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
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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
Active Listings
34
15 under contract
Median List Price
$799,950
34 active listings
Median Closed Price
$600,000
93 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 12, 2026per 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
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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 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.