2 Bedroom Apartments for Rent in Middlebury, CT (49 Rentals)

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property at 18 Bridge St

18 Bridge St

NaugatuckCT06770
property at 64 Far View Cmns

64 Far View Cmns

SouthburyCT06488
property at 550 High St

550 High St

NaugatuckCT06770
property at 574 Heritage Vlg

574 Heritage Vlg

SouthburyCT06488
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Southwood Apartments
2 Bedroom Apartments

Southwood Apartments

933 Rubber AveNaugatuck, CT 06770
  • Utilities Included
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Parkview
2 Bedroom Apartments

Parkview

585 Park RdWaterbury, CT 06708
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102 Spring St
2 Bedroom Apartments

102 Spring St

102 Spring StNaugatuck, CT 06770
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Oronoke Woods
2 Bedroom Apartments

Oronoke Woods

827 Oronoke RdWaterbury, CT 06708
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8 Pond St
2 Bedroom Apartments

8 Pond St

8 Pond StNaugatuck, CT 06770
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1370 Highland Ave
2 Bedroom Apartments

1370 Highland Ave

1370 Highland AveWaterbury, CT 06708
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68 Anderson St
2 Bedroom Apartments

68 Anderson St

68 Anderson StNaugatuck, CT 06770
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1481 Southford Rd
2 Bedroom Apartments

1481 Southford Rd

1481 Southford RdSouthbury, CT 06488
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138 New Haven Ave
2 Bedroom Apartments

138 New Haven Ave

138 New Haven AveWaterbury, CT 06708
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15-25 Elmview Cir
2 Bedroom Apartments

15-25 Elmview Cir

15-25 Elmview CirWaterbury, CT 06708
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48 Elmview Cir
2 Bedroom Apartments

48 Elmview Cir

48 Elmview CirWaterbury, CT 06708
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95-97 Fern St
2 Bedroom Apartments

95-97 Fern St

95-97 Fern StNaugatuck, CT 06770
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150 Mohican Ave
2 Bedroom Apartments

150 Mohican Ave

150 Mohican AveWaterbury, CT 06708
Showing Results 1-49, Page 1 of 1

Middlebury, CT Local Guide

Largest Available Middlebury 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Middlebury, CT is found at 1243 W Main St in the Waterbury Middlebury neighborhood and is 1,200 square feet priced from $1,600. Oxford Commons in the Seymour Naugatuck Ansonia neighborhood has the second largest 2 Bedroom, which is sized at 1,120 square feet and currently listed start at $2,025. Here is today’s list of the largest available 2 Bedroom units in Middlebury:

Apartment ListingModel NameSquare FootagePriced From
1243 W Main St2 Bdrm1,200 Sq Ft$1,600
Oxford CommonsChelsea 2-Bdrm/2-Bath1,120 Sq Ft$2,025
Middlebury Crossing Apartments2 Bedroom/1.5 Bath Townhome1,100 Sq Ft$1,850
Greenbriar Hills Apartments2 Bedroom 1.5 Bath Townhome1,056 Sq Ft$1,945
Villa Square LLCBuilding 1 Two Bedroom933 Sq Ft$1,950

Cheapest Available Middlebury 2 Bedroom Apartments

As of April 10, 2025 the lowest priced 2 Bedroom apartment unit in Middlebury, CT is the Two Bedroom Model starting from $1,315 at Bunker Hill in the Waterbury Middlebury neighborhood. The second most affordable Middlebury 2 Bedroom is the Two Bedroom/ 1 Bath Model at Middlebury Crossing Apartments starting at $1,550 . The average price for all 2 Bedroom apartments in Middlebury is currently $1,874. Here is today’s list of the cheapest available 2 Bedroom options in Middlebury:

Apartment ListingModel NamePriced From
Bunker HillTwo Bedroom$1,315
Middlebury Crossing ApartmentsTwo Bedroom/ 1 Bath$1,550
1243 W Main St2 Bdrm$1,600
Villa Square LLC2 Bedroom Townhouse, Cinch$1,750
Greenbriar Hills Apartments2 Bedroom 1.5 Bath Townhome$1,945

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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

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 2 Bedroom Middlebury Apartments

How much is the average rent for a 2 Bedroom Middlebury Apartment?

The average rent for a 2 Bedroom Apartment in Middlebury is $1,874.

What is the largest available 2 Bedroom Middlebury Apartment for rent?

Today's apartment with the most square footage in Middlebury is a 1,200 square feet unit starting from $1,600 at 1243 W Main St.

What is the average size for Middlebury 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Middlebury is currently 1,171 sq ft.

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 Renting Smart: Lease Basics Every Renter Needs article

Renting Smart: Lease Basics Every Renter Needs

Written by: Christine Leonard, Esq.

Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

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Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

Written by: Andrea Lee Negroni, JD

While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.

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Understanding Amenity Fees: Know Where You Might Be Able to Save Money

Written by: Amber Kanuckel

With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

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How Your Move-In Inspection Can Protect Your Security Deposit

Written by: Christine Leonard, Esq.

If you’re anything like most people, housing costs represent a huge chunk of your monthly budget. On top of that, moving can be both a stressful and expensive affair.