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142 Stilson Hill Road

New Milford, Connecticut 06776

ACTIVE$1,295,000
Beds
2
Baths
3
SqFt
3,144
Acres
12.81
Year Built
1986
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Tennis CourtPool6-Car Garage1 FireplaceVirtual Tour

About This Home

Set on an extraordinary 12.81-acre parcel, this one-of-a-kind estate offers a rare blend of privacy, luxury, and architectural distinction. Fully renovated from top to bottom, the home showcases exceptional craftsmanship with high-end, custom finishes and a design unlike anything you've seen before. Step inside to the main level where soaring ceilings, exposed beams, and walls of glass fill the great room with natural light, anchored by a striking fireplace. The stunning custom kitchen is both functional and beautiful, seamlessly connecting to the dining area-perfect for everyday living or entertaining. A unique lofted office space overlooks the main living area, adding character and versatility. The main level also features a thoughtfully designed full bathroom complete with a built-in sauna for a spa-like experience. The lower level offers a private retreat with a spectacular primary suite featuring a luxurious full bath, walk-in shower, and custom closet. A second bedroom includes charming built-in bunk beds, while the mudroom/laundry room is equipped with custom built-ins and a convenient bench. Step outside and enjoy resort-style living with direct access to an in-ground pool and spa, as well as an expansive deck ideal for entertaining or relaxing while taking in breathtaking long-distance views.

Key Facts

City/Town
New Milford
Neighborhood
Stilson Heights
Property / Style
Single Family · Contemporary,Modern
Year Built
1986
Days on Market
103 days
Beds
2
Baths
3 full
Living Area
3,144 sq ft
Lot Size
12.81 acres
Garage / Parking
6 garage
Property Taxes
$18,222 / Annually

Market Snapshot

The New Milford Market

Single Family · trailing 12 months

Median Days on Market

37

55 active listings

Median $ / Sq Ft

$288

55 active listings

Sale-to-List Ratio

100.0%

246 sales

How this home compares

List Price

$1.29M

vs $599,900 median

2.2× the median

Price / Sq Ft

$412

vs $288 median

43.1% above median

Days on Market

103 days

vs 37 days median

66 days longer than median

Based on 55 active and 246 closed sales (trailing 12 mo) of single family in New Milford. Source: SmartMLS · As of July 29, 2026.

Location

142 Stilson Hill Road, New Milford, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$8,554

per month

  • Principal & Interest$6,603
  • Property Taxes$1,519
  • Insurance$432
  • HOA$0

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

Location

City/Town
New Milford
Neighborhood
Stilson Heights
County
Litchfield

Residence

Property Type
Single Family
Style
Contemporary,Modern
Year Built
1986
New Construction
No/Resale
Living Area
3,144 sq ft
Below Grade
1,500 sq ft

Schools

Elementary
Per Board of Ed
High
New Milford

Interior

Heating
Hot Air
Heat Fuel
Propane
Cooling
Central Air
Fireplaces
1
Laundry
Lower Level
Laundry Location
Mudroom
Appliances
Gas RangeRange HoodRefrigeratorDishwasher
Basement
FullHeatedFully FinishedWalk-out
Interior Features
Open Floor Plan

Exterior & Lot

Lot Size
12.81 acres
Zoning
R60/R8
Garage / Parking
6 garage spacesDetached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Pool
SpaVinylIn Ground Pool
Construction
Vinyl SidingVertical Siding
Color
White
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
Tennis CourtGazeboDeckPatio
Lot Description
Level LotSloping Lot

Listing & Financials

Property Taxes
$18,222 / Annually
Days on Market
103
MLS #
24167772
MLS Status
Active

Similar Properties

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

Listed By

Cory Neumann

(203) 947-5803

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 7/29/2026. 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 12:55 PM UTC.