The five highest-priced home sales reported in Westchester–Putnam, New York for the week ending October 25, 2026, came to a combined $24.075 million.
The oldest and the newest of the five homes were built a century apart, and their lots run from just over an acre to five acres. In two of the five sales, the same agent was on both sides.
No. 1 — $6,925,000 · 280 Highland Road, Rye, New York
The week’s top sale came on Highland Road in Rye, where a Dutch Colonial built in 1928 sold for $6,925,000. The estate is known as Overtheway, a name the listing traces back to the 1930s. The shingle-sided home stands on 2.41 private, landscaped acres, approached by a circular drive with pillared entryways.
Much of the property’s life is outdoors. A covered porch wraps around the home and looks over a saltwater pool with a spa, and there are four covered porches in all. The grounds also have a pool house and a full tennis court. For entertaining there is an outdoor kitchen with a grilling station, a fire pit, patios and gardens, and a detached three-car garage adds storage.
Inside, the home has seven bedrooms, six full baths and one half bath, six fireplaces and 7,497 square feet of living space. The renovated kitchen is built around a quartz waterfall island that seats four, with a Wolf cooktop and griddle, Wolf double wall ovens and a Sub-Zero refrigerator, plus a walk-in pantry that works as a back kitchen. A side door off one of the covered porches opens to a mudroom fitted with built-in cubbies and two work stations, next to the laundry room. Downtown Rye, with its Metro-North station, shops and restaurants, is within walking distance, and the Westchester Country Club and the Apawamis Club are minutes away. The property last sold for $3.1 million in 2013.
Donna McElwee and Scott McElwee of Houlihan Lawrence Inc. were the listing agents, and the home went under contract 22 days after it was listed. Michael P. McCooey of Compass Greater NY, LLC represented the buyer. Houlihan Lawrence Inc. also had the listing on the week’s second-highest sale, in Purchase.
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No. 2 — $5,500,000 · 2 Alyssa Lane, Purchase, New York
In Purchase, a brick Colonial estate on Alyssa Lane sold for $5,500,000. Built in 2006, it is the largest home in this week’s group, with 12,422 square feet, eight bedrooms and 11 bathrooms, eight of them full and three half. Its five acres are also the most land of the five, and the property was originally recorded as two parcels, 2 and 4 Alyssa Lane, that were later combined.
A gated entry leads to stained-glass doors and a marble foyer with a sweeping staircase. The main level has a formal dining room, a living room with a fireplace, a wet bar and a wood-paneled library with a fireplace of its own. In the kitchen, a herringbone marble backsplash and quartz counters surround an oversized island, with a dual-fuel Wolf range, a Sub-Zero refrigerator and a butler’s pantry. Sliding glass doors open to a wraparound veranda overlooking the pool, the spa and a stone waterfall.
The primary suite has its own fireplace, high molded ceilings, two walk-in closets, two full baths and a steam shower. There is also an ensuite bedroom on the first floor and a bedroom suite above the garage. The walk-out lower level is given over to recreation, with a gym, a game room, a wine and tasting room, space set aside for a golf simulator and a summer kitchen that opens to the outdoor spaces.
The grounds have a heated pool and spa, a pavilion equipped with kitchen appliances, a barbecue and a pizza oven, and a basketball court. There is also a putting green, along with a goldfish pond with a fountain and winding paths. The property last sold for $3.55 million in 2019.
Debra S. Padawer represented the buyer and, with Matthew Padawer, was the listing agent, so the same agent was on both sides of the sale. Both are with Houlihan Lawrence Inc., which also had the listing on the week’s top sale in Rye.
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No. 3 — $4,200,000 · 8-10 Championship Drive, Mamaroneck, New York
The newest home of the five backs onto the East Course at Winged Foot Golf Club in Mamaroneck, with open views across the course. The brick center-hall Colonial on Championship Drive was built in 2009 and sold for $4,200,000.
The home has six bedrooms, five full baths and three half baths across 9,706 square feet, on 1.60 acres. A double-height foyer opens to a formal living room with a fireplace, which leads into a first-floor office with windows on three sides. The chef’s kitchen, with a breakfast area and a butler’s pantry, is open to a large family room with a second fireplace, and from there a door leads out to a screened porch overlooking the grounds. The primary suite has vaulted ceilings, two walk-in closets and a private balcony.
Downstairs, the finished walk-out lower level has a large recreation room, a wine cellar, a gym and another bedroom with a full bath. Behind the home are a screened gazebo with a television, a broad patio and an outdoor kitchen with a barbecue. The attached three-car garage is heated and has electric-vehicle charging. The property last sold for $3.535 million in 2015.
Stacey H. Rechler and Megan S. Sullivan of Douglas Elliman Real Estate were the listing agents. Gina Waldman of Compass Greater NY, LLC represented the buyer.
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No. 4 — $3,800,000 · 455 Polly Park Road, Rye, New York
The oldest home in this week’s group comes with a family story. According to the listing, Hobart Park built the Rye Colonial in 1909 as a wedding gift for his daughter, Polly Park. The wood-sided home sits on 1.73 acres that back onto the West Course at the Westchester Country Club, and it sold for $3,800,000.
The two-story home has three bedrooms, three full baths and 3,675 square feet. An open kitchen and family room anchor the first floor, which also has a dining room, a living room, a sun room, a full bath and a mudroom. Out back, a brick patio shaded by awnings steps down to a second patio with an outdoor kitchen, overlooking the landscaped grounds and the golf course. There is a detached two-car garage.
The property also has a barn that was taken down to its foundation and rebuilt with Vermont trusses and six-inch siding, reusing some of the original wood.
The home went under contract 12 days after it was listed and sold for $105,000 above its asking price of $3.695 million. Amie A. Pisano of Compass Greater NY, LLC and Beth Delaney of William Raveis-New York LLC were the listing agents. Michael P. McCooey of Compass Greater NY, LLC represented the buyer, as on the Highland Road sale at the top of the list.
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No. 5 — $3,650,000 · 162 Kirby Lane, Rye, New York
A clapboard Colonial from 1924 on Kirby Lane in Rye, with views across Kirby Lane Pond, sold for $3,650,000. The home stands on 1.10 acres, with a stone or brick wall on the lot.
Its open living and dining areas take in the water through oversized windows, and a cupola brings more light into the interiors. The two-story home has four bedrooms, two full baths and one half bath in 2,543 square feet, with the primary bedroom on the first floor, a fireplace in the living room and an attached two-car garage. Rye’s beach clubs and the shoreline are close by, as are the shops, restaurants and schools of downtown.
April W. Saxe represented the buyer and was a listing agent with Patti Neave, so the same agent was on both sides of the sale. Both are with Compass Greater NY, LLC, which also had a listing on the Polly Park Road sale.
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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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