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2 Pomperaug Road

Woodbury, Connecticut 06798

COMING SOON - NEW$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 for a relaxing stroll, yet you can walk to an amazing collection of local favorites-inc. 9 fine restaurants, 4 diners, a brewery w/ live entertainment, and a French bakery. No wonder they call it "Food-bury!" Come home to the stone path to leading to a beautiful stone landing. Step inside, where warmth & character surround you. The spacious L-shaped living room offers two inviting gathering areas. At one end, a wood-burning fireplace creates a cozy setting with room for a baby grand piano; at the other, a woodstove adds warmth beside a full-wall library & second seating area. Just beyond is a sun-filled, beamed room wrapped in windows on three side is a perfect spot for breakfast, reading, creating art, watching TV, or simply enjoying the view. The charming country kitchen features high-end appliances and a picture-perfect window. Two staircases lead upstairs to three restful bedrooms & two beautifully renovated full baths, including luxurious features such as a steam shower & soaking tub. Entertaining is Indoors and Outdoors! From the formal dining room, to an incredible backyard oasis with winding garden paths, a full outdoor kitchen, heated inground pool, a firepit, and a covered breezeway for enjoying the outdoors even when the weather doesn't cooperate.

Key Facts

City/Town
Woodbury
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1735
Days on Market
0 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

66

32 active listings

Median $ / Sq Ft

$331

32 active listings

Sale-to-List Ratio

99.2%

93 sales

How this home compares

List Price

$875,000

vs $822,000 median

6.4% above median

Price / Sq Ft

$353

vs $331 median

6.6% above median

Days on Market

0 days

vs 66 days median

66 days fresher than median

Based on 32 active and 93 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of September 25, 2026.

Location

2 Pomperaug Road, Woodbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,598

per month

  • Principal & Interest$4,671
  • 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
HeatedConcreteVinylIn 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
0
MLS #
24209527
MLS Status
Coming Soon

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 9/25/2026. 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 9/25/2026 at 4:51 AM UTC.