Skip to main content

142 Second Hill Road

New Milford, Connecticut 06776

COMING SOON - NEW$829,500
Beds
3
Baths
3 | 1
SqFt
2,866
Acres
2.00
Year Built
1948
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 Garage2 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,148

per 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

Similar Properties

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

Listed By

Ken Freundt

(203) 731-0003

Coldwell Banker Realty

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.