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$1,095,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 2 Partial Baths
  • 2,804 Sq. Ft.
  • 2 Car Garage
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Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt on the southern side of Roxbury, offering an idyllic escape with seamless access to NYC. This privately situated home rests in a serene meadow, gracefully bordered by Pierce Brook. The main residence features a comfortable layout with a living room and fireplace that flows into the dining area and kitchen. Upstairs, you'll find four spacious bedrooms and two full bathrooms. A bright slate floored sunroom overlooks the inviting heated salt pool, perfect for relaxation and entertaining. Adding to its unique appeal is an attached 1-bedroom in law/guest house with propane heating and cooling, providing flexible space for visitors or extended family. The property boasts level land and lush grounds, including a expansive pasture area, all set against the picturesque backdrop of Pierce Brook. This Roxbury gem combines tranquility with convenience, making it an ideal retreat.

Full Property Details for 286 South St

General

  • Price: $1,095,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24097497
  • Updated: 11/26/2025
  • Added to Site: 241 day(s) ago

Interior

  • Number of Rooms: 9
  • Rooms/Areas: Foyer, Solarium, Staff Quarters
  • Interior Features: Auto Garage Door Opener, Cable - Available, Open Floor Plan
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Oven/Range, Range Hood, Refrigerator

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 3
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom, 12.5 x 16, Upper
  • Bedroom 1: Bedroom, 10 x 11, Upper
  • Bedroom 2: Bedroom, 11 x 13, Upper
  • Bedroom 3: Bedroom, 13 x 12, Upper
  • Bedroom 4: Bedroom, 14 x 16, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Kitchen: Kitchen, Main
  • Eat In Kitchen: Eat-In Kitchen, 21 x 10, Main
  • Formal Dining Room: Formal Dining Room, 13 x 12, Main
  • Laundry: Main Level
  • In-Law/Au Pair Suite: Yes

Additional Information

  • Pool: Yes
  • Pool Description: Vinyl, In Ground Pool

Exterior

  • Exterior Features: Porch, Garden Area, Guest House
  • Color: Gray

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 8
  • Parking: Attached Garage, Driveway

Location

  • County: Litchfield
  • Driving Directions: South Street to 286 on Left. Long level driveway in to the home and guest house.

School Information

  • Elementary School: Booth Free
  • High School: Regional District 12

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Crawl Space
  • Roof: Asphalt Shingle, Fiberglass Shingle
  • Attic: Yes
  • Square Feet: 2,804
  • Above Ground: 2,804 Sq. Ft.
  • Year Built: 1977

Lot Features

  • Lot Size (Acres): 8.4
  • Driveway/Sidewalk: Private, Unpaved
  • Zoning: res
  • Lot Description: Secluded, Some Wetlands, Level Lot, Water View, Open Lot

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Brook

Financial Considerations

  • Assessment Amount: $541,240
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 866200

Listed by William Pitt Sotheby's Int'l, THE KATHRYN CLAIR TEAM, Kathryn Clair and William Pitt Sotheby's Int'l, Kathryn Bassett

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Listing agents

— 286 South St —

  • Kathryn Clair

    William Pitt Sotheby's Int'l

  • Kathryn Bassett

    William Pitt Sotheby's Int'l

Agent Contact: (203) 948-5255 Office Contact: (860) 868-6600

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 286 South St

School District:Regional School District 12
NameGradesDistance
Shepaug Valley School
159 South Street, Washington, CT 06793
6-125.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 286 South St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/21/2025
Price Reduced
$1,095,000
-8.37%
MLS
5/20/2025
Listed
$1,195,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 286 South St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$7,036
3%
$541,240
—
2023
$6,820
7%
$541,240
30%
2022
$6,345
16%
$416,080
17%
2021
$5,484
-3%
$356,080
—
2020
$5,626
—
$356,080
—
2019
$5,644
—
$356,080
—
2018
$5,644
-7%
$356,080
-17%
2017
$6,079
4%
$428,110
—
2016
$5,865
—
$428,110
—
2015
$5,843
2%
$426,470
—
2014
$5,715
1%
$426,470
—
2012
$5,672
—
$426,470
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 286 South St

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by William Pitt Sotheby's Int'l, THE KATHRYN CLAIR TEAM, Kathryn Clair and William Pitt Sotheby's Int'l, Kathryn Bassett

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286 South Street, Roxbury, CT 06783 (MLS# 24097497) is a Single Family property with 5 bedrooms, 3 full bathrooms and 2 partial bathrooms. 286 South Street is currently listed for $1,095,000 and was received on May 20, 2025. Want to learn more about 286 South Street? Do you have questions about finding other Single Family real estate for sale in Roxbury? You can browse all Roxbury real estate or contact a Coldwell Banker agent to request more information.

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