The five highest-priced home sales reported in Mid-Hudson Valley, New York for the week ending October 25, 2026, came to a combined $8.355 million. Two of the homes are in Clinton Corners in Dutchess County, two are in Ulster County, in Woodstock and Olive, and one is in Middletown in Orange County.
The group covers nearly two centuries of building, from an 1836 farmhouse to a Colonial completed in 2014, with two modern homes from the 1960s between them. Several sit on acreage that runs to woods, hills or protected land.
No. 1 — $3,450,000 · 306 Meads Mountain Road, Woodstock, New York
Swoop House, at 306 Meads Mountain Road in Woodstock, sold for $3,450,000. FT Architecture & Interiors designed the home, taking its cue from the Slow House by Diller Scofidio, and its form is built around two curved walls that do not run parallel, set under sloping ceilings. Completed in 2008, it is the largest home of the five at 5,272 square feet, with four bedrooms, four bathrooms and three stories.
The setting matches the architecture. A long driveway leads in to 16.13 wooded acres with rock outcroppings, native plantings and views of the mountains, and the land borders thousands of acres of New York State land. The village of Woodstock is about five minutes away.
Inside, a two-story entry opens to the first of two great rooms. Its northern wall curves for 40 feet, with a row of ten large picture windows above, and a wood-burning fireplace sits on a hearth of Italian marble. Floors are Brazilian cumaru wood. The second great room, with 18-foot ceilings, oak floors with radiant heat and track lighting, was designed as a professional art studio and is in use as a painting studio, beside a media room lined with built-in bookcases.
Off the kitchen is a two-story screened porch with a sleeping loft reached from the primary suite, and a 40-foot deck of black locust. Bluestone patios and perennial gardens surround a hot tub, and a south-facing balcony sits at the top of the open staircase. The guest suite, studio and media room also have their own entrance and driveway at ground level.
Kimberly Cantine of Halter Associates Realty was the listing agent, and Melissa Mayes of Serhant LLC represented the buyer in the top sale of the week.
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No. 2 — $1,275,000 · 68-78 Ridge Road, Clinton Corners, New York
The home at 68-78 Ridge Road in Clinton Corners went under contract the same day it was listed and sold for $1,275,000, its full asking price. Built in 1968 of brick, it is a one-level mid-century modern ranch on a hilltop, with views to the south across rolling hills.
Its most unusual feature is an attached indoor pool of about 2,152 square feet. The kidney-shaped saltwater pool is heated, and it sits under industrial beams and a hardwood ceiling, with floor-to-ceiling bay windows facing the view. A yoga deck faces the same way outside.
The main level has 3,670 square feet, with three bedrooms and three bathrooms in all. Bedrooms are on one side and the living spaces on the other, including a living room, a sunny room suited to an office, and an island kitchen with its original Quaker Maid maple cabinets. A finished basement adds a second kitchen area and laundry. The 4.23 acres are divided into two parcels: an upper parcel of 2.23 acres with the home and a lower parcel of two acres. A fenced vegetable garden sits near the kitchen, and the Taconic State Parkway is less than a mile away.
Gregory M. Martin of K. Fortuna Realty, Inc. was on both sides of the sale, listing the home with Emmanuelle Linard of K. Fortuna Realty, Inc. and representing the buyer.
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No. 3 — $1,260,000 · 2 White Horse Road, Middletown, New York
At 2 White Horse Road in Middletown, the newest home of the five sold for $1,260,000, above its asking price. The Colonial was built in 2014 on 12.70 acres, and the property last sold for $70,000 in 2013, before the current house was built.
The home has 4,225 square feet on two stories, with three bedrooms, two full baths and a half bath. The kitchen is the center of the first floor, with granite counters, double wall ovens, a large island with a cooktop and a walk-in pantry, and it opens to a formal dining room. A three-season porch sits at the front, and the back deck has a sauna that seats six. Upstairs, the primary suite includes two walk-in closets, an office, a recreation room and a bathroom renovated in 2025 with a steam shower and soaking tub.
The home is heated and cooled by a geothermal system and has owned solar panels. Outdoors there is a heated saltwater pool, a covered pergola over a large patio, a fire pit, a full outdoor kitchen and a brick pizza oven. The three-car garage is heated and air-conditioned, and the fenced backyard includes a garden and a chicken coop.
Vanessa R. Wight of BHG Real Estate Green Team was the listing agent, and Nicholas Carbone of HomeSmart Homes & Estates represented the buyer.
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No. 4 — $1,195,000 · 191 Ridge Road, Olive, New York
A private blacktop driveway leads to 191 Ridge Road in Olive, a mid-century modern home from 1966 that sold for $1,195,000. Clerestory windows, nine-foot beamed ceilings and walls of floor-to-ceiling glass shape the single-level home, and its original tiled fireplace is still in place.
With 2,100 square feet, two bedrooms and three bathrooms, it is the smallest home of the five, on the smallest lot, 1.70 acres. It has been updated around its original materials. The kitchen now has custom cabinetry, quartz counters and zellige tile, and floors throughout are walnut and concrete over radiant heat. French doors lead from the primary bedroom to a private deck with an inset hot tub.
A heated in-ground pool was added within private fenced grounds, and bluestone patios extend the living space outside. The property borders 33 acres of DEP land, and Woodstock is about 13 minutes away. It last sold for $710,000 in 2020.
Leslie Foti of Coldwell Banker Village Green was the listing agent, and Laurie Ylvisaker, also of Coldwell Banker Village Green, represented the buyer.
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No. 5 — $1,175,000 · 36 Market Lane, Clinton Corners, New York
The oldest home in this group dates to 1836. The Greek Revival center-hall farmhouse at 36 Market Lane in Clinton Corners sold for $1,175,000, on 4.30 acres where Willow Brook winds through the property. Town historical records cited in the listing say the home was used in the Underground Railroad and as a quarterly meeting place for Quakers, while it was also a working dairy farm.
The home has 3,090 square feet, four bedrooms, four full baths and a half bath, and five fireplaces. Wide board floors, exposed beams and detailed molding run through the rooms. A double parlor with original pocket doors has two of the fireplaces, an open living and dining room has two more, and the kitchen has a wood-burning fireplace, a gas stove and an island, with a screened porch just outside. Two separate staircases reach the attic.
Outside are clapboard siding, a metal roof, original six-over-six windows, raised garden beds and several vintage outbuildings. The basement keeps the original milk room with its bluestone floor. The property last sold for $125,000 in 2017.
Patricia Hinkein and Dxina Mannello of Patricia A. Hinkein Realty were the listing agents, and Ryan Lane of Gilcrest Properties represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 25, 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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