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Rent Specials
$1,195 - $1,850
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowVilla Square LLC
222 Bradley AveWaterbury, CT 06708
Cheap Apartments for Rent in Middlebury, CT from $900 (9 Rentals)
Search the lowest-cost Apartments available for rent right now in Middlebury.
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$1,250 - $1,900
Plus Fees24 Month Lease Term
1 to 2 Bedroom Apartments Contact Us For Availability1243 W Main St
1243 W Main StWaterbury, CT 06708
118 Pullen Ave
WatertownCT06779
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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.
68 Adelaide Ave
WaterburyCT06708
114 Cooke St
WaterburyCT06710
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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.
134 Charles St
WaterburyCT06708
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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 an apartment in Middlebury?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Middlebury Studio Apartments | $1,534 | $1,195 | $1,599 |
| Middlebury 1 Bedroom Apartments | $1,651 | $1,300 | $2,000 |
| Middlebury 2 Bedroom Apartments | $1,788 | $1,400 | $2,200 |
| Middlebury 3 Bedroom Apartments | $2,010 | $1,600 | $2,400 |
| Middlebury 4 Bedroom Apartments | $2,700 | $2,700 | $2,700 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Apartments in Middlebury
See all Apartments in MiddleburyExplore Middlebury
Middlebury, CT Local Guide
- Nearby Cities
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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 $1,195. 1243 W Main St in the Waterbury Middlebury neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,250. 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 | $1,195 |
| 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 December 18, 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 $1,950 with a $1.74 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 | $1.74 |
| 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 |
| Greenbriar Hills Apartments | 2 Bedroom 1.5 Bath Townhome | 2BR,1.5BA | $2.21 |
| Parkview Apartments | Bryant | 1BR,1BA | $2.09 |
| Trowbridge House Apartments | 1 Bedroom | 1BR,1BA | $1.75 |
| 1243 W Main St | One Bedroom | 1BR,1BA | $1.67 |
| Horizon Homes | 1-Bedroom | 1BR,1BA | $2.33 |
| Woodbury Knoll | Lily Renovated | Studio ,1BA | $3.88 |
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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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.
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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
Getting Around Middlebury, CT
Walk Score®
26 / 100
Car-Dependent
Most errands require a car
Bike Score®
25 / 100
Somewhat Bikeable
Minimal bike infrastructure
Transit Score®
1 / 100
Minimal Transit
It may be possible to get on a bus
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Cheap Middlebury Apartments
What is the Cheapest Studio apartment in Middlebury?
Currently the most affordable Cheap Studio Apartment in Middlebury is at Villa Square LLC listed at $1,195.
How much is rent for a Cheap One Bedroom Middlebury Apartment?
The lowest price for a Cheap One Bedroom Middlebury Apartment is $1,250 at 1243 W Main St.
What is the lowest price for a Cheap Two Bedroom Middlebury Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Middlebury is starting from $1,550 at Villa Square LLC.
What is the most affordable Middlebury Three Bedroom Apartment?
The best deal on a cheap Middlebury Three Bedroom Apartment rental is at Oxford Commons and starts from $1,950.
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
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!
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.