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509 Main Street North

Woodbury, Connecticut 06798

PENDING$1,790,000

Reduced from $1,850,000

Beds
6
Baths
6 | 2
SqFt
6,357
Acres
3.62
Year Built
2007
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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4 FireplacesVirtual TourPrice Reduced

About This Home

Tucked away in absolute privacy, yet centrally located, this exceptional estate offers 6,300+ square feet of refined living space that seamlessly blends country sophistication modern luxuries. Crafted w/warmth & character throughout, the home boasts wide board hardwood floors, coffered ceilings, French doors, exposed beams, & built-ins. With 13 thoughtfully designed rooms, the home features 6 generous bedrooms, 6 full bathrooms, & two 1/2 baths. Each bath w/radiant heated floors for comfort. Primary suite has 2 walk-in closets, & office space. At the heart of the home is a stunning, brand-new custom kitchen featuring handcrafted cabinetry, an 8-burner gas range, built-in coffee bar, & an elegant butler's pantry. The floor plan offers multiple spaces to live and unwind: a formal living room w/fireplace, a media/game room on the lower level, a dedicated home gym, & two convenient laundry areas. Additional fireplaces can be found in the eat in kitchen, primary suite, & lower level. Heated 2-car garage w/EV charging station & unfinished space above for future customization. The two-story barn offers storage & creative use. The beautifully manicured grounds are a celebration of nature: stone walls & lush gardens frame multiple outdoor living spaces. There are stone patios/walkways, covered porches, & the built-in grill is perfect for entertaining. Tap maple trees for syrup in winter, tend bees & gardens in summer, or press cider in the fall... this home is a year round experience!

Key Facts

City/Town
Woodbury
Property / Style
Single Family · Cape Cod
Year Built
2007
Days on Market
341 days
Beds
6
Baths
6 full · 2 half
Living Area
6,357 sq ft
Lot Size
3.62 acres
Property Taxes
Not on file from MLS

Market Snapshot

The Woodbury Market

Single Family · trailing 12 months

Median Days on Market

53

24 active listings

Median $ / Sq Ft

$296

24 active listings

Sale-to-List Ratio

99.0%

88 sales

How this home compares

List Price

$1.79M

vs $857,000 median

2.1× the median

Price / Sq Ft

$282

vs $296 median

In line with median

Days on Market

341 days

vs 53 days median

288 days longer than median

Based on 24 active and 88 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of July 29, 2026.

Location

509 Main Street North, Woodbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$9,724

per month

  • Principal & Interest$9,127
  • Property Taxes$0
  • Insurance$597
  • HOA$0

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

Location

City/Town
Woodbury
County
Litchfield

Residence

Property Type
Single Family
Style
Cape Cod
Year Built
2007
Living Area
6,357 sq ft

Schools

Elementary
Mitchell
High
Nonnewaug

Interior

Heating
Hot Air
Cooling
Central Air
Fireplaces
4
Laundry
Lower LevelMain Level
Interior Features
Audio SystemAuto Garage Door OpenerSecurity System
Additional Rooms
Exercise RoomLaundry RoomMud Room

Exterior & Lot

Lot Size
3.62 acres
Garage / Parking
Attached Garage
Waterfront Details
Not Applicable
Construction
ClapboardWood
Roof
Wood Shingle
Foundation
ConcreteStone
Lot Description
Interior LotTreedLevel LotProfessionally Landscaped

Listing & Financials

Days on Market
341
MLS #
24121221
MLS Status
Under Contract - Continue to Show

Similar Properties

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

Listed By

April Furey

(203) 858-9643

Keller Williams Realty Prtnrs.

(203) 459-4663

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. 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 7/29/2026 at 12:45 PM UTC.