68 Adelaide Ave
WaterburyCT06708
Cheap Homes for Rent in Middlebury, CT from $1,000 (16 Rentals)
Search the lowest-cost Homes available for rent right now in Middlebury.
134 Charles St
WaterburyCT06708
close
View Me
$1,400
Plus Fees
1 Bedroom Apartments Available Jan 2, 202627 W Hill Terrace
27 W Hill TerraceNaugatuck, CT 06770
259 Grove St
WaterburyCT06710
close
View Me
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.
15 Pilgrim Trail
WoodburyCT06798
240 Scott St
NaugatuckCT06770
925 Oronoke Rd
WaterburyCT06708
close
View Me
585 Park Rd
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.
585 Park Rd, Unit 3-8
585 Park Rd
WaterburyCT06708
10 Wood St
WaterburyCT06704
58 High St
WaterburyCT06704
14 Wildwood Ave
WaterburyCT06710
8 Burma Rd
SouthburyCT06488
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
155 Tracy Ave
WaterburyCT06706
Showing Results 1-16, 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 | $2,477 | $1,200 | $6,500 |
| Middlebury 3 Bedroom Homes for Rent | $2,667 | $1,500 | $3,950 |
| Middlebury 4 Bedroom Homes for Rent | $2,908 | $2,000 | $4,500 |
| Middlebury 5 Bedroom Homes for Rent | $10,200 | $3,400 | $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 Studio unit found at Villa Square LLC in the Waterbury Middlebury neighborhood priced from $1,195. 1243 W Main St in the Waterbury Middlebury neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,350. 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 | $1,195 |
| 1243 W Main St | One Bedroom | 1BR,1BA | $1,350 |
| Trowbridge House Apartments | 1 Bedroom | 1BR,1BA | $1,395 |
| Woodbury Knoll | Lily Renovated | Studio,1BA | $1,550 |
| Horizon Homes | 1-Bedroom | 1BR,1BA | $1,605 |
Best Value Apartments for Rent in Middlebury, CT and Nearby
As of December 28, 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/Affordable Model at Oxford Commons starting at $1,900 with a $1.70 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/Affordable | 3BR,2BA | $1.70 |
| Middlebury Crossing Apartments | 2 Bedroom/1.5 Bath Townhome | 2BR,1.5BA | $1.77 |
| 1521 Highland Ave, Unit 1521 Highland Avenue | 1521 Highland Ave | 2BR,1.5BA | $2.00 |
| Greenbriar Hills Apartments | 2 Bedroom 1.5 Bath Townhome | 2BR,1.5BA | $2.17 |
| Parkview Apartments | Bryant | 1BR,1BA | $2.02 |
| Trowbridge House Apartments | 1 Bedroom | 1BR,1BA | $1.75 |
| 1243 W Main St | One Bedroom | 1BR,1BA | $1.80 |
| Horizon Homes | 1-Bedroom | 1BR,1BA | $2.33 |
| 308 N Main St, Unit B | 308 N Main St | 1BR,1BA | $2.26 |
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 93 Apartments for Rent in Middlebury, CT with pricing that ranges from $1,195 to $2,700. There are also 42 Single Family Homes for rent, Condos, and Townhome rentals currently available in Middlebury ranging from $1,000 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 $1,000 to $17,000 with an average monthly rent of $4,042.
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 $1,600 to $2,400, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,500 to $3,950. Four Bedroom Single-Family rentals are also available starting from $2,000 and Four Bedroom Apartments start at $2,700.
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
How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips
Written by: Justin Habersaat
Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.
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.
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!