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from $1,600Studio Apartment Available Aug 1
219 Washington St, Unit 3
219 Washington StWinchester, MA 01890
Cheap Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA from $1,400 (26 Rentals)
Cheap Apartments in the Winchester Highlands area of Winchester.
2 Elmwood Ave
WinchesterMA01890
2 Elmwood Ave
WinchesterMA01890
2 Elmwood Ave
WinchesterMA01890
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from $2,2001 Bedroom Apartment Available May 31
253 Swanton St, Unit #428
253 Swanton StWinchester, MA 01890
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from $1,870Studio to 3 Bedroom Apartments Available May 16
Beacon Village
26 Beacon StBurlington, MA 01803
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5 Orchard Pl
StonehamMA02180
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.
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from $1,9001 Bedroom Apartment Available Now
157 Franklin St, Unit #B2
157 Franklin StStoneham, MA 02180
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from $1,9501 Bedroom Apartment Available Now
48 Nashua St, Unit 3rd floor
48 Nashua StWoburn, MA 01801
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from $2,1951 Bedroom Apartment Available Now
42 Cambridge Rd, Unit #117
42 Cambridge RdWoburn, MA 01801
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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.
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from $2,380Studio to 1 Bedroom Apartments Available Now
44 Montvale Avenue
44 Montvale AveWoburn, MA 01801
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from $2,4002 Bedroom Apartment Available Now
159 Franklin St, Unit #D3
159 Franklin StStoneham, MA 02180
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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
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Showing Results 1-26, 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 an apartment in Winchester Highlands?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester Highlands Studio Apartments | $2,515 | $1,600 | $2,736 |
| Winchester Highlands 1 Bedroom Apartments | $3,026 | $1,895 | $8,502 |
| Winchester Highlands 2 Bedroom Apartments | $3,888 | $1,900 | $9,371 |
| Winchester Highlands 3 Bedroom Apartments | $5,137 | $3,295 | $8,000 |
| Winchester Highlands 4 Bedroom Apartments | $4,974 | $4,800 | $5,500 |
| Winchester Highlands 5 Bedroom Apartments | $5,400 | $4,295 | $6,500 |
Browse Apartments in this Neighborhood
There are currently 26 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
See all Apartments in WinchesterExplore Winchester
Winchester Highlands, Winchester, MA Local Guide
- Nearby Winchester neighborhoods
- Nearby Cities
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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 08, 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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Pet Friendly LifestyleWinchester Highlands, Winchester, MA
Ranked #3
Among neighborhoods in Winchester, MA for Apartment listings with Pet Friendly Amenities
Pet Friendliness Lifestyle Score
4.0Pet Friendly
Getting Around the Winchester Highlands Neighborhood in Winchester, MA
Walk Score®
44 / 100
Car-Dependent
Most errands require a car
Bike Score®
65 / 100
Bikeable
Some bike infrastructure
Transit Score®
5 / 100
Minimal Transit
It may be possible to get on a bus
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Cheap Winchester Highlands Apartments
What is a cheap apartment in Winchester Highlands?
A cheap apartment is any apartment up to the 30% percentile of cost for the area, which in Winchester Highlands is under $1,950.
What is the price of a cheap apartment in Winchester Highlands?
The cheapest apartment in Winchester Highlands is Mill Street Gardens which is listed at $1,950, while the average apartment in Winchester Highlands costs $5,495.
What types of apartments are the cheapest in Winchester Highlands?
Student, low-income, and by-the-bed apartments are typically the cheapest rentals in most cities, though they require qualifying criteria to rent. There are 12 regular apartments in Winchester Highlands that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.
How do the prices of cheap apartments compare to the average apartment in Winchester Highlands?
Cheap apartments in Winchester Highlands have an average cost of $422 which is $5,073 cheaper than the average rent for all rentals in Winchester Highlands.
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.