Five Oaks Homes with Lebanon High School

Welcome to Five Oaks, an enchanting subdivision nestled in the heart of Lebanon, Tennessee, within the picturesque Wilson County. This charming community is a hidden gem that offers a perfect blend of tranquility and modern living, making it an ideal choice for families, professionals, and retirees alike.

Five Oaks boasts a stunning array of homes that cater to various tastes and lifestyles. From exquisite single-family residences to cozy townhomes, each property is thoughtfully designed with quality craftsmanship and attention to detail. With lush landscaping and meticulously maintained common areas, residents can enjoy a serene environment that feels like a retreat right at home.

One of the standout features of Five Oaks is its proximity to Lebanon High School, making it an attractive option for families with school-aged children. This well-regarded institution is just a stone's throw away, offering students a top-notch education and a range of extracurricular activities. Parents can rest easy knowing that their children are receiving a quality education within a supportive community.

In addition to its educational offerings, Five Oaks is conveniently located near local amenities, including shopping centers, restaurants, and parks. Residents can enjoy easy access to the vibrant downtown area of Lebanon, where they can explore charming boutiques and savor delicious cuisine.

Whether you’re looking for a peaceful retreat or a vibrant community, Five Oaks is the perfect place to call home. Experience the charm of Lebanon, TN, and discover the lifestyle you’ve always dreamed of in this exceptional subdivision. Come and explore Five Oaks today!

Newest Five Oaks Homes with Lebanon High School

$975,000

3 Beds ⋅ 4 Baths ⋅ 3623461 MLS ⋅ ACTIVE Status ⋅ 0.45 Acres ⋅ 37087 Zip Code

Beautifully updated home ideally situated along a scenic golf fairway. This spacious residence combines comfort and style with thoughtful updates throughout, including a remodeled primary and secondary bathrooms, new carpeting, upgraded major appliances and mechanical systems, and crawlspace encapsulation. Enjoy generous living spaces, modern conveniences, and a picturesque setting that offers a unique blend of elegance and golf course living. Move-in ready and designed for effortless enjoyment, this home is an exceptional opportunity to experience the best of fairway living.

601 Ridgecrest Ln, Lebanon

$724,990

4 Beds ⋅ 4 Baths ⋅ 3622438 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 Dr, Lebanon

$704,990

4 Beds ⋅ 3 Baths ⋅ 3622437 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 Dr, Lebanon

$609,990

5 Beds ⋅ 3 Baths ⋅ 3621917 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 Dr, Lebanon

$549,990

4 Beds ⋅ 4 Baths ⋅ 3621833 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 Dr, Lebanon

$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.

Five Oaks Homes with Lebanon High School

Newest Five Oaks Homes with Lebanon High School

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