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$2,000,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 3 Partial Baths
  • 5,448 Sq. Ft.
  • 4 Car Garage
  • Updated 15 hours ago
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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.

Full Property Details for 44 South St

General

  • Price: $2,000,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24150605
  • Updated: Today (2/12/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 13
  • Rooms/Areas: Foyer, Mud Room, Workshop
  • Interior Features: Auto Garage Door Opener, Cable - Available, Central Vacuum, Elevator
  • Fireplace: Yes
  • Number of Fireplaces: 4
  • Appliances: Gas Range, Oven/Range, Microwave, Refrigerator, Freezer, Subzero, Dishwasher, Washer, Electric Dryer

Rooms

Bathrooms

  • Total Bathrooms: 7
  • Full Bathrooms: 4
  • Half Bathrooms: 3

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - Balcony/Deck, French Doors, Full Bath, Hydro-Tub, Hardwood Floor, 14 x 14, Upper
  • Primary Suite: Dressing Room, Full Bath, Stall Shower, Walk-In Close, 14 x 14, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, 12 x 12, Upper
  • Bedroom 2: Bedroom - Bay/Bow Window, Hardwood Floor, 13 x 18, Upper
  • Bedroom 3: Bedroom - Bay/Bow Window, Hardwood Floor, 15 x 20, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, 25 x 19, Main
  • Kitchen: Kitchen - Built-In Hutch, Dining Area, Fireplace, Pantry, Hardwood Floor, 14 x 25, Main
  • Formal Dining Room: Formal Dining Room - Book Shelves, Fireplace, Hardwood Floor, 15 x 18, Main
  • Office: Office - French Doors, Hardwood Floor, 11 x 11, Main
  • Library: Library - Bay/Bow Window, Fireplace, Hardwood Floor, 17 x 18, Main
  • Laundry: Main Level
  • Other Room 1: Other - Laundry Hookup, 9 x 12, Main

Additional Information

  • Pool: Yes
  • Pool Description: Heated, Vinyl, In Ground Pool

Exterior

  • Exterior Features: Balcony, Awnings, Porch, Barn, Deck, Garden Area, French Doors, Patio
  • Color: Cream

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 4
  • Parking: Barn, Attached Garage, Under House Garage

Location

  • County: Litchfield
  • Driving Directions: Route 63 South from Litchfield Green. 3rd house south of post office on the right.

School Information

  • Elementary School: Litchfield Center School
  • High School: Lakeview High School

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Hot Air, Radiator, Oil
  • Heating Fuel: Oil
  • Water Heater: 80 Gallon Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial, Victorian
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Storage, Garage Access, Interior Access, Partially Finished, Walk-out, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 5,448
  • Above Ground: 5,448 Sq. Ft.
  • Year Built: 1855

Lot Features

  • Lot Size (Acres): 1.01
  • Zoning: HR30
  • Lot Description: Treed, Level Lot, Professionally Landscaped, Historic District

Green Features

  • Energy Features: Generator, Programmable Thermostat

Financial Considerations

  • Assessment Amount: $1,242,690
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 818184

Listed by William Pitt Sotheby's Int'l, Patti Guarantano

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Listing agent

— 44 South St —

  • Patti Guarantano

    William Pitt Sotheby's Int'l

Agent Contact: (203) 231-9288 Office Contact: (860) 868-6600

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 44 South St

School District:Litchfield School District
NameGradesDistance
Center School, Litchfield, CT
125 West Street, Litchfield, CT 06759
PK-30.3 mi
Litchfield Intermediate School
35 Plumb Hill Road, Litchfield, CT 06759
4-60.9 mi
Litchfield Middle School
14 Plumb Hill Road, Litchfield, CT 06759
7-81 mi
Litchfield High School
14 Plumb Hill Road, Litchfield, CT 06759
9-121 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 44 South St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/12/2026
Listed
$2,000,000
627.27%
MLS
4/12/2021
Sold
$275,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 44 South St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$27,091
7%
$1,242,690
—
2023
$25,227
3%
$1,242,690
48%
2023
$24,581
-1%
$841,830
—
2022
$24,834
-3%
$841,830
—
2021
$25,507
2%
$841,830
—
2020
$25,002
-2%
$841,830
—
2019
$25,423
8%
$841,830
6%
2018
$23,629
2%
$795,600
—
2017
$23,232
3%
$795,600
—
2016
$22,515
100%
$795,600
—
2015
-100%
$795,600
—
2014
$21,107
3%
$795,600
-7%
2011
$20,445
—
$859,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by William Pitt Sotheby's Int'l, Patti Guarantano

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44 South Street, Litchfield, CT 06759 (MLS# 24150605) is a Single Family property with 5 bedrooms, 4 full bathrooms and 3 partial bathrooms. 44 South Street is currently listed for $2,000,000 and was received on February 12, 2026. Want to learn more about 44 South Street? Do you have questions about finding other Single Family real estate for sale in Litchfield? You can browse all Litchfield real estate or contact a Coldwell Banker agent to request more information.

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