Five Oaks Homes with Lebanon High School

Welcome to Five Oaks, a picturesque subdivision nestled in the heart of Lebanon, Tennessee, within the charming Wilson County. Known for its tranquil atmosphere and beautiful landscapes, Five Oaks offers a perfect blend of suburban comfort and modern amenities, making it an ideal community for families, professionals, and retirees alike.

As you stroll through the tree-lined streets of Five Oaks, you'll discover a variety of stunning homes that cater to diverse tastes and lifestyles. From spacious single-family residences to elegant townhomes, each property is thoughtfully designed with quality craftsmanship and contemporary features. With well-manicured lawns and inviting outdoor spaces, residents enjoy the perfect setting for relaxation and recreation.

One of the standout features of Five Oaks is its proximity to Lebanon High School, making it an attractive choice for families with school-aged children. The school is known for its commitment to academic excellence and a wide range of extracurricular activities, providing students with a well-rounded education. Living in Five Oaks means your children can benefit from a top-notch education while being just a stone's throw away from home.

In addition to its educational offerings, Five Oaks is conveniently located near local shops, restaurants, and recreational facilities. Enjoy weekend outings at nearby parks, or take advantage of the community's amenities, including walking trails and playgrounds. With easy access to major highways, commuting to Nashville or other surrounding areas is a breeze.

Discover the charm of Five Oaks today, where a welcoming community, beautiful homes, and exceptional schools come together to create a truly delightful living experience in Lebanon, TN.

Newest Five Oaks Homes with Lebanon High School

$619,990

4 Beds ⋅ 4 Baths ⋅ 3602310 MLS ⋅ ACTIVE Status ⋅ 0.15 Acres ⋅ 37087 Zip Code

GOLF COURSE HOMESITE! Sellers offering $10,000 towards a rate buydown with the use of preferred lender! Welcome to an exceptional home perfectly positioned on Hole 4 of the Five Oaks golf course community. This premium lot (without the price tag) offers incredible golf course views and a thoughtfully designed open layout (Gladstone Plan), this home combines luxury, comfort, and functionality in every detail. Inside you’ll find spacious living areas filled with natural light, large bedrooms, and an abundance of storage throughout. Better than new, this home is loaded with builder upgrades and elevated even further with custom updates that make it truly one of a kind. No need to worry about appliances or window shades because they all stay with the home! Just one more plus compared to a new build. The stunning primary suite features a spa-like super shower and a walk-in closet with custom wood shelving. Designer lighting and custom accent walls throughout the home add warmth, character, and style. Every space has been carefully curated to create a home that feels both refined and inviting. Step outside and enjoy breathtaking views of the golf course…the perfect backdrop for relaxing evenings or entertaining guests! This is luxury golf course living at its finest in the highly sought-after Five Oaks community.

1089 Callaway Dr, Lebanon

$2,450,000

5 Beds ⋅ 8 Baths ⋅ 3530065 MLS ⋅ ACTIVE Status ⋅ 1.27 Acres ⋅ 37087 Zip Code

Exceptional brick and stone estate in the highly sought-after Five Oaks Golf & Country Club, where timeless architecture, exceptional craftsmanship, and resort-style amenities come together. Designed for elegant entertaining and luxurious everyday living, this impressive home showcases beautiful hardwood and tile flooring, extensive crown molding, custom iron doors, built-in cubbies, and refined architectural details throughout. The stunning gourmet kitchen features a built-in refrigerator, stainless steel appliances, wrap-around bar, and spacious eat-in area with a beautiful fireplace. A formal dining room provides an elegant setting for special occasions, while the private office showcases striking coffered wood ceilings. The luxurious primary suite offers a relaxing sitting area with fireplace and an impressive spa-like bath featuring an enclosed walk-through shower, double shower heads, rain shower head, separate tub, and two toilets with bidets. Additional bedrooms offer flexibility, including Bedroom 3 with a walk-out balcony and Bedroom 4 with a dedicated office area and built-in nook. Entertainment spaces are exceptional, featuring a large game room, private theater with a 120-inch screen, and two wet bars—perfect for movie nights, game days, parties, and gatherings. Step outside to your own private resort with a sparkling saltwater pool and slide, creating the perfect setting for summer entertaining and relaxation. The third floor is expandable, offering exciting potential for additional living space, while the home is pre-wired for a future elevator. Combining sophisticated design, generous living spaces, extraordinary entertainment amenities, and future expansion potential, this remarkable Five Oaks estate offers a lifestyle designed for both grand entertaining and comfortable everyday living.

107 Glenhaven Ct, Lebanon

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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.