27 Colonel Winstead Dr, Brentwood, TN 37027
Governors Club The Ph 2 · Williamson County
Key Facts
Description
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.
Property Information
Property Type
Residential
Sub-Type
Single Family Residence
Year Built
2000
Stories
3
Living Area
7,138 sq ft
Lot Size
0.85 acres
Lot Dimensions
139 X 249
Garage Spaces
3
Parking Spaces
3
Days on Market
4
MLS® Listing#
3215647
Property Features
Interior
Exterior
Appliances
Cooling
Heating
Flooring
Fireplace
Basement
Parking
Laundry
Patio
Construction
Foundation
Roof
Security
Community
Utilities
Sewer
Water Source
Rooms
- 15x10
- 21x36
- 12x15
- 24x24
- Bedroom 116x20
- Bedroom 214x18
- Bedroom 316x18
- Bedroom 415x16
- Den15x15
- Dining Room11x20
- Kitchen16x16
- Living Room17x24
Schools
- Elementary:
- Crockett Elementary
- Middle:
- Woodland Middle School
- High:
- Ravenwood High School
Financial Details
HOA
$462 / Monthly
Annual Taxes
$8,155
Parcel Number
094034N A 01600 00016034O
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.
Affordability Calculator
$559,800
Estimated monthly payment
$14,897/mo
Principal $2,239,200 · Est. interest $3,123,883 over 30 yrs
Neighborhood Market Statistics
How this home compares to active listings in Brentwood, TN
- $1,000,000
- Median Listing Price
- 46
- Median Days on Market
- 4,545
- Median Sq Ft
- $397
- Median Price / Sq Ft
- 362
- Active Listings
- This home’s price is 180% above the area median.
- Its price per sq ft is 1% below the area median.
Market statistics compiled from active EXIT Realty® and MLS listings in Brentwood, TN.
Location
Points of Interest in Brentwood, TN
Showing the Brentwood area map.
Nearby Schools
Jordan Elementary School
Elementary · 1.4 mi away
Kenrose Elementary
Elementary · 1.8 mi away
Woodland Middle School
Secondary · 2.1 mi away
Ravenwood High School
Secondary · 2.1 mi away
Crockett Elementary
Elementary · 2.1 mi away
Edmondson Elementary School
Elementary · 2.2 mi away
Sunset Elementary School
Elementary · 2.9 mi away
Sunset Middle School
Secondary · 2.9 mi away
May Werthan Shayne Elementary School
Elementary · 3.4 mi away
Oliver Middle School
Secondary · 3.4 mi away
Clovercroft Elementary School
Elementary · 3.5 mi away
Lipscomb Elementary
Elementary · 3.6 mi away
Nolensville Elementary School
Elementary · 3.7 mi away
Montessori Academy
Elementary · 3.8 mi away
Primrose Schools
Elementary · 3.9 mi away
All God's Children Early LRNG Acad
School · 4.0 mi away
Kid City USA - Franklin
School · 4.0 mi away
Grace Christian Academy
School · 4.1 mi away
Gardner School
School · 4.1 mi away
Nolensville Elementary
Elementary · 4.3 mi away
Commute Calculator
Nearby Homes
Similar Homes Nearby
Similar Home Values
Comparable nearby listings and their asking prices.
| Address | Price | Beds | Baths | Sq Ft |
|---|---|---|---|---|
| 6306 Milbrook Rd, Brentwood, TN | $1,969,000 | 4 | 4 | 4,546 |
| 1816 Tiverton Pl, Brentwood, TN | $1,990,000 | 6 | 6 | 4,548 |
| 85 Governors Way, Brentwood, TN | $1,994,000 | 4 | 5 | 4,878 |
| 5448A Franklin Pike Cir, Brentwood, TN | $1,995,000 | 4 | 5 | 4,756 |
| 220 Long Valley Rd, Brentwood, TN | $1,995,000 | 3 | 3 | 2,409 |
| 1810 Legacy Cove Ln, Brentwood, TN | $1,999,900 | 5 | 4 | 4,515 |
Moving Cost Estimate
EXIT Agents in Brentwood
Listing Courtesy: Benchmark Realty, LLC - 9493514787
Last Updated: 2026-05-17