Homes for Rent in Middlebury, CT Under $2,000 (16 Rentals)

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property at 14 Wildwood Ave

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

4 Bedroom, 1.5 Bath Home for Rent

Available Now

14 Wildwood Ave

WaterburyCT06710
property at 8 Burma Rd

$2,000

Plus Fees

1 Bedroom, 1 Bath Home for Rent

Available Now

8 Burma Rd

SouthburyCT06488
property at 155 Tracy Ave

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

3 Bedroom, 1 Bath Home for Rent

Available Now

155 Tracy Ave

WaterburyCT06706
property at 58 High St

$1,825

Total Monthly Price

Total Monthly Price

Base Rent
$1,825

Total Monthly Price
$1,825

2 Bedroom, 1 Bath Home for Rent

Available Now

58 High St

WaterburyCT06704
property at 10 Wood St

$1,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,800

Total Monthly Price
$1,800

3 Bedroom, 1 Bath Townhome for Rent

Available Now

10 Wood St

WaterburyCT06704

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.

property at 585 Park Rd

$1,750

Total Monthly Price

Total Monthly Price

Base Rent
$1,750

Total Monthly Price
$1,750

2 Bedroom, 1.5 Bath Condo for Rent

Available Now

585 Park Rd

WaterburyCT06708
property at 585 Park Rd

$1,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,750

Total Monthly Price
$1,750

2 Bedroom, 1.5 Bath Condo for Rent

Available Now

585 Park Rd, Unit 3-8

585 Park Rd
WaterburyCT06708
property at 925 Oronoke Rd

$1,700

Total Monthly Price

Total Monthly Price

Base Rent
$1,700

Total Monthly Price
$1,700

2 Bedroom, 1 Bath Condo for Rent

Available Now

925 Oronoke Rd

WaterburyCT06708
property at 240 Scott St

$1,600

Plus Fees

2 Bedroom, 1 Bath Condo for Rent

Available Now

240 Scott St

NaugatuckCT06770

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

property at 15 Pilgrim Trail

$1,595

Total Monthly Price

Total Monthly Price

Base Rent
$1,595

Total Monthly Price
$1,595

1 Bedroom, 1 Bath Condo for Rent

Available Now

15 Pilgrim Trail

WoodburyCT06798
property at 259 Grove St

$1,500

Total Monthly Price

Total Monthly Price

Base Rent
$1,500

Total Monthly Price
$1,500

3 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

259 Grove St

WaterburyCT06710
property at 134 Charles St

$1,200

Total Monthly Price

Total Monthly Price

Base Rent
$1,200

Total Monthly Price
$1,200

2 Bedroom, 1 Bath Condo for Rent

Available Now

134 Charles St

WaterburyCT06708

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

property at 68 Adelaide Ave

$1,000

Total Monthly Price

Total Monthly Price

Base Rent
$1,000

Total Monthly Price
$1,000

1 Bedroom, 1 Bath Home for Rent

Available Now

68 Adelaide Ave

WaterburyCT06708

Middlebury, CT Local Guide

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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Cash 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.

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Quick 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.

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Middlebury, CT Rentals by Map

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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

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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.

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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.

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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.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate!