280 Highland Road, Rye, NY 10580
PENDING
3D VIEW
2.41 ACRES

280 Highland Road
Rye, NY 10580

  • 7 Beds
  • 6.5 Baths
  • 7,497 sqft (on 2.41 acres)

$6,495,000

Est. Mortgage $40,195/mo*
Get Pre-Qualified

$6,495,000

Est. Mortgage $40,195/mo*
Get Pre-Qualified
7 Beds
6.5 Baths
7,497 sqft
(on 2.41 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

"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.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
$866
Listed
10 days ago
Last check for updates: about 17 hours ago
Listing by: Houlihan Lawrence Inc., (914) 967-7680
Donna McElwee, (914) 282-3274
Houlihan Lawrence Inc., (914) 967-7680
Scott McElwee, (914) 374-0715
Source: OneKey® MLS as distributed by MLS GRID, MLS#994413
Also Listed on OneKey® MLS as distributed by MLS GRID.

Home Details for 280 Highland Road

Interior Features

Interior Details
Basement: UnfinishedNumber of Rooms: 14Wet Bar
Beds & Baths
Number of Bedrooms: 7Number of Bathrooms: 7Number of Bathrooms (full): 6Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 7497 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Propane, Sewer ConnectedAppliances: Convection Oven, Dishwasher, Disposal, Dryer, Electric Oven, Exhaust Fan, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Wine RefrigeratorDishwasherDisposalDryerLaundry: Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Hydro Air,Natural Gas,Oil,Propane,Radiant,Radiant FloorHas CoolingAir Conditioning: Attic Fan,Central Air,Ductless,ZonedHas HeatingHeating Fuel: Hydro Air
Fireplace & Spa
Number of Fireplaces: 6Fireplace: Decorative, Gas, Wood BurningHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Blinds, Oversized WindowsFlooring: Combination, Hardwood, Tile
Levels, Entrance, & Accessibility
Levels: Three Or MoreFloors: Combination, Hardwood, Tile
Security
Security: Security System, Smoke Detector(s)

Exterior Features

Exterior Home Features
Patio / Porch: Covered, Patio, Porch, Wrap AroundOther Structures: Garage(s), Outdoor Kitchen, Pool HouseExterior: Garden, Tennis Court(s)GardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas Open ParkingParking Spaces: 3Parking: Detached,Driveway,Garage,Garage Door Opener
Pool
Pool: Fenced, In Ground, Pool Cover, Pool/Spa ComboPool
Water & Sewer
Sewer: Public Sewer
Farm & Range
Not Allowed to Raise Horses

Days on Market

Cumulative Days on Market: 8Days on Market: 10

Property Information

Year Built
Year Built: 1928Year Renovated: 2017
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial
Building
Construction Materials: Shingle SidingNot Attached Property
Property Information
Condition: Updated/RemodeledParcel Number: 2801000546000000000056

Price & Status

Price
List Price: $6,495,000Price Per Sqft: $866
Status Change & Dates
Off Market Date: Thu May 28 2026

Active Status

MLS Status: Pending

Media

Location

Direction & Address
City: Rye
School Information
Elementary School: Harrison Avenue Elementary SchoolJr High / Middle School: Louis M Klein Middle SchoolHigh School: Harrison High SchoolHigh School District: Harrison

Agent Information

Listing Agent
Listing ID: 994413

Building

Building Area
Building Area: 8138 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 2.41 Acres

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 994413Attic: Dormer, PartialAttribution Contact: 914-967-7680Showing AttendedShowing Requirements: Call Listing Agent, Occupied, Security System

Market trends in Rye

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
47
12MoM

Price History for 280 Highland Road

DatePriceEventSource
06/11/2026$6,495,000PendingOneKey® MLS as distributed by MLS GRID #994413
05/28/2026$6,495,000ListingRemovedOneKey® MLS as distributed by MLS GRID #994413
05/20/2026$6,495,000Listed For SaleOneKey® MLS as distributed by MLS GRID #994413
10/15/2013$3,100,000Sold
OneKey® MLS as distributed by MLS GRID #H3234209
07/07/2013$3,195,000ListingRemovedAgent Provided
05/18/2013$3,195,000PriceChange
Agent Provided
04/04/2013$3,395,000PriceChange
Agent Provided
03/26/2013$3,650,000PriceChange
Agent Provided
02/15/2013$3,850,000PriceChange
Agent Provided
11/02/2012$3,995,000PriceChange
Agent Provided
10/03/2012$4,200,000PriceChange
Agent Provided
08/03/2012$4,495,000PriceChange
Agent Provided
06/03/2011$4,995,000Listed For SaleAgent Provided
09/23/1998$2,500,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax
Assessment$36,150
Home facts updated by county records

Comparable Sales for 280 Highland Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
325 Highland Road, Rye, NY
0.09
Single-Family Home
$3,950,000
09/23/25
4
5
4,687
472 Purchase Street, Rye, NY
0.21
Single-Family Home
$2,856,651
07/17/25
6
4.5
5,243
1 Polly Pk Road, RYE, NY
0.19
Single-Family Home
$2,100,000
09/26/25
5
5.5
5,789
73 Park Drive S, Rye, NY
0.35
Single-Family Home
$7,200,000
11/10/25
6
7
8,585
14 Lakeside Drive, Rye, NY
0.36
Single-Family Home
$2,400,000
04/07/26
5
8
6,629
18 Lakeside Drive, Rye, NY
0.34
Single-Family Home
$3,450,000
05/29/26
5
4.5
4,612
19 Hilltop Place, Rye, NY
0.22
Single-Family Home
$10,750,000
10/03/25
9
10.5
11,236
17 Boxwood Lane, Rye, NY
0.72
Single-Family Home
$6,505,000
04/23/26
5
6
7,150

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 280 Highland Road.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Rye

At least 150 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there's holiday spirit

  • 81 % Say people would walk alone at night

  • 81 % Say kids play outside

  • 81 % Say yards are well-kept

  • 77 % Say car is needed

  • 77 % Say parking is easy

  • 72 % Say it's quiet

  • 71 % Say streets are well-lit

  • 69 % Say it's walkable to restaurants

  • 66 % Say there's wildlife

  • 64 % Say they plan to stay for at least 5 years

  • 62 % Say there are sidewalks

  • 57 % Say neighbors are friendly

  • 56 % Say there are community events

  • 44 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Zjstempel
    "There are a lot of good public parks and nice sidewalks to walk on. also a lot of people own their own dogs"
    0
    Flag
  • Dbenzanava
    "Dogs owners would like it very much. There are special Dog bakeries & pet shops catering to your pet. "
    0
    Flag
  • Brianrollins1959
    "When we walk our dog.There is always someone else walking their dog.Every one usually picks up after their dog "
    0
    Flag
  • Brianrollins1959
    "I get on 287 in the AM . It’s a 15 minute ride to White Plains. But when l come home at 12:30pm . Every body is stressed out. And driving on my bumper. I have to watch because they almost running into me "
    3
    Flag
  • Felix Vazquez Jr
    "They send helpful information in the mailbox which allows us to find events that are happening in the town"
    2
    Flag
  • Trulia User
    "Very kid friendly - just note it’s not the Rye school system. Nice walking area around the Neightborhood"
    1
    Flag
  • Patricia I.
    "Halloween window displays on Puchase street by the school children. Christmas street fair on Purchase st."
    1
    Flag
  • Nickalvarez4
    "7 minutes to metro north. Good parking at train station. Trains on schedule. 37 min train ride in to Grand Central."
    0
    Flag
  • Ltifdle
    "Right now my commute is down the staircase. Otherwise very convenient to all highways (i287, hutch, i95) and trains to city."
    0
    Flag
  • Ltifdle
    "Homes have large yards where it’s safe for children to play. Stores and restaurants are conveniently nearby. Easy access to major roadways and trains to city."
    0
    Flag
  • Cleary.aileen
    "I live here and it’s really a great place to live , lots of great things go on here and great community spirit "
    1
    Flag
  • Rosemary
    "Green community lots of parks great schools. Nice main avenue luxury shopping. Bistro restaurants. Some Catholic Church around. "
    0
    Flag
  • Heatherosemusic
    "Grew up here with my grandma and I love it. It’s the quintessential suburbs with proximity to Manhattan, a quaint village, great schools, a beach, an amusement park and so much more. The ideal neighborhood to raise a family. "
    6
    Flag
  • Manonbartels2008
    "Short and easy, fast commute. Plenty of trains, on time and easy access. Parking at station is hard due to permit wait list."
    1
    Flag
  • Fernando
    "I love Rye. It is a very quiet and peaceful neighborhood. the place is nice with good restaurants. "
    1
    Flag
  • Trulia User
    "Rye has Metro North station with direct access to city. Also there are 2 major highways with 4 exits in Rye."
    1
    Flag
  • Dan K.
    "Extremely safe and well kept place to live and be! Definitely a higher price point than even other parts of Westchester, but it is what it promotes itself to be. "
    1
    Flag
  • Ltifdle
    "Wonderful neighborhood to raise a family. Can walk to the club for all types of sports year-round. Many choices for great schools. Close to town, doctors, worship."
    0
    Flag
  • Michael C.
    "Extremely beautiful every season. Very quiet, family friendly to a fault. Winding roads assure privacy and security. "
    3
    Flag
  • Lriddle
    "My neighborhood is convenient to Westchester county, greenwich / Stamford by car and or nyc by train."
    0
    Flag
  • John J.
    "It’s a pretty dog friendly neighborhood. Town park with great dog community few blocks away. Few places in town have water bowls out front. I’m guessing every 3rd house has dog. "
    2
    Flag
  • Lriddle
    "Storybook Main Street with shops and restaurants. Very convenient commuting to work opportunities in Westchester, Connecticut and nyc."
    0
    Flag
  • Cchidiya
    "everything is convenient and easily accessible even by foot. it's a beautiful neighborhood. people are friendly, restaurants are organic, shopping is amazing. there is always free parking everywhere."
    0
    Flag
  • Contessa1313
    "Best of all possible areas for schools, trains, buses, walking, bicyling, water sports, gardening,etc."
    0
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LGBTQ Local Legal Protections

Donna McElwee, Houlihan Lawrence Inc., (914) 967-7680
Agent Phone: (914) 282-3274
Based on information submitted to the MLS GRID as of 2026-02-06 15:18:24 PST. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information
280 Highland Road, Rye, NY 10580 is a 7 bedroom, 7 bathroom, 7,497 sqft single-family home built in 1928. This property is currently available for sale and was listed by OneKey® MLS as distributed by MLS GRID on Jun 11, 2026. The MLS # for this home is MLS# 994413.