Luxury Greenwood VA Homes for Sale

Recently Sold Luxury Greenwood VA Real Estate

As of 2024, the median price of Greenwood VA real estate is $755,000.

Greenwood Virginia is one of the most attractive areas of Central Virginia and is renowned for its exquisite mid-19th-century plantations.

Greenwood is 20 minutes from UVA and all are homes for sale near Crozet VA.

Blue Ridge Farm, Greenwood VA

Four of the most exquisite Greenwood homes can be viewed from the road. They are Blue Ridge Farm, Mirador, Ramsay, and Tiverton.

Tiverton circa 1912 – Rufus Holsinger

Lady Astor (the first woman in the House of Commons and once an American) lived at Mirador. Her sister, Irene Gibson (of The Gibson Girl Fame – America’s top model from the 1890s until World War I), lived next door at Ramsay with her talented husband Charles Dana Gibson. Tiverton, is an exact replica of the White House and is currently owned by music czar, Coran Capshaw.

Be sure to visit Emmanuel Episcopal Church. It’s a historic Virginia gem and was built in the 1850s to serve the owners of Mirador.

Once a railroad destination for those fleeing the big cities to hike, fish, and pick apples and peaches; today it is one of the top vineyard destinations.

Greenwood is located due west of Crozet off Rt 250 and shares an off-on I-64 exit. The little hamlet is home to a post office and a fun antique store. Mins from the hamlet, along Rt 250 is the extraordinary Greenwood Grocery where they offer the best of the best in gourmet foods.

There are never many homes for sale in Greenwood as it’s mainly large farms and estates. From Jan 2022 11 homes in Greenwood were sold.

What I like about living in Greenwood, Virginia…

The history and architecture are fabulous. Vineyards abound and Wintergreen Ski Resort is minutes Southwest.

The University of Virginia is 20 minutes away. Downtown Charlottesville is 25 minutes and it’s a straight shot on Rt 250.

The Western Albemarle Schools are minutes from Greenwood.

I love picking strawberries and peaches at Chiles Orchards and attending Sunday polo matches at King Family Vineyards. The newest vineyard in the area is Septenary which is part of the fabulous Seven Oaks Farm (also visible on Rt 250).


My favorite places to eat in Greenwood are Chiswell Farm & Winery and the scrumptious Greenwood Grocery on Rt 250 East.

My favorite historic church is the magnificent Emmanuel Episcopal Church built in 1860.


Greenwood VA History

The Greenwood area was among the first permanently settled areas in Albemarle County. Most of the settlers in this area arrived from the west and included both Scotch Irish Presbyterians and Germans. One of the first European Americans into this area of Albemarle County was Michael Woods.

He crossed over from the Shenandoah Valley in the 1730s through a gap originally known as Woods Gap and now known as Jarman’s Gap. His home place was at Mountain Plains.

His son-in-law, William Wallace, was among the first to patent land in the Greenwood area. Piedmont Farm, located west of Route 690 and south of I-64, is part of an original William Wallace patent of 1738.

Another early patent in Greenwood was for 400 acres issued to Davis Stockton in 1774. This is now the site of Seven Oaks farm. Stockton gave his name to Stockton Creek, which flows through this area.

Most of the early settlers were farmers who grew tobacco, although wheat and other cereal grains became the dominant crop by the 1780s. Farms were generally smaller in size than in eastern or southern Albemarle County.

Although the Anglican faith was the official religion in colonial Virginia, the Greenwood area contained a large concentration of Presbyterians.

In 1747, a group of Presbyterians in western Albemarle County issued a call to the Hanover Presbytery for a minister, the Rev. Samuel Black. Black purchased the original Stockton property and founded the Mountain Plains Presbyterian Church in June 1747.

Lebanon Church

Lebanon Church, west of Greenwood and built in the 1840s, is the successor to this church. Black also may be responsible for the construction of Black’s Tavern, a log building currently on the grounds of Seven Oaks Farm. Seven Oak has a vineyard called Septanary and is open to the public.

Although its construction date is unclear, the explorer, George Rogers Clark, noted staying here in 1770.

Black’s Tavern was in operation by the Black family until the 1820s. Several other buildings in the Greenwood vicinity date from the eighteenth century.

The original part of William Wallace’s Piedmont may also date from the 1760-1780 period. Isaac Hardin settled a plantation in this area in 1785, which is named Greenwood. He lived there until his death in 1820.

Early National Period

Transportation routes through this area provided an important stimulus to population growth. Several stores and taverns were built to serve passengers along the busy Staunton and James River turnpike, as well as the Rivanna & Rockfish Gap turnpike, and the Three Notch’d Road.

In addition to Black’s Tavern, they included the Brookeville Tavern, located slightly west of Greenwood, and Yancey’s (May’s) Tavern. Yancey’s Tavern and a two-story gristmill were built around 1817 by Colonel Charles Yancey, who later sold them to Elijah May.

The tavern and mill were located on the south side of the present day U.S. 250, west of its intersection with I-64. The building now known as Long House may have been a part of this tavern complex.

Long House

Col. John S. Cocke settled in the Greenwood area as early as 11824. Three years later Cocke bought Elijah May’s tavern. Coke moved into the house now known as the Cedars across the street road in 1840. Cocke’s Tavern, (now the Long House across the street from The Cedars), was especially popular with travelers on their way to the Virginia mineral spring resorts.

The Cedars

Antebellum Period (1830-1860)

The Bowen’s were a major land holding family in the Greenwood area during the antebellum period.


In the 1835, James M. Bowen, a farmer and merchant originally from Rappahannock County, bought the Ramsay property.

It included a mill that had been built by William Ramsay in the late 1700s. Bowen named the small brick house he built on his property Mirador.


His brother, Thomas Bowen, a schoolteacher, arrived in Albemarle County in 1837. He bought three tracts in the Greenwood vicinity: Huntsmans, Hard Labor and the old Isaac Hardin farm, Greenwood. He lived most of his life at Greenwood. Thomas Bowen also built the house known as Fairview, which was inherited by his daughter, Julia Bowen Shirley. Fairview burned, and the land was sold to settle Bowen’s debts. Another Bowen brother, Peter, never lived in Albemarle County but he did buy land in the Greenwood area.

The arrival of the railroad in Greenwood in 1850 marked an important new chapter in the area’s history. In 1850, the Blue Ridge Railroad Company started construction on four tunnels and several cuts through the Blue Ridge Mountains.

Under the direction of French engineer Claudius Crozet, the first of the four tunnels, the 538-foot-long Greenwood Tunnel, was completed in 1853.

Thomas Bowen sold a right-of-way to the railroad, and the railway depot located on the east side of the railroad tracks took its name from Bowen’s farm at Greenwood. In 1853 a post office was established and officially named Greenwood Depot. The 547 miles of temporary track laid to enable trains to cross the Blue Ridge while the tunnel work was in progress in 1854.

In 1856, the Rev. William Dinwiddie, a graduate and former faculty member of the University of Virginia, founded Brookland School near Greenwood on the property of John Cocke. A year later, h moved this boy’s school to his own property at Greenwood Depot. Part of the school property is the house presently known as Old Paradise.

Locust Valley Academy was another secondary academy operating in Greenwood. Former University faculty member, Gessner Harrison, organized it in 1860. After the Civil War, a Mr. Yancey and Mr. Wood also taught a school for boys in the same building that Harrison had used for his school.

Civil War (1861-1865)

Although there were no military engagements in the Greenwood area during the Civil War, several buildings around Greenwood were used as troop hospitals by the Confederate forces. The Cedars is said to have been a hospital operated by Dr. Hunter McGuire, and received wounded soldiers brought there from Greenwood Depot.

In August 1862, the Rev. Dinwiddie wrote to Confederate authorities objecting to an order that he allow his school property and home to be used as a Confederate hospital. His objections were based on the fact that he already had provided shelter for the sick and wounded, as indicated in the following excerpt from his appeal:

“We have done much as a family to aid the cause of our country. I cheerfully gave up 22 rooms which I had used for school; purposes for the use of the hospital which was established here in June and afterwards removed to Nelson Co. These 22 rooms with tents in addition proved sufficient for the accommodation of as many as 800 patients. I crowded up pupils and family all into 2 buildings to make room for the sick…”

On March 2, 1865, George A. Custer led a vanguard from General Philip Sheridan’s force of 5,000 Union soldiers towards Charlottesville from the Shenandoah Valley. Along the way he destroyed much Government property and subsistence at Greenwood Depot.

Custer sent a telegram to Sheridan late in the day on March 2 reporting: “I have just captured Greenwood Depot with 75 prisoners and 3 guns together with an immense quantity of government stores and cotton. Have destroyed all of these together with 500 saddles complete.” Custer went on to destroy the bridge over Mechum’s River and stores at Ivy station before arriving in Charlottesville on March 3.

The Rev. Dinwiddie continued as an active member of the Greenwood community. After the Civil War he served five years as pastor of Lebanon Presbyterian Church. Having served in churches in Lexington, Kentucky and Alexandria, Virginia, Dinwiddie returned to Greenwood in 1888, where he died in 1894.

In the late nineteenth and early twentieth centuries, the larger neighborhood around Greenwood attracted several very wealthy residents who moved there from elsewhere in Virginia as well as northern states.

These newcomers either remodeled existing estate homes or built large and elegant new ones.

Tobacco and railroad magnate Chiswell Dabney Langhorne purchased Mirador in 1893 as a summer home.

In 1902, Langhorne sold his Richmond home and Mirador became the family’s full-time residence. He and his family did much to popularize the Greenwood estate area during the turn of the century. In 1910, Langhorne gave Mirador to one of his daughters and moved to a smaller property, which he bought across the road. He named it Misfit.

Several other estates in the area, including Seven Oaks, Ramsay and Wavetree Hall are associated with the Langhorne family.

Seven Oaks

Two of Langhorne’s five daughters achieved lasting fame. Irene Langhorne married artist

Irene Gibson

Charles Dana Gibson and became the model for his Gibson girl drawings, which defined the era’s ideal for feminine beauty. Nancy married the son of the British nobleman Lord Astor and moved to England. When her father-in-law died, her husband assumed his seat in the House of Lords and gave up his seat in the House of Commons.

Nancy Astor

Nancy, Lady Astor campaigned for his former position and won the election. She was, thereafter, elected to several more terms, and was the first woman elected to that house.

In the summer of 1904, Mrs. William Massie, daughter of T.C. Williams of Richmond built the first house at Rose Hill. At the time, she had not yet married William R. Massie. This large rambling frame house, with its expansive views of the Blue Ridge Mountains, was a focal point for the social life of the Greenwood area.

Rose Hill

Massie’s daughter, Ella Williams Smith, published her memoirs revealing much about life in the Greenwood neighborhood in the early decades of this century. Speaking of the years 1904 to 1910, Mrs. Smith reported that roads were terrible and a trip to Charlottesville might take four hours, so visits to the county seat were infrequent and were made by train.

Black workers on the states lived in Newtown, a black settlement on Greenwood Mountain. Greenwood Depot was the center of commercial activity in the area, with the post office and Mr. Bruce’s store, in addition to the railway depot. The former Dinwiddie School was used a s a tourist home during this period, to which boarders came in droves all summer.

In describing the three-mile route from Rose Hill to Greenwood Depot, Smith noted arriving at a quiet crossroads where Mr. Woodson’s home and blacksmith shop were located. At this point there was a sharp left turn to climb the mountain to the depot.

The crossroads she described is most likely the point where Routes 690 and 691 intersect today. This hamlet is known as Greenwood Country Store today. In the 1880s, the first building for the Country Store was constructed and it served as the community’s general store for many years. Some buildings in Greenwood Country Store date from the early 1900s.

Most residents of the Greenwood area worked on the surrounding large estates and farms.

In 1889, the first free public school for the community was organized by area residents, at first using a log building on a local estate. The school moved to a better building on Stony Run near Beagle’s Gap Road the next year.

In 1903, the school moved to a one-story building on the north side of Route 691 at Greenwood Country Store. Five years later a two-story frame building was constructed next to it, which housed the Greenwood School until just after World War I.

Greenwood grew as a small but active center of a rich agricultural area. Greenwood Depot had an estimated population of sixty. In 1913, the post office changed its name to Greenwood. During these years the burgeoning fruit industry was the economic mainstay of the community, as it was for all of western Albemarle County, supplying employment for local residents.

World War I to World War II (1914-1945)

Greenwood continued as a popular area of estates, fox hunts, and social activity. Casa Maria, an unusual Spanish-style residence, was built 1927-1928. Blue Ridge Farm was remodeled in the classical style during the late 1920s. Washington DC architect, Waddy Wood, greatly enlarged Emmanuel Episcopal Church with money from the Langhorne and Astor families.

The Massie home at Rose Hill burned in 1930 and was replaced by the neo-Palladian masterpiece by New York architect William Bottomley.

The prominent Tree family also remodeled Mirador.

Greenwood School became an accredited high school in 1919, one of only six accredited high schools in the county. It drew students from Midway, Edgewood, Hillsboro and Batesville grade schools as well as the Greenwood community. With increasing enrollments, a drive was launched to raise funds for a new school, and with generous donations from community members, the new building was ready for its first graduating class in 1922. The older two-story frame building was removed, but the first school building remained on the site. For many years it housed primary grades. It was called “Little Greenwood,” and stood until the 1960s. The grounds around the school were graded in the early 1930s and in 1938 an addition was built to house two more classrooms and a gymnasium. With the opening of the consolidated Albemarle High School in 1953, Greenwood became an elementary school. It closed its doors for good in June 1984, when its students were transferred to Brownsville and Red Hill Elementary Schools.

Modern Period (1945-Present)

In 1949, the Greenwood Community Center was built with donations from local residents (and former residents like Lady Astor) as a memorial to local men who served in both world wars. It has served as a recreational and social center for the community ever since. For many years it operated on money raised from local activities organized by the community, but the county took over operations in 1982.

Rail passenger traffic ceased at Greenwood in the 1940s. The center of the community gradually shifted to the Greenwood Country Store community after 1945.

In 1955, the Country Store was gutted by fire. It was rebuilt soon after; the present building served for many years as the commercial focus of this community. It was called Young Brothers Country Store for a time after it reopened.

In 1960, a new post office was built at Greenwood Country Store. Built by Stanislaus Makielski, it replaced the post office established at the rail stop more than a century ago.

And that’s all the news from Greenwood, Virginia in 2024.