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126 Main Street North

Woodbury, Connecticut 06798

COMING SOON - NEW$699,000
Beds
4
Baths
1 | 1
SqFt
1,872
Acres
1.15
Year Built
1932
Matt Caiola

Matt Caiola

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2-Car Garage1 Fireplace

About This Home

Classic 1930s Colonial set along Main Street in Woodbury, offering the timeless character and craftsmanship of the era. Thoughtfully set back from the road on an expansive lawn, the home features hardwood floors throughout, high ceilings, detailed moldings, interior French doors, charming built-ins, a generous foyer, and a graceful central staircase. The front-to-back living room is anchored by a brick fireplace and opens to a spacious covered porch, creating an inviting setting for everyday living and entertaining. The kitchen and both bathrooms have been updated, blending modern convenience with the home's original character. A beautiful 34' x 27' post-and-beam barn provides exceptional space for a workshop, studio, storage, or other uses. Located within Woodbury's Main Street Design District, the property also offers the flexibility to combine residential living with a business use, subject to applicable regulations. A distinctive property with room to live, work, and enjoy the best of classic Woodbury.

Key Facts

City/Town
Woodbury
Neighborhood
North Woodbury
Property / Style
Single Family · Colonial
Year Built
1932
Days on Market
0 days
Beds
4
Baths
1 full · 1 half
Living Area
1,872 sq ft
Lot Size
1.15 acres
Garage / Parking
2 garage
Property Taxes
$6,422 / Annually

Market Snapshot

The Woodbury Market

Single Family · trailing 12 months

Median Days on Market

59

25 active listings

Median $ / Sq Ft

$286

25 active listings

Sale-to-List Ratio

99.0%

92 sales

How this home compares

List Price

$699,000

vs $825,000 median

15.3% below median

Price / Sq Ft

$373

vs $286 median

30.4% above median

Days on Market

0 days

vs 59 days median

59 days fresher than median

Based on 25 active and 92 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of August 14, 2026.

Location

126 Main Street North, Woodbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,365

per month

  • Principal & Interest$3,597
  • Property Taxes$535
  • Insurance$233
  • 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
Colonial
Year Built
1932
New Construction
No/Resale
Living Area
1,872 sq ft

Schools

Elementary
Mitchell
Middle
Per Board of Ed
High
Nonnewaug

Interior

Heating
Hot Water
Heat Fuel
Gas In Street
Cooling
None
Fireplaces
1
Laundry
Lower Level
Laundry Location
Basement
Appliances
Gas RangeMicrowaveRefrigeratorDishwasherWasherDryerWine Chiller
Basement
Full
Interior Features
Security System

Exterior & Lot

Lot Size
1.15 acres
Zoning
MSD
Garage / Parking
2 garage spacesBarn
Waterfront Details
Not Applicable
Water Source
Public Water In StreetPrivate Well
Sewer
Public Sewer Connected
Construction
Clapboard
Color
White
Roof
Asphalt Shingle
Foundation
ConcreteStone
Exterior Features
SidewalkBarnGarden AreaPatio
Lot Description
City ViewsLevel LotOpen Lot

Listing & Financials

Property Taxes
$6,422 / Annually
Days on Market
0
MLS #
24194243
MLS Status
Coming Soon

Similar Properties

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

Listed By

Timothy Drakeley

(203) 510-9184

Drakeley Real Estate, Inc.

(203) 263-4336

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

The IDX display contains information sourced from SmartMLS, Inc. as of 8/14/2026. 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 8/14/2026 at 6:01 PM UTC.