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Sold for $6,925,000
    • $6,925,000

    280 Highland Road, Rye, NY 10580

    7beds
    7,497sqft
    Single Family Residence, Residential
    Built in 1928
    2.41 Acres Lot
    $6,928,600 Zestimate®
    $924/sqft
    $-- Estimated rent

    Home value

    $6,928,600

    $6.31M - $7.62M

    Not available

    Zestimate® history

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    $49,277/mo

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    What's special

    "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.

    Zillow last checked:

    Listing updated:

    Listed by:

    Donna McElwee 914-282-3274,

    Houlihan Lawrence Inc. 914-967-7680,

    Scott McElwee 914-374-0715,

    Houlihan Lawrence Inc.

    Bought with:

    Michael P. McCooey, 10401255696

    Compass Greater NY, LLC

    Source: OneKey® MLS as distributed by MLS GRID,MLS#: 994413MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 7
    • Bathrooms: 7
    • Full bathrooms: 6
    • 1/2 bathrooms: 1
    Other
    • Description: 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...
    • Level: First
    Other
    • 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.
    • Level: First
    Other
    • 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
    • Level: Second
    Other
    • 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
    • Level: Third
    Other
    • 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
    • Level: Other
    Heating
    • Hydro Air, Natural Gas, Oil, Propane, Radiant, Radiant Floor
    Cooling
    • Attic Fan, Central Air, Ductless, Zoned
    Appliances
    • Included: Convection Oven, Dishwasher, Disposal, Dryer, Electric Oven, Exhaust Fan, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator
    • Laundry: Laundry Room
    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
    • Flooring: Combination, Hardwood, Tile
    • Windows: Blinds, Oversized Windows
    • Basement: Unfinished
    • Attic: Dormer,Partial
    • Number of fireplaces: 6
    • Fireplace features: Decorative, Gas, Wood Burning
    Interior area
    • Total structure area: 8,138
    • Total interior livable area: 7,497 sqft

    Property

    Parking
    • Total spaces: 3
    • Parking features: Detached, Driveway, Garage, Garage Door Opener
    • Garage spaces: 3
    • Has uncovered spaces: Yes
    Features
    • Levels: Three Or More
    • Patio & porch: Covered, Patio, Porch, Wrap Around
    • Exterior features: Garden, Tennis Court(s)
    • Has private pool: Yes
    • Pool features: Fenced, In Ground, Pool Cover, Pool/Spa Combo
    • Has spa: Yes
    Lot
    • Size: 2.41 Acres
    • Features: Back Yard, Front Yard, Garden, Landscaped, Level, Near Golf Course, Near Public Transit, Near Shops, Private, Sprinklers In Front, Sprinklers In Rear
    Details
    • Additional structures: Garage(s), Outdoor Kitchen, Pool House
    • Parcel number: 2801000546000000000056
    • Special conditions: None

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Colonial
    • Property subtype: Single Family Residence, Residential
    Materials
    • Shingle Siding
    Condition
    • Updated/Remodeled
    • Year built: 1928
    • Major remodel year: 2017

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: Private, Public
    • Utilities for property: Cable Connected, Electricity Connected, Natural Gas Connected, Propane, Sewer Connected

    Community & HOA

    Community
    • Security: Security System, Smoke Detector(s)
    HOA
    • Has HOA: No
    Location
    • Region: Rye

    Financial & listing details

    • Price per square foot: $924/sqft
    • Tax assessed value: $36,150
    • Annual tax amount: $61,627
    • Date on market: 5/20/2026
    • Cumulative days on market: 8 days
    • Listing agreement: Exclusive Right To Sell
    • Electric utility on property: Yes

    Price history

    DateEventPrice
    10/22/2026Sold$6,925,000+6.6%$924/sqft
    Source: OneKey® MLS as distributed by MLS GRID #994413 Report a problem
    6/11/2026Pending sale$6,495,000$866/sqft
    Source: OneKey® MLS as distributed by MLS GRID #994413 Report a problem
    5/28/2026Listing removed$6,495,000$866/sqft
    Source: OneKey® MLS as distributed by MLS GRID #994413 Report a problem
    5/20/2026Listed for sale$6,495,000+109.5%$866/sqft
    Source: OneKey® MLS as distributed by MLS GRID #994413 Report a problem
    10/15/2013Sold$3,100,000-3%$413/sqft
    Source: OneKey® MLS as distributed by MLS GRID #H3234209 Report a problem
    7/7/2013Listing removed$3,195,000$426/sqft
    Source: Coldwell Banker Residential Brokerage - Rye/Harrison Office #3234209 Report a problem
    5/18/2013Price change$3,195,000-5.9%$426/sqft
    Source: Coldwell Banker Residential Brokerage - Rye/Harrison Office #3234209 Report a problem
    4/4/2013Price change$3,395,000-7%$453/sqft
    Source: Coldwell Banker Residential Brokerage - Rye/Harrison Office #3234209 Report a problem
    3/26/2013Price change$3,650,000-5.2%$487/sqft
    Source: Coldwell Banker Residential Brokerage - Rye/Harrison Office #3234209 Report a problem
    2/15/2013Price change$3,850,000-3.6%$514/sqft
    Source: Coldwell Banker Residential Brokerage - Rye/Harrison Office #3234209 Report a problem
    11/2/2012Price change$3,995,000-4.9%$533/sqft
    Source: Coldwell Banker Residential Brokerage - Rye/Harrison Office #3220112 Report a problem
    10/3/2012Price change$4,200,000-6.6%$560/sqft
    Source: Coldwell Banker Residential Brokerage - Rye/Harrison Office #3220112 Report a problem
    8/3/2012Listed for sale$4,495,000-10%$600/sqft
    Source: Coldwell Banker Residential Brokerage - Rye/Harrison Office #3220112 Report a problem
    6/3/2011Listed for sale$4,995,000+99.8%$666/sqft
    Source: Coldwell Banker Residential Brokerage - Rye/Harrison Office #3117801 Report a problem
    9/23/1998Sold$2,500,000$333/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025-- $36,150 -13.9%
    2024-- $42,000
    2023-- $42,000
    2022-- $42,000
    2021-- $42,000
    2020-- $42,000 -17.6%
    2019-- $51,000
    2018-- $51,000 +1%
    2017-- $50,500
    2016-- $50,500 +0.8%
    2015-- $50,100
    2014-- $50,100
    2013-- $50,100
    2012-- $50,100
    2011-- $50,100
    2010-- $50,100
    2009-- $50,100
    2008-- $50,100
    2007-- $50,100
    2006-- $50,100
    2004-- $50,100
    2003-- $50,100
    2002-- $50,100 +0.8%
    2001-- $49,700 +6%
    2000-- $46,900
    1999-- $46,900
    Find assessor info on the county website

    Neighborhood: 10580

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Harrison Avenue Elementary School - Harrison
    • Middle: Louis M Klein Middle School
    • High: Harrison High School

    Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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    Estimated market value

    $6,928,600

    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value

    $6,928,600

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