5 Sprawling Tennessee Estates and a Kentucky Colonial Retreat

Set on 10.5 sprawling acres in Winchester, this exceptional property balances generous interior space with resort-style outdoor living. The main residence offers room for family, guests, and gatherings, anchored by a well-appointed kitchen with hickory cabinetry, black stainless steel appliances, quartz countertops, abundant storage, and ample workspace. An Electrolux built-in vacuum system adds everyday ease.

On a quiet cul-de-sac in Brentwood, a circular driveway leads to a grand, timeless residence where a striking steel front door hints at the refinement within. Plantation shutters frame every window, lending a consistent, classic note throughout. The kitchen balances beauty and utility with quartz countertops, a tiled backsplash, stainless-steel appliances, and a luxury cooktop crowned by a statement hood. Four bedrooms feature ensuite bathrooms designed for a spa-like sense of ease, while a fifth bedroom currently serves as an office with custom built-ins. Three interior fireplaces add warmth and character across the main living spaces. Outside, a covered back patio offers a fourth fireplace and peaceful views of the private backyard; the front porch is made for sunset watching. Walk to Smith Park, Ravenwood High School, and the Brentwood Trail System for miles of scenic paths.

Tucked into Gatlinburg’s celebrated Arts & Crafts Community, Turtle Hollow Estates unfolds across 1.48 acres as a private compound shaped by artistic heritage and mountain beauty. Once home to renowned artist Ross Markley, the property pairs Buckhorn Creek frontage with views of Mt. LeConte and direct access to nearby hiking trails. Five distinct buildings create a rare, flexible mix of spaces: a beautifully renovated main residence, a private apartment, a dedicated studio, an oversized shop with a heavy-duty lift and man cave, and a separate climate-controlled workshop. Extensive infrastructure and smart-home integration support day-to-day ease, while more than $150,000 in landscaping and outdoor enhancements polish the grounds. With an optional additional buildable parcel available, the estate leaves room for new chapters in a true Smoky Mountain legacy setting.

Set on a half-acre+ lot in Brentwood’s Woodlands at Copperstone, 9702 Amethyst Lane pairs thoughtful updates with an easy, everyday flow. Renovated throughout, the interiors feature new windows, fresh paint, designer lighting, soaring vaulted ceilings, and hardwood floors that carry from room to room. The chef’s kitchen anchors the home with a $19K AGA dual-fuel range, double oven, and a layout designed for real cooking and gathering. Four spacious ensuite bedrooms—including a main-level primary suite with a spa-inspired bath—offer comfort and privacy, while an oversized bonus room and dedicated office add flexibility for work and play. Outside, an enclosed porch and expansive deck overlook a fully fenced backyard, supported by an irrigation system. Level 2 EV chargers, a 3-car garage with epoxy flooring, and community pool access round out a polished Brentwood lifestyle.

Surrounded by more than 10 scenic acres in sought-after Oldham County, this stately two-story Colonial pairs classic symmetry with a quietly pastoral setting, just minutes from I-71. A tree-lined driveway leads to a columned façade and brick front porch, framed by mature woods and landscaped gardens. Outdoor life is richly considered: a private in-ground pool, four-board fenced horse pastures, a small barn, a chicken coop, and a versatile metal building suited to equestrian, hobby-farm, or recreational use. Inside, timeless craftsmanship shows in crown molding, hardwood flooring, and tile finishes. The spacious kitchen balances beauty and utility with white cabinetry, a center island, double ovens, and a gas cooktop. A finished basement adds flexible living space with a recreation room, and a pool table may convey. Days here unfold with privacy, breathing room, and easy access to modern conveniences.