A fully renovated country house on nearly 20 acres just outside the Village of Millbrook sold for $2.73 million, the highest-priced home sale publicly reported in the Poughkeepsie, New York metro area for the week ending August 16, 2026.
The week’s five highest-priced closings combined for $7.81 million. They span Millbrook, Todd Hill Crossing, Rhinebeck, Warwick and Four Corners, and their build years run from 1960 to 2006. Renovation work runs through the record, from a Millbrook house rebuilt inside and out to a Rhinebeck ranch taken down to the studs.
No. 1 — $2,725,000 · 97 Valley Farm Road, Millbrook, New York
The house at 97 Valley Farm Road stands on nearly 20 acres just outside the Village of Millbrook, with sweeping Catskill Mountain views. It changed hands on August 11, 2026 for $2,725,000, the highest reported price in the metro area for the week. Built in 1965 and carrying a reported 4,134 square feet, the three-bedroom, five-bath house was rebuilt inside and out and was marketed as new and not previously lived in.
Windows, doors, the heating and cooling system, plumbing and electrical are all new, and white oak floors run through the interior. The kitchen was fitted with Wolf and Sub-Zero appliances, quartzite counters and backsplashes and a hidden walk-in pantry. Beamed ceilings, stone fireplaces, walls of glass and skylights carry the main rooms, and the primary suite has two separate bathrooms.
Outside, bluestone walkways and patios link a large in-ground pool, a play area with a zipline, a handmade stone fire pit, a pond with a fountain, a hardtop gazebo and a large barn. The property previously changed hands for $975,000 in 2023.
Susan Whalen of George T Whalen Real Estate was the listing agent. The $2,725,000 closing put Whalen at the listing side of RealtyWire’s highest-priced reported Poughkeepsie-area home sale of the week, No. 1 in the metro area’s Top 5 for the week ending August 16, 2026. Andrew Gates of Houlihan Lawrence Inc. represented the buyer.
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No. 2 — $2,000,000 · 55 Townsend Farm Road, Lagrangeville, New York
A Farmhouse Colonial at 55 Townsend Farm Road, in the Todd Hill Crossing area of Lagrangeville, sold for $2,000,000, the second-highest reported price in the metro area for the week. The sale closed August 10, 2026. Built in 2001 on almost 10 acres, the main house carries a reported 6,985 square feet behind a rocking-chair front porch.
A two-story foyer opens to nine-foot ceilings, custom yellow pine wide-plank floors and formal living and dining rooms. The updated kitchen has a Viking range, 42-inch white shaker cabinets and quartz counters, and it opens to a two-story great room built around a floor-to-ceiling stone fireplace and a cedar-lined sun room. A gym, a movie room and a billiards room fill the walk-out lower level.
The grounds hold a gunite in-ground pool, an outdoor kitchen and bar, a pool house with its own bath and kitchen, and a full-size basketball court. Attached and detached garages give the property five bays in all. The house stands just off the Taconic Parkway, a little over 70 miles from New York City, and it previously changed hands for $1,925,000 in 2023.
Justin M. LaFalce of KW MidHudson was the listing agent. LaFalce also represented the buyer, holding both sides of a transaction that ranked No. 2 in RealtyWire’s Poughkeepsie Metro Area Top 5 for the week ending August 16, 2026.
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No. 3 — $1,100,000 · 44 Lorraine Drive, Rhinebeck, New York
A village ranch at 44 Lorraine Drive, at the end of a dead-end road minutes from the center of Rhinebeck, closed on August 10, 2026 at $1,100,000. Built in 1960 with a reported 1,732 square feet, the three-bedroom, two-bath house was taken down to the studs and rebuilt, with new siding, roof, windows, systems, flooring and layout.
Vaulted ceilings, hardwood floors and a brick fireplace anchor the open main level, and the kitchen has custom cabinetry, a Bertazzoni range, stainless steel appliances and a wine refrigerator. The dining area opens to a fenced backyard with a stone patio, a pergola and a gas line set for a future outdoor kitchen. The primary suite occupies its own wing, with windows on three sides and a bath with a radiant heated walk-in shower, and the attached garage holds four cars. The property previously changed hands for $225,000 in 2012.
Craig Smith of Compass Greater NY, LLC was the listing agent. The house went under contract 20 days after the current listing date and closed $100,001 above its final asking price of $999,999, a result that ranked No. 3 in RealtyWire’s Poughkeepsie Metro Area Top 5 for the week.
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No. 4 — $993,000 · 14 Windmill Lane, Warwick, New York
A Center Hall Colonial at 14 Windmill Lane, in the Deer Crossing community of Warwick, closed on August 14, 2026 for $993,000. The 1994 house carries a reported 3,908 square feet, with five bedrooms and four baths on landscaped grounds.
A dual-sided wood-burning fireplace is shared between the formal living room and a family room with cathedral ceilings, skylights and French doors to the backyard. The updated kitchen has granite counters, a large center island, a six-burner gas cooktop, double wall ovens and nine-foot ceilings, and the primary suite bath has an oversized walk-in shower and a jetted soaking tub. A gunite in-ground pool with a waterfall, a cool-deck surround and a gazebo fill the backyard. The property previously changed hands for $670,000 in 2013.
Kristine Many of Keller Williams Realty was the listing agent. Many’s listing went under contract 15 days after the current listing date, and the closing placed her at No. 4 in RealtyWire’s Poughkeepsie Metro Area Top 5 for the week. Diana Marie Ryan-Assatly of Curasi Realty, Inc. represented the buyer.
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No. 5 — $990,000 · 226 Buttonwood Way, Hopewell Junction, New York
A house in the Four Corners community at 226 Buttonwood Way, Hopewell Junction, sold for $990,000 in an August 11, 2026 closing, the fifth-highest reported price in the metro area for the week. Built in 2006, it carries a reported 4,995 square feet, with four bedrooms and four baths and a layout flexible enough to live as a five-bedroom house.
Listing materials describe it as one of the largest homes on the market in Four Corners. The kitchen was built out with custom touches, and the flooring and finishes were upgraded through the house. The basement was completed as an expansive second gathering level, and a rear patio opens to a wide, level yard. It previously changed hands for $758,556 in 2006.
Alexandr Mashkin of Keller Williams Realty Partner was the listing agent. The $990,000 closing took the No. 5 place in RealtyWire’s Poughkeepsie Metro Area Top 5 for the week ending August 16, 2026. Anita S. Cristiano of HomeSmart Homes & Estates represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, August 16, 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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