Nestled among mature trees within the prestigious, guard-gated Governors Club, this timeless colonial-inspired estate blends classic architecture with warm, elevated living. A sweeping front porch welcomes you home and invites slow mornings with coffee in hand, surrounded by the peaceful beauty of the golf course beyond. Thoughtfully positioned on a stunning treed homesite, the setting feels both private and picturesque.
Spanning just over 7,000 square feet, the home offers an exceptional layout designed for both everyday comfort and gracious entertaining. The main-level primary suite provides a serene retreat, while expansive living spaces are filled with natural light and refined architectural details throughout. Upstairs, a spacious bonus room offers incredible flexibility for recreation, media, or gathering space. The finished basement adds yet another layer of versatility with abundant room for entertaining, hobbies, fitness, or guests.
With four generously sized bedrooms, four full baths, and three half baths, every space has been thoughtfully designed with comfort and functionality in mind.
Beyond the home itself, Governors Club offers an extraordinary lifestyle with a championship golf course, elegant clubhouse with dining, fitness center, resort-style pools, tennis, and a vibrant calendar of community events and social gatherings. A rare opportunity to experience timeless luxury and everyday ease in one of Middle Tennessee’s most sought-after communities.
Active
$2,799,000
27 Colonel Winstead Dr, Brentwood, TN 37027
4beds
7,138sqft
Single Family Residence, Residential
Built in 2000
0.85 Acres Lot
$-- Zestimate®
$392/sqft
$462/mo HOA
What's special
Sweeping front porchStunning treed homesiteMature treesClassic architectureFour generously sized bedroomsRefined architectural details throughout
- 59 days |
- 427 |
- 13 |
Zillow last checked:
Listing updated:
Listed by:
Danielle Keegan 949-351-4787,
Benchmark Realty, LLC 615-371-1544,
Kori Kintsch 615-830-3626,
Benchmark Realty, LLC
Source: RealTracs MLS as distributed by MLS GRID,MLS#: 3215647
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 7
- Full bathrooms: 4
- 1/2 bathrooms: 3
- Main level bedrooms: 1
Bedroom 1
- Area: 320 Square Feet
- Dimensions: 16x20
Bedroom 2
- Area: 252 Square Feet
- Dimensions: 14x18
Bedroom 3
- Area: 288 Square Feet
- Dimensions: 16x18
Bedroom 4
- Area: 240 Square Feet
- Dimensions: 15x16
Den
- Area: 225 Square Feet
- Dimensions: 15x15
Dining room
- Area: 220 Square Feet
- Dimensions: 11x20
Other
- Area: 180 Square Feet
- Dimensions: 12x15
Kitchen
- Area: 256 Square Feet
- Dimensions: 16x16
Living room
- Area: 408 Square Feet
- Dimensions: 17x24
Other
- Area: 576 Square Feet
- Dimensions: 24x24
Other
- Area: 150 Square Feet
- Dimensions: 15x10
Recreation room
- Area: 756 Square Feet
- Dimensions: 21x36
Heating
- Central
Cooling
- Ceiling Fan(s), Central Air
Appliances
- Included: Built-In Electric Oven, Double Oven, Cooktop, Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
- Laundry: Electric Dryer Hookup, Washer Hookup
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
- Basement: Finished,Unfinished
- Number of fireplaces: 6
- Fireplace features: Den, Family Room, Gas, Great Room, Living Room, Recreation Room
Interior area
- Total structure area: 7,138
- Total interior livable area: 7,138 sqft
- Finished area above ground: 5,509
- Finished area below ground: 1,629
Video & virtual tour
Property
Parking
- Total spaces: 3
- Parking features: Garage Door Opener, Garage Faces Side
- Garage spaces: 3
Features
- Levels: Three Or More
- Stories: 3
- Patio & porch: Deck, Covered, Patio, Porch, Screened
- Exterior features: Balcony
- Pool features: Association
Lot
- Size: 0.85 Acres
- Dimensions: 139 x 249
Details
- Parcel number: 094034N A 01600 00016034O
- Special conditions: Standard
- Other equipment: Irrigation System
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence, Residential
Materials
- Brick, Stucco
- Roof: Shingle
Condition
- New construction: No
- Year built: 2000
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Water Available, Underground Utilities
Community & HOA
Community
- Security: Carbon Monoxide Detector(s), Security Gate, Security Guard, Security System, Smoke Detector(s)
- Subdivision: Governors Club The Ph 2
HOA
- Has HOA: Yes
- Amenities included: Clubhouse, Fitness Center, Gated, Golf Course, Park, Playground, Pool, Sidewalks, Tennis Court(s), Underground Utilities, Trail(s)
- HOA fee: $462 monthly
Location
- Region: Brentwood
Financial & listing details
- Price per square foot: $392/sqft
- Tax assessed value: $2,189,200
- Annual tax amount: $8,155
- Date on market: 5/18/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/18/2026 | Listed for sale | $2,799,000+160.4%$392/sqft |
Source:  RealTracs MLS as distributed by MLS GRID #3215647 Report a problem | ||
| 11/8/2004 | Sold | $1,075,000+437.5%$151/sqft |
Source: Public Record Report a problem | ||
| 4/1/1999 | Sold | $200,000$28/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $8,155 +7.2% | $547,300 +56.1% |
| 2024 | $7,608 | $350,600 |
| 2023 | $7,608 | $350,600 |
| 2022 | $7,608 | $350,600 |
| 2021 | $7,608 -0.7% | $350,600 +18% |
| 2020 | $7,662 | $297,000 |
| 2019 | $7,662 +2.8% | $297,000 |
| 2018 | $7,455 | $297,000 |
| 2017 | $7,455 | $297,000 |
| 2016 | -- | $297,000 +14.7% |
| 2015 | -- | $259,025 |
| 2014 | -- | $259,025 |
| 2013 | -- | $259,025 |
| 2012 | -- | $259,025 |
| 2011 | -- | $259,025 -6.9% |
| 2007 | $7,654 | $278,323 |
| 2006 | $7,654 -4.9% | $278,323 +16.9% |
| 2005 | $8,048 | $238,103 |
| 2004 | $8,048 | $238,103 |
| 2002 | $8,048 | $238,103 |
| 2001 | -- | $238,103 -77.1% |
| 2000 | -- | $1,037,637 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 37027
Nearby schools
GreatSchools rating
- 9/10Crockett Elementary SchoolGrades: PK-5Distance: 2.1 mi
- 9/10Woodland Middle SchoolGrades: 6-8Distance: 2.2 mi
- 10/10Ravenwood High SchoolGrades: 9-12Distance: 2.1 mi
Schools provided by the listing agent
- Elementary: Crockett Elementary
- Middle: Woodland Middle School
- High: Ravenwood High School
Source: RealTracs MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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