9,964

Winchester, TN Homes

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  • /53

    $1,075,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,583 Sq Ft

    71 Fanning Bend Dr, Winchester, TN 37398

    Welcome to luxury lake living in the prestigious Fanning Bend Subdivision. Situated on a large, beautifully maintained lot, this exceptional home offers the perfect blend of comfort, entertaining space, and year-round lake lifestyle amenities. The property features both a 2-car attached garage and an impressive 31x25 detached 2-car garage (heated and cooled), providing ample space for boat

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 213-3698

    71 Fanning Bend Dr, Winchester, TN 37398
  • /5

    $70,000

    Sold Apr 24, 2026

    0 Garrett Ln Unit RTC3123002, Winchester, TN 37398

    • Land
    • 42,688 Sq Ft
    • $71,429 per Acre

    Last Sold Summary

    • 21% Below List Price
    • 68 Days On Market

    Last Listing Agent Thomas Ore Winton Auction & Realty Co.

    0 Garrett Ln Unit RTC3123002, Winchester, TN 37398
    • /32

      Est $263,708

      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

      • 29% Above List Price
      • $96/SF
      • 10 Days On Market
      • Last Sold Price $205,000
      • Jan 02, 2024

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

  • /10

    $129,000

    • Land
    • 1.1 Acres
    • $117,701 per Acre

    0 Aedc Rd Unit Tract3, Winchester, TN 37398

    Prime Commercial Opportunity – High-Traffic Location. Don’t miss this exceptional opportunity to own vacant commercial land in a highly visible, high-traffic area. Positioned for maximum exposure, this property offers endless potential for a wide range of business ventures. With continued growth in the surrounding area, this is your chance to secure a strategic location. Tracts 2 and 4 available

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 281-8047

    0 Aedc Rd Unit Tract3, Winchester, TN 37398
  • /22

    $185,000

    Sold May 08, 2026

    709 Isbell Turn Rd, Winchester, TN 37398

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Built 1945

    Last Sold Summary

    • 26% Below List Price
    • $178/SF
    • 112 Days On Market

    Current Estimated Value $207,041

    Last Listing Agent Adam Brock Canopy Real Estate

    709 Isbell Turn Rd, Winchester, TN 37398
    • /4

      Est $196,995

      Not Listed For Sale

      1770 Short Creek Rd, Winchester, TN 37398

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

      Last Sold Summary

      • 64% Above List Price
      • $55/SF
      • 364 Days On Market
      • Last Sold Price $120,000
      • Dec 20, 2023

      Last Listing Agent James Sutton SUTTON REALTY CO.

  • /3

    $79,900

    • Land
    • 14,374 Sq Ft
    • $242,121 per Acre

    0 Deer Valley Cir Unit RTC2980780, 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) 909-2266

    0 Deer Valley Cir Unit RTC2980780, Winchester, TN 37398
  • /29

    $165,000

    Sold Apr 10, 2026

    506 6th Ave NW, Winchester, TN 37398

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft
    • Built 1958

    Last Sold Summary

    • 6% Below List Price
    • $164/SF
    • 8 Days On Market

    Current Estimated Value $166,972

    Last Listing Agent Pelatiah Prince Winton Auction & Realty Co.

    506 6th Ave NW, Winchester, TN 37398
    • /41

      Est $373,891

      Not Listed For Sale

      6933 Winchester Hwy, Winchester, TN 37398

      • 5 Beds
      • 3 Baths
      • 2,632 Sq Ft
      • Built 1945
      6933 Winchester Hwy, Winchester, TN 37398

      Last Sold Summary

      • 4% Below List Price
      • $148/SF
      • 35 Days On Market
      • Last Sold Price $389,000
      • May 26, 2023

      Last Listing Agent Fallon Massey Van Massey Realty & Auction

  • /3

    $76,900

    • Land
    • 6,534 Sq Ft
    • $512,667 per Acre

    0 Deer Valley Cir Unit RTC2980774, 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) 869-7139

    0 Deer Valley Cir Unit RTC2980774, 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 $316,772

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

    209 Franklin Park, Winchester, TN 37398
    • /69

      Est $726,278

      Not Listed For Sale

      200 Greenleaf Ln, Winchester, TN 37398

      • 5 Beds
      • 3 Baths
      • 2,957 Sq Ft
      • Built 1987
      200 Greenleaf Ln, Winchester, TN 37398

      Last Sold Summary

      • 4% Above List Price
      • $237/SF
      • 111 Days On Market
      • Last Sold Price $700,000
      • Sep 27, 2023

      Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  • /3

    $69,900

    • Land
    • 6,534 Sq Ft
    • $466,000 per Acre

    0 Deer Valley Cir Unit RTC2980750, 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) 369-2282

    0 Deer Valley Cir Unit RTC2980750, 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
    • /48

      Est $574,632

      Not Listed For Sale

      124 Sugar Leaf Cir, Winchester, TN 37398

      • 5 Beds
      • 3.5 Baths
      • 3,776 Sq Ft
      • Built 1993
      124 Sugar Leaf Cir, Winchester, TN 37398

      Last Sold Summary

      • 28% Above List Price
      • $119/SF
      • 234 Days On Market
      • Last Sold Price $450,000
      • Mar 22, 2024

      Last Listing Agent Mike Stubblefield Franklin County Realty

  • /3

    $69,900

    • Land
    • 6,534 Sq Ft
    • $466,000 per Acre

    0 Deer Valley Cir Unit RTC2980752, 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) 593-5082

    0 Deer Valley Cir Unit RTC2980752, Winchester, TN 37398
  • /39

    $935,000

    Sold May 18, 2026

    995 Dripping Springs Rd, Winchester, TN 37398

    • 3 Beds
    • 2.5 Baths
    • 2,256 Sq Ft
    • Built 2007

    Last Sold Summary

    • 6% Below List Price
    • $414/SF
    • 160 Days On Market

    Current Estimated Value $937,278

    Last Listing Agent Anna Greer eXp Realty

    995 Dripping Springs Rd, Winchester, TN 37398
    • /22

      Est $231,877

      Not Listed For Sale

      211 N Jefferson St, Winchester, TN 37398

      • 3 Beds
      • 2 Baths
      • 1,956 Sq Ft
      • Built 1920
      211 N Jefferson St, Winchester, TN 37398

      Last Sold Summary

      • 3% Above List Price
      • $116/SF
      • 81 Days On Market
      • Last Sold Price $226,000
      • Apr 30, 2025

      Last Listing Agent Penny Patterson Swaffords Property Shop

  • /16

    Call for Price

    0 Highway 50, Winchester, TN 37398

    Absolute LIVE & ONSITE AUCTION Saturday June 13th 10:00 AM, 127± Acres in 4 Tracts• Selling with a New Certified SurveyAt the corner of HWY 50 at Galloway Lane | Winchester, TN - signs are posted! Ample Road Frontage, Large Acreage Tracts!offering breathtaking panoramic hillside views, usable pasture, wooded privacy, and real potential for recreation, homesites, or future development.

    Agent Photo

    James R. Cash

    James R. Cash II Auctions & Real Estate

    (931) 271-1719

    0 Highway 50, 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 $246,893

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

    408 Style St, Winchester, TN 37398
    • /30

      Est $287,339

      Not Listed For Sale

      759 Little Hurricane Rd, Winchester, TN 37398

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1979
      759 Little Hurricane Rd, Winchester, TN 37398

      Last Sold Summary

      • 15% Above List Price
      • $166/SF
      • 10 Days On Market
      • Last Sold Price $249,000
      • Mar 27, 2024

      Last Listing Agent Melissa Stewart Swaffords Property Shop

  • /34

    $699,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,754 Sq Ft

    74 Maple Dr, Winchester, TN 37398

    Welcome to this stunning, fully remodeled 3-bedroom, 2-bath brick ranch located in the desirable Dripping Springs subdivision. This exceptional property includes a deeded out lot on Tim’s Ford Lake, complete with a brand-new single-slip, low-maintenance boat dock—perfect for enjoying lake life to the fullest. This deeded lake lot is just a short 1 minute golf cart ride away! Interior features

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 485-6858

    74 Maple Dr, Winchester, TN 37398
  • /24

    $199,500

    Sold May 05, 2026

    815 N High St, Winchester, TN 37398

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft
    • Built 1943

    Last Sold Summary

    • $213/SF
    • 92 Days On Market

    Current Estimated Value $195,048

    Last Listing Agent Heather Boldizsar Lake Homes Realty, LLC

    815 N High St, Winchester, TN 37398
    • /22

      Est $369,887

      Not Listed For Sale

      146 Union Rd, Winchester, TN 37398

      • 3 Beds
      • 2 Baths
      • 1,432 Sq Ft
      • Built 1996
      146 Union Rd, Winchester, TN 37398

      Last Sold Summary

      • 12% Above List Price
      • $230/SF
      • 22 Days On Market
      • Last Sold Price $330,000
      • Jul 28, 2023

      Last Listing Agent Marsia Miller Middle Tennessee Realty Group, Inc.

  • /85

    $1,445,000

    $80K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 4,500 Sq Ft

    71 Slalom Cir, Winchester, TN 37398

    Luxury Lakefront Home in Gated Community – Over 4,500 Sq Ft of Elegant Living. Discover the epitome of upscale living in this stunning lakefront estate, nestled within a secure gated community. Meticulously designed space, this residence offers sweeping views of TVA grounds and the tranquil lake from Primary Bedroom and Office. **Key Features Include:** - **Spacious & Elegant Interiors:** 10 and

    Agent Photo

    Billie Kay Caldwell

    Swaffords Property Shop

    (931) 416-1049

    71 Slalom Cir, Winchester, TN 37398
  • /64

    $485,000

    Sold May 13, 2026

    148 Brandi Way, Winchester, TN 37398

    • 4 Beds
    • 3 Baths
    • 2,564 Sq Ft
    • Built 1990

    Last Sold Summary

    • 3% Below List Price
    • $189/SF
    • 41 Days On Market

    Current Estimated Value $496,872

    Last Listing Agent Elizabeth Padgett Century 21 Volunteer Realty

    148 Brandi Way, Winchester, TN 37398
    • /49

      Est $615,832

      Not Listed For Sale

      1026 Franklin Heights Dr, Winchester, TN 37398

      • 4 Beds
      • 2.5 Baths
      • 2,972 Sq Ft
      • Built 1996
      1026 Franklin Heights Dr, Winchester, TN 37398

      Last Sold Summary

      • 2% Below List Price
      • $212/SF
      • 71 Days On Market
      • Last Sold Price $630,000
      • Dec 17, 2024

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

  • /3

    $76,900

    • Land
    • 7,405 Sq Ft
    • $452,353 per Acre

    0 Deer Valley Cir Unit RTC2980777, 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) 499-2172

    0 Deer Valley Cir Unit RTC2980777, Winchester, TN 37398
  • /4

    $250,000

    Sold Oct 22, 2025

    0 Lynchburg Rd Unit RTC2927728, Winchester, TN 37398

    • Land
    • 10.11 Acres
    • $24,728 per Acre

    Last Sold Summary

    • 17% Below List Price
    • 83 Days On Market

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

    0 Lynchburg Rd Unit RTC2927728, Winchester, TN 37398
    • /29

      Est $309,295

      Not Listed For Sale

      129 Fairview Cir, Winchester, TN 37398

      • 3 Beds
      • 2.5 Baths
      • 1,694 Sq Ft
      • Built 2005
      129 Fairview Cir, Winchester, TN 37398

      Last Sold Summary

      • 19% Above List Price
      • $153/SF
      • 36 Days On Market
      • Last Sold Price $260,000
      • Jun 23, 2023

      Last Listing Agent John Peck Century 21 Volunteer Realty

  • /36

    $334,500

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,439 Sq Ft

    387 Fairview Cir, Winchester, TN 37398

    Welcome to this beautifully maintained all-brick home situated on a spacious corner lot of over half an acre! This charming one-level residence offers a desirable split-bedroom floor plan, providing both privacy and functionality for everyday living. Inside, you'll find a well-cared-for interior featuring comfortable living spaces, a practical layout, and plenty of natural light throughout. The

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 321-6797

    387 Fairview Cir, Winchester, TN 37398
  • /22

    $1,295,000

    Sold Aug 22, 2025

    732 Fanning Bend Dr, Winchester, TN 37398

    • 4 Beds
    • 3.5 Baths
    • 3,380 Sq Ft
    • Built 2025

    Last Sold Summary

    • $383/SF
    • 23 Days On Market

    Last Listing Agent Mikayla Wurth Southern Middle Realty

    732 Fanning Bend Dr, Winchester, TN 37398
    • /39

      Est $646,406

      Not Listed For Sale

      545 Pickney Rd, Winchester, TN 37398

      • 4 Beds
      • 3.5 Baths
      • 3,219 Sq Ft
      • Built 2008
      545 Pickney Rd, Winchester, TN 37398

      Last Sold Summary

      • 10% Above List Price
      • $182/SF
      • 193 Days On Market
      • Last Sold Price $585,000
      • Jun 20, 2024

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

  • /62

    $949,999

    $250K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,640 Sq Ft

    182 Loop Dr, Winchester, TN 37398

    5-Bedroom Lakefront Home with Dedicated Pier, TVA-Approved Dock, and Separate Living Spaces — A Perfect Retreat for Families and Entertainers** Welcome to your dream waterfront oasis! Nestled on a sprawling lot with breathtaking panoramic views of the tranquil lake, this exceptional property combines luxury, comfort, and versatility. Whether you're seeking a peaceful retreat, family haven, or an

    Agent Photo

    Billie Kay Caldwell

    Swaffords Property Shop

    (931) 465-2434

    182 Loop Dr, Winchester, TN 37398
  • /65

    $575,000

    Sold Mar 30, 2026

    250 Awalt Dr, Winchester, TN 37398

    • 4 Beds
    • 2 Baths
    • 3,068 Sq Ft
    • Built 1900

    Last Sold Summary

    • 6% Below List Price
    • $187/SF
    • 136 Days On Market

    Last Listing Agent Miciah Viel Keller Williams Realty Nashville/Franklin

    250 Awalt Dr, Winchester, TN 37398
    • /22

      Est $231,618

      Not Listed For Sale

      142 Cheyenne Ave, Winchester, TN 37398

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft
      • Built 1997
      142 Cheyenne Ave, Winchester, TN 37398

      Last Sold Summary

      • 10% Above List Price
      • $168/SF
      • 2 Days On Market
      • Last Sold Price $210,000
      • Jul 21, 2023

      Last Listing Agent Lauren Bailey Swaffords Property Shop

  • /2

    $199,900

    • 3 Beds
    • 2 Baths
    • 1,672 Sq Ft

    1011 Massengill St, Winchester, TN 37398

    Great started home or Investment property (currently rented.) Cute little 3 bedroom/2 bath home with bonus room that could even serve as a 4th bedroom. Located within walking distance of Tim's Ford Lake and just minutes from Downtown Winchester!

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 532-7547

    1011 Massengill St, Winchester, TN 37398
  • /34

    $214,900

    Sold Aug 22, 2025

    317 1st Ave SW, Winchester, TN 37398

    • 4 Beds
    • 2 Baths
    • 2,776 Sq Ft
    • Built 1900

    Last Sold Summary

    • 14% Below List Price
    • $77/SF
    • 53 Days On Market

    Current Estimated Value $269,100

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

    317 1st Ave SW, Winchester, TN 37398
    • /41

      Est $435,325

      Not Listed For Sale

      218 Charlotte Dr, Winchester, TN 37398

      • 3 Beds
      • 3 Baths
      • 2,116 Sq Ft
      • Built 2005
      218 Charlotte Dr, Winchester, TN 37398

      Last Sold Summary

      • $206/SF
      • 12 Days On Market
      • Last Sold Price $435,000
      • Jul 03, 2023

      Last Listing Agent Jeromey Cromwell RE/MAX

  • /40

    $695,900

    • 4 Beds
    • 3.5 Baths
    • 2,560 Sq Ft

    59 Turtle Ct, Winchester, TN 37398

    Lake Life at its FINEST- this remarkable home in Twin Creeks Subdivision has everything you need! Open Living concept for easy entertaining featuring vaulted ceilings, 5 burner Gas cooktop, double ovens, Quartz countertops and designer lighting. Primary suite is on the main level. Upstairs features 3 large bedrooms all with walk in closets as well as built in bunks perfect for sleepovers! Large

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 283-6057

    59 Turtle Ct, Winchester, TN 37398

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