27 Colonel Winstead Dr, Brentwood, TN

$2,599,000

Previous Next
  • 4

    Beds

  • Baths

  • 7,138

    Square feet

  • 0.85

    Acres

Description of 27 Colonel Winstead Dr, Brentwood - MLS# 3519030

Set beneath a canopy of mature trees in the prestigious, guard-gated Governors Club, this beautifully maintained estate offers timeless Southern character, gracious living spaces, and an exceptional opportunity to create something truly special. A sweeping front porch sets the tone, overlooking the picturesque golf course and offering the kind of setting made for quiet mornings, evening conversations, and an unhurried way of life. Inside, more than 7,000 square feet unfolds across a warm, traditional floor plan with generous room sizes, abundant natural light, and beautiful architectural detail throughout. The main-level primary suite provides a private retreat, while multiple living and gathering spaces offer an effortless backdrop for both everyday life and entertaining. Upstairs, a spacious bonus room provides wonderful flexibility, and the finished basement expands the possibilities even further with room for entertaining, recreation, fitness, guests, or hobbies. With four generously sized bedrooms, four full baths, and three half baths, the home has been exceptionally well cared for and offers a wonderful foundation for its next chapter. Move in and enjoy its classic warmth as it is, or thoughtfully update over time to create a home uniquely your own. Outside, the mature landscape and beautiful treed homesite create a sense of privacy and permanence that is increasingly difficult to find. And within Governors Club, residents enjoy a coveted lifestyle centered around championship golf, clubhouse dining, fitness, resort-style pools, tennis, and an active social community. Timeless architecture, remarkable space, and an irreplaceable setting come together in a home filled with possibility—an exceptional opportunity to make your mark within one of Middle Tennessee’s most sought-after communities.

Features of 27 Colonel Winstead Dr of 27 Colonel Winstead Dr

MLS® # 3519030
Price $2,599,000
Bedrooms 4
Bedrooms on Main 1
Bathrooms 5.50
Full Baths 4
Half Baths 3
Square Footage 7,138
Acres 0.85
Year Built 2000
Type Residential
Sub-Type Single Family Residence
Status Active
New Construction No

Community Information : Brentwood

Address 27 Colonel Winstead Dr
Subdivision Governors Club The Ph 2
City Brentwood
County Williamson County, TN
State TN
Zip Code 37027

Amenities of 27 Colonel Winstead Dr

Amenities Clubhouse, Fitness Center, Gated, Golf Course, Park, Playground, Pool, Sidewalks, Tennis Court(s), Underground Utilities, Trail(s)
Utilities Water Available
Parking Spaces 3
# of Garages 3
Garages Garage Door Opener, Garage Faces Side
Is Waterfront No
Has Pool No

Interior of 27 Colonel Winstead Dr

Interior Features Bookcases, Built-in Features, Ceiling Fan(s), Central Vacuum, Entrance Foyer, Extra Closets, High Ceilings, Pantry, Walk-In Closet(s), Wet Bar
Appliances Built-In Electric Oven, Double Oven, Cooktop, Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
Heating Central
Cooling Ceiling Fan(s), Central Air
Fireplace Yes
# of Fireplaces 6
# of Stories 3
Basement Finished, Unfinished

Exterior of 27 Colonel Winstead Dr

Exterior Features Balcony
Roof Shingle
Construction Brick, Hardboard Siding, Stucco

School Information of 27 Colonel Winstead Dr

Elementary Crockett Elementary
Middle Woodland Middle School
High Ravenwood High School

Additional Information On 27 Colonel Winstead Dr

Date Listed August 21st, 2026
Days on Market 18
Foreclosure No
Short Sale No

Listing Details of 27 Colonel Winstead Dr

OfficeBenchmark Realty, LLC

Listings courtesy of REALTRACS as distributed by MLS GRID

Listing Map of 27 Colonel Winstead Dr

Request a Showing

27 Colonel Winstead Dr Brentwood TN 37027 - MLS# 3519030

Provide a valid email address.
When would you like to view this property?