The Highlands Real Estate

Welcome to The Highlands, a premier subdivision located in Winchester, Franklin County, Tennessee. Nestled in the heart of this beautiful state, The Highlands offers a unique living experience that combines the charm of a small town with the convenience of nearby amenities.

Situated in Franklin County, residents of The Highlands enjoy the tranquility of a rural setting while still being within easy reach of urban conveniences. Winchester, the city where The Highlands is located, is known for its picturesque landscapes, friendly community, and rich history. This region is perfect for those seeking a peaceful and close-knit community to call home.

The Highlands offers a range of housing options to suit different needs and preferences. From spacious single-family homes to cozy townhouses, there is something for everyone. The subdivision features well-maintained streets, beautiful landscaping, and a variety of recreational amenities for residents to enjoy.

In addition to its natural beauty, The Highlands benefits from its proximity to Winchester's downtown area, which is home to a range of shops, restaurants, and entertainment options. Outdoor enthusiasts will also appreciate the nearby Tims Ford State Park, where they can explore hiking trails, go boating or fishing, and enjoy picnicking with family and friends.

If you are looking for a peaceful and welcoming community in Tennessee, The Highlands in Winchester is the perfect place to call home. Come and experience the charm and beauty of this subdivision for yourself.

Newest Listings in The Highlands

$629,000

4 Beds ⋅ 3 Baths ⋅ 3513630 MLS ⋅ ACTIVE Status ⋅ 0.32 Acres ⋅ 37167 Zip Code

Welcome to 3701 Henricks Hill Drive! This home is a beautifully updated retreat with flexible multi-generational living options. This home is tucked away in a great development minutes from central Smyrna, I24, shopping and dining. The backyard is a wooded oasis. The home has been completely updated including flooring, plumbing, painting, lighting and appliances. Offering four bedrooms, three full baths, 3 living spaces each with a fireplace and a flex office or dining room. Multiple sky lights and lots of windows give this home beautiful natural lighting. Primary suite is located on main level and includes a beautiful updated ensuite bath. The interior has been thoughtfully update throughout.with multiple french doors accessing outside entertainment space. Home has built-ins in kitchen area, wood shutters, large pantry and laundry room off kitchen. Upstairs includes 2 bedrooms and a bath. There is a beautiful outdoor balcony off one bedroom that could be a second floor primary bedroom. Step outside and enjoy the serenity of the park-like backyard, where the property's wooded backdrop creates privacy and peaceful connection to nature. The spacious two-car garage and encapsulated crawlspace with additional storage/work out room with outside access via double door. HVAC installed 2025. Great location close to Rock Springs Middle School and Paul Johns Park and walking trails. Cul de sac privacy, walking access to Greenway and close to shopping and dining.This home has the rare combination of privacy, flexible living space, extensive updates and move in ready. Buyer and Buyer's Agent to verify all information including school zones. Photo shows virtually staged room. Buyer and Buyer's Agent to verify all information including school zones.

3701 Henricks Hill Dr, Smyrna

$2,250,000

3500774 MLS ⋅ ACTIVE Status ⋅ 15.65 Acres ⋅ 37179 Zip Code

Set within the rolling landscape of Middle Tennessee, this approximately 15.65-acre homesite in The Highlands offers a rare opportunity to create an estate that is deeply connected to the land. Framed by sweeping Tennessee vistas and natural beauty in every direction, the property provides an extraordinary canvas for a custom residence where timeless architecture and the surrounding landscape exist in perfect harmony. The property features two primary homesites, each accommodating up to six bedrooms, along with an accessory homesite for a two-bedroom guest house, pool house, studio, or additional living space, providing exceptional flexibility to create a private family compound or a one-of-a-kind retreat tailored to your lifestyle. Property features include an old tobacco barn and hay barn, which could easily be transformed into an indoor wellness center, as well as creeks and a pond. With expansive acreage, remarkable privacy, and sweeping Tennessee vistas, the property offers endless opportunities for outdoor living, recreation, gardens, equestrian use, and resort-style amenities. It is an ideal canvas for creating a legacy property 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 convenience. Bring your own builder and vision, or collaborate with the established builder and design team. For inspiration, explore the stunning residence planned for 1914 Thompson's Station Road West, Lot 2, or create a fully custom estate that reflects your own vision and lifestyle.

1914 W Thompsons Station Rd, Thompsons Station

$8,250,000

6 Beds ⋅ 9 Baths ⋅ 3500773 MLS ⋅ ACTIVE Status ⋅ 15.65 Acres ⋅ 37179 Zip Code

Welcome to Evermore at The Highlands, where timeless Cotswold-inspired architecture offers an elevated lifestyle just minutes from historic downtown Franklin and Leiper's Fork. Thoughtfully designed by David Design Group, this estate is positioned to capture panoramic views while feeling as though it has always belonged. The residence will showcase natural stone, cedar shake roofing, and curated materials that create a home rich in character, patina, and timeless beauty. Set on approximately 15.65 private acres, this extraordinary new construction estate spans more than 10,300 square feet. Designed for refined everyday living and effortless entertaining, the home features expansive living and dining spaces filled with natural light. At its heart, the chef's kitchen with double islands and a breakfast nook flows into gathering spaces anchored by a striking double-sided fireplace. The private primary suite is a retreat of its own, complete with a sitting area, coffee bar, dedicated office, dual walk-in closets, and a spa-inspired bath. Additional highlights include a club room, bonus room with an en suite bath, bunk room, gym with sauna, elevator, mudroom, mail room, and utility rooms on both levels. Outdoors, a resort-style pool overlooks the rolling countryside, while a porte cochère, attached three-car garage, and separate one-car garage with finished guest quarters above complete the estate. Beyond the residence, the property is approved for two additional six-bedroom homesites plus an accessory homesite, creating a rare opportunity for a private family compound, multigenerational estate, or future expansion. Property features include an old tobacco barn and hay barn with potential to become an indoor wellness center, as well as creeks and a pond. Evermore at The Highlands is where timeless architecture, thoughtfully curated design, and the beauty of Tennessee come together to create a legacy property unlike any other.

1914 W Thompsons Station Rd, Thompsons Station

$625,000

3 Beds ⋅ 4 Baths ⋅ 3337198 MLS ⋅ ACTIVE Status ⋅ 0.81 Acres ⋅ 37303 Zip Code

Welcome to 3046 Hawthorne Street--an extensively upgraded 3-bedroom, 3.5+ bath home offering over 3,300 square feet of living space on a private 0.81-acre lot in one of Athens' most desirable neighborhoods. Ideally located between Knoxville and Chattanooga, this property delivers the perfect balance of space, privacy, and convenience. Inside, the home features a well-designed layout with multiple living areas, including a finished basement with potential for separate living quarters, workshop space, or future kitchenette with plumbing already in place. The main level offers seamless flow between the kitchen, dining, and living spaces, highlighted by Cambria quartz countertops, cherry cabinetry, stainless steel appliances, and a gas fireplace that opens to a screened-in porch. Throughout the home, you'll find hardwood flooring, Anderson windows, and plantation shutters for a timeless, move-in-ready feel. Enjoy peace of mind with major system upgrades, including a new Coleman 2.5-ton gas HVAC system, on-demand water heater, enhanced attic insulation and ventilation, and gutter guards--providing efficiency and reduced maintenance for years to come. Step outside to your own private retreat, featuring an in-ground pool with updated equipment and custom cover, a Bahama Spas 5-person hot tub, and multiple outdoor living spaces including a screened porch, fire pit, lower patio, and multi-level deck. A 6-foot vinyl privacy fence, dual-gate access, and mature landscaping complete the setting. Offering more space and features than many comparable homes in nearby metro areas, this property is a rare find in the Athens market. Schedule your private showing today to experience everything this home has to offer.

3046 Hawthorne Street, Athens

$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 Thompsons 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 Thompsons 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

$598,900

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

$57,900

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

$57,900

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.