The Highlands Real Estate

Welcome to The Highlands, a picturesque subdivision nestled in the heart of Winchester, Tennessee, within the charming Franklin County. This tranquil community offers a perfect blend of natural beauty and modern living, making it an ideal place for families, retirees, and anyone seeking a peaceful retreat.

The Highlands boasts spacious lots adorned with mature trees, lush landscaping, and stunning views of the surrounding hills, providing a serene backdrop for your dream home. The area is known for its friendly neighbors and strong sense of community, where residents often gather for seasonal events and neighborhood barbecues. With a variety of architectural styles, from contemporary designs to classic Southern charm, you’ll find the perfect home that reflects your personal taste.

Conveniently located just minutes from downtown Winchester, The Highlands offers easy access to local shops, restaurants, and essential services. Outdoor enthusiasts will appreciate the proximity to beautiful parks and recreational areas, including nearby Tim’s Ford Lake, where you can enjoy boating, fishing, and hiking along scenic trails.

Families will also benefit from the highly-rated schools in the area, ensuring a quality education for children of all ages. With its blend of rural charm and modern conveniences, The Highlands is more than just a place to live; it’s a community where you can create lasting memories.

Discover the allure of The Highlands, where your dream home awaits amidst the natural beauty of Tennessee. Come and experience the warmth and charm of this exceptional subdivision today!

Newest Listings in The Highlands

$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

$3,000,000

3287541 MLS ⋅ ACTIVE Status ⋅ 20 Acres ⋅ 37179 Zip Code

Experience pristine Tennessee living on 20 breathtaking acres in The Highlands, where rolling hills, panoramic views, and the natural beauty of Middle Tennessee create an extraordinary setting for a legacy estate. Thoughtfully positioned to complement the surrounding landscape, this exceptional parcel offers a rare opportunity to create a timeless custom residence that feels as though it has always belonged. 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. With expansive acreage, remarkable privacy, and sweeping Tennessee vistas, the property offers endless possibilities for outdoor living, recreation, gardens, equestrian use, and multigenerational living. It is an ideal canvas for creating a one-of-a-kind retreat designed to be enjoyed for generations. Conveniently located just minutes from historic downtown Franklin, Leiper’s Fork, Williamson County schools, shopping, and dining, this property offers the perfect balance of peaceful country living and everyday accessibility. Bring your own builder and vision, or work with the established builder and design team. For inspiration, explore the stunning residence planned for 1914 Thompson’s Station Road West, Lot 1, or create an entirely custom home tailored to your lifestyle.

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

$64,900

2792698 MLS ⋅ ACTIVE Status ⋅ 0.55 Acres ⋅ 37398 Zip Code

New Gated Community, The Highlands! Located less than one minute from Tims Ford Lake (public boat launch on Sharp Springs Rd). Convenient to shopping and dining.

66 Edgefield Ct, Winchester

$64,900

2792697 MLS ⋅ ACTIVE Status ⋅ 0.28 Acres ⋅ 37398 Zip Code

New Gated Community, The Highlands! Located less than one minute from Tims Ford Lake (public boat launch on Sharp Springs Rd). Convenient to shopping and dining. Underground utilities and security gate.

67 Edgefield Ct, Winchester

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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.