About 27 Colonel Winstead Dr, Brentwood, Tennessee, 37027
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.
Water Source : Public
Sewer Source : Public Sewer
Garage On Property.
3 Total Parking
Parking Features : Garage Door Opener, Garage Faces Side
3 Garage Spaces
3 Covered Spaces
Lot Size Source : Calculated from Plat
Property has a View :
Above Grade Finished Area : 5509Square Feet
Cooling in Property:
Cooling: Ceiling Fan(s), Central Air
Heating in Property:
Heating : Central
Construction Materials: Brick, Hardboard Siding, Stucco
Levels : Three Or More
Basement Description : Finished, Unfinished
Appliances : Built-In Electric Oven, Double Oven, Cooktop, Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
Documents Count : 5
Year Built Details : Existing
Water Source : Public
Sewer Source : Public Sewer
Garage On Property.
3 Total Parking
Parking Features : Garage Door Opener, Garage Faces Side
3 Garage Spaces
3 Covered Spaces
Lot Size Source : Calculated from Plat
Property has a View :
Above Grade Finished Area : 5509Square Feet
Cooling in Property:
Cooling: Ceiling Fan(s), Central Air
Heating in Property:
Heating : Central
Construction Materials: Brick, Hardboard Siding, Stucco
Levels : Three Or More
Basement Description : Finished, Unfinished
Appliances : Built-In Electric Oven, Double Oven, Cooktop, Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
Documents Count : 5
Year Built Details : Existing

Street Address: 27 Colonel Winstead Dr
City: Brentwood
State: Tennessee
Postal Code: 37027
County: Williamson
Directions: I65 South, exit East on Concord Road - go to the Concord Road gated entrance of the Governors Club. Turn left on Governors Way at the first stop sign, and take it to Colonel Winstead Drive. Turn right, and go up the hill and the house is on your right.

Property Information :
Listing Status: Pending Sale
Size: 7,138 Sqft
Lot Size: 0.85 Acres
MLS #: 3519030
Bedrooms: 4 bd
Bathrooms: 5.5 ba
Price: $2,599,000
Tax Amount: 8155
Construction Status: Built in 2000
Last Modified : Nov 14 2026 2:12AM

Courtesy of: Danielle Keegan, Benchmark Realty, LLC (MLS# RTC3773)
Source MLS: Realtracs
Based on information submitted to the MLS GRID as of 11/14/2026 10:45:04 AM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.