364 Colonial Ave
WaterburyCT06704
Cheap Homes for Rent in Middlebury, CT from $1,200 (12 Rentals)
Search the lowest-cost Homes available for rent right now in Middlebury.
1720 E Main St
WaterburyCT06705
48 Irion St
WaterburyCT06704
118 Pullen Ave
WatertownCT06779
16 Pilgrim Trail
WoodburyCT06798
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$1,4502 Bedroom Apartments Available Now
40 Whitewood Rd
40 Whitewood RdWaterbury, CT 06708
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
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$1,6003 Bedroom Apartments Available Now
1110 W Main St
1110 W Main StWaterbury, CT 06708
259 Grove St
WaterburyCT06710
34 Arrowhead Way
WoodburyCT06798
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$1,6003 Bedroom Apartments Available Now
35 Merrill St
35 Merrill StWaterbury, CT 06708
89 Waterville St
WaterburyCT06710
46 Webb St
WaterburyCT06704
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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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 | $2,022 | $1,350 | $2,600 |
| Middlebury 3 Bedroom Homes for Rent | $2,513 | $1,600 | $3,700 |
| Middlebury 4 Bedroom Homes for Rent | $3,558 | $1,700 | $7,500 |
| 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.
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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 $1,350. Woodbury Knoll in the Danbury Newtown Monroe neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,599. 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 |
| Woodbury Knoll | Lily Renovated | Studio,1BA | $1,599 |
| Villa Square LLC | 1 Bedroom Townhouse, New Kitchen | 1BR,1BA | $1,625 |
| Middlebury Crossing Apartments | Two Bedroom/ 1 Bath | 2BR,1BA | $1,745 |
| 223 Meadow St | 2Beds | 2BR,1BA | $1,850 |
Best Value Apartments for Rent in Middlebury, CT and Nearby
As of May 27, 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/Affordable Model at Oxford Commons starting at $1,875 with a $1.67 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 | $1.67 |
| 95 Bristol St, Unit 2B | 95 Bristol St | 2BR,1.5BA | $1.64 |
| Middlebury Crossing Apartments | 2 Bedroom/1.5 Bath Townhome | 2BR,1.5BA | $1.81 |
| 56 Aetna St, Unit 2B | 56 Aetna St | 2BR,1BA | $1.88 |
| Villa Square LLC | 1 Bedroom Townhouse, New Kitchen | 1BR,1.5BA | $2.08 |
| 1243 W Main St | One Bedroom | 1BR,1BA | $1.80 |
| Woodbury Knoll | Lily Renovated | Studio ,1BA | $4.00 |
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.
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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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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.
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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 91 Apartments for Rent in Middlebury, CT with pricing that ranges from $1,200 to $2,400. There are also 43 Single Family Homes for rent, Condos, and Townhome rentals currently available in Middlebury ranging from $1,200 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 $1,200 to $17,000 with an average monthly rent of $5,333.
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
A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.
Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.
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.