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

$6,495,000

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

280 Highland Road, Rye, NY 10580

Est. Mortgage $43,003/mo*
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Home Highlights

Single-Family Home
Built in 1928
2.41 acre lot
$866/sqft
Garage

Local Information

  • Map ViewExplore the area around 280 Highland Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

"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.
Last check for updates: about 10 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: 101

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

Around this home

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
    Flag

Market trends in Rye

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.43M
$54.17KMoM
Sale-to-List Price
—
Price per sq ft
$774
$32MoM
Available listings
32
9MoM

Home Value

Trulia Estimate
$6.43M
Since last month
Decreased$4K (-0.1%)
Since last year
Increased$1M (+29.4%)
Since last sale
Increased$3M (+107.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +97% in the last 10 years
MonthEstimated value
2026
September 2026$6.42M
August 2026$6.43M
July 2026$6.41M
June 2026$6.47M
April 2026$5.25M
March 2026$5.31M
February 2026$5.21M
January 2026$5.44M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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
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
527 Purchase Street, Rye, NY
0.36
Single-Family Home
$2,050,000
06/03/26
4
4.5
3,895

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
7 Stonegate Lane, Rye, NY 10580
0.05
$3,485,300
4
5.5
6,069
Off Market
325 Highland Road, Rye, NY 10580
0.09
$4,261,400
4
5
4,687
Off Market
233 Highland Road, Rye, NY 10580
0.09
$3,295,000
6
5.5
5,725
For Sale
3 Highland Ridge Lane, Rye, NY 10580
0.11
$1,873,400
3
2.5
2,177
Off Market
5 Flagler Drive, Rye, NY 10580
0.16
$3,691,400
5
7.5
6,339
Off Market
450 Purchase Street, Rye, NY 10580
0.19
$2,829,500
5
4.5
5,541
Off Market
472 Purchase Street, Rye, NY 10580
0.21
$3,108,800
6
4.5
5,243
Off Market
4 Manhattan Avenue, Rye, NY 10580
0.20
$5,305,200
4
5
8,105
Off Market
1 Polly Pk Road, RYE, NY 10580
0.19
$3,393,900
5
5.5
5,789
Off Market
1 Manhattan Avenue, Rye, NY 10580
0.23
$4,093,100
4
4.5
4,084
Off Market
19 Hilltop Place, Rye, NY 10580
0.22
$11,584,500
9
10.5
11,236
Off Market
14 Highland Pk Place, Rye, NY 10580
0.24
$2,859,800
4
3.5
3,452
Off Market

Price and Tax history

DateEventPrice
Jun 11, 2026
Source: OneKey® MLS as distributed by MLS GRID #994413
Pending
$6,495,000
May 28, 2026
Source: OneKey® MLS as distributed by MLS GRID #994413
ListingRemoved
$6,495,000
May 20, 2026
Source: OneKey® MLS as distributed by MLS GRID #994413
Listed For Sale
$6,495,000
Oct 15, 2013
Source: OneKey® MLS as distributed by MLS GRID #H3234209
Sold
$3,100,000
Jul 7, 2013
Source: Agent Provided
ListingRemoved
$3,195,000

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 2026-09-20 08:18:18 PDT 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

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Frequently asked questions about 280 Highland Road

  • What is the estimated monthly payment for 280 Highland Road?
    Based on a $6,495,000 list price with 20% down at today's rates, the estimated monthly payment for 280 Highland Road in Rye, NY is approximately $43,516 (about $34,943 principal & interest, $8,498 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 280 Highland Road compare to homes in Rye?
    280 Highland Road in Rye, NY is listed at $6,495,000, about 167% above the $2.43M median sale price in Rye.
  • What do residents say about Rye?
    Residents describe Rye, NY as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See homes for sale in Rye, NY.
  • What are the closest schools to 280 Highland Road?
    The closest schools to 280 Highland Road in Rye, NY are Harrison Avenue Elementary School (rated 8/10), Harrison High School (rated 8/10), Louis M Klein Middle School (rated 9/10).
  • Does 280 Highland Road have air conditioning?
    Yes, 280 Highland Road in Rye, NY has air conditioning.
  • Does 280 Highland Road have a pool?
    Yes, 280 Highland Road in Rye, NY has a pool.
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.