44 South St

Litchfield, CT 06759

$2,000,000
Price
5
Beds
5,448 Sq. Ft.
$367 / Sq. Ft.
5,448
Sq. Ft.
$367
per Sq. Ft.
Elevator
Cupola

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,...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.
  1. Listed by Patti Guarantano • William Pitt Sotheby's Int'l
    P: (203)-231-9288 C: (203)-231-9288 pguarantano@wpsir.com

Property Details for 44 South Street

Basement Description
Full, Storage, Garage Access, Interior Access, Partially Finished, Walk-out, Full With Walk-Out
Direct Waterfront
No
Garages Number
4
Neighborhood
N/A
Style
Colonial, Victorian
Garage Parking Info
Barn, Attached Garage, Under House Garage
Swimming Pool
Yes
LISTING UPDATED: 02/16/2026 04:44 PM

Property Details for 44 South Street

StatusActive
MLS #24150605
Days on Market8
Taxes$27,091 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1855
Lot Size1.01 AC / 43,995 SF
CountyLitchfield County

Location

Listing Courtesy of William Pitt Sotheby's Int'l, Patti Guarantano
Add your commute

Building Information for 44 South Street

Stories-Year Built1855Building Size-Lot Size1.01 AC / 43,995 SF

Payment Calculator

$12,005 per month

30 year fixed, 6.15% Interest

Principal and Interest

$9,748

Property Taxes

$2,258

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 44 South Street

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Route 63 South from Litchfield Green. 3rd house south of post office on the right.
  • Elementary School: Litchfield Center School
  • High School: Lakeview High School
  • Latitude: 41.745124
  • Longitude: -73.188947
  • Neighborhood Amenities: Golf Course, Health Club, Lake, Library, Park, Shopping/Mall, Stables/Riding, Tennis Courts
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $27,091
Virtual Tour
Interior and Exterior Features
Exterior Features
  • Exterior Features: Balcony, Awnings, Porch, Barn, Deck, Garden Area, French Doors, Patio
  • Pool Description: Heated, Vinyl, In Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Range, Oven/Range, Microwave, Refrigerator, Freezer, Subzero, Dishwasher, Washer, Electric Dryer
  • Attic Description: Storage Space, Floored, Walk-up
  • Cooling System: Central Air, Zoned
  • Heat Type: Hot Air, Radiator
  • Attic YN: Yes
  • Fireplaces Total: 4
  • Interior Features: Auto Garage Door Opener, Cable - Available, Central Vacuum, Elevator
  • Laundry Room Info: Main Level
  • Laundry Room Location: 2nd laundry in primary bedroom
  • Rooms Additional: Foyer, Mud Room, Workshop
  • Rooms Total: 13
Room 1
  • Room Entry Order: 1
  • Room Features: Built-In Hutch,Dining Area,Fireplace,Pantry,Hardwood Floor
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 25.0
Room 2
  • Room Entry Order: 10
  • Room Features: Bay/Bow Window,Hardwood Floor
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 20.0
Room 3
  • Room Entry Order: 11
  • Room Features: Bay/Bow Window,Hardwood Floor
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 18.0
Room 4
  • Room Entry Order: 12
  • Room Features: Hardwood Floor
  • Room Length: 12.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 5
  • Listing Key: 48FF9180CE3065DAE063E201100AF284
  • Room Entry Order: 2
  • Room Features: Book Shelves,Fireplace,Hardwood Floor
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Formal Dining Room
  • Room Width: 18.0
Room 6
  • Room Entry Order: 3
  • Room Features: Bay/Bow Window,Fireplace,Hardwood Floor
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Library
  • Room Width: 18.0
Room 7
  • Room Entry Order: 4
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 25.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 19.0
Room 8
  • Room Entry Order: 5
  • Room Features: French Doors,Hardwood Floor
  • Room Length: 11.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 11.0
Room 9
  • Listing Key: 48FF9180CE3065DAE063E201100AF284
  • Room Entry Order: 6
  • Room Features: Dining Area,French Doors,Hardwood Floor
  • Room Length: 13.0
  • Room Level: Main
  • Room Type: Sun Room
  • Room Width: 28.0
Room 10
  • Room Entry Order: 7
  • Room Features: Laundry Hookup
  • Room Length: 9.0
  • Room Level: Main
  • Room Type: Other
  • Room Width: 12.0
Room 11
  • Room Entry Order: 8
  • Room Features: Dressing Room,Full Bath,Stall Shower,Walk-In Closet,Hardwood Floor
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Primary BR Suite
  • Room Width: 14.0
Room 12
  • Room Entry Order: 9
  • Room Features: Balcony/Deck,French Doors,Full Bath,Hydro-Tub,Walk-In Closet,Hardwood Floor
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 14.0
Property
Property and Assessments
  • Color: Cream
  • Construction Description: Frame
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete, Masonry
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1855
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 5448
Lot Information
  • Lot Description: Treed, Level Lot, Professionally Landscaped, Historic District
  • Parcel Number: 818184
  • Sq Ft Est Heated Above Grade: 5448.0
  • Sq Ft Total: 5448.0
  • Zoning: HR30
Utilities
  • Energy Features: Generator, Programmable Thermostat
  • Heat Fuel Type: Oil
  • Hot Water Description: 80 Gallon Tank
  • Radon Mitigation Air: Yes
  • Radon Mitigation Water: No
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 44 South Street

DateEvent & SourcePriceAppreciation
Apr 12, 2021

Closed (Public Record)

Public Record #1458348515

$275,000

-15.2% / yr

Aug 20, 2010

Closed (Public Record)

Public Record #295254590

$1,600,000

+2852.3% / yr

Jun 1, 2006

Closed (Public Record)

Public Record #327109374

$1

-99.7% / yr

Jan 13, 2004

Closed (Public Record)

Public Record #131247267

$1,240,000

+10.8% / yr

Nov 12, 2002

Closed (Public Record)

Public Record #106947634

$1,100,000

+13.9% / yr

Oct 12, 1994

Closed (Public Record)

Public Record #91871983

$385,000—
DateEvent & SourcePrice
04/12/2021

Closed (Public Record)

Public Record #1458348515

$275,000

-15.2% / yr

08/20/2010

Closed (Public Record)

Public Record #295254590

$1,600,000

+2852.3% / yr

06/01/2006

Closed (Public Record)

Public Record #327109374

$1

-99.7% / yr

01/13/2004

Closed (Public Record)

Public Record #131247267

$1,240,000

+10.8% / yr

11/12/2002

Closed (Public Record)

Public Record #106947634

$1,100,000

+13.9% / yr

10/12/1994

Closed (Public Record)

Public Record #91871983

$385,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 44 South Street

Taxable ValueLand$202,330Additions$1,040,360Total$1,242,690
Tax Record2024$27,091 ($2,258 / month)
Home Facts
Beds5Baths5.5Total Finished SqFt5,448 SqFtAbove Grade Finished SqFt5,448 SqFtUnfinished Basement SqFt420 SqFtStories2Lot Size43,996 SqFtStyleSingle Family ResidenceYear Built1855ZoningHR30CountyLITCHFIELDAPNLITC M:206 B:47 L:11Fireplace TypeHas Fireplace

Schools near 44 South Street

This home is within Litchfield School District.
Rating
School
Type
Grades
Distance
Litchfield Intermediate School
Public - 4 to 6
Litchfield Middle School
Public - 7 to 8
Litchfield High School
Public - 9 to 12
Center School
Public - PK to 3
Rating
School
Distance
Litchfield Intermediate School
Public4 to 6

Litchfield Middle School
Public7 to 8

Litchfield High School
Public9 to 12

Center School
PublicPK to 3

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 44 South Street, Litchfield, CT 06759

44 South Street is a single family home for sale in Litchfield, CT 06759. This property was listed for sale on February 12, 2026 by William Pitt Sotheby's Int'l, it's currently listed at $2,000,000. It has been on the market for a total of 8 days and was last sold on April 12, 2021. This listing's school district is Litchfield School District. Nearby schools include Litchfield Intermediate School, Litchfield Middle School and Litchfield High School. 44 South Street is a 5-bed, 7-bath, 5,448 sqft single family home built in 1855.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Pitt Sotheby's Int'l, Patti Guarantano

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.