336 South Street
Roxbury, Connecticut 06783
Reduced from $1,075,000
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,556
- Acres
- 4.33
- Year Built
- 1989
- Neighborhood
- Roxbury Falls
- 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
Beautiful 4 bedroom, 2.5-bath Colonial set on a picturesque, park-like property in desirable southern Roxbury. A dramatic two-story foyer welcomes you into a thoughtfully designed layout featuring a formal dining room, a spacious living room with custom built-in bookshelves, and an impressive family room highlighted by a floor-to-ceiling fireplace and custom built-ins. The kitchen is well-appointed with granite countertops, a center island, a Sub-Zero refrigerator and French doors that open seamlessly to an expansive deck and terrace-ideal for indoor-outdoor living and entertaining. Overlooking the beautifully landscaped grounds, the outdoor space features an in-ground pool, mature gardens, and lush plantings that create a private retreat-like setting. Additional highlights include ~300k in upgrades, beautiful hardwood floors throughout, a whole-house Generac generator, partially furnished with new furniture included, two-car garage underneath, an expanded driveway (30k), and a charming stone walkway that enhance the property's natural beauty. For those seeking a touch of homestead living, the property also features a professionally built chicken coop - perfect for raising chickens and enjoying fresh eggs at home. A rare opportunity to enjoy tranquility, space, and convenience, just 90 minutes from NYC.
Key Facts
- City/Town
- Roxbury
- Neighborhood
- Roxbury Falls
- Property / Style
- Single Family · Colonial
- Year Built
- 1989
- Days on Market
- 90 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,556 sq ft
- Lot Size
- 4.33 acres
- Garage / Parking
- 2 garage · 6 total
- Property Taxes
- $7,033 / 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
$998,000
vs $1.30M median
23.1% below median
Price / Sq Ft
$390
vs $506 median
22.9% below median
Days on Market
90 days
vs 88 days median
In line with 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
336 South Street, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$5,089
- Property Taxes$586
- Insurance$333
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Roxbury
- Neighborhood
- Roxbury Falls
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1989
- New Construction
- No/Resale
- Living Area
- 2,556 sq ft
Schools
- Elementary
- Booth Free
- Middle
- Per Board of Ed
- High
- Shepaug
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- Room dimension: 9.4 x 9.9
- Appliances
- Oven/RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- Partial
- Interior Features
- Cable - Pre-wired
Exterior & Lot
- Lot Size
- 4.33 acres
- Zoning
- C
- Garage / Parking
- 2 garage spaces6 total parking spacesAttached GarageOff Street ParkingDrivewayPaved
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- In Ground Pool
- Construction
- Clapboard
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Underground UtilitiesPatio
- Lot Description
- Some WetlandsLevel Lot
Listing & Financials
- Property Taxes
- $7,033 / Annually
- Days on Market
- 90
- MLS #
- 24169438
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
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 12:15 PM UTC.