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$1,850
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Studio Apartments Available Now2 Elmwood Ave
2 Elmwood AveWinchester, MA 01890
Cheap Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA from $1,400 (21 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winchester Highlands area of Winchester.
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$1,850
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
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$1,850
Total Monthly Price
$1,850
200 Swanton St, Unit T36
200 Swanton StWinchester, MA 01890
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$1,950
Plus Fees
1 Bedroom Apartments Available Now2 Elmwood Ave
2 Elmwood AveWinchester, MA 01890
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$1,950
Plus Fees
1 Bedroom Apartments Available Now2 Elmwood Ave
2 Elmwood AveWinchester, MA 01890
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$1,780
Plus Fees
Studio Apartments Available Now182 Central St
182 Central StStoneham, MA 02180
29 Arlington Rd
WoburnMA01801
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$1,895
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
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$1,895
Total Monthly Price
$1,895
37 Arlington St, Unit 1
37 Arlington StWoburn, MA 01801
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
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$1,950 - $2,150
Plus Fees12 Month Lease Term
1 Bedroom Apartments Available NowMill Street Gardens
57 Mill StWoburn, MA 01801
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$1,950
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available May 1Total Monthly Price
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$1,950
Total Monthly Price
$1,950
224 Main St, Unit 1B
224 Main StWoburn, MA 01801
27 Salem St
WoburnMA01801
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$1,995
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Feb 1Total Monthly Price
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$1,995
Total Monthly Price
$1,995
7 Court St, Unit 1 - J
7 Court StWoburn, MA 01801
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$1,995
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Feb 1Total Monthly Price
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$1,995
Total Monthly Price
$1,995
7 Court St, Unit 1
7 Court StWoburn, MA 01801
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$2,000
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Mar 1Total Monthly Price
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$2,000
Total Monthly Price
$2,000
51 Hancock St
51 Hancock StStoneham, MA 02180
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$2,050
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1 Bedroom Apartments Available Now52 Mill St
52 Mill 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.
284 Montvale Ave
WoburnMA01801
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$2,200
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Feb 1Total Monthly Price
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$2,200
Total Monthly Price
$2,200
32A Highland St, Unit 32A Highland St
32A Highland StWoburn, MA 01801
371 Main St
WoburnMA01801
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1 Bedroom Apartments
667 Main St
667 Main StWoburn, MA 01801
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Studio to 2 Bedroom Apartments
Stoneham House
180-222 Central StStoneham, MA 02180
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1 to 2 Bedroom Apartments
411 Main St
411 Main StStoneham, MA 02180
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Studio to 1 Bedroom Apartments
30 Pomeworth Street
30 Pomeworth StStoneham, MA 02180
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.
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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 | $2,376 | $1,780 | $2,720 |
| Winchester Highlands 1 Bedroom Apartments | $2,753 | $1,850 | $4,195 |
| Winchester Highlands 2 Bedroom Apartments | $3,511 | $2,250 | $4,920 |
| Winchester Highlands 3 Bedroom Apartments | $4,323 | $2,700 | $6,900 |
| Winchester Highlands 4 Bedroom Apartments | $4,500 | $4,150 | $5,200 |
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 21 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. Mill Street Heights has the second lowest priced unit, which is a 1 Bed apartment currently listed from $2,275. 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 |
| Mill Street Heights | B | 1BR,1BA | $2,275 |
| The Devon at Weiss Farm | Studio | Studio,1BA | $2,318 |
| 44 Montvale Avenue | Studio | Studio,1BA | $2,380 |
| Hanover Stoneham | Fa | 1BR,1BA | $2,431 |
Best Value Apartments for Rent in Winchester Highlands, MA
As of January 24, 2026 the best value apartment in the Winchester Highlands area is the $0.30 price per square foot 7 Lowell St Model at 7 Lowell St in the in the Walnut Hill neighborhood starting from $3,000. The second greatest value Winchester Highlands apartment is the 2BR/1.5BA Model at Lofts at 307 Main LLC starting at $2,895 with a $2.07 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. |
|---|---|---|---|
| 7 Lowell St | 7 Lowell St | 2BR,1BA | $0.30 |
| Lofts at 307 Main LLC | 2BR/1.5BA | 2BR,1.5BA | $2.07 |
| 286 Main St, Unit 3 | 286 Main St | 2BR,2BA | $2.36 |
| 48 Pleasant Street | 2BR/1.5BA | 2BR,1.5BA | $2.73 |
| 159 Main St | 159 Main St | 2BR,2BA | $2.67 |
| 15 Landers Rd, Unit B | 15 Landers Rd | Studio ,1BA | $2.50 |
| 25 Arlington Rd, Unit Apt 1-1 | 25 Arlington Rd | 2BR,1BA | $2.64 |
| 37 Arlington St, Unit 1 | 37 Arlington St | 1BR,1BA | $2.23 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $2.44 |
| 74 Beach St, Unit Unit #3-3 | 74 Beach St | 2BR,1BA | $2.87 |
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 The Devon at Weiss Farm listed at $2,318.
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 $2,800 at Mill Street Heights.
What is the most affordable Winchester Highlands Three Bedroom Apartment?
The best deal on a cheap Winchester Highlands Three Bedroom Apartment rental is at Mill Street Heights and starts from $3,450.
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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Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
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Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.