348 Hoop Pole Hill Road
Woodbury, Connecticut 06798
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,972
- Acres
- 12.69
- Year Built
- 2000
- 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
Exceptional opportunity to renovate and create your dream country estate on 12.69 private acres in the heart of Woodbury. Privately sited along a quiet country road with seasonal long views, this 2,972 sq. ft. contemporary offers an outstanding combination of acreage, privacy, and potential rarely found at this price point. Designed for comfortable living, the home features a dramatic sunken living room with soaring vaulted ceilings, a fireplace, and walls of windows overlooking the surrounding landscape. The main level includes a spacious primary suite, private office, butler's pantry, and access to expansive decks that invite outdoor entertaining. Upstairs are 3 additional bedrooms and an open den, while the unfinished walk-out lower level offers endless possibilities for future living space. The property's 12.69 acres provide a beautiful backdrop with open land, mature trees, and a four-stall barn, offering flexibility for a variety of country lifestyles. Priced to reflect the opportunity for renovation and updating, this is an exceptional chance for investors, builders, or buyers looking to customize a solidly built home in one of Woodbury's most desirable locations. With great bones, an outstanding setting, and significant upside potential, this property is ready for its next chapter. Sold as is.
Key Facts
- City/Town
- Woodbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Contemporary
- Year Built
- 2000
- Days on Market
- 13 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,972 sq ft
- Lot Size
- 12.69 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $10,724 / Annually
Market Snapshot
The Woodbury Market
Single Family · trailing 12 months
Active Listings
24
27 under contract
Median List Price
$857,000
24 active listings
Median Closed Price
$582,500
88 sales
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
$675,000
vs $857,000 median
21.2% below median
Price / Sq Ft
$227
vs $296 median
23.3% below median
Days on Market
13 days
vs 53 days median
40 days fresher 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
348 Hoop Pole Hill Road, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,442
- Property Taxes$894
- Insurance$225
- 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
- Contemporary
- Year Built
- 2000
- New Construction
- No/Resale
- Living Area
- 2,972 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinishedWalk-out
Exterior & Lot
- Lot Size
- 12.69 acres
- Zoning
- OS100
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vertical Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckStablePaddock
- Lot Description
- Lightly WoodedFarm LandRolling
Listing & Financials
- Property Taxes
- $10,724 / Annually
- Days on Market
- 13
- MLS #
- 24192145
- MLS Status
- Active
Similar Properties
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Co-Listed By
Jackson McCard
W. Raveis Lifestyles Realty
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 11:00 AM UTC.