Zumper

259 Main St S
259 Main St S, Woodbury, CT 06798, USA

Condo for rent
Pet friendly
Monthly rent
$1,850–$4,950The price shown reflects a 12-month lease. Fees may apply.
Beds1–4
Baths1–4
Sqft1,000–7,112
modified
5+ Days Ago

Property Overview

Located in Woodbury, this property features a cozy fireplace, ample closet space, and beautiful outdoor areas, including a private courtyard. It is conveniently situated near top-rated schools and offers pet-friendly amenities with various nearby services for pets. With a strong value per square foot and an extensive photo gallery, it presents a compelling option for those seeking comfort and accessibility in a desirable location.

This summary uses Zumper’s proprietary data. “Things you’ll love” and “Great for” are based on our internal analyses of market trends and renter insights.

Things you’ll love

  • Elementary school nearby
  • Middle school nearby
  • More space

Great for

  • Pet owners

Highlights

  • Pet Friendly
  • fireplace
  • ample closet space
  • laundry room
  • spacious bedroom
  • private courtyard
  • beautiful outdoor space

Units

259 Main St S Woodbury, CT

Available

4

1 Bed

1 Bath

$1,850

Listed on 12/03/2025
Listed by JAG Real Estate Group
Days on market: 48
Property Id: 2072922 Light and bright 2 Story 1 Bedroom Condo available for immediate occupancy. This unit comes with a spacious and open first floor lay out, kitchen with extra cabinet space and more. The second floor has a full bathroom and spacious Bedroom with ample closet space. This condo is located on Woodbury most desirable areas and will not last long so dont wait schedule a tour today!

Available

4 Beds, 4.5 Baths

4 Beds

4.5 Baths

$4,950

Listed on 08/04/2025
Listed by JAG Real Estate Group
Days on market: 170
Property Id: 1500786 Located on Main Street South in the heart of Woodbury, in the Litchfield Hills this main house offers 4 BR, 4.5 baths and features original architectural elements, ample living space and beautiful outdoor space. The main living area has a half bath, EIK with island, SS appliances and door to side deck for outdoor eating and grilling + private courtyard, professionally landscaped. There is a front living room w/FP and two other rooms for additional living space. Upstairs there is a laundry room and 4 bedrooms all with their own on-suite full bath. There is also third floor, unfinished attic space. Great location, within walking distance of great restaurants and shops and just across the street from the bank and grocery store. Possible large garage/storage area for lease.

Occupied Units

Occupied

1

1 Bed

1 Bath

$1,850

Listed by Mike Baldwin
Days on market: 295
Property Id: 1559754 Gorgeous one-bedroom, townhouse style unit available in the elemental gardens property. This property boasts picturesque grounds and landscaping that provide tranquility with the many commercial amenities of Woodbury close by. Inside of the unit is a spacious two-level living area that is comfortable and move in ready. Take a look today, this won't last long!

Amenities for 259 Main St S

Some units at this address have these amenities. View unit details for more information.

Building
  • Dogs Ok
  • Cats Ok
  • Garage Parking
  • Outdoor Space
  • Storage
  • On-Site Laundry
Unit Amenities
  • On-Site Laundry
  • Hardwood Floor
  • Carpet
  • In-Unit Laundry
  • Dishwasher
  • Fireplace
  • Outdoor Space

Policies at 259 Main St S

Applicants

Applicants

One-time.

Contact Property

REQUIRED FEES

Security Deposit

One-time. Refundable.

Contact Property

Parking Policy

Garage Parking

Dog Policy

Allowed

Cat Policy

Allowed

Contact for more information on pet policy.

Questions about this property’s policies and fees?

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About 259 Main St S

HomeApartments in Woodbury 259 Main Street South #4, Woodbury, Connecticut 06798, United States

Check out 259 Main St S in Woodbury, CT, a charming property offering a unique living experience. This intimate community consists of 3 units, with spacious 1 and 4-bedroom options ranging from 1000 to 7112 square feet. Residents can enjoy a range of amenities, including hardwood floors, high-speed internet, and in-unit laundry. Cozy up by the fireplace or take in the beautiful outdoor space, complete with a private courtyard and professionally landscaped grounds. Additional perks include ample closet space, oven, dishwasher, garage, and on-site storage. As a pet-friendly property, you can bring your furry friend along. With its long-term rentals, this property is perfect for those looking for a stable and comfortable living situation.

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Address details

Units3
Units available2
City
Zip code06798

259 Main Street South #4 is great for:

Pet owners

  • Outdoor spaces are available at this property
  • 2 pet grooming services nearby
  • 5 pet supply stores near the property
  • 1 pet hospital in the area

Property highlights

We compared every listing in the surrounding area to determine which amenities are most common. If a building lacks an amenity that most others in the area have, it is a con. If a building has an amenity most others in the area do not, it is a pro. Similarly, price, schools, and size are calculated relative to the size, price, and distance to schools of the other properties nearby.

How 259 Main St S, Woodbury, CT 06798, USA compares to other nearby properties.

Positives

Elementary school nearby
There is an elementary school 0.4 mile away
Middle school nearby
There is a middle school 0.5 mile away
More space
The 4-bedroom is 2208 sqft larger than other listings nearby
High school nearby
There is a high school 1 mile away
Extra Storage
Upgraded in-unit features
Images available
There are at least 10 photos of this address
Pet friendly
Rentals at this address allow pets

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Rent trends in Woodbury

1-bedroom apartments here are priced 3% lower than 1-bedrooms in Woodbury.

4-bedroom apartments at 259 Main Street South #4 cost about 10% more than the average rent price for 4-bedroom apartments in Woodbury.

Median rents as of Jan 17 2026.
Woodbury
A table of 1-bedroom apartment rental data trends in Woodbury
MonthMedian Rent
September 2024$1,787
October 2024$1,775
March 2025$1,750
April 2025$1,849
May 2025$1,850
December 2025$1,899
January 2026$1,899

Affordability calculator

Can I afford to live at 259 Main St S?

Bedrooms

Rent-to-income ratio

30%

Slide to adjust the percentage of your monthly income you are willing to spend on rent.
The general rule of thumb is to spend around 30% or less of your income on rent.
Recommended income

$74,000/yr

With your selected rent-to-income ratio, you'd ideally want to make $74,000 annually to afford this 1-bedroom monthly rent price of $1,850.
For more information on rent affordability, visit our rent calculator.

Rent history

The increase or decrease in monthly rent compared to the previous listing price.
Check out the past listing prices for monthly rent at 259 Main Street South, Woodbury, CT.
1 year ago$1,7501 bed1 bath
1 year ago$6,7504 bed4.5 bath

Schools near 259 Main Street South #4

Mitchell Elementary School

14 school st

woodbury, CT, 6798

PK, K-5Public
B+

Bethlehem Elementary School

92 east st

bethlehem, CT, 6751

PK, K-5Public
B+
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Getting around Woodbury near 259 Main St S

Walking

3/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).

Driving

10/10
Commuting is easy with multiple accessible routes and plenty of parking.

Cycling

2/10
This is semi-bikeable, but you’ll need another way of getting around.

Points of interest for 259 Main St S, Woodbury

Groceries

8/10
At least one grocery store within a few minutes' walk

Shopping

3/10
Some shops within walking distance

Cafes

0/10
Few or no cafés within walking distance

Restaurants

4/10
Some restaurants within walking distance

Primary schools

9/10
At least one elementary school within a 10-minute walk

High schools

8/10
At least one high school within a 20-minute walk

Nightlife

0/10
Few or no bars within walking distance

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