2 Pomperaug Road
Woodbury, Connecticut 06798
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,480
- Acres
- 0.50
- Year Built
- 1735
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
32
16 under contract
Median List Price
$822,000
32 active listings
Median Closed Price
$580,000
93 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per 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
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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 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.