Westchester’s 15 Most Expensive Homes

Photo courtesy of Houlihan Lawrence


77 Oregon Rd, Bedford Corners

8 BR, 7.1 BA; 10,000 sq. ft.; 63.8 acres; $176,000 estimated taxes

By far the most expensive home currently on the Westchester market, this estate warrants its jaw-dropping price largely because of its unrivaled location: nearly 64 prime acres in Bedford, populated with maple, apple, and pear trees, and offering celeb-worthy privacy (who else could afford this?) and bucolic views in every direction. The grounds include heated pool; cabana with fireplace, bar area, and changing room; tennis court; putting greens; and a guesthouse.

The main house — a striking brick Georgian fronted by four massive white columns — offers 10,000 square feet of luxury living, with everything you’d imagine at this price point: Details like custom millwork, wide-plank hardwood floors, intricate paneling, and graceful archways; the quintessential (yet modern) entryway, featuring a dramatic curved staircase; bonus rooms, like a richly paneled library, a gabled recreation room, and garden room with brick floor; and a stellar second-floor master suite complete with fireplace, private balcony, marble-appointed bath, and ample closets. Though lavish, the home is simultaneously subdued, with a vibe of classic elegance and luxury befitting its 1920s roots.

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Listed by Adam Hade, Houlihan Lawrence

Photo courtesy of Compass
Photos courtesy of Compass


8 Hickory Kingdom Rd, Bedford

7 BR, 6.2 BA; 10,957 sq. ft.; 23.29 acres; $116,856 estimated taxes

Appropriately located on Hickory Kingdom Road, this Bedford estate feels like its own storybook kingdom, thanks to 23 acres of land dotted with specimen trees, perennials, and open meadows, plus a four-acre lake. The stone manor — which overlooks the lake — was designed and built by award-winning Moisan Architects and Cornerstone Builders, with Benedek & Ticehurst contributing the landscape architecture.

Rich details abound, including arched doorways, stone fireplaces, gleaming hardwoods, slate floors, intricate millwork, and detailed paneling. The kitchen, boasting a dramatic stone hearth and wood-beamed ceiling, and the stunning all-wood study, are interior highlights, while outside, the 25’x50’ pool and stellar landscaping are sure to please.

Listed by Brian Milton, Compass

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What’s the Monthly Payment on a $10 Million Home?

We know most buyers at this level are paying cash and not sweating the monthly bills, but here’s an estimated breakdown for mortgage and taxes for the $10.49 million listing at 55 Holly Branch Rd in Katonah.

$41,141 for mortgage
(30-yr fixed at 4.221%)
$10,737 for taxes
Total: $51,878

Photo by Garrett Rowland | Courtesy of Houlihan Lawrence
Photos by Garrett Rowland | Courtesy of Houlihan Lawrence


6 Carriage Trail, Tarrytown

9 BR, 11.3 BA; 23,084 sq. ft.; 2.83 acres; $141,622 estimated taxes

There isn’t much to do but gush over this masterful home in the prestigious, new Greystone-on-Hudson development. Massive yet somehow still intimate, the 2018 home boasts a vast array of unique spaces, including a two-story mahogany library, indoor basketball court, home theater, wine cellar, entire guest wing, and a to-die-for master suite, which offers two separate bathrooms, a sitting room, two dressing rooms, and a private terrace.

Other boast-worthy features include nearly 6,000 square feet of covered porches and verandas with Hudson River views, and the home’s eco-friendly infrastructure, which includes a geothermal HVAC system.

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Listed by Elizabeth Shay, Houlihan Lawrence

Photo by Rob Lowell | Courtesy of Douglas Elliman | STAGED BY LTW DESIGN
Photos by Rob Lowell | Courtesy of Douglas Elliman | STAGED BY LTW DESIGN


340 Croton Lake Rd, Bedford Corners

12 BR, 9.3 BA; 13,791 sq. ft.;22.6 acres; $180,863 estimated taxes

Mega-celeb Bruce Willis recently put this Bedford mega-mansion on the market — and we’re dying hard for it. (Sorry, couldn’t resist.) With a Hollywood-fab-meets-family-friendly style and killer views of the Croton Reservoir, the estate includes four homes and two distinct tax lots.

The cedar-shingle-and-stone main home, at nearly 9,000 square feet, is full of chic, sleek, stylish spaces and includes five bedrooms, plus perks such as a saltwater pool, pool house, tennis court, and garaging for four cars. The second lot boasts an updated three-bedroom farmhouse and a one-bedroom home with a three-car garage.

Listed by Nancy Strong, Stacey Oestreich, and Ann Cutbill Lenane, Douglas Elliman

Photo courtesy of Coldwell Banker Residential Brokerage
Photos courtesy of Coldwell Banker Residential Brokerage


945 Forest Ave, Rye

5 BR, 4.1 BA; 4,964 sq. ft.; 1.25 acres; $123,037 estimated taxes

Waterfront access is the star of the show at this eye-popping property situated on the edge of the Rye peninsula. The custom home boasts Long Island Sound views everywhere — and with its secluded, elevated, acre-plus piece of land, privacy is assured. The Georgian Colonial, built in 2003, offers classic touches, like high ceilings, custom molding, and marble flooring, as well as such “wow” factors as a six-car heated garage that lies beneath the home.

At this high price point, some buyers may be surprised to find slightly dated décor in some rooms, including patterned wallpaper and brass fixtures. Again, this listing is all about that waterfront!

Listed by Sula Perlman and Nancy Neuman, Coldwell Banker Residential Brokerage

Which Towns Have the Most $7M+ Homes?

Rye: 5

Bedford: 5

Photo by Anthony Acocella
Photos by Tim Lenz


518 Harris Rd, Bedford Hills

7 BR, 5.2 BA; 6,776 sq. ft.; 24.26 acres; $121,427 estimated taxes

When a house has its own name, you know it’s going to be good. Windrush, this 1927 brick Georgian manor, is the archetypal Westchester luxury country home with the pedigree to prove it: Its inspiration was Cassiobury, the ancestral home of the Earls of Essex, dating back to the 16th century. Today, the house — which incorporates actual salvaged elements from Cassiobury — smacks of English equestrian charm. (It fronts the Beaver Dam Sanctuary, a perfect spot for horseback riding.)

With a vibe of understated elegance, the home offers 10 fireplaces, antique oak floors, French doors, a slate roof, reclaimed Tudor bricks, 18th-century paneling, and antique hardware and millwork. The expansive grounds include an enclosed courtyard, two gate houses, a 20’x40’ pool, goldfish pond, barn, and five-car garage.

Listed by Vincent & Whittemore Real Estate

Photo courtesy of Douglas Elliman
Photos courtesy of Douglas Elliman


18 Schoolhouse Rd, Pound Ridge

3 BR, 2 BA; 3,322 sq. ft.; 21.99 acres; $180,272 estimated taxes

Two lovely homes sit on this expansive property at the edge of Ward Pound Ridge Reservation — one a three-bedroom, two-bath with elevator and greenhouse; the other with five bedrooms and three bathrooms — but they are almost beside the point. (Ditto the indoor saltwater pool house.) The equestrian facilities are what this listing is all about: four oversized paddocks, an indoor/outdoor ring, four sand rings, an equipment house, and a custom-built post-and-beam-framed barn with 12 stalls, plus two floors of octagonal-shaped recreation/dressing rooms complete with tray ceilings. The property also has full generator backup for each building and an on-site gas/diesel station.

Listed by Lia Grasso and John Samios, Douglas Elliman

Photos by Anthony Acocella


20 Boutonville Rd, Cross River

3BR, 3.1 BA; 1,400 sq. ft.; 62 acres; $72,575 estimated taxes

Another equestrian paradise, this listing — known as Birdstone Farm — holds strong appeal for avid riders. The farm includes a professional 20-stall equestrian facility with an attached indoor ring, a 100’ x 180’ outdoor sand ring, seven large paddocks, and three run-in sheds, a three-bedroom manager’s cottage, and a groom’s apartment.

With more than 60 acres to spare (plus direct access to Ward Pound Ridge Reservation), a buyer could easily build their dream home on the property.

Listed by Vincent & Whittemore Real Estate

Photos courtesy of Douglas Elliman


44 Mead Rd, Armonk

5 BR, 4.1 BA; 5,888 sq. ft.; 33.5 acres; $125,475 estimated taxes

Looking for the ultimate in seclusion while still residing in Westchester? This may just be it. Live like a hermit — albeit a rich and fabulous one — on this 35-acre lakeside property in the exclusive Conyer’s Farm gated community. The nearly 6,000 sq. ft. Arts-and-Crafts-style home abuts a 103-acre lake and offers incredible views.

Stylistically, the house could use some updates, but it’s got plenty of lake-home charm, with touches like wood-beamed ceilings and a massive stone fireplace in the living room. Also included are a separate caretaker’s cottage and garages.

Listed by Sally Slater, Douglas Elliman

Photo by Richard Caplan
Photos by Richard Caplan


55 Holly Branch Rd, Katonah

7 BR, 7.2 BA; 7,500 sq. ft.; 40.9 acres;$128,846 estimated taxes

Like the backdrop of a Ralph Lauren ad, this graceful country estate in Bedford is the ultimate in classic American luxury. The 1930s-era whitewashed brick manor offers a stately exterior, accented with Palladian windows and black shutters, while the interior mixes equal parts cozy and grand, with spaces like an all-white kitchen, a wood-paneled study, and elegant paneled dining room.

The lush property also includes a three-bedroom guesthouse, staff apartment, 10-stall stable with groom’s apartment, fenced grass meadows, a stunning pool area, and tennis facilities.

Listed by Sally Slater, Douglas Elliman

And the Winners are…

Highest asking price:
77 Oregon Rd, Bedford Corners

Largest square footage:
6 Carriage Trail, Tarrytown

Largest acreage:
63.8 acres
77 Oregon Rd, Bedford Corners

Highest estimated taxes:
129-137 Katonahs Wood Rd, Bedford

5 More To Dream Of: Under $10 Million

Photos by Daniel Millstein Photography

310 Stuyvesant Ave, Rye

5 BR, 5.3 BA; 7,446 sq. ft.; 1.02 acres; $109,328 estimated taxes

Direct waterfront access yielding stellar Sound Shore and Manhattan views; a clean, bright, modern design; and to-die-for location mean there is nothing not to love about this custom-built Rye home. Sophisticated and family-friendly, the house features plenty of ample spaces, including a lower level with room for a fitness area, ping-pong table, and screening room.

  Listed by Lisa Hogan, William Pitt Julia B. Fee Sotheby’s International Realty

Photo courtesy of Houlihan Lawrence

129-137 Katonahs Wood Rd, Bedford

7 BR, 4.1 BA; 6,412 sq. ft.; 57.98 acres; $240,000 estimated taxes

An equestrian’s dream, this property adjoins the vast trail system of The Bedford Riding Lanes and offers 1,000 feet of frontage on the Beaver Dam River, plus an internal network of trails. On the nearly 58 acres sit an equestrian center that includes two barns (a total of 14 stalls) and indoor and outdoor riding arenas, along with a brick guesthouse, tennis court, stables, and separate guest cottage.

Listed by David Turner, Houlihan Lawrence

Photo courtesy of Houlihan Lawrence

96 Rye Rd, Rye

9 BR, 10 BA; 7,469 sq. ft.; 1.46 acres; $219,430 estimated taxes

This Long Island Sound compound offers a four-bedroom guesthouse, a one-bedroom pool/game house, waterfront pool, tennis/sports court, a private boat dock, and garaging for eight cars, plus a sprawling main home. Modern and bright, with Arts-and-Crafts-style touches and copious water views, the house offers such standout spaces as a solarium, paneled study, mirrored gym, wine closet, and master suite with spa bathroom.

Listed by Michael P. McCooey, Houlihan Lawrence

Photo courtesy of Houlihan Lawrence

73 Bellevue Ave, Rye

6 BR,  7.2 BA; 11,570 sq. ft.; 2.09 acres; $138,400 estimated taxes

Overlooking the south golf course on the grounds of Westchester Country Club, this elegant Tudor Revival home offers a perfect melding of old (leaded windows, fine woodworking, detailed moldings) and new (top-of-the-line chef’s kitchen, master suite with dual baths). Awash in elegance, the home’s showstoppers include a large brick, barrel-ceiling wine cellar with dinner seating; a billiards room with fireplace; and golf simulator room in addition to a stunning pool and outdoor entertaining area.

Listed by Michael P. McCooey, Houlihan Lawrence

Photo by Daniel Millstein Photography

4 Philips Lane, Rye

5 BR, 6.1 BA; 5,031 sq. ft.; .50 acres; estimated taxes $100,000+

A waterfront new build situated on a cul-de-sac, this custom home’s plan offers an open-concept layout with a wall of glass to let in water views. The Hamptons-esque home will include a third-floor observatory with wet bar and viewing deck. It also offers dock, beach, pool, and waterfront access on Milton Point.

Listed by Lisa McGowan and Laura DeVita, William Pitt Julia B. Fee Sotheby’s International Realty

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