$2,000,000

44 South Street, Litchfield, CT 06759

  • 5 beds |
  • 7 baths |
  • 5,448 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1855
  • Property Lot Size Icon1.01acre lot
  • Property Parking Icon 4 car garage
  • Property Price Per Square Feet Icon $367/sqft
  • Property List Date Icon Listed 1 month ago

Property Description

In the heart of Litchfield's coveted Historic District, along one of the town's most admired streets, stands the circa-1855 Woodruff House, an iconic Italianate Victorian Villa and enduring centerpiece of the neighborhood. Built for prominent Litchfield resident George Morris Woodruff, this beloved home blends architectural pedigree with modern livability. Signature elements include a shallow hipped roofline, distinctive columned verandah, double-tiered gallery, and dramatic two-story octagonal bays, a rare and remarkably preserved example of the period. Inside, grand yet inviting spaces unfold: formal entry hall, multiple living rooms for gathering and quiet retreat, dining room, den, office, and a spacious kitchen opening to a comfortable family room. The home offers five bedrooms including two primary suites, along with four full and three half baths, allowing guests and owners alike to live graciously. French doors lead to a sunroom and deck overlooking mature, landscaped grounds designed for entertaining with two patios, an updated heated pool, and the kind of setting that makes weekends linger longer. Modern comforts integrate seamlessly: elevator to primary bedroom, generator, four fireplaces and laundry room. A heated two-story barn provides flexible space for studio, workshop, or collector storage with room for two vehicles. Moments to the Litchfield Green. A rare opportunity to own not simply a home, but a recognized piece of Litchfield's architectural legacy.

Listing Status:
Pending
Date Added:
February 12, 2026
Data Last Updated:
March 28, 2026 at 4:50AM
Listing Office:
William Pitt Sotheby's Int'l : (860) 868-6600
Listing Agent:
Patti Guarantano : (203) 231-9288
MLS ID:
24150605
  • General: Auto Garage Door OpenerCable - AvailableCentral VacuumElevator
  • Rooms: FoyerMud RoomWorkshop
  • Appliances: Gas RangeOven/RangeMicrowaveRefrigeratorFreezerSubzeroDishwasherWasherElectric Dryer
  • Laundry: Main Level
  • Basement: FullStorageGarage AccessInterior AccessPartially FinishedWalk-outFull With Walk-Out
  • A/C: Central AirZoned
  • Heating: Hot AirRadiatorOil
  • Fireplace: Fireplaces: 4
  • General: BalconyAwningsPorchBarnDeckGarden AreaFrench DoorsPatio
  • Style: ColonialVictorian
  • Pool: HeatedVinylIn Ground Pool
  • Roofing: Asphalt Shingle
  • County: Litchfield
  • Zoning: HR30818184
  • Restrictions: Regulated Historic DistrictRight of Way
  • Water: Public Water Connected
  • Sewer: Public Sewer Connected

This listing courtesy of Patti Guarantano , William Pitt Sotheby's Int'l

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

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Location

Schools Nearby

C

Center School

125 West St, Litchfield, CT, 06759

Grades PK-3

0.31 miles away

L

Litchfield Middle School

14 Plumb Hill Rd, Litchfield, CT, 06759

Grades 7-8

0.94 miles away

L

Litchfield High School

14 Plumb Hill Rd, Litchfield, CT, 06759

Grades 9-12

0.94 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.