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57 Indian Trail Road

New Milford, Connecticut 06776

ACTIVE$5,245,000
Beds
4
Baths
3 | 2
SqFt
6,236
Acres
72.00
Year Built
1755
Matt Caiola

Matt Caiola

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WaterfrontGuest HouseWine CellarPool4-Car Garage3 Fireplaces

About This Home

"Hollow Farm" - An Expansive Historic Estate Reimagined for Modern Country Living Nestled in its own private valley, this 72-acre estate includes a Main House, thoughtfully updated and expanded in 2005; a charming Guest Bungalow; screened Gazebo perched over a pond; Pool Pavilion; Stables with caretaker's apartment; and a restored Barn. Comprised of multiple parcels, offering maximum privacy. The circa-1755 Main House features a dramatic great room with stone fireplace, adjoining chef's kitchen, and formal dining room. Additional main-level spaces include both a sitting room and a library with back-to-back fireplaces, plus a guest suite with full bath and sitting room. Upstairs, the primary suite offers a lofted sitting area with fireplace, as well as private deck, while two guest bedrooms share a hall bath. The lower level includes a wine cellar with cobbled floor and a gym. Outside, multi-level terraces showcase exceptional stonework, a fire pit, grilling area, pool, and spa. Two ponds and the sparkling Merryall Brook enhance the 18 acres of open land. Extensive landscaping compliments the natural beauty of the forested hills. As with the Main House, every outbuilding and outdoor space has been meticulously maintained. Although it feels a world away, this remarkable property is only 15 minutes from Kent, New Preston, and Washington. With its historic character, modern updates and expansive private setting Hollow Farm offers a rare opportunity for refined country living

Key Facts

City/Town
New Milford
Neighborhood
Lower Merryall
Property / Style
Single Family · Antique
Year Built
1755
Days on Market
58 days
Beds
4
Baths
3 full · 2 half
Living Area
6,236 sq ft
Lot Size
72.00 acres
Garage / Parking
4 garage
Property Taxes
$43,321 / Annually

Market Snapshot

The New Milford Market

Single Family · trailing 12 months

Median Days on Market

36

57 active listings

Median $ / Sq Ft

$289

57 active listings

Sale-to-List Ratio

100.0%

245 sales

How this home compares

List Price

$5.25M

vs $599,900 median

8.7× the median

Price / Sq Ft

$841

vs $289 median

2.9× the median

Days on Market

58 days

vs 36 days median

22 days longer than median

Based on 57 active and 245 closed sales (trailing 12 mo) of single family in New Milford. Source: SmartMLS · As of August 1, 2026.

Location

57 Indian Trail Road, New Milford, Connecticut

Property + 9 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$32,323

per month

  • Principal & Interest$26,965
  • Property Taxes$3,610
  • Insurance$1,748
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
New Milford
Neighborhood
Lower Merryall
County
Litchfield

Residence

Property Type
Single Family
Style
Antique
Year Built
1755
New Construction
No/Resale
Living Area
6,236 sq ft
Below Grade
408 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot AirRadiant
Heat Fuel
OilPropane
Cooling
Central Air
Fireplaces
3
Laundry
Main Level
Laundry Location
Ground floor
Appliances
Gas RangeWall OvenRefrigeratorDishwasherWasherDryer
Basement
Crawl SpacePartial
Interior Features
Audio SystemCable - Pre-wiredSecurity System
Additional Rooms
Exercise RoomFoyerMud RoomWine CellarWorkshop

Exterior & Lot

Lot Size
72.00 acres
Zoning
R40
Garage / Parking
4 garage spacesBarnAttached Garage
Waterfront
Direct waterfront
Waterfront Details
PondBrookWalk to Water
Water Source
Private Well
Sewer
Septic
Pool
GuniteHeatedPool HouseSpaSalt WaterIn Ground Pool
Construction
Clapboard
Color
white
Roof
Wood Shingle
Foundation
ConcreteStone
Exterior Features
TerraceBarnCabanaGuest HouseHot TubFruit TreesGazeboDeckStable
Lot Description
SecludedSome WetlandsLightly WoodedTreedProfessionally LandscapedRolling

Listing & Financials

Property Taxes
$43,321 / Annually
Days on Market
58
MLS #
24176398
MLS Status
Active

Similar Properties

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

Listed By

Elyse Harney Morris

(860) 318-5126

Elyse Harney Real Estate

(860) 435-0120

Co-Listed By

Anne Peck

Elyse Harney Real Estate

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/1/2026. 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 8/1/2026 at 6:25 PM UTC.