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$1,800
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
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$1,800
Total Monthly Price
$1,800
200 Swanton St, Unit T36
200 Swanton StWinchester, MA 01890
Cheap Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA from $1,400 (17 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winchester Highlands area of Winchester.
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$1,800
Total Monthly Price12 Month Lease Term
Studio Apartment Available Jun 1Total Monthly Price
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$1,800
Total Monthly Price
$1,800
219 Washington St, Unit 3
219 Washington StWinchester, MA 01890
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1 Bedroom Apartments
Elmwood Apartments
2 Elmwood AveWinchester, MA 01890
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$1,700 - $3,000
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Studio to 2 Bedroom Apartments Available NowTotal Monthly Price
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$1,700 - $3,000
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$1,700 - $3,000
79 Montvale Ave
79 Montvale AveWoburn, MA 01801
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$1,750 - $2,400
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Studio to 2 Bedroom Apartment Available NowTotal Monthly Price
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$1,750 - $2,400
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$1,750 - $2,400
48 Nashua St
48 Nashua 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.
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$1,780Studio Apartments Available Now
182 Central St
182 Central StStoneham, MA 02180
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$1,795 - $1,950
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
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$1,795 - $1,950
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$1,795 - $1,950
7 Court St
7 Court StWoburn, MA 01801
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$1,900Studio Apartments Available Apr 1
50 Mill St
50 Mill StWoburn, MA 01801
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$1,950 - $2,600
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1 to 2 Bedroom Apartments Available NowTotal Monthly Price
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$1,950 - $2,600
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$1,950 - $2,600
Mill Street Gardens
57 Mill StWoburn, MA 01801
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$1,950
Total Monthly Price1 Month Lease Term
Studio Apartments Available NowTotal Monthly Price
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$1,950
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$1,950
2-15 Winn Park
2-15 Winn ParkWoburn, 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.
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$2,1951 Bedroom Apartments Available Apr 1
68 Mill St
68 Mill StWoburn, MA 01801
15 Church Ave
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
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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1 Bedroom Apartments
71-73 Winn St
71-73 Winn StWoburn, MA 01801
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Studio to 1 Bedroom Apartments
30 Pomeworth Street
30 Pomeworth StStoneham, MA 02180
Showing Results 1-17, Page 1 of 1
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 | $2,285 | $1,700 | $2,733 |
| Winchester Highlands 1 Bedroom Apartments | $3,013 | $1,795 | $4,304 |
| Winchester Highlands 2 Bedroom Apartments | $3,455 | $2,250 | $5,150 |
| Winchester Highlands 3 Bedroom Apartments | $4,386 | $2,300 | $5,761 |
| Winchester Highlands 4 Bedroom Apartments | $4,675 | $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 17 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 Elmwood Apartments priced from $1,500. 79 Montvale Ave has the second lowest priced unit, which is a Studio apartment currently listed from $1,700. Here are the most affordable Winchester Highlands apartments for rent in Boston, MA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Elmwood Apartments | Studio 250 sf | 1BR,1BA | $1,500 |
| 79 Montvale Ave | Studio | Studio,1BA | $1,700 |
| 2-15 Winn Park | Studio | Studio,1BA | $1,950 |
| The Devon at Weiss Farm | Studio | Studio,1BA | $2,343 |
| 44 Montvale Avenue | Studio | Studio,1BA | $2,380 |
Best Value Apartments for Rent in Winchester Highlands, MA
As of March 23, 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 286 Main St Model at 286 Main St, Unit 3 starting at $2,995 with a $2.36 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. |
|---|---|---|---|
| 10 Webster St, Unit 1 | 10 Webster St | 4BR,2BA | $2.11 |
| 286 Main St, Unit 3 | 286 Main St | 2BR,2BA | $2.36 |
| 107 Belle Ave | 107 Belle Ave | 3BR,1BA | $3.13 |
| 8 Eastern Ave, Unit 1st floor | 8 Eastern Ave | 2BR,1BA | $2.36 |
| 12 Montvale Ave | 2 Bedroom | 2BR,2BA | $2.64 |
| Mill Street Heights | C | 2BR,2BA | $2.77 |
| 17 Linden St, Unit 17 Linden St | 17 Linden St | 2BR,1.5BA | $2.90 |
| 48 Nashua St | 48 Nashua St | 2BR,1BA | $2.45 |
| 159 Main St | 159 Main St | 2BR,2BA | $2.67 |
| 25 Arlington Rd, Unit Apt 1-1 | 25 Arlington Rd | 2BR,1BA | $2.64 |
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 79 Montvale Ave listed at $1,700.
How much is rent for a Cheap One Bedroom Winchester Highlands Apartment?
The lowest price for a Cheap One Bedroom Winchester Highlands Apartment is $1,500 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 $2,650 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 The Devon at Weiss Farm and starts from $4,413.
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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The 10 Best Affordable Neighborhoods in Boston, MA
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Explore Like a Local: The Insider's Guide to Boston
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Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
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Articles, How-To's, and Tips
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.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.
Renting with Roommates: Realistic Expectations for Shared Lease
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.