142 Stilson Hill Road
New Milford, Connecticut 06776
- Beds
- 2
- Baths
- 3
- SqFt
- 3,144
- Acres
- 12.81
- Year Built
- 1986
- Neighborhood
- Stilson Heights
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
55
58 under contract
Median List Price
$599,900
55 active listings
Median Closed Price
$525,000
246 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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.