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348 Hoop Pole Hill Road

Woodbury, Connecticut 06798

ACTIVE$675,000
Beds
4
Baths
2 | 1
SqFt
2,972
Acres
12.69
Year Built
2000
Matt Caiola

Matt Caiola

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3-Car Garage1 Fireplace

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

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

Property + 11 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,561

per 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

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

Listed By

Rebecca Doh

(860) 601-4406

W. Raveis Lifestyles Realty

(860) 868-0511

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.