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$6,495,000
122 Days On Site

280 Highland Road
Rye, NY 10580

Single Family Residence|Pending
7
Beds
7
Total Baths
6
Full Baths
1
Partial Bath
7,497
SqFt
$866
/SqFt
1928
Built
County:
Westchester
Listing courtesy of Houlihan Lawrence Inc. dmcelwee@houlihanlawrence.com
280 Highland Road280 Highland Road280 Highland Road280 Highland Road
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"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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Listing Snapshot
Price 
$6,495,000
Days On Site 
122 Days
Bedrooms 
7
Inside Area (SqFt) 
7,497 sqft
Total Baths 
7
Full Baths 
6
Partial Baths 
1
Lot Size 
2.41 Acres
Year Built 
1928
MLS® Number 
994413
Status 
Pending
Property Tax 
$61,627
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
3 months agoStatus changed to Pending
3 months agoListing updated with changes from the MLS®
4 months agoListing first seen on site
General Features
Acres 
2.41
Cross Street 
Hilltop Place
Garage 
Yes
Garage Spaces 
3
Levels 
Three Or More
Parking 
DetachedDrivewayGarageGarage Door Opener
Property Condition 
Updated/Remodeled
Property Sub Type 
Single Family Residence
Security 
Security SystemSmoke Detector(s)
Sewer 
Public Sewer
SqFt Total 
8138
Style 
Colonial
Utilities 
Natural Gas AvailableCable ConnectedElectricity ConnectedNatural Gas ConnectedPropaneSewer Connected
Water Source 
PrivatePublic
Interior Features
Appliances 
Convection OvenDishwasherDisposalDryerElectric OvenExhaust FanGas CooktopMicrowaveRefrigeratorStainless Steel Appliance(s)WasherWine Refrigerator
Basement 
Unfinished
Cooling 
Attic FanCentral AirDuctlessZoned
Fireplace 
Yes
Fireplace Features 
DecorativeGasWood Burning
Fireplaces 
6
Flooring 
CombinationHardwoodTile
Heating 
Natural GasOilPropaneRadiantRadiant Floor
Interior 
Breakfast BarBuilt-in FeaturesChandelierCrown MoldingDouble VanityEat-in KitchenEntrance FoyerHigh CeilingsHis and Hers ClosetsKitchen IslandPantryRecessed LightingSoaking TubStorageWalk-In Closet(s)Wet Bar
Laundry Features 
Laundry Room
Spa 
Yes
Window Features 
Blinds
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Exterior Features
Construction Details 
Shingle Siding
Exterior 
GardenTennis Court(s)
Lot Features 
Back YardFront YardGardenLandscapedLevelNear Golf CourseNear Public TransitPrivateSprinklers In FrontSprinklers In Rear
Other Structures 
Garage(s)Outdoor KitchenPool House
Patio And Porch 
CoveredPatioPorchWrap Around
Pool Features 
FencedIn GroundPool CoverPool/Spa ComboPrivate
Private Pool 
Yes
Spa 
Yes
Windows/Doors 
Blinds
Community Features
School District 
Harrison
Schools
School District
Harrison
Elementary School
Harrison Avenue Elementary School
Middle School
Louis M Klein Middle School
High School
Harrison High School
Listing courtesy of Houlihan Lawrence Inc. dmcelwee@houlihanlawrence.com


Based on information submitted to the MLS GRID as of 2026-09-15 06:45 AM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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LUXURY HOMES • WESTCHESTER COUNTY • NEW YORK CITY

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