Courtside @ Southern Woods Real Estate

Welcome to Courtside @ Southern Woods, a hidden gem nestled in the heart of Brentwood, Tennessee, within the picturesque Williamson County. This charming subdivision offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, professionals, and retirees alike.

As you enter Courtside, you’ll be greeted by beautifully landscaped streets lined with elegant homes, each exuding a unique character while maintaining a cohesive aesthetic. The neighborhood is designed with community in mind, featuring well-maintained sidewalks, inviting green spaces, and friendly neighbors who take pride in their homes.

Residents of Courtside @ Southern Woods enjoy easy access to top-rated schools, including Brentwood High School and Scales Elementary, ensuring that education is a top priority for families. The subdivision is also conveniently located near a variety of shopping, dining, and recreational options. Whether you're in the mood for a casual bite at a local café or an upscale dining experience, Brentwood has it all.

Outdoor enthusiasts will appreciate the proximity to several parks and nature trails, perfect for weekend adventures or evening strolls. Additionally, the vibrant city of Nashville is just a short drive away, offering a rich cultural scene, live music, and endless entertainment options.

Discover the charm and convenience of Courtside @ Southern Woods, where community spirit meets modern living. Your dream home awaits in this idyllic Brentwood neighborhood!

Newest Listings in Courtside @ Southern Woods

$835,000

4 Beds ⋅ 3 Baths ⋅ 3598112 MLS ⋅ ACTIVE Status ⋅ 0.26 Acres ⋅ 37027 Zip Code

Lovely home in a great community. Two Story foyer entrance and spacious primary bedroom on the main level. Huge bonus/media room upstairs. All new carpets throughout. Deck newly stained. Backyard is fully fenced & overlooks a mature tree line. Zoned for top rated Brentwood schools. Close to shops, restaurants and Interstate and all that Brentwood has to offer. Award winning library and newly renovated YMCA nearby.

1465 Red Oak Dr, Brentwood

$950,000

5 Beds ⋅ 3 Baths ⋅ 3602830 MLS ⋅ ACTIVE Status ⋅ 0.25 Acres ⋅ 37027 Zip Code

With its welcoming grand entryway, high ceilings, and abundant natural light, this Brentwood home sets an inviting tone in the established neighborhood of Courtside at Southern Woods. The main level balances tradition and comfort with both a formal sitting room and a formal dining room accented by classic millwork. In the heart of the home, a dramatic great room anchors the space with a central fireplace, while newly refinished hardwood floors flow into the kitchen. Outfitted with granite countertops, stainless double ovens, and a breakfast bar, the kitchen opens to a sunlit eat-in dining area as expansive as the kitchen itself—creating the perfect spot to start your morning while taking in peaceful views of the tree-lined backyard. Main-level living shines with a sprawling primary suite designed as a private retreat, distinguished by a massive walk-in closet and a generously sized bathroom complete with dual vanities, a soaking tub, and a tiled shower. Also on the main floor is a substantial bonus room that adds valuable flex space, with the potential to easily be converted back into a garage. Upstairs, four additional bedrooms are all impressively large, ensuring everyone has plenty of space of their own. Outdoors, the backyard oasis features a newly updated, expansive deck—the perfect setting for al fresco dining or relaxing under the Tennessee canopy. Beyond the property, Courtside at Southern Woods offers a community pool, tennis court, park, and playground. The location keeps local Brentwood favorites close at hand—from Crema Coffee Roasters and Puffy Muffin to top shopping and dining at Hill Center Brentwood, with Cool Springs and McEwen Northside offering even more options nearby. Spanning over 4,000 square feet, this home brings together architectural volume, flexible gathering spaces, outdoor living, and an amenity-rich community into one cohesive, inviting setting.

1304 Sweetwater Dr, Brentwood

$859,000

4 Beds ⋅ 3 Baths ⋅ 3513370 MLS ⋅ ACTIVE Status ⋅ 0.24 Acres ⋅ 37027 Zip Code

Seller will consider owner financing with 40% downpayment. This property previously went under contract at $884,900. The sale did not close becuase the buyer was unable to sell their home. Immaculate, light-filled, and truly move-in ready, this beautifully maintained 4-bedroom, 3-bath home offers an exceptional combination of space, comfort, and convenience in the heart of Brentwood. The thoughtfully designed floor plan features two bedrooms and two full baths on the main level, including a spacious primary suite—providing flexibility and easy everyday living. At the heart of the home, the bright white kitchen features granite countertops and flows seamlessly into the main living spaces, where rich hardwood floors and abundant natural light create a warm, inviting atmosphere. Upstairs, you'll find two additional bedrooms along with a generously sized bonus room that's perfect for a media room, playroom, home office, or additional gathering space. The standout feature is the incredible 30' x 15' screened-in porch with a fireplace—an impressive outdoor living space designed to be enjoyed throughout the year. Just beyond, a second patio and fully fenced backyard offer plenty of room for entertaining, pets, and play, while mature woods provide a peaceful, private backdrop. A two-car garage, generous storage, and a quiet setting add even more to this home's appeal. With a versatile floor plan, beautiful indoor and outdoor living spaces, and a sought-after Brentwood location, this home has so much to offer. Schedule your private showing today!

106 Buckhead Ct, Brentwood

$1,249,900

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

New Price! 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 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. The fully finished walk-out basement offers incredible flexibility for a studio, home-based business, 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 love Marcella Vivrette Smith Park, Crockett Park. 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

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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.