27 Colonel Winstead Dr, Brentwood TN 37027
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 deta
CloseDaily local analysis
Facts and context beyond the MLS description
The sections below combine this listing's current facts with locally retained inventory, sale, and location data. They are generated from the same MLS replica that powers the page, without an external data request during your visit.
Current market context
How this property compares in Brentwood
This property is offered at $364 per square foot, compared with a $337 median for active 4-bedroom homes in Brentwood. Its asking price falls near the 91st percentile of that active group. The comparison uses 172 active or publicly marketable listings from the same local MLS source, filtered to the same bedroom group rather than mixing every home size together.
The property has been tracked for 0 days, while the current cohort averages 51 days on market. These figures are a point-in-time inventory comparison, not an appraisal or prediction; condition, lot, updates, exact location, and concessions can move an individual sale away from the city-level pattern.
Nearby closed sales
Recent sold homes near this property
The local sold-history cache contains 8 closed sales within approximately 1.25 miles during the last six months. The median recorded sold price in this nearby sample is $1,865,000, and the median is $376 per square foot where square footage was reported.
Nearby sales are useful context, but they are not automatically comparable: renovation level, acreage, water access, construction quality, financing, and seller concessions can materially change a result. A property-specific valuation should review the most similar homes and the full MLS record before drawing a conclusion.
| Address | Sold | Home | Sold price | Distance |
|---|---|---|---|---|
| 5 Colonel Winstead Dr | Aug 7, 2026 | 6 bd · 8,887 sqft | $3,400,000 | 0.3 mi |
| 85 Governors Way | Aug 26, 2026 | 4 bd · 4,878 sqft | $1,830,000 | 0.3 mi |
| 24 Ironwood Ln | Jun 5, 2026 | 4 bd · 6,493 sqft | $1,900,000 | 0.3 mi |
| 18 Ironwood Ln | Aug 19, 2026 | 4 bd · 4,825 sqft | $1,950,000 | 0.4 mi |
| 17 Ironwood Ln | Aug 4, 2026 | 4 bd · 4,961 sqft | $1,720,000 | 0.4 mi |
| 5 Angel Trce | Jul 27, 2026 | 5 bd · 4,611 sqft | $2,000,000 | 0.4 mi |
| 1539 Abbottsford Rd | Jul 7, 2026 | 4 bd · 3,786 sqft | $1,425,000 | 0.4 mi |
| 4 Winged Foot Pl | Jul 30, 2026 | 4 bd · 3,855 sqft | $1,430,000 | 0.4 mi |
MLS timeline
Price and status history
This timeline records the price and public status snapshots received by CloseDaily from the local MLS replica. It is retained separately from the current listing so later changes do not erase the earlier market history. Dates reflect when the source record changed or was first observed by the sync system.
- $2,599,000 · Coming Soon
- $2,599,000 · Active
Location reference points
How this address sits within the Brentwood area
These distances are precomputed from the listing coordinates and a maintained set of regional landmarks; no mapping service is called when this page loads. Mileage is straight-line distance. Driving minutes are a planning estimate derived from that distance and should be checked against a live route before a showing or commute.
- I-24 at Manchester49.2 miles straight-line · roughly 88 driving minutes
- Downtown Manchester49.7 miles straight-line · roughly 89 driving minutes
- Downtown Tullahoma51.6 miles straight-line · roughly 92 driving minutes
- Arnold Air Force Base54.2 miles straight-line · roughly 97 driving minutes
- Tims Ford Lake59.5 miles straight-line · roughly 106 driving minutes
Continue comparing
Similar active homes in Brentwood
These active listings are in the same city and a nearby price range. Each link is rendered on the server so visitors and search engines can move between the property, the city inventory, and other relevant homes without returning to a generic search page.
View all Brentwood homes for sale · See the Brentwood market report