49 Redhead Hill Road
Woodstock, Connecticut 06281
- Beds
- 4
- Baths
- 2
- SqFt
- 3,030
- Acres
- 128.00
- Year Built
- 1800
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
20
13 under contract
Median List Price
$572,450
20 active listings
Median Closed Price
$417,500
100 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per 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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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.