Date
Details
Price
Change
Source
8/10/2026
Listed
$4,800
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/35
$4,800 Just Listed
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/35
Property Description
Expansive main house with frontage on quintessential historic Main Street. RESIDENTIAL or COMMERCIAL space! Walk the sidewalks to the antique shops, parks, & restaurants. Enjoy the wineries and farm markets. Have a front row seat for the summer parades and the Christmas Eve luminaries that adorn Main Street. Deep lot with ample parking in the rear of the house. All four bedrooms have en-suite bathrooms making this a perfect residence for an extended family or roommate situation. This vintage home has been well cared for throughout the years and has tons of charm blended with modern updates. House was utilized as an AirBNB so the furniture in the photos can stay or go depending on your needs. This house is zoned as such that it can also be used for offices. Ideal for a law firm, insurance company, real estate office, etc. HOUSE CAN ALSO BE RENTED IN CONJUNCTION WITH THE COMMERCIAL BARN as seen in MLS #24196999 for $6,500 total. Run your business without having to commute to work! Many opportunities at this location so please inquire with your business or residential needs.
Full Property Details
Full Property Details for 259 Main St S
General
- Rent: $4,800
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24197395
- Updated: 8/10/2026
- Added to Site: 2 day(s) ago
Rental Information
- Rental Type: Yearly Unfurnished, Yearly Furnished
- Lease Terms: Per Month
Interior
- Number of Rooms: 8
- Fireplace: Yes
- Number of Fireplaces: 1
- Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 4
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
- Primary Bedroom: Primary Bedroom - Full Bath, Upper
- Bedroom 1: Bedroom - Full Bath, Upper
- Bedroom 2: Bedroom - Full Bath, Upper
- Bedroom 3: Bedroom - Full Bath, Upper
Other Rooms
- Living Room: Living Room, Main
- Family Room: Family Room, Main
- Kitchen: Kitchen, Main
- Formal Dining Room: Formal Dining Room, Main
- Laundry: Upper Level
Exterior
- Exterior Features: Sidewalk, Porch, Garden Area
- Color: grey
Parking
- Total Spaces: 19
- Parking: Parking Lot, Off Street Parking
Location
- County: Litchfield
- Driving Directions: Main Street South next to municipal buildings
School Information
- Elementary School: Mitchell
- High School: Nonnewaug
Community
- Pets Allowed: Yes
- Pet Restrictions: At owner's discretion
Heating & Cooling
- Cooling Type: Wall Unit, Window Unit
- Heating Type: Hot Air, Natural Gas
- Heating Fuel: Natural Gas
- Water Heater: Domestic
Utilities
- Sewer: Septic, Shared Septic
- Water: Public Water Connected
Structural Information
- Architectural Style: Colonial
- Construction Status: No/Resale
- Basement Desc.: Full, Storage
- Attic: Yes
- Square Feet: 3,200
- Above Ground: 3,200 Sq. Ft.
- Year Built: 1780
Lot Features
- Lot Size (Acres): 1
- Zoning: MSD
- Lot Description: Sloping Lot, Historic District
Financial Considerations
- Tenant Pays: All Utilities
Disclosures and Reports
- Exclusions: Furnishings can stay or go.
- Property ID: 936191
Listed by Gina Jacobs Real Estate, Gina Baumann-Jacobs
Price History for 259 Main St S
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Apartment
- Active
- Updated 5 days ago
- 3Beds
- 1Total Bath
- 1,400Sq. Ft.
- Condo
- Active
- Updated 1 day ago
- 3Beds
- 2Total Baths
- 1,716Sq. Ft.
- Single Family
- Active
- Updated 4 days ago
- 2Beds
- 1Total Bath
- 1,204Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Active
- Updated 11 hours ago
- 5Beds
- 3Total Baths
- 3,424Sq. Ft.
- Apartment
- Active
- Updated 15 hours ago
- 4Beds
- 2Total Baths
- 3,156Sq. Ft.
- Apartment
- Active
- Updated 6 days ago
- 2Beds
- 1Total Bath
- 912Sq. Ft.
259 Main Street South, Woodbury, CT 06798 (MLS# 24197395) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 259 Main Street South is currently listed for rent at $4,800 and was received on August 10, 2026. Want to learn more about 259 Main Street South? Do you have questions about finding other real estate for sale or rent in Woodbury? You can browse all Woodbury rentals or contact a Coldwell Banker agent to request more information.