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

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194 listings found
36 Meadowwood Ln in Winchester home for salePending
$369,125
3.00 bd2.00 ba1,428 sqft
36 Meadowwood Ln
Winchester, TN 37398
Meadow Wood Acres subdivision
8 Latitude Dr in Winchester home for salePending
$587,900
5.00 bd4.00 ba2,753 sqft
8 Latitude Dr
Winchester, TN 37398
Twin Creeks Village Ph X subdivision
416 Colonial Dr in Winchester home for saleFor Sale
$335,000
3.00 bd2.00 ba1,587 sqft
416 Colonial Dr
Winchester, TN 37398
Cherokee Est subdivision
0 Sisk Rd in Winchester home for saleFor Sale
$349,900
3.00 bd2.00 ba1,605 sqft
0 Sisk Rd
Winchester, TN 37398
Hooper Meadows subdivision
805 N Jefferson St in Winchester home for saleFor Sale
$459,995
4.00 bd4.00 ba2,260 sqft
805 N Jefferson St
Winchester, TN 37398
None subdivision
220 Union Rd in Winchester home for saleFor Sale
$299,900
3.00 bd2.00 ba1,288 sqft
220 Union Rd
Winchester, TN 37398
Evanswood subdivision
260 Union Rd in Winchester home for saleFor Sale
$299,900
3.00 bd2.00 ba1,288 sqft
260 Union Rd
Winchester, TN 37398
Evanswood subdivision
22 Hammock Dr in Winchester home for saleFor Sale
$775,000
4.00 bd3.00 ba3,104 sqft
22 Hammock Dr
Winchester, TN 37398
Twin Creeks Village Ph III subdivision
369 Pickney Rd in Winchester home for saleFor Sale
$599,999
3.00 bd3.00 ba2,401 sqft
369 Pickney Rd
Winchester, TN 37398
Pickney subdivision
70 Island Way in Winchester home for saleFor Sale
$459,900
4.00 bd3.00 ba2,578 sqft
70 Island Way
Winchester, TN 37398
Twin Creeks Village Ph Viii subdivision
794 River Watch Way in Winchester home for salePending
$574,900
3.00 bd2.00 ba1,909 sqft
794 River Watch Way
Winchester, TN 37398
Twin Creeks Village Ph Xiii subdivision
49 Driftwood Ct in Winchester home for salePending
$612,086
4.00 bd3.00 ba2,893 sqft
49 Driftwood Ct
Winchester, TN 37398
Twin Creeks Village Ph X 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
117 Carol Cir in Winchester home for saleFor Sale
$330,000
3.00 bd2.00 ba1,750 sqft
117 Carol Cir
Winchester, TN 37398
Lenwood Acres subdivision
133 Westmeade Dr in Winchester home for saleFor Sale
$597,500
4.00 bd3.00 ba3,103 sqft
133 Westmeade Dr
Winchester, TN 37398
Franklin Hills Ph Iv subdivision
56 Deer Valley Cir in Winchester home for saleFor Sale
$399,900
2.00 bd2.00 ba1,664 sqft
56 Deer Valley Cir
Winchester, TN 37398
Deer Valley subdivision
204 Homeward Ave in Winchester home for saleFor Sale
$355,000
3.00 bd3.00 ba1,988 sqft
204 Homeward Ave
Winchester, TN 37398
Rogers Haven subdivision
0 Golf Shore Dr in Winchester home for saleFor Sale
$688,000
3.00 bd3.00 ba2,313 sqft
0 Golf Shore Dr
Winchester, TN 37398
golf shore phase 3 subdivision
136 Bay Cove Trl in Winchester home for saleFor Sale
$1,499,000
4.00 bd4.00 ba4,035 sqft
136 Bay Cove Trl
Winchester, TN 37398
Fanning Bend Ph I subdivision
84 Meadowood Ln in Winchester home for saleFor Sale
$425,000
3.00 bd2.00 ba1,814 sqft
84 Meadowood Ln
Winchester, TN 37398
Meadow Wood Acres subdivision
322 N Porter St in Winchester home for saleFor Sale
$1,799,000
4.00 bd5.00 ba5,019 sqft
322 N Porter St
Winchester, TN 37398
Landings subdivision
602 Style St in Winchester home for saleFor Sale
$239,000
3.00 bd2.00 ba1,100 sqft
602 Style St
Winchester, TN 37398
N/A subdivision
1413 Little St in Winchester home for saleFor Sale
$215,900
3.00 bd2.00 ba1,014 sqft
1413 Little St
Winchester, TN 37398
ARLO ACRES subdivision
74 Maple Dr in Winchester home for salePending
$649,900
3.00 bd2.00 ba1,754 sqft
74 Maple Dr
Winchester, TN 37398
Dripping Springs Unit II subdivision

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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.

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