About 280 Highland Road
"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.
Features of 280 Highland Road
| MLS® # | 994413 |
|---|---|
| Price | $6,495,000 |
| Bedrooms | 7 |
| Bathrooms | 7.00 |
| Full Baths | 6 |
| Half Baths | 1 |
| Internal Footage | 7,497 |
| Square Footage | 104980 |
| Acres | 2.41 |
| Year Built | 1928 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Colonial |
| Status | Pending |
Community Information
| Address | 280 Highland Road |
|---|---|
| City | Rye |
| County | Westchester County |
| State | NY |
| Zip Code | 10580 |
Amenities
| Utilities | Cable Connected, Electricity Connected, Natural Gas Connected, Propane, Sewer Connected |
|---|---|
| Parking | Detached, Driveway, Garage, Garage Door Opener |
| # of Garages | 3 |
| Is Waterfront | No |
| Has Pool | Yes |
| Pool | Fenced, In Ground, Pool Cover, Pool/Spa Combo |
Interior
| Interior | Combination, Hardwood, Tile |
|---|---|
| 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 |
| Appliances | Convection Oven, Dishwasher, Disposal, Dryer, Electric Oven, Exhaust Fan, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator |
| Heating | Hydro Air, Natural Gas, Oil, Propane, Radiant, Radiant Floor |
| Cooling | Attic Fan, Central Air, Ductless, Zoned |
| Fireplace | Yes |
| # of Fireplaces | 6 |
| Fireplaces | Decorative, Gas, Wood Burning |
| Has Basement | Yes |
| Basement | Unfinished |
Exterior
| Exterior Features | Garden, Tennis Court(s) |
|---|---|
| Lot Description | Back Yard, Front Yard, Garden, Landscaped, Level, Near Golf Course, Near Public Transit, Near Shops, Private, Sprinklers In Front, Sprinklers In Rear |
| Windows | Blinds, Oversized Windows |
| Construction | Shingle Siding |
School Information
| District | Harrison |
|---|---|
| Elementary | Harrison Avenue Elementary School |
| Middle | Louis M Klein Middle School |
| High | Harrison High School |
Additional Information
| Date Listed | May 15th, 2026 |
|---|---|
| Days on Market | 142 |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Listing Provided Courtesy of | Houlihan Lawrence Inc. |
|---|---|
| Contact Info | 914-967-7680 |