Five Oaks Homes for Sale in Lebanon, TN

$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

$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

$819,900
3 Beds 3 Baths 3244345 MLS ACTIVE Status 0.43 Acres 37087 Zip Code
You’ll fall in love with this impeccably maintained, move-in ready home…quality craftsmanship, and an ideal floor plan in one of Lebanon’s most desirable golf communities. A grand 9' double brass entry door welcomes you into an elegant foyer highlighted by distinctive tray ceilings that continue into the dining area and luxurious primary suite. Beautiful hardwood floors flow throughout the main living areas and all bedrooms, complemented by tile flooring in the baths and timeless plantation shutters throughout the home. Designed for both everyday living and entertaining with a super-sized kitchen featuring granite countertops, loads of cabinetry, a double oven, and generous prep space, opening to a warm and inviting great room with a fireplace. Three oversized bedrooms, including the primary suite, are conveniently located on the main level, while the impressive 26’ x 27’ bonus room complete with full bath, huge closet and wet bar offering endless possibilities for a guest retreat, media room, game room, or home office. Step outside to enjoy the level, fully fenced backyard with irrigation in both the front and rear yards—perfect for entertaining, pets, or simply relaxing. Additional features include a three-car side-entry garage, water softener, attic TV antenna, and new tankless water heater, plus roof, gutters, and HVAC all recently replaced...reflecting the pride of ownership found throughout this exceptional home. Located in the highly sought-after Five Oaks community, where golf club membership is available but optional, this home offers the perfect blend of luxury, comfort, and convenience with easy access to shopping, dining, healthcare, and major commuter routes. If you’ve been waiting for a home that offers generous room sizes, thoughtful upgrades, impeccable recent updates (see attached list), excellent condition, and true move-in readiness, this is one you won’t want to miss.

402 Five Oaks Blvd, Lebanon

$450,000
2 Beds 2 Baths 3230671 MLS ACTIVE Status 0.25 Acres 37087 Zip Code
Experience refined one‑level living in the prestigious Five Oaks Golf Course community. This beautifully updated Arlington floorplan offers a seamless blend of comfort, style, and low‑maintenance living—ideal for anyone seeking an elevated lifestyle with modern finishes and thoughtful design. Step inside to an inviting open‑concept layout enhanced by plantation shutters, granite countertops, upgraded cabinetry, and designer lighting that adds warmth and sophistication throughout. The spacious kitchen features double ovens and flows effortlessly into the living and dining areas, creating an ideal setting for entertaining or relaxed everyday living. A private dedicated office provides valuable flexibility for work, hobbies, or quiet retreat. The primary suite includes a tray ceiling and a well‑appointed bath, while the second bedroom offers comfortable accommodations for guests. Enjoy year‑round outdoor living on the covered, screened‑in patio, perfect for morning coffee, evening unwinding, or hosting friends in a protected outdoor space. Located within the sought‑after Club at Five Oaks, residents who choose to join the club gain access to golf, pool, tennis, pickleball, dining, and beautifully maintained amenities—adding convenience and leisure right at your doorstep. This 2021 home combines modern construction, single‑level ease, and a premier community setting to deliver a lifestyle that feels both elevated and effortless.

1064 Callaway Dr, Lebanon

$535,000
3 Beds 3 Baths 3225596 MLS ACTIVE Status 0.13 Acres 37087 Zip Code
SHOWS LIKE A MODEL. LIVES LIKE NEW! If condition matters, put this one at the TOP of your Five Oaks list! Meticulously maintained, beautifully decorated and exceptionally lightly lived in, this 3BR/3BA, 2,327 sq ft home shows like a MODEL HOME. Previously under contract and back on the market due to the buyer's health circumstances—not an issue with the home. One of the best features is the floor plan. With 1,635 sq ft on the MAIN LEVEL, you can enjoy primarily one-level living without sacrificing the extra space you want. The main floor includes the primary suite, a second bedroom and full bath, open living and dining areas, and a beautiful kitchen with granite countertops. Hardwood floors, an inviting foyer, walk-in closets and a tiled primary shower add to the polished, move-in-ready feel. Need room for guests, hobbies, work or entertainment? The exceptionally lightly used upstairs provides 692 additional sq ft with a third bedroom, full bath, spacious rec room AND a 12x21 media/flex room. It's the best of both worlds—everything you need for daily living downstairs with an entire upstairs available when you want it. Enjoy your covered patio and the convenience of low-maintenance living, plus an attached 2-car garage, irrigation system, energy-efficient windows, programmable thermostat and natural gas heat. Washer, dryer and refrigerator remain. Located in the desirable Five Oaks golf course community, convenient to shopping, dining and I-40.

1010 Callaway Dr, Lebanon

$899,990
4 Beds 4 Baths 3205410 MLS ACTIVE Status 0.42 Acres 37087 Zip Code
Welcome to Five Oaks living at its finest, where elevated design, peaceful golf course views, and over 4,000 square feet come together in one unforgettable Lebanon home. This 4 bedroom, 3.5 bath residence offers a refined yet comfortable layout with beautiful natural light, wall-to-wall tile flooring on the main level, and a seamless flow designed for everyday living and effortless entertaining. The kitchen is the heart of the home, featuring custom Vadara quartz countertops with a full-height matching backsplash, a striking waterfall island, sleek black granite sink, custom white shaker cabinetry, a custom-built range hood, GE Profile appliances, a built-in Tylza dual-zone beverage cooler, layered lighting, and a professional-grade Wolf range. The living room delivers a stunning first impression with expansive windows, remote-controlled smart blinds, a dramatic crystal chandelier, and a custom gas/wood-burning fireplace wrapped in bold floor-to-ceiling black and gray stone tile. Enjoy peaceful mornings in the sitting room with coffee, sunrise views, mature trees, birds, distant golf course scenery, and a pond backdrop that creates a calm, countryside feel. The bonus room offers a truly unique retreat, inspired by European galleries with architectural character, soft natural light, and a serene atmosphere unlike the rest of the home. As the day shifts into evening, statement chandeliers and layered lighting transform the home into a warm, intimate setting perfect for relaxing, hosting, or enjoying a quiet night in. Located on the golf course in the desirable Five Oaks community, this home offers a rare connection to nature while still being close to Lebanon conveniences, shopping, dining, and commuter routes. As an added bonus, basic lawn maintenance is included for the remainder of the year, including turf care, weed eating, edging sidewalks, driveway and mulch beds, plus blowing debris from sidewalks, patios, and driveways until seasonal mowing ends in the fall.

425 Ridgecrest Ln, Lebanon

$949,900
4 Beds 5 Baths 3178969 MLS ACTIVE Status 0.42 Acres 37087 Zip Code
Welcome to 548 Ridgecrest Ln in Lebanon! Are you looking for a move-in ready home offering modern upgrades, energy efficiency, and smart home features in a desirable location? This well-maintained property features a spacious open layout, ideal for both everyday living and entertaining. The home is beautifully appointed with quartz countertops throughout, adding a sleek, durable, and upscale finish to the kitchen and bathrooms. Enjoy improved indoor comfort with advanced air quality systems, including a whole-home humidifier, HVAC UV light, and electrostatic air filtration—perfect for buyers seeking a healthy home, allergy-friendly environment, and clean air living. The home includes updated bathrooms with upgraded tile, glass shower surrounds, and a bidet, delivering a luxury feel at an affordable price point. Additional highlights include a central vacuum system and a complete appliance package, featuring a newer washer and dryer, making this a true turnkey home. Major systems have already been updated, including a roof and HVAC system less than three years old, tankless water heater, providing peace of mind and reducing future maintenance costs. Buyers will appreciate features such as low-maintenance living, upgraded systems, and move-in ready condition, reducing immediate out-of-pocket costs. Ideal for first-time homebuyers, relocating buyers, or those seeking upgraded resale homes. Conveniently located near shopping, dining, and commuter routes, this home offers the perfect blend of comfort, convenience, and modern living. Key Features: Quartz countertops • Newer roof & HVAC (<3 yrs) • Move-in ready • Updated bathrooms • Air quality upgrades • Central vacuum • Newer washer & dryer • Turnkey • Low maintenance • Desirable location Schedule your showing today—homes with these upgrades and features don’t last long!

548 Ridgecrest Ln, Lebanon

$3,900,000
5 Beds 7 Baths 3169407 MLS ACTIVE Status 2.2800000000000002 Acres 37087 Zip Code
Collector-Car Dream on the Golf Course — Basement Garage Holds 8–10 Cars! Experience unrivaled luxury and car-collector convenience in prestigious Five Oaks. Custom-built by a respected local builder, this executive estate sits on 2.3 private acres overlooking the golf course and offers ~12,517 sq ft of impeccably finished living space. The temperature-controlled, fully finished basement garage is a standout — engineered to house 8–10 vehicles with room for a workshop, display lighting, and secure storage, plus a built-in safe room for added peace of mind. 2 elegant primary suites (one main level, one upstairs) and 3 additional bedrooms, 4 full baths, 3 ½ baths provide flexible living. The main-level primary suite offers a spa-like retreat with a steam tile shower, soaking tub, double vanities, a separate makeup vanity, and expansive His & Her walk-in closets with built-in cabinetry. The gourmet kitchen is a true showpiece with glazed cabinetry, exquisite calcutta marble countertops, a gas cooktop with pot filler, double ovens, two built-in Sub-Zero refrigerators, 2 dishwashers, a large pantry, and a wood-topped island. Entertain effortlessly with formal dining, complemented by a well-appointed butler’s pantry with granite and an ice maker; Outdoor living is unmatched with screened porch, a covered back porch with beadboard ceiling, and a pergola with golf-course views perfect for relaxing or entertaining. Exceptional finishes include crown molding, coffered wood-beam ceilings in the office, whole-home audio (outdoors included), two gas-log fireplaces, a wood-burning fireplace with a gas starter, a central vacuum, a hobby room, and a large laundry room with a convenient laundry shute. Built for longevity and efficiency with a 50-year roof, copper gutters, and four HVAC units. Convenient to I-40, I-840, Hwy 109, and just 20 minutes to Nashville International Airport. Ideal for discerning buyers seeking luxury living and a professional-grade car collection home.

517 Ridgecrest Ln, Lebanon

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