Cheap Homes for Rent in Winchester, MA from $1,600 (67 Rentals)

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Search the lowest-cost Homes available for rent right now in Winchester.

property at 200 Swanton St

200 Swanton St

WinchesterMA01890
property at 15 Forest St

15 Forest St

MedfordMA02155

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.

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property at 26 Heath Rd

26 Heath Rd

ArlingtonMA02474
property at 19 Arizona Ter

19 Arizona Ter

ArlingtonMA02474

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.

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property at 422 High St

422 High St, Unit 10

422 High St
MedfordMA02155
property at 35 Prospect St

35 Prospect St

WoburnMA01801

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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property at 27 N Union St

27 N Union St

ArlingtonMA02474

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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property at 79 Capen St

79 Capen St

MedfordMA02155
property at 24 South St

24 South St

MedfordMA02155

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 1-50, Page 1 of 2

Winchester, MA Local Guide

Cheapest Available Winchester Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
Leisure Lane Apartmentssmall 1 bedroom1BR,1BA$1,925

Best Value Apartments for Rent in Winchester, MA

As of June 12, 2025 the best value apartment in the Winchester area is the $0.39 price per square foot 125 Hillsdale Rd Model at 125 Hillsdale Rd, Unit 1 in the in the Strawberry Hill neighborhood starting from $3,894. The second greatest value Winchester apartment is the 79 Capen St Model at 79 Capen St, Unit 1 starting at $2,690 with a $0.27 price per square foot in the North Medford neighborhood. Here is today’s list of the best values for Winchester apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
125 Hillsdale Rd, Unit 1125 Hillsdale Rd3BR,1BA$0.39
79 Capen St, Unit 179 Capen St2BR,1BA$0.27
5 Forest St, Unit #4015 Forest St2BR,1BA$0.27
1 Victoria St, Unit 1A1 Victoria St2BR,1BA$0.34
260 Boston Ave, Unit 1260 Boston Ave3BR,1BA$0.33
258 Boston Ave, Unit 3258 Boston Ave3BR,1BA$0.34
50 Conwell Ave, Unit 250 Conwell Ave3BR,1BA$0.31
29 Capen St, Unit #229 Capen St2BR,1.5BA$0.30
8 Forest St, Unit #2018 Forest St2BR,1BA$0.26
15 Hudson St, Unit R15 Hudson St2BR,1BA$0.31

Quick Rent Budget Calculator

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Frequently Asked Questions about Winchester

What type of rentals are currently available in Winchester?

There are currently 816 Apartments for Rent in Winchester, MA with pricing that ranges from $955 to $10,400. There are also 503 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,650 to $40,000.

What is the current price range for Rental Homes in Winchester?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester ranges from $1,650 to $40,000 with an average monthly rent of $4,901.

How much are larger Three and Four Bedroom Rentals in Winchester?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester range from $2,500 to $7,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 to $6,550. Four Bedroom Single-Family rentals are also available starting from $3,425 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.

decorative image for The 10 Best Affordable Neighborhoods in Boston, MA article

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.

decorative image for The Art of the Rental Viewing: What to look for during a property tour article

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.

decorative image for Know Your Budget: Calculating What You Can Realistically Afford When Renting article

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.

decorative image for The Freedom of Short-Term Leases: Exploring the Advantages for Renters article

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.