339 Main Street South, Woodbury, Connecticut

$699,900

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4

Beds

3

Baths

3,700

Square feet

1.39

Acres

About 339 Main Street South

Watch the parade from your front yard, walk to school, walk to the excellent restaurants in town, walk to the library and to the local park and market! Fabulous location! One of Woodbury's last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops, parks, and restaurants. The interior of the home boasts a rich history with exposed wooden beams, 4 fireplaces, and classic hardwood floors, creating an inviting and warm atmosphere. Outside, a private patio with an open fireplace provides an ideal setting for relaxation or entertaining, surrounded by lush perennial gardens. Adding to the property's versatility is a separate guest house. This additional structure is perfect for an artist's studio, offering a quiet and inspiring space for creative pursuits, or it can serve as a professional office. Woodbury is known for its historical properties, with some homes dating back to the late 17th century. Main Street offers a charming experience with its antique shops, local restaurants, and vibrant Memorial Day parades. Woodbury is known for its picturesque downtown area, featuring beautiful streets and historic houses. Litchfield Hills are home to numerous wineries, forming part of Connecticut's Wine Trail,where you can enjoy tastings and scenic vineyards. The region also boasts farm-to-table restaurants that highlight local produce

Features of 339 Main Street South

MLS® # 24165323
Price $699,900
Bedrooms 4
Bathrooms 3.00
Full Baths 2
Half Baths 1
Square Footage 3,700
Acres 1.39
Type Single Family For Sale
Style Colonial, Antique
Status Under Contract - Continue to Show

Community Information

Address 339 Main Street South
Area N/A
City Woodbury
County Litchfield
State Connecticut
Zip Code 06798

Amenities

Is Waterfront No
Waterfront Not Applicable
Has Pool No

Interior

Interior Features Cable - Available
Appliances Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
Heating Hot Air, Radiator, Zoned, Propane
Cooling Ceiling Fans, Central Air
Fireplace Yes
# of Fireplaces 4
Has Basement Yes
Basement Partial

Exterior

Exterior Clapboard
Exterior Features Shed, Garden Area, Guest House, Patio
Lot Description Level Lot, Historic District
Roof Shingle
Foundation Stone

School Information

Elementary Mitchell
High Nonnewaug

Additional Information

Date Listed April 9th, 2026
Days on Market 153
Zoning MSD
RE / Bank Owned No

Listing Details

OfficeBerkshire Hathaway NE Prop.

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Listing information last updated on September 10th, 2026 at 1:42pm EDT.