The Highlands Homes for Sale

Welcome to The Highlands, an enchanting subdivision nestled in the heart of Winchester, Tennessee, within the picturesque Franklin County. This charming community is designed for those who appreciate the perfect blend of serene living and modern convenience. The Highlands is not just a neighborhood; it's a lifestyle, offering residents a tranquil retreat surrounded by nature while being just moments away from the vibrant amenities of Winchester.

The Highlands features an array of beautifully crafted homes for sale, each showcasing unique architectural styles and thoughtful designs. Whether you’re searching for a cozy single-family home or a spacious abode perfect for entertaining, this subdivision has something to suit every taste and need. The properties often boast expansive yards, modern finishes, and breathtaking views of the rolling hills that define this stunning area.

Residents of The Highlands enjoy easy access to local parks, hiking trails, and recreational opportunities, making it an ideal location for outdoor enthusiasts and families alike. The community fosters a friendly atmosphere, with neighbors often coming together for seasonal events and gatherings.

With homes for sale in The Highlands, you have the chance to become part of this vibrant community. Explore the possibilities of your new life in Winchester, where southern charm meets modern living. Don’t miss out on the opportunity to call The Highlands your home; reach out today to discover the perfect property that fits your lifestyle!

Newest The Highlands Homes for Sale

$8,500,000

5 Beds ⋅ 8 Baths ⋅ 3287540 MLS ⋅ ACTIVE Status ⋅ 20 Acres ⋅ 37179 Zip Code

Introducing “Cadence at The Highlands,” an extraordinary Tennessee estate where timeless Cotswold inspired architecture, exceptional craftsmanship, and a highly curated luxury lifestyle will come together in perfect harmony with the surrounding landscape. Set on 20 breathtaking private acres, Cadence has been thoughtfully designed by David Design Group and carefully positioned to capture sweeping panoramic views while feeling as though it has always belonged among the rolling hills of Middle Tennessee. Pritchett Smith Builders will construct the residence, showcasing natural stone, cedar shake roofing, and carefully selected materials intended to create a home rich in character, patina, and timeless beauty. Designed for both refined everyday living and effortless entertaining, the residence will feature a chef’s kitchen, private office, elevator, entertainment foyer, and a spectacular primary suite complete with a spa inspired bath and dual walk in closets connected by a dramatic two story custom wardrobe. The finished lower level is planned as a destination for recreation and wellness, with a golf simulator, theater, fitness center, sauna, cold plunge, playroom, kitchenette, and pantry. The outdoor living spaces are equally impressive and include a private courtyard, resort style pool, expansive gathering areas, and garage accommodations for four vehicles. Beyond the featured residence, the property is approved for two primary residences, each accommodating six or more bedrooms, providing exceptional flexibility to create a multigenerational family compound, private guest residences, or a lasting legacy estate. Perfectly positioned just minutes from historic downtown Franklin, Leiper's Fork, Williamson County schools, shopping, and dining, Cadence offers a rare blend of privacy, natural beauty, and timeless luxury, thoughtfully designed to create a lasting legacy for generations to come.

1914 W Thompson Station Rd, Thompsons Station

$455,000

3 Beds ⋅ 3 Baths ⋅ 3248387 MLS ⋅ ACTIVE Status ⋅ 0.33 Acres ⋅ 37398 Zip Code

Welcome to this meticulously designed new home! The residence features three spacious bedrooms and two bathrooms, along with a supplemental room with a half bath. It includes upscale features like top-of-the-line stainless steel appliances, custom-built expansive wardrobes, and an exquisite coffered ceiling in the main living area. Through precise craftsmanship and the use of premium materials, this home is ready to provide a blend of opulence and sophistication to its first occupant. Don't miss out on this move-in-ready gem.

201 Lookout Dr, Winchester

$618,800

4 Beds ⋅ 5 Baths ⋅ 3244421 MLS ⋅ ACTIVE Status ⋅ 1.2 Acres ⋅ 37303 Zip Code

A stately all-brick home located in one of Athens' most desirable neighborhoods, The Highlands. It boasts a premium location high on a ridge, featuring spectacular views within a quiet, friendly, and welcoming community. The property is located on a large 1.2-acre, gently sloping lot that is partially wooded. As you enter through the front door, you are greeted by an oak staircase, oak hardwood flooring, and a high ceiling. The eat-in kitchen features custom cherry cabinets, granite countertops, a pantry closet, and solid oak flooring. The kitchen is open to a living room, which features a brick fireplace with an insert. Directly adjacent to the living room is a sunroom that provides scenic views of the patio, backyard, and woods. Also on the first floor is a separate formal dining room and a versatile, generously sized room that could serve as an office, playroom, TV room, or music room. On the second level, you will find the primary suite with beautiful mountain views. The bathroom has double vanities, a garden tub, a shower and walk-in closet, and plenty of storage. Also on the second level, there are two additional bedrooms with generous closet space and a bonus room (which could be used as a bedroom) along with one full and one half-bath. The third level offers breathtaking views of the mountains. This expansive room with a full bath and three closets could serve as another bedroom, bonus room, or office. Also on this level, there is a pull-down ladder that provides access to the insulated fourth-level attic with a full floor and ceilings high enough for an adult to stand and walk. Numerous large trees were removed, and stumps were ground, with the vision of a large, level backyard, providing plenty of room for backyard activities. The septic tank and leaching field are located in the front yard, making a swimming pool possible in the backyard. Both HVAC systems have been replaced within the last five years.

2832 Kensington Street, Athens

$585,000

1 Beds ⋅ 1 Baths ⋅ 3229263 MLS ⋅ ACTIVE Status ⋅ 1.48 Acres ⋅ 37385 Zip Code

One of the most STUNNING views in Tellico Plains will welcome you as you walk in the front door! The deck overlooks the green plains of Tellico and stretches out to the base of the Appalachian Mountain range and the Cherokee National Forest. Nestled in one of the few gated neighborhoods that allow short-term rentals, this beautiful cabin offers great earning potential. The wide and partially covered deck provides amble room for entertaining or just relaxing in the hot tub and enjoying the stunning sunsets. The open floor plan offers towering windows with panoramic views from any seat in the house. The kitchen is fully equipped with a gas range, stainless steel hood, a farmhouse apron sink, textured granite counter tops, abundant cabinet space, island with breakfast bar and a dining nook with the scenic view. Rustic hardwood floors are throughout the home and authentic barn wood doors add charm to the bedroom and bathroom. Upstairs is a spacious loft making the perfect second bedroom space offering an open scenic view. This gated neighborhood offers paved roads and affordable HOA fees that cover your water bills. This home is fully furnished and stocked as a short-term rental. Great income potential or a perfect spot to call home! Tellico Plains offers world-class trout fishing and kayaking, hiking, camping, horseback trails, and small-town charm. Call today to schedule your private showing. Please provide ample advanced notice for showings, as the cabin is booked most nights.

117 Skyline Drive, Tellico Plains

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Information Is Believed To Be Accurate But Not Guaranteed. Some or all listings may or may not be listed by the office/agent presenting these featured properties. Copyright 2026 MTRMLS, Inc. RealTracs Solutions.