27 Colonel Winstead Dr, Brentwood, TN 37027
27 Colonel Winstead Dr, Brentwood, TN 37027, Active at $2,599,000 ($364/sq ft). 4 bd · 5.5 ba (5 full, 1 half) · 7,138 sqft · $364/sqft · 0.85 ac.
27 Colonel Winstead Dr, Brentwood, TN 37027, Active at $2,599,000 ($364/sq ft). 4 bd · 5.5 ba (5 full, 1 half) · 7,138 sqft · $364/sqft · 0.85 ac.
Active · $2,599,000
MLS #3519030 · listed May 18, 2026 · 170 days on market · updated August 20, 2026
4-bed, 5.5-bath home at 27 Colonel Winstead Dr in Governors Club The Ph 2, Brentwood, 7,138 sqft, $2,599,000 ($364/sqft), by Benchmark Realty, LLC.
27 Colonel Winstead Dr is a 4-bedroom, 5.5-bath home in Brentwood, TN 37027, offered at $2,599,000, about $364/sq ft across 7,138 sq ft.
At $364/sq ft, this home is about 3% below the Governors Club median list price per square foot of $377.
Recently sold in Brentwood 37027: 280 comparable homes from $1,690,000 to $3,500,000, a median of $427/sq ft; this listing at $364/sq ft is about 15% below recent sold prices.
Market read: the Brentwood 37027 homes market is balanced as of October 28, 2026, at about 4.1 months of inventory; recent sales have closed near 98.1% of list in the 12 months to October 29, 2026.
All-in, about $16,843/mo at 20% down (7.60% 30-year fixed).
Beyond principal and interest, the recurring carrying costs on this home (property tax, insurance, and HOA) run about $2,162/mo, roughly 13% of the all-in monthly payment.
At the current 7.35% 30-year rate, principal and interest on this home runs about $14,325/mo; at the 6.77% rate of about three months ago it would be roughly $13,513/mo, so monthly P&I is about $812 higher now.
School zone: assigned to Crockett Elementary, Woodland Middle School, Ravenwood High School. Attendance zones can change; verify current assignment with the district.
Next step: ask Grant Hammond anything about 27 Colonel Winstead Dr (comps, HOA, tours) and he replies personally, usually same day.
Analysis by Grant Hammond, Compass RE. Figures as of August 20, 2026. Realtracs via IDX.
This is a standard residential home, not a permitted short-term rental.
More context: homes for sale in Brentwood.
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.
Listing remarks via the Realtracs Internet Data Exchange.
Complete reported fields for 27 Colonel Winstead Dr (reference).
| Date | Event | Price | Change |
|---|---|---|---|
| Listed | $2,599,000 |
Listed May 18, 2026, this listing has been on the market 170 days as of November 4, 2026. The asking price has not changed since it was listed.
County assessment from Williamson County public records; listing-cycle history tracked by the GH Market Engine.
27 Colonel Winstead Dr has 2 Realtracs listing records in the GH Market Engine archive. Every dated event the engine holds for this address, newest first, with its source.
| Date | Event | Price | Source |
|---|---|---|---|
| Listing removed | n/a | Realtracs MLS #3215647 | |
| by | Listed for sale | $2,799,000 | Realtracs MLS #3215647 |
| Listed for sale | $2,599,000 | Realtracs MLS #3519030 |
Realtracs listing activity before June 18, 2026 is not in our archive. Recorded sales come from Williamson County public records. "by" marks a date the archive learned after the fact.
Estimated monthly ownership for 27 Colonel Winstead Dr at $2,599,000: principal & interest, property tax, insurance, and HOA. Estimate only; not a loan offer.
| List price | $2,599,000 |
|---|---|
| HOA dues | $462 / mo |
| Property tax basis | Assessed value × 25% (TN residential ratio) × the Williamson County rate |
Estimated total monthly payment for 27 Colonel Winstead Dr is about $16,843/mo, 20% down on a 30-year fixed at 7.60% (a jumbo loan), including principal & interest $14,681, estimated property tax $807, homeowners insurance $893, and HOA dues $462. Estimate only; not a loan offer.
| Principal & interest | $14,681/mo |
|---|---|
| Property tax (est.) | $807/mo |
| Homeowners insurance (est.) | $893/mo |
| HOA dues | $462/mo |
| Estimated total | $16,843/mo |
Assumes 20% down, 30-year fixed at 7.60% (Mortgage News Daily, as of October 28, 2026). Property tax uses the Brentwood, Williamson County rate at the 25% TN residential ratio. Estimate only; not a loan offer or appraisal. Enable JavaScript to adjust down payment, term, loan type, and rate.
| 30-year rate | Principal & interest | Est. total / mo | vs current |
|---|---|---|---|
| 6.60% | $13,279/mo | $15,441/mo | -$1,402/mo |
| 7.10% | $13,973/mo | $16,135/mo | -$708/mo |
| 7.60% | $14,681/mo | $16,843/mo | current |
| 8.10% | $15,402/mo | $17,564/mo | +$721/mo |
| 8.60% | $16,135/mo | $18,297/mo | +$1,454/mo |
Principal & interest on a 30-year fixed at 20% down ($2,079,200 loan), with property tax, insurance, and HOA held constant at $2,162/mo. Current 30-year fixed 7.60% (Mortgage News Daily, as of October 28, 2026). Estimate only; not a loan offer.
Owning 27 Colonel Winstead Dr runs about $16,843/mo all-in, from the payment estimate above. Whether buying beats renting turns on how long you stay, how fast prices and rents move, and the rent you would otherwise pay. Turn on JavaScript to model those assumptions and find the year buying pulls ahead.
Method: net cost to own equals down payment plus about 3% closing plus payments made, minus equity built (principal paid and appreciation) and about 7% exit costs, measured against cumulative rent. Broker commissions are not set by law and are fully negotiable. Estimate only; not financial advice.
The Williamson County appraised value of $1,402,400 trails the $2,599,000 list price. If the next reassessment moves the appraised value toward today's market, estimated annual property tax would rise from about $5,224 now to roughly $9,681 (appraised value times the 25% Tennessee residential ratio times the Brentwood, Williamson County rate). Reassessment timing and the certified rate can change, and a purchase does not by itself trigger reassessment. Verify with the Williamson County Assessor of Property and Trustee. Estimate only.
| Metric | This home | Governors Club active | Recently sold |
|---|---|---|---|
| Price / sq ft | $364 | $393 median | $427 median |
| Price position | 33rd pctile | -7% vs median | ~98.1% of list |
| Recent closings | - | - | 280 sales |
This listing beside the active Governors Club market and recent recorded closings. Computed by Grant Hammond from Realtracs via IDX, as of November 4, 2026.
Among the 12 active homes in Governors Club, this home at $364/sq ft falls in the 33rd percentile on price per square foot.
Computed by Grant Hammond from 12 Governors Club comparables (Realtracs via IDX), as of November 4, 2026, refreshed weekly.
Median list price per square foot for active single-family homes by high-school attendance zone. Attendance zones cross city mailing lines; this is a price comparison, not a rating.
| High-school zone | Median $/sq ft |
|---|---|
| Brentwood | $367/sq ft |
| Ravenwood | $351/sq ft |
| Franklin | $349/sq ft |
| Independence | $338/sq ft |
| Fred J. Page | $327/sq ft |
| Centennial | $306/sq ft |
| Nolensville | $300/sq ft |
| Summit | $271/sq ft |
| Fairview | $261/sq ft |
Computed by Grant Hammond from active Williamson County listings (Realtracs via IDX).
| Active listings | 326 in Brentwood 37027 homes |
|---|---|
| Recent absorption | about 79.5 sales / mo |
| Months of inventory | 4.1 months, a balanced market |
Over the past 12 months, homes in Brentwood 37027 homes sold at about 98.1% of list price.
Recorded sales in Brentwood 37027 homes: 970 in the past 12 months.
Supply-side and recent-sale context for Brentwood 37027 homes. Sale figures are trailing 6/12/24-month medians of recorded Brentwood 37027 homes closings. Source Realtracs via IDX, as of October 28, 2026.
27 Colonel Winstead Dr sits in Governors Club The Ph 2, Brentwood, Williamson County.
In Governors Club, homes there are priced around $377 per square foot; inventory in Brentwood 37027 homes is running at about 4.1 months, a balanced market; recent sales in Brentwood 37027 closed near 98.1% of list price; 280 sales have been recorded in the past year.
Neighborhood housing-market facts computed by Grant Hammond from Realtracs via IDX, as of October 29, 2026.
Approximately 13 miles from downtown Nashville (straight-line distance).
27 Colonel Winstead Dr is zoned for Crockett Elementary, Woodland Middle School, Ravenwood High School. Attendance zones and enrollment change, confirm current zoning with the Williamson County Schools district before relying on it.
Get the full details, recent comparable sales, and any off-market options for 27 Colonel Winstead Dr - plus tour times if you want them. Grant Hammond, Compass RE, replies personally, usually the same day.
Comparable listings near 27 Colonel Winstead Dr, by price and size.
Listed by Danielle Keegan, Benchmark Realty, LLC. Properties marked with the MTRMLS logo are provided courtesy of the Realtracs Internet Data Exchange Program. Information believed accurate but not guaranteed. IDX by Diverse Solutions.
New construction in Brentwood, TN: why Rosebrooke and Witherspoon out-price the established Governors Club this summer, from a Nashville broker.
Brentwood TN home prices over the trailing six months: 461 closings, a $1,320,000 median, and a build-era split from $373K established resales to $4.32M new construction. A broker's data read, with live market stats, current MLS listings, and how Brentwood compares to Franklin.
Brentwood and Belle Meade luxury listings hitting MLS the week of May 26, 2026: price discipline, lot-size signal, and broker context for buyers and sellers.
Governors Club Brentwood homes for sale include luxury estate properties located in a gated Arnold Palmer golf community in Brentwood Tennessee just south of Nashville in Williamson County.
As of the latest update (August 20, 2026), 27 Colonel Winstead Dr, Brentwood is active, per Realtracs. Contact Grant Hammond, Compass RE, for current availability.
27 Colonel Winstead Dr was listed on May 18, 2026 and has been on the market 170 days as of November 4, 2026, per Realtracs.
No. The asking price has been $2,599,000 since it was listed on May 18, 2026.
27 Colonel Winstead Dr, Brentwood is listed at $2,599,000, about $364 per square foot across 7,138 square feet.
4 bedrooms and 5.5 bathrooms (5 full, 1 half).
About $364 per square foot ($2,599,000 across 7,138 sqft).
27 Colonel Winstead Dr, Brentwood was built in 2000.
Yes, 3 garage spaces, per the listing.
HOA dues are $462 per month, as listed.
27 Colonel Winstead Dr, Brentwood is in the Governors Club The Ph 2 subdivision of Brentwood.
About $16,843 a month with 20% down on a 30-year fixed at 7.60%, principal and interest $14,681, estimated property tax $807, insurance $893, and HOA $462. Estimate only; not a loan offer. Adjust the down payment, term, loan type, and rate in the financing calculator on this page.
27 Colonel Winstead Dr, Brentwood is zoned for Crockett Elementary, Woodland Middle School, Ravenwood High School. Attendance zones and enrollment change, verify current zoning with the Williamson County Schools district.
No, 27 Colonel Winstead Dr, Brentwood is a standard residential home, not a permitted short-term rental. Ask Grant Hammond about STR-eligible inventory if that is your goal.
Request a time using the tour form on this page (in-person or a live video walkthrough), or call or text Grant Hammond, Compass RE, at (615) 945-7123. Most showings are confirmed within 24 to 48 hours.
Grant Hammond, Compass RE, can prepare and present your offer, walk you through price, contingencies, and timeline, and represent you through closing. Start with the form on this page or call (615) 945-7123. Broker fees are not set by law and are fully negotiable.
Yes. This page shows the full photo set and reported MLS fields; contact Grant Hammond, Compass RE, for a disclosure packet, recent comparable sales, and any off-market options.
Grant Hammond, Compass RE (TN Broker), with 25+ years and $1B+ in Middle Tennessee sales and hundreds of millions in luxury closings. Use the tour or question form on this page.
At about $364 per square foot, 27 Colonel Winstead Dr, Brentwood ranks in the 33rd percentile of active Governors Club listings by price per square foot, roughly 3% below the Governors Club median; recent comparable sales in Governors Club closed near $427 per square foot. This is comp-based analysis by Grant Hammond, Compass RE, not an appraisal.
The Brentwood 37027 homes market is currently balanced, at about 4.1 months of inventory; recent sales have closed near 98.1% of list price over the past year, per Realtracs as of October 28, 2026.
Thinking of selling in Governors Club The Ph 2?
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