191 Scott St
NaugatuckCT06770
Cheap Homes for Rent in Middlebury, CT from $1,000 (10 Rentals)
Search the lowest-cost Homes available for rent right now in Middlebury.
232 Waterville St
WaterburyCT06710
84 Ives St
WaterburyCT06704
161 Prospect St
WaterburyCT06710
259 Grove St
WaterburyCT06710
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.
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21 3rd St
WaterburyCT06708
23 Shirley St
WaterburyCT06708
22-24 Putnam St
WaterburyCT06704
77 Ross St
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.
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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 | $2,446 | $1,295 | $6,500 |
| Middlebury 3 Bedroom Homes for Rent | $2,463 | $1,300 | $4,500 |
| Middlebury 4 Bedroom Homes for Rent | $2,475 | $2,200 | $2,850 |
| Middlebury 5 Bedroom Homes for Rent | $10,250 | $3,500 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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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 Studio unit found at Villa Square LLC in the Waterbury Middlebury neighborhood priced from $1,225. 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 | $1,225 |
| 1243 W Main St | One Bedroom | 1BR,1BA | $1,250 |
| Trowbridge House Apartments | 1 Bedroom | 1BR,1BA | $1,395 |
Best Value Apartments for Rent in Middlebury, CT and Nearby
As of November 08, 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 53 Woodbine St Model at 53 Woodbine St, Unit 1 starting at $2,600 with a $2.00 price per square foot in the The Village at Oxford Greens 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 |
| 53 Woodbine St, Unit 1 | 53 Woodbine St | 2BR,1BA | $2.00 |
| 97 Walnut St, Unit 97 | 97 Walnut St | 2BR,1BA | $1.58 |
| Oxford Commons | Chelsea 3-Bdrm/Affordable | 3BR,2BA | $1.74 |
| 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 |
| 1521 Highland Ave, Unit 1521 Highland Avenue | 1521 Highland Ave | 2BR,1.5BA | $2.00 |
| 1541 Highland Ave, Unit H | 1541 Highland Ave | 2BR,1.5BA | $2.00 |
| Trowbridge House Apartments | 1 Bedroom | 1BR,1BA | $1.75 |
| 1243 W Main St | One Bedroom | 1BR,1BA | $1.67 |
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.
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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.
Read ArticleThe 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.
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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 95 Apartments for Rent in Middlebury, CT with pricing that ranges from $800 to $2,600. There are also 41 Single Family Homes for rent, Condos, and Townhome rentals currently available in Middlebury ranging from $1,050 to $17,000.
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 $1,050 to $17,000 with an average monthly rent of $3,447.
How much are larger Three and Four Bedroom Rentals in Middlebury?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Middlebury range from $1,800 to $2,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,300 to $4,500. Four Bedroom Single-Family rentals are also available starting from $2,200 and Four Bedroom Apartments start at $2,000.
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.
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.
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.