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Cheap Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA from $1,900 (23 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester Highlands area of Winchester.
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35 Prospect St, Unit 35 Prospect St # 102
35 Prospect St
WoburnMA01801
35 Prospect St
WoburnMA01801
282 Main St, Unit 2
282 Main St
StonehamMA02180
537 Main St
WoburnMA01801
537 Main St
WoburnMA01801
38 Warren Ave
WoburnMA01801
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289 Elm St, Unit 14
289 Elm St
MedfordMA02155
29 -2 Arlington Rd
WoburnMA01801
343 Washington St
WinchesterMA01890
343 Washington St
WinchesterMA01890
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit 239
200 Swanton St
WinchesterMA01890
159 Main St, Unit 37A
159 Main St
StonehamMA02180
131 Franklin St
StonehamMA02180
63-65-65 Harvard St
WinchesterMA01890
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit 2
200 Swanton St
WinchesterMA01890
22 Scott St, Unit 1
22 Scott St
WoburnMA01801
Showing Results 1-23, 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 | $3,055 | $2,500 | $4,500 |
| Winchester Highlands 3 Bedroom Homes for Rent | $3,556 | $2,900 | $4,100 |
| Winchester Highlands 4 Bedroom Homes for Rent | $6,078 | $4,000 | $10,000+ |
| Winchester Highlands 5 Bedroom Homes for Rent | $5,853 | $4,700 | $7,000 |
Browse Homes for Rent in this Neighborhood
There are currently 23 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
| 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 July 24, 2025 the best value apartment in the Winchester Highlands area is the $0.35 price per square foot 8 Cross St Model at 8 Cross St in the in the Walnut Hill neighborhood starting from $3,500. The second greatest value Winchester Highlands apartment is the 8 Cross St Model at 8 Cross St, Unit 1 starting at $3,500 with a $0.35 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 | 8 Cross St | 3BR,1.5BA | $0.35 |
| 8 Cross St, Unit 1 | 8 Cross St | 3BR,1.5BA | $0.35 |
| 10 Cross St, Unit 1 | 10 Cross St | 3BR,1BA | $0.35 |
| 487 Fulton St | 487 Fulton St | 4BR,4.5BA | $0.48 |
| 14 Richardson St, Unit #14x | 14 Richardson St | 2BR,1BA | $1.60 |
| 15 Church Ave, Unit 2 | 15 Church Ave | 1BR,1BA | $1.53 |
| 15 Church Ave, Unit #2 | 15 Church Ave | 1BR,1BA | $2.00 |
| 224 Main St, Unit 0A | 224 Main St | 2BR,1BA | $2.10 |
| 35 Montvale Ave | 35 Montvale Ave | 2BR,1BA | $1.75 |
| 7 Boline Pl, Unit 1 | 7 Boline Pl | 1BR,1BA | $2.30 |
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Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 145 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,700 to $7,500. There are also 77 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,950 to $10,000.
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 $1,950 to $10,000 with an average monthly rent of $4,133.
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 $2,900 to $7,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,900 to $4,100. Four Bedroom Single-Family rentals are also available starting from $4,000 and Four Bedroom Apartments start at $3,200.
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.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.
The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.
Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.