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$1,780Studio Apartments Available Now
182 Central St
182 Central StStoneham, MA 02180
Cheap Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA from $1,800 (15 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester Highlands area of Winchester.
200 Swanton St
WinchesterMA01890
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$1,900Studio Apartments Available Apr 1
50 Mill St
50 Mill StWoburn, MA 01801
159 Franklin St
StonehamMA02180
71 Montvale Ave
StonehamMA02180
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.
150 Main St
StonehamMA02180
200 Swanton St, Unit 3
200 Swanton St
WinchesterMA01890
200 Swanton St
WinchesterMA01890
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$2,1951 Bedroom Apartments Available Apr 1
68 Mill St
68 Mill StWoburn, MA 01801
74 Beach 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.
157 Franklin St, Unit A11
157 Franklin St
StonehamMA02180
80 N Warren St
WoburnMA01801
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$2,4502 Bedroom Apartments Available Jul 1
50 Mill St
50 Mill StWoburn, MA 01801
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$2,4502 Bedroom Apartments Available Now
82 Mill St
82 Mill StWoburn, MA 01801
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
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.
Showing Results 1-15, 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 | $3,107 | $2,300 | $5,350 |
| Winchester Highlands 3 Bedroom Homes for Rent | $4,400 | $2,600 | $8,000 |
| Winchester Highlands 4 Bedroom Homes for Rent | $4,829 | $3,650 | $6,995 |
| Winchester Highlands 5 Bedroom Homes for Rent | $15,497 | $5,995 | $10,000+ |
| Winchester Highlands 6 Bedroom Homes for Rent | $9,500 | $9,500 | $9,500 |
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 15 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 24, 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 Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 118 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,700 to $18,945. There are also 44 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,800 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 $1,800 to $25,000 with an average monthly rent of $5,871.
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 $2,300 to $5,761, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $8,000. Four Bedroom Single-Family rentals are also available starting from $3,650 and Four Bedroom Apartments start at $4,150.
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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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
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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.