0 Green St
WoburnMA01801
Cheap Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA from $1,100 (14 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester Highlands area of Winchester.
48 Warren Ave
WoburnMA01801
200 Swanton St
WinchesterMA01890
50 Franklin St
StonehamMA02180
71 Montvale Ave
StonehamMA02180
200 Swanton St
WinchesterMA01890
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71 Montvale Ave
StonehamMA02180
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200 Swanton St
WinchesterMA01890
200 Swanton St
WinchesterMA01890
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177 Central St
StonehamMA02180
31 Montvale Ave
WoburnMA01801
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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 a home in Winchester Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Highlands 2 Bedroom Homes for Rent | $2,978 | $2,075 | $5,700 |
| Winchester Highlands 3 Bedroom Homes for Rent | $3,556 | $2,850 | $4,500 |
| Winchester Highlands 4 Bedroom Homes for Rent | $5,151 | $3,800 | $8,000 |
| Winchester Highlands 5 Bedroom Homes for Rent | $6,247 | $5,295 | $7,500 |
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 14 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
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Winchester Highlands, Winchester, MA Local Guide
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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. The Devon at Weiss Farm has the second lowest priced unit, which is a Studio apartment currently listed from $2,247. 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 |
| The Devon at Weiss Farm | Studio | Studio,1BA | $2,247 |
| 44 Montvale Avenue | Studio | Studio,1BA | $2,380 |
| Sanctuary Winchester North | 1A | 1BR,1BA | $2,419 |
| Hanover Stoneham | Ga | 1BR,1BA | $2,431 |
Best Value Apartments for Rent in Winchester Highlands, MA
As of October 27, 2025 the best value apartment in the Winchester Highlands area is the $0.30 price per square foot 8 Cross St Model at 8 Cross St, Unit 1 in the in the Walnut Hill neighborhood starting from $2,980. The second greatest value Winchester Highlands apartment is the 11 Garfield Ave Model at 11 Garfield Ave, Unit 1 starting at $4,400 with a $2.20 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. |
|---|---|---|---|
| 8 Cross St, Unit 1 | 8 Cross St | 3BR,1.5BA | $0.30 |
| 11 Garfield Ave, Unit 1 | 11 Garfield Ave | 4BR,3BA | $2.20 |
| 286 Main St, Unit 3 | 286 Main St | 2BR,2BA | $2.36 |
| 48 Pleasant Street | 2BR/1.5BA | 2BR,1.5BA | $2.87 |
| 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 | 1 Bedroom, 1 Bath | 1BR,1BA | $2.44 |
| 7 Court St, Unit 1 | 7 Court St | 1BR,1BA | $2.37 |
| 74 Beach St, Unit #3-3 | 74 Beach St | 2BR,1BA | $2.87 |
| 8 Eastern Ave, Unit Thirdfloor | 8 Eastern Ave | 1BR,1BA | $2.79 |
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Pet Friendly LifestyleWinchester Highlands, Winchester, MA
Ranked #2
Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.0Pet Friendly
Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 111 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,550 to $6,900. There are also 62 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,100 to $8,000.
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 $1,100 to $8,000 with an average monthly rent of $3,956.
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 $2,800 to $6,900, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,850 to $4,500. Four Bedroom Single-Family rentals are also available starting from $3,800 and Four Bedroom Apartments start at $4,400.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.
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.
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.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.