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$2,0501 Bedroom Apartments Available Now
2 Elmwood Ave, Unit 1
2 Elmwood AveWinchester, MA 01890
Cheap Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA from $1,400 (33 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winchester Highlands area of Winchester.
200 Swanton St, Unit 228
200 Swanton St
WinchesterMA01890
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit 412
200 Swanton St
WinchesterMA01890
8 Mason St
WinchesterMA01890
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$1,695
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,695
Total Monthly Price
$1,695
58 Campbell St, Unit 2
58 Campbell StWoburn, MA 01801
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$1,695
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,695
Total Monthly Price
$1,695
58 Campbell St, Unit 2
58 Campbell StWoburn, MA 01801
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$1,695
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,695
Total Monthly Price
$1,695
58 Campbell St, Unit 2
58 Campbell 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
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$1,795
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,795
Total Monthly Price
$1,795
7 Mishawum Rd, Unit B
7 Mishawum RdWoburn, MA 01801
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$1,895
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,895
Total Monthly Price
$1,895
103 Pleasant St, Unit 2l
103 Pleasant StWoburn, MA 01801
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$1,895
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,895
Total Monthly Price
$1,895
103 Pleasant St, Unit 2
103 Pleasant StWoburn, MA 01801
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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
39 Montvale Ave
WoburnMA01801
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$2,050
Plus Fees1 Month Lease Term
Studio Apartments Available Now2-15 Winn Park
2-15 Winn ParkWoburn, MA 01801
80 N Warren St
WoburnMA01801
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$2,100
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
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$2,100
Total Monthly Price
$2,100
157 Franklin St, Unit #B2
157 Franklin StStoneham, MA 02180
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.
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Rent Specials
$2,256 - $5,628
Total Monthly Price
Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,256 - $5,628
Total Monthly Price
Varies
Hanover Stoneham
95 Maple StStoneham, MA 02180
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$2,300 - $2,350
Plus Fees12 Month Lease Term
1 Bedroom Apartments Available Now7-1 Kilby St
7 Kilby StWoburn, MA 01801
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Rent Specials
$2,400 - $3,075
Plus Fees12 Month Lease Term
2 Bedroom Apartments Contact Us For AvailabilityMill Street Heights
59 Mill StWoburn, MA 01801
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$2,400 - $2,600
Plus Fees
1 Bedroom Apartments Available Now79 Montvale Ave
79 Montvale AveWoburn, MA 01801
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1 Bedroom Apartments
667 Main St
667 Main StWoburn, MA 01801
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1 to 2 Bedroom Apartments
411 Main St
411 Main StStoneham, MA 02180
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1 Bedroom Apartments
71-73 Winn St
71-73 Winn StWoburn, MA 01801
84 Franklin St, Unit 2
84 Franklin St
StonehamMA02180
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.
35 Prospect St
WoburnMA01801
74 Beach St, Unit 5-1
74 Beach St
WoburnMA01801
74 Beach St
WoburnMA01801
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Studio to 2 Bedroom Apartments
Stoneham House
180-222 Central StStoneham, MA 02180
426 Main St
StonehamMA02180
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1 to 2 Bedroom Apartments
30 Pomeworth Street
30 Pomeworth StStoneham, MA 02180
22 Emerson St
StonehamMA02180
35 Arlington St
WoburnMA01801
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.
182 Central St
StonehamMA02180
Showing Results 1-33, 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 | $2,510 | $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.
Browse Apartments in this Neighborhood
There are currently 33 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
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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 |
| 30 Pomeworth Street | 2BR/1.0BA | 2BR,1BA | $2,295 |
Best Value Apartments for Rent in Winchester Highlands, MA
As of August 07, 2026 the best value apartment in the Winchester Highlands area is the $2.31 price per square foot 722 Highland Ave Model at 722 Highland Ave, Unit 2 in the in the Ferryway neighborhood starting from $3,000. The second greatest value Winchester Highlands apartment is the 14 Salem St Model at 14 Salem St starting at $2,600 with a $2.26 price per square foot in the Walnut Hill 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. |
|---|---|---|---|
| 722 Highland Ave, Unit 2 | 722 Highland Ave | 3BR,2BA | $2.31 |
| 14 Salem St | 14 Salem St | 2BR,1BA | $2.26 |
| 48 Nashua St, Unit 2 | 48 Nashua St | 2BR,1BA | $2.27 |
| 32 Pond St, Unit 2w | 32 Pond St | 2BR,1BA | $2.45 |
| 32 Pond St, Unit 2 | 32 Pond St | 2BR,1BA | $2.45 |
| 79 Montvale Ave | 1 Bedroom | 1BR,1BA | $2.40 |
| Mill Street Gardens | 2 Bedroom | 2BR,1BA | $2.65 |
| 103 Pleasant St, Unit 2 | 103 Pleasant St | 1BR,1BA | $2.37 |
| 7 Mishawum Rd, Unit Unit B | 7 Mishawum Rd | 1BR,1BA | $2.39 |
| 103 Pleasant St, Unit 2l | 103 Pleasant St | 1BR,1BA | $2.53 |
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 Sanctuary Winchester North and starts from $5,465.
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.
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