
Overtheway, an exceptional luxury estate, is tucked away on 2.4 beautifully landscaped private acres showcasing a meticulously renovated 7-bedroom | 5.1-bath Dutch Colonial in Rye, NY as its centerpiece. This private compound offers resort-style living with a wraparound porch overlooking a stunning Shoreline pool, custom pool house, full tennis court, outdoor kitchen & grilling station, firepit area, and spacious three-car garage with additional storage. Located at 280 Highland Road, this premier property combines timeless architectural elegance with modern luxury upgrades and seamless indoor-outdoor living.
Grand circular pillared entryways welcome you into this sun-filled stately residence showcasing classic 1900s charm, gracious-scale rooms, refined finishes, and a modern updated floor plan designed for today’s lifestyle. The spectacular outdoor setting is ideal for casual living and extensive entertaining, featuring expansive patios, multiple dining areas, manicured gardens, resort-inspired pool amenities, and private recreational spaces.
Ideally located within walking distance to downtown Rye, Metro-North train, boutique shopping, and top restaurants, you will have every amenity desired. Just minutes to Westchester Country Club, Apawamis Club and Harrison Meadows. Nearby Westchester County Airport and NYC LaGuardia Airport makes travel effortless. Overtheway offers a rare opportunity to have a private sanctuary to enjoy quality time with your family and friends in a very special setting, in a sought-after location in Westchester County.
Rye Metro-North Train Station
Westchester County Airport
Offering commercial, business, and private aviation services
Apawamis CC
Westchester CC
Harrison Meadows GC
Westchester CC Beach Club
Manursing Island Club
Coveleigh Club
Shenorock Shore Club
American Yacht Club
Rye Golf Club
Rye Town Park & Oakland Beach
Downtown Rye
Rye Nature Center
Edith G. Read National Park / Sanctuary
The Rye Arts Center

With 30+ years of experience, Donna and Scott expertly guide clients through every stage of the real estate process. Their seamless partnership ensures broad exposure, 24/7 availability, and efficient, client-focused service. From showings to negotiations, they deliver exceptional results.
Drawing on their Wall Street careers—Donna as a salesperson and Scott as a trader—they bring deep market insights and data-driven advice. Donna’s staging expertise and design instincts ensure homes shine in photography, video, and showings.
As longtime Rye residents, Donna and Scott are deeply rooted in the community and surrounding areas, offering invaluable local knowledge. Their dedication to creative marketing, personalized service, and informed decision-making makes them trusted advisors for buyers and sellers alike.