36 Main Street South
Woodbury, Connecticut 06798
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 1,909
- Acres
- 0.37
- Year Built
- 1800
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
33
16 under contract
Median List Price
$780,000
33 active listings
Median Closed Price
$591,375
94 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 22, 2026per 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
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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 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.