Skip to main content

168 Cobble Road

Kent, Connecticut 06757

ACTIVE$1,650,000

Reduced from $1,795,000

Beds
4
Baths
4 | 1
SqFt
3,790
Acres
14.45
Year Built
2004
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt
2-Car Garage1 FireplacePrice Reduced

About This Home

Escape to this mountaintop retreat with sweeping, unobstructed views located off one of the most desirable scenic roads in the Litchfield Hills. Set in complete privacy, this four-bedroom home offers a perfect blend of comfort and sophistication with an open-concept layout designed for both relaxation and entertaining. The chef's kitchen, featuring a central island, flows seamlessly into a cozy reading nook with fireplace, a screened porch, and a dining area that opens to an expansive deck overlooking the breathtaking vistas. The spacious living room, anchored by a striking fieldstone fireplace, also connects to the deck and includes a charming home office. Upstairs, the primary suite offers a private balcony, spa-like bath with soaking tub, and walk-in closet. An additional ensuite bedroom, two more bedrooms with a shared full bath, and convenient laundry complete the upper level. The walkout lower level provides versatile living space, currently used as a media room and gym, and includes a full bath. Located just minutes from the shops and restaurants of Kent's vibrant village center-and only two hours from New York City-this property is the ultimate country retreat.

Key Facts

City/Town
Kent
Neighborhood
N/A
Property / Style
Single Family · Colonial,Contemporary
Year Built
2004
Days on Market
299 days
Beds
4
Baths
4 full · 1 half
Living Area
3,790 sq ft
Lot Size
14.45 acres
Garage / Parking
2 garage
Property Taxes
$12,330 / Annually

Market Snapshot

The Kent Market

Single Family · trailing 12 months

Median Days on Market

70

17 active listings

Median $ / Sq Ft

$435

17 active listings

Sale-to-List Ratio

98.0%

28 sales

How this home compares

List Price

$1.65M

vs $1.14M median

44.9% above median

Price / Sq Ft

$435

vs $435 median

In line with median

Days on Market

299 days

vs 70 days median

229 days longer than median

Based on 17 active and 28 closed sales (trailing 12 mo) of single family in Kent. Source: SmartMLS · As of July 29, 2026.

Location

168 Cobble Road, Kent, Connecticut

Property + 10 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$9,991

per month

  • Principal & Interest$8,413
  • Property Taxes$1,028
  • Insurance$550
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Kent
Neighborhood
N/A
County
Litchfield

Residence

Property Type
Single Family
Style
Colonial,Contemporary
Year Built
2004
New Construction
No/Resale
Living Area
3,790 sq ft
Below Grade
800 sq ft

Schools

Elementary
Kent
High
Housatonic

Interior

Heating
Hot Air
Heat Fuel
Propane
Cooling
Central Air
Fireplaces
1
Laundry Location
Upper Lower
Appliances
Oven/RangeRefrigeratorDishwasherWasherDryer
Basement
FullHeatedPartially FinishedFull With Walk-Out

Exterior & Lot

Lot Size
14.45 acres
Zoning
Residential
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Clapboard
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
SecludedRear LotLightly WoodedSloping Lot

Listing & Financials

Property Taxes
$12,330 / Annually
Days on Market
299
MLS #
24130930
MLS Status
Active

Similar Properties

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

Listed By

Stephen Pener

(203) 470-0393

William Pitt Sotheby's Int'l

(860) 927-1141

Co-Listed By

Vanessa Henderson

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 7/29/2026. 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 7/29/2026 at 10:10 AM UTC.