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.
Sold for $2,188,000
$2,188,000
44 South Street, Litchfield, CT 06759
5beds
5,448sqft
Single Family Residence
Built in 1855
1.01 Acres Lot
$2,206,600 Zestimate®
$402/sqft
$5,367 Estimated rent
Home value
$2,206,600
$1.90M - $2.56M
$5,367/mo
Zestimate® history
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Four fireplacesIconic italianate victorian villaDramatic two-story octagonal baysDistinctive columned verandahDouble-tiered galleryRoom for two vehiclesUpdated heated pool
Zillow last checked:
Listing updated:
Listed by:
Patti Guarantano (203)231-9288,
William Pitt Sotheby's Int'l 860-868-6600
Bought with:
Maria Taylor, RES.0752614
Klemm Real Estate Inc
Claudine McHugh
Klemm Real Estate Inc
Source: Smart MLS,MLS#: 24150605
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 7
- Full bathrooms: 4
- 1/2 bathrooms: 3
Primary bedroom
- Features: Dressing Room, Full Bath, Stall Shower, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 196 Square Feet
- Dimensions: 14 x 14
Primary bedroom
- Features: Balcony/Deck, French Doors, Full Bath, Hydro-Tub, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 196 Square Feet
- Dimensions: 14 x 14
Bedroom
- Features: Bay/Bow Window, Hardwood Floor
- Level: Upper
- Area: 300 Square Feet
- Dimensions: 20 x 15
Bedroom
- Features: Bay/Bow Window, Hardwood Floor
- Level: Upper
- Area: 234 Square Feet
- Dimensions: 18 x 13
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 144 Square Feet
- Dimensions: 12 x 12
Dining room
- Features: Bookcases, Fireplace, Hardwood Floor
- Level: Main
- Area: 270 Square Feet
- Dimensions: 18 x 15
Kitchen
- Features: Built-in Features, Dining Area, Fireplace, Pantry, Hardwood Floor
- Level: Main
- Area: 350 Square Feet
- Dimensions: 25 x 14
Library
- Features: Bay/Bow Window, Fireplace, Hardwood Floor
- Level: Main
- Area: 306 Square Feet
- Dimensions: 18 x 17
Living room
- Features: Fireplace, Hardwood Floor
- Level: Main
- Area: 475 Square Feet
- Dimensions: 19 x 25
Office
- Features: French Doors, Hardwood Floor
- Level: Main
- Area: 121 Square Feet
- Dimensions: 11 x 11
Other
- Features: Laundry Hookup
- Level: Main
- Area: 108 Square Feet
- Dimensions: 12 x 9
Sun room
- Features: Dining Area, French Doors, Hardwood Floor
- Level: Main
- Area: 364 Square Feet
- Dimensions: 28 x 13
Heating
- Forced Air, Radiator, Oil
Cooling
- Central Air, Zoned
Appliances
- Included: Gas Range, Oven/Range, Microwave, Refrigerator, Freezer, Subzero, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Main Level, Mud Room
Features
- Central Vacuum, Elevator, Entrance Foyer
- Doors: French Doors
- Basement: Full,Storage Space,Garage Access,Interior Entry,Partially Finished,Walk-Out Access
- Attic: Storage,Floored,Walk-up
- Number of fireplaces: 4
Interior area
- Total structure area: 5,448
- Total interior livable area: 5,448 sqft
- Finished area above ground: 5,448
Property
Parking
- Total spaces: 4
- Parking features: Barn, Attached, Garage Door Opener
- Attached garage spaces: 4
Features
- Patio & porch: Porch, Deck, Patio
- Exterior features: Balcony, Awning(s), Garden
- Has private pool: Yes
- Pool features: Heated, Vinyl, In Ground
Lot
- Size: 1.01 Acres
- Features: Wooded, Level, Landscaped, Historic District
Details
- Additional structures: Barn(s)
- Parcel number: 818184
- Zoning: HR30
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Victorian
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Concrete Perimeter, Masonry
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1855
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Available
Green energy
- Energy efficient items: Thermostat
Community & neighborhood
Community
- Community features: Golf, Health Club, Lake, Library, Park, Shopping/Mall, Stables/Riding, Tennis Court(s)
Location
- Region: Litchfield
Price history
| Date | Event | Price |
|---|---|---|
| 4/15/2026 | Sold | $2,188,000+9.4%$402/sqft |
Source:  Smart MLS #24150605 Report a problem | ||
| 3/8/2026 | Pending sale | $2,000,000$367/sqft |
Source: Smart MLS #24150605 Report a problem | ||
| 2/12/2026 | Listed for sale | $2,000,000+14.3%$367/sqft |
Source: Smart MLS #24150605 Report a problem | ||
| 10/22/2021 | Sold | $1,750,000$321/sqft |
Source: Smart MLS #170400250 Report a problem | ||
| 8/24/2021 | Contingent | $1,750,000$321/sqft |
Source: Smart MLS #170400250 Report a problem | ||
| 6/18/2021 | Listed for sale | $1,750,000+536.4%$321/sqft |
Source: Smart MLS #170400250 Report a problem | ||
| 4/19/2021 | Sold | $275,000-82.8%$50/sqft |
Source: Public Record Report a problem | ||
| 8/20/2010 | Sold | $1,600,000+29%$294/sqft |
Source: Smart MLS #L133895 Report a problem | ||
| 1/13/2004 | Sold | $1,240,000+12.7%$228/sqft |
Source: Public Record Report a problem | ||
| 11/12/2002 | Sold | $1,100,000$202/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $27,091 +7.4% | $1,242,690 |
| 2024 | $25,227 +2.6% | $1,242,690 +47.6% |
| 2023 | $24,581 -1% | $841,830 |
| 2022 | $24,834 -2.6% | $841,830 |
| 2021 | $25,507 +2% | $841,830 |
| 2020 | $25,002 -1.7% | $841,830 |
| 2019 | $25,423 +7.6% | $841,830 +5.8% |
| 2018 | $23,629 +1.7% | $795,600 |
| 2017 | $23,232 +3.2% | $795,600 |
| 2016 | $22,515 | $795,600 |
Find assessor info on the county website
Neighborhood: 06759
Nearby schools
GreatSchools rating
- 7/10Center SchoolGrades: PK-3Distance: 0.3 mi
- 6/10Litchfield Middle SchoolGrades: 7-8Distance: 1 mi
- 10/10Litchfield High SchoolGrades: 9-12Distance: 1 mi
Schools provided by the listing agent
- Elementary: Litchfield Center School
- High: Lakeview High School
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- Litchfield County
- Litchfield
- 06759
- 44 South Street
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