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Start here

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Before you start looking
The buying timeline

Afford it

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Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

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Rentals
Commercial

167 listings

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Compare selling options
Get an instant cash offer
Buy before you sell

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3 beds New construction

167 listings

Homes for Sale in Winchester, TN

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24 of 167 Listings

Map

24 of 167 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

14Active

$149,900

3 bd · 2 ba · 1,248 sqft

696 Halfmoon Rd, Winchester, TN

Ashley Lynch · Lynch Rigsby Realty & Auction, LLC

Price Reduced20Active

$234,900

3 bd · 2 ba · 1,875 sqft

114 Bel Aire Dr, Winchester, TN

Wayne Neese · Coldwell Banker Southern Realty

New100Active

$1,100,000

3 bd · 4 ba · 2,194 sqft

105 Maple Dr, Winchester, TN

Alexander Brandau IV · Aperture Global

New53Active

$415,000

3 bd · 2 ba · 1,996 sqft

1835 Williams Cove Rd, Winchester, TN

Fhonda Hatmaker · eXp Realty

New1Active

$632,400

3 bd · 3 ba · 2,635 sqft

13 Pine Bluff Trce, Winchester, TN

Susan Baker, Broker. GRI · BHGRE Baker & Cole

13Active

$229,000

3 bd · 1 ba · 1,154 sqft

814 S High St, Winchester, TN

April Smith Couch · John Smith Jr Realty and Auction LLC

85Active

$589,999

4 bd · 3 ba · 2,930 sqft

347 Campfire Ct, Winchester, TN

Angie Miller · John Smith Jr Realty and Auction LLC

66Active

$350,000

3 bd · 2 ba · 1,872 sqft

19 Carol Cir, Winchester, TN

Eberley (Ebbie) Holloway · Southern Middle Realty

16Active

$209,900

3 bd · 2 ba · 1,700 sqft

205 Sells St, Winchester, TN

Kaydence Transue · Better Homes & Gardens Real Estate Heritage Group

53Active

$1,175,000

2 bd · 3 ba · 2,460 sqft

645 Wildwood Trce, Winchester, TN

Angie Miller · John Smith Jr Realty and Auction LLC

41Active

$269,900

2 bd · 1 ba · 1,373 sqft

102 Oak Park, Winchester, TN

Shelia Lunsford · Benchmark Realty, LLC

20Active

Price unavailable

3 bd · 2 ba · 1,024 sqft

1306 Old Cowan Rd, Winchester, TN

Robert Boswell · Hanson Realty & Auction Company

19Active

Price unavailable

3 bd · 2 ba · 2,664 sqft

292 Old Holders Cove Rd, Winchester, TN

Thomas Ore · Winton Auction & Realty Co.

53Active

$749,900

3 bd · 3 ba · 2,052 sqft

96 Maple Dr, Winchester, TN

Derrick Foster · Freedom Realty

19Active

Price unavailable

3 bd · 2 ba · 2,664 sqft

292 Old Holders Cove Rd, Winchester, TN

Thomas Ore · Winton Auction & Realty Co.

36Active

$889,000

3 bd · 1 ba · 1,600 sqft

5630 Mansford Rd, Winchester, TN

Sam Hatfield · Sam Hatfield Realty, Inc.

62Active

$1,199,900

4 bd · 4 ba · 3,720 sqft

160 Wakeboard Way, Winchester, TN

Angela Privett · Benchmark Realty, LLC

28Active

$250,000

3 bd · 2 ba · 1,552 sqft

300 Edgewater Dr, Winchester, TN

Erica Paige Howard · Freedom Realty Group

77Active

$350,200

3 bd · 3 ba · 1,988 sqft

204 Homeward Ave, Winchester, TN

Lauren Whittle - THE PREFERRED GROUP · Keller Williams Russell Realty & Auction

60Active

$1,399,000

5 bd · 4 ba · 3,801 sqft

130 Peninsula Pt Dr, Winchester, TN

Ashley Lynch · Lynch Rigsby Realty & Auction, LLC

43Active

$245,000

2 bd · 1 ba · 1,292 sqft

1101 High St, N, Winchester, TN

Cole Hodges · Stones River Property Mgmt and Real Estate Service

1Active

$369,000

3 bd · 2 ba · 1,605 sqft

0 Sisk Rd, Winchester, TN

Angie Miller · John Smith Jr Realty and Auction LLC

98Active

$2,499,000

3 bd · 4 ba · 4,258 sqft

2032 Little Hurricane Rd, Winchester, TN

Melissa K. Stewart · Swaffords Property Shop

25Active

$364,900

3 bd · 2 ba · 1,498 sqft

1579 Rowe Gap Rd, Winchester, TN

Angie Miller · John Smith Jr Realty and Auction LLC

1 2…7

Listing data & MLS disclosures

Realtracs: Based on information submitted to the MLS GRID as of 2026-10-30 16:57:00 UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Winchester housing market

September 2026 · This period is still settling

Selling at 96.6% of asking price

Buyers here are paying below asking. MLS · 35 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 29, 2026

Median sale price: $554,000$280,000–$1,004,450 typical range
Price per sq. ft.: $234
Sales: 15
Paid in cash: 40.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $464,000

Winchester, TN community profile

Population: 9,947
Median income: $58,811
Housing units: 4,383
People per sq. mi.: 83.2
Area: 119.5 sq. mi.

Source: HJN community data

Explore Winchester homes

By price

Homes Under $300K
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By bedrooms

3 Bedroom Homes
4 Bedroom Homes

By feature

New Construction Homes

Nearby areas

ZIP codes

37388 (179)
37160 (176)
37398 (164)
37355 (127)
37387 (57)
37330 (55)
37356 (41)
37352 (29)

Cities

Tullahoma (179)
Shelbyville (176)
Manchester (127)
Tracy City (57)
Estill Springs (55)
Monteagle (41)
Lynchburg (29)
South Pittsburg (23)

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Listing data & MLS disclosures

Realtracs: Based on information submitted to the MLS GRID as of 2026-10-30 16:57:00 UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Winchester, TN community profile

Population: 9,947
Median income: $58,811
Housing units: 4,383
People per sq. mi.: 83.2
Area: 119.5 sq. mi.

Source: HJN community data

Winchester housing market

September 2026 · This period is still settling

Selling at 96.6% of asking price

Buyers here are paying below asking. MLS · 35 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 29, 2026

Median sale price: $554,000$280,000–$1,004,450 typical range
Price per sq. ft.: $234
Sales: 15
Paid in cash: 40.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $464,000

Homes for sale

165

Median days on market

41 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 65.1%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 10, 2026

Median home size: 1,752 sq. ft.

Winchester, TN Homes for Sale | Realty.com

Nearby areas

ZIP codes

37388 (179)
37160 (176)
37398 (164)
37355 (127)
37387 (57)
37330 (55)
37356 (41)
37352 (29)

Cities

Tullahoma (179)
Shelbyville (176)
Manchester (127)
Tracy City (57)
Estill Springs (55)
Monteagle (41)
Lynchburg (29)
South Pittsburg (23)