175 Pulpit Rock Road

Windham County CT 06281

5104 sq. ft.

54.99 ac.

Single-Family

Last sold for $1,650,000

John Downs, last sold this property on 31 December 2025 after 557 days on market.

Overview

A once-in-a-generation opportunity. Please visit this stunning Georgian estate situated on 55 hilltop acres in desirable Woodstock, CT. Enjoy breathtaking long views all the way to Rhode Island! A few of the exceptional assets offered include an elegant in-law apartment, a large 6 stall horse barn with office, an inviting in-ground pool, and 25 acres of fenced open pasture. As you approach the home up the long, lighted driveway, you will immediately be impressed by the stunning architectural features and fine craftsmanship that characterize this home. "South Hill Farm" exudes a serene sense of historic grace and timelessness. Hallmark features of the 5,100+ sq ft of elegant living space include 10 ft high ceilings, 8 fireplaces, 4.5 baths, a den with classic cherry built-ins, a welcoming center foyer, and wide board flooring. Hand-painted murals of the Woodstock countryside by one of the finest local artists adorn the spacious dining area. You will love the views from the in-ground pool with stone patios, outdoor fireplace, pool house, and gardens perched high above the manicured estate. Above the heated 3-car garage, the newer in-law apartment provides private, unparalleled modern living for your guests. Bring your horses and animals.The picturesque barn connects to 6 paddocks with pastures and includes 6 stalls, tack room, hot/cold running water, spacious hay loft, and an upstairs office. Please visit and retreat from the stress of the city to this exquisite country estate.

Features

4 bedrooms

4 bathrooms

20 carspaces

6 garage spaces

5104 sq. ft. floor area

54.99 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Windham County over the last 12 months, the estimated median property value of 175 Pulpit Rock Road is $585k.

Median value

$585k

Estimated value range

$191.35k - $1.65m

Median days on market

Estimated value trend

-14%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Windham County. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 175 Pulpit Rock Road

2025

Sold

$1,650,000

31 Dec 2025 by John Downs, of RANDALL, REALTORS-Compass

Happy sellers in Windham County

We have insufficient information to provide an overview of customer satisfaction for Windham County. Viewing the agent profiles, reviews and sales for Windham County can provide insights for this location.