Sold on oct 2026

$6,925,000

•

7,497

sq ft

280 Highland Rd, Rye, NY 10580

Track this home’s value and nearby sales activity

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

$924Price/Sq.Ft.

3 car garageParking

Listing by Donna McElwee • Houlihan Lawrence Inc.

Listing by Scott McElwee • Houlihan Lawrence Inc.

Contact: 914-967-7680

Bought with Michael McCooey • Compass Greater NY, LLC

Redfin checked: a minute ago

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

Redfin Estimate

$4,522,439

$2.4M since sold in October 2026$187K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.1% lower than the average sale price ($5.08M) of 5 comparable homes.

SOLD SEP 25, 2026
$5,850,000
A
5 beds6 baths7,505 sq ft
8 Boxwood Ln, Rye, NY 10580
Listing by Compass Greater NY, LLC
SOLD JUN 22, 2026
$4,250,000
B
6 beds7 baths6,719 sq ft
2 Park Dr S, Rye, NY 10580
Listing by Berkshire Hathaway HS NY Prop
SOLD SEP 23, 2026
$5,575,000
C
7 beds8.5 baths9,462 sq ft
25 Stratford Rd, Harrison, NY 10528
Listing by Julia B Fee Sothebys Int. Rlty
SOLD NOV 10, 2025
$7,200,000
D
6 beds7 baths8,585 sq ft
73 Park Dr S, Rye, NY 10580
Listing by Julia B Fee Sothebys Int. Rlty
SOLD SEP 21, 2026
$2,550,000
E
5 beds4.5 baths5,423 sq ft
3 Lakeside Dr, Rye, NY 10580
Listing by Julia B Fee Sothebys Int. Rlty

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Market trends in 10580, NY

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

107.7%

+1.2% MoM

Median sale price

$3.0M

$24K MoM

Avg. days on market

14d

1 days MoM

Recently sold homes

9 MoM

New listings for sale

$2,495,000
4 beds3.5 baths4,807 sq ft
8 Ironwood Ln, Rye, NY 10580
Listing by Houlihan Lawrence Inc.
$2,095,000
4 beds3 baths2,420 sq ft
29 Overlook Pl, Rye, NY 10580
Listing by Houlihan Lawrence Inc.
$355,000
1 bed1 bath800 sq ft
66 Milton Rd Unit D43, Rye, NY 10580
Listing by Compass Greater NY, LLC
$3,595,000
5 beds4.5 baths4,352 sq ft
65 Greenhaven Rd, Rye, NY 10580
Listing by Houlihan Lawrence Inc.
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Rental estimate

Est. $4,599 per month, based on comparable rentals

Sale and tax history for 280 Highland Rd

Sale History
Tax History

Date

Event

Price

OneKey® MLS as Distributed by MLS Grid #994413

Oct 22, 2026

Sold

$6,925,000

$924/sq ft

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,

OneKey® MLS as Distributed by MLS Grid #H3220112

Dec 6, 2012

Listing Removed

—

Jun 22, 2012

Listed

$3,995,000

$533/sq ft

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

—

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 Sep 25, 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

Property details

Parking

Parking Information
Carport YN: No
Parking Features: Detached, Driveway, Garage, Garage Door Opener

Garage Information
Garage Spaces: 3
Has Garage

Interior

Virtual Tour Information

Fireplace Information
Has Fireplace
Fireplaces Total: 6
Fireplace Features: Decorative, Gas, Wood Burning

Heating & Cooling
Cooling: Attic Fan, Central Air, Ductless, Zoned
Heating: Hydro Air, Natural Gas, Oil, Propane, Radiant

Interior Features
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
Window Features: Blinds, Oversized Windows
Laundry Features: Laundry Room
Appliances: Convection Oven, Dishwasher, Disposal, Dryer, Electric Oven, Exhaust Fan, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator
Flooring: Combination, Hardwood, Tile
Levels: Three Or More
Patio And Porch Features: Covered, Patio, Porch, Wrap Around

Room Information
Basement YN: Yes
Attic: Dormer,Partial
Rooms Total: 14
Basement: Unfinished

Bathroom Information
Bathrooms Full: 6
Bathrooms Half: 1

Exterior

Exterior Features
Exterior Features: Garden, Tennis Court(s)
Construction Materials: Shingle Siding
Other Structures: Garage(s), Outdoor Kitchen, Pool House
Security Features: Security System, Smoke Detector(s)
Waterfront YN: No

Pool Information
Has Private Pool
Pool Features: Fenced, In Ground, Pool Cover, Pool/Spa Combo
Has Spa

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

Property Information
Living Area Source: Appraiser
Living Area (Sq. Ft.): 7497.00
Building Area Total (Sq. Ft.): 8138.00
Building Area Source: Appraiser
Property Sub Type: Single Family Residence
Property Condition: Updated/Remodeled

Financial

Tax Information
Tax Year: 2025
Tax Source: Municipality
Tax Annual Amount: $61,627

Financial Information
Buyer Financing: Cash

Utilities

Utility Information
Electric Company: Con-Edison
Sewer: Public Sewer
Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Propane, Sewer Connected

Location

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

Location Information
Directions: Purchase St to 280 Highland Road , on right coming from downtown Rye, on left coming from Purchase St/ Biltmore Rd intersection
County Or Parish: Westchester County

Public facts

Beds: 4
Baths: 5.0
Sq. Ft.: 6,191
Stories: —
Lot Size: 2.42 acres
Style: Single Family Residential
Year Built: 1928
Year Renovated: —
County: Westchester County
APN: 552801A0005460000056

Home facts updated by county records on Sep 25, 2026

Around this home

Schools

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

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

Estimated sale price

$4.30M – $5.20M

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Home values near 280 Highland Rd

Data from public records.

Address	Redfin Estimate
260 Highland Rd, Rye, NY - Beds \| 4 Baths \| 4601 Sq. Ft.	$3,261,284
310 Highland Rd, Rye, NY 4 Beds \| 4 Baths \| 5141 Sq. Ft.	$3,196,237

Address	Redfin Estimate
235 Highland Rd, Rye, NY - Beds \| 3 Baths \| 2720 Sq. Ft.	$2,015,362
325 Highland Rd, Rye, NY 4 Beds \| 5 Baths \| 4687 Sq. Ft.	$4,219,855

Address	Redfin Estimate
322 Highland Rd, Rye, NY 5 Beds \| 4.5 Baths \| 4800 Sq. Ft.	$2,319,975
233 Highland Rd, Rye, NY 6 Beds \| 5.5 Baths \| 5725 Sq. Ft.	—

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2026. This data may not match . Learn more.

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About this home

Redfin Estimate

Market trends in 10580, NY

Homeowner tools

Sale and tax history for 280 Highland Rd

Public record

Property details

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 10580

Home values near 280 Highland Rd

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