$2,299,000
5 Bed • 4.5 Bath • 4,661 Sq. Ft.
20 Hitching Post Lane
Chappaqua, NY 10514
Listed with William Raveis-New York LLC
$3,250,000
Est. $19,664/moPound Ridge, NY 10576 · Westchester County
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The Cross Pond Residence, designed by acclaimed architect Frank Lupo, FAIA, is a rare architect-designed estate set on 3.48 private acres overlooking a large pond in Pound Ridge. Conceived as a series of interconnected structures thoughtfully positioned within the landscape, the property offers a level of design, craftsmanship, and flexibility seldom found in residential architecture. The main residence is organized around dramatic living spaces that embrace the surrounding landscape through expansive walls of glass, soaring ceilings, and carefully framed views of the water and grounds. The primary living area flows seamlessly to dining and kitchen spaces, creating an environment equally suited for everyday living and entertaining. The upper level serves as a private retreat with a spacious primary suite, while the lower level provides additional recreation and gathering space. Complementing the main residence is a fully self-contained secondary living quarters featuring its own living room, dining area, kitchen, bedroom, elevator, and private primary suite. Ideal for extended family, guests, live-in staff, or multigenerational living, it offers complete independence while remaining architecturally integrated with the overall composition. Additional structures include a substantial heated studio building with exceptional flexibility for creative work, hobbies, fitness, collector use, or additional vehicle storage, as well as a detached six-car garage with front and rear access, providing ample space for automobiles, equipment, and storage. Constructed with a level of detail and material quality rarely seen today, the residence incorporates steel framing, glulam beams, commercial-grade window systems, lead-coated copper roofing, standing-seam metal roofing, cedar siding, radiant heating, humidity control, and a hydraulic elevator. The result is a home designed not only for visual impact, but for longevity and performance. The grounds are equally compelling, with expansive lawns, mature trees, exposed rock outcroppings, gardens, and a large pond that serves as the focal point of the property. The landscape was conceived as an extension of the architecture, creating a seamless relationship between built form and nature. For buyers seeking additional outdoor amenities, the property offers attractive opportunities for a future pool installation. Conceptual plans have been prepared illustrating both a garage-side pool pavilion overlooking the pond and a more secluded pool retreat adjacent to the studio building, allowing future owners to tailor the outdoor experience to their lifestyle and entertaining preferences. Published in The New American House 2: Innovations in Residential Design and Construction, The Cross Pond Residence represents a rare opportunity to own an architecturally significant estate where design, landscape, and function exist in complete harmony.
As reported by the listing office; verify enrollment with the district.
Listed with Compass Greater NY, LLC · Adam Hade · Source: OneKey MLS
Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 17, 2026, 6:08 PM ET. ©2026 One Key MLS.
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Market Insights
Current Listings
New in the last 30 days
12
Sep 2026
Average Price
Active listings
$2,637,930
Sep 2026
Average Days on Market
Active listings
142 days
Sep 2026
Computed from 43 active OneKey MLS listings in Pound Ridge, NY.
$2,299,000
5 Bed • 4.5 Bath • 4,661 Sq. Ft.
20 Hitching Post Lane
Chappaqua, NY 10514
Listed with William Raveis-New York LLC
$3,595,000
6 Bed • 7 Bath • 5,972 Sq. Ft.
69 Rye Road
Rye, NY 10580
Listed with Houlihan Lawrence Inc.
$2,395,000
5 Bed • 4 Bath • 3,579 Sq. Ft.
7 Poplar Road
Larchmont, NY 10538
Listed with Julia B Fee Sothebys Int. Rlty