286 South St

Roxbury, CT 06783

$1,095,000
Price
5
Beds
2,804 Sq. Ft.
$391 / Sq. Ft.
2,804
Sq. Ft.
$391
per Sq. Ft.
an aerial view of residential houses with outdoor space and trees
a view of a big yard with lots of trees
a view of a backyard with a garden and plants
a view of a lush green space
a front view of a house with a yard table and chairs
a view of a grassy field with trees
a living room with furniture and a large window
a living room with furniture a fireplace and a flat screen tv
a living room with furniture and a fireplace
a living room with furniture and a window
a view of a dining room with furniture window and wooden floor
a kitchen with stainless steel appliances granite countertop a stove and cabinets
a view of a dining room with furniture window and wooden floor
a kitchen with a stove sink and window
a very nice looking dining room with furniture
a bedroom with a bed and cabinets
a bathroom with a sink a toilet and shower
a table chair sitting in a room next to a window
a bedroom with a bed and a window
a bathroom with a sink and a mirror
a bedroom with a bed and a window
a view of a balcony with chairs and a potted plant
a front view of a house with a yard
a kitchen with stainless steel appliances granite countertop a refrigerator oven a sink dishwasher and a stove with wooden floor
a living room with furniture and a fireplace
a dining room with furniture a large window and wooden floor
a living room with furniture and a fireplace
a bathroom with a toilet a sink and mirror
a living room with furniture fireplace and flat screen tv
a bedroom with furniture and a window
a bathroom with a double vanity sink toilet and mirror
a view of a house with a big yard and potted plants
a view of an entryway with staircase
a bathroom with a granite countertop sink and a mirror
a view of front of a house with a yard
a view of a trees in a field

Description

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...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.
  1. Listed by Kathryn Clair • William Pitt Sotheby's Int'l
    P: (203)-948-5255 C: (203)-948-5255 kclair@wpsir.com
  2. Listed by Kathryn C Bassett • William Pitt Sotheby's Int'l
    P: (860)-868-6600 C: (203)-841-8161 kcbassett@wpsir.com

Property Details for 286 South Street

Basement Description
Crawl Space
Direct Waterfront
Yes
Garages Number
2
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Attached Garage, Driveway
Swimming Pool
Yes
LISTING UPDATED: 11/21/2025 04:04 PM

Property Details for 286 South Street

StatusActive
MLS #24097497
Days on Market218
Taxes$7,036 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1977
Lot Size8.40 AC / 365,904 SF
CountyLitchfield County

Location

Listing Courtesy of William Pitt Sotheby's Int'l, Kathryn Clair; William Pitt Sotheby's Int'l, Kathryn C Bassett
Add your commute

Building Information for 286 South Street

Stories-Year Built1977Building Size-Lot Size8.40 AC / 365,904 SF

Payment Calculator

$5,997 per month

30 year fixed, 6.28% Interest

Principal and Interest

$5,411

Property Taxes

$586

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 286 South Street

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: South Street to 286 on Left. Long level driveway in to the home and guest house.
  • Elementary School: Booth Free
  • High School: Regional District 12
  • Latitude: 41.518851
  • Longitude: -73.306005
  • Neighborhood Amenities: Golf Course, Health Club, Lake, Library, Medical Facilities, Park, Private School(s), Tennis Courts
  • State: Connecticut
Parking
  • Parking Total Spaces: 8
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $7,036
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch, Garden Area, Guest House
  • Pool Description: Vinyl, In Ground Pool
  • Waterfront Description: Brook
Interior Features
  • Appliances Included: Oven/Range, Range Hood, Refrigerator
  • Attic Description: Access Via Hatch
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Interior Features: Auto Garage Door Opener, Cable - Available, Open Floor Plan
  • Laundry Room Info: Main Level
  • Laundry Room Location: off kitchen
  • Rooms Additional: Foyer, Solarium, Staff Quarters
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 14.0
Room 2
  • Room Entry Order: 10
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 16.0
Room 3
  • Room Entry Order: 11
  • Room Length: 13.0
  • Room Level: Main
  • Room Type: Sun Room
  • Room Width: 11.0
Room 4
  • Room Entry Order: 2
  • Room Length: 13.0
  • Room Level: Main
  • Room Type: Formal Dining Room
  • Room Width: 12.0
Room 5
  • Listing Key: 3596AFF3496392AEE063E201100AB092
  • Room Entry Order: 3
  • Room Length: 21.0
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 10.0
Room 6
  • Room Entry Order: 4
  • Room Level: Main
  • Room Type: Living Room
Room 7
  • Room Entry Order: 5
  • Room Level: Main
  • Room Type: Kitchen
Room 8
  • Room Entry Order: 6
  • Room Length: 12.5
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 16.0
Room 9
  • Listing Key: 3596AFF3496392AEE063E201100AB092
  • Room Entry Order: 7
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 10
  • Room Entry Order: 8
  • Room Length: 11.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Room 11
  • Room Entry Order: 9
  • Room Length: 10.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 11.0
Property
Property and Assessments
  • Color: Gray
  • Construction Description: Frame
  • Driveway Type: Private, Unpaved
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Block, Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle, Fiberglass Shingle
  • Year Built: 1977
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Detached, Separate Entry
  • In Law Apartment: Yes
  • Sq Ft Description: first and second floors, guest house not included
  • Living Area SQFT Per Public Records: 2804
Lot Information
  • Lot Description: Secluded, Some Wetlands, Level Lot, Water View, Open Lot
  • Parcel Number: 866200
  • Sq Ft Est Heated Above Grade: 2804.0
  • Sq Ft Total: 2804.0
  • Zoning: res
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Public Records for 286 South Street

Taxable ValueLand$202,440Additions$338,800Total$541,240
Tax Record2024$7,036 ($586 / month)
Home Facts
Beds5Baths2.5Total Finished SqFt2,804 SqFtAbove Grade Finished SqFt2,804 SqFtStories2Lot Size365,904 SqFtStyleSingle Family ResidenceYear Built1977Year Renovated2005ZoningCCountyLITCHFIELDAPNRXBY M:15 L:27Fireplace TypeHas Fireplace

Schools near 286 South Street

This home is within Regional School District 12.
Rating
School
Type
Grades
Distance
Booth Free School
Public - K to 5
Shepaug Valley School
Public - 6 to 12
The Burnham School
Public - K to 5
Rating
School
Distance
Booth Free School
PublicK to 5

Shepaug Valley School
Public6 to 12

The Burnham School
PublicK to 5

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 286 South Street, Roxbury, CT 06783

286 South Street is a single family home for sale in Roxbury, CT 06783. This property was listed for sale on May 20, 2025 by William Pitt Sotheby's Int'l, it's currently listed at $1,095,000. This listing's school district is Regional School District 12. Nearby schools include Booth Free School, Shepaug Valley School and The Burnham School. 286 South Street is a 5-bed, 5-bath, 2,804 sqft single family home built in 1977.

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, Kathryn Clair; William Pitt Sotheby's Int'l, Kathryn C Bassett

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.