Cedarcliff Gatehouse

Thompson House is an historic structure located in Poughkeepsie, New York. Built c. 1880, it was listed on the National Register of Historic Places on November 26, 1982. The private residence is considered to be in "excellent" condition.

Grey Hook is a historic home located at Poughkeepsie, Dutchess County, New York. It was built in 1911 and is a 11⁄2-story, two-bay-wide concrete block Bungalow-style dwelling. It features a roof that sweeps out over the porch with concrete block columns and balustrade.It was added to the National Register of Historic Places in 1982.

The Ethal House is a historic home at Poughkeepsie, Dutchess County, New York. It was built about 1910 and is a 1+1⁄2-story, three-bay-wide frame Bungalow–style dwelling on a raised cobblestone foundation. It has a gable roof with wide dormer and a large stone chimney.It was added to the National Register of Historic Places in 1982.

Sague House is a historic home located at Poughkeepsie, Dutchess County, New York. It was built about 1910 and is a 1+1⁄2-story, three-bay-wide, bungalow-style dwelling. It sits on a raised basement and four tall stone piers support the roof.It was added to the National Register of Historic Places in 1982.

Charles Morschauser House, also known as the House on the Hill, is a historic home located at Poughkeepsie, Dutchess County, New York. It was built in 1902, and is a 2+1⁄2-story, frame dwelling with a hipped roof and a projecting, offset front gable. The façade features a one-story, flat-roofed, wraparound porch.: 5 The house belonged to a local attorney, Charles Morschauser, who commissioned local architect William J. Beardsley to design the home after he had represented him in a legal matter. Morschauser had acquired an almost 3-acre parcel that had formerly been part of an estate named Mountain View, located on an oversized city lot fronting five different streets. Due to its dignified and grand appearance perched atop a knoll, the design had gained local attention in a couple of newspapers at the time. It is a transitional style containing elements of Queen Anne and Colonial Revival architecture with a blending of materials. The first story boasts a stonework façade while the second has clapboard siding, allowing it to stand out from other houses constructed at the time.It was added to the National Register of Historic Places in 2014.

Moore House is a historic home located at Poughkeepsie, Dutchess County, New York. It was built about 1910 and is a 1+1⁄2-story, three-bay-wide bungalow-style dwelling with a sweeping, slate-covered roof with dormer. It is stucco and features a broad front porch supported by massive stone piers.It was added to the National Register of Historic Places in 1982.

Poughkeepsie Meeting House (Hooker Avenue) is a historic Quaker (Society of Friends) meeting house at 249 Hooker Avenue in Poughkeepsie, New York. It was built in 1927, and is a two-story, rectangular, Colonial Revival style brick building, with a basement. It has a gable roof and projecting entrance pavilion.It was listed on the National Register of Historic Places in 1989.

Maple Grove is a historic estate located at Poughkeepsie, Dutchess County, New York. The estate consists of eight contributing buildings: the main house, farmer's cottage (c. 1850), barn (c. 1850), carriage barn (c. 1850), garage (c. 1850), shed, and two cottages (c. 1830). Also on the property is a pair of contributing sandstone gateposts (c. 1850). The main house was built in 1850 in the Italianate style and remodeled in 1891. It is constructed of painted red brick and has a 2+1⁄2-story, three-bay, main block flanked by 2-story, three-bay-wide wings. It has a large, 2-story rear kitchen wing. It features a prominent 1-story open wood porch.It was added to the National Register of Historic Places in 2001.

Springside was the estate of Matthew Vassar in Poughkeepsie, New York, United States. It is located on Academy Street just off US 9. Detailed plans for a landscape, villa, and complex of farm buildings were drawn up by the influential Andrew Jackson Downing with assistance of Calvert Vaux prior to the former's death. The landscaping was completed and remains Downing's most intact surviving landscape, but only a few of the buildings he planned were ever built; most have since been lost to fire and structural failure. A cottage where Vassar resided was dismantled and removed in the mid-1970s. Its facade is on display in the New York State Museum. Downing's landscape, in the English landscape gardening tradition, has survived several serious efforts to redevelop the property in the last half-century due to opposition from local preservationists. It was listed on the National Register of Historic Places as Matthew Vassar Estate, and further it was declared a National Historic Landmark in 1969, but the estate was not permanently protected for almost two decades, when a lawsuit was settled with the transfer of the land to its current owners, Springside Landscape Restoration.

Freer House is a historic home located at Poughkeepsie, Dutchess County, New York. It was built about 1728 and is a 1+1⁄2-story, four-bay-wide frame farmers cottage built of coursed fieldstone. It is the oldest extant structure in the City of Poughkeepsie.It was added to the National Register of Historic Places in 1982.

Dwight–Hooker Avenue Historic District is a national historic district located at Poughkeepsie, Dutchess County, New York. It includes 17 contributing residential buildings in the most architecturally significant, turn of the 20th century neighborhood in Poughkeepsie. Most of the houses were built between 1895 and 1915 and are in a variety of popular revival styles. They are mostly 2+1⁄2 to 3+1⁄2 stories in height.It was added to the National Register of Historic Places in 1982.

Reformed Dutch Church of Poughkeepsie is a historic church at 70 Hooker Avenue in Poughkeepsie, New York. The original congregation was formed in 1716. The building was constructed in 1921 and added to the National Register of Historic Places in 2008. It was designed by Charles Collens.