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2 Bedroom Apartments for Rent in Middlebury, CT (58 Rentals)
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$1,850 - $2,100
Plus Fees
2 Bedroom Apartments Available Now223 Meadow St
223 Meadow StNaugatuck, CT 06770
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$1,818 - $1,889
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$1,750 - $1,833
Required Monthly Fees
$25
Total Monthly Price
$1,775 - $1,858
Parkview Apartments
270 Spring StNaugatuck, CT 06770
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$1,695 - $1,750
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowTrowbridge House Apartments
38 Highland AveNaugatuck, CT 06770
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$1,975
Plus Fees
2 Bedroom Apartments Contact Us For AvailabilityWoodbury Knoll
302 Tuttle RdWoodbury, CT 06798
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$1,895 - $1,995
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Contact Us For AvailabilityTotal Monthly Price
Base Rent
$1,895 - $1,995
Total Monthly Price
$1,895 - $1,995
West Hill Apartments
597 Millville AveNaugatuck, CT 06770
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$2,125 - $2,150
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Contact Us For AvailabilityTotal Monthly Price
Base Rent
$1,950 - $2,150
Total Monthly Price
$1,950 - $2,150
Oxford Commons
117 Hurley RdOxford, CT 06478
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$1,675 - $1,795
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$1,605 - $1,795
Total Monthly Price
$1,605 - $1,795
Horizon Homes
151 Andrew AveNaugatuck, CT 06770
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Rent Specials
$1,695 - $1,950
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowMiddlebury Crossing Apartments
77 Newfield AveWaterbury, CT 06708
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Rent Specials
$1,550 - $1,850
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowVilla Square LLC
222 Bradley AveWaterbury, CT 06708
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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$1,600 - $1,900
Plus Fees24 Month Lease Term
2 Bedroom Apartments Contact Us For Availability1243 W Main St
1243 W Main StWaterbury, CT 06708
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$2,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,200
Total Monthly Price
$2,200
1521 Highland Ave, Unit 1521 Highland Avenue
1521 Highland AveWaterbury, CT 06708
585 Park Rd, Unit 3-8
585 Park Rd
WaterburyCT06708
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50 Sunnyside Ave
WatertownCT06779
240 Scott St
NaugatuckCT06770
64 White Deer Rocks Rd
WoodburyCT06798
68 Anderson St
NaugatuckCT06770
253 N Main St
NaugatuckCT06770
37 Hungerford Ave
WatertownCT06779
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
141 Millville Ave
NaugatuckCT06770
117 Golden Hill St
NaugatuckCT06770
690 Highland Ave
WaterburyCT06708
38 Myrtle Ave
WaterburyCT06708
704 Highland Ave
WaterburyCT06708
54 New Haven Ave
WaterburyCT06708
20 Merrill St
WaterburyCT06708
226 Ledgeside Ave
WaterburyCT06708
134 Charles St
WaterburyCT06708
585 Park Rd
WaterburyCT06708
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.
60 Westwood Rd
WoodburyCT06798
58 High St
WaterburyCT06704
22 Holly St
WaterburyCT06706
14 Quassuk Rd
WoodburyCT06798
36 Washington Ave
WoodburyCT06798
101 Church Rd
SouthburyCT06488
33 Washington Ave
WoodburyCT06798
112 W Lake Rd
WoodburyCT06798
240 Scott St
NaugatuckCT06770
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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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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.
Middlebury, CT Local Guide
Sunset in the grass by Trenten Kelley is licensed under CC BY 2.0
How much does it cost to rent an apartment in Middlebury?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Middlebury Studio Apartments | $1,520 | $1,195 | $1,599 |
| Middlebury 1 Bedroom Apartments | $1,642 | $1,300 | $2,000 |
Middlebury 2 Bedroom Apartments | $1,784 | $1,400 | $2,200 |
| Middlebury 3 Bedroom Apartments | $2,032 | $1,600 | $2,400 |
| Middlebury 4 Bedroom Apartments | $2,700 | $2,700 | $2,700 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Apartments in Middlebury
See all Apartments in MiddleburyExplore Middlebury
Middlebury, CT Local Guide
- Nearby Cities
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- Local Counties
- School Districts
Largest Available Middlebury 2 Bedroom Apartments
The largest available 2 Bedroom apartment unit in Middlebury, CT is found at 223 Meadow St in the The Village at Oxford Greens neighborhood and is 1,500 square feet priced from $1,850. 1243 W Main St in the Waterbury Middlebury neighborhood has the second largest 2 Bedroom, which is sized at 1,200 square feet and currently listed start at $1,600. Here is today’s list of the largest available 2 Bedroom units in Middlebury:
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| 223 Meadow St | 2Beds | 1,500 Sq Ft | $1,850 |
| 1243 W Main St | 2 Bdrm | 1,200 Sq Ft | $1,600 |
| Villa Square LLC | 2 Bedroom Deluxe Townhouse | 1,197 Sq Ft | $1,850 |
Cheapest Available Middlebury 2 Bedroom Apartments
As of December 20, 2025 the lowest priced 2 Bedroom apartment unit in Middlebury, CT is the 2 Bedroom Ranch, Lower Level Model starting from $1,550 at Villa Square LLC in the Waterbury Middlebury neighborhood. The second most affordable Middlebury 2 Bedroom is the 2 Bdrm Model at 1243 W Main St starting at $1,600 . The average price for all 2 Bedroom apartments in Middlebury is currently $1,784. Here is today’s list of the cheapest available 2 Bedroom options in Middlebury:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Villa Square LLC | 2 Bedroom Ranch, Lower Level | $1,550 |
| 1243 W Main St | 2 Bdrm | $1,600 |
| Horizon Homes | 2-Bedroom | $1,675 |
| Trowbridge House Apartments | 2 Bedroom | $1,695 |
| 223 Meadow St | 2Beds | $1,850 |
| Parkview Apartments | Gramercy | $1,873 |
| Middlebury Crossing Apartments | 2 Bedroom/1.5 Bath Townhome | $1,950 |
| Greenbriar Hills Apartments | 2 Bedroom 1.5 Bath Townhome | $2,289 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleQuick 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.
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Remember the 3 Rules of Real Estate:Location, Location, Location!
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See the most popular apartments and homes in Middlebury, CT
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
What is the Cheapest apartment in Middlebury with 2 Bedroom?
Currently the most affordable 2 Bedroom in Middlebury is at Villa Square LLC listed at $1,550.
How much is the average rent for a 2 Bedroom Middlebury Apartment?
The average rent for a 2 Bedroom Apartment in Middlebury is $1,784.
What is the largest available 2 Bedroom Middlebury Apartment for rent?
Today's apartment with the most square footage in Middlebury is a 1,500 square feet unit starting from $1,850 at 223 Meadow 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 1,290 sq ft.
Expert Rental Resources
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.
Articles, How-To's, and Tips
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
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.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
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.