Courtside @ Southern Woods Homes for Sale

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

Life in Courtside @ Southern Woods means enjoying beautifully designed homes that reflect both style and functionality. Each residence boasts spacious floor plans, contemporary finishes, and lush landscaping that enhances the neighborhood's appeal. With homes for sale in this sought-after area, prospective buyers can find a range of options to suit their lifestyle and budget.

One of the standout features of Courtside @ Southern Woods is its prime location. Residents are just minutes away from Brentwood's vibrant shopping centers, gourmet dining options, and recreational facilities. The community is also within close proximity to top-rated schools, making it an excellent choice for families seeking quality education for their children. For those who enjoy the outdoors, numerous parks and green spaces are nearby, perfect for weekend picnics or leisurely strolls.

In addition to its picturesque surroundings, Courtside @ Southern Woods fosters a strong sense of community. Neighbors often come together for social events and activities, creating lasting friendships and a welcoming atmosphere.

If you’re looking for a beautiful home in a thriving community, Courtside @ Southern Woods in Brentwood, TN, is the perfect place to call home. Explore the available homes for sale today and discover the charm and convenience this exceptional subdivision has to offer!

Newest Courtside @ Southern Woods Homes for Sale

$950,000

4 Beds ⋅ 4 Baths ⋅ 3620735 MLS ⋅ ACTIVE Status ⋅ 0.24 Acres ⋅ 37027 Zip Code

With AAA Brentwood school zoning this all brick home backs up to tranquility and offers a flexible floorplan for today's needs! The oversized main level primary suite is highlighted by it's bay window view and accented with custom tray ceiling lights, the great room is bathed in natural light from tall picture windows while the soaring double high ceilings have skylights that offers more natural light, plus a cozy fireplace. The kitchen is tailored for effortless living, offers the opportunity to cook with gas and invites you to invite company with it's roomy eat in area and access to the back deck. Just off the entryway, double French doors open to a dedicated home office or formal living room and a formal dining room. Upstairs you'll find a second full/guest suite with large walk in closet and access to extensive under roof storage, separated from 2 secondary bedrooms and a bonus room that suggests the expansive extra deep garage beneath it. Located minutes from dining, shopping, parks and with easy commuter access to Cool Springs and Nashville.

1324 Sweetwater Dr, Brentwood

$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. (**Sellers offering an allowance for this garage conversion!) 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

$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.

Courtside @ Southern Woods Homes for Sale

Newest Courtside @ Southern Woods Homes for Sale

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