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Winchester, TN Homes for Sale — Page 5 | Realty.com
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Homes for Sale in Winchester, TN

Homes for Sale in Winchester, TN

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23 of 179 Listings
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Homes for Sale in Winchester, TN

23 of 179 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas
  1. 0 Golf Shore Dr — photo4Active

    $688,000

    3 bd · 3 ba · 2,313 sqft

    0 Golf Shore Dr, Winchester, TN

    Isaac Zimmerle · Benchmark Realty, LLC

  2. 645 Wildwood Trce — photoPrice Reduced51Active

    $1,150,000

    2 bd · 3 ba · 2,460 sqft

    645 Wildwood Trce, Winchester, TN

    George W Weeks · Team George Weeks Real Estate, LLC

  3. 171 Cypress Point Dr — photoPrice Reduced63Active

    $975,000

    5 bd · 5 ba · 3,191 sqft

    171 Cypress Point Dr, Winchester, TN

    B. J. Rigsby · Lynch Rigsby Realty & Auction, LLC

  4. 57 Cypress Point Dr — photoPrice Reduced76Active

    $682,000

    3 bd · 2 ba · 2,086 sqft

    57 Cypress Point Dr, Winchester, TN

    Danny Duffey · Duffeys Real Estate

  5. 266 Woods Edge Rd — photoPrice Reduced33Active

    $299,900

    3 bd · 2 ba · 1,500 sqft

    266 Woods Edge Rd, Winchester, TN

    Sharon Swafford · Swaffords Property Shop

  6. 1361 Joyce Ln — photo22Active

    $175,000

    3 bd · 2 ba · 1,644 sqft

    1361 Joyce Ln, Winchester, TN

    Thomas Ore · Winton Auction & Realty Co.

  7. 1325 Joyce Ln — photo24Active

    $225,000

    3 bd · 3 ba · 2,146 sqft

    1325 Joyce Ln, Winchester, TN

    Thomas Ore · Winton Auction & Realty Co.

  8. 924 Cline Ridge Rd — photo83Active

    $399,900

    2 bd · 2 ba · 1,450 sqft

    924 Cline Ridge Rd, Winchester, TN

    Dayla Bray- The Preferred Group · Keller Williams Russell Realty & Auction

  9. 95 Luttrell Dr — photo40Active

    $374,900

    3 bd · 2 ba · 1,657 sqft

    95 Luttrell Dr, Winchester, TN

    Thomas Ore · Winton Auction & Realty Co.

  10. 8 Latitude Dr — photoPrice Reduced57Active

    $587,900

    5 bd · 4 ba · 2,753 sqft

    8 Latitude Dr, Winchester, TN

    Tara Hays · Benchmark Realty, LLC

  11. 219 Old Mill Rd — photo33Active

    $349,000

    3 bd · 2 ba · 3,050 sqft

    219 Old Mill Rd, Winchester, TN

    Leanne Kollette Bonning · Benchmark Realty, LLC

  12. 2607 Old Tullahoma Rd — photo49Active

    $464,900

    4 bd · 3 ba · 2,645 sqft

    2607 Old Tullahoma Rd, Winchester, TN

    Elisa Chessor · Century 21 Coffee County Realty & Auction

  13. 1200 Little St — photoPrice Reduced56Active

    $289,000

    5 bd · 2 ba · 1,600 sqft

    1200 Little St, Winchester, TN

    Lori Rowton-Walker · Keller Williams Realty Nashville/Franklin

  14. 128 Bel Aire Dr — photo53Active

    $299,900

    4 bd · 2 ba · 1,923 sqft

    128 Bel Aire Dr, Winchester, TN

    Jessica London · Southern Middle Realty

  15. 92 Hammock Dr — photoPrice Reduced54Active

    $834,000

    4 bd · 4 ba · 2,986 sqft

    92 Hammock Dr, Winchester, TN

    Nicole Miller · Benchmark Realty, LLC

  16. 0 Sisk Rd — photo5Active

    $349,000

    3 bd · 2 ba · 1,600 sqft

    0 Sisk Rd, Winchester, TN

    Angie Miller · John Smith Jr Realty and Auction LLC

  17. 109 Oak Park — photoPrice Reduced37Active

    $429,000

    3 bd · 2 ba · 2,157 sqft

    109 Oak Park, Winchester, TN

    Penny Bowen · Bowen Signature Properties

  18. 318 N Porter St — photoPrice Reduced63Active

    $2,110,900

    4 bd · 6 ba · 6,160 sqft

    318 N Porter St, Winchester, TN

    Tara Hays · Benchmark Realty, LLC

  19. 44 Hammock Dr — photoPrice Reduced60Active

    $499,000

    3 bd · 3 ba · 2,266 sqft

    44 Hammock Dr, Winchester, TN

    Michelle Sampson · Benchmark Realty, LLC

  20. 1543 Paynes Church Rd — photoPrice Reduced36Active

    $315,000

    3 bd · 2 ba · 1,508 sqft

    1543 Paynes Church Rd, Winchester, TN

    Kasidy Lowe | K. Lowe Team · Compass Tennessee, LLC

  21. 1605 Paynes Church Rd — photoPrice Reduced33Active

    $315,000

    3 bd · 2 ba · 1,508 sqft

    1605 Paynes Church Rd, Winchester, TN

    Kasidy Lowe | K. Lowe Team · Compass Tennessee, LLC

  22. 221 Hammock Dr — photo53Active

    $1,199,000

    4 bd · 6 ba · 3,812 sqft

    221 Hammock Dr, Winchester, TN

    Howard Hicks · Benchmark Realty, LLC

  23. 1585 Paynes Church Rd — photoPrice Reduced36Active

    $315,000

    3 bd · 2 ba · 1,508 sqft

    1585 Paynes Church Rd, Winchester, TN

    Kasidy Lowe | K. Lowe Team · Compass Tennessee, LLC

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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.

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Listing data & MLS disclosures

Realtracs
Based on information submitted to the MLS GRID as of 2026-09-26 02:37:00 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.
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #338714

    Call Thomas

    Nearby areas

    ZIP codes

    • 37398 (180)
    • 37388 (173)
    • 37160 (167)
    • 37355 (116)
    • 37387 (54)
    • 37330 (50)
    • 37356 (40)
    • 37380 (31)

    Cities

    • Tullahoma (173)
    • Shelbyville (167)
    • Manchester (116)
    • Tracy City (54)
    • Estill Springs (50)
    • Monteagle (40)
    • South Pittsburg (31)
    • Lynchburg (30)

    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

    July 2026 · This period is still settling

    Winchester 12-month median sale price trend

    Selling at 97.0% of asking price

    Buyers here are paying below asking. MLS · 26 sales · as of Jul 31, 2026

    Homes that sold · County records, as of Jul 10, 2026

    Median sale price
    $407,500$268,000–$606,250 typical range
    Sales
    12
    Paid in cash
    50.0%

    Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

    Median list price
    $480,000
    Homes for sale
    159
    Median days on market
    47 days

    Price trend · Assessor repeat sales, as of Jul 31, 2026

    Year-over-year
    14.0%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

    Median home size
    1,752 sq. ft.