280 Highland Road | MLS #994413 | RE/MAX of New York

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.

Source: OneKey MLS, MLS#: 994413

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Property Type

Residential
Lot

2.41 acres

General

Association/HOA

Association: No

School Information

School District: Harrison
Elementary School: Harrison Avenue Elementary School
Middle Or Junior School: Louis M Klein Middle School
High School: Harrison High School

Building Information

Year Built: 1928

Location/Region

County Or Parish: Westchester County
Postal City: Rye

Rent/Lease Information

Lease Considered: No

Tax Information

Tax Annual Amount: 61627
Tax Assessed Value: 36150
Tax Year: 2025

General Information

Parcel Number: 2801-000-546-00000-000-0056
Property Condition: Updated/Remodeled
Property Sub Type: Single Family Residence
Property Type: Residential
Senior Community: No
Special Listing Conditions: None

Interior

Parking Information

Garage Spaces: 3
Garage: Yes

Beds/Baths

Bathrooms Full: 6
Bathrooms Half: 1
Bathrooms Total: 7
Bedrooms Total: 7

Building Interior

Building Area Source: Appraiser
Building Area Total: 8138
Building Area Units: Square Feet

General Information

Appliances: Convection Oven,Dishwasher,Disposal,Dryer,Electric Oven,Exhaust Fan,Gas Cooktop,Microwave,Refrigerator,Stainless Steel Appliance(s),Washer,Wine Refrigerator
Cooling: Attic Fan,Central Air,Ductless,Zoned
Fireplace Features: Decorative,Gas,Wood Burning
Fireplace: Yes
Fireplaces Total: 6
Flooring: Combination,Hardwood,Tile
Heating: Hydro Air,Natural Gas,Oil,Propane,Radiant,Radiant Floor
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
Laundry Features: Laundry Room
Levels: Three Or More
Living Area: 7497
Living Area Source: Appraiser
Rooms Total: 14
Security Features: Security System,Smoke Detector(s)
Spa: Yes
Window Features: Blinds,Oversized Windows

Exterior

Parking Information

Parking Features: Detached,Driveway,Garage,Garage Door Opener

Lot Information

Lot Features: Back Yard,Front Yard,Garden,Landscaped,Level,Near Golf Course,Near Public Transit,Near Shops,Private,Sprinklers In Front,Sprinklers In Rear
Lot Size Acres: 2.41
Lot Size Square Feet: 104980
Water Source: Private,Public

Waterfront/View

Waterfront: No

Building Exterior/Construction

Architectural Style: Colonial
Construction Materials: Shingle Siding
Patio And Porch Features: Covered,Patio,Porch,Wrap Around
Property Attached: No

General Information

Carport: No
Exterior Features: Garden,Tennis Court(s)
Horse: No
Other Structures: Garage(s),Outdoor Kitchen,Pool House
Pool Features: Fenced,In Ground,Pool Cover,Pool/Spa Combo
Pool Private: Yes
Sewer: Public Sewer
Utilities: Cable Connected,Electricity Connected,Natural Gas Connected,Propane,Sewer Connected

Room Information

Level: First
Description: MAIN HOUSE FIRST FLOOR: Dramatic Front Entrance Foyer graciously creates natural flow throughout the first floor opening to an Entertainment Sized Living Room with multiple seating areas gas fireplace/Showstopping wet bar/ Formal Dining Area easily seats 10+ with a beautiful backdrop of three large 12 over 12 windows with amazing views, French Dr Entry with privacy glass from Foyer to stunning Library with cherry wood windows and trim/ handsome built-in bookshelves flanking the wood burning fireplace with easy access to renovated Formal Powder Rm/ Stroll through the deep Front Foyer to enter the generous Family Room with wood-burning fireplace with double entrances to the stunning renovated Chef's Kitchen featuring high end stainless appliances/Quartz countertops & Waterfall Island with seating for 4 / Walk-in Pantry/Back Kitchen work space/ Coffee and juice Bar, plus Dining Area seating 8+ overlooking the breathtaking private backyard and pool area...

Level: First
Description: MAIN HOUSE First Floor continued .... Entrance to the huge Mudroom with 5 cubbies/shelves, 2 built -in work stations with adjacent Laundry Room conveniently tucked behind the front staircase with side entrance and covered porch offering high functionality for day to day living. This floor plan offers the perfect blend of living space to enjoy a Formal lifestyle of a carefully curated home, while having wonderful casual living space for day to day activities.

Level: Other
Description: POOL HOUSE: Open floor plan with Vaulted Ceiling : Kitchen Area with large quartz peninsula with bar stool seating for 4/ Generous sitting area/ Plenty of Room for Game Table, Full Bath, Storage Closets

Level: Second
Description: MAIN HOUSE SECOND FLOOR: Private sun-filled Primary Suite with fireplace/ Luxurious Primary Bath ensuite with large stall shower/ claw foot tub/ large double vanity sink/ separate WC/ Dual walk- in closets, Steps up to large Hall, Bedroom/Renovated Bath/ Bedroom, Bedroom/ Recently Renovated Ensuite Bath, Bedroom/ Home Office

Level: Third
Description: MAIN HOUSE THIRD FLOOR: Oversized Bedroom with separate Sitting Area/ Renovated Bath/ Walk-in Closet, Bedroom, Renovated Hall Bath, Playroom, Large Cedar Closet, Attic Utility Closet

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Down Payment

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Loan Length (years)

Interest Rate

* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

Life at 280 Highland Road

Schools

School data courtesy of LiveBy, Inc.

Ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating. The schools displayed on this website are for informational purposes only and may not represent a complete or up-to-date list. School assignments are subject to change and should be verified directly with the local school district. Please contact the appropriate school district to confirm school zoning and enrollment eligibility for this property.

History

Date	Event	Value
6/11/2026Source: OneKey MLS	Status Change	Pending
5/20/2026Source: OneKey MLS	Status Change	Active
5/15/2026Source: OneKey MLS	Added to Database	May 15, 2026

Listing provided courtesy of Houlihan Lawrence Inc.Donna McElwee- MLS# 994413

Contact Information: 914-967-7680

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