280 Highland Road, Rye, NY 10580

• 7 beds |
• 7 baths |
• 7,497 sqft

Property Description

"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.

Listing Status:

Active

Data Last Updated:

May 21, 2026 at 7:22AM

Listing Office:

Houlihan Lawrence Inc. : 914-967-7680

MLS ID:

994413

Interior

• General: Breakfast BarBuilt-in FeaturesChandelierChefs KitchenCrown MoldingDouble VanityEat-in KitchenEntrance FoyerHigh CeilingsHis and Hers ClosetsKitchen IslandPantryPrimary BathroomQuartz/Quartzite CountersRecessed LightingSoaking TubStorageWalk-In Closet(s)Wet Bar
• Appliances: Convection OvenDishwasherDisposalDryerElectric OvenExhaust FanGas CooktopMicrowaveRefrigeratorStainless Steel Appliance(s)WasherWine Refrigerator
• Laundry: Laundry Room
• Basement: Unfinished
• Flooring: CombinationHardwoodTile
• A/C: Attic FanCentral AirDuctlessZoned
• Heating: Hydro AirNatural GasOilPropaneRadiantRadiant Floor
• Fireplace: DecorativeGasWood BurningFireplaceFireplaces: 6

Exterior

• General: GardenTennis Court(s)
• Style: Colonial
• Other Structures: Garage(s)Outdoor KitchenPool HousePorchWrap AroundPatioCovered
• Pool: FencedIn GroundPool CoverPool/Spa Combo
• Parking: DetachedDrivewayGarageGarage Door Opener

Construction

• Windows: BlindsOversized Windows
• General: Three Or More

Location

• Originating MLS: onekey2
• School District: Harrison
• County: Westchester County

Lot

• Zoning: 2801-000-546-00000-000-0056

Utilities

• Utilities: Cable ConnectedElectricity ConnectedNatural Gas ConnectedPropaneSewer Connected
• Water: PrivatePublic
• Sewer: Public Sewer

Financial

• Source: onekey2