286 South Street
Roxbury, Connecticut 06783
Reduced from $1,195,000
- Beds
- 5
- Baths
- 3 | 2
- SqFt
- 2,804
- Acres
- 8.40
- Year Built
- 1977
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About 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.
Key Facts
- City/Town
- Roxbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1977
- Days on Market
- 431 days
- Beds
- 5
- Baths
- 3 full · 2 half
- Living Area
- 2,804 sq ft
- Lot Size
- 8.40 acres
- Garage / Parking
- 2 garage · 8 total
- Property Taxes
- $7,036 / Annually
Market Snapshot
The Roxbury Market
Single Family · trailing 12 months
Active Listings
30
8 under contract
Median List Price
$1.30M
30 active listings
Median Closed Price
$1.40M
29 sales
Median Days on Market
88
30 active listings
Median $ / Sq Ft
$506
30 active listings
Sale-to-List Ratio
96.1%
29 sales
How this home compares
List Price
$995,000
vs $1.30M median
23.3% below median
Price / Sq Ft
$355
vs $506 median
29.8% below median
Days on Market
431 days
vs 88 days median
343 days longer than median
Based on 30 active and 29 closed sales (trailing 12 mo) of single family in Roxbury. Source: SmartMLS · As of July 28, 2026.
Location
286 South Street, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$5,073
- Property Taxes$586
- Insurance$332
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Roxbury
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1977
- New Construction
- No/Resale
- Living Area
- 2,804 sq ft
Schools
- Elementary
- Booth Free
- High
- Regional District 12
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Laundry Location
- off kitchen
- Appliances
- Oven/RangeRange HoodRefrigerator
- Basement
- Crawl Space
- In-Law Apartment
- YesDetachedSeparate Entry
- Interior Features
- Auto Garage Door OpenerCable - AvailableOpen Floor Plan
- Additional Rooms
- FoyerSolariumStaff Quarters
Exterior & Lot
- Lot Size
- 8.40 acres
- Zoning
- res
- Garage / Parking
- 2 garage spaces8 total parking spacesAttached GarageDrivewayPrivateUnpaved
- Waterfront
- Direct waterfront
- Waterfront Details
- Brook
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- VinylIn Ground Pool
- Construction
- Vinyl Siding
- Color
- Gray
- Roof
- Asphalt ShingleFiberglass Shingle
- Foundation
- BlockConcrete
- Exterior Features
- PorchGarden AreaGuest House
- Lot Description
- SecludedSome WetlandsLevel LotWater ViewOpen Lot
Listing & Financials
- Property Taxes
- $7,036 / Annually
- Days on Market
- 431
- MLS #
- 24097497
- MLS Status
- Under Contract
Similar Properties
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Co-Listed By
Kathryn Bassett
William Pitt Sotheby's Int'l
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/28/2026 at 11:10 AM UTC.