A truly rare Chappaqua mini-estate with pool and tennis, offering resort-style living just a short walk from the town and train. Privately perched atop a hill and approached by a sweeping stone-lined driveway, this property delivers an exceptional blend of privacy, presence, and convenience—moments from shops, dining, and Metro-North. The expansive grounds are designed for all-season enjoyment, featuring a heated pool, tennis court, playground, and putting green, creating a true at-home retreat rarely available so close to town. A classic wraparound porch sets the tone for relaxed indoor-outdoor living, perfect for morning coffee, sunset cocktails, and effortless entertaining overlooking the beautifully landscaped property. The home balances estate-style scale with a warm, welcoming feel, making it equally suited to large gatherings and everyday living. An irreplaceable , country-chic Chappaqua offering where land, privacy, and best-in-class amenities meet true walk-to-all convenience—an ideal opportunity for buyers seeking a mini-estate lifestyle in a prime, in-town location.
Est. $6,020 per month, based on comparable rentals
Sale and tax history for 276 Quaker Rd
Sale History
Tax History
Date
Event
Price
OneKey® MLS as Distributed by MLS Grid #944162
Jul 14, 2026
Sold
$2,875,000
$440/sq ft
Feb 18, 2026
Pending
—
Feb 5, 2026
Listed
$2,750,000
$421/sq ft
Feb 1, 2026
Coming Soon
$2,750,000
$421/sq ft
OneKey® MLS as Distributed by MLS Grid #H4701191
Jun 2, 2017
Sold
$1,800,000
$276/sq ft
Mar 4, 2017
Contingent
—
Feb 26, 2017
Listed
$1,839,000
$282/sq ft
One of a kind mini estate w pool & tennis in walk-to-all location (train & village).Unique renovated Victorian Colonial offers hilltop privacy, the charm & grace of yesteryear, w modern amenities, updates & renovations.Up a sweeping driveway lined w stone walls, the wraparound porch welcomes you.4 finished flrs provide space for entertaining, quiet respite & family gatherings.High ceilings throughout, antique wide board flrs, stained glass, & a Klaffs custom gourmet kitchen open to an expansive fam rm w skylights, a large eat-in area w FPL,a mud rm & computer area. Thru Fr Drs is a separate study/office w bay window, & stunning FDR & FLR w fireplace & custom inlaid floors. 6 BR's on the 2 upper flrs, including a gracious MBR suite, have large windows , multiple exposures, & abundant natural light. The top fl recreation/billiard rm & gym provide distant views. The LL play rm & music room is walk-out. A playground & putting green compliment the property. Classic architecture at its best. Additional Information: Amenities:Tennis,HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Detached,
HGMLS #4514974
Aug 11, 2015
Price Changed
$1,735,000
$266/sq ft
Aug 11, 2015
Sold
$1,735,000
$266/sq ft
Jun 30, 2015
Contingent
—
Jun 30, 2015
Price Changed
$2,000,000
$306/sq ft
May 1, 2015
Listed
$2,000,000
$306/sq ft
"The Past Perfected" Enter through stone pillars, then up the driveway to this 6 bedroom Victorian within walking distance to town and train. Landscaped 2.68 acres feature manicured lawn and gardens with heated gunite pool, Har-tru tennis court, 3 hole putting green with sand trap, children's play area. The house has the perfect layout for today's casual lifestyle but all the room and amenities for elegant entertaining. The most delightful space may be the big front porch or the wrap around deck w hot tub and views. The entire house has been renovated creating comfort and convenience throughout. Large rooms, high ceilings, oversized windows and wide plank floors add to the charm. A chef's kitchen opens into family room with door to deck. The beautiful room proportions and oversized windows create a sense of space and design not commonly seen today. A must see! .