
2 Bedroom Apartments for Rent in Woodbury, CT (54 Rentals)


13 Pleasant St

300 Railtree Hill Rd

48 White Oak Rd

4-5 Weekeepeemee Rd

54 Clubhouse Dr

47 Terrell Rd

36 Church St

1565 Main St N

346 Main St S
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Looking for the perfect new rental? Learn great ways to spot the perfect apartment for you, identify common red flags, and avoid rental issues and scams with these expert provided actionable tips.

Holly House Apartments

Terrace Apartments

Spruce Bank Farm

The Gardens

Trowbridge House Apartments

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Beacon Mill Village

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The Residences at Quarry Walk

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Overland Crossing

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Federal Road Apartments

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Rivers Edge Apartments
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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Marin Village

Taunton Residences at Deep Brook

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Lakeview

223 Meadow St

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Covered Bridge

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Brookfield Village Apartments

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Parkview

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West Hill Apartments

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The Mews at Sandy Hook

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Horizon Homes
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

Middlebury Crossing Apartments

Scott Gardens Apartments

Meridian Apartments

Highland Ridge

Villa Square LLC

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Barton Commons

Summit Ridge Estates

Platform at Naugatuck

Overlook at Fort Hill Apartments

Barnbeck Place
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Wyndham Court Apartments

1243 W Main St

158 Martone St

184 Kaynor Dr

140 Woodvale Dr

342 Heritage Vlg

61 Far View Cmns

17 Kirby Rd

Heritage Circle

Bunker Hill
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.
Woodbury, CT Local Guide

How much does it cost to rent an apartment in Woodbury?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Woodbury Studio Apartments | $1,778 | $1,150 | $2,420 |
| Woodbury 1 Bedroom Apartments | $2,197 | $950 | $2,838 |
Woodbury 2 Bedroom Apartments | $2,560 | $1,595 | $3,750 |
| Woodbury 3 Bedroom Apartments | $2,477 | $2,075 | $3,625 |
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Woodbury, CT Local Guide
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Largest Available Woodbury 2 Bedroom Apartments
The largest available 2 Bedroom apartment unit in Woodbury, CT is found at 223 Meadow St in the The Village at Oxford Greens neighborhood and is 1,500 square feet priced from $1,850. Covered Bridge in the Hawleyville neighborhood has the second largest 2 Bedroom, which is sized at 1,327 square feet and currently listed start at $3,239. Here is today’s list of the largest available 2 Bedroom units in Woodbury:
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| 223 Meadow St | 2Beds | 1,500 Sq Ft | $1,850 |
| Covered Bridge | The Sycamore | 1,327 Sq Ft | $3,239 |
| The Residences at Quarry Walk | B1 | 1,260 Sq Ft | $3,155 |
| Barnbeck Place | B4 | 1,240 Sq Ft | $2,840 |
| Beacon Mill Village | B3-2X1.5TH | 1,235 Sq Ft | $2,660 |
| Wyndham Court Apartments | Two Bedroom | 1,200 Sq Ft | $1,700 |
| 1243 W Main St | 2 Bdrm | 1,200 Sq Ft | $1,600 |
| Federal Road Apartments | Two Bedroom 2.1 | 1,181 Sq Ft | $3,075 |
| Middlebury Crossing Apartments | 2 Bedroom/1.5 Bath Townhome | 1,100 Sq Ft | $1,995 |
| Taunton Residences at Deep Brook | Two Bed Two Bath | 1,040 Sq Ft | $3,230 |
Cheapest Available Woodbury 2 Bedroom Apartments
As of August 24, 2026 the lowest priced 2 Bedroom apartment unit in Woodbury, CT is the 2 Bdrm Model starting from $1,600 at 1243 W Main St in the Waterbury Middlebury neighborhood. The second most affordable Woodbury 2 Bedroom is the 1B/2BD Highland Ridge Model at Highland Ridge starting at $1,650 in the Waterbury neighborhood. The average price for all 2 Bedroom apartments in Woodbury is currently $2,560. Here is today’s list of the cheapest available 2 Bedroom options in Woodbury:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| 1243 W Main St | 2 Bdrm | $1,600 |
| Highland Ridge | 1B/2BD Highland Ridge | $1,650 |
| Wyndham Court Apartments | Two Bedroom | $1,700 |
| Scott Gardens Apartments | 2 Bedroom Townhouse | $1,725 |
| Middlebury Crossing Apartments | Two Bedroom/ 1 Bath | $1,745 |
| Ramblewood Apartments | 2 Beds, 1 Baths | $1,750 |
| Villa Square LLC | 2 Bedroom Townhouse, Cinch | $1,800 |
| Lakeview | The Ashford II | $1,801 |
| 223 Meadow St | 2Beds | $1,850 |
| West Hill Apartments | Town Home with Full Basement | $1,875 |
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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Best Local Schools in Woodbury, CT
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Remember the 3 Rules of Real Estate:Location, Location, Location!
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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 1243 W Main St listed at $1,600.
How much is the average rent for a 2 Bedroom Woodbury Apartment?
The average rent for a 2 Bedroom Apartment in Woodbury is $2,560.
What is the largest available 2 Bedroom Woodbury Apartment for rent?
Today's apartment with the most square footage in Woodbury is a 1,500 square feet unit starting from $1,850 at 223 Meadow St.
What is the average size for Woodbury 2 Bedroom Apartments for rent?
The average size for a 2 Bedroom rental in Woodbury is currently 1,557 sq ft.
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

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.