27 Colonel Winstead Dr

Brentwood, TN
$ 2,599,000 Beds 4 Baths 5.5 Sq 7,138
Monthly Estimate* How much can I afford?

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.

Active

  • Price
  • $ 2,599,000
  • City
  • Brentwood
  • Bedrooms
  • 4
  • Full Bathrooms
  • 4
  • County
  • WILLIAMSON
  • Half Bathrooms
  • 3
  • Area
  • Lot Size
  • 0.85 Acres
  • Zip
  • 37027
  • Sqr Footage
  • 7,138
  • Year Built
  • 2000
  • Taxes
  • $ 8155
  • Style
  • MLS#
  • 3519030
Listed By: Benchmark Realty, LLC;
Data Source: Listing courtesy of RealTracs MLS as distributed by MLS GRID

Features

General

Living Area 7138
Sewer Public Sewer
Heating Central
Cooling Ceiling Fan(s),Central Air
Utilities Water Available
Possession Close Of Escrow
Roof Shingle
Appliances Built-In Electric Oven,Double Oven,Cooktop,Dishwasher,Disposal,Dryer,Ice Maker,Microwave,Refrigerator,Stainless Steel Appliance(s),Washer
HOA Fee 462
Garage Spaces 3
Patio/Porch Features Deck,Covered,Patio,Porch,Screened
Security Features Carbon Monoxide Detector(s),Security Gate,Security Guard,Security System,Smoke Detector(s)
Construction Materials Brick,Hardboard Siding,Stucco
Pets Allowed Yes
Year Built 2000
Stories Count 3
Levels Three Or More
Property Subtype Single Family Residence
Assoc Fee Paid Per Monthly
County Williamson County,TN
New Construction No
Property Type Residential
Association Amenities Clubhouse,Fitness Center,Gated,Golf Course,Park,Playground,Pool,Sidewalks,Tennis Court(s),Underground Utilities,Trail(s)
Attached Garage No
Subdivision Name Governors Club The Ph 2
Garage Y/N Yes
Full Baths 4
Status Active
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,
High School Ravenwood High School
City Brentwood
Senior Community Y/N No
Lot Size Units Acres
Elementary School Crockett Elementary
Property Attached Y/N No
Year Built Details Existing
Tax Annual Amount 8155
Middle/Junior High School Woodland Middle School
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active

Interior Features

Interior Amenities Bookcases,Built-in Features,Ceiling Fan(s),Central Vacuum,Entrance Foyer,Extra Closets,High Ceilings,Pantry,Walk-In Closet(s),Wet Bar
Basement Finished,Unfinished
Flooring Carpet,Wood,Marble,Tile
Total Fireplaces 6
Air Conditioning Y/N Yes
Heating Y/N Yes
Fireplace Y/N Yes
Above Grade Finished Area 5509
Half Baths 3
Laundry Features Electric Dryer Hookup,Washer Hookup
Total Bedrooms 4
Below Grade Finished Area 1629
Main Level Bedrooms 1
Below Grade Finished Area Unit Type Square Feet
LivingAreaSource Owner
Below Grade Finished Area Source Owner
Above Grade Finished Area Source Owner
Above Grade Finished Area Unit Type Square Feet
Total Baths 7

Exterior Features

Exterior Amenities Balcony
Parking Features Garage Door Opener,Garage Faces Side
Water Source Public
Total Parking 3
Lot Size Area 0.85
Building Area Total 7138
Lot Dimensions 139 X 249
Lot Size Acres 0.85
Lot Size Source Calculated from Plat
Waterfront Y/N No
Covered Spaces 3
Other Equipment Irrigation System

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the FAIRVIEW, TN office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

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

Price History

8/20/2026 Listed $2,599,000

Property vs Zip Code Average in 37027

Price
AVG $2.61M
$2.6M
Taxes
AVG $7,015
$8,155
Year Built
AVG 2006
2000
Visits
AVG 85
31
Data Provided by Inside Real Estate®

27 Colonel Winstead Dr Brentwood, TN is a Single Family Home for sale at $2599000 with 7138 sqft and a lot size of 0.85 Acres Acre(s). 27 Colonel Winstead Dr Brentwood has 4 bedrooms, 4 baths and was built in 2000. The property's zip code is 37027 which is in Brentwood, TN

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.