114 Cooke St
WaterburyCT06710
Cheap Homes for Rent in Middlebury, CT from $1,000 (9 Rentals)
Search the lowest-cost Homes available for rent right now in Middlebury.
17 3rd St
WaterburyCT06708
84 Ives St
WaterburyCT06704
94 Oak St
WaterburyCT06704
335 Meriden Rd
WaterburyCT06705
250 Wood St
WaterburyCT06704
81 Chipman St
WaterburyCT06708
14 Edgewood Rd
OakvilleCT06779
489 Wilson St
WaterburyCT06708
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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 a home in Middlebury?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Middlebury 2 Bedroom Homes for Rent | $1,963 | $1,195 | $2,850 |
| Middlebury 3 Bedroom Homes for Rent | $1,680 | $1,300 | $2,500 |
| Middlebury 4 Bedroom Homes for Rent | $3,507 | $2,300 | $4,950 |
| Middlebury 5 Bedroom Homes for Rent | $3,550 | $3,100 | $4,000 |
| Middlebury 6 Bedroom Homes for Rent | $2,600 | $2,600 | $2,600 |
Browse Top Homes for Rent in Middlebury
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Middlebury, CT Local Guide
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Cheapest Available Middlebury Apartments for Rent and Nearby
The cheapest available apartment rental in Middlebury, CT is a 1 Bed unit found at 1243 W Main St in the Waterbury Middlebury neighborhood priced from $1,250. Bunker Hill in the Waterbury Middlebury neighborhood has the second lowest priced unit, which is a 2 Beds apartment currently listed from $1,315. Here is today’s list of the most affordable Middlebury apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 1243 W Main St | One Bedroom | 1BR,1BA | $1,250 |
| Bunker Hill | Two Bedroom | 2BR,1BA | $1,315 |
| Trowbridge House Apartments | 1 Bed, 1 bath | 1BR,1BA | $1,395 |
Best Value Apartments for Rent in Middlebury, CT and Nearby
As of July 25, 2025 the best value apartment in the Middlebury area is the $1.00 price per square foot 7A Model at 223 Meadow St in the in the The Village at Oxford Greens neighborhood starting from $1,500. The second greatest value Middlebury apartment is the 1480 Highland Ave Model at 1480 Highland Ave, Unit 1480 starting at $2,200 with a $1.83 price per square foot in the Seymour Naugatuck Ansonia neighborhood. Here is today’s list of the best values for Middlebury apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 223 Meadow St | 7A | 1BR,1.5BA | $1.00 |
| 1480 Highland Ave, Unit 1480 | 1480 Highland Ave | 2BR,1.5BA | $1.83 |
| 1482 Highland Ave, Unit TARTZ REALTY | 1482 Highland Ave | 2BR,1.5BA | $2.00 |
| 95 Bristol St, Unit 3D | 95 Bristol St | 2BR,1.5BA | $1.64 |
| Middlebury Crossing Apartments | 2 Bedroom/1.5 Bath Townhome | 2BR,1.5BA | $1.68 |
| West Hill Apartments | Town Home with Full Basement | 2BR,1.5BA | $1.86 |
| 1541 Highland Ave, Unit I | 1541 Highland Ave | 2BR,1.5BA | $2.00 |
| Parkview Apartments | Bryant | 1BR,1BA | $2.12 |
| Trowbridge House Apartments | 1 Bed, 1 bath | 1BR,1BA | $1.80 |
| 1243 W Main St | One Bedroom | 1BR,1BA | $1.67 |
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Frequently Asked Questions about Middlebury
What type of rentals are currently available in Middlebury?
There are currently 80 Apartments for Rent in Middlebury, CT with pricing that ranges from $1,100 to $2,500. There are also 38 Single Family Homes for rent, Condos, and Townhome rentals currently available in Middlebury ranging from $1,075 to $4,950.
What is the current price range for Rental Homes in Middlebury?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Middlebury ranges from $1,075 to $4,950 with an average monthly rent of $2,292.
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.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.
The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.
Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.
The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.