305 Oak Leaf Cir, Winchester TN 37398
This spacious four-bedroom home with a bonus room and three full baths offers a wonderful blend of comfort, character, and opportunity. A detached garage with a versatile room above provides ideal space for a storage or a studio. The backyard is an entertainer’s retreat, featuring an in-ground pool surrounded by a generous deck and framed by a serene wooded backdrop that offers both privacy and tranquility. Inside, the living room boasts vaulted ceilings and a cozy wood-burning fireplace, creating a warm and inviting atmosphere. Enjoy the best of outdoor living with Tim’s Ford State Park and T
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 $192 per square foot, compared with a $242 median for active 4-bedroom homes in Winchester. Its asking price falls near the 11th percentile of that active group. The comparison uses 66 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 171 days, while the current cohort averages 44 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 4 closed sales within approximately 1.25 miles during the last six months. The median recorded sold price in this nearby sample is $192,500, and the median is $208 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 |
|---|---|---|---|---|
| 0 Michelle Lane | Jun 22, 2026 | — | $75,000 | 0.5 mi |
| 0 Maple Bend Rd | Jun 17, 2026 | — | $126,000 | 0.6 mi |
| 638 Haddon Ln | May 29, 2026 | 3 bd · 1,247 sqft | $259,000 | 0.9 mi |
| 614 Haddon Ln | May 29, 2026 | 3 bd · 1,247 sqft | $259,000 | 0.9 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.
- $357,900 · Active
- $357,900 · Off Market
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 Winchester4.0 miles straight-line · roughly 7 driving minutes
- Tims Ford Lake5.5 miles straight-line · roughly 10 driving minutes
- Downtown Tullahoma12.0 miles straight-line · roughly 21 driving minutes
- Arnold Air Force Base15.0 miles straight-line · roughly 27 driving minutes
- Downtown Manchester20.8 miles straight-line · roughly 37 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