00 Town Line Road US$16,000,000

00 Town Line Road
00 Town Line Road
00 Town Line Road
00 Town Line Road

Property Price

approx. $16,000,000
approx. €14.480.496
approx. د.إ58,768,000
approx. $23,425,200
approx. $21,225,760
approx. CHF15,859,760
approx. ¥112,566,400
approx. £12,207,680
approx. $125,264,880
approx. kn107.598.816
approx. $309,228,800
approx. kr146.302.640
approx. ₽1.018.428.800
approx. kr152 035 424
approx. ฿485,712,000
approx. R234,288,080
approx. $487,560,032
approx. ₱812,576,048
approx. Kč369 768 000
approx. ₨583,999,232
approx. $21,778,880
approx. $13,334,352
approx. $12.424.000.000
approx. B/.16,000,000
approx. $32,000,000
approx. ₹1,140,686,304
approx. ¥1,739,144,000
approx. $43,240,800
approx. $24,410,704
approx. £12,207,680
approx. R$66.803.200
approx. ₪55,546,400
approx. ر.ع.6,159,808
approx. zł61 981 440
approx. $34,791,200
approx. $55.562.106.464
approx. Fr1,727,982,096
approx. $16,000,000
approx. ر.ق58,252,000
approx. ₡
approx. Ft4 788 320 000
approx. د.م.154,488,000
approx. kr.108.203.200

Real Estate Details

  • Year: 1880
  • Location: Roxbury, CT, United States
  • Address: 00 Town Line Road, Roxbury, CT 06783
  • Property type: Chalet
  • Bedrooms: 10
  • Bathrooms: 10
  • Living area: 10000 sqft (929 sqm)
  • Land area: 320.0 ac
  • Internal Reference: NZSNN4

Property Description

Greyledge Estate — one of the largest and most spectacularly situated properties in Litchfield County — is available for acquisition for the first time, in its entirety, as a pre-market opportunity ("the Estate Offering") through January 31, 2020. In the event no transaction is effected by then, each parcel and any associated view sheds will be offered for sale individually on the open market, in a sequence to be determined. 

Greyledge Estate is offered exclusively by Madonna & Phillips Group of William Pitt Sotheby's International Realty.

The Estate Offering: Executive Summary (CLICK TO VIEW FULL MARKETING DECK)

Offer price: $16M. 

320± unencumbered acres spanning eight parcels located in Bridgewater and Roxbury, Connecticut.

Offered through January 31, 2020.

Greyledge Estate sits at the gateway to the Litchfield Hills, a popular and growing second home market defined by community and rural tranquility, that is only 80 miles from New York City. The Estate is one of the most spectacularly situated properties in Litchfield County in that it occupies an elevated position on a picturesque ridge running along the border of Bridgewater and Roxbury, Connecticut.

The 320±-acre property is comprised of contiguous land parcels that are bordered by over 500 acres of perpetually protected Land Trust property to the north and to the east of the estate.

Greyledge Estate is further differentiated by its scale and scarcity as it is one of the largest parcels of unencumbered, prime land in Western Connecticut. The property offers a rare combination of near 360-degree views to the horizon, multiple elevated build sites, more than 100 acres of farm fields, woods, and approximately 25,000 square feet of beautifully maintained homes and out-buildings. 



PARCEL A/B: 125 Town Line Road, Bridgewater. 52.9± unencumbered acres comprising c.1820 historically significant main residence of 10,000 square feet, 10 bedrooms, 6.3 baths; pool house of 1,800 square feet, 2 bedrooms, 2 baths; "Top Field" of 20 unencumbered acres, comprised of open pasture, 360-degree views, and offers the Estate's most elevated build site

PARCEL C: 114 Town Line Road, Roxbury. 67.59± unencumbered acres comprising antique Dickinson Dairy House, sheds, and Greyledge Flag Barn. Offers potential either as a renovation opportunity or as a new build given the dramatic vistas of the Shepaug River Valley afforded by the elevation and 240-degree views.

PARCEL C-1: 9.5± unencumbered acres in Roxbury; undeveloped land offers unobstructed eastern and southeastern views.

PARCEL D: 17 Berry Road, Bridgewater. 72.97± unencumbered acres comprising Greyledge Barn/Office/Residence of 8,500 square feet, separate four-vehicle garage, haylofts, and established farm animal/equestrian turnouts. Barns and Haylofts can be repurposed as a conventional garage and storage space, or additional living quarters to accommodate a car collection and/or staff. The property is surrounded by stone walls and pasture, and offers multiple new building sites.

PARCEL E: 495 Hut Hill Road, Bridgewater. 2.5± unencumbered acres comprising the Estate Manager's Residence of 2,048 square-feet; 4 bedrooms, 2 baths;

PARCEL F: Greyledge Angus Pasture comprising 31.26 unencumbered acres in Roxbury; the land offers the possibility of several large building sites, the majority with sufficient elevation to capture views north and east over the Shepaug River Valley into Roxbury.  

PARCEL G: Greyledge Preserve comprising 79.19 unencumbered acres abutting 500+ acres of Roxbury Land Trust; provides excellent venue for hiking, hunting, horseback riding, and observing wildlife. The property also offers the possibility of several elevated building sites with distant views in all directions. 

PARCEL H: The Trailhead comprising 5.34 unencumbered acres abutting 500+ acres of Roxbury Land Trust property, including the Golden Harvest, Erbacher, and Orzech Preserves, which offers direct access to several miles of trails as well as fly fishing on the Shepaug River. 

*All acreage estimated.


The Main House comprises two separate houses: "The Bridgewater House" — a C.1820 center-hall clapboard colonial that fronts the driveway, and "The Roxbury House" — a C.1789 saltbox and former tavern which was relocated from a Roxbury estate to Greyledge Farm in 1939. 

The prior owner of Greyledge — a prominent attorney with a strong affinity for architecture — retained the Boston-based architecture firm of Perry, Shaw and Hepburn (the same firm retained by John D. Rockefeller to design and build Colonial Williamsburg), to site and integrate the two homes in an architecturally consistent and complimentary manner. The result is a primary residence of 10,000± square feet and a masterpiece of architectural design. 

The integration was effected with the introduction of the lower profile center section of the house which includes a living room, additional reception rooms and staircases, a large tack room, and the construction of an English basement in the Roxbury house to provide additional staff living quarters. 

The current owners undertook a comprehensive renovation of the home, related HVAC and well infrastructure and exterior surroundings, including rebuilding 1,500 feet of stone walls in the immediate vicinity of the house. 

The Main House is now comprised of 10 bedrooms (four with fireplaces), multiple living/family rooms, breezeways lined with French doors, two outdoor terraces, a library, office, nine fireplaces, a chef's kitchen, and a dramatic candle-lit dining room that can comfortably accommodate large seated dinners for 24 people.


Fully integrated with the main house, this former tavern was dismantled from a Roxbury estate and relocated to Greyledge Farm in 1940.


The pool house, gunite pool, related hardscape and landscaping were added to the property in 1998. The area is bordered by stone walls, majestic 100-foot pine trees, and attractive rock ledges that informed the Estate's Greyledge appellation.

The Pool House is comprised of a combined living/dining room with fireplace, a full kitchen, two changing rooms, two full baths, and two large bedrooms. 

The Pool House is located approximately 100 yards from the Main House, affording both an attractive visual landmark as well as an alternative living venue for privacy or large gatherings of weekend guests.


The Estate's most elevated build site comprising 20 acres of primarily open pasture with 360-degree views


67.59 ACRES. ROXBURY. The Dickinson Dairy House (also known as the Seruphas Ward House c. 1845) is a vernacular farmhouse influenced by the Greek Revival style. It is composed of an early 19th-century center hall building and a recessed kitchen wing to the south with an full English basement at the rear. The Dairy House provides an interesting perspective how country builders at this time integrated both colonial and Greek Revival styles in Litchfield County. 

The home has not been occupied since the current owner purchased the property and it requires extensive renovation. Three generations of dairy families have lived in the house and processed milk in the barns and buildings that at one point occupied the property. 

The Dickinson Dairy House offers interesting potential either as a renovation opportunity or as a new build given the dramatic vistas of the contours of the Shepaug River Valley afforded by the home's elevated position and 240-degree views.


The Greyledge Barn was constructed in 1996 and is built of weathered siding from a barn in Indiana to replicate the look and aesthetic of a calving barn of similar size that used to occupy the rocky promontory that defines Greyledge Farm and the Estate. The barn is now used primarily for vehicle and equipment storage; however, it can be easily repurposed as it has a poured concrete floor, excellent natural light, and the structural integrity of a new building. The owners adorned the barn with a painting of the American flag in late 2001. The combination of the flag painting, the visual appeal of the barn, and its elevated position have made it a landmark in Litchfield County and contributed to its appearance in a number of local and national publications.


9.5 ACRES. ROXBURY. Undeveloped and unencumbered build site offers unobstructed eastern and southeastern views.


 72.97 ACRES. BRIDGEWATER. Greyledge Barn/Residence/Farm Office, associated buildings, and paddocks were constructed by the current owner in 2007. The Barn is sited in an elevated position on the southwest quadrant of the Estate to ensure views and access to the breeze emanating from the Shepaug River Valley while affording the Main House both distance and privacy from the Farm. The design of the building(s) borrows from the Judds Bridge Farm in Roxbury and seeks to maintain aesthetic and architectural consistency with the other buildings on the Greyledge Estate. The 8,500-square-foot Barn building utilizes the same clapboard design, 12-over-12 mullioned windows, cedar shake roof, and copper gutters found on nearly all Greyledge buildings, while integrating leading HVAC and water technology as well as solar panels to support the Farm's all natural, eco-friendly mission. 

While the buildings are currently utilized for commercial purposes, the Barn was designed to be easily converted into a substantial residence with the addition of five evenly spaced dormers on the second floor of the barn which would align with the six-foot-tall windows on the ground floor to allow for the creation of up to five en suite bedrooms. 

The Tractor Barns and Haylofts located behind Greyledge Barn can be repurposed as a conventional garage and storage space, or additional living quarters to accommodate a car collection and/or staff. Greyledge Barn (Parcel D) is comprised of 73± acres and surrounded by stone walls, pasture, and horse or cattle/sheep turn-outs designed by the owner. The property offers multiple new building sites.


The Estate Manager's Residence was extensively renovated by the current owner in 2009, including the addition of a second story to the house to make its appearance more consistent with the architecture on the remainder of the Estate. The current design of the Estate Manager's Residence was inspired by the architecture associated with The King's Arms Tavern at Colonial Williamsburg. The home is comprised of eight rooms, including four bedrooms, two baths, living room, dining room, newly updated kitchen and a full, partially finished basement. HVAC, well service, and plumbing were updated at the time of the renovation.


The combination of wooded acres and open pasture is complimented by stone walls and board fence to create what is widely considered to be the most scenic entrance to the town of Roxbury from the west. This parcel is comprised of 31.26± acres which offer a diversity of topography that is bisected by a scenic stream, new growth woods, and multiple stone walls dating to the 1800's when the entire area was in pasture or used for agriculture. The land offers the possibility of several large building sites, the majority having sufficient elevation to capture the views north and east over the Shepaug River Valley into Roxbury.


The Preserve is comprised of 76.19 undeveloped and unencumbered acres in Roxbury that abuts 560 acres of Land Trust property to the north and east. The diverse topography with close proximity to Shepaug River provides an excellent venue for hunting, horseback riding, and observing local wildlife in a variety of natural habitats. The property also offers the possibility of several elevated building sites with distant views in all directions.


This unique 5.34±-acre parcel abutting approximately 560 acres of Roxbury Land Trust property, including the Golden Harvest, Erbacher, and Orzech Preserves, which provides direct access to several miles of walking and horse trails as well as fly fishing on the Shepaug River. An ideal site for a naturalist owing to a pond, adjacent wetlands, and lightly forested habitat which support a diversity of birds and wildlife. The parcel includes the trail head for accessing the abutting Roxbury Land Trust property from the south (by oral agreement with the current owner). The property remains unencumbered.

Additional Opportunities: 

The purchaser can maximize the value of the existing land by reconfiguring select parcels and performing lot line adjustments with neighboring properties, as follows: 

PARCEL B: create new 20-acre building parcel comprised primarily of open pasture and 360-degree views on the Estate's most elevated build site 

PARCEL C-1: expand existing parcel to 20 acres 

VIEW SHEDS: offer lot line adjustment with seven Skyline Ridge landowners to afford permanent control of view along western border of Parcel D

About the Area


The quaint town of Bridgewater, situated on the east bank of the Housatonic River, is a largely residential community encompassing 17.3 square miles. An old farming community incorporated in 1856, Bridgewater is home to barns, paddocks and country estates as well as beautiful Lake Lillinonah. The charming town green is a haven for many passersby who stop at the historic general store for some famous Bridgewater Chocolates or to enjoy fine New England fare. Until 2014, Bridgewater was known as the last remaining dry town in the state. A highly anticipated event in Bridgewater takes place each fall, when the town hosts the annual Bridgewater Country Fair, which has drawn generations of residents and visitors to this otherwise quiet community.


The unspoiled and scenic town of Roxbury, located in beautiful Litchfield County, was incorporated in 1796. Roxbury was long known as a mining town, as silver was mined here as well as iron for steel making and granite used to construct, among other landmarks, the Brooklyn Bridge and Grand Central Station. Roxbury is also known as a picturesque farming town with its beautiful rolling hills and open fields, and its location within the watershed of the Shepaug River. The area is as diverse as its residents, which include actors, artists, writers and local tradesmen who help to keep the ambulance and fire department a volunteer service. Nearly 3,000 acres, or about 15 percent, of Roxbury's total area is conserved as open space under the stewardship of the Roxbury Land Trust. The Trust was established in 1970 and continues its mission to protect the natural beauty and rural character of the town, providing space for hiking, fishing, cross country skiing and biking.

For Sale by

William Pitt Sotheby's International Realty

6 Green Hill Road
United States
Member since 2015 Trusted seller
Mark Madonna
Responsible agent
Mark Madonna