44 South Street, Litchfield, CT 06759 - Photo 1

1/1

$2,188,000

Sold
Closed
Single Family
5 Beds
4 Full Baths
3 Partial Baths
5,448 Sq. Ft.
4 Car Garage

1/1

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.

Full Property Details

Full Property Details for 44 South St

General

Sold For: $2,188,000
Taxes: (July 2025-June 2026)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24150605
Added to Site: 102 day(s) ago

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, Walk-In Closet, 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
Sold by Klemm Real Estate Inc, Maria Taylor and Klemm Real Estate Inc, Claudine McHugh

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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

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NMLS#: 1598647

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Schools

Schools serving 44 South St

School District:Litchfield School District

Name	Grades	Distance
Center School, Litchfield, CT 125 West Street, Litchfield, CT 06759	PK-3	0.3 mi
Litchfield Intermediate School 35 Plumb Hill Road, Litchfield, CT 06759	4-6	0.9 mi
Litchfield Middle School 14 Plumb Hill Road, Litchfield, CT 06759	7-8	1 mi
Litchfield High School 14 Plumb Hill Road, Litchfield, CT 06759	9-12	1 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 44 South St

Date

Details

Price

Change

Source

4/15/2026

Sold

$2,188,000

9.4%

MLS

2/12/2026

Listed

$2,000,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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3
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Total Baths
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Active
Updated 23 hours ago

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1
Bed
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Total Bath
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2
Beds
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Total Baths
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-$14,100 (-4.88%)

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Active
Updated 5 days ago

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Beds
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Total Baths
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Sq. Ft.

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Sold

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Beds
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Total Baths
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44 South Street, Litchfield, CT 06759 (MLS# 24150605) is a Single Family property that was sold at $2,188,000 on April 15, 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.

44 South St Litchfield, CT 06759