Winchester, TN · Live MLS

Winchester Homes for Sale

Every active home for sale in Winchester, TN — straight from the local Franklin County MLS and refreshed daily, not a stale portal feed. Filter by price, beds, or what matters most here (in-town or on the water, acreage, lake access), and I'll help you tour and negotiate the moment the right one lands.

Jon Smith · Orchard · 5.0 on Google (24 reviews) · RENE-certified negotiator

Search & filter Winchester listings →
200 listings found
57 Cypress Point Dr in Winchester home for saleFor Sale
$690,000
3.00 bd2.00 ba2,086 sqft
57 Cypress Point Dr
Winchester, TN 37398
Cypress Point subdivision
67 Lake Ln in Winchester home for saleFor Sale
$359,900
3.00 bd2.00 ba1,886 sqft
67 Lake Ln
Winchester, TN 37398
Shelley Heights subdivision
49 Why Worry Ln in Winchester home for saleFor Sale
$998,996
4.00 bd4.00 ba3,521 sqft
49 Why Worry Ln
Winchester, TN 37398
Twin Creeks Village Ph V subdivision
805 N Jefferson St in Winchester home for saleFor Sale
$499,900
4.00 bd4.00 ba2,260 sqft
805 N Jefferson St
Winchester, TN 37398
None subdivision
155 Hammock Dr in Winchester home for saleFor Sale
$1,049,994
4.00 bd5.00 ba3,375 sqft
155 Hammock Dr
Winchester, TN 37398
Twin Creeks Village Ph Iv subdivision
323 Ridgecrest Dr in Winchester home for saleFor Sale
$729,900
4.00 bd5.00 ba3,960 sqft
323 Ridgecrest Dr
Winchester, TN 37398
Franklin Hills Ph Vi subdivision
0 Ridgecrest Dr in Winchester home for saleFor Sale
$794,500
4.00 bd4.00 ba3,165 sqft
0 Ridgecrest Dr
Winchester, TN 37398
Franklin Hills subdivision
110 S Porter St in Winchester home for saleFor Sale
$695,000
8.00 bd4.00 ba3,187 sqft
110 S Porter St
Winchester, TN 37398
N/A subdivision
38 Murray Lake Dr in Winchester home for salePending
$339,999
2.00 bd2.00 ba1,683 sqft
38 Murray Lake Dr
Winchester, TN 37398
Murray Lake Estates subdivision
801 S High St in Winchester home for salePending
$279,900
3.00 bd2.00 ba1,697 sqft
801 S High St
Winchester, TN 37398
Embrey Add subdivision
322 N Porter St in Winchester home for saleComing Soon
$1,799,000
4.00 bd5.00 ba5,019 sqft
322 N Porter St
Winchester, TN 37398
Landings subdivision
8 Latitude Dr in Winchester home for saleFor Sale
$597,900
5.00 bd4.00 ba2,753 sqft
8 Latitude Dr
Winchester, TN 37398
Twin Creeks Village Ph X subdivision
103 Anderton Dr in Winchester home for saleFor Sale
$466,000
5.00 bd3.00 ba2,160 sqft
103 Anderton Dr
Winchester, TN 37398
Twin Creeks Village subdivision
108 Lookout Drive in Winchester home for saleFor Sale
$443,900
3.00 bd2.00 ba2,290 sqft
108 Lookout Drive
Winchester, TN 37398
Highlands subdivision
124 Lookout Drive in Winchester home for saleFor Sale
$424,900
4.00 bd2.00 ba1,890 sqft
124 Lookout Drive
Winchester, TN 37398
Highlands subdivision
58 Island Way in Winchester home for saleFor Sale
$434,000
4.00 bd3.00 ba2,660 sqft
58 Island Way
Winchester, TN 37398
Twin Creeks Village Ph Viii subdivision
135 Fanning Bend Dr in Winchester home for saleFor Sale
$1,060,000
4.00 bd4.00 ba2,919 sqft
135 Fanning Bend Dr
Winchester, TN 37398
Fanning Bend Ph I subdivision
262 Crimson Dr in Winchester home for saleFor Sale
$459,999
3.00 bd2.00 ba2,355 sqft
262 Crimson Dr
Winchester, TN 37398
Crimson Estates subdivision
404 S Jefferson St in Winchester home for salePending
$238,000
2.00 bd2.00 ba1,370 sqft
404 S Jefferson St
Winchester, TN 37398
Embrey Add subdivision
90 Pine Bluff Ct in Winchester home for saleFor Sale
$644,900
3.00 bd3.00 ba2,729 sqft
90 Pine Bluff Ct
Winchester, TN 37398
Whispering Pines subdivision
171 Raspberry Dr in Winchester home for salePending
$285,000
3.00 bd2.00 ba1,544 sqft
171 Raspberry Dr
Winchester, TN 37398
Magnolia Est Ph III subdivision
605 Gin St in Winchester home for saleFor Sale
$115,000
4.00 bd3.00 ba2,052 sqft
605 Gin St
Winchester, TN 37398
075C subdivision
406 2nd Ave, NW in Winchester home for saleFor Sale
$125,000
3.00 bd1.00 ba1,150 sqft
406 2nd Ave, NW
Winchester, TN 37398
N/A subdivision
71 Windjammer Ct in Winchester home for saleFor Sale
$750,000
4.00 bd4.00 ba3,017 sqft
71 Windjammer Ct
Winchester, TN 37398
Twin Creeks Village Ph Iv subdivision

Didn't find it? Try these

Quick routes to the searches Winchester buyers ask for most:

What your Winchester budget buys

General mid-2026 ranges — live pricing is in the grid above, and full trends live on the Winchester real estate overview. Because Winchester spans modest in-town houses and lakefront estates, a single citywide "average" hides more than it shows; compare within your band and your side of the in-town-vs-lake line.

BudgetWhat it typically buys in WinchesterNotes
Under $250KOlder and mid-century in-town homes on compact lots, some fixers, and the occasional condo — entry-level and investor range.Best value is usually a solid in-town house close to downtown and services; these move fastest, so set an alert.
$250K–$400KThe core of the market: updated 3-bed homes, newer construction in subdivisions, and homes with a little acreage.New-construction pockets (e.g. Stone Field Heights on city utilities) and lake-access communities start showing up here.
$400K–$700KLarger family and newer homes, real acreage, and lake-access properties near a community ramp — the lake premium begins.This is where in-town and lake budgets fork; the same dollar buys very differently on each side.
$700K+True dockable Tims Ford waterfront and estate homes, up well past a million dollars.Thinner, more seasonal inventory; the specific shoreline and dock matter more than any market-wide number.

Everyday in-town buyer activity clusters in the low-to-mid range, while the lake end stretches the top of the market well into seven figures. For a real number on your side of that line, I build the comp set rather than quoting a citywide median.

Where buyers look in Winchester

Downtown & in-town Winchester

County-seat homes close to the square, courthouse, schools district office, and everyday shopping — from starter houses to comfortable family homes. Newer in-town subdivisions like Stone Field Heights sit on city water, sewer, and gas. Browse all Winchester homes →

Tims Ford lake-access corridors

Communities minutes from the water with deeded access or a community ramp — Dripping Springs, Hopkins Point, gated Twin Creeks Village (marina, pools, clubhouse), and the newer Fanning Bend. Tims Ford lake homes →

Rural Franklin County near Winchester

Acreage, mini-farms, and country properties just outside the city core — room for a shop, a garden, or animals, often on well and septic. Franklin County real estate →

How I help you buy in Winchester, beyond the portal

The portals all show roughly the same feed. What they can't do is walk you through the in-town-vs-lake decision, read an older house, and protect you once you're under contract.

See it first

Real-time MLS alerts, plus a heads-up on coming-soon and off-market homes before they hit the portals.

Know the home

Winchester runs from mid-century in-town houses to lake properties. I read the older stock (roof, HVAC, and well/septic outside the city) and the lake-access diligence — what's true dockable waterfront vs. a community ramp, dock permits, TVA shoreline rules, and flood considerations.

Win the deal

RENE-certified negotiation for your bottom line — including second-home and lake buyers where comps are thin — plus local lender intros and inspections coordinated through closing. Reviews & results →

Winchester is a steady, not-frantic market: well-priced, move-in-ready in-town homes go under contract at a reasonable clip while ambitiously priced or dated ones sit, and inventory runs the full range from modest in-town houses to lakefront properties well past a million dollars. The two big data providers genuinely disagree on Winchester right now, so I keep the live count, median, and days-on-market in the MLS stat bar above and the trend read on the hub. For full price trends, the county-seat/economy picture, and how Winchester compares to the sister city up the highway, see the Winchester real estate overview and Franklin County real estate.

Winchester buyer FAQ

Is Winchester, TN a good place to buy a home?

For a lot of buyers, yes. Winchester is the county seat of Franklin County and the government, healthcare, and shopping hub for the whole area, and it sits right on the doorstep of Tims Ford Lake for boating, bass fishing, and Tims Ford State Park. It's affordable by Middle Tennessee standards, Tennessee has no state income tax, and the local tax bill is modest. Homes here are served by Franklin County Schools (the countywide district, not Tullahoma City Schools), so it's worth confirming the exact zone for any specific home. Whether it's the right fit comes down to your budget, whether you want to be in town or on the water, and your school priorities — happy to walk through the tradeoffs.

What is the average home price in Winchester, TN?

It genuinely depends who you ask right now — the major data providers disagree on Winchester, and a single citywide "average" is close to useless here because it mixes modest in-town houses with lakefront estates that run past a million dollars. Rather than quote a number that hides your reality, I keep the live median and days-on-market in the MLS stat bar at the top of this page, and I pull real, comparable sold prices for the specific area, price band, and side of the in-town-vs-lake line you're considering. For the fuller market read, see the Winchester real estate overview — the comps for your search matter far more than any citywide figure.

How do Tims Ford Lake homes compare to in-town Winchester?

They behave like two different markets. In-town Winchester is the more affordable and more predictable side — established neighborhoods close to downtown, the schools, and services. Tims Ford homes generally carry a premium, but how much depends on the kind of access: true dockable waterfront sits at the top (well into seven figures), lake-view and community-ramp homes below that, and simple lake-access communities lower still. Lake inventory is also thinner and more seasonal. Compare within the right bucket, waterfront to waterfront and in-town to in-town, which is exactly the comp work I do before you offer. The full lake picture lives on my Tims Ford Lake guide.

Ready to see Winchester homes in person?

Send me your must-haves — in town or on the lake — and I'll set up a live search, plus first dibs on new listings before they spread to the portals. No pressure, no obligation.

Free Access

Register to see all home photos. The home's details stay open while you decide.

Log inRegister