Five Oaks Homes with Sidewalks Community Features

Welcome to Five Oaks, a charming subdivision nestled in the heart of Lebanon, Tennessee, in beautiful Wilson County. This picturesque community is designed for those who cherish both tranquility and connection, making it the perfect place to call home. With its friendly atmosphere and stunning landscapes, Five Oaks offers a unique blend of suburban comfort and natural beauty.

One of the standout features of Five Oaks is its commitment to community living, highlighted by the well-maintained sidewalks that wind through the neighborhood. These inviting pathways encourage residents to enjoy leisurely strolls, morning jogs, or family bike rides while soaking in the serene surroundings. The sidewalks not only promote an active lifestyle but also foster a sense of camaraderie among neighbors, making it easy to connect with others in the community.

The homes in Five Oaks are thoughtfully designed, offering a variety of styles and sizes to meet the needs of every family. Whether you’re a first-time homebuyer or looking to upgrade, you’ll find options that suit your lifestyle and budget. Many residences feature spacious yards, modern amenities, and beautiful architectural details that enhance the neighborhood's charm.

In addition to its beautiful homes, Five Oaks is conveniently located near shopping, dining, and recreational opportunities, ensuring that residents have everything they need right at their fingertips. With its blend of community spirit, beautiful homes, and a welcoming atmosphere, Five Oaks is truly a hidden gem in Lebanon, TN. Come discover your dream home in this vibrant and inviting community!

Newest Five Oaks Homes with Sidewalks Community Features

$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

$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

$574,990

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

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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.