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49 Redhead Hill Road

Woodstock, Connecticut 06281

COMING SOON - NEW$1,350,000
Beds
4
Baths
2
SqFt
3,030
Acres
128.00
Year Built
1800
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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3-Car Garage8 Fireplaces

About This Home

OFFERED TO THE PUBLIC FOR THE FIRST TIME IN OVER 75 YEARS! A rare opportunity to own a remarkable piece of New England history. Held within the same family for generations, this extraordinary property encompasses approximately 128 acres of rolling fields, mature woodlands, historic stone walls, and breathtaking countryside views. Dating back to before the signing of "THE DECLARATION OF INDEPENDANCE" this historic homestead and former dairy farm offer a combination of history, character, and land that is increasingly difficult to find. The home makes a memorable first impression with its impressive original front door, complete with distinctive pressed hardware and framed by beautiful surrounding stained glass. Inside, you'll find a blend of historic charm, thoughtful updates, and opportunities to make the home your own. The main level offers two formal sitting rooms, a dedicated office space, and an eat-in kitchen featuring a substantial wood stove and impressive hearth. A full bathroom is also conveniently located on the main level. Upstairs, you'll find four bedrooms, each featuring its own decorative fireplace mantel, adding to the home's historic character. One bedroom is currently being used as a laundry room but can easily be converted back to a bedroom. A beautifully renovated full bathroom completes the second floor, featuring tile flooring and a tiled tub and shower.

Key Facts

City/Town
Woodstock
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1800
Days on Market
0 days
Beds
4
Baths
2 full
Living Area
3,030 sq ft
Lot Size
128.00 acres
Garage / Parking
3 garage
Property Taxes
$8,210 / Annually

Market Snapshot

The Woodstock Market

Single Family · trailing 12 months

Median Days on Market

65

20 active listings

Median $ / Sq Ft

$282

20 active listings

Sale-to-List Ratio

100.0%

100 sales

How this home compares

List Price

$1.35M

vs $572,450 median

2.4× the median

Price / Sq Ft

$446

vs $282 median

58.2% above median

Days on Market

0 days

vs 65 days median

65 days fresher than median

Based on 20 active and 100 closed sales (trailing 12 mo) of single family in Woodstock. Source: SmartMLS · As of November 11, 2026.

Location

49 Redhead Hill Road, Woodstock, Connecticut

Property + 4 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$8,450

per month

  • Principal & Interest$7,316
  • Property Taxes$684
  • Insurance$450
  • HOA$0

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

Location

City/Town
Woodstock
Neighborhood
N/A
County
Windham

Residence

Property Type
Single Family
Style
Colonial
Year Built
1800
New Construction
No/Resale
Living Area
3,030 sq ft

Schools

Elementary
Per Board of Ed
Middle
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
None
Fireplaces
8
Appliances
Gas CooktopOven/RangeRefrigeratorFreezerWasherElectric Dryer
Basement
Full

Exterior & Lot

Lot Size
128.00 acres
Zoning
0
Garage / Parking
3 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Vinyl Siding
Color
Blue
Roof
Asphalt Shingle
Foundation
Stone
Exterior Features
BreezewayBarnGarden AreaStone Wall
Lot Description
SecludedLightly WoodedFarm LandClearedWater ViewOpen Lot

Listing & Financials

Property Taxes
$8,210 / Annually
Days on Market
0
MLS #
24220572
MLS Status
Coming Soon

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Listed By

Sheena Ruggirello

(860) 222-4734

Real Broker CT, LLC

(855) 450-0442

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

The IDX display contains information sourced from SmartMLS, Inc. as of 11/11/2026. 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 11/11/2026 at 6:16 PM UTC.