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Under contract-show
  • Price cut: $655K (7/16)
    $2,995,000

    365 Sherwood Dr S, Flat Rock, NC 28731

    5beds
    8,300sqft
    : 
    $18,151/mo
    Get pre-qualified
    Single Family Residence
    Built in 1938
    5.83 Acres Lot
    $-- Zestimate®
    $361/sqft
    $217/mo HOA

    What's special

    High ceilingsWood-burning fireplacesTwo charming guest cottagesTwo porchesPlaster wallsPrivate courtyardsGarden pavilion
    In the storied heart of Flat Rock lies Hopewood, an extraordinary estate that blends timeless elegance with welcoming warmth. Set on nearly six acres of formal gardens, private courtyards and tranquil retreats, this rare property is a Southern treasure. Originally commissioned in 1938 by Reuben B. and Hope Thomson Robertson, the residence was designed by their nephew, James Gamble Rogers II, a distinguished architect trained at the École des Beaux-Arts in Paris. The Robertson family’s legacy is deeply entwined with the history of Champion Paper, the Great Smoky Mountains National Park and Asheville itself, giving Hopewood a provenance as rich as its beauty. Approached beneath a canopy of trees, the main home opens through the original solid cherrywood door into a grand foyer, where a sweeping staircase and quarter-sawn oak floors laid in elegant patterns set the tone. Gracious living and dining rooms, each with wood-burning fireplaces, showcase high ceilings, plaster walls and fine wainscoting, while the loggia, with its terrazzo floors, leads to a Japanese-inspired stone-walled garden. A temperature-controlled wine room, handsome library with fireplace, and bright en-suite guest room complete the main level. At the heart of the home, the thoughtfully updated kitchen features a Sub-Zero refrigerator, Wolf six-burner range, expansive island and adjoining casual dining space that flows naturally to the outdoor terraces. An entertainment pantry with a secondary dishwasher and beverage cooler elevates gatherings, while a hidden elevator connects all levels with ease. Upstairs, a spacious library, two porches and two additional en-suite bedrooms offer refined comfort. The primary suite impresses with vaulted ceilings, dual dressing rooms, a spa-like bath and a morning bar. Original details, from preserved moldings to artisan light fixtures, are complemented by sensitive updates that respect the home’s history while enhancing livability. The estate’s grounds are equally captivating. Formal boxwood gardens, cutting beds and a heritage Japanese maple (imported in the 1890s) create a horticultural tapestry of rare beauty. Meandering paths lead to a stone fire pit, a garden pavilion and tranquil lawns designed for outdoor entertaining. Two charming guest cottages, one with two bedrooms and two baths, the other with two bedrooms, a full bath and half bath, add versatility for hosting, caretakers or extended family. In total, the property encompasses seven bedrooms, six full baths and two half baths. Hopewood is more than an estate, it is a living legacy. Lovingly stewarded through generations and protected by preservation easement, it embodies the enduring spirit of Flat Rock, where history, nature and refinement meet in one of the South’s cherished settings. Seller offering finance options.
    144 days
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    372
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    17
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    Zillow last checked:

    Listing updated:

    Listed by:

    Marilyn Wright 828-279-3980,

    Premier Sotheby’s International Realty

    Source: Canopy MLS as distributed by MLS GRID,MLS#: 4353114MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 6
      • Full bathrooms: 5
      • 1/2 bathrooms: 1
      • Main level bedrooms: 1
      Primary bedroom
      • Level: Upper
      Bedroom s
      • Level: Main
      Bedroom s
      • Level: Upper
      Bathroom half
      • Level: Main
      Bathroom full
      • Level: Main
      Bathroom full
      • Level: Upper
      Bathroom full
      • Level: Upper
      Bar entertainment
      • Level: Upper
      Dining room
      • Level: Main
      Kitchen
      • Level: Main
      Laundry
      • Level: Upper
      Library
      • Level: Upper
      Living room
      • Level: Main
      Other
      • Level: Main
      Other
      • Level: Main
      Other
      • Level: Main
      Heating
      • Heat Pump, Natural Gas
      Cooling
      • Zoned
      Appliances
      • Included: Bar Fridge, Dishwasher, Double Oven, Dryer, Electric Water Heater, Gas Cooktop, Gas Oven, Gas Range, Microwave, Oven, Refrigerator with Ice Maker, Tankless Water Heater, Washer, Washer/Dryer, Wine Refrigerator
      • Laundry: In Basement, Multiple Locations
      Features
      • Built-in Features, Elevator, Kitchen Island, Pantry, Storage, Walk-In Closet(s), Walk-In Pantry, Wet Bar, Total Primary Heated Living Area: 7031
      • Flooring: Stone, Wood
      • Doors: French Doors
      • Windows: Insulated Windows
      • Basement: Exterior Entry,Unfinished,Walk-Out Access
      • Attic: Pull Down Stairs
      • Fireplace features: Family Room, Gas Log, Living Room, Primary Bedroom
      Interior area
      • Total structure area: 7,031
      • Total interior livable area: 8,300 sqft
      • Finished area above ground: 7,031
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 2
      • Parking features: Driveway, Attached Garage, Detached Garage
      • Attached garage spaces: 2
      • Has uncovered spaces: Yes
      • Details: Attached 2 car garage, detached 2 car garage, 2 car carport at South Cottage
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Patio, Porch, Rear Porch, Side Porch
      • Exterior features: Fire Pit
      Lot
      • Size: 5.83 Acres
      • Features: Cleared, Green Area, Level, Pasture, Wooded
      Living quarters
      • Secondary living space: 1269 sqft
      • Secondary features: Guest House
      Details
      • Additional structures: Shed(s)
      • Parcel number: 9971995
      • Zoning: R-40
      • Special conditions: Standard
      • Other equipment: Generator

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Traditional
      • Property subtype: Single Family Residence
      Materials
      • Brick Full
      • Roof: Metal
      Condition
      • New construction: No
      • Year built: 1938

      Utilities & green energy

      • Sewer: Septic Installed
      • Water: City

      Community & HOA

      Community
      • Security: Carbon Monoxide Detector(s), Security System
      • Subdivision: Sherwood
      HOA
      • Has HOA: Yes
      • HOA fee: $2,600 annually
      • HOA name: Cedar Management Group
      • HOA phone: 877-252-3327
      Location
      • Region: Flat Rock

      Financial & listing details

      • Price per square foot: $361/sqft
      • Tax assessed value: $2,228,300
      • Annual tax amount: $9,604
      • Date on market: 3/31/2026
      • Cumulative days on market: 145 days
      • Listing terms: Cash,Conventional
      • Road surface type: Gravel, Paved

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/16/2026Price change$2,995,000-17.9%$361/sqft
        Source: Canopy MLS as distributed by MLS GRID #4353114 Report a problem
        5/13/2026Price change$3,650,000-7.6%$440/sqft
        Source: Canopy MLS as distributed by MLS GRID #4353114 Report a problem
        3/31/2026Listed for sale$3,950,000-12.2%$476/sqft
        Source: Canopy MLS as distributed by MLS GRID #4353114 Report a problem
        2/12/2026Listing removed$4,500,000$542/sqft
        Source: Canopy MLS as distributed by MLS GRID #4235588 Report a problem
        7/28/2025Price change$4,500,000-24.9%$542/sqft
        Source: Canopy MLS as distributed by MLS GRID #4235588 Report a problem
        4/8/2025Listed for sale$5,995,000+531.1%$722/sqft
        Source: Canopy MLS as distributed by MLS GRID #4235588 Report a problem
        11/16/2009Sold$950,000$114/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$9,604 $2,228,300
        2024$9,604 $2,228,300
        2023$9,604 +5%$2,228,300 +36.7%
        2022$9,145 $1,630,200
        2021-- $1,630,200
        2020$9,145 $1,630,200
        2019$9,145 $1,630,200 +11.2%
        2018$9,145 +10.4%$1,465,800
        2017$8,282 $1,465,800
        2016-- $1,465,800
        2015-- $1,465,800 +3.8%
        2014-- $1,412,800
        2013-- $1,412,800
        2012-- $1,412,800 +1.8%
        2011-- $1,388,400 +40.8%
        2010-- $986,000 -19%
        2008-- $1,216,700
        2007-- $1,216,700 +25.5%
        2006-- $969,100
        2005-- $969,100
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 28731

        Getting around

        7 / 100
        Car-Dependent
        19 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Hillandale
        • Middle: Flat Rock
        • High: East

        Source: Canopy 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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