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385 Middle Road Turnpike

Woodbury, Connecticut 06798

PENDING$875,000
Beds
4
Baths
2 | 1
SqFt
2,394
Acres
3.29
Year Built
1950
Matt Caiola

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,677

per 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

Similar Properties

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

Listed By

Liz Newnham

(203) 994-4123

William Pitt Sotheby's Int'l

(203) 796-7700

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.