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36 Main Street South

Woodbury, Connecticut 06798

COMING SOON - NEW$595,000
Beds
3
Baths
2 | 1
SqFt
1,909
Acres
0.37
Year Built
1800
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 Fireplace

About This Home

Step into timeless charm with this classic 1800 New England Colonial in historic Woodbury. Thoughtfully curated wallcoverings weave subtle, boutique elegance and modern personality throughout. The main level offers a bright kitchen with under-cabinet lighting and tiled backsplash, plus space to eat in or host just steps away in the formal dining room. Conveniently situated in the kitchen is a stylishly remodeled half bath featuring marble tile floors. Unwind in the large living room complete with fireplace and built-in bookshelves, or retreat to the freshly remodeled den or home office perfectly positioned off the living and dining rooms. A cozy screened-in porch completes the level. The second floor hosts three bedrooms and two full bathrooms, highlighted by an available ensuite primary retreat. Above, a fully finished, heated third-floor attic offers versatile bonus space with hardwood floors-ideal for a dedicated workout room, play room, or guest suite. Head to the attached two-car garage through a sunlit mudroom, which opens directly to the private back patio and flat, fenced-in backyard. Enjoy unbeatable village convenience with town sidewalk access leading directly to grocery stores, the post office, great restaurants, and the library. A perfect blend of antique character and modern everyday living.

Key Facts

City/Town
Woodbury
Neighborhood
N/A
Property / Style
Single Family · Colonial,Antique
Year Built
1800
Days on Market
0 days
Beds
3
Baths
2 full · 1 half
Living Area
1,909 sq ft
Lot Size
0.37 acres
Garage / Parking
2 garage · 4 total
Property Taxes
$7,888 / Annually

Market Snapshot

The Woodbury Market

Single Family · trailing 12 months

Median Days on Market

67

33 active listings

Median $ / Sq Ft

$312

33 active listings

Sale-to-List Ratio

99.7%

94 sales

How this home compares

List Price

$595,000

vs $780,000 median

23.7% below median

Price / Sq Ft

$312

vs $312 median

In line with median

Days on Market

0 days

vs 67 days median

67 days fresher than median

Based on 33 active and 94 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of October 28, 2026.

Location

36 Main Street South, Woodbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,125

per month

  • Principal & Interest$3,270
  • Property Taxes$657
  • Insurance$198
  • 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
1800
New Construction
No/Resale
Living Area
1,909 sq ft

Schools

Elementary
Mitchell
High
Nonnewaug

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Window Unit
Fireplaces
1
Laundry
Lower Level
Laundry Location
Basement
Appliances
Electric RangeMicrowaveRefrigeratorDishwasherWasherDryer
Basement
FullUnfinishedStorageConcrete Floor

Exterior & Lot

Lot Size
0.37 acres
Zoning
MSD
Garage / Parking
2 garage spaces4 total parking spacesCarportAttached GaragePavedOn Street ParkingOff Street Parking
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Construction
Clapboard
Color
White
Roof
Asphalt Shingle
Foundation
Stone
Exterior Features
SidewalkGuttersFrench DoorsPatio
Lot Description
Level LotProfessionally Landscaped

Listing & Financials

Property Taxes
$7,888 / Annually
Days on Market
0
MLS #
24217173
MLS Status
Coming Soon

Similar Properties

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Listed By

Christian Jensen

(212) 604-9432

William Pitt Sotheby's Int'l

(860) 868-6600

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

The IDX display contains information sourced from SmartMLS, Inc. as of 10/28/2026. 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 10/28/2026 at 12:30 PM UTC.