81 Angel Dr
WaterburyCT06708
Cheap Homes for Rent in Middlebury, CT from $1,100 (15 Rentals)
Search the lowest-cost Homes available for rent right now in Middlebury.
38 Sanford Rd
WoodburyCT06798
84 Ives St
WaterburyCT06704
335 Meriden Rd
WaterburyCT06705
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
161 Prospect St
WaterburyCT06710
250 Wood St
WaterburyCT06704
92 Temple St
WaterburyCT06706
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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489 Wilson St
WaterburyCT06708
158 Martone St
WaterburyCT06708
41 Sheffield Ln
NaugatuckCT06770
617 Millville Ave
NaugatuckCT06770
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.
50 City Hill St
NaugatuckCT06770
182 Meadow St
NaugatuckCT06770
55 Porter Ave
NaugatuckCT06770
Showing Results 1-15, Page 1 of 1
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 | $2,354 | $1,350 | $7,000 |
| Middlebury 3 Bedroom Homes for Rent | $2,767 | $1,300 | $4,250 |
| Middlebury 4 Bedroom Homes for Rent | $3,211 | $2,200 | $4,800 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Homes for Rent in Middlebury
Explore Middlebury
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 Studio unit found at Villa Square LLC in the Waterbury Middlebury neighborhood priced from $1,250. 1243 W Main St in the Waterbury Middlebury neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,250. Here is today’s list of the most affordable Middlebury apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Villa Square LLC | Efficiency | Studio,1BA | $1,250 |
| 1243 W Main St | One Bedroom | 1BR,1BA | $1,250 |
| Bunker Hill | Two Bedroom | 2BR,1BA | $1,315 |
| Trowbridge House Apartments | 1 Bedroom | 1BR,1BA | $1,395 |
| Horizon Homes | 1-Bedroom | 1BR,1BA | $1,560 |
Best Value Apartments for Rent in Middlebury, CT and Nearby
As of September 15, 2025 the best value apartment in the Middlebury area is the $1.53 price per square foot 3Beds Model at 223 Meadow St in the in the The Village at Oxford Greens neighborhood starting from $2,300. The second greatest value Middlebury apartment is the Chelsea 3-Bdrm/2-Bath Model at Oxford Commons starting at $2,125 with a $1.90 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 | 3Beds | 3BR,1.5BA | $1.53 |
| Oxford Commons | Chelsea 3-Bdrm/2-Bath | 3BR,2BA | $1.90 |
| Middlebury Crossing Apartments | 2 Bedroom/1.5 Bath Townhome | 2BR,1.5BA | $1.77 |
| 95 Bristol St, Unit 3D | 95 Bristol St | 2BR,1.5BA | $1.64 |
| Greenbriar Hills Apartments | 2 Bedroom 1.5 Bath Townhome | 2BR,1.5BA | $2.00 |
| West Hill Apartments | Town Home with Full Basement | 2BR,1.5BA | $1.91 |
| Parkview Apartments | Gramercy | 2BR,1BA | $2.17 |
| Trowbridge House Apartments | 2 Bedroom | 2BR,1BA | $1.79 |
| 1243 W Main St | One Bedroom | 1BR,1BA | $1.67 |
| Horizon Homes | 1-Bedroom | 1BR,1BA | $2.27 |
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See the most popular apartments and homes in Middlebury, CT
Frequently Asked Questions about Middlebury
What type of rentals are currently available in Middlebury?
There are currently 82 Apartments for Rent in Middlebury, CT with pricing that ranges from $950 to $2,500. There are also 54 Single Family Homes for rent, Condos, and Townhome rentals currently available in Middlebury ranging from $1,175 to $7,000.
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 $1,175 to $7,000 with an average monthly rent of $2,448.
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.
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.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.