About 259 Main Street South
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.
Features of 259 Main Street South
| MLS® # | 24197395 |
|---|---|
| Price | $4,800 |
| Bedrooms | 4 |
| Bathrooms | 5.00 |
| Full Baths | 4 |
| Half Baths | 1 |
| Square Footage | 3,200 |
| Acres | 1.00 |
| Type | Residential Rental |
| Sub-Type | Single Family Rental |
| Style | Colonial |
| Status | Active |
Community Information
| Address | 259 Main Street South |
|---|---|
| Area | N/A |
| City | Woodbury |
| County | Litchfield |
| State | Connecticut |
| Zip Code | 06798 |
Amenities
| Parking Spaces | 19 |
|---|---|
| Parking | Parking Lot, Off Street Parking |
| Is Waterfront | No |
| Waterfront | Not Applicable |
| Has Pool | No |
Interior
| Appliances | Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer |
|---|---|
| Heating | Hot Air, Natural Gas |
| Cooling | Wall Unit, Window Unit |
| Fireplace | Yes |
| # of Fireplaces | 1 |
| Has Basement | Yes |
| Basement | Full, Storage |
Exterior
| Exterior Features | Sidewalk, Porch, Garden Area |
|---|---|
| Lot Description | Sloping Lot, Historic District |
School Information
| Elementary | Mitchell |
|---|---|
| High | Nonnewaug |
Additional Information
| Date Listed | August 10th, 2026 |
|---|---|
| Days on Market | 31 |
| Zoning | MSD |
| RE / Bank Owned | No |
Listing Details
| Office | Gina Jacobs Real Estate |
|---|