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Sale Pending at 365 Sherwood Dr S, Flat Rock, NC 28731 | MLS# 4353114 | Listing updated on 2026-09-01
Photo 1 of Sale Pending at 365 Sherwood Dr S, Flat Rock, NC 28731 | MLS# 4353114 | Listing updated on 2026-09-01
Photo 2 of Sale Pending at 365 Sherwood Dr S, Flat Rock, NC 28731 | MLS# 4353114 | Listing updated on 2026-09-01
Photo 3 of Sale Pending at 365 Sherwood Dr S, Flat Rock, NC 28731 | MLS# 4353114 | Listing updated on 2026-09-01
Photo 4 of Sale Pending at 365 Sherwood Dr S, Flat Rock, NC 28731 | MLS# 4353114 | Listing updated on 2026-09-01
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$2,995,000

Monthly Est:$14,907

  • Beds Icon5 Beds
  • Beds Icon
    6 Baths
  • Beds Icon7,031sqft

365 Sherwood Dr S, Flat Rock, NC 28731

$14,907/moEst:

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  • Single Family Residence

  • Built in 1938

  • $216.67/mo HOA

  • 5.83 acres lot

  • $426/sq.ft

Description

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.

  • Houzeo last checked: 4 hours ago
  • Listing updated: September 1, 2026 at 5:46 pm
  • Listing Provided by: Marilyn Wright (828) 279-3980 | Premier Sotheby’s International Realty (828) 277-3238
  • Source: Canopy MLS | MLS#: 4353114 Canopy MLS

Property Details

  • Status

    Pending

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Henderson County

  • City

    Flat Rock

  • Neighborhood

    --

  • Year Built

    1938

  • HOA Fees

    $216.67/mo

  • Finished Area

    7,031 sqft

  • Lot Size

    5.83 acres lot

  • Basement Area

    - sqft

  • MLS Name

    Canopy MLS

  • MLS Number

    4353114

  • MLS Status

    Under Contract-No Show

  • Days on Market

    191

  • Cumulative Days on Market

    122

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Location

HOA Management

Cedar Management Group

HOA Fees

$2,600/ Annually

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 5

    Bathrooms: 6

Interior

  • Sewer

    Septic Installed

  • Exterior Features

    Fire Pit

  • Interior Features

    Attic Stairs Pulldown, Built In Features, Elevator, Entrance Foyer, Kitchen Island, Pantry, Storage, Walk In Closet(s), Walk In Pantry, Wet Bar

  • Flooring

    Stone, Wood

  • Window Features

    Insulated Window(s)

  • Heating

    Heat Pump, Natural Gas

  • Cooling

    Zoned

  • Appliances

    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

Construction

  • Year Built

    Year Built: 1938

  • Home type

    Single Family Residence

  • Roof

    Metal

  • Architectural Style

    Traditional

  • Construction Materials

    Brick Full

  • Foundation Details

    Basement

Utilities & Energy

  • Security Features

    Carbon Monoxide Detector(s), Security System

  • Basement

    Exterior Entry, Unfinished, Walk Out Access

  • Parking Features

    Driveway, Attached Garage, Detached Garage

  • Fireplace Features

    Family Room, Gas Log, Living Room, Primary Bedroom

  • Laundry Features

    In Basement, Multiple Locations

  • Water Source

    City

Other Features

  • Patio And Porch Features

    Patio, Porch, Rear Porch, Side Porch

  • Lot Features

    Cleared, Green Area, Level, Pasture, Wooded

  • Subdivision Name

    Sherwood

Price History

DateEventPrice

09/01/2026

Source: #CAR4353114

Pending

$2,995,000

$426/sqft

07/31/2026

Source: mls_logoCanopy MLS #CAR4353114

Contingent (Active Under Contract)

$2,995,000

$426/sqft

07/16/2026

Source: mls_logoCanopy MLS #CAR4353114

Price Decreased

$2,995,000 -17.95%

$426/sqft

05/13/2026

Source: mls_logoCanopy MLS #CAR4353114

Price Decreased

$3,650,000 -7.59%

$519/sqft

03/31/2026

Source: mls_logoCanopy MLS #CAR4353114

Listed for Sale

$3,950,000 -12.22%

$562/sqft

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Nearby Homes

Based on information submitted to the MLS GRID from Canopy MLS through Oct 08, 2026, 11:00AM. All data is obtained from various sources and may not have been verified by the 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. IDX information is provided exclusively for consumers’ personal, noncommercial use. It may not be used for any purpose other than to identify prospective properties which the consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. ©2026 Canopy MLS. All Rights Reserved.

Advertising Broker: Nicholas Huscroft | Chosen Realty