close
View Me
2 Bedroom Apartments
10 Old Waterbury Rd
10 Old Waterbury RdMiddlebury, CT 06762
2 Bedroom Apartments for Rent in Middlebury, CT (53 Rentals)
close
View Me
$1,595 - $1,750
Total Monthly Price
Base Rent$1,395 - $1,750
Total Monthly Price$1,395 - $1,750
Trowbridge House Apartments
38 Highland AveNaugatuck, CT 06770
close
View Me
$1,850 - $2,300
Total Monthly Price
Base Rent$1,850 - $2,400
Total Monthly Price$1,850 - $2,400
223 Meadow St
223 Meadow StNaugatuck, CT 06770
close
View Me
Rent Specials
$2,185
Total Monthly Price
Base Rent$1,739 - $2,185
Total Monthly Price$1,739 - $2,185
Woodbury Knoll
302 Tuttle RdWoodbury, CT 06798
close
View Me
Rent Specials
$1,875
Total Monthly Price
Base Rent$1,525 - $1,795
Total Monthly Price$1,525 - $1,795
Horizon Homes
151 Andrew AveNaugatuck, CT 06770
close
View Me
$1,875 - $2,025
Total Monthly Price
Base Rent$1,505 - $2,025
Total Monthly Price$1,505 - $2,025
West Hill Apartments
597 Millville AveNaugatuck, CT 06770
close
View Me
Rent Specials
$1,745 - $1,995
Total Monthly Price
Base Rent$1,745 - $1,995
Total Monthly Price$1,745 - $1,995
Middlebury Crossing Apartments
77 Newfield AveWaterbury, CT 06708
close
View Me
$1,600 - $1,900
Total Monthly Price
Base Rent$1,350 - $1,900
Total Monthly Price$1,350 - $1,900
1243 W Main St
1243 W Main StWaterbury, CT 06708
close
View Me
$2,064 - $2,195
Total Monthly Price
Base Rent$1,709 - $2,195
Total Monthly PriceVaries
Platform at Naugatuck
20 Old Firehouse RdNaugatuck, CT 06770
53 Mohican Ave, Unit 2
53 Mohican Ave
WaterburyCT06708
Exploring Rental Options: Apartments, Townhomes, and Lofts—Oh My!
Looking for the perfect rental? From apartments and condos to lofts and single family rentals, explore the unique pros and cons of each rental type to help you land in your perfect new place.
145 Hoadley St
NaugatuckCT06770
174 Jordan Ave
OakvilleCT06779
14 Edgewood Rd
WatertownCT06779
23 Dunn Ave
NaugatuckCT06770
53 Mohican Ave
WaterburyCT06708
173 Lucille St
WaterburyCT06708
14 Guilfoile St
WaterburyCT06708
23 Katie Ln
WaterburyCT06708
40 Whitewood Rd
WaterburyCT06708
21 3rd St
WaterburyCT06708
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Looking for the perfect new rental? Learn great ways to spot the perfect apartment for you, identify common red flags, and avoid rental issues and scams with these expert provided actionable tips.
893 Highland Ave
WaterburyCT06708
158 Martone St
WaterburyCT06708
18 Bridge St
NaugatuckCT06770
58 High St
WaterburyCT06704
883 Rubber Ave
NaugatuckCT06770
184 Kaynor Dr
WaterburyCT06708
29 Hazelhurst Ave
WatertownCT06779
111 Mohican Ave
WaterburyCT06708
461 Spring St
NaugatuckCT06770
236 Cherry St
NaugatuckCT06770
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
1474 Highland Ave
WaterburyCT06708
925 Oronoke Rd
WaterburyCT06708
91 Taft Pointe
WaterburyCT06708
21 Cheryl Dr
WaterburyCT06708
72 Bennett Ave
WaterburyCT06708
close
View Me
2 Bedroom Apartments
Oronoke Woods
827 Oronoke RdWaterbury, CT 06708
close
View Me
2 Bedroom Apartments
102 Spring St
102 Spring StNaugatuck, CT 06770
close
View Me
2 Bedroom Apartments
1108 W Main St
1108 W Main StWaterbury, CT 06708
close
View Me
2 Bedroom Apartments
83-93 Whitewood Rd
83-93 Whitewood RdWaterbury, CT 06708
close
View Me
2 Bedroom Apartments
Parkview
585 Park RdWaterbury, 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.
close
View Me
2 Bedroom Apartments
147 Fairfield Ave
147 Fairfield AveWaterbury, CT 06708
close
View Me
2 Bedroom Apartments
150 Mohican Ave
150 Mohican AveWaterbury, CT 06708
close
View Me
2 Bedroom Apartments
95-97 Fern St
95-97 Fern StNaugatuck, CT 06770
close
View Me
2 Bedroom Apartments
48 Elmview Cir
48 Elmview CirWaterbury, CT 06708
close
View Me
2 Bedroom Apartments
15-25 Elmview Cir
15-25 Elmview CirWaterbury, CT 06708
close
View Me
2 Bedroom Apartments
138 New Haven Ave
138 New Haven AveWaterbury, CT 06708
close
View Me
2 Bedroom Apartments
68 Anderson St
68 Anderson StNaugatuck, CT 06770
close
View Me
2 Bedroom Apartments
1370 Highland Ave
1370 Highland AveWaterbury, CT 06708
close
View Me
2 Bedroom Apartments
8 Pond St
8 Pond StNaugatuck, CT 06770
close
View Me
2 Bedroom Apartments
Southwood Apartments
933 Rubber AveNaugatuck, 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.
Showing Results 1-50, Page 1 of 2
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 | $1,563 | $1,225 | $1,739 |
| Middlebury 1 Bedroom Apartments | $1,564 | $1,295 | $1,800 |
Middlebury 2 Bedroom Apartments | $1,853 | $1,450 | $2,250 |
| Middlebury 3 Bedroom Apartments | $2,114 | $1,700 | $2,400 |
| Middlebury 4 Bedroom Apartments | $2,095 | $2,095 | $2,095 |
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
- ZIP codes
- Local Counties
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 | $1,950 |
| Horizon Homes | 2-Bedroom/Main or Lower with Deck | 1,068 Sq Ft | $1,750 |
| West Hill Apartments | Town Home with Full Basement | 1,020 Sq Ft | $1,875 |
| Greenbriar Hills Apartments | 2 Bedroom 1 Bath | 960 Sq Ft | $2,025 |
| Platform at Naugatuck | 2 Bedroom | 951 Sq Ft | $2,064 |
Cheapest Available Middlebury 2 Bedroom Apartments
As of September 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 in the Waterbury neighborhood. The average price for all 2 Bedroom apartments in Middlebury is currently $1,853. 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 |
| West Hill Apartments | Town Home with Full Basement | $1,875 |
| Greenbriar Hills Apartments | 2 Bedroom 1 Bath | $2,025 |
| Platform at Naugatuck | 2 Bedroom | $2,064 |
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.
Read ArticleReal 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.
Read Article
Quick 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.
Let everyone know!
Do you know the Middlebury area?
If you’re an expert on all things Middlebury, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Middlebury, CT Rentals by Map
See the most popular apartments and homes in Middlebury, CT
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 $1,853.
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 1,496 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
Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.
How Commercial-to-Residential Property Conversions Help the Housing Crisis
Written by: Robin Stewart
Many housing markets throughout America share a common complaint: a lack of affordable rental properties.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.