Cheap Apartments for Rent in Winchester, CT from $700 (17 Rentals)
Search the lowest-cost Apartments available for rent right now in Winchester.

Mill at Still River

Gilbert Clock Apartments
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.
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.
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.
Winchester, CT Local Guide

How much does it cost to rent an apartment in Winchester?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Winchester Studio Apartments | $1,100 | $1,000 | $1,200 |
Winchester 1 Bedroom Apartments | $1,174 | $799 | $1,500 |
Winchester 2 Bedroom Apartments | $1,783 | $1,250 | $2,200 |
Winchester 3 Bedroom Apartments | $1,595 | $1,595 | $1,595 |
Winchester 4 Bedroom Apartments | $1,595 | $1,595 | $1,595 |
Browse Top Apartments in Winchester
See all Apartments in WinchesterExplore Winchester
Winchester, CT Local Guide
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Winchester Apartments for Rent and Nearby
 Apartment Listing | Model Name | Bed/Bath | Priced From |
---|---|---|---|
Gilbert Clock Apartments | Studio | Studio,1BA | $1,000 |
Mill at Still River | 1BD Classic | 1BR,1BA | $1,500 |
Best Value Apartments for Rent in Winchester, CT and Nearby
As of June 04, 2025 the best value apartment in the Winchester area is the $1.97 price per square foot 1BD Classic Model at Mill at Still River in the starting from $1,500. The second greatest value Winchester apartment is the Studio Model at Gilbert Clock Apartments starting at $1,000 with a $1.67 price per square foot . Here is today’s list of the best values for Winchester apartments based on price per square foot:
Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
---|---|---|---|
Mill at Still River | 1BD Classic | 1BR,1BA | $1.97 |
Gilbert Clock Apartments | Studio | Studio ,1BA | $1.67 |
279 N Main St, Unit 6 | 279 N Main St | 1BR,1BA | $1.39 |
Quick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winchester, CT Rentals by Map
See the most popular apartments and homes in Winchester, CT
Getting Around Winchester, CT
Walk Score®
17 / 100
Car-Dependent
Almost all errands require a car
Bike Score®
10 / 100
Somewhat Bikeable
Minimal bike infrastructure
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 Apartments
How much is rent for a Cheap One Bedroom Winchester Apartment?
The lowest price for a Cheap One Bedroom Winchester Apartment is $1,150 at Gilbert Clock Apartments.
What is the lowest price for a Cheap Two Bedroom Winchester Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winchester is starting from $1,250 at Gilbert Clock Apartments.
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 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.

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.