49 Redhead Hill Road Woodstock, CT $ 1,350,000
49 Redhead Hill Road
$ 1,350,000
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49 Redhead Hill Road

Woodstock, CT, 06281
$ 1,350,000
Bedrooms4 Baths2.0 Sq 3,030

Monthly Estimate*

$ 9,324

49 Redhead Hill Road, Woodstock, CT 06281 - Image 1

Single Family Home for sale in Woodstock, CT

for $1,350,000 with 4 bedrooms and 2 full baths. This 3,030 square foot home was built in 1800 on a lot size of 128.

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. A newer mudroom addition provides convenient everyday functionality and connects through a breezeway to the impressive oversized garage. With its distinctive three-bay configuration, including two front-facing bays and an additional side bay with an oversized door, the garage offers exceptional space and versatility. Above the garage, the existing truss configuration was designed to allow for the possibility of creating additional living space in the future. The once working dairy barn has 2 levels, with the main level already undergone restoration, it still stands strong and stately. Beyond the farmhouse, the landscape is truly extraordinary. Expansive fields, mature woodlands, historic stone walls, and gently rolling hills create a breathtaking setting. The individually named fields that lead to an elevated vantage point where views stretch across three states: Connecticut, Massachusetts, and Rhode Island. Whether you envision a private estate, historic homestead, agricultural retreat, or simply the opportunity to preserve and enjoy a remarkable piece of New England history, this property offers a setting and scale that are rarely available. A truly special opportunity to own a piece of the past while creating something lasting for the future.

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Single Family Coming Soon

Price

$ 1,350,000

Bedrooms

4

Full Bath

2

Property Type

Single Family

Taxes

$ 8,210

Style

Lot Size

128

Year Built

1800

Town/City

Woodstock

MLS | Web ID

24220572

Features
General
Zoning 0
Neighborhood N/A
County Windham
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Coming Soon
Acres 128
Directions GPS Friendly
High School Per Board of Ed
City Woodstock
Elementary School Per Board of Ed
Sq Ft Total 3030
Year Built 1800
Style Colonial
Year Built Source Public Records
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Interior
Cooling System None
Total Rooms 8
Basement Description Full
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Exterior
Water Source Private Well
Lot Description Secluded Lightly Wooded Farm Land Cleared Water View Open Lot
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* Excluded Features
List By
Sheena Ruggirello

Listing Agent

Real Broker Ct, Llc

Broker

sheena.ruggirellos@gmail.com

Email

Affordability Calculator

$10,008
Per Month
93%
7%
0%
Monthly Principal & Interest
$9,324
Monthly Property Taxes
$684
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History
DatePricePrice ChangeDescription
11/11/2026$1,350,000 Listed Price

Map


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49 Redhead Hill Road, Woodstock, CT, 06281 is a Single Family Home for sale at $1,350,000 with 3,030 sqft and a lot size of 128. 49 Redhead Hill Road has 4 bedrooms, 2.0 baths, and was built in 1800. The property's zip code is 06281 which is in Woodstock, CT