27 Colonel Winstead Dr, Brentwood, Tennessee 37027

TN, Brentwood
$2,599,000
  • Active Status
  • 10 Dayz On Cribz Total Days
  • Residential Property Type
  • 4 Beds Total Bedrooms
  • 7 Baths Full + Half Bathrooms
  • 7138 Total Sqft $364/sqft
  • 0.85 Acres Lot/Land Size
  • 2000 Year Built
  • Mortgage Wizard 3000 Advanced Breakdown
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 Details
  • Property Type: Residential
  • Listing Type: For Sale
  • MLS #: 3519030
  • Price: $2,599,000
  • Half Bathrooms: 3
  • Full Bathrooms: 4
  • Square Footage: 7,138 Sqft
  • Year Built: 2000
  • Lot Area: 0.85 Acre
  • Office Name: Benchmark Realty, LLC
  • Agent Name: Danielle Keegan
  • Property Sub Type: Single Family Residence
  • Roof: Shingle
  • Listing Status: Active
Location Info
  • Street Number: 27
  • Street: Colonel Winstead Dr
  • City Brentwood
  • State TN
  • Zipcode 37027
  • County Williamson County, TN
  • Subdivision Governors Club The Ph 2
  • Longitude: W87° 15' 55.8''
  • Latitude: N35° 58' 27.6''
  • 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.
Features
  • Heating System Central
  • Cooling System Central Air, Ceiling Fan(s)
  • Basement Finished, Unfinished
  • Fireplace Gas, Living Room, Family Room, Great Room, Den, Recreation Room
  • Patio Covered, Patio, Screened, Porch, Deck
  • Parking Garage Door Opener, Garage Faces Side
  • Utilities Water Available
  • Exterior Features Balcony
  • Fireplaces Total 6
  • Flooring Wood, Carpet, Tile, Marble
  • Interior Features Walk-In Closet(s), High Ceilings, Built-in Features, Pantry, Wet Bar, Entrance Foyer, Bookcases, Ceiling Fan(s), Central Vacuum, Extra Closets
  • Laundry Features Electric Dryer Hookup, Washer Hookup
  • Sewer Public Sewer
Appliances
  • Cooktop
  • Dishwasher
  • Microwave
  • Refrigerator
  • Dryer
  • Washer
  • Disposal
  • Double Oven
  • Stainless Steel Appliance(s)
  • Ice Maker
  • Built-In Electric Oven
Schools
  • Elementary School: Crockett Elementary
  • Middle School: Woodland Middle School
  • High School: Ravenwood High School
Additional Info
  • Water Source: Public
  • Association Amenities: Clubhouse,Fitness Center,Gated,Golf Course,Park,Playground,Pool,Sidewalks,Tennis Court(s),Underground Utilities,Trail(s)
  • Building Size: 7,138 Sqft
  • Construction Materials: Stucco, Brick, Hardboard Siding
  • Foundation Details: Slab
  • Garage: 3 Spaces
  • Levels: Three Or More
  • Lot Size Dimensions: 139 X 249
  • On Market Date: August 21st, 2026
  • Previous Price: $2,599,000
  • Stories: 3
Financial
  • Association Fee: $462
  • Association Fee Frequency: Monthly
  • Association: Yes
  • Annual Tax Amount: $8,155
Listing Data
  • Co List Agent Full Name: Kori Kintsch
  • Co List Office Name: Benchmark Realty, LLC
  • Mls Status: Active
  • Originating System Name: RealTracs
  • Special Listing Conditions: Standard
  • Modification Timestamp: Aug 21st, 2026 @ 5:02am
  • Status Change Timestamp: Aug 21st, 2026 @ 5:00am
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