280 Highland Road Rye, NY $ 6,495,000
280 Highland Road
$ 6,495,000
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280 Highland Road

Rye, NY, 10580
$ 6,495,000
Bedrooms7 Baths6.1 Sq 7,497

Monthly Estimate*

$ 41,010

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Single Family Home for sale in Rye, NY

for $6,495,000 with 7 bedrooms and 6 full baths, 1 half bath. This 7,497 square foot home was built in 1928 on a lot size of 2.41.

"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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Single Family Pending

Price

$ 6,495,000

Bedrooms

7

Full Bath

6

Half Bath

1

Property Type

Single Family

Taxes

$ 61,627

Style

Colonial

Lot Size

2.41

Year Built

1928

Town/City

Rye

County/Region

Westchester

MLS | Web ID

994413

Features
Interior
Interior Amenities 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/Qua
Basement Unfinished
Flooring Combination Hardwood Tile
Total Fireplaces 6
Fireplace Features Decorative Gas Wood Burning
Basement Features Unfinished
Basement (Y/N) Y
Window Features Blinds Oversized Windows
Fireplace Y/N Y
Half Baths 1
Total Bedrooms 7
Total Baths 7
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General
Sewer Public Sewer
Heating Hydro Air Natural Gas Oil Propane Radiant Radiant Floor
Cooling Attic Fan Central Air Ductless Zoned
Utilities Cable Connected Electricity Connected Natural Gas Connected Propane Sewer Connected
Appliances Convection Oven Dishwasher Disposal Dryer Electric Oven Exhaust Fan Gas Cooktop Microwave Refrigerator Stainless Steel Appliance(s) Washer Wine Refrigerator
Garage Spaces 3
Patio/Porch Features Covered Patio Porch Wrap Around
Architectural Style Colonial
Pool Features Fenced In Ground Pool Cover Pool/Spa Combo
Security Features Security System Smoke Detector(s)
Construction Materials Shingle Siding
Year Built 1928
Property Subtype Single Family Residence
Tax Year 2025
Parcel Number 2801-000-546-00000-000-0056
County Westchester County
Property Type Residential
HOA N
Garage Y/N Y
Other Structures Garage(s) Outdoor Kitchen Pool House
Total Rooms 14
Full Baths 6
Directions Purchase St to 280 Highland Road on right coming from downtown Rye on left coming from Purchase St/ Biltmore Rd intersection
High School Harrison High School
City Harrison
Senior Community Y/N N
High School District Harrison
Carport Y/N N
Elementary School Harrison Avenue Elementary School
Property Attached Y/N N
Tax Annual Amount 61627
Middle/Junior High School Louis M Klein Middle School
Property Condition Updated/Remodeled
Virtual Tour https://www.wellcomemat.com/mls/fnf37e05a51mkt3
Building Area Units Square Feet
Standard Status Pending
Middle/Junior School District Harrison
Elementary School District Harrison
Tax Assessed Value 36150
Year Built Effective 2017
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Exterior
Exterior Amenities Garden Tennis Court(s)
Parking Features Detached Driveway Garage Garage Door Opener Detached Driveway Garage Garage Door Opener
Water Source Private Public
Spa Y
Building Area Total 8138
Waterfront Y/N N
Horse Y/N N
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Internal Only
Street Number 1 280
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* Excluded Features
List By
Donna McElwee

Listing Agent

Houlihan Lawrence Inc.

Broker

914-967-7680

Contact

Affordability Calculator

$46,146
Per Month
89%
11%
0%
Monthly Principal & Interest
$41,010
Monthly Property Taxes
$5,136
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4099780 Elementary School
4099985 Middle School
Harrison High School High School
Pricing History
DatePricePrice ChangeDescription
5/15/2026$6,495,000 Listed Price

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280 Highland Road, Rye, NY, 10580 is a Single Family Home for sale at $6,495,000 with 7,497 sqft and a lot size of 2.41. 280 Highland Road has 7 bedrooms, 6.1 baths, and was built in 1928. The property's zip code is 10580 which is in Rye, NY