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5 Grand Acreage Estates and Refined Retreats in Tennessee and Kentucky

By Awais Manzoor

1 min read

Luxury meant to be lived in, gathered in, and expanded beyond a single set of walls. Acreage and privacy set the stage, from a 10.5-acre Winchester retreat with a separate pool house to a La Grange colonial framed by a tree-lined drive and hobby-farm infrastructure. In Brentwood, timeless design and walkable access to parks and trails meet turnkey upgrades. Gatlinburg’s Arts & Crafts compound adds creekside serenity and creative flexibility.

3539 Liberty Road | $1,849,999

3539 Liberty Road, Winchester, TN 37398
3539 Liberty Road, Winchester, TN 37398
chesneyluttrell
LISTING AGENT:
Chesney Luttrell

Set on 10.5 sprawling acres, this exceptional property offers a perfect blend of space, comfort, and resort-style outdoor living. The 3,617 sq. ft. main residence features 6 bedrooms and 3.5 baths, along with a well-appointed kitchen with hickory cabinetry, black stainless steel appliances, quartz countertops, and an Electrolux built-in vacuum system. The impressive 2,840 sq. ft. pool house includes tongue-and-groove ceilings, hardwood floors, a full kitchen, and granite countertops, offering flexible space for entertaining, guests, or a private retreat. Outside, enjoy a spectacular 24×40 custom in-ground pool with two swim-outs, creating a private oasis for year-round recreation. With over 6,400 sq. ft. of combined living space and premium finishes throughout, this unique property is an entertainer’s dream.

Price:
$1,849,999
Size:
3,617 sq ft
Contact:
Chesney Luttrell, John Smith Jr Realty and Auction LLC, 931-308-4695

1828 Bronwyn CT | $1,825,000

1828 Bronwyn Ct, Brentwood, TN 37027
1828 Bronwyn Ct, Brentwood, TN 37027
rachelmargolis
LISTING AGENT:
Rachel Margolis

On a quiet cul-de-sac in Brentwood, a circular driveway introduces a grand, timeless residence marked by a striking steel front door. Inside, plantation shutters dress every window, lending a consistent note of classic charm. The kitchen balances beauty and function with quartz countertops, a tiled backsplash, stainless-steel appliances, and a luxury cooktop crowned by a statement hood. Four bedrooms feature ensuite baths designed for a spa-like sense of comfort, while a fifth bedroom currently serves as an office with custom built-ins. Three interior fireplaces add warmth and character across the living spaces. Outdoors, a covered back patio offers a fourth fireplace and peaceful views of the private backyard; from the front porch, sunset views close the day. A short walk connects you to Smith Park, Ravenwood High School, and the Brentwood Trail System.

Price:
$1,825,000
Size:
5,165 sq ft
Contact:
Rachel Margolis, Compass, 310.403.7891

Turtle Hollow Estates A Legacy Unlike Anything Else In Gatlinburg | $1,692,000

248 Buckhorn Rd, Gatlinburg, TN 37738
248 Buckhorn Rd, Gatlinburg, TN 37738
katelynwarren
LISTING AGENT:
Katelyn Warren

Tucked within Gatlinburg’s celebrated Arts & Crafts Community, Turtle Hollow Estates unfolds as a 1.48-acre 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. Across five distinct buildings, a beautifully renovated main residence is joined by a private apartment, a dedicated studio, an oversized shop with a heavy-duty lift and man cave, and a separate climate-controlled workshop—an uncommon mix of creativity and capability in one setting. Extensive infrastructure and smart-home integration support everyday ease, while more than $150,000 in landscaping and outdoor enhancements refine the grounds. With an optional additional buildable parcel available, the estate leaves room for new ideas to take shape over time.

Price:
$1,692,000
Size:
7,430 sq ft
Contact:
Katelyn Warren, Century 21 Legacy, 865.416.2220

9702 Amethyst Lane | $1,449,900

9702 Amethyst Ln, Brentwood, TN 37027
9702 Amethyst Ln, Brentwood, TN 37027
julierussell
LISTING AGENT:
Julie Russell

Set on a half-acre+ lot in Brentwood’s Woodlands at Copperstone, 9702 Amethyst Lane pairs thoughtful updates with a layout designed for everyday ease. Renovated throughout, the interiors feature new windows, fresh paint, designer lighting, soaring vaulted ceilings, and hardwood floors. At the center, a chef’s kitchen is anchored by a $19K AGA dual-fuel range with double oven—equally suited to weeknight dinners and weekend hosting. Four spacious ensuite bedrooms, including a main-level primary suite with a spa-inspired bath, create a sense of privacy and comfort. An oversized bonus room and dedicated office add flexibility, while a 3-car garage with epoxy flooring keeps storage streamlined. Outside, an enclosed porch, expansive deck, and fully fenced backyard extend living outdoors, with irrigation and Level 2 EV chargers rounding out the details, plus community pool access.

Price:
$1,449,900
Size:
4,680 sq ft
Contact:
Julie Russell, Adaro Realty, 801.554.1338

2301 Cedar Point Rd | $1,400,000

2301 Cedar Point Rd, La Grange, KY 40031
2301 Cedar Point Rd, La Grange, KY 40031
mindyparrish
LISTING AGENT:
Mindy Parrish

Surrounded by more than 10 scenic acres in sought-after Oldham County, this stately two-story Colonial arrives with a tree-lined driveway, a classic columned façade, and a brick front porch overlooking mature woods and landscaped gardens. Life here is designed to move easily between indoors and out, with a private in-ground pool and room to roam across four-board fenced horse pastures. A small barn, chicken coop, and a versatile metal building support everything from equestrian pursuits to hobby-farm routines and weekend projects. Inside, timeless craftsmanship sets the tone—crown molding, hardwood flooring, and tile finishes throughout. The spacious kitchen features white cabinetry, a center island, double ovens, and a gas cooktop for everyday meals and entertaining alike. Downstairs, a finished basement adds flexible living space with a recreation room, where the pool table and accessories may convey. Minutes from I-71, country quiet comes with everyday convenience.

Price:
$1,400,000
Size:
4,047 sq ft
Contact:
Mindy Parrish, Coldwell Banker McMahan, 502-750-2601