260 Lookout Dr, Winchester TN 37398
Welcome to one of the premier homes in The Highlands of Winchester. Offering over 3,100 square feet of thoughtfully designed living space, this custom-built home combines quality craftsmanship, timeless finishes, and the security of a gated community just minutes from downtown Winchester and beautiful Tims Ford Lake. High-end finishes, spacious rooms, and carefully selected details create a home that feels both elegant and comfortable. The heart of the home is a beautifully appointed kitchen that opens to the main living area. An oversized two-car garage includes additional space for a golf
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 Winchester
This property is offered at $208 per square foot, compared with a $242 median for active 4-bedroom homes in Winchester. Its asking price falls near the 44th percentile of that active group. The comparison uses 65 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 45 days, while the current cohort averages 42 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 $386,500, and the median is $185 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 |
|---|---|---|---|---|
| 249 Lookout Dr | Jul 17, 2026 | 3 bd · 2,973 sqft | $515,000 | 0.0 mi |
| 123 Lookout Dr | Jul 23, 2026 | 3 bd · 1,869 sqft | $418,000 | 0.2 mi |
| 240 Brandi Cir | Jun 19, 2026 | 3 bd · 1,750 sqft | $355,000 | 0.6 mi |
| 178 Sugar Leaf Cir | Jun 22, 2026 | 4 bd · 2,815 sqft | $562,410 | 0.7 mi |
| 207 Franklin Park | May 29, 2026 | 3 bd · 1,400 sqft | $259,250 | 0.9 mi |
| 0 North Jefferson Street | Jun 18, 2026 | — | $180,000 | 0.9 mi |
| 110 Dotson Ln | Jun 3, 2026 | 3 bd · 1,380 sqft | $210,000 | 1.0 mi |
| 16 Blairmont Ct | Jul 16, 2026 | 4 bd · 4,109 sqft | $700,000 | 1.0 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.
- $649,000 · Active
Location reference points
How this address sits within the Winchester 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.
- Downtown Winchester1.5 miles straight-line · roughly 3 driving minutes
- Tims Ford Lake9.7 miles straight-line · roughly 17 driving minutes
- Downtown Tullahoma12.1 miles straight-line · roughly 22 driving minutes
- Arnold Air Force Base12.9 miles straight-line · roughly 23 driving minutes
- Downtown Manchester19.0 miles straight-line · roughly 34 driving minutes
Continue comparing
Similar active homes in Winchester
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 Winchester homes for sale · See the Winchester market report