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99 Carriage Lane

Roxbury, Connecticut 06783

ACTIVE$1,495,000

Reduced from $1,735,000

Beds
4
Baths
2 | 1
SqFt
6,395
Acres
3.79
Year Built
2005
Matt Caiola

Matt Caiola

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About This Home

Welcome to 99 Carriage Lane, a private Roxbury estate offering over 6,000 square feet of refined living space, exceptional privacy on nearly four acres, and the opportunity to create a true resort-style outdoor retreat with approved pool plans. Set at the end of a quiet cul-de-sac, this beautifully renovated residence blends timeless architectural details with modern amenities and sophisticated country living. Designed for both comfortable everyday living and effortless entertaining, the home features a stunning chef's kitchen, dramatic family room with soaring ceilings, multiple fireplaces, spacious bedroom suites, and thoughtfully designed living spaces throughout. The expansive interiors provide flexibility for today's lifestyle, including dedicated areas for work, relaxation, and gathering with family and friends. The private grounds offer a peaceful backdrop with mature landscaping, stonework, and room to bring the outdoor vision to life. Approved plans for an inground pool provide the opportunity to further enhance this exceptional property and create a private backyard sanctuary. Located in one of Litchfield County's most desirable communities, 99 Carriage Lane offers the perfect balance of privacy, elegance, and convenience. With nearby villages, dining, recreation, and easy access to New York City.

Key Facts

City/Town
Roxbury
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
2005
Days on Market
384 days
Beds
4
Baths
2 full · 1 half
Living Area
6,395 sq ft
Lot Size
3.79 acres
Garage / Parking
3 garage · 10 total
Property Taxes
$11,959 / 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

$1.50M

vs $1.30M median

15.2% above median

Price / Sq Ft

$234

vs $506 median

53.8% below median

Days on Market

384 days

vs 88 days median

296 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

99 Carriage Lane, Roxbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$9,118

per month

  • Principal & Interest$7,623
  • Property Taxes$997
  • Insurance$498
  • 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
2005
New Construction
No/Resale
Living Area
6,395 sq ft
Below Grade
1,952 sq ft

Schools

Elementary
Booth Free
Middle
Per Board of Ed
High
Shepaug

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
4
Laundry
Main Level
Laundry Location
Mud Room
Appliances
Gas CooktopWall OvenMicrowaveRange HoodRefrigeratorFreezerSubzeroDishwasherInstant Hot Water TapWasherElectric Dryer
Basement
Full
Interior Features
Audio SystemAuto Garage Door OpenerCable - AvailableCentral VacuumHumidifier
Additional Rooms
FoyerLaundry RoomMud Room

Exterior & Lot

Lot Size
3.79 acres
Zoning
residential
Garage / Parking
3 garage spaces10 total parking spacesAttached GaragePavedDrivewayPrivateGravel
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
StoneStucco
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Lightly WoodedOn Cul-De-Sac

Listing & Financials

Property Taxes
$11,959 / Annually
Days on Market
384
MLS #
24110013
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Debra Tricarico

(914) 592-3444

Houlihan Lawrence

(203) 746-6565

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 7:05 AM UTC.