The house's west facade is the longest and most ornate, and has a view of the Hudson River from its west-facing windows and adjoining terrace.

The interior also has significant features, including marble fireplaces, coffered ceilings, and extensive carved wood and plaster detail.

[3] Facilities include the main clubhouse, a pool complex, ten Har-Tru tennis courts, four aluminum heated platform tennis courts, four squash courts, eighteen guest rooms, skeet and trap areas, a 45-horse boarding facility, twenty paddocks, a large indoor riding arena, pro shops for golf and paddle sports, a fitness complex,[4] the golf course and practice range (non-contributing), outdoor riding rings, stables, and a carriage house.

[4] The club property surrounds Saint Mary's Episcopal Church on three sides and slopes upwards east from U.S. Route 9.

In November 1896, Maria Louisa Kissam (Margaret's mother and widow of William Henry Vanderbilt) died in the house.

[19] The house and property's worth at the time was estimated between $4 and 6 million, and it was often said that its owners didn't know how much money had been spent constructing and improving the estate.

[13]: 160 The two men assembled a board of directors to form a country club, including future Titanic victim John Jacob Astor IV, coal baron Edward Julius Berwind, cotillion leaders Elisha Dyer and Lispenard Stewart, and sportsmen W. Averell Harriman, Cornelius Vanderbilt III, and Harrison A.

The club then constructed the golf course in close harmony to the existing lawns, and also built an outdoor garden theater with clipped cedars and a 16th-century Italian portal.

Cuts were made – horses were sold, Woodlea was closed except for special occasions, and the golf house became the primary clubhouse.

In 1961, in time for the club's 50th anniversary, Woodlea was redecorated with more modern fabrics, warm gold and forest green carpets, dropped lighting, and some lowered ceilings.

[13]: 169  In the garden's location and replacing the use of the golf house, a wing was added to the clubhouse, constructed on the northeast terrace and completed in 1962.

The structure was designed to be spacious and convenient and not be noticeable from the grounds below, although from Woodlea, the sight of the tar roof and ventilators was noted to be worse than the prior standing gardens.

[13]: 162  Woodlea incorporates characteristics of the Beaux-Arts style of architecture – the exterior dictates the use of the interior, with family and guest rooms on the third floor.

[6] The curtain wall between the facade's pavilions contains a semicircular portico, and its entablature is upheld by Ionic columns, and supports a balustrade.

[5] The original furnishings together were reported in 1895 to have cost hundreds of thousands of dollars, and to have included rare tapestries, carved woods, paintings, and Italian marble.

The house's main door opens into a square vaulted vestibule, walled throughout with highly polished yellow marble.

It leads into the main hall, which is paneled to the ceiling in wood, painted white, the corners and angles accentuated by pilasters, and the rich mahogany doors encased within monumental frames.

The rooms are all over-scaled in terms of the height of the ceilings and size of the doors, with large fireplaces, and the length and breadth of the stairway to the house's second floor.

[29] The stable was designed by McKim, Mead & White and built in the late 19th century using the same yellow brick used for the main residence.

The pedimented central bay has an arched recessed entrance with a pair of oversized double wood doors beneath a fanlight.

The arch impost line continues as a belt course between the pavilions and forms the sills for recessed wood-framed, fixed-sashed, nine-light windows on the building's second level.

[5] The two-story interior space on the first floor was originally used for carriages and then for automobiles, and now is used as an indoor exercising ring for the horses occupying the stalls below.

In the end pavilions, there is a reception area, tack room, and small apartment designed to be occupied by the riding instructor.

The lower-level windows have flat-arched surrounds with keystones; the oculi break the cornice lines beneath segmentally arched pediments.

[37]: 11  Mrs. Thomas F. Logan, an Ardsley resident and member of the Sleepy Hollow Riding Committee, funded the building's $300,000 expense ($4.56 million in 2023[2]) and supervised its construction.

In the northwest corner of the intersection between the building's two sections is a one-story-high, one-bay-square addition with a narrow metal casement window on the west facade and a large double entrance for horses on the north.

To the west of the building's site, standing alone in the tall grass, is a 16th-century post-and-lintel stone element, which was at the center of the stage of a 1,500-seat outdoor Greek amphitheater that was part of the Shepard estate and was since dismantled.

[5] The carriage barn complex predates the Shepards' ownership of the property; it was built around 1875 as part of Wright's original estate.

There is a small building in the northeast corner of the complex; it is one bay square with a steep hip roof with spring eaves.

The building has a counterpart across the yard, with a low hip roof, a large brick chimney, and a stone water table and string course; it has overhead doors on the north facade.