57 Indian Trail Road
New Milford, Connecticut 06776
- Beds
- 4
- Baths
- 3 | 2
- SqFt
- 6,236
- Acres
- 72.00
- Year Built
- 1755
- Neighborhood
- Lower Merryall
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
57
57 under contract
Median List Price
$599,900
57 active listings
Median Closed Price
$525,000
245 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 30, 2026per 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
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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.