The 1989 post-and-beam house at 139 Charlie Hill Rd in Millerton went under contract 4 days after the current listing date and closed $5,000 above its final asking price of $1,795,000. It stood at the head of the five highest-priced home sales publicly reported in the Poughkeepsie, New York metro area for the week ending September 27, 2026, a group that combined for $7.01 million.
The week’s sales were spread across Millerton, Wingdale, Rhinebeck, Goshen and Hyde Park, and they span build years from 1860 to 2014. Ponds, pools and mountain or Hudson River views run through the week’s records, which range from a two-bedroom house designed by a named architect to a restored six-bedroom Hudson Valley estate on 8.2 acres.
No. 1 — $1,800,000 · 139 Charlie Hill Rd, Millerton, New York
A post-and-beam house on 12 private acres along Charlie Hill Road in Millerton sold for $1.80 million, the highest reported price in the metro area for the week. The land takes in a rolling meadow and a pond, and the house was sited for western-facing sunset views over the Catskill Mountains. The property previously changed hands for $1,275,000 in 2002.
Built in 1989 and carrying a reported 3,817 square feet, the four-bedroom, five-bath residence is organized around a two-story living room where a wall of windows and French doors frame the mountain views. A floor-to-ceiling chimney holding a double-sided fireplace divides that room from the kitchen and dining area, and the approach up Charlie Hill Road opens onto the meadow and the water before the house comes into view.
Mimi Harson of William Pitt Sotheby’s – Salisbury was the listing agent. The transaction closed on September 25, 2026, $5,000 above its final asking price of $1,795,000, after the property went under contract 4 days after the current listing date. The transaction ranked No. 1 in RealtyWire’s Poughkeepsie Metro Area Top 5 for the week ending September 27, 2026.
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No. 2 — $1,390,000 · 165 Duell Hollow Road, Wingdale, New York
A copper-clad contemporary house designed by architect Allan Shope sold for $1,390,000 in Wingdale, where it sits on a secluded, wooded parcel of 29.7 acres. A substantial pond on the property was once part of the historic Camp Sacajawea, and the setting looks out toward the mountains and the water. It previously changed hands for $360,000 in 2010, before the current residence was completed in 2014.
Completed in 2014, the two-bedroom, one-bath residence holds a reported 1,600 square feet and was built with handcrafted black walnut woodwork imported from Thailand. Floor-to-ceiling windows with custom drapes, glass countertops, a gas fireplace and radiant heated floors run through the house, the kitchen is fitted with Thermador appliances, and an automatic generator serves the property during power outages. Listing materials identify plans available for the construction of an additional, larger home on the acreage.
Bianca D’Alesandro of Compass Greater NY LLC was the listing agent on the Wingdale sale, which took the No. 2 position in RealtyWire’s Poughkeepsie Metro Area Top 5 for the week. The transaction was dated September 25, 2026, and the property closed $90,001 above its final asking price of $1,299,999. Anne C. Rajs of Corcoran Country Living represented the buyer.
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No. 3 — $1,375,000 · 6 Stanford Court, Rhinebeck, New York
Margaret Santamorena of Houlihan Lawrence Inc. was the listing agent for the Rhinebeck house. The sale closed on September 24, 2026, $80,000 above its final asking price of $1,295,000, and the property went under contract 24 days after the current listing date. The closing placed third in RealtyWire’s weekly Poughkeepsie Metro Area Top 5, and Michael Lawlor of Howard Hanna Rand Realty represented the buyer.
A custom-built contemporary house on 1.2 professionally landscaped acres about a mile from Rhinebeck Village sold for $1,375,000. The grounds are screened by mature trees, with neighboring houses set well apart. It previously changed hands for $713,000 in 2018.
Completed in 2003, the three-bedroom residence carries a reported 4,791 square feet. Its main level pairs a kitchen with granite countertops and a bar sink with an adjoining gathering room, and a living room anchored by a fireplace flows into a dining room with a wall of windows facing the property. A first-floor primary suite with a private bath, a powder room and a mudroom complete that floor, while two larger bedrooms, a full bath and a reading nook sit upstairs. The lower level holds a home office, a full bath, a recreation area, a gym and a laundry room.
Outside, a bluestone patio, a saltwater pool, a pool house and an outdoor shower sit beside an expansive lawn. Starr Park, the elementary school and the Amtrak station are close by, and the village’s shops, restaurants and cafes are a short distance from the house.
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No. 4 — $1,244,400 · 395 Sarah Wells Trail, Goshen, New York
Twin Oaks, an 1860 French Second Empire Late Victorian house on a park-like 8.2-acre parcel at the edge of the Village of Goshen, sold for $1,244,400. The estate sits along one of the Hudson Valley’s scenic country roads, a short walk from the village’s shops, dining, parks and public library.
The six-bedroom residence carries a reported 5,450 square feet and has been extensively renovated while its original character and architectural integrity were preserved. Recent work covers new composite siding, cornices, soffits and window trim, slate-style mansard and flat roofing, 25 Andersen windows and five custom exterior doors, a rebuilt and refinished front porch with upgraded floors, ceilings and beams, Mitsubishi mini-split systems in most rooms, dual-zone boiler systems for baseboard heating, and a fully reimagined primary suite with views over the grounds.
The saltwater pool, its surrounding stonework and the walkways were rebuilt as part of that program, and the grounds also hold a private tennis and basketball court, a fountain, a front porch and a rear stone patio for outdoor dining. A whole-house security system with fire and smoke detection, a front door camera, an electric vehicle charging station near the front porch and a water purification and softening system serve the house. Route 17, Interstate 87 and Interstate 84 are within reach, and New York City is a little over an hour away by car, bus or train.
The transaction was completed September 25, 2026. The property previously changed hands for $875,000 in 2018.
Joseph Paoli of Howard Hanna Rand Realty was the listing agent for the restored estate in Goshen, and the sale ranked fourth among the metro-area transactions in RealtyWire’s Top 5 for the week. Alexander DeLaCruz of Howard Hanna Rand Realty represented the buyer.
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No. 5 — $1,200,000 · 18 Scenic Drive, Hyde Park, New York
An architect-owned mid-century house above the Hudson River on Scenic Drive in Hyde Park sold for $1,200,000. Scenic Drive is an enclave of mid-century houses terraced to take in the river views, tucked between Route 9 and the Hudson about eight miles south of Rhinebeck village and two miles from Hyde Park village. It previously changed hands for $320,000 in 2016.
Built in 1970 and fully renovated, the house carries a reported 3,310 square feet across three levels, with four bedrooms, four baths and two wood-burning fireplaces. A 1970s fireplace anchors the open-plan living and dining level reached through double doors and a double-height foyer, French doors lead out to a wisteria-covered pergola and a front terrace set for dining with the river as a backdrop, and the renovated kitchen combines a large center island, an induction range and Bosch appliances.
A staircase in the foyer rises to seating areas facing north toward the pool and south toward the Hudson. A gallery hall leads past two guest bedrooms, an office lined with oversized windows and an updated full bath with a double vanity to the primary suite, which occupies a private corner with a wall of windows framing the river, two closets and a bath with a glass shower and a clawfoot soaking tub. The walk-out lower level adds a second wood-burning fireplace, a full bath and radiant heated floors, and is currently configured as a media room and gym with separate entrances on both sides of the house.
The grounds run to nearly five landscaped acres, centered on a swimming pool with a red brick surround and including a fire pit, an expansive patio, a level lawn and a path through private woods to a pond below. The house sits between the Metro-North Railroad and Amtrak stations, under two hours from New York City. The Hyde Park transaction was finalized September 25, 2026.
Brett Snider of Rouse + Co Real Estate, LLC was the listing agent. The property closed at its full asking price and went under contract 6 days after the current listing date. The full-price result put him at the listing side of the fifth-ranked sale in RealtyWire’s Poughkeepsie Metro Area Top 5 for the week.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, September 27, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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