10,003

Winchester, TN Homes

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  • /30

    $115,000

    • Land
    • 15,246 Sq Ft
    • $328,571 per Acre

    0 Driftwood Ct Unit 389, Winchester, TN 37398

    The lake is calling your name! This large, corner lot is everything you've been looking for to build your dream lake house on. Twin Creeks community offers lake access, community beach, heated pool open year round, firepits, walking trails, marina, and so much more! Call today to lock in this dream lot!

    Katie Garrison Barlow Realty LLC

    0 Driftwood Ct Unit 389, Winchester, TN 37398
  • /53

    $795,000

    Sold Nov 04, 2025

    190 Cascade Dr, Winchester, TN 37398

    • 4 Beds
    • 3.5 Baths
    • 3,515 Sq Ft
    • Built 2009

    Last Sold Summary

    • 10% Below List Price
    • $226/SF
    • 200 Days On Market

    Current Estimated Value $860,048

    Last Listing Agent Rachel Ferrell Southern Middle Realty

    190 Cascade Dr, Winchester, TN 37398
    • /30

      Est $499,576

      Not Listed For Sale

      743 Hopkins Ln, Winchester, TN 37398

      • 3 Beds
      • 2 Baths
      • 2,457 Sq Ft
      • Built 1995
      743 Hopkins Ln, Winchester, TN 37398

      Last Sold Summary

      • 214 Days On Market

      Last Listing Agent Tyler Henley Franklin County Realty

  • /80

    $1,775,000

    $75K PRICE DROP
    • 6 Beds
    • 3.5 Baths
    • 3,617 Sq Ft

    3539 Liberty Rd, Winchester, TN 37398

    Exceptional property on 10.5 sprawling acres offering the perfect blend of space, comfort, and resort style outdoor living. The main residence features 3,617 sq. ft. with 6 bed, 3.5 baths, providing ample room for family, guests, and entertaining. The well appointed kitchen showcases beautiful hickory cabinetry, black stainless steel appliances, quartz countertops, abundant storage and generous

    Chesney Luttrell John Smith Jr Realty and Auction LLC

    3539 Liberty Rd, Winchester, TN 37398
  • /35

    $235,000

    Sold Jan 12, 2026

    136 Bel Aire Dr, Winchester, TN 37398

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft
    • Built 1964

    Last Sold Summary

    • 18% Below List Price
    • $121/SF
    • 187 Days On Market

    Current Estimated Value $251,487

    Last Listing Agent Sharon Swafford Swaffords Property Shop

    136 Bel Aire Dr, Winchester, TN 37398
    • /70

      Est $2,810,227

      Not Listed For Sale

      51 W Rockcrest Cir, Winchester, TN 37398

      • 3 Beds
      • 6.5 Baths
      • 7,901 Sq Ft
      • Built 2006
      51 W Rockcrest Cir, Winchester, TN 37398

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Marla Richardson Parks Compass

  • /57

    $840,900

    $36K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,484 Sq Ft

    282 Owl Hollow Ln, Winchester, TN 37398

    VERY MOTVATED SELLER, Beautiful Lake house perfect for multi families. A cozy fireplace adds a touch of warmth and charm to the inviting living space. w/master located on top floor w/custom walk-in shower, oversized Jacuzzi tub and private entrance to the covered deck. 2 guest rooms upstairs, and extra guest suite downstairs and lots of open space for entertaining, back patio for relaxing

    Sam Hatfield Sam Hatfield Realty, Inc.

    282 Owl Hollow Ln, Winchester, TN 37398
  • /34

    $270,000

    Sold Dec 03, 2025

    805 S Shephard St, Winchester, TN 37398

    • 3 Beds
    • 2 Baths
    • 1,310 Sq Ft
    • Built 2025

    Last Sold Summary

    • 5% Below List Price
    • $206/SF
    • 99 Days On Market

    Last Listing Agent Pelatiah Prince Winton Auction & Realty Co.

    805 S Shephard St, Winchester, TN 37398
    • /29

      Est $349,705

      Not Listed For Sale

      86 Royal Oak Dr, Winchester, TN 37398

      • 3 Beds
      • 3 Baths
      • 1,847 Sq Ft
      • Built 1977
      86 Royal Oak Dr, Winchester, TN 37398

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Ann Hoke Huffaker & Hoke Realty Partners

  • /54

    $489,900

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 3,084 Sq Ft

    378 Crimson Dr, Winchester, TN 37398

    Space, comfort, and features you’ll appreciate from the moment you walk in! This spacious 4-bedroom, 2.5-bath home offers a spacious open-concept layout with plenty of room for everyday living and entertaining. The large hobby room offers flexible space for a pool table, workshop, craft room, home office, or whatever fits your lifestyle. The primary bath has been beautifully renovated bath with

    Pamela Carver Southern Middle Realty

    378 Crimson Dr, Winchester, TN 37398
  • /49

    $220,000

    Sold Dec 12, 2025

    190 Cheyenne Ave, Winchester, TN 37398

    • 3 Beds
    • 2 Baths
    • 1,118 Sq Ft
    • Built 1998

    Last Sold Summary

    • 4% Below List Price
    • $197/SF
    • 22 Days On Market

    Current Estimated Value $227,546

    Last Listing Agent Rachel Ferrell Southern Middle Realty

    190 Cheyenne Ave, Winchester, TN 37398
    • /16

      Est $271,097

      Not Listed For Sale

      854 Mingo Rd, Winchester, TN 37398

      • 3 Beds
      • 1.5 Baths
      • 2,158 Sq Ft
      • Built 1966
      854 Mingo Rd, Winchester, TN 37398

      Last Sold Summary

      • 90 Days On Market

      Last Listing Agent Landon Keller Century 21 Volunteer Realty

  • /65

    $385,000

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft

    1522 Holders Cove Rd, Winchester, TN 37398

    Welcome to 1522 Holders Cove Road, a truly unique, fully updated, single-level ranch offering a backyard paradise that embodies the American dream. Situated on nearly 1.5 private acres, this move-in-ready home offers the ideal blend of peaceful privacy and everyday convenience, located just minutes from downtown Winchester's shopping, dining, and local attractions.Inside, you will

    Wade Trammell Keller Williams Realty

    1522 Holders Cove Rd, Winchester, TN 37398
  • /41

    $349,900

    Sold Jul 20, 2026

    2425 Old Tullahoma Rd, Winchester, TN 37398

    • 3 Beds
    • 2 Baths
    • 1,567 Sq Ft
    • Built 2018

    Last Sold Summary

    • $223/SF
    • 6 Days On Market

    Current Estimated Value $348,746

    Last Listing Agent Greg Sitz Parks Auction & Realty

    2425 Old Tullahoma Rd, Winchester, TN 37398
    • /31

      Est $428,446

      Not Listed For Sale

      142 Dry Creek Ln, Winchester, TN 37398

      • 3 Beds
      • 2 Baths
      • 2,166 Sq Ft
      • Built 1987
      142 Dry Creek Ln, Winchester, TN 37398

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Tara Smith Better Homes & Gardens Real Estate Heritage Group

  • /5

    $177,000

    $43K PRICE DROP
    • Land
    • 3.16 Acres
    • $56,013 per Acre

    5 Anderton Dr, Winchester, TN 37398

    Tims Ford Lake WATER VIEW large lot. 3.16 acreLot. AMAZING water views. water access very very close. Hard to find LARGE LOT near the Lake. Build your custom dream home on this beautiful, year round water view site. This lot is situated on a private driveway access and enjoys additional privacy with Tim’s Ford State Park property next door. Enjoy 180-degree view of beautiful Tims Ford Lake and

    isaac zimmerle Benchmark Realty, LLC

    5 Anderton Dr, Winchester, TN 37398
  • /36

    $585,000

    Sold Aug 11, 2026

    124 Barefoot Way, Winchester, TN 37398

    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft
    • Built 2022

    Last Sold Summary

    • 13% Below List Price
    • $317/SF
    • 127 Days On Market

    Current Estimated Value $572,200

    Last Listing Agent Marla Richardson Parks Compass

    124 Barefoot Way, Winchester, TN 37398
    • /3

      Est $352,952

      Not Listed For Sale

      74 Freedom Ln, Winchester, TN 37398

      • 3 Beds
      • 2 Baths
      • 2,244 Sq Ft
      • Built 1973
      74 Freedom Ln, Winchester, TN 37398

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Todd Davidson Parks Auction & Realty

  • /89

    $1,050,000

    $145K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,906 Sq Ft

    208 Loop Dr, Winchester, TN 37398

    Welcome to Luxury Lake Life on Tims Ford Lake!! Discover refined waterfront living with this stately brick home complete with your very own private boat dock. Boasting 4 spacious bedrooms and 3.5 beautifully appointed bathrooms, this home offers the perfect blend of elegance and comfort. Step inside to find exquisite custom trim and architectural details throughout. The culinary kitchen is a

    Jessica London Southern Middle Realty

    208 Loop Dr, Winchester, TN 37398
  • /47

    $485,000

    Sold Nov 24, 2025

    105 Twilight Dr, Winchester, TN 37398

    • 4 Beds
    • 2.5 Baths
    • 3,570 Sq Ft
    • Built 1989

    Last Sold Summary

    • 3% Below List Price
    • $136/SF
    • 20 Days On Market

    Current Estimated Value $515,009

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

    105 Twilight Dr, Winchester, TN 37398
    • /50

      Est $500,243

      Not Listed For Sale

      517 Lakeview Way, Winchester, TN 37398

      • 3 Beds
      • 2.5 Baths
      • 2,382 Sq Ft
      • Built 1987
      517 Lakeview Way, Winchester, TN 37398

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent John Smith, Jr. John Smith Jr Realty and Auction LLC

  • /4

    $57,900

    $7K PRICE DROP
    • Land
    • 23,958 Sq Ft
    • $105,273 per Acre

    66 Edgefield Ct, Winchester, TN 37398

    New Gated Community, The Highlands! Located less than one minute from Tims Ford Lake (public boat launch on Sharp Springs Rd). Convenient to shopping and dining.

    Sharon Swafford Swaffords Property Shop

    66 Edgefield Ct, Winchester, TN 37398
  • /30

    $478,000

    Sold Jan 16, 2026

    159 Canoe Ct, Winchester, TN 37398

    • 4 Beds
    • 2.5 Baths
    • 2,232 Sq Ft
    • Built 2024

    Last Sold Summary

    • 4% Below List Price
    • $214/SF
    • 68 Days On Market

    Last Listing Agent Earin Smotherman Reliant Realty ERA Powered

    159 Canoe Ct, Winchester, TN 37398
    • /37

      Est $433,581

      Not Listed For Sale

      150 Michelle Ln, Winchester, TN 37398

      • 3 Beds
      • 2 Baths
      • 2,032 Sq Ft
      • Built 1972
      150 Michelle Ln, Winchester, TN 37398

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Jarad Shetters Synergy Realty Network, LLC

  • /17

    $70,000

    • Land
    • 6,534 Sq Ft
    • $466,667 per Acre

    Lot 286 Lake Life Ct, Winchester, TN 37398

    Welcome to your dream lot and the beginning of a complete lakeside lifestyle. Residents enjoy access to multiple community pools, a full-service marina with dock and boat slip rentals, and a waterfront restaurant for elevated dining without leaving the neighborhood. The Honeysuckle, an elegant pavilion, provides a refined setting for private events and gatherings, while Firefly Point offers a

    Eric Taylor A.H. Sothebys Int. Realty

    Lot 286 Lake Life Ct, Winchester, TN 37398
  • /4

    $741,300

    Sold Nov 19, 2025

    0 Old Tullahoma Rd Unit RTC3048163, Winchester, TN 37398

    Last Sold Summary

    Last Listing Agent Shawna Denby 1st Choice REALTOR

    0 Old Tullahoma Rd Unit RTC3048163, Winchester, TN 37398
    • /57

      Est $566,530

      Not Listed For Sale

      101 Farris Rd, Winchester, TN 37398

      • 3 Beds
      • 3 Baths
      • 2,231 Sq Ft
      • Built 1991
      101 Farris Rd, Winchester, TN 37398

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Melissa Stewart Swaffords Property Shop

  • /48

    $1,750,000

    903 Old Estill Springs Rd, Winchester, TN 37398

    Exceptional 47.5± acre residential development opportunity in the heart of Winchester, TN. This predominantly level, well-drained farm offers frontage on Old Estill Springs Rd., Bible Crossing Rd., and Myers Rd., providing multiple access points for a future subdivision or master-planned community. Adjacent to Winchester City Park, the property presents a rare opportunity to create a

    Thomas Ore Winton Auction & Realty Co.

    903 Old Estill Springs Rd, Winchester, TN 37398
  • /7

    $94,000

    Sold Jun 24, 2026

    0 Golf Shores Dr Unit RTC3208495, Winchester, TN 37398

    • Land
    • 0 Sq Ft

    Last Sold Summary

    • 5% Below List Price
    • 3 Days On Market

    Last Listing Agent Chris Hawkersmith Lynch Rigsby Realty & Auction, LLC

    0 Golf Shores Dr Unit RTC3208495, Winchester, TN 37398
    • /30

      Est $264,443

      Not Listed For Sale

      2435 Water Tank Rd, Winchester, TN 37398

      • 3 Beds
      • 2 Baths
      • 1,255 Sq Ft
      • Built 1991
      2435 Water Tank Rd, Winchester, TN 37398

      Last Sold Summary

      • 97 Days On Market

      Last Listing Agent Sheila Campbell eXp Realty

  • /17

    $70,000

    • Land
    • 0 Sq Ft

    0 Lake Life Ct Unit 286, Winchester, TN 37398

    Welcome to your dream lot and the beginning of a complete lakeside lifestyle. Residents enjoy access to multiple community pools, a full-service marina with dock and boat slip rentals, and a waterfront restaurant for elevated dining without leaving the neighborhood. The Honeysuckle, an elegant pavilion, provides a refined setting for private events and gatherings, while Firefly Point offers a

    Eric Taylor Amanda Howard Sothebys International Realty

    0 Lake Life Ct Unit 286, Winchester, TN 37398
  • /63

    $515,000

    Sold Jul 17, 2026

    249 Lookout Dr, Winchester, TN 37398

    • 3 Beds
    • 2.5 Baths
    • 2,973 Sq Ft
    • Built 2025

    Last Sold Summary

    • 10% Below List Price
    • $173/SF
    • 295 Days On Market

    Last Listing Agent Charlie Gonzales Southern Middle Realty

    249 Lookout Dr, Winchester, TN 37398
    • /26

      Est $287,659

      Not Listed For Sale

      266 Water Tank Rd, Winchester, TN 37398

      • 3 Beds
      • 2 Baths
      • 1,447 Sq Ft
      • Built 1997
      266 Water Tank Rd, Winchester, TN 37398

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent David Janke Canopy Real Estate

  • /15

    $125,000

    $75K PRICE DROP
    • Land
    • 0 Sq Ft

    0 Slalom Cir Unit 104, Winchester, TN 37398

    RECENTLY REDUCED! Don’t miss this opportunity to own one of the few remaining water-view building lots in the highly sought-after Twin Creeks Village community. Located on prestigious Lot #104 Slalom Circle, this prime homesite sits on one of the most desirable streets in the development—an ideal setting to build your custom water-view dream home in a peaceful, upscale lakeside

    Felicia Wright Leading Edge Real Estate Group

    0 Slalom Cir Unit 104, Winchester, TN 37398
  • /39

    $250,000

    Sold Apr 02, 2026

    301 N Shephard St, Winchester, TN 37398

    • 2 Beds
    • 2 Baths
    • 1,313 Sq Ft
    • Built 1965

    Last Sold Summary

    • 4% Below List Price
    • $190/SF
    • 22 Days On Market

    Current Estimated Value $254,556

    Last Listing Agent Timothy Collins SimpliHOM

    301 N Shephard St, Winchester, TN 37398
    • /42

      Est $297,364

      Not Listed For Sale

      1053 Rowe Gap Rd, Winchester, TN 37398

      • 3 Beds
      • 2 Baths
      • 1,386 Sq Ft
      • Built 1995
      1053 Rowe Gap Rd, Winchester, TN 37398

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Melissa Stewart Swaffords Property Shop

  • /27

    $499,999

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,388 Sq Ft

    512 Cline Ridge Rd, Winchester, TN 37398

    Fresh opportunity on Tims Ford Lake with improved pricing! If you have been looking for privacy, land, and lake life, this one deserves a second look. Set on a wooded lot with space for backyard bonfires, quiet evenings under the stars, and outdoor living, this property also includes private dock access approximately 400 yards from the home. Be on the water in minutes with no long idle zones and

    Jordan Crouch Benchmark Realty, LLC

    512 Cline Ridge Rd, Winchester, TN 37398
  • /39

    $1,225,000

    Sold Sep 11, 2026

    90 Wildwood Ct, Winchester, TN 37398

    • 3 Beds
    • 2 Baths
    • 2,184 Sq Ft
    • Built 1999

    Last Sold Summary

    • 4% Below List Price
    • $561/SF
    • 18 Days On Market

    Current Estimated Value $1,254,882

    Last Listing Agent Marla Richardson Parks Compass

    90 Wildwood Ct, Winchester, TN 37398
    • /44

      Est $387,157

      Not Listed For Sale

      176 Susie Dr, Winchester, TN 37398

      • 3 Beds
      • 2 Baths
      • 1,961 Sq Ft
      • Built 1995
      176 Susie Dr, Winchester, TN 37398

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Pelatiah Prince Winton Auction & Realty Co.

  • /18

    $940,000

    • Land
    • 37.6 Acres
    • $25,000 per Acre

    0 Norwood Creek Rd, Winchester, TN 37398

    Beautiful acreage. Mountain views with a secluded feel. Creek runs through property. Ready for your dream house or mini farm. Owner has current survey. No perk site has been established so choose where you would want to build. All information deemed to be accurate please verify any important information.

    Benjamin Merrill Lynch Rigsby Realty & Auction, LLC

    0 Norwood Creek Rd, Winchester, TN 37398

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