SoldAug 7, 2025

Bought with Shelley Drakeley from Drakeley Real Estate, Inc.

Source: SmartMLS Connecticut #24043497

44 South St, Litchfield County, CT, 06783

$1,825,000

3
4
3
3450 sq. ft.
6.17 ac.

SingleFam

30+ days on the market

Sold: Aug 7, 2025

What's around 44 South St

About this property

PETITE ESTATE:South St in the heart of Roxbury, FoxCroft is a classic 1792 Colonial farmhouse on a generous parcel of land. The property includes a heated pool, guest house, studio, 3 car garage with hayloft, and a pond, as well as remnants of its history: an old ice house and a well house. Inside, original fireplaces anchor each of the main rooms, including a large central fireplace with a bread oven. The sunroom opens to views of the surrounding trees and offers a quiet spot to read or work. Built-in shelves and exposed beams appear throughout, balancing simplicity with style.The kitchen has been updated with a six-burner Viking stove, Bosch dishwasher, and SubZero refrigerator, and connects to a butler's pantry for storage and utility. Front and back staircases lead upstairs to 3 ensuite bedrooms with lots of closet space. The primary suite includes a fireplace, walk-in closet, and a bonus room that could serve as a study or dressing room. The guest cottage, once a schoolhouse with cubbies, offers its own living space with a bedroom, sitting area, and full bath. The studio nearby includes a half bath, separate laundry, and flexible open space under high ceilings, ideal for creative, remote work or a play space. Outdoors, the land invites exploration. There are perennial gardens, a meadow, a pond that used to be Roxbury's town skating pond, and shaded paths among old trees and stone walls.FoxCroft is a place to settle in, or to get away. It's ready for its next chapter

Looking for more information on 44 South St?

Explore comparables, sales history and growth for this property.
Learn more

Similar properties sold nearby

SoldJan 30, 2026
$2,547,500
277 Painter Hill Road
Litchfield County CT 06783
3
3
10
Single-Family
Listing courtesy of W. Raveis Lifestyles Realty and Klemm Real Estate Inc
SoldNov 7, 2025
$1,195,000
158 Painter Hill Road
Litchfield County CT 06783
3
3
2
Single-Family
Listing courtesy of William Pitt Sotheby's Int'l
SoldOct 23, 2025
$1,650,000
78 Garnet Rd
Litchfield County CT 06783
3
4
2
Single-Family
Listing courtesy of E.J. Murphy Realty and William Pitt Sotheby's Int'l

Other properties sold by Shelley Drakeley

SoldDec 15, 2025
$785,000
24 Riverwalk
Branford CT 06405
2
3
2
Single-Family
Listing courtesy of Drakeley Real Estate, Inc. and Coldwell Banker Realty
SoldJul 14, 2025
$700,000
31 Woodbury Road
Watertown CT 06795
5
4
2
Single-Family
Listing courtesy of Drakeley Real Estate, Inc.
SoldJun 20, 2025
$525,000
35 Kathy Drive
Seymour CT 06483
5
2
2
Single-Family
Listing courtesy of Drakeley Real Estate, Inc. and Re/Max Right Choice

Browse properties sold in nearby areas

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the "DMCA") provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under MLS GRID IDX Rules Updated September 16, 2024 7 U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to: dmca@ratemyagent.com

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner's behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Email
© 2026 RateMyAgent