
2 Bedroom Apartments for Rent in Woodbury, CT (41 Rentals)


533 Weekeepeemee Rd

107 Main St N

36 Washington Ave

33 Washington Ave

346 Main St S

1565 Main St N

36 Church St

Holly House Apartments

Terrace Apartments
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.

Spruce Bank Farm

The Gardens

A Place To Call home

Total Monthly Price
The Residences at Quarry Walk

Total Monthly Price
Federal Road Apartments

Total Monthly Price
Rivers Edge

Total Monthly Price
Lakeview

223 Meadow St

Total Monthly Price
Brookfield Village Apartments

Total Monthly Price
Parkview Apartments
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.

Trowbridge House Apartments

Total Monthly Price
Horizon Homes

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The Mews at Sandy Hook

Total Monthly Price
West Hill Apartments

Highland Ridge

Meridian Apartments

Middlebury Crossing Apartments

Scott Gardens Apartments

Overlook at Fort Hill Apartments

1243 W Main St
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.

Barton Commons

Josephine Towers Senior Living

Wyndham Court Apartments

667 S Britain Rd

576 Heritage Vlg

249 Woodbury Rd

17 Kirby Rd

Heritage Circle

Bunker Hill

Ramblewood Apartments
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.

25 Church St
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 | $1,535 | $1,085 | $2,180 |
| Woodbury 1 Bedroom Apartments | $1,778 | $950 | $2,770 |
Woodbury 2 Bedroom Apartments | $2,234 | $1,595 | $3,840 |
| Woodbury 3 Bedroom Apartments | $2,271 | $1,600 | $3,850 |
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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. The Residences at Quarry Walk in the Seymour Naugatuck Ansonia neighborhood has the second largest 2 Bedroom, which is sized at 1,414 square feet and currently listed start at $3,840. 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 |
| The Residences at Quarry Walk | A2 | 1,414 Sq Ft | $3,840 |
| Brookfield Village Apartments | Two Bed Two Bath Loft 1256 | 1,256 Sq Ft | $3,400 |
| A Place To Call home | B3-2X1.5TH | 1,210 Sq Ft | $2,650 |
| Wyndham Court Apartments | Two Bedroom | 1,200 Sq Ft | $1,595 |
| 1243 W Main St | 2 Bdrm | 1,200 Sq Ft | $1,600 |
| Federal Road Apartments | Two Bedroom 2.1 | 1,181 Sq Ft | $3,030 |
| Middlebury Crossing Apartments | 2 Bedroom/1.5 Bath Townhome | 1,100 Sq Ft | $1,995 |
| Lakeview | The Kingsbury | 1,080 Sq Ft | $1,761 |
| The Mews at Sandy Hook | 2 Beds, 2 baths | 1,000 Sq Ft | $2,925 |
Cheapest Available Woodbury 2 Bedroom Apartments
As of April 09, 2026 the lowest priced 2 Bedroom apartment unit in Woodbury, CT is the Two Bedroom Model starting from $1,595 at Wyndham Court Apartments in the Waterbury Middlebury neighborhood. The second most affordable Woodbury 2 Bedroom is the 2 Bdrm Model at 1243 W Main St starting at $1,600 . The average price for all 2 Bedroom apartments in Woodbury is currently $2,234. Here is today’s list of the cheapest available 2 Bedroom options in Woodbury:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Wyndham Court Apartments | Two Bedroom | $1,595 |
| 1243 W Main St | 2 Bdrm | $1,600 |
| Josephine Towers Senior Living | 2 Beds, 1 bath | $1,622 |
| Trowbridge House Apartments | 2 Bedroom | $1,650 |
| West Hill Apartments | Townhome Bldg 5 | $1,700 |
| Scott Gardens Apartments | 2 Bedroom Townhouse | $1,725 |
| Lakeview | The Atwood | $1,739 |
| Middlebury Crossing Apartments | Two Bedroom/ 1 Bath | $1,745 |
| Ramblewood Apartments | 2 Beds, 1 Baths | $1,750 |
| 223 Meadow St | 2Beds | $1,850 |
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
Read ArticleDon'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.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
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Read ArticleCash 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.
Read ArticleQuick 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.
Best Local Schools in Woodbury, CT
School data provided by Great Schools
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Woodbury, CT Rentals by Map
See the most popular apartments and homes in Woodbury, CT
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 Wyndham Court Apartments listed at $1,595.
How much is the average rent for a 2 Bedroom Woodbury Apartment?
The average rent for a 2 Bedroom Apartment in Woodbury is $2,234.
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 2,145 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

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.

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.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.