142 Second Hill Road
New Milford, Connecticut 06776
- Beds
- 3
- Baths
- 3 | 1
- SqFt
- 2,866
- Acres
- 2.00
- Year Built
- 1948
- Neighborhood
- Second Hill
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
This quintessential Connecticut home with over $240K improvements is nestled on a picturesque very private 2-acre lot bordering the scenic 150- acre Second Hill Reservoir and preserve. This beautifully updated Cape featuring handsome stonework warming both the exterior and interior offers the perfect blend of privacy, nature, and convenience. With 3 bedrooms, 3.5 baths, this home features a flexible floor plan ideal for full-time living or a weekend retreat. The spacious living room with 10-foot ceilings showcases hardwood floors and a stunning stone fireplace, while the bright sunroom invites year-round enjoyment of the surrounding landscape. Two main-level bedrooms offer private full baths, including a primary suite with direct access to the sunroom. Upstairs, an additional bedroom and full bath provide excellent guest accommodation and peaceful hillside views. The partially finished walk-out lower level offers abundant space for recreation, hobbies, or a home office. An oversized detached two-car garage and level backyard complete the package. Located just minutes from New Milford's charming town green, shopping, dining, and hospital, this property is a rare opportunity to enjoy country living with modern convenience. Walking trails, kayaking, fishing, and the beauty of the reservoir are right outside your French doors.
Key Facts
- City/Town
- New Milford
- Neighborhood
- Second Hill
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1948
- Days on Market
- 3 days
- Beds
- 3
- Baths
- 3 full · 1 half
- Living Area
- 2,866 sq ft
- Lot Size
- 2.00 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $7,706 / Annually
Market Snapshot
The New Milford Market
Single Family · trailing 12 months
Active Listings
56
56 under contract
Median List Price
$609,450
56 active listings
Median Closed Price
$525,000
246 sales
Median Days on Market
39
56 active listings
Median $ / Sq Ft
$290
56 active listings
Sale-to-List Ratio
100.0%
246 sales
How this home compares
List Price
$829,500
vs $609,450 median
36.1% above median
Price / Sq Ft
$289
vs $290 median
In line with median
Days on Market
3 days
vs 39 days median
36 days fresher than median
Based on 56 active and 246 closed sales (trailing 12 mo) of single family in New Milford. Source: SmartMLS · As of July 28, 2026.
Location
142 Second Hill Road, New Milford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,229
- Property Taxes$642
- Insurance$277
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- New Milford
- Neighborhood
- Second Hill
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 1948
- New Construction
- No/Resale
- Living Area
- 2,866 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Heat Pump
- Heat Fuel
- Electric
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- Electric CooktopWall OvenMicrowaveRefrigerator
- Basement
- Crawl SpaceFull
- In-Law Apartment
- PossibleSeparate Entry
Exterior & Lot
- Lot Size
- 2.00 acres
- Zoning
- R80
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Level LotSloping LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $7,706 / Annually
- Days on Market
- 3
- MLS #
- 24194207
- MLS Status
- Coming Soon
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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 7/28/2026. 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 6:55 AM UTC.