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4 Beds
7 Baths
7,138 sqft

$2,599,000

27 Colonel Winstead Dr, Brentwood TN, 37027

Price per sqft$364.11
Built in2000
Property size7,138 sqft
Property typeResidential
Courtesy of Benchmark Realty, LLC, Danielle Keegan Listing Contact: 9493514787

Overview

Active

Listed Aug 21, 2026

Updated 6 days ago

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.

$17,291/mo

Est. mortgage payment based on a $2,599,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
3519030

Interior Features

Bedrooms
4
Bathrooms
7
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.85 Acres

Other Property Details

Taxes
$8,155
Tax Frequency
Annually
Association Fee Frequency
Monthly
Garage
Yes
Pets Allowed
Yes
55+/Senior Community
No

Listings courtesy of Middle Tennessee Regional Multiple Listing Service as distributed by MLS GRID

All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor The Milam Group shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Properties displayed may be listed or sold by various participants in the MLS.

Based on information submitted to the MLS GRID as of 2:37 PM UTC on 9/15/2026. 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.

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