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$1,6951 Bedroom Apartments Available Now
40 Warren Ave
40 Warren AveWoburn, MA 01801
Cheap Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA from $1,800 (20 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester Highlands area of Winchester.
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$1,780Studio Apartments Available Now
182 Central St
182 Central StStoneham, MA 02180
35 Prospect St
WoburnMA01801
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit T7
200 Swanton St
WinchesterMA01890
14 Church Ave
WoburnMA01801
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.
14 Church Ave
WoburnMA01801
14 Church Ave, Unit 2A
14 Church Ave
WoburnMA01801
890 Highland Ave
MedfordMA02155
200 Park Terrace Dr, Unit 222
200 Park Terrace Dr
StonehamMA02180
71 Montvale Ave
StonehamMA02180
200 Swanton St
WinchesterMA01890
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.
74 Beach St
WoburnMA01801
177 Central St
StonehamMA02180
12 Davis St
WoburnMA01801
27 Arlington Rd, Unit 5
27 Arlington Rd
WoburnMA01801
56 Warren Ave
WoburnMA01801
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.
100 Ledgewood Dr, Unit 515
100 Ledgewood Dr
StonehamMA02180
4 Quigley Ct
WinchesterMA01890
Showing Results 1-20, 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 | $2,841 | $2,075 | $5,350 |
| Winchester Highlands 3 Bedroom Homes for Rent | $3,327 | $2,500 | $4,200 |
| Winchester Highlands 4 Bedroom Homes for Rent | $4,735 | $3,990 | $5,300 |
| Winchester Highlands 5 Bedroom Homes for Rent | $5,265 | $2,800 | $7,000 |
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 20 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 2 Beds unit found at Mill Street Gardens priced from $2,250. 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 | 2 Bedroom | 2BR,1BA | $2,250 |
| Mill Street Heights | B | 1BR,1BA | $2,275 |
| The Devon at Weiss Farm | Studio | Studio,1BA | $2,277 |
| 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 31, 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 |
| 4 Quigley Ct, Unit 4 | 4 Quigley Ct | 3BR,1.5BA | $2.08 |
| 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 |
| Mill Street Gardens | 2 Bedroom | 2BR,1BA | $2.65 |
| 37 Arlington St, Unit 1 | 37 Arlington St | 1BR,1BA | $2.23 |
| 74 Beach St, Unit #3-3 | 74 Beach St | 2BR,1BA | $2.87 |
Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 122 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,695 to $5,200. There are also 59 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,850 to $7,000.
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 $1,850 to $7,000 with an average monthly rent of $3,349.
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 $2,500 to $5,149, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $4,200. Four Bedroom Single-Family rentals are also available starting from $3,990 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.
Helpful Local Expert Guides
The 10 Best Affordable Neighborhoods in Boston, MA
Written by: Amelia Ramstead
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.
A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!
Explore Like a Local: The Insider's Guide to Boston
Written by: Amelia Ramstead
Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
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Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips
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.
Apartment Common Area Rules: What Renters Need to Know
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.