339 Main Street South
Woodbury, Connecticut 06798
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 3,700
- Acres
- 1.39
- Year Built
- 1691
- Property Type
- Single Family

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About This Home
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.
Key Facts
- City/Town
- Woodbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial,Antique
- Year Built
- 1691
- Days on Market
- 110 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 3,700 sq ft
- Lot Size
- 1.39 acres
- Property Taxes
- $10,526 / Annually
Market Snapshot
The Woodbury Market
Single Family · trailing 12 months
Active Listings
26
26 under contract
Median List Price
$834,450
26 active listings
Median Closed Price
$587,500
88 sales
Median Days on Market
45
26 active listings
Median $ / Sq Ft
$302
26 active listings
Sale-to-List Ratio
99.0%
88 sales
How this home compares
List Price
$874,900
vs $834,450 median
In line with median
Price / Sq Ft
$236
vs $302 median
21.9% below median
Days on Market
110 days
vs 45 days median
65 days longer than median
Based on 26 active and 88 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of July 28, 2026.
Location
339 Main Street South, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,461
- Property Taxes$877
- Insurance$292
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodbury
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial,Antique
- Year Built
- 1691
- New Construction
- No/Resale
- Living Area
- 3,700 sq ft
Schools
- Elementary
- Mitchell
- High
- Nonnewaug
Interior
- Heating
- Hot AirRadiatorZoned
- Heat Fuel
- Propane
- Cooling
- Ceiling FansCentral Air
- Fireplaces
- 4
- Laundry
- Main Level
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- Partial
- In-Law Apartment
- YesDetached
- Interior Features
- Cable - Available
- Additional Rooms
- Laundry RoomMud RoomWorkshop
Exterior & Lot
- Lot Size
- 1.39 acres
- Zoning
- MSD
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Construction
- Clapboard
- Roof
- Shingle
- Foundation
- Stone
- Exterior Features
- ShedGarden AreaGuest HousePatio
- Lot Description
- Level LotHistoric District
Listing & Financials
- Property Taxes
- $10,526 / Annually
- Days on Market
- 110
- MLS #
- 24165323
- MLS Status
- Active
- Financing
- FHA,VA
Similar Properties
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/28/2026 at 6:10 AM UTC.