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Pending
$2,995,000 Est. $20,853/mo — Get pre-qualified
5beds 5.5baths 8,300sq ft 5.83acres

365 Sherwood Drive S · Flat Rock, NC 28731

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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.

Features & Amenities

Living Area8,300 Sq.Ft.
Bedrooms5
Baths5.5
HeatingHeat Pump, Natural Gas
CoolingZoned
FlooringStone, Wood
FireplaceFamily Room,Gas Log,Living Room,Primary Bedroom
AppliancesBar 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
Interior FeaturesAttic Stairs Pulldown, Built-in Features, Elevator, Entrance Foyer, Kitchen Island, Pantry, Storage, Walk-In Closet(s), Walk-In Pantry, Wet Bar
LaundryIn Basement, Multiple Locations
Virtual TourOpen Virtual Tour
Exterior FeaturesFire Pit
StyleTraditional
Year Built1938
ConstructionBrick Full
RoofMetal
FoundationBasement
ParkingDriveway, Attached Garage, Detached Garage
StatusPending
Lot Size5.83 Acres
Lot FeaturesCleared, Green Area, Level, Pasture, Wooded
SubdivisionSherwood
CountyHENDERSON
Property TypeResidential
Property SubTypeSingle Family Residence
Last UpdatedOct 9, 2026
SewerSeptic Installed
Water SourceCity
HOAYes — $2,600 / year
HOA ManagementCedar Management Group
ElementaryHillandale Elementary School
MiddleFlat Rock Middle School
HighEast High School
Presented By: Premier Sotheby’s International Realty; beatrix.masotti@premiersir.com

Location

Property boundary from county GIS

Neighborhood Snapshot

U.S. Census Bureau, ACS 5-year estimates

Neighborhood data describes this home's U.S. Census tract and is provided for information only. Statistics describe an area, not any individual property or its residents.

Pricing History

DateEventPriceChange
Oct 9, 2026 Price Reduced $3,650,000 → $2,995,000 ▾ $655,000 (17.9%)
Mar 31, 2026 Price Change $3,950,000 —

Monthly Cost Estimate

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