280 Highland Road

Rye, NY 10580 Directions
$6,495,000
  • 7Bed
  • 6/1Baths
  • 8,138Sqft
  • 2.41Acres
  • 1928Built
  • ColonialStyle

Property Highlights

  • School District: Harrison
  • Elementary: Harrison Avenue
  • Municipality: Rye
  • Price/Sqft: $798
  • Days on Market: 8
  • MLS: 994413
  • Taxes: $61,627
  • Listing Pending

Property Highlights

  • School District: Harrison
  • Elementary: Harrison Avenue
  • Municipality: Rye
  • Price/Sqft: $798
  • Days on Market: 8
  • MLS: 994413
  • Taxes: $61,627
  • Listing Pending

"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...

Property Highlights

  • School District: Harrison
  • Elementary: Harrison Avenue
  • Municipality: Rye
  • Price/Sqft: $798
  • Days on Market: 8
  • MLS: 994413
  • Taxes: $61,627
  • Listing Pending

"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.

"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.

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  • Additional Information
    • Basement Description: Unfinished
    • Days On Market: 8
    • Elementary School: Harrison Avenue Elementary School
    • Elementary School District: Harrison
    • High School: Harrison High School
    • Middle School: Louis M Klein Middle School
    • On Market Date: 2026-05-20
    • Sewer: Public Sewer
    • Style: Colonial
    • Type: Residential
    • Utilities: Natural Gas Available, Cable Connected, Electricity Connected, Natural Gas Connected, Propane, Sewer Connected
    • Year Built: 1928
  • Interior Features
    • Appliances Included: Convection Oven, Dishwasher, Disposal, Dryer, Electric Oven, Exhaust Fan, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator
    • Beds: 7
    • Cooling: Attic Fan, Central Air, Ductless, Zoned
    • Flooring: Combination, Hardwood, Tile
    • Full Baths: 6
    • Heat: Natural Gas, Oil, Propane, Radiant, Radiant Floor
    • Interior Features: Breakfast Bar, Built-in Features, Chandelier, Crown Molding, Double Vanity, Eat-in Kitchen, Entrance Foyer, High Ceilings, His and Hers Closets, Kitchen Island, Pantry, Recessed Lighting, Soaking Tub, Storage, Walk-In Closet(s), Wet Bar
    • Living Area SqFt: 7497
    • Rooms: 14
  • Exterior Features
    • Construction Materials: Shingle Siding
    • Exterior Features: Garden, Tennis Court(s), Covered, Patio, Porch, Wrap Around, Pool (Fenced, In Ground, Pool Cover, Pool/Spa Combo, Private)
    • Parking: Detached, Driveway, Garage, Garage Door Opener
  • Assessed Value and Taxes
    • Tax Amount: $61,627
William Pitt / Julia B. Fee Sotheby's International Realty

Rye Brokerage

49 Purchase Street
Rye, NY 10580
Listing Courtesy of Donna McElwee of Houlihan Lawrence Inc.
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