$2,349,000
5 Bed • 5.5 Bath • 5,646 Sq. Ft.
48 Random Farms Circle
Chappaqua, NY 10514
Listed with Compass Greater NY, LLC
$2,599,000
Est. $15,713/moPound Ridge, NY 10576 · Westchester County
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Step into a slice of Mediterranean paradise at 105 Cross Pond Road, where timeless elegance meets modern luxury. This breathtaking villa, inspired by classic European architecture, boasts over 6,000 square feet of refined living space on 5.+ meticulously landscaped acres. From the iconic red clay roof to the graceful stucco and stately arches, this property exudes sophistication at every turn. Key Features That Will Steal Your Heart: Mediterranean Charm: The distinctive architectural elements create an enchanting, old-world aesthetic. Expansive Interiors: Multiple fireplaces, private terraces, and oversized balconies invite seamless indoor-outdoor living. Private Waterfront Oasis: Your very own lagoon offers tranquil views, waterside relaxation, and kayaking adventures just steps away. Luxurious Finishes Throughout: Marble and natural stone details bring warmth and elegance to every room. Nature’s Playground: Over 5+ acres of pristine grounds, complete with a private island, provide endless opportunities for outdoor entertaining and peaceful solitude. Inside the Villa: From the moment you enter, the grand scale and thoughtful design captivate. Open-concept spaces flow effortlessly, perfect for everything from quiet evenings to hosting grand gatherings. Marble and stone finishes elevate the interiors, while fireplaces add cozy charm. Step outside onto expansive terraces and balconies to savor al fresco dining or watch the sunset over your serene property. The home also offers flexible spaces ideal for a chef’s kitchen, wine room, home gym, or a luxurious primary suite. Unbeatable Location for a Coveted Lifestyle: Nestled on prestigious Cross Pond Road in Pound Ridge, this estate combines privacy with accessibility. It’s part of the highly regarded Bedford Central School District and offers convenient access to I-684, Saw Mill Parkway, and Metro-North stations for an effortless commute to Manhattan. Nature lovers will adore the proximity to Ward Pound Ridge Reservation for hiking, camping, and fishing, while the charming nearby towns of Katonah, Bedford, and Stamford, CT, provide boutique shopping, fine dining, and cultural experiences. For wine enthusiasts, local vineyards and specialty shops await to help you curate the perfect collection. A Once-in-a-Lifetime Opportunity: 105 Cross Pond Road isn’t just a home—it’s an experience. Whether you’re savoring lakeside mornings, hosting elegant, or simply enjoying the serene beauty of your surroundings, this estate offers a lifestyle of unparalleled luxury and tranquility. Don’t miss your chance to make this extraordinary retreat your own.
As reported by the listing office; verify enrollment with the district.
Listed with Compass Greater NY, LLC · Korab Krasniqi · Source: OneKey MLS
Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 23, 2026, 8:07 PM ET. ©2026 One Key MLS.
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Market Insights
Current Listings
New in the last 30 days
10
Sep 2026
Average Price
Active listings
$2,637,267
Sep 2026
Average Days on Market
Active listings
141 days
Sep 2026
Computed from 45 active OneKey MLS listings in Pound Ridge, NY.
$2,349,000
5 Bed • 5.5 Bath • 5,646 Sq. Ft.
48 Random Farms Circle
Chappaqua, NY 10514
Listed with Compass Greater NY, LLC
$2,195,000
4 Bed • 4.5 Bath • 2,793 Sq. Ft.
23 Holly Place
Larchmont, NY 10538
Listed with Douglas Elliman Real Estate
$1,850,000
5 Bed • 3.5 Bath • 4,200 Sq. Ft.
28 Observatory Drive
Croton-on-Hudson, NY 10520
Listed with Houlihan Lawrence Inc.