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$1,500Studio Apartments Available Now
2 Elmwood Ave, Unit 13
2 Elmwood AveWinchester, MA 01890
Cheap Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA from $1,800 (29 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester Highlands area of Winchester.
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$1,7001 Bedroom Apartments Available May 15
532 Main St, Unit L
532 Main StWoburn, MA 01801
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$1,780Studio Apartments Available Now
182 Central St, Unit 1
182 Central StStoneham, MA 02180
200 Swanton St, Unit 704, Unit 704
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit #704
200 Swanton St
WinchesterMA01890
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$1,9001 Bedroom Apartments Available Now
2 Elmwood Ave, Unit 22
2 Elmwood AveWinchester, MA 01890
35 Prospect St
WoburnMA01801
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.
71 Montvale Ave
StonehamMA02180
200 Swanton St, Unit 3, Unit 3
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit 310
200 Swanton St
WinchesterMA01890
1 Continental Ct
WoburnMA01801
74 Beach St, Unit Continental Court, Unit Continental Court
74 Beach St
WoburnMA01801
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$2,050Studio Apartments Available Now
2 Elmwood Ave, Unit 53
2 Elmwood AveWinchester, MA 01890
200 Swanton St
WinchesterMA01890
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.
25 R Auburn St
WoburnMA01801
157 Franklin St, Unit 11, Unit 11
157 Franklin St
StonehamMA02180
20-22-22 Emerson St
StonehamMA02180
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$2,3451 Bedroom Apartments Available Now
68 Mill St, Unit 8
68 Mill StWoburn, MA 01801
74 Beach St
WoburnMA01801
177 Franklin St, Unit 2, Unit 2
177 Franklin St
StonehamMA02180
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$2,4502 Bedroom Apartments Available Jul 1
50 Mill St, Unit 11
50 Mill StWoburn, MA 01801
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.
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$2,4502 Bedroom Apartments Available Jun 1
21 Plympton St
21 Plympton StWoburn, MA 01801
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$2,4502 Bedroom Apartments Available Now
82 Mill St, Unit 12
82 Mill StWoburn, MA 01801
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$2,4951 Bedroom Apartments Available Now
286 Main St, Unit 209
286 Main StWoburn, MA 01801
286 Main St, Unit 209
286 Main St
WoburnMA01801
286 Main St
WoburnMA01801
289 Elm St, Unit 14, Unit 14
289 Elm St
MedfordMA02155
39 Franklin St
WoburnMA01801
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.
200 Swanton St, Unit #303, Unit #303
200 Swanton St
WinchesterMA01890
Showing Results 1-29, 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 a home in Winchester Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Highlands 2 Bedroom Homes for Rent | $2,794 | $2,300 | $4,500 |
| Winchester Highlands 3 Bedroom Homes for Rent | $4,240 | $2,500 | $8,000 |
| Winchester Highlands 4 Bedroom Homes for Rent | $4,578 | $3,100 | $7,900 |
| Winchester Highlands 5 Bedroom Homes for Rent | $15,497 | $5,995 | $10,000+ |
| Winchester Highlands 6 Bedroom Homes for Rent | $5,497 | $5,497 | $5,497 |
| Winchester Highlands 7 Bedroom Homes for Rent | $12,000 | $10,000 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 29 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 |
| 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 Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 125 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,500 to $12,505. There are also 62 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,890 to $25,000.
What is the current price range for Rental Homes in Winchester Highlands?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester Highlands ranges from $1,890 to $25,000 with an average monthly rent of $6,099.
How much are larger Three and Four Bedroom Rentals in Winchester Highlands?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester Highlands range from $3,500 to $5,573, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $8,000. Four Bedroom Single-Family rentals are also available starting from $3,100 and Four Bedroom Apartments start at $3,100.
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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Maximizing Your Refund: Essential Tax Tips for Renters
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