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336 South Street

Roxbury, Connecticut 06783

ACTIVE$998,000

Reduced from $1,075,000

Beds
4
Baths
2 | 1
SqFt
2,556
Acres
4.33
Year Built
1989
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Pool2-Car Garage1 FireplaceVirtual TourPrice Reduced

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

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

Property + 9 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,008

per 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.

Listed By

Karen Gilmore

(203) 482-9144

Redfin Corporation

(203) 349-8711

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.