2 Bedroom Apartments for Rent in Woodbury, CT (37 Rentals)

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The Gardens
2 Bedroom Apartments

The Gardens

74 Main St NWoodbury, CT 06798
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1565 Main St N
2 Bedroom Apartments

1565 Main St N

1565 Main St NWoodbury, CT 06798
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346 Main St S
2 Bedroom Apartments

346 Main St S

346 Main St SWoodbury, CT 06798

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.

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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.

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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.

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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.

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Showing Results 1-37, Page 1 of 1

Woodbury, CT Local Guide

Largest Available Woodbury 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Woodbury, CT is found at Wyndham Court Apartments in the Waterbury Middlebury neighborhood and is 1,200 square feet priced from $1,495. 1243 W Main St has the second largest 2 Bedroom, which is sized at 1,200 square feet and currently listed start at $1,600. Here is today’s list of the largest available 2 Bedroom units in Woodbury:

Apartment ListingModel NameSquare FootagePriced From
Wyndham Court ApartmentsTwo Bedroom1,200 Sq Ft$1,495
1243 W Main St2 Bdrm1,200 Sq Ft$1,600
Federal Road ApartmentsTwo Bedroom 2.11,181 Sq Ft$2,592
Rivers EdgeThe Beacon1,100 Sq Ft$2,062
Middlebury Crossing Apartments2 Bedroom/1.5 Bath Townhome1,100 Sq Ft$1,850
West Hill ApartmentsTown Home with Full Basement1,020 Sq Ft$1,895
Parkview ApartmentsGramercy980 Sq Ft$1,875
Horizon Homes2-Bedroom944 Sq Ft$1,725
Villa Square LLC2 Bedroom Townhouse, New Kitchen925 Sq Ft$1,850
Ramblewood Apartments2 Beds, 1 Baths850 Sq Ft$1,750

Cheapest Available Woodbury 2 Bedroom Apartments

As of July 07, 2025 the lowest priced 2 Bedroom apartment unit in Woodbury, CT is the Two Bedroom Model starting from $1,315 at Bunker Hill in the Waterbury Middlebury neighborhood. The second most affordable Woodbury 2 Bedroom is the Two Bedroom One Bath Model at Diamond Court Apartments starting at $1,450 . The average price for all 2 Bedroom apartments in Woodbury is currently $2,104. Here is today’s list of the cheapest available 2 Bedroom options in Woodbury:

Apartment ListingModel NamePriced From
Bunker HillTwo Bedroom$1,315
Diamond Court ApartmentsTwo Bedroom One Bath$1,450
Wyndham Court ApartmentsTwo Bedroom$1,495
1243 W Main St2 Bdrm$1,600
Josephine Towers Senior Living2 Beds, 1 bath$1,622
Middlebury Crossing ApartmentsTwo Bedroom/ 1 Bath$1,650
Highland Ridge1B/2BD + Off WDHighland Ridge$1,650
Villa Square LLC2 Bedroom Ranch, New Kitchen$1,650
Horizon Homes2-Bedroom$1,725
Ramblewood Apartments2 Beds, 1 Baths$1,750

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Getting Around Woodbury, CT

Walk Score®

36 / 100

Car-Dependent

Most errands require a car

Bike Score®

20 / 100

Somewhat Bikeable

Minimal bike infrastructure

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 2 Bedroom Woodbury Apartments

What is the Cheapest apartment in Woodbury with 2 Bedroom?

Currently the most affordable 2 Bedroom in Woodbury is at Bunker Hill listed at $1,315.

How much is the average rent for a 2 Bedroom Woodbury Apartment?

The average rent for a 2 Bedroom Apartment in Woodbury is $2,104.

What is the largest available 2 Bedroom Woodbury Apartment for rent?

Today's apartment with the most square footage in Woodbury is a 1,200 square feet unit starting from $1,495 at Wyndham Court Apartments.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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The Art of the Rental Viewing: What to look for during a property tour

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.