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139 Grantville Road

Winchester, Connecticut 06098

ACTIVE - NEW$950,000
Beds
3
Baths
4 | 1
SqFt
4,212
Acres
67.00
Year Built
1830
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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Waterfront2-Car Garage4 Fireplaces

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

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

Property + 4 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,345

per 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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Listed By

Richard Dalton

(646) 389-3701

Country House Realty CT Inc.

(845) 397-2590

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.