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Winchester, TN Homes for Sale | Realty.com
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3 beds
173 listings
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New construction
With a pool

Homes for Sale in Winchester, TN

Homes for Sale in Winchester, TN

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24 of 173 Listings
Map

Homes for Sale in Winchester, TN

24 of 173 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas
  1. 117 Carol Cir — photo21Active

    $340,000

    3 bd · 2 ba · 1,750 sqft

    117 Carol Cir, Winchester, TN

    Daniel Prince · John Smith Jr Realty and Auction LLC

  2. NewActive

    $215,900

    3 bd · 2 ba · 1,014 sqft

    0 Little St, Winchester, TN

    Daryl Welch · Freedom Realty Group

  3. NewActive

    $215,900

    3 bd · 2 ba · 1,014 sqft

    0 Little St, Winchester, TN

    Daryl Welch · Freedom Realty Group

  4. 135 Chickamauga Trl — photoPrice Reduced36Active

    $328,500

    3 bd · 2 ba · 1,898 sqft

    135 Chickamauga Trl, Winchester, TN

    Angie Miller · John Smith Jr Realty and Auction LLC

  5. 71 Windjammer Ct — photoNew47Active

    $740,000

    4 bd · 4 ba · 3,017 sqft

    71 Windjammer Ct, Winchester, TN

    Ashley Lynch · Lynch Rigsby Realty & Auction, LLC

  6. 292 Ridgecrest Dr — photo62Active

    $649,000

    5 bd · 4 ba · 3,695 sqft

    292 Ridgecrest Dr, Winchester, TN

    Chelsea B. Greenway · Southern Middle Realty

  7. 810 Cumberland Dr — photo52Active

    $399,900

    3 bd · 2 ba · 2,260 sqft

    810 Cumberland Dr, Winchester, TN

    Matt Sargent · Matt Sargent Homes

  8. 107 Brandi Way — photo21Active

    $1,500,000

    3 bd · 2 ba · 2,962 sqft

    107 Brandi Way, Winchester, TN

    Jackson Carroll · Compass

  9. 206 Homeward Ave — photo40Active

    $299,900

    4 bd · 2 ba · 1,999 sqft

    206 Homeward Ave, Winchester, TN

    Tekesha Fuqua-Taylor · Keller Williams Realty - Murfreesboro

  10. 0 Style St — photo1Active

    $239,000

    3 bd · 2 ba · 1,100 sqft

    0 Style St, Winchester, TN

    Stephanie Jo Dowdy · Freedom Realty Group

  11. Active

    $215,900

    3 bd · 2 ba · 1,014 sqft

    0 Little St, Winchester, TN

    Stephanie Jo Dowdy · Freedom Realty Group

  12. 2124 Boswell Rd — photoPrice Reduced71Active

    $999,500

    4 bd · 4 ba · 6,803 sqft

    2124 Boswell Rd, Winchester, TN

    Robert Evanoff · Berkshire Hathaway HomeServices Woodmont Realty

  13. 1790 Old Estill Springs Rd — photo32Active

    $299,000

    3 bd · 2 ba · 1,675 sqft

    1790 Old Estill Springs Rd, Winchester, TN

    Steven Paul · Keller Williams West Knoxville

  14. 366 Oak Leaf Cir — photo28Active

    Price unavailable

    3 bd · 2 ba · 1,672 sqft

    366 Oak Leaf Cir, Winchester, TN

    Jack Cooter · Maples Realty & Auction Co.

  15. 108 Lookout Drive — photo49Active

    $443,900

    3 bd · 2 ba · 2,290 sqft

    108 Lookout Drive, Winchester, TN

    MITCHELL BOWMAN · simpliHOM - The Results Team

  16. 124 Lookout Drive — photo53Active

    $424,900

    4 bd · 2 ba · 1,890 sqft

    124 Lookout Drive, Winchester, TN

    MITCHELL BOWMAN · simpliHOM - The Results Team

  17. 102 Oak Park — photoPrice Reduced41Active

    $269,900

    2 bd · 1 ba · 1,373 sqft

    102 Oak Park, Winchester, TN

    Shelia Lunsford · Benchmark Realty, LLC

  18. 208 Lillian St — photo26Active

    $199,500

    3 bd · 1 ba · 1,326 sqft

    208 Lillian St, Winchester, TN

    Cramer Foster · Lynch Rigsby Realty & Auction, LLC

  19. 160 Wakeboard Way — photo62Active

    $1,199,900

    4 bd · 4 ba · 3,720 sqft

    160 Wakeboard Way, Winchester, TN

    Angela Privett · Benchmark Realty, LLC

  20. listing photo54Active

    $299,000

    5 bd · 2 ba · 1,588 sqft

    Address withheld · Winchester, TN

    Lori Rowton · Keller Williams Nashville-Franklin

  21. 24 Kacey Marie Dr — photo51Active

    $639,000

    3 bd · 4 ba · 2,977 sqft

    24 Kacey Marie Dr, Winchester, TN

    Ashton Staker · eXp Realty

  22. 115 7th Ave NE — photo33Active

    $319,000

    3 bd · 2 ba · 1,308 sqft

    115 7th Ave NE, Winchester, TN

    David Janke · Canopy Real Estate

  23. Active

    $580,458

    3 bd · 2 ba · 2,274 sqft

    0 Deer Valley, Winchester, TN

    Angela Privett · Benchmark Realty, LLC

  24. 76 Chase Cir — photo42Active

    $369,900

    2 bd · 2 ba · 1,818 sqft

    76 Chase Cir, Winchester, TN

    Sean Crabtree · Blue Door Realty Group

12…8

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Listing data & MLS disclosures

Greater Chattanooga REALTORS
IDX information is provided exclusively for consumers’ personal, noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data is deemed reliable but is not guaranteed accurate by the MLS.
Listing information ©2026 Greater Chattanooga Association of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-09-03 15:13:53 UTC
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Based on information submitted to the MLS GRID as of 2026-09-09 20:58:41 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.
  • By feature

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #338714

    Call Thomas

    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

    Nearby areas

    ZIP codes

    • 37398 (160)
    • 37388 (150)
    • 37160 (149)
    • 37355 (110)
    • 37387 (49)
    • 37330 (44)
    • 37356 (44)
    • 37324 (33)

    Cities

    • Tullahoma (150)
    • Shelbyville (149)
    • Manchester (110)
    • Tracy City (49)
    • Monteagle (44)
    • Estill Springs (43)
    • Decherd (33)
    • Lynchburg (29)

    Winchester housing market

    June 2026

    Winchester 12-month median sale price trend

    Selling at 97.5% of asking price

    Buyers here are paying below asking. MLS · 36 sales · as of Jun 30, 2026

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

    Median sale price
    $323,000$198,000–$486,500 typical range
    Price per sq. ft.
    $200
    Sales
    55
    Paid in cash
    49.1%

    Homes on the market · MLS, as of Jun 30, 2026

    Median days on market
    31 days

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

    Year-over-year
    25.9%