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Sale Pending at 280 Highland Rd, Rye, NY 10580 | MLS# 994413 | Listing updated on 2026-06-11
Photo 1 of Sale Pending at 280 Highland Rd, Rye, NY 10580 | MLS# 994413 | Listing updated on 2026-06-11
Photo 2 of Sale Pending at 280 Highland Rd, Rye, NY 10580 | MLS# 994413 | Listing updated on 2026-06-11
Photo 3 of Sale Pending at 280 Highland Rd, Rye, NY 10580 | MLS# 994413 | Listing updated on 2026-06-11
Photo 4 of Sale Pending at 280 Highland Rd, Rye, NY 10580 | MLS# 994413 | Listing updated on 2026-06-11
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$6,495,000

Monthly Est:$32,328

  • Beds Icon7 Beds
  • Beds Icon
    7 Baths
  • Beds Icon7,497sqft

280 Highland Rd, Rye, NY 10580

$32,328/moEst:

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  • Single Family Residence

  • Built in 1928

  • $-- HOA

  • 2.41 acres lot

  • $866/sq.ft

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.

  • Houzeo last checked: 8 minutes ago
  • Listing updated: June 11, 2026 at 5:03 pm
  • Listing Provided by: Donna McElwee (914) 282-3274 , Scott McElwee | Houlihan Lawrence Inc. (914) 967-7680
  • Source: OneKey MLS-NY | MLS#: 994413 OneKey MLS-NY

Property Details

  • Status

    Pending

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Westchester County

  • City

    Rye

  • Neighborhood

    --

  • Year Built

    1928

  • HOA Fees

    -

  • Finished Area

    7,497 sqft

  • Lot Size

    2.41 acres lot

  • Basement Area

    - sqft

  • MLS Name

    OneKey MLS

  • MLS Number

    994413

  • MLS Status

    Pending

  • Days on Market

    158

  • Cumulative Days on Market

    8

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 7

    Bathrooms: 7

Interior

  • Heating

    Hydro Air, Natural Gas, Oil, Propane, Radiant, Radiant Floor

  • Exterior Features

    Garden, Tennis Court(s)

  • Appliances

    Convection Oven, Dishwasher, Disposal, Dryer, Electric Oven, Exhaust Fan, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator

  • Sewer

    Public Sewer

  • 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

  • Flooring

    Combination, Hardwood, Tile

  • Cooling

    Attic Fan, Central Air, Ductless, Zoned

Construction

  • Year Built

    Year Built: 1928

  • Home type

    Single Family Residence

  • Architectural Style

    Colonial

  • Property Condition

    Updated/remodeled

  • Construction Materials

    Shingle Siding

Utilities & Energy

  • Utilities

    Cable Connected, Electricity Connected, Natural Gas Connected, Propane, Sewer Connected

  • Parking Features

    Detached, Driveway, Garage, Garage Door Opener

  • Basement

    Unfinished

  • Pool Features

    Fenced, In Ground, Pool Cover, Pool/spa Combo

  • Security Features

    Security System, Smoke Detector(s)

  • Fireplace Features

    Decorative, Gas, Wood Burning

  • Water Source

    Private, Public

  • Laundry Features

    Laundry Room

Other Features

  • Lot Features

    Back Yard, Front Yard, Garden, Landscaped, Level, Near Golf Course, Near Public Transit, Near Shops, Private, Sprinklers In Front, Sprinklers In Rear

  • Patio And Porch Features

    Covered, Patio, Porch, Wrap Around

Price History

DateEventPrice

06/11/2026

Source: mls_logoOneKey MLS-NY #KEY994413

Pending

$6,495,000

$866/sqft

05/28/2026

Source: mls_logoOneKey MLS-NY #KEY994413

Listing Removed

$6,495,000

$866/sqft

05/20/2026

Source: mls_logoOneKey MLS-NY #KEY994413

Listed for Sale

$6,495,000

$866/sqft

05/15/2026

Source: mls_logoOneKey MLS-NY #KEY994413

Coming Soon

$6,495,000

$866/sqft

Nearby Homes

Based on information from OneKey MLS, through Oct 21, 2026, 11:16PM. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 OneKey® MLS. All rights reserved.

Advertising Broker: Derek Greene | The Greene Realty Group