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339 Main Street South

Woodbury, Connecticut 06798

ACTIVE$874,900
Beds
4
Baths
2 | 1
SqFt
3,700
Acres
1.39
Year Built
1691
Matt Caiola

Matt Caiola

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Guest House4 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,630

per 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

Homes with a close match in area, property type, and price.

Listed By

Marian Van Egas

(203) 228-0393

Berkshire Hathaway NE Prop.

(203) 264-2880

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.