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

$749,900

4 Beds ⋅ 2 Baths ⋅ 3596448 MLS ⋅ ACTIVE Status ⋅ 1.01 Acres ⋅ 37211 Zip Code

ONE ACRE in Nashville with the space, privacy, updates, and location you've been looking for! Welcome to 5629 Highland Way, a beautifully updated 4-bedroom home ideally situated with convenient access to both Nashville and Brentwood. Zoned for Granbery Elementary, this home offers an exceptional combination of an established neighborhood, generous lot, and proximity to shopping, dining, parks, and everyday conveniences. Step inside to a light-filled interior featuring hardwood floors on the main level and a beautifully remodeled kitchen with custom cabinetry, granite countertops, designer lighting, tile backsplash, and quality finishes. The spacious primary suite features an updated bath, while newer Berber- Style carpet upstairs adds to the home's fresh, move-in-ready feel. Outside is where this property truly shines. Enjoy private backyard offering room to entertain, garden, play, or simply relax and take in the peaceful setting and beautiful views toward Brentwood's rolling hills. RV/camper-friendly setup with a conveniently located sewer clean out near the driveway for easy waste-tank disposal. Improvements include a newer roof, dual HVAC systems, newer water heater and chimney cap, plus windows with a transferable lifetime warranty. The garage provides additional storage and workspace. A Nashville address, an acre of land, privacy, beautiful updates, and convenient access to Brentwood . This home offers a combination that's increasingly hard to find. Come experience it for yourself!

5629 Highland Way, Nashville

$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

$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

$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

$460,000

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

$589,900

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

Welcome to 2832 Kensington Street, a stately all-brick home in The Highlands offering 3,721 square feet of finished living space, 4 bedrooms, 3 full baths, 2 half baths, a 2-car garage, and seasonal mountain views on 1.2 acres. Inside, oak hardwood flooring, a formal dining room, and an eat-in kitchen with custom cherry cabinetry, granite countertops, pantry storage, and a breakfast bar create a warm and functional main level. The kitchen opens to the living room with a brick fireplace, while the sunroom overlooks the patio and backyard. The second level includes the primary suite, additional bedrooms, and a bonus room, while the finished third level offers flexible space for an office, recreation room, guest area, or additional bedroom. Outside, the gently sloping, partially wooded lot provides room for outdoor living and recreation. Both HVAC systems have been replaced within the last five years. Conveniently located near Athens shopping, dining, medical facilities, and I-75, this home offers generous space, flexible living areas, and a beautiful setting in The Highlands.

2832 Kensington Street, Athens

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