1917 Main Street North
Woodbury, Connecticut 06798
Reduced from $865,000
- Beds
- 4
- Baths
- 2
- SqFt
- 4,819
- Acres
- 5.91
- Year Built
- 1854
- Neighborhood
- North Woodbury
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
34
15 under contract
Median List Price
$799,950
34 active listings
Median Closed Price
$600,000
93 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 12, 2026per 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
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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 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.