Courtside @ Southern Woods Homes with Brentwood High School

Welcome to Courtside @ Southern Woods, a charming subdivision nestled in the heart of Brentwood, TN, in beautiful Williamson County. This sought-after community offers a perfect blend of convenience and tranquility, making it an ideal place to call home.

Courtside @ Southern Woods is renowned for its picturesque surroundings, well-maintained streets, and friendly atmosphere. Residents here enjoy the best of both worlds - a peaceful suburban lifestyle with easy access to all the amenities and attractions that Brentwood has to offer.

One of the standout features of this subdivision is its proximity to Brentwood High School, making it a popular choice for families with school-age children. The top-rated school provides residents with excellent educational opportunities and a strong sense of community.

Homes in Courtside @ Southern Woods are designed to cater to a variety of lifestyles, with spacious layouts, modern amenities, and beautiful finishes. Whether you're looking for a cozy starter home or a luxurious estate, you're sure to find the perfect property to suit your needs in this lovely neighborhood.

Come and experience the beauty and charm of Courtside @ Southern Woods - where quality living meets small-town charm in the heart of Brentwood, TN.

Newest Courtside @ Southern Woods Homes with Brentwood High School

$1,299,000

4 Beds ⋅ 5 Baths ⋅ 3288324 MLS ⋅ ACTIVE Status ⋅ 0.23 Acres ⋅ 37027 Zip Code

Welcome to 1487 Red Oak Drive—a beautifully maintained home tucked among mature trees in one of Brentwood's most desirable communities, offering exceptional living space, privacy, and a thoughtfully designed floor plan. Freshly painted throughout, this home welcomes you with a dedicated front office with a private entrance, an elegant formal dining room, and a spacious great room featuring soaring ceilings, a cozy fireplace, and dramatic windows that fill the home with natural light while showcasing peaceful views of the tree-lined backyard. The heart of the home is the open-concept kitchen featuring corian countertops, abundant cabinetry, a large pantry, and a sunny breakfast area that flows seamlessly into the main living space—perfect for both everyday living & entertaining. The spacious primary suite is conveniently located on the main level, providing comfort and privacy. Upstairs, you'll find two generously sized bedrooms, each with its own private en-suite bathroom. A spacious bonus room offers endless possibilities as a media room, playroom, or second family room, while additional walk-in storage makes staying organized effortless. Fully finished walk-out basement offers flexibility for multi-generational living, guests, or entertaining. The lower level includes a generous family room w/ a second fireplace, kitchenette,private bedroom, full bath, dedicated workout area, abundant storage, & direct access to the covered patio overlooking the private backyard. Outdoor living is equally inviting with both an upper deck and lower patio, each providing tranquil wooded views and exceptional privacy. A welcoming rocking chair front porch offers the perfect spot to enjoy your morning coffee. Residents enjoy access to the neighborhood pool & playground. Outdoor enthusiasts will appreciate nearby Marcella Vivrette Smith Park,Crockett Park&Deerwood Arboretum. Just 11 miles to Downtown Nashville, 13 miles to BNA airport, & 8 miles to Cool Springs Galleria...A Must See!

1487 Red Oak Dr, Brentwood

$874,900

4 Beds ⋅ 3 Baths ⋅ 3136913 MLS ⋅ ACTIVE Status ⋅ 0.24 Acres ⋅ 37027 Zip Code

Immaculate, sun-filled, and move-in ready, this beautifully maintained 4-bedroom, 3-bath home offers the perfect blend of comfort, space, and location in the heart of Brentwood. Thoughtfully designed with functional living in mind, the layout features two bedrooms and two full baths on the main level, including the spacious primary suite, making everyday living both convenient and accessible. The bright white kitchen with granite countertops flows seamlessly into the main living areas, highlighted by rich hardwood flooring and abundant natural light. Upstairs, you’ll find two additional bedrooms plus a large bonus room—ideal for a media room, playroom, or home office. Step outside to what truly sets this home apart: a show-stopping 30x15 screened-in porch with a fireplace, creating a year-round outdoor living space perfect for relaxing or entertaining. A second patio and fully fenced backyard with wooded privacy provide even more room for gatherings, pets, and play. Additional features include a two-car garage, generous storage, and a quiet setting in one of Brentwood’s most desirable locations. This home checks every box — space, style, and an unbeatable setting. Schedule your private showing today!

106 Buckhead Ct, Brentwood

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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.