44 South St

Off Market

44 South St

Litchfield CT 06759

5448 sq. ft.

1.01 ac.

Single-Family

Last sold for $2,188,000

Patti Guarantano, last sold this property on 15 April 2026 after 62 days on market.

Overview

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.

Features

5 bedrooms

7 bathrooms

4 carspaces

4 garage spaces

5448 sq. ft. floor area

1.01 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Litchfield over the last 12 months, the estimated median property value of 44 South St is $1.06m.

Median value

$1.06m

Estimated value range

$465k - $2.19m

Median days on market

Estimated value trend

46%

increase over the last 12 months

Average days on market is based on recent, comparable sales in Litchfield. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 44 South St

2026

Sold

$2,188,000

15 Apr 2026 by Patti Guarantano, of William Pitt Sotheby's Int'l

2021

Sold

$1,750,000

22 Oct 2021 by JANE HINKEL, of William Pitt Sotheby's Int'l

2010

Sold

$1,600,000

20 Aug 2010 by MARTHA OLIN, of William Pitt Sotheby's Int'l

Happy sellers in Litchfield

We have insufficient information to provide an overview of customer satisfaction for Litchfield. Viewing the agent profiles, reviews and sales for Litchfield can provide insights for this location.

Local market activity for 5 bedroom single-family properties in Litchfield

In the last 12 months, 4 five-bedroom single-family properties similar to 44 South St, have been sold.

This represents a 29% increase in five-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Litchfield for a market analysis.

Dave Luzi, Litchfield CT Realtor

at E.J. Murphy Realty

(16 reviews)

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ROLAND LEAL

at William Pitt Sotheby's Int'l

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Kim D'andrea

at William Pitt Sotheby's Int'l

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Andrew Murphy

at E.J. Murphy Realty

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Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Litchfield

Dave Luzi, Litchfield CT Realtor

Dave Luzi, Litchfield CT Realtor is a recommended agent for Litchfield. They have 2 local sales and collected 2 local reviews across the last 12 months.