The Finch House, a 1921 estate in downtown Thomasville that operates as a wedding and event venue, changed hands for $1.90 million on August 14, 2026, the highest-priced home sale reported in the Winston, North Carolina metro area for the week ending August 16. The five sales combined for $5.85 million.
They span Thomasville, the Greenbrier Farm neighborhood of Winston Salem, Lake at Lissara in Lewisville, Bermuda Run and Fiddlers Ridge in Advance, with build years running from 1921 to 2026. Lake at Lissara and Bermuda Run are gated communities, and the newest house on the list was listed by its builder, Eastwood Construction Co., Inc.
No. 1 — $1,900,000 · 17 E Main St, Thomasville, North Carolina
The Finch House, at 17 E Main St in downtown Thomasville, changed hands for $1,900,000 on August 14, 2026, the metro area’s highest-priced reported sale of the week. Built in 1921 on roughly two acres of manicured grounds, it is recorded at 11 bedrooms and 14 baths across a reported 9,020 square feet and runs as a wedding and event venue, with capacity for 185 guests and overnight accommodations for 25.
Three buildings share the grounds. The main house, about 7,000 square feet, holds multiple event spaces, a commercial kitchen, bridal and groom suites and guest rooms. A 2,700-square-foot guest house adds five bedrooms, three baths, a full kitchen and a converted garage lounge, and a 1,300-square-foot carriage house contributes three more baths and further event space. The venue sold as a turnkey operation, with bookings transferring to the new owner into 2026.
Melissa Greer and Jim Howard of Berkshire Hathaway HomeServices Yost & Little Realty were the listing agents. The $1,900,000 closing put both agents on the listing side of the highest-priced sale reported in the Winston metro area that week β No. 1 in RealtyWire’s weekly Top 5 for the metro.
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No. 2 — $1,275,000 · 115 Northpond Ln, Winston Salem, North Carolina
A 1996 house on a private cul-de-sac lot in Greenbrier Farm closed on August 11, 2026 for $1,275,000, second in the metro for the week and $5,000 above its final asking price of $1,270,000. It went under contract 4 days after the current listing date, and it holds five bedrooms and five baths across a reported 5,084 square feet.
A 2024 renovation reworked much of the interior, with permits pulled for the work: walls were moved, the half bath and laundry relocated, a lower-level bedroom added and every bath renovated. The kitchen was rebuilt around an oversized island with custom cabinetry, a 48-inch six-burner range with a griddle and a 42-inch built-in refrigerator. Nine-foot ceilings and hardwood floors run through the main level, and a heated saltwater pool with a tanning ledge and travertine surround sits outside alongside a hot tub and a smokeless firepit. The property previously changed hands for $809,500 in 2023.
Nancy Huber of Berkshire Hathaway HomeServices Carolinas Realty was the listing agent. Chase Troxell of Leonard Ryden Burr Real Estate represented the buyer. The transaction ranked No. 2 in RealtyWire’s Winston metro area Top 5 for the week, and it closed above its final asking price.
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No. 3 — $1,110,000 · 385 Lissara Lodge Dr, Lewisville, North Carolina
A 2021 residence at 385 Lissara Lodge Dr took the No. 3 position, selling for $1,110,000 in The Lake at Lissara, a gated community in Lewisville. The sale closed August 10, 2026. Four bedrooms and four baths occupy a reported 3,683 square feet.
Listing materials identify RL Riddle as the builder. Hardwood floors and an open, light-filled plan run through the main level, where a kitchen built around a large island opens to the living room and a screened porch above a fenced backyard. The primary suite sits on the main floor with a spa-style bath and walk-in closet, beside a second main-level guest suite; two more bedroom suites, a bonus room, a private office and a walk-in attic fill the upper floor. Plantation shutters, a whole-house generator, irrigation and a three-car side-entry garage round out the house, which previously changed hands for $900,000 in 2022.
Pamelia Matthews of Howard Hanna Allen Tate – Winston Salem was the listing agent. The $1,110,000 closing placed Matthews at the listing side of the No. 3 sale in the metro area’s Top 5 for the week.
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No. 4 — $875,000 · 858 Riverbend Dr, Bermuda Run, North Carolina
Inside the gates of Bermuda Run, a remodeled 1972 house at 858 Riverbend Dr sold on August 12, 2026 for $875,000. The sale closed at its full asking price, and the property went under contract 6 days after the current listing date. Five bedrooms and four baths sit on 0.949 acres, with a reported 3,018 square feet.
The kitchen has been renovated, new flooring runs through the house and all of the bathrooms have been updated, including the main-level primary suite’s separate tub and shower. A 630-square-foot heated and cooled sunroom is not counted in the reported square footage. An in-ground pool and a new covered outdoor area anchor the back of the lot, and double front porches face the street. Optional membership in Bermuda Run Country Club carries golf, tennis, pickleball, pools and a lazy river. The property previously changed hands for $417,000 in 2025.
George Stabolitis of Leonard Ryden Burr Real Estate was the listing agent. Jennifer Reader of Keller Williams Realty Elite represented the buyer. Stabolitis held the listing on the week’s No. 4 reported sale in the Winston metro area, a transaction that met its full asking price.
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No. 5 — $687,239 · 416 Bingham And Parks Rd, Advance, North Carolina
New construction closed the list: a 2026-built house at 416 Bingham And Parks Rd in the Fiddlers Ridge community in Advance sold for $687,239. The sale closed August 14, 2026. Five bedrooms and four baths spread over three stories and a reported 3,567 square feet.
Built to the builder’s Davidson plan, the house puts a guest suite with a full bath on the first floor alongside a formal dining room, a family room, a kitchen with an island and pantry, a butler’s pantry and a breakfast area opening to a sunroom and a covered rear porch. Three bedrooms sit on the second floor, among them a primary bedroom with a sitting area and its own bath, plus a hall bath, a large laundry room and a loft. A fifth bedroom and full bath occupy the third floor.
Amanda Brooks of Eastwood Construction Co., Inc. was the listing agent. Lindsey King of R&B Legacy Group represented the buyer. Brooks represented the listing side of the No. 5 sale in RealtyWire’s Winston metro area Top 5 for the week, a newly completed home in Fiddlers Ridge.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, August 16, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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See full market data on our Winston, North Carolina market page.
