280 Highland Road, Rye, NY, 10580
14 rooms
7 beds
6 Full / 1 Half baths
1928
Colonial
7,497 sqft
"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, adapted 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.
Status:
Coming Soon
On Market Date:
05/20/2026
Type:
Single-family residential
Laundry Remarks:
Laundry Room
Garage:
3-car
Heating:
Hydro Air, Natural Gas, Oil, Propane, Radiant
Cooling:
Attic Fan, Central Air, Ductless, Zoned
Basement:
Unfinished
Parking:
Detached, Driveway, Garage, Garage Door Opener
Acreage:
2.41
Est. Taxes:
$61,627
Assessment
$36,150
Construction
Shingle Siding
Utilities
Cable Connected, Electricity Connected, Natural Gas Connected, Propane, Sewer Connected
Lot Description:
Back Yard, Front Yard, Garden, Landscaped, Level, Near Golf Course, Near Public Transit, Near Shops, Private, Sprinklers In Front, Sprinklers In Rear
Elementary School:
Harrison Avenue Elementary School
Middle School:
Louis M Klein Middle School
High School:
Harrison High School
School District:
Harrison
Appliances:
Convection Oven, Dishwasher, Dryer, Exhaust Fan, Gas Cooktop, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator
Pool:
Fenced, In Ground, Pool Cover, Pool/Spa Combo
MLS #:
994413
Community Info
School Info
Walk Score
Mass Transit
Yelp
Similar Properties
New or Coming Soon Properties
Listing courtesy of Houlihan Lawrence Inc. 914-967-7680