9,889

Winchester, TN Homes

Section Image Section Image
    • /34

      Est $536,357 Not Listed For Sale

      267 Bryan Dr, Winchester, TN 37398

      • 4 Beds
      • 2 Baths
      • 2,350 Sq Ft
      • Built 2018
      267 Bryan Dr, Winchester, TN 37398

      Last Sold Summary

      • 5% Above List Price
      • $217/SF
      • 132 Days On Market

      Last Sold Price $509,000

      Last Listing Agent Nick Edenfield Keller Williams Realty

  • /3

    $76,900

    • Land
    • 0.15 Acre
    • $512,667 per Acre

    0 Deer Valley Cir Unit RTC2980754, Winchester, TN 37398

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 271-5914

    0 Deer Valley Cir Unit RTC2980754, Winchester, TN 37398
  • /3

    $73,750 Sold Feb 18, 2026

    0 Deer Valley Cir Unit RTC2980801, Winchester, TN 37398

    • Land
    • 0.39 Acre
    • $189,103 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 169 Days On Market

    Last Listing Agent Ashley Lynch Lynch Rigsby Realty & Auction, LLC

    0 Deer Valley Cir Unit RTC2980801, Winchester, TN 37398
    • /29

      Est $368,690 Not Listed For Sale

      23 Anderton Dr, Winchester, TN 37398

      • 3 Beds
      • 2.5 Baths
      • 1,891 Sq Ft
      • Built 2008
      23 Anderton Dr, Winchester, TN 37398

      Last Sold Summary

      • 4% Below List Price
      • $204/SF
      • 13 Days On Market

      Last Sold Price $385,500

      Last Listing Agent Angela Privett Benchmark Realty, LLC

  • /8

    $149,900

    • Land
    • 0.29 Acre
    • $516,897 per Acre

    0 Twin Creeks Dr Unit RTC2685254, Winchester, TN 37398

    One of the prettiest lake communities in Tennessee! Privately Gated and located at Tims Ford Lake. Exclusive community amenities include beautiful walking trails, full service marina with dock and boat slip rentals, clubhouse, heated pools, event center, boat club and boat rentals. Waterfront dining available at Drafts & Watercrafts. Lake life living at it's finest!

    Agent Photo

    Joe Orr

    WEICHERT, REALTORS Joe Orr & Associates

    (931) 283-5443

    0 Twin Creeks Dr Unit RTC2685254, Winchester, TN 37398
  • /13

    $600,000 Sold Aug 07, 2025

    0 Abby Cir Unit RTC2696850, Winchester, TN 37398

    • Land
    • 0.62 Acre
    • $967,742 per Acre

    Last Sold Summary

    • 23% Below List Price
    • 311 Days On Market

    Last Listing Agent Sam Hatfield Sam Hatfield Realty, Inc.

    0 Abby Cir Unit RTC2696850, Winchester, TN 37398
    • /21

      Est $271,017 Not Listed For Sale

      233 Duncan Ln, Winchester, TN 37398

      • 4 Beds
      • 2 Baths
      • 1,924 Sq Ft
      • Built 1991
      233 Duncan Ln, Winchester, TN 37398

      Last Sold Summary

      • 5% Below List Price
      • $148/SF
      • 13 Days On Market

      Last Sold Price $285,000

      Last Listing Agent Stan Beech Zach Taylor Real Estate

  • /37

    $459,900

    • 3 Beds
    • 2.5 Baths
    • 2,688 Sq Ft

    102 Dogwood Ln, Winchester, TN 37398

    WOW!! This brick ranch has been completely renovated and remodeled and you have got to see it to believe it!! All new custom kitchen with gorgeous cabinets, floating shelves, large island, farmhouse sink, granite countertops and pantry. Large LR/Dining room combination, den with electric fireplace, 3 oversized bedrooms with large closets, new bathrooms, and an extra flex space that could be a

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 546-1055

    102 Dogwood Ln, Winchester, TN 37398
  • /32

    $309,000 Sold Mar 06, 2026

    25 Glasner Ln, Winchester, TN 37398

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 2025

    Last Sold Summary

    • 8% Below List Price
    • $206/SF
    • 102 Days On Market

    Current Estimated Value $307,434

    Last Listing Agent Thomas Ore Winton Auction & Realty Co.

    25 Glasner Ln, Winchester, TN 37398
    • /22

      Est $165,679 Not Listed For Sale

      715 Lynwood St Unit 717, Winchester, TN 37398

      • Studio
      • 1,664 Sq Ft
      • Built 1986
      715 Lynwood St Unit 717, Winchester, TN 37398

      Last Sold Summary

      • 1% Above List Price
      • $99/SF
      • 32 Days On Market

      Last Sold Price $164,000

      Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  • /41

    $589,000

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft

    18 Shady Cove Ln, Winchester, TN 37398

    Newer build in the quiet, wooded Hopkins Point Subdivision offering strong investment potential and privacy. This low-maintenance, corner-lot home is currently operating as a short-term rental, and is being sold furnished for a true turn-key opportunity. The main level features 3 bedrooms, 2 full baths, an open layout, and a whole-home water purification system. The unfinished walkout basement

    Agent Photo

    Jennifer Cummings

    SimpliHOM

    (931) 283-6984

    18 Shady Cove Ln, Winchester, TN 37398
  • /10

    $95,000 Sold May 28, 2025

    512 Elm St, Winchester, TN 37398

    • 2 Beds
    • 1 Bath
    • 948 Sq Ft
    • Built 1942

    Last Sold Summary

    • $100/SF
    • 8 Days On Market

    Current Estimated Value $105,128

    Last Listing Agent Bj Rigsby Lynch Rigsby Realty & Auction, LLC

    512 Elm St, Winchester, TN 37398
    • /12

      Est $118,088 Not Listed For Sale

      140 Carson Ln, Winchester, TN 37398

      • 2 Beds
      • 1.5 Baths
      • 672 Sq Ft
      • Built 1965
      140 Carson Ln, Winchester, TN 37398

      Last Sold Summary

      • 82% Above List Price
      • $97/SF
      • 113 Days On Market

      Last Sold Price $65,000

      Last Listing Agent April Smith John Smith Jr Realty and Auction LLC

  • /3

    $69,900

    • Land
    • 0.15 Acre
    • $466,000 per Acre

    0 Deer Valley Cir Unit RTC2980805, Winchester, TN 37398

    Welcome to your next opportunity in this brand-new, gated 55+ community designed for comfort, convenience, and connection! Choose your perfect spot and create a home that fits your lifestyle. This thoughtfully planned neighborhood will include a beautifully appointed clubhouse, swimming pool, fitness center, and a dedicated dog park—perfect for active, social living. Don't miss this opportunity-

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 429-0901

    0 Deer Valley Cir Unit RTC2980805, Winchester, TN 37398
  • /10

    $140,000 Sold Aug 04, 2025

    411 Style St, Winchester, TN 37398

    • 3 Beds
    • 1 Bath
    • 888 Sq Ft
    • Built 1945

    Last Sold Summary

    • 10% Below List Price
    • $158/SF
    • 52 Days On Market

    Current Estimated Value $145,048

    Last Listing Agent Angela Miller John Smith Jr Realty and Auction LLC

    411 Style St, Winchester, TN 37398
    • /68

      Est $822,135 Not Listed For Sale

      290 Cascade Dr, Winchester, TN 37398

      • 4 Beds
      • 2.5 Baths
      • 3,858 Sq Ft
      • Built 2010
      290 Cascade Dr, Winchester, TN 37398

      Last Sold Summary

      • 3% Above List Price
      • $207/SF
      • 62 Days On Market

      Last Sold Price $799,500

      Last Listing Agent Jessica London Southern Middle Realty

  • /23

    $219,900

    • 3 Beds
    • 2 Baths
    • 2,040 Sq Ft

    1110 Hunt St, Winchester, TN 37398

    Welcome home to this spacious 2,040 sq ft double-wide on a permanent foundation! This home features large bedrooms throughout, each with a walk in closets, offering plenty of space and storage. The kitchen offers an abundance of countertop space and cabinets, along with a large island - perfect for cooking, gathering, and entertaining. This home offers generous living space and wood burning

    Agent Photo

    Shawna Denby

    1st Choice REALTOR

    (931) 416-1870

    1110 Hunt St, Winchester, TN 37398
  • /55

    $1,225,000 Sold Jul 29, 2025

    668 Bluff Dr, Winchester, TN 37398

    • 2 Beds
    • 2.5 Baths
    • 3,076 Sq Ft
    • Built 1994

    Last Sold Summary

    • 17% Below List Price
    • $398/SF
    • 78 Days On Market

    Current Estimated Value $1,302,721

    Last Listing Agent Sam Hatfield Sam Hatfield Realty, Inc.

    668 Bluff Dr, Winchester, TN 37398
    • /68

      Est $565,204 Not Listed For Sale

      106 Magrath Rd, Winchester, TN 37398

      • 4 Beds
      • 4 Baths
      • 2,952 Sq Ft
      • Built 2009
      106 Magrath Rd, Winchester, TN 37398

      Last Sold Summary

      • 2% Below List Price
      • $195/SF
      • 12 Days On Market

      Last Sold Price $575,000

      Last Listing Agent John Peck Peck Realty Group, LLC

  • /3

    $76,900

    • Land
    • 0.17 Acre
    • $452,353 per Acre

    0 Deer Valley Cir Unit RTC2980808, Winchester, TN 37398

    Welcome to your next opportunity in this brand-new, gated 55+ community designed for comfort, convenience, and connection! Choose your perfect spot and create a home that fits your lifestyle. This thoughtfully planned neighborhood will include a beautifully appointed clubhouse, swimming pool, fitness center, and a dedicated dog park—perfect for active, social living. Don't miss this opportunity-

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 391-3042

    0 Deer Valley Cir Unit RTC2980808, Winchester, TN 37398
  • /75

    $455,000 Sold Feb 11, 2026

    105 Island Way, Winchester, TN 37398

    • 3 Beds
    • 2.5 Baths
    • 2,631 Sq Ft
    • Built 2019

    Last Sold Summary

    • 9% Below List Price
    • $173/SF
    • 354 Days On Market

    Current Estimated Value $460,522

    Last Listing Agent Billie Kay Caldwell Swaffords Property Shop

    105 Island Way, Winchester, TN 37398
    • /40

      Est $513,846 Not Listed For Sale

      1070 Liberty Rd, Winchester, TN 37398

      • 3 Beds
      • 2.5 Baths
      • 2,172 Sq Ft
      • Built 2010
      1070 Liberty Rd, Winchester, TN 37398

      Last Sold Summary

      • 7% Below List Price
      • $253/SF
      • 173 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Robert Evanoff Berkshire Hathaway HomeServices Woodmont Realty

  • /67

    $1,599,000

    • 5 Beds
    • 4.5 Baths
    • 3,797 Sq Ft

    1750 Awalt Dr, Winchester, TN 37398

    This modern and upscale lakefront property on Tims Ford Lake is one you do not want to miss! From the bold architectural finishes and modern design to the functionality and lakeview retreat this place is one to call home. The main home offers 4 bedrooms and 3.5 baths with a beautiful, stacked stone fireplace and natural stained hardwood floors, a gourmet kitchen & media room, and an attached

    Agent Photo

    Chelsea Greenway

    Winton Auction & Realty Co.

    (931) 342-4168

    1750 Awalt Dr, Winchester, TN 37398
  • /30

    $350,000 Sold Sep 02, 2025

    147 Crimson Dr, Winchester, TN 37398

    • 3 Beds
    • 2 Baths
    • 1,773 Sq Ft
    • Built 2016

    Last Sold Summary

    • 8% Below List Price
    • $197/SF
    • 64 Days On Market

    Current Estimated Value $367,315

    Last Listing Agent John Peck Peck Realty Group, LLC

    147 Crimson Dr, Winchester, TN 37398
    • /9

      Est $180,729 Not Listed For Sale

      107 Sipes St, Winchester, TN 37398

      • 3 Beds
      • 1 Bath
      • 1,125 Sq Ft
      • Built 1953
      107 Sipes St, Winchester, TN 37398

      Last Sold Summary

      • 3% Above List Price
      • $156/SF
      • 43 Days On Market

      Last Sold Price $175,000

      Last Listing Agent Matthew Joachim Zach Taylor Real Estate

  • /3

    $69,900

    • Land
    • 0.15 Acre
    • $466,000 per Acre

    0 Deer Valley Cir Unit RTC2980794, Winchester, TN 37398

    Welcome to your next opportunity in this brand-new, gated 55+ community designed for comfort, convenience, and connection! Choose your perfect spot and create a home that fits your lifestyle. This thoughtfully planned neighborhood will include a beautifully appointed clubhouse, swimming pool, fitness center, and a dedicated dog park—perfect for active, social living. Don't miss this opportunity-

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 313-8991

    0 Deer Valley Cir Unit RTC2980794, Winchester, TN 37398
  • /40

    $380,000 Sold Mar 12, 2026

    189 Pickney Rd, Winchester, TN 37398

    • 3 Beds
    • 2 Baths
    • 2,607 Sq Ft
    • Built 1970

    Last Sold Summary

    • 4% Below List Price
    • $146/SF
    • 60 Days On Market

    Current Estimated Value $376,412

    Last Listing Agent Debbie DeLoach Crye-Leike, Realtors

    189 Pickney Rd, Winchester, TN 37398
    • /34

      Est $275,016 Not Listed For Sale

      174 Apple Dr, Winchester, TN 37398

      • 4 Beds
      • 2 Baths
      • 1,521 Sq Ft
      • Built 2009
      174 Apple Dr, Winchester, TN 37398

      Last Sold Summary

      • 9% Above List Price
      • $165/SF
      • 19 Days On Market

      Last Sold Price $251,237

      Last Listing Agent Houston Poston BHHS Southern Routes Realty

  • /78

    $789,900

    • 4 Beds
    • 3.5 Baths
    • 3,896 Sq Ft

    630 Shadowbrook Rd, Winchester, TN 37398

    Experience unparalleled craftsmanship in this stunning estate situated on over an acre of private, picturesque grounds. This meticulously maintained home features 3 spacious bedrooms, each boasting its own private ensuite bathroom for ultimate comfort and privacy. A 4th bedroom is upstairs and currently being used as an office. The interior is a showcase of architectural detail, defined by custom

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 208-4110

    630 Shadowbrook Rd, Winchester, TN 37398
  • /17

    $193,000 Sold May 01, 2025

    0 Kayak Way Unit RTC2780325, Winchester, TN 37398

    • Land

    Last Sold Summary

    • 8% Below List Price
    • 64 Days On Market

    Last Listing Agent Felicia Wright Leading Edge Real Estate Group

    0 Kayak Way Unit RTC2780325, Winchester, TN 37398
    • /15

      Est $150,761 Not Listed For Sale

      816 Mason Ave, Winchester, TN 37398

      • 3 Beds
      • 1 Bath
      • 808 Sq Ft
      • Built 1950
      816 Mason Ave, Winchester, TN 37398

      Last Sold Summary

      • 8% Above List Price
      • $173/SF
      • 50 Days On Market

      Last Sold Price $140,000

      Last Listing Agent Sean Crabtree Blue Door Realty Group

  • /3

    $76,900

    • Land
    • 0.15 Acre
    • $512,667 per Acre

    0 Deer Valley Cir Unit RTC2980756, Winchester, TN 37398

    Welcome to your next opportunity in this brand-new, gated 55+ community designed for comfort, convenience, and connection! Choose your perfect spot and create a home that fits your lifestyle. This thoughtfully planned neighborhood will include a beautifully appointed clubhouse, swimming pool, fitness center, and a dedicated dog park—perfect for active, social living. Don't miss this opportunity-

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 277-6057

    0 Deer Valley Cir Unit RTC2980756, Winchester, TN 37398
  • /40

    $315,000 Sold Mar 20, 2026

    209 Franklin Park, Winchester, TN 37398

    • 3 Beds
    • 2 Baths
    • 2,053 Sq Ft
    • Built 1958

    Last Sold Summary

    • 3% Below List Price
    • $153/SF
    • 24 Days On Market

    Current Estimated Value $315,156

    Last Listing Agent Hannah Monilaw Better Homes & Gardens Real Estate Heritage Group

    209 Franklin Park, Winchester, TN 37398
    • /86

      Est $856,842 Not Listed For Sale

      264 Cascade Dr, Winchester, TN 37398

      • 5 Beds
      • 3.5 Baths
      • 3,729 Sq Ft
      • Built 2008
      264 Cascade Dr, Winchester, TN 37398

      Last Sold Summary

      • 3% Below List Price
      • $238/SF
      • 60 Days On Market

      Last Sold Price $887,000

      Last Listing Agent Jessica London Southern Middle Realty

  • /51

    $549,900 Pending

    • 6 Beds
    • 4 Baths
    • 8,508 Sq Ft

    974 Lynchburg Rd, Winchester, TN 37398

    Former Antebellum Inn which offers so much potential. Now Magnolia Hill Manor

    Agent Photo

    John Peck

    Peck Realty Group, LLC

    (931) 416-0673

    974 Lynchburg Rd, Winchester, TN 37398
  • /2

    $55,000 Sold Aug 13, 2025

    0 Old Tullahoma Rd Unit RTC2967842, Winchester, TN 37398

    • Land
    • 1.27 Acres
    • $43,307 per Acre

    Last Sold Summary

    • 15% Below List Price

    Last Listing Agent Mitch Umbarger Better Homes & Gardens Real Estate Heritage Group

    0 Old Tullahoma Rd Unit RTC2967842, Winchester, TN 37398
    • /32

      Est $295,015 Not Listed For Sale

      1322 Marble Hill Rd, Winchester, TN 37398

      • 4 Beds
      • 1 Bath
      • 2,138 Sq Ft
      • Built 1930
      1322 Marble Hill Rd, Winchester, TN 37398

      Last Sold Summary

      • 44% Above List Price
      • $96/SF
      • 10 Days On Market

      Last Sold Price $205,000

      Last Listing Agent Joe Orr WEICHERT, REALTORS Joe Orr & Associates

  • /3

    $76,900

    • Land
    • 0.17 Acre
    • $452,353 per Acre

    0 Deer Valley Cir Unit RTC2980817, Winchester, TN 37398

    Welcome to your next opportunity in this brand-new, gated 55+ community designed for comfort, convenience, and connection! Choose your perfect spot and create a home that fits your lifestyle. This thoughtfully planned neighborhood will include a beautifully appointed clubhouse, swimming pool, fitness center, and a dedicated dog park—perfect for active, social living. Don't miss this opportunity-

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 281-7122

    0 Deer Valley Cir Unit RTC2980817, Winchester, TN 37398
  • /54

    $185,900 Sold Jul 14, 2025

    408 Style St, Winchester, TN 37398

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • Built 1957

    Last Sold Summary

    • $117/SF
    • 40 Days On Market

    Current Estimated Value $251,433

    Last Listing Agent Darrell Potts United Country - Columbia Realty & Auction

    408 Style St, Winchester, TN 37398
    • /4

      Est $191,652 Not Listed For Sale

      1770 Short Creek Rd, Winchester, TN 37398

      • Built 1900
      1770 Short Creek Rd, Winchester, TN 37398

      Last Sold Summary

      • 60% Above List Price
      • $55/SF
      • 364 Days On Market

      Last Sold Price $120,000

      Last Listing Agent James Sutton SUTTON REALTY CO.

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home