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27 Colonel Winstead Dr
Brentwood, TN 37027
FOR SALE · Active
$2,599,000
$364 / Sqft
4
Beds
7
Baths
3
Garage
7,138
Sqft
0.85
Acres
MLS# 3519030
Cumulative Days on Market: 70 · Includes prior listings · Currently listed since 08/20/26 · Data provided by the MLS.

Property Description

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.

Property Highlights

Property Type
Residential
Property Sub Type
Single Family Residence
Bedrooms
4
Total Bathrooms
7
Living Area
7,138 Sqft
Price / Sqft
$364
Acres
0.85
Year Built
2000
Cumulative Days on Market
70

Location

City/Township
Brentwood
Subdivision
Governors Club The Ph 2
County
Williamson County TN

Property Details

Price
$2,599,000
Property Type
Residential
Property Sub Type
Single Family Residence

Building

Levels
Three Or More
Total Area
7,138 Sqft

Community

Local Schools

Elementary School
Crockett Elementary
Middle School
Woodland Middle School
High School
Ravenwood High School

Interior Features

Bedrooms and Bathrooms

Total Bathrooms
7
Full Bathrooms
4
1/2 Bathrooms
3
Bedrooms
4
Bedrooms on Main Level
1

Rooms and Basement

Basement Features
Finished, Unfinished

Area and Spaces

Living Area
7,138 Sqft
Above Grade Finished Area
5,509 Sqft
Below Grade Finished Area
1,629 Sqft

Appliances

Appliances
Built-In Electric Oven, Double Oven, Cooktop, Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer

Interior Features

Interior Features
Bookcases, Built-in Features, Ceiling Fan(s), Central Vacuum, Entrance Foyer, Extra Closets, High Ceilings, Pantry, Walk-In Closet(s), Wet Bar
Flooring
Carpet, Wood, Marble, Tile
Laundry Features
Electric Dryer Hookup, Washer Hookup
Security Features
Carbon Monoxide Detector(s), Security Gate, Security Guard, Security System, Smoke Detector(s)
Fireplace Features
Den, Family Room, Gas, Great Room, Living Room, Recreation Room

Heating and Cooling

Heating Features
Central
Has Fireplace
Yes
Fireplaces
6

Building Details

Construction

Year Built
2000
Foundations
Slab

Materials

Construction Materials
Brick, Hardboard Siding, Stucco
Roof
Shingle

Terms

Terms

Special Conditions
Standard
Cumulative Days on Market
70

Taxes

Tax

Tax (Annual)
$8,155

HOA

Has HOA
Yes
Association Fee
$462 /mo
Association Ammenities
Clubhouse, Fitness Center, Gated, Golf Course, Park, Playground, Pool, Sidewalks, Tennis Court(s), Underground Utilities, Trail(s)

Heating, Cooling & Utilities

Cooling Features
Ceiling Fan(s), Central Air

Utilities

Utilities
Water Available
Sewer
Public Sewer
Water Source
Public

Lot

Acres
0.85
Lot Size
0.85
Lot Dimensions
139 X 249

Exterior Features

Exterior Features
Balcony
Patio And Porch Features
Deck, Covered, Patio, Porch, Screened

Parking

Garage Capacity
3
Covered Spaces
3
Listed by Benchmark Realty, LLC, 9493514787
Listing Data last updated 10/30/2026 04:00 am
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Property History

2 days ago
Property information last updated
70 days ago
Status Active. This is the date the listing was placed on market.
Cumulative Days on Market: 70 days (includes prior listings) · Currently listed since August 20, 2026. Data provided by the MLS.

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