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 Sanctuary Winchester North and starts from $4,883.
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
Rent According to Income: A Look at Income-Restricted Rentals
Written by: Robin Stewart
The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.
How Commercial-to-Residential Property Conversions Help the Housing Crisis
Written by: Robin Stewart
Many housing markets throughout America share a common complaint: a lack of affordable rental properties.
Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.