385 Middle Road Turnpike
Woodbury, Connecticut 06798
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,394
- Acres
- 3.29
- Year Built
- 1950
- Property Type
- Single Family

Matt Caiola
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About This Home
Set on 3.29 picturesque acres bordering conservation land, this beautifully maintained and thoughtfully remodeled country Cape is filled with character, custom craftsmanship and modern amenities. The estate-like grounds and versatile floor plan offer privacy, comfort and functionality, including options for multigenerational living. At the heart of the home, the custom country kitchen features granite countertops, a farmhouse sink, stainless steel appliances and handcrafted cabinetry, opening to a sun-filled sitting/living room with a propane fireplace/stove. The generously sized dining room has its own fireplace, distinctive checkerboard wood floors and a bay window, with the versatility to serve as another living area if desired. The main level includes a primary bedroom with private full bath, a second bedroom, remodeled powder room and separate office or craft room. At the rear, the mudroom incorporates laundry and antique chestnut cabinetry, one of the many details that give this home its individual character. Upstairs are two spacious bedrooms, an updated full bath, built-in storage and a large walk-in attic with the potential for future finished space. The walk-out finished lower level adds another dimension to the home, with a fireplace and antique reclaimed pine cupboards and built-ins. This comfortable area lends itself to recreation, a home office or simply relaxing. A substantial unfinished basement provides abundant storage. The grounds are equally impressive.
Key Facts
- City/Town
- Woodbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1950
- Days on Market
- 69 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,394 sq ft
- Lot Size
- 3.29 acres
- Garage / Parking
- 3 garage · 6 total
- Property Taxes
- $7,385 / Annually
Market Snapshot
The Woodbury Market
Single Family · trailing 12 months
Active Listings
31
18 under contract
Median List Price
$780,000
31 active listings
Median Closed Price
$596,375
92 sales
Median Days on Market
64
31 active listings
Median $ / Sq Ft
$312
31 active listings
Sale-to-List Ratio
99.4%
92 sales
How this home compares
List Price
$875,000
vs $780,000 median
12.2% above median
Price / Sq Ft
$365
vs $312 median
17.0% above median
Days on Market
69 days
vs 64 days median
5 days longer than median
Based on 31 active and 92 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of November 5, 2026.
Location
385 Middle Road Turnpike, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 29, 2026per month
- Principal & Interest$4,770
- Property Taxes$615
- 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
- Cape Cod
- Year Built
- 1950
- New Construction
- No/Resale
- Living Area
- 2,394 sq ft
- Below Grade
- 280 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Nonnewaug
Interior
- Heating
- BaseboardHot Air
- Heat Fuel
- Oil
- Cooling
- Window Unit
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- Gas RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- FullHeatedStoragePartially FinishedWalk-outFull With Walk-Out
- In-Law Apartment
- PossibleLower LevelOver Garage
- Interior Features
- Auto Garage Door OpenerCable - Available
- Additional Rooms
- Workshop
Exterior & Lot
- Lot Size
- 3.29 acres
- Zoning
- OS60
- Garage / Parking
- 3 garage spaces6 total parking spacesBarnDetached GarageOff Street ParkingDrivewayPrivatePavedGravel
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Wood
- Color
- White
- Roof
- Asphalt ShingleFlat
- Foundation
- ConcreteStone
- Exterior Features
- ShedPorchBarnGuttersGarden AreaStone WallPatio
- Lot Description
- Some WetlandsLevel LotProfessionally LandscapedOpen Lot
Listing & Financials
- Property Taxes
- $7,385 / Annually
- Days on Market
- 69
- MLS #
- 24202477
- MLS Status
- Under Contract
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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 11/5/2026. 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 11/5/2026 at 6:50 PM UTC.