200 Swanton St, Unit 704
200 Swanton St
WinchesterMA01890
Cheap Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA from $1,900 (14 Rentals)
Cheap Homes in the Winchester Highlands area of Winchester.
200 Swanton St, Unit 3
200 Swanton St
WinchesterMA01890
200 Swanton St
WinchesterMA01890
35 Prospect St
WoburnMA01801
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
39 Montvale Ave
WoburnMA01801
60 Franklin St
StonehamMA02180
35 Vine St
WinchesterMA01890
31 Arlington Rd, Unit 5
31 Arlington Rd
WoburnMA01801
Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.
27 Arlington Rd, Unit 5
27 Arlington Rd
WoburnMA01801
100 Ledgewood Dr
StonehamMA02180
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
76 Fowle St
WoburnMA01801
Boston's Best Affordable Neighborhoods
Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead
76 Fowle St
WoburnMA01801
295 W Wyoming Ave, Unit 9C
295 W Wyoming Ave
StonehamMA02180
Showing Results 1-14, 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 Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester Highlands 2 Bedroom Homes for Rent | $3,081 | $2,400 | $4,300 |
| Winchester Highlands 3 Bedroom Homes for Rent | $3,455 | $2,600 | $4,600 |
| Winchester Highlands 4 Bedroom Homes for Rent | $5,048 | $4,450 | $5,300 |
| Winchester Highlands 5 Bedroom Homes for Rent | $5,781 | $5,295 | $7,000 |
| Winchester Highlands 6 Bedroom Homes for Rent | $9,500 | $9,500 | $9,500 |
| Winchester Highlands 7 Bedroom Homes for Rent | $11,000 | $10,000 | $10,000+ |
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.
Explore Winchester
Winchester Highlands, Winchester, MA Local Guide
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Cheapest Available Winchester Highlands Apartments for Rent
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $1,950 |
Best Value Apartments for Rent in Winchester Highlands, MA
As of May 09, 2025 the best value apartment in the Winchester Highlands area is the $0.65 price per square foot 476 Fulton St Model at 476 Fulton St, Unit 1 in the in the Ferryway neighborhood starting from $6,500. The second greatest value Winchester Highlands apartment is the 200 Park Terrace Dr Model at 200 Park Terrace Dr, Unit #1 starting at $2,800 with a $2.55 price per square foot in the Greenwood 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. |
|---|---|---|---|
| 476 Fulton St, Unit 1 | 476 Fulton St | 5BR,4.5BA | $0.65 |
| 200 Park Terrace Dr, Unit #1 | 200 Park Terrace Dr | 2BR,1BA | $2.55 |
| 159 Franklin St, Unit #D3 | 159 Franklin St | 2BR,1BA | $2.27 |
| 25R Auburn St, Unit #1 | 25R Auburn St | 2BR,1BA | $2.36 |
| 2 Fremont St, Unit 1 | 2 Fremont St | 2BR,1BA | $1.84 |
| 4 Pine St | 4 Pine St | 2BR,1BA | $2.65 |
| 7 Boline Pl, Unit 1 | 7 Boline Pl | 1BR,1BA | $2.30 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $2.44 |
| 48 Nashua St, Unit 3rd floor | 48 Nashua St | 1BR,1BA | $2.67 |
| 96 Main St, Unit 1 | 96 Main St | 1BR,1BA | $2.71 |
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Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 149 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,600 to $8,000. There are also 55 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,900 to $11,000.
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 $1,900 to $11,000 with an average monthly rent of $5,240.
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 $3,295 to $8,000, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $4,600. Four Bedroom Single-Family rentals are also available starting from $4,450 and Four Bedroom Apartments start at $4,800.
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.
The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.
Navigating the Rental Market: Tips for First-Time Renters
Written by: Sandy Baker
Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.
Rise of Digital Nomads: Remote Work Tips for Apartment Renters
Written by: Brandie Parton
As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.