These Homes Will Have You Dreaming of Vacation All Year Long

These gorgeous homes can be weekend, or year-round, retreats.

Why reserve only a few weeks of the year to chill by a pool, take a dip in the lake, or go horseback riding? For those seeking a vacation lifestyle 24/7 or for people in the market for a second house, there are desirable options in Westchester and over the border. What’s on second-home buyers’ wish lists? “Weekenders want turnkey, ready to move in and enjoy, and they like low maintenance — doing the work or managing renovations is a headache for them,” says Sally Slater of Douglas Elliman. “They prefer to be on a lake or some body of water and to have access to amenities like a pool or tennis court, and hiking and riding trails.” With these trends in mind, we rounded up houses (from laid-back to luxury) that work as weekend getaways or year-round retreats.    

Nature’s Playground

Location: 13 Meadowbrook Rd, Katonah 

List Price: $3,700,000  

- Advertisement -

Square Footage: 11,384

This estate’s park-like grounds extend over eight acres, with an apple orchard, room for farm animals, a putting green, and playing field. Besides the natural setting, the standout resort-style amenity here is the heated indoor saltwater pool in an atrium-style space with cupola and cathedral-height windows overlooking the grounds. The recreation wing houses a sauna, steam room, pool room with two bars, sunrooms with chaises, and stone patio set under a wisteria-covered pergola. Throughout the home, an open-plan interior with updated design affords ample room for family and friends. Think: large family rooms with fireplaces, a master suite, and seven other bedrooms

Listed With: Melissa Frank Lutz, Douglas Elliman; 914.232.3700


Horse Lovers

Location: 48 David’s Way, Bedford Hills

- Partner Content -

List Price: $2,995,000 

Square Footage: 4,970

Set on four acres, this farm adjacent to some of the best riding trails in Bedford features a state-of-the-art barn with space for up to four horses, plus a tack room and riding ring. The updated four-bedroom, five-bath house features some country character, with barn beams and a stone fireplace in the family room in the master bath and an all-season sunroom. Outside, terraces, a professionally landscaped perennial garden, outdoor kitchen, and heated pool are the stage for outdoor living. 

Listed With:Camille Branca and Sally Slater, Douglas Elliman; 914.234.4590


- Advertisement -

Luxe on the Lake

Location: 14 Makepeace Hill, Waccabuc

List Price: $2,950,000

Square Footage: 4,697

Even the address is serene at this Waccabuc retreat overlooking Lake Whatmore. It has 700 feet of direct waterfront and a dock on the private lake. The remodeled house has four bedrooms and affords water views from almost every room. Outdoor living begins with the elevated covered terrace, living, and dining area with outdoor kitchen, wet bar, and firepit, and continues with a separate area for the pool with cabana, Har-Tru tennis court, and bocce. The setting on 10 acres rivals what you might find in Vermont or Maine, but the house is only 57 miles from New York City.  

Listed With: David Turner, Houlihan Lawrence; 914.234.9009


Family Compound

Location: 55 Lakefront Rd, Putnam Valley 

List Price: $1,055,000

Square Footage: 3,000 plus guest cottage

Just over the border from Westchester, into the Hudson Highlands, the town of Putnam Valley — nicknamed the Town of Lakes — feels less like the burbs and more like the country. The house overlooks Lake Oscawana (one of the few lakes in the area that allows motor boats; it’s been the filming location for episodes of Homeland) and features four bedrooms, a living room with stone fireplace, a glassed-in family room, and large master suite. A cedar A-frame guest cottage connects to a private lake beach and a T-shaped boat dock. There’s additional studio space above the detached four-car garage. The house is one hour from Manhattan.  

Listed With: Gary Margolis, Exprop Real Estate; 854.628.0566  

Our CEOs & Business Leaders Golf Outing is August 5!

Our Best of Westchester Party is July 24!

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.