339 Main Street SouthWoodbury, CT 06798

Single Family · 4 Beds · 2 Full Baths · 1 Half Bath · 3,700 Sq. ft. | 1.39 Acres
$874,900 Active

339 Main Street South Overview

Time on Site:
81 days

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, providing a dedicated work environment. 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. As a gateway to the Litchfield Hills, the area provides access to a wider region known for its natural beauty and diverse attractions. 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.

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339 Main Street South Facts & Features

  • Type Single Family
  • Sq. ft. 3,700
  • Price/Sq.ft. $236
  • Lot 1.39 Acres

Details

General

Association/HOA

  • Association: No

School Information

  • Elementary School: Mitchell
  • High School: Nonnewaug

Listing Information

  • Bank Owned Property: No
  • Potential Short Sale: No

Building Information

  • Year Built: 1691

Location/Region

  • County Or Parish: Litchfield
  • Neighborhood: N/A

Building Exterior/Construction

  • New Construction Type: No/Resale

Community/Development

  • Community Features: Golf Course, Health Club, Library, Medical Facilities, Park, Private School(s), Public Rec Facilities, Stables/Riding

Tax Information

  • Tax Annual Amount: $10,526.00
  • Tax Year: July 2025-June 2026

General Information

  • Parcel Number: 936203
  • Property Type: Single Family For Sale
  • Zoning: MSD

Interior

Beds/Baths

  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms Total: 3
  • Bedrooms Total: 4

Building Interior

  • Attic Description: Finished, Walk-up
  • Attic: Yes
  • Fuel Tank Location: In Ground
  • Heat Fuel Type: Propane
  • Hot Water Description: Upright Tank
  • In Law Apartment: Yes
  • Laundry Room Info: Main Level
  • Rooms Additional: Laundry Room, Mud Room, Workshop

General Information

  • Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Basement: Partial
  • Cooling: Ceiling Fans, Central Air
  • Fireplaces Total: 4
  • Foundation Details: Stone
  • Heating: Hot Air, Radiator, Zoned
  • Interior Features: Cable - Available
  • Living Area: 3700

Exterior

Lot Information

  • Lot Features: Level Lot, Historic District
  • Lot Size Acres: 1.39
  • Lot Size Source: Public Records
  • Water Source: Public Water Connected

Waterfront/View

  • Waterfront Features: Not Applicable
  • Waterfront: No

Building Exterior/Construction

  • Architectural Style: Colonial, Antique
  • Construction Materials: Clapboard
  • Roof: Shingle

General Information

  • Exterior Features: Shed, Garden Area, Guest House, Patio
  • Pool Private: No
  • Sewer: Septic

Room Information

Room: Dining Room

  • Level: Main
  • Length: 16
  • Width: 14
  • Description: Beams,Fireplace,Hardwood Floor

Room: Family Room

  • Level: Main
  • Length: 18
  • Width: 18
  • Description: Hardwood Floor

Room: Kitchen

  • Level: Main
  • Length: 19
  • Width: 11
  • Description: Beams,Pantry,Tile Floor

Room: Living Room

  • Level: Main
  • Length: 32
  • Width: 13
  • Description: Fireplace,Hardwood Floor

Room: Bedroom

  • Level: Upper
  • Length: 23
  • Width: 12
  • Description: Hardwood Floor

Room: Bedroom

  • Level: Upper
  • Length: 12
  • Width: 12
  • Description: Hardwood Floor

Room: Bedroom

  • Level: Upper
  • Length: 33
  • Width: 16
  • Description: Cathedral Ceiling,Beams,Bedroom Suite,Hardwood Floor

Room: Primary Bedroom

  • Level: Upper
  • Length: 20
  • Width: 13
  • Description: Fireplace,Hardwood Floor

Room: Rec/Play Room

  • Level: Upper
  • Length: 23
  • Width: 12

339 Main Street South Monthly Cost

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

339 Main Street South Market Data

Based on the last 30 days in this zip code

$744,818
Average List Price
$314
Average Price per Square Foot
0
Properties Sold
78
Average Days on Market
65
Properties for Sale
Calculations provided by Reliance Network

339 Main Street South History

Date Event Value Agent
4/9/2026Source: Smart MLS Added to Database
April 09, 2026
Listing provided courtesy of Berkshire Hathaway NE Prop.- MLS# 24165323MLS ProviderContact Information: (203) 228-0393