Five Oaks Homes with Trail(s) Community Features

Welcome to Five Oaks, a stunning subdivision nestled in the heart of Lebanon, Tennessee, within the picturesque Wilson County. This vibrant community offers the perfect blend of serene living and modern convenience, making it an ideal choice for families, professionals, and retirees alike.

Five Oaks is renowned for its beautifully designed homes that cater to a variety of lifestyles. Whether you’re looking for a cozy single-family residence or a spacious estate, this neighborhood has something to suit your needs. The homes are characterized by their elegant architecture and thoughtful layouts, providing ample space for both relaxation and entertainment.

One of the standout features of Five Oaks is its commitment to outdoor living. The community boasts an extensive network of trails, perfect for walking, jogging, or biking. These scenic paths wind through lush greenery, offering residents a chance to connect with nature right outside their door. Imagine leisurely strolls with family, morning runs, or weekend bike rides, all within the safety and beauty of your neighborhood.

In addition to the trails, Five Oaks offers a host of community amenities that enhance the overall living experience. Residents can enjoy access to parks, playgrounds, and recreational facilities, fostering a strong sense of community and encouraging an active lifestyle.

With its prime location in Lebanon, Five Oaks provides easy access to shopping, dining, and entertainment options, ensuring that everything you need is just a short drive away. Experience the charm and convenience of Five Oaks—where your dream home awaits!

Newest Five Oaks Homes with Trail(s) Community Features

$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

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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.