Five Oaks Real Estate

Welcome to Five Oaks, a picturesque subdivision nestled in the heart of Lebanon, Tennessee, within the vibrant Wilson County. This charming community is perfect for families, retirees, and anyone seeking a tranquil lifestyle while still being close to the bustling amenities of city life.

Five Oaks boasts a variety of beautifully designed homes that cater to diverse tastes and preferences. From modern architectural styles to classic designs, each residence is crafted with attention to detail and quality. The neighborhood is adorned with lush green spaces, manicured lawns, and tree-lined streets, creating an inviting atmosphere that encourages outdoor living and community interaction.

One of the standout features of Five Oaks is its proximity to top-notch schools, making it an ideal choice for families. Residents enjoy easy access to educational institutions that are known for their commitment to excellence in academics and extracurricular activities. Additionally, the community is conveniently located near shopping centers, restaurants, and recreational facilities, ensuring that everything you need is just a stone's throw away.

For outdoor enthusiasts, Five Oaks offers ample opportunities for exploration and leisure. With nearby parks, walking trails, and scenic spots, residents can indulge in a variety of activities, from hiking to picnicking. The community also hosts regular events and gatherings, fostering a sense of camaraderie among neighbors.

In Five Oaks, you’ll find not just a home, but a lifestyle. Experience the perfect blend of suburban charm and modern convenience in this delightful Lebanon community. Come discover your dream home today!

Newest Listings in Five Oaks

$644,990

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

GOLF COURSE HOMESITE! Ask about how your rate can be as low as 5% for the first year! 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

$199,000

2 Beds ⋅ 2 Baths ⋅ 3546683 MLS ⋅ ACTIVE Status ⋅ 0.01 Acres ⋅ 37217 Zip Code

Affordable Living in the Heart of Nashville! Welcome to 129 Five Oaks Dr, nestled in the desirable Five Oaks Condo community. This charming 2-bedroom, 1.5-bath condo offers an exceptional combination of comfort, convenience, and affordability. Ideally located just 10 minutes from Nashville International Airport, this home provides easy access to downtown Nashville, major highways, shopping, dining, and entertainment—making it a great choice for homeowners, traveling professionals, and investors alike. Priced to sell, this property presents an incredible opportunity for first-time homebuyers, those looking to downsize, or anyone seeking an affordable home in Nashville's competitive market. Even better, there are no rental restrictions, offering flexibility for both long-term and short-term rental opportunities (buyers should verify all local regulations). Whether you're searching for your next home or a smart investment property, this condo delivers outstanding value in a highly desirable location. Don't miss your opportunity to own in the sought-after Five Oaks community—schedule your private tour today!

129 Five Oaks Dr, Nashville

$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

$235,000

2 Beds ⋅ 1 Baths ⋅ 3318803 MLS ⋅ ACTIVE Status ⋅ 0.02 Acres ⋅ 37217 Zip Code

Adorable DETACHED condo! 2 bedrooms, 1 bathroom, complete with a cute little porch and deck. Perfect for first time home buyers, or buyers looking to downsize. Home also offers the most convenient central location, easy access to BNA, Downtown, I-40, 440, I-24.

102 Five Oaks Dr, Nashville

$234,000

2 Beds ⋅ 1 Baths ⋅ 3305881 MLS ⋅ ACTIVE Status ⋅ 0.02 Acres ⋅ 37217 Zip Code

This beautifully refreshed home is back on the market with impressive updates throughout! Enjoy brand-new laminate flooring, custom closet shelving, new interior doors, a new dishwasher, and a tastefully remodeled bathroom that adds a modern touch. Step outside to the spacious deck perfect for relaxing evenings, entertaining friends, or enjoying your morning coffee.Conveniently located just minutes from downtown Nashville, Opry Mills, and BNA Airport, you’ll have easy access to shopping, dining, entertainment, and major commuter routes.Don’t miss your opportunity to see this move-in-ready home with its fresh updates and fantastic location!

126 Five Oaks Dr, Nashville

$234,900

2 Beds ⋅ 3 Baths ⋅ 3305564 MLS ⋅ ACTIVE Status ⋅ 0.01 Acres ⋅ 37217 Zip Code

Move-in ready 2-bedroom, 3-bath townhouse offering 1,216 square feet in a convenient East Nashville location. Extensively updated in 2019 with new laminate flooring, a remodeled kitchen and bathrooms, and a new bathtub, this home also features a new HVAC system installed in 2024 and a new dishwasher. The functional floor plan provides spacious living areas, while two assigned parking spaces add everyday convenience. Located in a quiet community just minutes from Percy Priest Lake, Nashville International Airport (BNA), and Downtown Nashville, this home offers an excellent opportunity for first-time buyers, investors, or anyone seeking low-maintenance living with easy access to shopping, dining, parks, and major commuter routes. The HOA includes common area maintenance, making for a carefree lifestyle in a highly desirable location.

211 Oak Grove Dr, Nashville

$609,990

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

$549,990

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

$237,500

2 Beds ⋅ 2 Baths ⋅ 3158549 MLS ⋅ ACTIVE Status ⋅ 0.02 Acres ⋅ 37217 Zip Code

Beautiful one-level renovated turnkey townhome within 10-12 minutes to downtown. Central to everything, end Unit. Low HOA fees at $160. 2 Bedrooms, 2 half and one full bathroom. Roof, HVAC, Foundation, plumbing in good shape and has been updated. Park-like setting and an unbeatable price!

213 Oak Grove Dr, Nashville

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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.