Recently Viewed Properties
See This Home
Save This Listing
Close

$995,000

  • Sold
  • Closed
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 2 Partial Baths
  • 2,804 Sq. Ft.
  • 2 Car Garage
See This Home
Save This Home
See This Home
Save This Home
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

  • Sold For: $995,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24097497
  • Added to Site: 504 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
Sold by William Pitt Sotheby's Int'l, THE KATHRYN CLAIR TEAM, Kathryn Clair

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 ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 286 South St

Date
Details
Price
Change
Source
9/11/2026
Sold
$995,000
—
MLS
5/20/2026
Price Reduced
$995,000
-5.15%
MLS
4/27/2026
Price Reduced
$1,049,000
-4.2%
MLS
11/21/2025
Price Reduced
$1,095,000
-8.37%
MLS
5/20/2025
Listed
$1,195,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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

Similar Properties near 286 South St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

336 South St, Roxbury, CT 06783 - Photo 1
$998,000

336 South St  Roxbury, CT 06783

  • Single Family
  • Active
  • Updated 10 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,556
    Sq. Ft.
Listed by Redfin Corporation
24 Hickory Ln, Roxbury, CT 06783 - Photo 1
$925,000

24 Hickory Ln  Roxbury, CT 06783

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 3,340
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
282 Tepi Dr, Southbury, CT 06488 - Photo 1
$995,000

282 Tepi Dr  Southbury, CT 06488

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 4,144
    Sq. Ft.
Listed by Regency Real Estate, LLC
50 Southbury Rd, Roxbury, CT 06783 - Photo 1
$950,000

50 Southbury Rd  Roxbury, CT 06783

  • Single Family
  • Active
  • Updated 8 days ago
  • 5
    Beds
  • 3
    Total Baths
  • 1,959
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l

Just Listed near 286 South St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

63 Main St N, Woodbury, CT 06798 - Photo 1 Just Listed
$849,900

63 Main St N  Woodbury, CT 06798

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,662
    Sq. Ft.
Listed by Klemm Real Estate Inc
74 Washington Rd, Woodbury, CT 06798 - Photo 1 Just Listed
$290,000

74 Washington Rd  #40  Woodbury, CT 06798

  • Townhouse
  • Active
  • Updated 3 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,430
    Sq. Ft.
Listed by LPT Realty - IConn Team
65 W Shore Rd, Washington, CT 06777 - Photo 1 Just Listed
$1,995,000

65 W Shore Rd  Washington, CT 06777

  • Single Family
  • Active
  • Updated 14 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 2,475
    Sq. Ft.
Listed by Klemm Real Estate Inc
164 Quanopaug Trail, Woodbury, CT 06798 - Photo 1 Just Listed
$550,000

164 Quanopaug Trail  Woodbury, CT 06798

  • Single Family
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,796
    Sq. Ft.
Listed by Vitale Realty

Price Reduced near 286 South St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1917 Main St N, Woodbury, CT 06798 - Photo 1 Price Reduced
-$15,000 (-1.76%)
$835,000

1917 Main St N  Woodbury, CT 06798

  • Single Family
  • Active
  • Updated 6 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 4,819
    Sq. Ft.
Listed by Amy Lapierre (203) 903-1950
153 Old Sherman Hill Rd, Woodbury, CT 06798 - Photo 1 Price Reduced
-$100,000 (-16.67%)
$499,900

153 Old Sherman Hill Rd  Woodbury, CT 06798

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,658
    Sq. Ft.
Listed by Heather Weber (203) 232-5483
323 Upper Grassy Hill Rd, Woodbury, CT 06798 - Photo 1 Price Reduced
-$14,100 (-2.39%)
$574,900

323 Upper Grassy Hill Rd  Woodbury, CT 06798

  • Single Family
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 3,282
    Sq. Ft.
Listed by Keller Williams Realty
132 Good Hill Rd, Woodbury, CT 06798 - Photo 1 Price Reduced
-$20,000 (-2.29%)
$855,000

132 Good Hill Rd  Woodbury, CT 06798

  • Single Family
  • Active
  • Updated 10 hours ago
  • 5
    Beds
  • 4
    Total Baths
  • 4,180
    Sq. Ft.
Listed by Drakeley Real Estate, Inc.

Recent Sales near 286 South St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

28 Garnet Rd, Roxbury, CT 06783 - Photo 1 Sold
$960,000

28 Garnet Rd  Roxbury, CT 06783

  • Single Family
  • Closed
  • Updated 6 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 3,696
    Sq. Ft.
Listed by Compass Connecticut, LLC
Sold by William Raveis Real Estate
45 Chalybes Rd, Roxbury, CT 06783 - Photo 1 Sold
$850,000

45 Chalybes Rd  Roxbury, CT 06783

  • Single Family
  • Closed
  • 3
    Beds
  • 4
    Total Baths
  • 2,725
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
Sold by W. Raveis Lifestyles Realty
31 Blueberry Hill Rd, Bridgewater, CT 06752 - Photo 1 Sold
$933,155

31 Blueberry Hill Rd  Bridgewater, CT 06752

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 3,284
    Sq. Ft.
Listed and Sold by Paul Valeri, Realtors
557 Upper Grassy Hill Rd, Woodbury, CT 06798 - Photo 1 Sold
$885,000

557 Upper Grassy Hill Rd  Woodbury, CT 06798

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 3,784
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
Sold by William Raveis Real Estate

286 South Street, Roxbury, CT 06783 (MLS# 24097497) is a Single Family property that was sold at $995,000 on September 11, 2026. 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.