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. This vibrant community is perfect for families, professionals, and retirees alike, offering a serene escape while still being conveniently close to the amenities of city life.

Five Oaks boasts a range of beautifully designed homes that cater to diverse lifestyles and preferences. From modern single-family residences to elegant townhomes, each property reflects a commitment to quality and craftsmanship. Many of these homes feature spacious layouts, contemporary finishes, and lush outdoor spaces, making them ideal for entertaining or enjoying quiet evenings with loved ones.

One of the standout features of Five Oaks is its proximity to Lebanon High School, making it an attractive choice for families with school-age children. The school is renowned for its commitment to academic excellence and a well-rounded education, providing students with the tools they need to succeed. Parents can take comfort in knowing that their children are just a short drive away from a top-notch educational experience.

In addition to its family-friendly atmosphere, Five Oaks is surrounded by natural beauty, with scenic parks and recreational areas nearby. Residents can enjoy walking trails, picnic spots, and a variety of outdoor activities, all while soaking in the stunning landscapes that Tennessee is known for.

If you're looking for a community that combines the charm of suburban living with the conveniences of city life, Five Oaks in Lebanon is the perfect place to call home. Explore the possibilities and discover a lifestyle that truly embraces the best of Tennessee living!

Newest Five Oaks Homes with Lebanon High School

$2,500,000

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

$724,990

4 Beds ⋅ 4 Baths ⋅ 3513826 MLS ⋅ ACTIVE Status ⋅ 37087 Zip Code

WALK OUT BASEMENT ON GOLF COURSE! Five Oaks Golf and Country Club! GENEROUS BUILDER INCENTIVE w/ preferred lender and title. Plus, purchase a David Weekley Home in The Preserve at Five Oaks and receive either a complimentary Social Club Membership initiation fee worth $5,000, or a $5,000 credit toward a full Golf Club Membership initiation fee at The Club at Five Oaks. This to-be-built home will feature a spacious Gladstone plan with a walk-out basement, offering plenty of space and the opportunity to customize your home to fit your lifestyle. Make the home truly yours by visiting our design studio, where you will select finishes, fixtures, colors and other design details to add your own personal touches. Final sales price is dependent upon the design and flex selections made.

1147 Callaway Drive, Lebanon

$704,990

4 Beds ⋅ 3 Baths ⋅ 3513818 MLS ⋅ ACTIVE Status ⋅ 37087 Zip Code

BASEMENT Homesite on the GOLF COURSE at FIVE OAKS. Generous builder incentives offered. Build your dream home on this beautiful golf-course homesite in Five Oaks! This to-be-built home will feature the popular Satinwood floorplan with a walk-out basement, offering plenty of space and the opportunity to customize your home to fit your lifestyle. Make the home truly yours by visiting our design studio, where you'll select finishes, fixtures, colors and other design details to add your own personal touches. Final sales price is dependent upon the design selections made. Don't miss this opportunity to create a home that is uniquely yours in one of Five Oaks' desirable golf-course homesites!

1153 Callaway Drive, Lebanon

$649,900

4 Beds ⋅ 4 Baths ⋅ 3318655 MLS ⋅ ACTIVE Status ⋅ 0.15 Acres ⋅ 37087 Zip Code

GOLF COURSE HOMESITE! Ask about how your rate can be as low as $4.5% for the first year! Sellers offering $10,000 towards a rate buydown with the use of preferred lender! Welcome to 1089 Callaway Drive, 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

$614,990

5 Beds ⋅ 3 Baths ⋅ 3298513 MLS ⋅ ACTIVE Status ⋅ 37087 Zip Code

Five Oaks Golf and Country Club. GENEROUS BUILDER INCENTIVE w/ preferred lender and title. Purchase a David Weekley Quick Move-in Home in the Nashville-area community of The Preserve at Five Oaks and receive either a complimentary Social Club Membership worth $5,000, or a $5,000 credit toward a Golf Club Membership at The Club at Five Oaks. The Satinwood floorplan has everything you need on the main floor. Chef's kitchen, study, owner's retreat featuring a separate tub and shower. This Satinwood also has a 5th Bedroom and 3rd Full Bath on the first floor! Upstairs are three spacious bedrooms, walk in closets, and loft space for family evenings. Professionally designed with classic finishes. Visit our model at 1077 Callaway Drive, Lebanon.

1096 Callaway Drive, Lebanon

$564,990

4 Beds ⋅ 4 Baths ⋅ 3298511 MLS ⋅ ACTIVE Status ⋅ 37087 Zip Code

Five Oaks Golf and Country Club! 4.99% INTEREST RATE w/ preferred lender and title. Plus purchase a David Weekley home in The Preserve at Five Oaks and receive either a complimentary Social Club Membership worth $5,000, or a $5,000 credit toward a Golf Club Membership at The Club at Five Oaks. Popular Gladstone Plan with main floor owner's suite!

1104 Callaway Drive, Lebanon

$245,000

3189493 MLS ⋅ ACTIVE Status ⋅ 0.053 Acres ⋅ 37087 Zip Code

1150 Callaway Dr, Lebanon

Start Your Search

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.