309 2nd Ave, NW, Winchester TN 37398
SELLER OFFERING OWNER FINANCING AT 5.75% — This income-producing property just over a block from downtown Winchester, provides a rare opportunity for buyers seeking investment property in Tennessee with immediate rental income and future flexibility. Built in 1917, this historic, commercially zoned 5-bedroom, 2-bath residence generates approximately $2,000/month in rental income and includes approximately 3,922 sq ft on a .34-acre lot in the heart of Winchester. The property features original hardwood floors, spacious living areas, and a covered front porch that adds character and tenant appea
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 $121 per square foot, compared with a $217 median for active five-or-more-bedroom homes in Winchester. Its asking price falls near the 25th percentile of that active group. The comparison uses 19 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 25 days, while the current cohort averages 43 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 $218,000, and the median is $145 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 |
|---|---|---|---|---|
| 105 Shephard St, N | Jun 16, 2026 | 3 bd · 1,358 sqft | $323,000 | 0.1 mi |
| 217 S Porter St | Jun 18, 2026 | 3 bd · 1,575 sqft | $218,000 | 0.3 mi |
| 215 S Porter St | Jun 18, 2026 | 3 bd · 1,575 sqft | $218,000 | 0.3 mi |
| 213 S Porter St | Jun 18, 2026 | 3 bd · 1,575 sqft | $218,000 | 0.3 mi |
| 211 S Porter St | Jun 18, 2026 | 3 bd · 1,575 sqft | $218,000 | 0.3 mi |
| 146 Island Way | Jun 1, 2026 | 4 bd · 2,578 sqft | $478,000 | 0.5 mi |
| 714 N Cedar St | Jul 24, 2026 | 2 bd · 1,150 sqft | $175,000 | 0.5 mi |
| 592 River Watch Way | Jun 30, 2026 | 4 bd · 2,275 sqft | $405,000 | 0.5 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.
- $475,000 · 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 Winchester0.2 miles straight-line · roughly 3 driving minutes
- Tims Ford Lake9.3 miles straight-line · roughly 17 driving minutes
- Downtown Tullahoma13.3 miles straight-line · roughly 24 driving minutes
- Arnold Air Force Base14.5 miles straight-line · roughly 26 driving minutes
- Downtown Manchester20.6 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