277 Chestnut Land Road
New Milford, Connecticut 06776
Reduced from $817,000
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 2,836
- Acres
- 1.88
- Year Built
- 1977
- Neighborhood
- Northville
- Property Type
- Single Family

Matt Caiola
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About This Home
Welcome to 277 Chestnut Land Road, where timeless New England charm meets modern versatility on nearly two private acres. Tucked away in one of New Milford's most desirable settings, this beautifully maintained Colonial offers the perfect blend of comfort, privacy, and endless possibilities. The thoughtfully designed floor plan features a sought after main-level primary suite, providing convenience and privacy for everyday living. Sunlight pours through the spacious living areas, where a welcoming fireplace and seamless flow create the perfect backdrop for entertaining or relaxing at home. The finished lower level expands your living options with an additional bedroom and flexible space ideal for guests, a home office, gym, media room, or playroom. An unfinished addition offers an incredible opportunity to customize the home to fit your needs, whether you envision an expansive family room, recreation space, workshop, or private guest or multigenerational living area. Outside, enjoy the beauty and serenity of nearly two acres of level property surrounded by mature trees and picturesque landscaping. There's plenty of room to entertain, garden, play, or simply unwind while taking in the peaceful surroundings. The above-ground pool can be relocated closer to the home, allowing you to create an even more inviting outdoor entertaining space. Ideally located just minutes from New Milford's vibrant town center, Candlewood Lake, shopping, restaurants, and parks.
Key Facts
- City/Town
- New Milford
- Neighborhood
- Northville
- Property / Style
- Single Family · Colonial
- Year Built
- 1977
- Days on Market
- 26 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 2,836 sq ft
- Lot Size
- 1.88 acres
- Garage / Parking
- 2 garage · 6 total
- Property Taxes
- $7,148 / 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
$767,700
vs $609,450 median
26.0% above median
Price / Sq Ft
$271
vs $290 median
6.6% below median
Days on Market
26 days
vs 39 days median
13 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
277 Chestnut Land Road, New Milford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,914
- Property Taxes$596
- Insurance$256
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- New Milford
- Neighborhood
- Northville
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1977
- New Construction
- No/Resale
- Living Area
- 2,836 sq ft
- Below Grade
- 500 sq ft
Schools
- Elementary
- Northville
- Middle
- Sarah Noble Intermediate Schoo
- High
- New Milford
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- None
- Fireplaces
- 1
- Laundry
- Lower Level
- Laundry Location
- Basement
- Appliances
- Electric CooktopMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullHeatedStorageFully FinishedInterior AccessLiveable SpaceFull With Walk-Out
- In-Law Apartment
- PossibleSeparate Entry
Exterior & Lot
- Lot Size
- 1.88 acres
- Zoning
- R60
- Garage / Parking
- 2 garage spaces6 total parking spacesAttached GaragePavedDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- Above Ground Pool
- Construction
- Vinyl Siding
- Color
- Blue
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- PorchDeckGarden AreaPatio
- Lot Description
- Lightly WoodedTreedLevel Lot
Listing & Financials
- Property Taxes
- $7,148 / Annually
- Days on Market
- 26
- MLS #
- 24188544
- 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 7/28/2026. 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 4:25 AM UTC.