139 Grantville Road
Winchester, Connecticut 06098
- Beds
- 3
- Baths
- 4 | 1
- SqFt
- 4,212
- Acres
- 67.00
- Year Built
- 1830
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Tucked away in one of New England's most untouched pockets, Grantville Meadows presents a rare 60+ acre canvas designed for complete privacy, creative restoration, or an inspired architectural vision. Sited just over two hours from New York City and Boston, it offers an escape while keeping you minutes from the historic mill towns of Winsted and Torrington - home to cultural spots, independent shops, diverse dining, and industrial heritage. Nearby Norfolk offers live music at Yale's Music Shed and Infinity Hall, and craft brews with views at Norbrook Farm Brewery. The Berkshires and Hudson Valley are within easy reach - just 7 miles to the Massachusetts border. Bordered by conserved Nature Conservancy land and the Mad River, the setting delivers total seclusion. The land unfolds across rolling meadows, antique stone walls, tapped sugar maples, woodland trails, and a natural swimming hole. At the edge of the grounds stands an antique farmhouse. Brimming with irreplaceable character, it features wide-plank floors, four fireplaces, and bay windows framing sweeping pastoral views. Whether you restore the antique home or build a bold retreat along the ridge-line, the groundwork is done. Perc tests and perimeter surveys are complete, alongside a 30 kW solar array with battery storage generating a substantial surplus. Hold over 60 acres as a sanctuary, tap syrup, or run the organic farm. Grantville Meadows is a rare chance to build something lasting in Litchfield County.
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1830
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 4 full · 1 half
- Living Area
- 4,212 sq ft
- Lot Size
- 67.00 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $9,186 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
20
17 under contract
Median List Price
$415,000
20 active listings
Median Closed Price
$341,000
89 sales
Median Days on Market
46
20 active listings
Median $ / Sq Ft
$241
20 active listings
Sale-to-List Ratio
100.0%
89 sales
How this home compares
List Price
$950,000
vs $415,000 median
2.3× the median
Price / Sq Ft
$226
vs $241 median
6.2% below median
Days on Market
0 days
vs 46 days median
46 days fresher than median
Based on 20 active and 89 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of October 15, 2026.
Location
139 Grantville Road, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per month
- Principal & Interest$5,262
- Property Taxes$766
- Insurance$317
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1830
- New Construction
- No/Resale
- Living Area
- 4,212 sq ft
- Below Grade
- 1,340 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- No Heat
- Cooling
- None
- Fireplaces
- 4
- Appliances
- None
- Basement
- PartialPartially Finished
- In-Law Apartment
- PossibleSeparate Entry
- Interior Features
- Cable - Available
- Additional Rooms
- Staff Quarters
Exterior & Lot
- Lot Size
- 67.00 acres
- Zoning
- RR
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- RiverWalk to Water
- Water Source
- Private Well
- Sewer
- None
- Flood Zone
- No
- Construction
- Clapboard
- Color
- White
- Roof
- Shingle
- Foundation
- Stone
- Exterior Features
- Fruit TreesStone WallFrench DoorsPaddock
- Lot Description
- SecludedFarm LandRolling
Listing & Financials
- Property Taxes
- $9,186 / Annually
- Days on Market
- 0
- MLS #
- 24213967
- 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 10/15/2026. 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 10/15/2026 at 2:25 AM UTC.