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2 Pomperaug Road

Woodbury, Connecticut 06798

ACTIVE$875,000
Beds
3
Baths
2 | 1
SqFt
2,480
Acres
0.50
Year Built
1735
Matt Caiola

Matt Caiola

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Pool1-Car Garage3 Fireplaces

About This Home

Welcome to history, charm, and an incredible location-the best of both worlds! Tucked along a quiet side road, this lovingly cared-for antique offers a peaceful, private setting with a picturesque waterfall nearby, yet is within walking distance to an amazing collection of local favorites, including fine restaurants, diners, a brewery, pub with live entertainment, and French bakery. No wonder they call it "Food-bury!" A stone path leads to a beautiful stone landing and a home filled with warmth and character. The spacious L-shaped living room offers two inviting gathering areas-one centered around a wood-burning fireplace with room for a grand piano, and the other warmed by a woodstove beside a full-wall library and second seating area. Just beyond is a sun-filled, beamed room wrapped in windows on three sides, perfect for breakfast, reading, art, TV, or simply enjoying the view. The charming country kitchen is exceptionally appointed with premium Viking, Miele, Sub-Zero, Dacor and Fisher & Paykel appliances, including an induction cooktop, wall and speed ovens, warming drawer and 2-drawer dishwasher. Thoughtful details include Waterworks fixtures, a pot filler, custom pull-out cabinetry and under-cabinet lighting. Two staircases lead to three restful bedrooms and two beautifully renovated full baths. The primary bath features a Waterworks vanity with quartz top and Waterworks hardware, while the second bath creates a spa-like retreat with a soaking tub and steam shower.

Key Facts

City/Town
Woodbury
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1735
Days on Market
49 days
Beds
3
Baths
2 full · 1 half
Living Area
2,480 sq ft
Lot Size
0.50 acres
Garage / Parking
1 garage · 4 total
Property Taxes
$7,618 / Annually

Market Snapshot

The Woodbury Market

Single Family · trailing 12 months

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

$875,000

vs $799,950 median

9.4% above median

Price / Sq Ft

$353

vs $322 median

9.6% above median

Days on Market

49 days

vs 62 days median

13 days fresher 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

2 Pomperaug Road, Woodbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,636

per month

  • Principal & Interest$4,709
  • Property Taxes$635
  • Insurance$292
  • 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
Year Built
1735
New Construction
No/Resale
Living Area
2,480 sq ft

Schools

Elementary
Mitchell
High
Nonnewaug

Interior

Heating
Hot Air
Heat Fuel
OilPropane
Cooling
Ceiling FansCentral Air
Fireplaces
3
Laundry
Main Level
Appliances
Cook TopWall OvenConvection OvenMicrowaveSubzeroDishwasherDisposalWasherDryer
Basement
PartialUnfinished

Exterior & Lot

Lot Size
0.50 acres
Zoning
OS80
Garage / Parking
1 garage space4 total parking spacesDetached GarageDrivewayPrivatePaved
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Pool
HeatedVinylIn Ground Pool
Construction
Clapboard
Color
Cream
Roof
Asphalt Shingle
Foundation
Stone
Exterior Features
GrillBreezewayShedFruit TreesPorchGarden AreaPatio
Lot Description
Fence - PartialLightly WoodedLevel Lot

Listing & Financials

Property Taxes
$7,618 / Annually
Days on Market
49
MLS #
24209527
MLS Status
Active

Similar Properties

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

Listed By

Pam Famiglietti

(203) 560-0753

William Raveis Real Estate

(203) 264-8180

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 3:10 AM UTC.