Pending

$6,495,000

Est. $40,514/mo —

•

7,497

sq ft

280 Highland Rd, Rye, NY 10580

About 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.

Single-familyProperty Type

1928Year Built

2.41 acresLot Size

$866Price/Sq.Ft.

3 car garageParking

Listing by Donna McElwee • Houlihan Lawrence Inc.

Listing by Scott McElwee • Houlihan Lawrence Inc.

Contact: 914-967-7680

Listing updated: Jun 11, 2026 at 01:03pm

Redfin checked: 3 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #994413

Payment calculator

$40,514 per month

Principal and interest$34,134

Property taxes

$5,136

HOA dues

Home insurance

$1,245

Utilities

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Open houses

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Around this home

Schools

K - 12
Preschool & daycare

Harrison Avenue Elementary School

Public K-5 • Assigned • 1.7mi

8/10

Louis M Klein Middle School

Public 6-8 • Assigned • 1.8mi

9/10

Harrison High School

Public 9-12 • Assigned • 2.6mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Market insights

280 Highland Rd · $6,495,000

DAYS ON MARKET

The average home goes pending in 19 days.

SALE-TO-LIST

Most homes are selling 8% above list price.

LIST PRICE

Median sale price in this area is $1,249,049. (81% lower than this home)

PRICE DROP

14% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Interior features
Breakfast bar
Built-in features
Chandelier
Chef's 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 closets
Wet bar
Oversized windows
Blinds
Covered, wrap-around porch and patio

Bedrooms
Bedrooms located on multiple levels (three or more levels)

Bathrooms
Six full bathrooms
One half bathroom

Kitchen
Convection oven
Gas cooktop
Electric oven
Microwave
Dishwasher
Disposal
Exhaust fan
Refrigerator
Stainless steel appliances
Wine refrigerator

Laundry & utility
Laundry room with washer and dryer

Flooring
Hardwood
Tile
Combination of flooring types

Heating & cooling
Central air
Ductless cooling
Zoned cooling
Attic fan
Hydro air heating
Natural gas heating
Oil heating
Propane heating
Radiant heating

Sale and tax history for 280 Highland Rd

Sale History
Tax History

Date

Event

Price

OneKey® MLS as Distributed by MLS Grid #994413

Jun 11, 2026

Pending

—

May 20, 2026

Listed

$6,495,000

$866/sq ft

May 15, 2026

Coming Soon

$6,495,000

$866/sq ft

HGMLS #3234209

Mar 14, 2014

Price Changed

$3,100,000

$413/sq ft

Oct 15, 2013

Sold

$3,100,000

$413/sq ft

Jul 6, 2013

Delisted

—

Jul 6, 2013

Price Changed

$3,195,000

$426/sq ft

May 17, 2013

Price Changed

$3,195,000

$426/sq ft

Apr 3, 2013

Price Changed

$3,395,000

$453/sq ft

Mar 25, 2013

Price Changed

$3,650,000

$487/sq ft

Feb 14, 2013

Price Changed

$3,850,000

$514/sq ft

Dec 17, 2012

Listed

$3,995,000

$533/sq ft

Once in a Lifetime opportunity to own the most admired home on Highland Road at a price to covet! Sited privately behind white picket fence and circular dwy, this estate personifies old world elegance with its high ceilings, magnificent moldings, thoughtful renovations throughout, covered and open terraces, pond, magnificent pool, re-surfaced all-weather tennis court, finished loft over garage, three floors of expansive & idyllic space. Just minutes from downtown Rye & walking distance to WCC.

OneKey® MLS as Distributed by MLS Grid #H3234209

Oct 15, 2013

Sold

$3,100,000

$413/sq ft

Dec 17, 2012

Listed

$3,195,000

$426/sq ft

Once in a Lifetime opportunity to own the most admired home on Highland Road at a price to covet! Sited privately behind white picket fence and circular dwy, this estate personifies old world elegance with its high ceilings, magnificent moldings, thoughtful renovations throughout, covered and open terraces,pond, magnificent pool, re-surfaced all-weather tennis court, finished loft over garage, three floors of expansive & idyllic space. Just minutes from downtown Rye & walking distance to WCC. Additional Information: Amenities:Tennis,ParkingFeatures:3 Car Detached,

HGMLS #3220112

Dec 6, 2012

Delisted

—

Nov 1, 2012

Price Changed

Oct 2, 2012

Price Changed

Aug 2, 2012

Price Changed

Jun 22, 2012

Listed

OneKey® MLS as Distributed by MLS Grid #H3220112

Dec 6, 2012

Listing Removed

—

Jun 22, 2012

Listed

$3,995,000

$533/sq ft

HGMLS #3117801

Jun 1, 2012

Delisted

—

Jun 2, 2011

Listed

HGMLS #2406827

Oct 7, 2004

Delisted

—

Apr 15, 2004

Listed

Public Records

Sep 23, 1998

Sold

$2,500,000

$333/sq ft

Public Records

Aug 19, 1993

Sold

$1,350,000

$180/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$62,958 (−0.7%)

$11,000 + $25,150

$36,150

2025

$63,381 (−14.8%)

$11,000 + $25,150

$36,150

2024

$74,428 (+10.9%)

$11,000 + $31,000

$42,000

2023

$67,133 (+2.5%)

$11,000 + $31,000

$42,000

2022

$65,474 (+2.1%)

$11,000 + $31,000

$42,000

2021

$64,112 (−14.4%)

$11,000 + $31,000

$42,000

2020

$74,871 (−5.4%)

$11,000 + $31,000

$42,000

2019

$79,180

$11,000 + $40,000

$51,000

2018

$11,000 + $40,000

$51,000

2017

$11,000 + $39,500

$50,500

2016

$11,000 + $39,500

$50,500

2014

$10,900 + $39,200

$50,100

2013

$10,900 + $39,200

$50,100

2012

$10,900 + $39,200

$50,100

2011

$10,900 + $39,200

$50,100

2010

$10,900 + $39,200

$50,100

2009

$10,900 + $39,200

$50,100

2008

$10,900 + $39,200

$50,100

Public record

Public record
Zoning

Beds

Baths

Stories

—

Lot width

—

Lot depth

—

Lot size

2.42 Acres

Year renovated

—

Finished Sq. Ft.

6,191

Unfinished Sq. Ft.

—

Total Sq. Ft.

6,191

Year built

1928

Style

Single Family Residential

County

Westchester County

APN

552801A0005460000056

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 30, 2026.

R-1

One-Family Residence District

Pursuant to Town Law 278, Subdivision 2, the Town of Harrison Planning Board shall have the authority, subject to the approval of the final plat by the Town Board, to permit or require residential cluster development in residential zoning districts R-1, and establish rules and regulations setting forth the conditions under which clustering may occur. The Planning Board shall request permission from the Town Board to consider clustering as soon in the process as the Planning Board determines that clustering would be beneficial to the town.; The Town Board shall promptly indicate to the Planning Board whether or not the Town Board will consider approval of a final plat that provides for clustering and any conditions the Town Board is then considering imposing.; The purpose of cluster development shall be to enable and encourage flexibility of design and development of land in such a manner that will result in: The preservation of open lands that are physically, aesthetically, scenically, historically and environmentally unique by virtue of their geology, topography, vegetative cover or previous use.; A pattern of development that preserves trees, outstanding natural topography and geologic features and prevents soil erosion.; The preservation or creation of open space, recreation areas and environmentally sensitive land areas.; An environment that is in harmony with surrounding development.; A choice in the types of environment and living units available to the public, so that development will be a permanent asset to the town.; An efficient use of land resulting in smaller networks of utilities and streets. A more desirable environment than would be possible through the strict application of other sections of law.

Permitted uses

Include but are not limited to:

Housing-Single unit
Public service
Library
Police station
Recreation
Park & open space

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 98° expected this year, 16 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

4/10 Air Factor

5 unhealthy days expected this year, 7 days in 30 years

Provided by First Street

Historical weather

Rye, NY • 10580

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

89/ 100

Very good sunlight

Sunscore

This home receives average direct sun exposure in Rye. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.4 hrs

6.5 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 280 Highland Rd

$6,581,204

$86K over list price of $6.50M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $2.2M to $6.5M.

SOLD APR 23, 2026
$6,505,000 Last sold price
5 beds6 baths7,150 sq ft
17 Boxwood Ln, Rye, NY 10580
Listing by Compass Greater NY, LLC
$44/sq ft
smaller lot
62 years newer
SOLD APR 7, 2026
$5,501,000 Last sold price
6 beds7.5 baths7,387 sq ft
32 Seville Ave, Rye, NY 10580
Listing by Julia B Fee Sothebys Int. Rlty
$121/sq ft
smaller lot
73 years newer
SOLD JUL 6, 2026
$3,200,000 Last sold price
6 beds5.5 baths3,902 sq ft
40 Mendota Ave, Rye, NY 10580
Listing by Houlihan Lawrence Inc.
$46/sq ft
smaller lot
12 years older
SOLD MAR 13, 2026
$2,200,000 Last sold price
6 beds3 baths3,171 sq ft
25 Seneca St, Rye, NY 10580
Listing by Houlihan Lawrence Inc.
$172/sq ft
smaller lot
28 years older
SOLD NOV 18, 2025
$3,234,160 Last sold price
5 beds5.5 baths5,752 sq ft
9 Boxwood Ln, Rye, NY 10580
Listing by Houlihan Lawrence Inc.
$304/sq ft
smaller lot
56 years newer
SOLD JUL 31, 2026
$3,325,000 Last sold price
5 beds4.5 baths5,887 sq ft
205 Polly Pk Rd, Rye, NY 10580
Listing by Julia B Fee Sothebys Int. Rlty
$301/sq ft
smaller lot
59 years newer

Rental earnings

Est. $4,852 per month, based on comparable rentals

This home is pending

The seller has accepted an offer, and this property is now .

Have questions?

Ken Wile

Redfin Licensed Associate Real Estate Broker

Ken Wile typically replies in about 16 minutes

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Details provided by OneKey® MLS as Distributed by MLS Grid and may not match the public record. Learn more.

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