Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$6,495,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 7 Beds
  • 6 Full Baths
  • 1 Partial Bath
  • 8,138 Sq. Ft.
  • 3 Car Garage
  • Updated 6 hours ago
See This Home
Save This Home
See This Home
Save This Home
"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.

Full Property Details for 280 Highland Rd

General

  • Price: $6,495,000
  • Taxes: $61,627
  • Status: Active
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 994413
  • Updated: Today (5/20/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 14
  • 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
  • Fireplace: Yes
  • Number of Fireplaces: 6
  • Fireplace(s): Decorative, Gas, Wood Burning
  • Appliances: Convection Oven, Dishwasher, Disposal, Dryer, Electric Oven, Exhaust Fan, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator
  • Laundry Facilities: Yes
  • Flooring: Combination, Hardwood, Tile

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 7

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Fenced, In-Ground, Pool Cover, Pool/Spa Combo
  • Spa: Yes
  • Security/Safety: Security System, Smoke Detector(s)

Exterior

  • Exterior Features: Garden, Tennis Court(s)
  • Porch/Patio/Deck: Covered, Patio, Porch, Wrap Around

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Parking Features: Detached, Driveway, Garage, Garage Door Opener

Location

  • County: Westchester County
  • Cross Streets: Hilltop Place
  • Driving Directions: Purchase St to 280 Highland Road , on right coming from downtown Rye, on left coming from Purchase St/ Biltmore Rd intersection

School Information

  • High School District: Harrison
  • Elementary School: Harrison Avenue Elementary School
  • Middle School: Louis M Klein Middle School
  • High School: Harrison High School

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Attic Fan, Central Air, Ductless, Zoned
  • Heating Type: Hydro Air, Natural Gas, Oil, Propane, Radiant, Radiant Floor
  • Heating Zones: 6

Utilities

  • Sewer: Public Sewer
  • Water: Private, Public
  • Utility Description: Cable Connected, Electricity Connected, Natural Gas Connected, Propane, Sewer Connected

Structural Information

  • Architectural Style: Colonial
  • Detached/Attached: Detached
  • Construction: Shingle Siding
  • Basement: Yes
  • Basement Desc.: Unfinished
  • Windows: Blinds, Oversized Windows
  • Building Size: 8138
  • Square Feet: 8,138
  • Sq. Ft. Source: Appraiser
  • Year Built: 1928

Additional Structures

  • Other Structures: Garage(s), Outdoor Kitchen, Pool House

Lot Features

  • Lot Size (Acres): 2.41
  • Lot Size (Sq. Ft.): 104,980
  • Lot Features: Back Yard, Front Yard, Garden, Landscaped, Level, Near Golf Course, Near Public Transit, Near Shops, Private, Sprinklers In Front, Sprinklers In Rear

Financial Considerations

  • Taxes Include: Sewer, Trash
  • Tax Amount: $61,627

Disclosures and Reports

  • Special Conditions: None
  • Property ID: 2801-000-546-00000-000-0056

Listed by Houlihan Lawrence Inc.

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agents

— 280 Highland Rd —

  • Houlihan Lawrence Inc.

  • Houlihan Lawrence Inc.

914-967-7680

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 280 Highland Rd

School District:Harrison Central School District
NameGradesDistance
Harrison Avenue Elementary School, Harrison, NY
480 Harrison Avenue, Harrison, NY 10528
K-51.7 mi
Louis M Klein Middle School
50 Union Avenue, Harrison, NY 10528
6-81.8 mi
Harrison High School, Harrison, NY
255 Union Avenue, Harrison, NY 10528
9-122.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 280 Highland Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/20/2026
Listed
$6,495,000
109.52%
MLS
10/15/2013
Sold
$3,100,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 280 Highland Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$19,457
100%
$36,150
-14%
2024
100%
$42,000
—
2020
-100%
$42,000
-18%
2020
$74,870
-3%
$51,000
—
2018
$77,051
15%
$51,000
1%
2017
$66,978
-4%
$50,500
—
2017
$69,823
-6%
$50,500
1%
2016
$74,104
-15%
$50,100
—
2015
$87,231
32%
$50,100
—
2014
$66,179
—
$50,100
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 280 Highland Rd

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Listed by Houlihan Lawrence Inc.

280 Highland Road, Rye, NY 10580 (MLS# 994413) is a Single Family property with 7 bedrooms, 6 full bathrooms and 1 partial bathroom. 280 Highland Road is currently listed for $6,495,000 and was received on May 20, 2026. Want to learn more about 280 Highland Road? Do you have questions about finding other Single Family real estate for sale in Rye? You can browse all Rye real estate or contact a Coldwell Banker agent to request more information.

Tour this property