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1917 Main Street North

Woodbury, Connecticut 06798

ACTIVE$780,000

Reduced from $865,000

Beds
4
Baths
2
SqFt
4,819
Acres
5.91
Year Built
1854
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Waterfront3 FireplacesPrice Reduced

About This Home

Built in 1854, this 5.91 acre property offers an incredible value impossible to replicate today for the price. The property includes an Italianate stone home with an approx 675 sq foot retail/office room with a separate entrance at the driveway, a 28' x 53' post and beam barn with a full walkout lower level, a large pond, stone walls, incredible perennial garden surround, and a 21' x 45' accessory building with heat - great guest house or in-law potential. Inspired by Tuscan villas, Italianate style homes, usually square and symmetrical, were popular in the late 19th C. in New England. Park-like grounds; large pond has goldfish (see pics). The 3532 square foot main home has potential for an in-home business, or retail shop as it once was. Other potential uses in this highly-visible location include using the barn for farm animals and/or horses. Home has 4 bedrooms, 2 full bathrooms, 3 fireplaces, and approx 435 sq foot foot, renovated, eat-in, sunny kitchen with leathered granite counters and stainless appliances. New oil furnace 2026. Septic recently maintained (new pump, piping, and floats in 2022 by Garrity, no problems since). 50 gallon water heater Oct 2022. Substantial moldings and built-ins, front and back staircases, specialty stainless skylights, and a rooftop belvedere, which looks beautiful lit up at night, atop the well maintained copper roof. Minutes to three towns centers of Woodbury, Watertown, and Bethlehem. Guesthouse has elec.

Key Facts

City/Town
Woodbury
Neighborhood
North Woodbury
Property / Style
Single Family · Antique,European
Year Built
1854
Days on Market
151 days
Beds
4
Baths
2 full
Living Area
4,819 sq ft
Lot Size
5.91 acres
Garage / Parking
10 total
Property Taxes
$10,450 / Annually

Market Snapshot

The Woodbury Market

Single Family · trailing 12 months

Median Days on Market

62

34 active listings

Median $ / Sq Ft

$322

34 active listings

Sale-to-List Ratio

99.5%

93 sales

How this home compares

List Price

$780,000

vs $799,950 median

In line with median

Price / Sq Ft

$162

vs $322 median

49.7% below median

Days on Market

151 days

vs 62 days median

89 days longer than median

Based on 34 active and 93 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of November 13, 2026.

Location

1917 Main Street North, Woodbury, Connecticut

Property + 11 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,329

per month

  • Principal & Interest$4,198
  • Property Taxes$871
  • Insurance$260
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Woodbury
Neighborhood
North Woodbury
County
Litchfield

Residence

Property Type
Single Family
Style
Antique,European
Year Built
1854
New Construction
No/Resale
Living Area
4,819 sq ft
Below Grade
1,296 sq ft

Schools

Elementary
Mitchell
High
Nonnewaug

Interior

Heating
BaseboardHot Air
Heat Fuel
ElectricOil
Cooling
None
Fireplaces
3
Laundry
Main Level
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryerWine Chiller
Basement
FullUnfinished
In-Law Apartment
PossibleDetached
Interior Features
Security System
Additional Rooms
FoyerMud RoomWorkshop

Exterior & Lot

Lot Size
5.91 acres
Zoning
OS100
Garage / Parking
10 total parking spacesDrivewayPrivateAsphalt
Waterfront
Direct waterfront
Waterfront Details
PondBrookWalk to WaterViewAccess
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
StoneWood
Color
Stone
Roof
FlatMetal
Foundation
ConcreteStone
Exterior Features
ShedBarnDeckLightingStone Wall
Lot Description
Farm LandClearedOpen Lot

Listing & Financials

Property Taxes
$10,450 / Annually
Days on Market
151
MLS #
24183601
MLS Status
Active

Similar Properties

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

Listed By

Amy Lapierre

(203) 903-1950

Coldwell Banker Realty

(860) 393-0087

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 11/13/2026. 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 11/13/2026 at 2:55 AM UTC.