Cheap Apartments for Rent in Middlebury, CT from $800 (7 Rentals)

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

property at 155 Robbins St

155 Robbins St

WaterburyCT06708
property at 100 Media Ave

100 Media Ave

WaterburyCT06708
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Southwood Apartments
2 to 3 Bedroom Apartments

Southwood Apartments

933 Rubber AveNaugatuck, CT 06770
  • Utilities Included
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Bunker Hill
1 to 3 Bedroom Apartments

Bunker Hill

17 Eastern AveWaterbury, CT 06708
  • Utilities Included
property at 191 Scott St

191 Scott St

NaugatuckCT06770

Middlebury, CT Local Guide

Cheapest Available Middlebury Apartments for Rent and Nearby

 

The cheapest available apartment rental in Middlebury, CT is a Studio unit found at Villa Square LLC in the Waterbury Middlebury neighborhood priced from $1,225. 1243 W Main St in the Waterbury Middlebury neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,250. Here is today’s list of the most affordable Middlebury apartments for rent:

Apartment ListingModel NameBed/BathPriced From
Villa Square LLCEfficiencyStudio,1BA$1,225
1243 W Main StOne Bedroom1BR,1BA$1,250
Trowbridge House Apartments1 Bedroom1BR,1BA$1,395

Best Value Apartments for Rent in Middlebury, CT and Nearby

As of November 02, 2025 the best value apartment in the Middlebury area is the $1.53 price per square foot 3Beds Model at 223 Meadow St in the in the The Village at Oxford Greens neighborhood starting from $2,300. The second greatest value Middlebury apartment is the 53 Woodbine St Model at 53 Woodbine St, Unit Unit 1 starting at $2,600 with a $2.00 price per square foot in the The Village at Oxford Greens 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 St3Beds3BR,1.5BA$1.53
53 Woodbine St, Unit Unit 153 Woodbine St2BR,1BA$2.00
Oxford CommonsChelsea 3-Bdrm/Affordable3BR,2BA$1.74
Middlebury Crossing Apartments2 Bedroom/1.5 Bath Townhome2BR,1.5BA$1.77
95 Bristol St, Unit 3D95 Bristol St2BR,1.5BA$1.64
1521 Highland Ave, Unit 1521 Highland Avenue1521 Highland Ave2BR,1.5BA$2.00
1541 Highland Ave, Unit H1541 Highland Ave2BR,1.5BA$2.00
Parkview ApartmentsBryant1BR,1BA$2.09
Trowbridge House Apartments1 Bedroom1BR,1BA$1.75
1243 W Main StOne Bedroom1BR,1BA$1.67

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

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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

What is the Cheapest Studio apartment in Middlebury?

Currently the most affordable Cheap Studio Apartment in Middlebury is at Villa Square LLC listed at $1,250.

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 $1,600 at Villa Square LLC.

What is the most affordable Middlebury Three Bedroom Apartment?

The best deal on a cheap Middlebury Three Bedroom Apartment rental is at Oxford Commons and starts from $1,950.

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 Apartment Common Area Rules: What Renters Need to Know article

Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

decorative image for Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between article

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.