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44 South Street, 
Litchfield, CT 06759

$2,000,000


5

Beds


7

Baths


5,448

Sq Ft


Single Family


Virtual Tour

Pending

Listed by

Patti Guarantano, (203) 231-9288

William Pitt Sotheby'S Int'L, (860) 868-6600

Last updated:

February 24, 2026, 02:42 AM

MLS#

24150605

Source:

CT

About This Home

44 South Street

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.

Home Facts

Single Family

7 Baths

5 Bedrooms

Built in 1855

Price Summary

2,000,000

$367 per Sq. Ft.

MLS #:

24150605

Last Updated:

February 24, 2026, 02:42 AM

Added:

21 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

7

Full Bathrooms:

4

Interior

Living Area:

5,448 Sq. Ft.


Structure

Structure

Architectural Style:

Colonial, Victorian

Building Area:

5,448 Sq. Ft.

Year Built:

1855


Lot

Lot Size (Sq. Ft):

43,995


Finances & Disclosures

Finances

Price:

$2,000,000

Price per Sq. Ft:

$367 per Sq. Ft.

Source:CT
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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.