68 Adelaide Ave
WaterburyCT06708
Cheap Homes for Rent in Middlebury, CT from $900 (6 Rentals)
Search the lowest-cost Homes available for rent right now in Middlebury.
63 Woodbine St
NaugatuckCT06770
240 Scott St
NaugatuckCT06770
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.
140 Hamden Ave
WaterburyCT06704
47 Quassuk Rd
WoodburyCT06798
45 Ives St
WaterburyCT06704
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.
Showing Results 1-6, 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 | $2,495 | $1,400 | $6,500 |
| Middlebury 3 Bedroom Homes for Rent | $2,780 | $1,800 | $3,950 |
| Middlebury 4 Bedroom Homes for Rent | $3,038 | $1,950 | $4,000 |
| Middlebury 5 Bedroom Homes for Rent | $17,000 | $10,000 | $10,000+ |
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
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
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 $1,350. Villa Square LLC in the Waterbury Middlebury neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,375. 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 | $1,350 |
| Villa Square LLC | Large Studio | Studio,1BA | $1,375 |
| Trowbridge House Apartments | 1 Bedroom | 1BR,1BA | $1,395 |
Best Value Apartments for Rent in Middlebury, CT and Nearby
As of February 24, 2026 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 $2,100 with a $1.88 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 | $1.88 |
| 95 Bristol St, Unit 3A | 95 Bristol St | 2BR,1.5BA | $1.64 |
| 1521 Highland Ave, Unit 1521 Highland Avenue | 1521 Highland Ave | 2BR,1.5BA | $2.00 |
| Middlebury Crossing Apartments | 2 Bedroom/1.5 Bath Townhome | 2BR,1.5BA | $1.77 |
| 307 N Main St, Unit 2 | 307 N Main St | 2BR,1BA | $1.75 |
| Parkview Apartments | Gramercy | 2BR,1BA | $2.08 |
| Trowbridge House Apartments | 1 Bedroom | 1BR,1BA | $1.75 |
| Horizon Homes | 1-Bedroom | 1BR,1BA | $2.06 |
| 1243 W Main St | One Bedroom | 1BR,1BA | $1.80 |
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 Article
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.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Read ArticleQuick 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 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 $1,200 to $2,800. There are also 32 Single Family Homes for rent, Condos, and Townhome rentals currently available in Middlebury ranging from $900 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 $900 to $17,000 with an average monthly rent of $5,439.
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
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.