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277 Chestnut Land Road

New Milford, Connecticut 06776

ACTIVE$767,700

Reduced from $817,000

Beds
4
Baths
3 | 1
SqFt
2,836
Acres
1.88
Year Built
1977
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Pool2-Car Garage1 FireplacePrice Reduced

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,766

per 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

Similar Properties

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

Listed By

Leigh Ann Lengyel

(203) 984-5880

RE/MAX Heritage

(203) 254-7555

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.