380 Southbury Road
Roxbury, Connecticut 06783
Reduced from $1,600,000
- Beds
- 4
- Baths
- 4 | 1
- SqFt
- 4,452
- Acres
- 6.87
- Year Built
- 2003
- 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
Nestled on nearly seven private acres along a quiet country road in picturesque Roxbury, this exceptional residence offers a seamless blend of elegance, comfort, and classic New England charm. Set back from the road with a gently curving drive, the home welcomes you with a dramatic two-story foyer and grand staircase, complemented by hardwood floors, detailed millwork, crown molding, tray ceilings, and abundant natural light throughout. The gourmet kitchen features custom cherry cabinetry, granite countertops, stainless steel appliances, and a butler's pantry, opening to a warm hearth room with a fieldstone fireplace. A sunken family room with a brick fireplace and French doors leads to a stone patio, creating an ideal flow for indoor-outdoor living. The upper level offers a spacious primary suite, three additional bedrooms, three full baths, and a versatile rooms suitable for a home office, lounge, or playroom. The walk-out lower level with 9-foot ceilings provides approximately 1,950square feet of additional living space, including a recreation area, full bar, exercise room, bedroom, full bath, and flexible space for entertaining or extended living. The grounds offer a peaceful retreat with woodland trails, a stream, fire pit, outbuildings, and a two-story pool house. Additional features include a chicken coop and utility structure, enhancing the property's country lifestyle appeal. Conveniently located near local amenities while offering privacy and tranquility.
Key Facts
- City/Town
- Roxbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2003
- Days on Market
- 124 days
- Beds
- 4
- Baths
- 4 full · 1 half
- Living Area
- 4,452 sq ft
- Lot Size
- 6.87 acres
- Garage / Parking
- 3 garage · 15 total
- Property Taxes
- $9,484 / 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
$1.55M
vs $1.30M median
19.5% above median
Price / Sq Ft
$348
vs $506 median
31.2% below median
Days on Market
124 days
vs 88 days median
36 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
380 Southbury Road, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$7,903
- Property Taxes$790
- Insurance$517
- 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
- 2003
- New Construction
- No/Resale
- Living Area
- 4,452 sq ft
Schools
- Elementary
- Booth Free
- High
- Per Board of Ed
Interior
- Heating
- Hot WaterWood/Coal Stove
- Heat Fuel
- Oil
- Cooling
- Ceiling FansCentral Air
- Fireplaces
- 1
- Laundry
- Upper Level
- Laundry Location
- Upper Level2nd floor
- Appliances
- Gas RangeWall OvenMicrowaveRange HoodRefrigeratorSubzeroIcemakerDishwasherWasherElectric Dryer
- Basement
- FullFull With Walk-Out
- Interior Features
- Auto Garage Door OpenerCable - AvailableOpen Floor PlanSecurity System
- Additional Rooms
- Bonus Room
Exterior & Lot
- Lot Size
- 6.87 acres
- Zoning
- C
- Garage / Parking
- 3 garage spaces15 total parking spacesAttached GarageDrivewayUnpavedPrivateCircularUnpaved
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- Pool HouseIn Ground Pool
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Block
- Lot Description
- SecludedTreedDryLevel LotProfessionally LandscapedOpen Lot
Listing & Financials
- Property Taxes
- $9,484 / Annually
- Days on Market
- 124
- MLS #
- 24162311
- MLS Status
- Active
- Financing
- FHA,VA,CHFA
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 8:02 AM UTC.