280 Highland Road • Rye, NY 10580

$6,495,000 • Beds: 7 • Baths: 6 full 1 partial • Sq. Feet: 7497 • MLS ID: 994413 • Subdivision: • School Dist: Harrison
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 covered porch overlooking a stunning salt water Shoreline pool with spa, custom pool house, full tennis court, outdoor kitchen & grilling station, firepit area, and spacious 3-car garage with additional storage. Located at 280 Highland Road, this premier property combines timeless architectural elegance with current refined finishes, and seamless indoor-outdoor living featuring four covered porches. Grand circular drive with pillared entryways welcome you into this sun-filled stately residence showcasing classic 1900s charm, gracious-scale rooms, reimagined to create a modern updated design for today's lifestyle. Recently renovated Chef's Kitchen features top of the line appliances : Wolf 6-burner with griddle gas cooktop, Wolf microwave, Wolf double wall oven, Sub-Zero refrigerator, two paneled dishwashers, two sink areas. Quartz waterfall island countertop seats 4, Dining Area for 8+ plus fabulous Walk-in Versatile Pantry/Back Kitchen. Covered porch side entrance to fantastic Custom Mudroom with five built-in cubbies with endless storage and two work stations adjacent to the Laundry Room, offers the utmost in convenience and efficiency. The spectacular outdoor setting is ideal for casual living and extensive entertaining, featuring expansive patios, multiple dining areas, manicured gardens, resort-inspired 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 as referenced in the 1930s, offers a rare opportunity to have a private sanctuary to enjoy quality time with your family and friends in this very special setting, in a sought-after location in Westchester County. View this listing at: http://monagold.laffey.com/mls=994413

Property Features

  • Garage: 3
  • Taxes: $61,627
  • Basement: Yes
  • Fenced: Yes
  • Swimming Pool: Yes
  • Exterior: Shingle Siding
  • Lot Size: 2.41 Acres
  • Heating: Hydro Air,Natural Gas,Oil,Propane,Radiant,Radiant
  • Cooling: Attic Fan,Central Air,Ductless,Zoned
  • Year Built: 1928
  • Fireplaces: 6
  • Security: yes
  • Water: Private,Public
  • Sewer: Public Sewer
  • On Market Date: 2026-05-20
  • Appliances: Convection Oven,Dishwasher,Disposal,Dryer,Electric Oven,Exhaust Fan,Gas Cooktop,Microwave,Refrigerator,Stainless Steel Appliance(s),Washer,Wine Refrigerator
  • Basement: Unfinished
  • Building Area Total: 8138
  • Exterior Features: Garden,Tennis Court(s)
  • Fireplace Features: Decorative,Gas,Wood Burning
  • Fireplace Y/N: Yes
  • Flooring: Combination,Hardwood,Tile
  • GarageY/N: Yes
  • Interior Features: Breakfast Bar,Built-in Features,Chandelier,Chefs Kitchen,Crown Molding,Double Vanity,Eat-in Kitchen,Entrance Foyer,High Ceilings,His and Hers Closets,Kitchen Island,Pantry,Primary Bathroom,Quartz/Quartzite Counters,Recessed Lighting,Soaking Tub,Storage,Walk-In Closet(s),Wet Bar
  • Laundry: Laundry Room
  • Lot Features: Back Yard,Front Yard,Garden,Landscaped,Level,Near Golf Course,Near Public Transit,Near Shops,Private,Sprinklers In Front,Sprinklers In Rear
  • Attic: Dormer,Partial
  • Included In Taxes: Sewer,Trash
  • Number Of Kitchens: 1
  • Heating Zones: 6
  • Other Structures: Garage(s),Outdoor Kitchen,Pool House
  • Parcel Number: 2801-000-546-00000-000-0056
  • Parking Features: Detached,Driveway,Garage,Garage Door Opener
  • Patio And Porch: Covered,Patio,Porch,Wrap Around
  • Pool Features: Fenced,In Ground,Pool Cover,Pool/Spa Combo
  • Rental Term: Monthly
  • Rooms Total: 14
  • Security Features: Security System,Smoke Detector(s)
  • Spa Y/N: Yes
  • Utilities: Cable Connected,Electricity Connected,Natural Gas Connected,Propane,Sewer Connected
  • Window Features: Blinds,Oversized Windows

School Information

  • High School: Harrison High School
  • Middle School: Louis M Klein Middle School
  • Elementary School: Harrison Avenue Elementary School
  • School District: Harrison
Printed May 22, 2026

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