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2 Bedroom Apartments
10 Old Waterbury Rd
10 Old Waterbury RdMiddlebury, CT 06762
2 Bedroom Apartments for Rent in Middlebury, CT (62 Rentals)
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$1,850 - $2,300
Plus Fees
2 Bedroom Apartments Available Now223 Meadow St
223 Meadow StNaugatuck, CT 06770
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$2,084 - $3,172
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$1,888 - $3,147
Required Monthly Fees
$25
Total Monthly Price
$1,913 - $3,172
Parkview
270 Spring StNaugatuck, CT 06770
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$1,950 - $1,970
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Available Jul 1Total Monthly Price
Base Rent
$1,730 - $1,970
Total Monthly Price
$1,730 - $1,970
Horizon Homes
151 Andrew AveNaugatuck, CT 06770
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Rent Specials
Contact Us For Pricing2 Bedroom Apartments Contact Us For Availability
Woodbury Knoll
302 Tuttle RdWoodbury, CT 06798
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$1,700 - $1,995
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Contact Us For AvailabilityTotal Monthly Price
Base Rent
$1,700 - $1,995
Total Monthly Price
$1,700 - $1,995
West Hill Apartments
597 Millville AveNaugatuck, CT 06770
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Rent Specials
$1,745 - $1,995
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowMiddlebury Crossing Apartments
77 Newfield AveWaterbury, CT 06708
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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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$1,995
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jul 1Total Monthly Price
Base Rent
$1,995
Total Monthly Price
$1,995
51 Park Ave, Unit 1
51 Park AveNaugatuck, CT 06770
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$1,750
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,750
Total Monthly Price
$1,750
307 N Main St, Unit 2
307 N Main StNaugatuck, CT 06770
Renting with Roommates: Realistic Expectations for Shared Lease
Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.
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$1,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,800
Total Monthly Price
$1,800
95 Bristol St, Unit 3C
95 Bristol StWaterbury, CT 06708
32 Greenwood St
NaugatuckCT06770
14 Guilfoile St, Unit 2
14 Guilfoile St
WaterburyCT06708
1106 Main St
WatertownCT06795
108 Curtiss St
NaugatuckCT06770
14 Edgewood Rd
WatertownCT06779
23 Dunn Ave
NaugatuckCT06770
285 Hillside Ave
NaugatuckCT06770
675 Millville Ave
NaugatuckCT06770
173 Bradley Ave
WaterburyCT06708
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.
44 Armand Dr
WaterburyCT06708
109 Bunker Hill Ave
WaterburyCT06708
27 Katie Ln
WaterburyCT06708
23 Katie Ln
WaterburyCT06708
1101 Highland Ave
WaterburyCT06708
219 Nichols Dr
WaterburyCT06708
75 Vernon St
WaterburyCT06708
14 Guilfoile St
WaterburyCT06708
951 Chase Pkwy
WaterburyCT06708
150 Chestnut Ave
WaterburyCT06710
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.
105 Division St
WaterburyCT06704
1720 E Main St
WaterburyCT06705
48 Irion St
WaterburyCT06704
909 Hamilton Ave
WaterburyCT06706
58 High St
WaterburyCT06704
220 Alder St
WaterburyCT06708
107 Main St N
WoodburyCT06798
17 Pleasant St
WoodburyCT06798
593 Heritage Vlg
SouthburyCT06488
91 Taft Pointe
WaterburyCT06708
Renting Smart: Lease Basics Every Renter Needs
Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com
61 Far View Cmns
SouthburyCT06488
13 Rowland Farm Rd
OxfordCT06478
285 Hillside Ave
NaugatuckCT06770
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2 Bedroom Apartments
Oronoke Woods
827 Oronoke RdWaterbury, CT 06708
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2 Bedroom Apartments
102 Spring St
102 Spring StNaugatuck, CT 06770
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2 Bedroom Apartments
1108 W Main St
1108 W Main StWaterbury, CT 06708
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2 Bedroom Apartments
83-93 Whitewood Rd
83-93 Whitewood RdWaterbury, CT 06708
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2 Bedroom Apartments
Parkview
585 Park RdWaterbury, CT 06708
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2 Bedroom Apartments
147 Fairfield Ave
147 Fairfield AveWaterbury, CT 06708
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2 Bedroom Apartments
150 Mohican Ave
150 Mohican AveWaterbury, CT 06708
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
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 | $1,486 | $1,200 | $1,599 |
| Middlebury 1 Bedroom Apartments | $1,645 | $1,300 | $1,913 |
Middlebury 2 Bedroom Apartments | $1,887 | $1,450 | $2,250 |
| Middlebury 3 Bedroom Apartments | $2,031 | $1,649 | $2,500 |
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
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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 |
| Middlebury Crossing Apartments | 2 Bedroom/1.5 Bath Townhome | 1,100 Sq Ft | $1,995 |
| Parkview | GRAMERCY | 980 Sq Ft | $2,109 |
Cheapest Available Middlebury 2 Bedroom Apartments
As of June 23, 2026 the lowest priced 2 Bedroom apartment unit in Middlebury, CT is the 2 Bdrm Model starting from $1,600 at 1243 W Main St 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 $1,745 . The average price for all 2 Bedroom apartments in Middlebury is currently $1,887. Here is today’s list of the cheapest available 2 Bedroom options in Middlebury:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| 1243 W Main St | 2 Bdrm | $1,600 |
| Middlebury Crossing Apartments | Two Bedroom/ 1 Bath | $1,745 |
| 223 Meadow St | 2Beds | $1,850 |
| Parkview | GRAMERCY | $2,109 |
Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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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 1243 W Main St listed at $1,600.
How much is the average rent for a 2 Bedroom Middlebury Apartment?
The average rent for a 2 Bedroom Apartment in Middlebury is $1,887.
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 2,120 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
Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.
Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.