Cheap Apartments for Rent in Middlebury, CT from $900 (10 Rentals)

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Search the lowest-cost Apartments available for rent right now in Middlebury.

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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Southwood Apartments
2 to 3 Bedroom Apartments

Southwood Apartments

933 Rubber AveNaugatuck, CT 06770
  • Utilities Included

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.

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.

Middlebury, CT Local Guide

Cheapest Available Middlebury Apartments for Rent and Nearby

 

The cheapest available apartment rental in Middlebury, CT is a 1 Bed unit found at 1243 W Main St in the Waterbury Middlebury neighborhood priced from $1,250. Bunker Hill in the Waterbury Middlebury neighborhood has the second lowest priced unit, which is a 2 Beds apartment currently listed from $1,315. Here is today’s list of the most affordable Middlebury apartments for rent:

Apartment ListingModel NameBed/BathPriced From
1243 W Main StOne Bedroom1BR,1BA$1,250
Bunker HillTwo Bedroom2BR,1BA$1,315
223 Meadow St7A1BR,1BA$1,500

Best Value Apartments for Rent in Middlebury, CT and Nearby

As of May 16, 2025 the best value apartment in the Middlebury area is the $1.00 price per square foot 7A Model at 223 Meadow St in the in the The Village at Oxford Greens neighborhood starting from $1,500. The second greatest value Middlebury apartment is the 1480 Highland Ave Model at 1480 Highland Ave, Unit 1480 starting at $2,200 with a $1.83 price per square foot in the Seymour Naugatuck Ansonia neighborhood. Here is today’s list of the best values for Middlebury apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
223 Meadow St7A1BR,1.5BA$1.00
1480 Highland Ave, Unit 14801480 Highland Ave2BR,1.5BA$1.83
95 Bristol St, Unit 3C95 Bristol St2BR,1.5BA$1.64
Middlebury Crossing Apartments2 Bedroom/1.5 Bath Townhome2BR,1.5BA$1.68
Greenbriar Hills Apartments2 Bedroom 1.5 Bath Townhome2BR,1.5BA$1.81
Parkview ApartmentsBryant1BR,1BA$1.99
Villa Square LLC1 Bedroom Townhouse, New Kitchen1BR,1.5BA$2.11
Horizon Homes1-Bedroom Deluxe1BR,1BA$2.08
1243 W Main StOne Bedroom1BR,1BA$1.67
WoodburyLily RenovatedStudio ,1BA$4.00

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Middlebury, CT Rentals by Map

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Getting Around Middlebury, CT

Walk Score®

26 / 100

Car-Dependent

Most errands require a car

Bike Score®

25 / 100

Somewhat Bikeable

Minimal bike infrastructure

Transit Score®

1 / 100

Minimal Transit

It may be possible to get on a bus

Frequently Asked Questions about Cheap Middlebury Apartments

How much is rent for a Cheap One Bedroom Middlebury Apartment?

The lowest price for a Cheap One Bedroom Middlebury Apartment is $1,250 at 1243 W Main St.

What is the lowest price for a Cheap Two Bedroom Middlebury Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Middlebury is starting from $1,315 at Bunker Hill.

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.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

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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.

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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.

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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.

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Rise of Digital Nomads: Remote Work Tips for Apartment Renters

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As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.