The five highest-priced home sales reported in Nassau County, New York for the week ending November 8, 2026, came to a combined $21.995 million. Each sale was in a different community, from Glen Head and Syosset to Manhasset, Laurel Hollow and Great Neck, and all five were single-family homes: a sprawling modern estate, a pair of Colonials, a home with private beach access and a brick Tudor.
Daniel Gale Sothebys Intl Rlty listed the two top sales.
No. 1 — $10,350,000 · 53 Simonson Road, Glen Head, New York
The week’s top sale was an estate at 53 Simonson Road in Old Brookville, Glen Head, which sold for $10.35 million. Built in 2018 on 6.28 landscaped acres, the stone-and-stucco home has 10 bedrooms, 15 bathrooms (13 full and two half), 20,000 square feet of living space, six fireplaces and a four-car attached garage. It was the newest and largest of the five homes, on the biggest lot, and the property sits behind two private gates.
Oversized windows trimmed in black set off the facade. Inside, a marble foyer with a spiral staircase leads to a great room with soaring ceilings, a gas fireplace, a wet bar and walls of glass. The kitchen has two-tone cabinetry, professional stainless steel appliances and thick stone counters, while the family room has a fireplace with a stone mantel and natural wood built-ins. A butler’s pantry serves a formal dining room sized for 14 or more guests. The main level also has a bedroom suite for guests, a home office with its own sitting area, an elevator and a mudroom off the garage.
The primary wing upstairs has a private lounge, a dressing and vanity area, several walk-in closets with custom wardrobes, radiant heated floors and a bath with a soaking tub and a large rain shower. Four more bedrooms and four marble baths are on the same floor. The walk-out lower level opens with a foyer framed by a floor-to-ceiling wine display, and it includes a one-bedroom guest suite, a gym with a sauna, a media room or den and a full-scale golf simulator.
Outside are a covered patio with a fireplace, a built-in outdoor kitchen, an in-ground pool and spa, and a poolside cabana with a kitchenette, a lounge, changing rooms and a full bath. Elsewhere on the grounds stand a two-story barn with a loft and eight stalls, suited to horses or a car collection, and a guest house. The property last sold for $3.1 million in 2016, before the current home was built.
Jason P. Friedman and Sarah R. Friedman of Daniel Gale Sothebys Intl Rlty were the listing agents, and Xiaochen Liu of EXP Realty represented the buyer. Their brokerage also listed the week’s second-ranked sale in Syosset.
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No. 2 — $3,625,000 · 503 Cold Spring Road, Syosset, New York
A long private driveway leads to 503 Cold Spring Road in Syosset, a Colonial with a porch that wraps all the way around the home, fitted with swings at the front and the back. Built in 2006 on two acres on a cul-de-sac, the home sold for $3.625 million. It has five bedrooms, nine bathrooms (six full and three half), 6,300 square feet of living space, four fireplaces and a three-car garage.
The two-story foyer is finished in white millwork, and a series of arched openings leads to the formal dining room and to a formal living room with a fireplace and custom arched windows looking out over the grounds. The kitchen, with granite counters, Wolf and Sub-Zero appliances, custom inset cabinetry and a large pantry, is open to a breakfast area and a family room with a fireplace. The renovated primary suite has vaulted ceilings, a marble-framed fireplace and hand-painted detailing, along with a walk-in dressing room with a center island, crystal chandeliers and its own washer and dryer. Its bath has a freestanding soaking tub, a steam shower and radiant heated floors. Downstairs, the finished lower level has a music room and a recreation room, as well as a cedar closet and a gym whose sauna uses red light. The mudroom has a dog-washing station.
Outdoor living centers on a 20-by-40-foot in-ground pool, bluestone patios and a pergola with a large stone fireplace. The outdoor kitchen has a professional grill, a Big Green Egg, a granite bar with seating and its own refrigerator and ice maker. There is also a fully enclosed garden of raised vegetable and herb beds with mist irrigation. The property last sold for $2.42 million in 2010.
John W. Messina GRI was the listing agent, and Peggy M. Moriarty CBR represented the buyer. Both agents are with Daniel Gale Sothebys Intl Rlty, which listed the two top sales of the week.
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No. 3 — $3,100,000 · 55 North Drive, Manhasset, New York
The Colonial at 55 North Drive in Plandome, Manhasset, sold with village-approved plans for a renovation and an extension already in hand. Built in 1983 on 0.58 acres of flat, landscaped ground, the home has five bedrooms, five bathrooms (three full and two half), 3,432 square feet of living space and a two-car attached garage.
A skylight brightens the entry, where a two-tier staircase makes a sweeping start to the home. The living room has a wood-burning fireplace, and the family room takes in plenty of sun and looks out over the grounds. A formal dining room, a maid’s suite, a powder room and an eat-in kitchen fitted with stainless steel appliances are also on the main level, and the partially finished basement adds a half bath and storage. The backyard has a gunite pool measuring 20 by 40 feet and a hot tub, as well as a brick patio, a cabana and a shed, all set amid landscaping.
The Plandome train station is minutes away, and the home is zoned for the Manhasset School District. Membership is available at the Plandome Field and Marine Club, which offers tennis and waterfront activities. The property last sold for $2.9 million in 2023.
The home went under contract four days after it was listed and sold at its full asking price of $3.1 million. Rachel King of Serhant LLC was the listing agent, and Ann Hance of Compass Greater NY LLC represented the buyer.
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No. 4 — $2,720,000 · 38 Tiffany Road, Laurel Hollow, New York
The listing describes 38 Tiffany Road in Laurel Hollow as a custom French chateau, and the home, built in 1989 on 2.12 wooded acres within the Laurel Cove private association, sold for $2.72 million. It has four bedrooms, three bathrooms (two full and one half), 4,744 square feet of living space, two fireplaces and a two-and-a-half-car garage.
Privacy gardens frame the entrance, and inside, a wedding-style staircase rises from the foyer. The formal living room has 14-foot ceilings, a Rumford fireplace and six French doors that open to the pool and a front porch terrace. A second Rumford fireplace anchors the farmhouse-style kitchen, which opens through French doors into a glass-walled conservatory and greenhouse. The library wing has coffered ceilings, built-in bookshelves and a marble faux-tile fireplace, and the formal dining room also has coffered ceilings, with built-in cabinetry for china.
The primary suite is on the main floor, with 14-foot ceilings and floor-to-ceiling French doors to the pool and gardens. A formal dressing room with a sliding ladder leads to the bath, where the soaking tub sits beside French doors that open to the gardens. Upstairs, two staircases lead to separate bedroom wings. Seventeen French doors in all open onto grounds that include a gunite in-ground pool, a paver patio, a fountain and a fire pit. The home also has a wine cellar, a workshop and a generator.
The setting includes private beach access, views of Cold Spring Harbor, deeded mooring rights and racks for kayaks, and the community has a boat dock. Sagamore Hill, the summer home of Theodore Roosevelt, is nearby. The property last sold for $1.76 million in 2003.
Barbara L. Catapano and Michelle S. Rich of Branch Real Estate Group were the listing agents, and Vesna Oelsner of Daniel Gale Sothebys Intl Rlty represented the buyer.
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No. 5 — $2,200,000 · 1 Winfield Terrace, Great Neck, New York
The oldest of the five homes, a brick Tudor built in 1942, sold for $2.2 million at 1 Winfield Terrace in the Harbor Hills community of Great Neck, a neighborhood of waterfront and interior homes. Residents have access to the Harbor Hills pool club, tennis courts, a park and a playground, and the home is in the Great Neck Public School District. It has five bedrooms, four bathrooms (three full and one half), 3,023 square feet of living space and a two-car garage on 0.26 acres.
The renovated eat-in kitchen has two sinks and three dishwashers, and it opens to a deck overlooking a private backyard. The main level also has a formal dining room, a library, a den and a bedroom that can serve as a home office. Upstairs, the primary suite has two walk-in closets and its own bath, alongside three more bedrooms and a full bath. The finished lower level has room for recreation, fitness or a media room, and a landscaped lawn fronts the home.
Anne F. Sandler of Coldwell Banker American Homes was the listing agent, and Angela Chaman of LAFFEY REAL ESTATE represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, November 8, 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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