Pending
Pending
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..."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.
- Listed by Donna McElwee • Houlihan Lawrence Inc.P: (914)-967-7680 C: (914)-282-3274 dmcelwee@houlihanlawrence.com
- Listed by Scott McElwee • Houlihan Lawrence Inc.P: (914)-967-7680 C: (914)-374-0715 smcelwee@houlihanlawrence.com
Property Details for 280 Highland Road
City/Township
Harrison
Architectural StyleColonial
Garage Spaces3.00
WaterfrontNo
Section AreaHilltop Place
LISTING UPDATED: 06/11/2026 01:03 PM
Property Details for 280 Highland Road
| Status | Pending |
|---|---|
| MLS # | 994413 |
| Days on Market | 8 |
| Taxes | $61,627 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Property Type | Single Family |
| MLS Type | Single Family |
| Year Built | 1928 |
| Lot Size | 2.41 AC / 104,980 SF |
| County | Westchester County |
Location
Listing Courtesy of Houlihan Lawrence Inc.
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Building Information for 280 Highland Road
Stories-Year Built1928Building Size-Lot Size2.41 AC / 104,980 SF
Payment Calculator
$37,501 per month
30 year fixed, 6.36% Interest
Principal and Interest
$32,365
Property Taxes
$5,136
HOA Dues
$0
The Payment Calculator is for illustrative purposes only.
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1Property Information for 280 Highland Road
Summary
Location and General Information
- Senior Community YN: No
- Directions: Purchase St to 280 Highland Road , on right coming from downtown Rye, on left coming from Purchase St/ Biltmore Rd intersection
- Year Built Effective: 2017
- Property Attached: No
- Structure Type: Detached
- Levels: Three Or More
- Property Condition: Updated/Remodeled
- State Or Province: NY
- Water Access YN: No
School Information
- School District: Harrison
- Elementary School District: Harrison
- Elementary School: Harrison Avenue Elementary School
- Middle Or Junior School District: Harrison
- Middle Or Junior School: Louis M Klein Middle School
- High School District: Harrison
- High School: Harrison High School
Rental
Rental
- Lease Considered: No
Unit Information
Unit Information
- Building Units Total: 1
Room Information
Room 1 Information
- Room Level: First
- RoomDescription 1: MAIN HOUSE FIRST FLOOR: Dramatic Front Entrance Foyer graciously creates natural flow throughout the first floor opening to an Entertainment Sized Living Room with multiple seating areas gas fireplace/Showstopping wet bar/ Formal Dining Area easily seats 10+ with a beautiful backdrop of three large 12 over 12 windows with amazing views, French Dr Entry with privacy glass from Foyer to stunning Library with cherry wood windows and trim/ handsome built-in bookshelves flanking the wood burning fireplace with easy access to renovated Formal Powder Rm/ Stroll through the deep Front Foyer to enter the generous Family Room with wood-burning fireplace with double entrances to the stunning renovated Chef's Kitchen featuring high end stainless appliances/Quartz countertops & Waterfall Island with seating for 4 / Walk-in Pantry/Back Kitchen work space/ Coffee and juice Bar, plus Dining Area seating 8+ overlooking the breathtaking private backyard and pool area...
Room 2 Information
- Room Level: First
- Room Description: MAIN HOUSE First Floor continued .... Entrance to the huge Mudroom with 5 cubbies/shelves, 2 built -in work stations with adjacent Laundry Room conveniently tucked behind the front staircase with side entrance and covered porch offering high functionality for day to day living. This floor plan offers the perfect blend of living space to enjoy a Formal lifestyle of a carefully curated home, while having wonderful casual living space for day to day activities.
Room 3 Information
- Room Level: Second
- Room Description: MAIN HOUSE SECOND FLOOR: Private sun-filled Primary Suite with fireplace/ Luxurious Primary Bath ensuite with large stall shower/ claw foot tub/ large double vanity sink/ separate WC/ Dual walk- in closets, Steps up to large Hall, Bedroom/Renovated Bath/ Bedroom, Bedroom/ Recently Renovated Ensuite Bath, Bedroom/ Home Office
Room 4 Information
- Room Level: Third
- Room Description: MAIN HOUSE THIRD FLOOR: Oversized Bedroom with separate Sitting Area/ Renovated Bath/ Walk-in Closet, Bedroom, Renovated Hall Bath, Playroom, Large Cedar Closet, Attic Utility Closet
Room 5 Information
- Room Level: Other
- Room Description: POOL HOUSE: Open floor plan with Vaulted Ceiling : Kitchen Area with large quartz peninsula with bar stool seating for 4/ Generous sitting area/ Plenty of Room for Game Table, Full Bath, Storage Closets
Taxes and HOA Information
Taxes and HOA Information
- Parcel Number: 2801-000-546-00000-000-0056
- Tax Assessed Value: $36,150.00
- Included In Taxes: Sewer, Trash
- Tax Source: Municipality
- Tax Year: 2025.0
- Association: No
Interior and Exterior Features
Interior Features
- Amenities: Blinds, Breakfast Bar, Built-in Features, Chandelier, Chefs Kitchen, Colonial, Combination, Covered, Crown Molding, Decorative, Double Vanity, Eat in Kitchen, Entrance Foyer, Fenced, Garage(s), Garden, Gas, Hardwood Floors As Seen, High Ceilings, His and Hers Closets, In Ground, Kitchen Island, Laundry Room, Outdoor Kitchen, Oversized Windows, Pantry, Patio, Pool Cover, Pool House, Pool/Spa Combo, Porch, Primary Bathroom, Privacy, Public, Quartz/Quartzite Counters, Recessed Lighting, Security System, Smoke Detector(s), Soaking Tub, Storage, Tennis Court(s), Tile, Walk In Closet, Wet Bar, Wood Burning, Wrap Around
- 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
- Appliances: Convection Oven, Dishwasher, Disposal, Dryer, Electric Oven, Exhaust Fan, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator
- Number Of Kitchens: 1.0
- Total Rooms: 14
- Basement: Unfinished
- Attic Description: Dormer,Partial
- Fireplace: Yes
- Fireplaces Total: 6
- Fireplace Features: Decorative, Gas, Wood Burning
- Location Amenities: Stainless Steel Appliances, Tennis, Hardwood Floors As Seen, Chef's Kitchen, Dual Sinks, Eat in Kitchen, Entry Foyer, Foyer, High Ceilings, Island Kitchen, Pantry, Soacking Tub, Storage, Walk In Closet, Wetbar, Garden, Privacy, Patio, Porch, In Ground Pool, Security System, Oversized Windows
- Laundry Features: Laundry Room
- Security Features: Security System, Smoke Detector(s)
- Spa: Yes
- Window Features: Blinds, Oversized Windows
- Flooring: Combination, Hardwood, Tile
- Living Area: 7,497.00
- Basement: Yes
Exterior Features
- Exterior Features: Garden, Tennis Court(s)
- Exterior Property Features: Garden, Tennis Court(s), Fenced, In Ground, Pool Cover, Pool/Spa Combo, Covered, Patio, Porch, Wrap Around, Detached, Driveway, Garage, Garage Door Opener, Blinds, Oversized Windows, Back Yard, Front Yard, Landscaped, Level, Near Golf Course, Near Public Transit, Near Shops, Private, Sprinklers In Front, Sprinklers In Rear
- Elevation Certificate: No
- Patio And Porch Features: Covered, Patio, Porch, Wrap Around
- Construction Materials: Shingle Siding
- Other Structures: Garage(s), Outdoor Kitchen, Pool House
- Horse: No
- Pool Private: Yes
- Pool Features: Fenced, In Ground, Pool Cover, Pool/Spa Combo
- Pool Details: Fenced,In Ground,Pool Cover,Pool/Spa Combo
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
- Site Features: Back Yard, Front Yard, Garden, Landscaped, Level, Near Golf Course, Near Public Transit, Near Shops, Private, Sprinklers In Front, Sprinklers In Rear
- Building Area Units: Square Feet
Parking
- Parking Features: Detached, Driveway, Garage, Garage Door Opener
- Garage: Yes
- Carport: No
Utilities
- Cooling: Attic Fan, Central Air, Ductless, Zoned
- Heating: Hydro Air, Natural Gas, Oil, Propane, Radiant, Radiant Floor
- Heat Fuel Type: Hydro Air, Natural Gas, Oil, Propane, Radiant, Radiant Floor
- Number Of Heating Zones: 6
- Sewer: Public Sewer
- Water Source: Private, Public
- Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Propane, Sewer Connected
Green Features
- Green Features: Blinds, Oversized Windows, Convection Oven, Dishwasher, Disposal, Dryer, Electric Oven, Exhaust Fan, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator, Hydro Air, Natural Gas, Oil, Propane, Radiant, Radiant Floor, Garden, Tennis Court(s), Fenced, In Ground, Pool Cover, Pool/Spa Combo
Virtual Tour
- Virtual Tour URL Unbranded: https://www.wellcomemat.com/mls/fnf37e05a51mkt3
Agent
Payment and Rate
- Down Payment Resource: No
Property History for 280 Highland Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Jun 11, 2026 | Pending ONEKEY #994413 | — | |
| May 28, 2026 | Temporarily Off Market ONEKEY #994413 | $6,495,000 | — |
| May 20, 2026 | Listed (Active) ONEKEY #994413 | $6,495,000 | — |
| Oct 15, 2013 | Sold (Public Record) Public Record #410407844 | $3,100,000 | — |
| Oct 15, 2013 | Sold (Public Record) Public Record #410407844 | $3,100,000 | — |
| Oct 15, 2013 | Sold ONEKEY #H3234209 | $3,100,000 | — |
| Oct 15, 2013 | Sold HGMLS #3234209 | $3,100,000 | — |
| Jul 6, 2013 | Pending ONEKEY #H3234209 | — | |
| Jul 6, 2013 | Contract HGMLS #3234209 | — | |
| Mar 22, 2013 | Expired ONEKEY #H3220112 | $3,995,000 | — |
| Dec 17, 2012 | Listed (Active) HGMLS #3234209 | $3,995,000 | — |
| Dec 17, 2012 | Listed (Active) ONEKEY #H3234209 | $3,995,000 | — |
| Jun 22, 2012 | Listed (Active) ONEKEY #H3220112 | $4,995,000 | — |
| Jun 22, 2012 | Listed (Active) HGMLS #3220112 | $4,995,000 | — |
| Jun 2, 2011 | Listed (Active) HGMLS #3117801 | $4,995,000 | — |
| Apr 15, 2004 | Listed (Active) HGMLS #2406827 | $4,950,000 | — |
| Sep 16, 1998 | Sold HGMLS #9803982 | $2,500,000 | — |
| Feb 27, 1998 | Listed (Active) HGMLS #9803982 | $2,700,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 06/11/2026 | Pending ONEKEY #994413 | — |
| 05/28/2026 | Temporarily Off Market ONEKEY #994413 | $6,495,000 |
| 05/20/2026 | Listed (Active) ONEKEY #994413 | $6,495,000 |
| 10/15/2013 | Sold (Public Record) Public Record #410407844 | $3,100,000 |
| 10/15/2013 | Sold (Public Record) Public Record #410407844 | $3,100,000 |
| 10/15/2013 | Sold ONEKEY #H3234209 | $3,100,000 |
| 10/15/2013 | Sold HGMLS #3234209 | $3,100,000 |
| 07/06/2013 | Pending ONEKEY #H3234209 | — |
| 07/06/2013 | Contract HGMLS #3234209 | — |
| 03/22/2013 | Expired ONEKEY #H3220112 | $3,995,000 |
| 12/17/2012 | Listed (Active) HGMLS #3234209 | $3,995,000 |
| 12/17/2012 | Listed (Active) ONEKEY #H3234209 | $3,995,000 |
| 06/22/2012 | Listed (Active) ONEKEY #H3220112 | $4,995,000 |
| 06/22/2012 | Listed (Active) HGMLS #3220112 | $4,995,000 |
| 06/02/2011 | Listed (Active) HGMLS #3117801 | $4,995,000 |
| 04/15/2004 | Listed (Active) HGMLS #2406827 | $4,950,000 |
| 09/16/1998 | Sold HGMLS #9803982 | $2,500,000 |
| 02/27/1998 | Listed (Active) HGMLS #9803982 | $2,700,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 280 Highland Road
Taxable ValueLand$11,000Additions$25,150Total$36,150
Tax Record2025$19,457 ($1,621 / month)
Home Facts
Beds4Total Finished SqFt6,191 SqFtAbove Grade Finished SqFt6,191 SqFtStories2Lot Size104,980 SqFtStyleSingle Family ResidenceYear Built1928ZoningR-1CountyWESTCHESTERAPN552801 0546.-56Fireplace TypeHas Fireplace
Schools near 280 Highland Road
This home is within Harrison Central School District.
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | K to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 | |||
| Private - | PK to 12 |
Rating | School | Distance |
|---|---|---|
Harrison Avenue Elementary School PublicK to 5 | ||
Louis M Klein Middle School Public6 to 8 | ||
Harrison High School Public9 to 12 | ||
Rye Country Day School PrivatePK to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.
Listing Courtesy of Houlihan Lawrence Inc.
Based on information submitted to the MLS GRID as of 06/11/2026 01:03 PM. 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. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.
