Homes in ZIP Code 37398

• 

  

  

  /3

  $76,900

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

  0 Deer Valley Cir Unit RTC2980812, 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-

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  (931) 535-5725

  0 Deer Valley Cir Unit RTC2980812, Winchester, TN 37398
• 

  

  

  /19

  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 2,235 Sq Ft
  • House for Rent

  427 Favre Cir, Winchester, TN 37398

  Gorgeous Custom-made home features one floor-designed layout with a large fireplace in the living room, open kitchen-dining, carpet in all bedrooms, a large vaulted greatroom, and a nice covered porch with a ceiling fan and a large backyard is perfect for entertainment. Grand master suite with oversized bath to relax your day~ Pets are accepted on a case-by-case basis with a non-refundable $350

  Momoko Imai Berkshire Hathaway HomeServices Woodmont Realty

  427 Favre Cir, Winchester, TN 37398
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  /17

  $189,471 Sold Nov 05, 2025

  0 Aedc Rd Unit RTC3007773, Winchester, TN 37398

  • Land
  • 3.38 Acres
  • $56,057 per Acre

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Vandy VanMeter Parks Auction & Realty

  0 Aedc Rd Unit RTC3007773, Winchester, TN 37398
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  /29

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,495 Sq Ft

  811 S Shephard St, Winchester, TN 37398

  811 S Shephard St, Winchester, TN 37398
• 

  

  

  /22

  $389,900

  • 4 Beds
  • 2.5 Baths
  • 1,899 Sq Ft

  2321 Old Tullahoma Rd, Winchester, TN 37398

  Welcome to 2321 Old Tullahoma Rd in Winchester, TN—a well-located 4-bedroom, 2.5-bath home offering space, convenience, and flexibility. Situated less than 1/4 of a mile from Tims Ford Lake and just minutes from the Winchester Square, this property provides easy access to recreation, shopping, and dining. The home features a large basement currently used for storage and an at-home gym, offering

  

  John Peck

  Peck Realty Group, LLC

  (931) 465-3726

  2321 Old Tullahoma Rd, Winchester, TN 37398
• 

  

  /8

  $950 per month

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft
  • House for Rent

  2965 Old Tullahoma Rd, Winchester, TN 37398

  Charming small home right on Old Tullahoma Rd. The house has a beautiful .25 miles gravel driveway surrounded by tall trees. Only 5 minutes from Winchester City Park and 7 minutes from Winchester Square. This home would be perfect for any individual or small family. No smoking. No pets. Comes with a washer-dryer combo.

  Jordan Beasley 1st Choice REALTOR

  2965 Old Tullahoma Rd, Winchester, TN 37398
• 

  

  /33

  $340,000 Sold Sep 06, 2025

  401 E Petty Ln, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 3,960 Sq Ft
  • Built 1960

  Last Sold Summary

  • 19% Below List Price
  • $86/SF
  • 145 Days On Market

  Current Estimated Value $328,749

  Last Listing Agent Jerry Shelton Shelton Auction and Realty

  401 E Petty Ln, Winchester, TN 37398
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  /6

  Not Listed For Sale

  0 Cypress Point Dr Unit RTC2708474, Winchester, TN 37398

  0 Cypress Point Dr Unit RTC2708474, Winchester, TN 37398
• 

  

  /6

  $129,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,145 Sq Ft

  209 N Jefferson St, Winchester, TN 37398

  This versatile 2-bedroom, 1-bathroom home offers a prime investment opportunity with endless potential. Featuring a spacious garage, this property can serve as a comfortable residence or be transformed into a functional office space. With a flexible layout and a blank slate for customization, it’s the perfect canvas to bring your vision to life.

  

  John Peck

  Peck Realty Group, LLC

  (931) 404-0461

  209 N Jefferson St, Winchester, TN 37398
• 

  

  /10

  $900 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  110 Allen Dr Unit A, Winchester, TN 37398

  All brick, hardwood floors, close to Kroger, washer/dryer hookups, very clean, large backyard.

  Curtis Benchmark Realty, LLC

  110 Allen Dr Unit A, 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
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  /42

  Est $537,487 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,940 Sq Ft

  115 Barefoot Way, Winchester, TN 37398

  115 Barefoot Way, Winchester, TN 37398
• 

  

  /3

  $79,900

  • Land
  • 0.39 Acre
  • $204,872 per Acre

  0 Deer Valley Cir Unit RTC2980801, 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-

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  (931) 369-2070

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

  

  /40

  $3,600 per month

  • 5 Beds
  • 4 Baths
  • 3,800 Sq Ft
  • House for Rent

  4 Whippoorwill Cove Rd, Winchester, TN 37398

  Stunning New Construction on Tims Ford Lake with Private Dock Discover lakeside luxury in this beautiful new construction home tucked away in a serene, secluded cove on Tims Ford Lake. Thoughtfully designed and finished with exquisite attention to detail, this four-bedroom residence also features a dedicated office with a closet that can serve as a fifth bedroom. Inside, you’ll find designer

  Phillip Poynor simpliHOM

  4 Whippoorwill Cove Rd, 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 $105,623

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

  512 Elm St, Winchester, TN 37398
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  /10

  Not Listed For Sale

  0 Lookout Dr Unit RTC2650177, Winchester, TN 37398

  0 Lookout Dr Unit RTC2650177, Winchester, TN 37398
• 

  

  /3

  $76,900

  • Land
  • 0.16 Acre
  • $480,625 per Acre

  0 Deer Valley Cir Unit RTC2980734, 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-

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  (931) 213-6916

  0 Deer Valley Cir Unit RTC2980734, Winchester, TN 37398
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  /43

  $2,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,896 Sq Ft
  • House for Rent

  396 Harris Chapel Dr, Winchester, TN 37398

  Sharon Swafford Swaffords Property Shop

  396 Harris Chapel Dr, Winchester, TN 37398
• 

  

  /40

  $275,000 Sold Mar 31, 2025

  551 Fairview Cir, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,545 Sq Ft
  • Built 2004

  Last Sold Summary

  • 5% Below List Price
  • $178/SF
  • 33 Days On Market

  Current Estimated Value $293,530

  Last Listing Agent John Peck Peck Realty Group, LLC

  551 Fairview Cir, Winchester, TN 37398
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  /35

  Est $464,334 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,417 Sq Ft

  242 Pine Bluff Rd, Winchester, TN 37398

  242 Pine Bluff Rd, Winchester, TN 37398
• 

  

  /75

  $466,500 Pending

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

  105 Island Way, Winchester, TN 37398

  BEST DEAL IN TWIN CREEKS..... PRICE ADJUSTED TO MOVE.... COMES FURNISHED... Welcome to 105 Island Way – a 3 BR / 2.5 bath townhouse in the highly desirable Twin Creeks gated community! This well located property comes fully furnished, having previously been used by the owners as a vacation home (NOT a short-term rental!) With the layout of the community, the attached screen porch (with firepit)

  

  Billie Kay Caldwell

  Swaffords Property Shop

  (931) 535-5282

  105 Island Way, 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 $142,955

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

  411 Style St, Winchester, TN 37398
• 

  

  /10

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  0 Crestview Dr, Winchester, TN 37398

  0 Crestview Dr, Winchester, TN 37398
• 

  

  /3

  $76,900

  • Land
  • 0.16 Acre
  • $480,625 per Acre

  0 Deer Valley Cir Unit RTC2980739, 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-

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  (931) 348-1796

  0 Deer Valley Cir Unit RTC2980739, Winchester, TN 37398
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  /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 $1,250,387

  Last Listing Agent Sam Hatfield Sam Hatfield Realty, Inc.

  668 Bluff Dr, Winchester, TN 37398
• 

  

  /22

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,581 Sq Ft

  224 Dry Creek Ln, Winchester, TN 37398

  224 Dry Creek Ln, Winchester, TN 37398
• 

  

  /3

  $74,900

  • Land
  • 0.23 Acre
  • $325,652 per Acre

  0 Deer Valley Cir Unit RTC2980741, 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-

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  (931) 281-7603

  0 Deer Valley Cir Unit RTC2980741, 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 $359,636

  Last Listing Agent John Peck Peck Realty Group, LLC

  147 Crimson Dr, Winchester, TN 37398
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  /48

  Est $1,949,201 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 5,185 Sq Ft

  260 Shasteen Bend Dr, Winchester, TN 37398

  260 Shasteen Bend Dr, Winchester, TN 37398
• 

  

  /3

  $69,900

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

  0 Deer Valley Cir Unit RTC2980748, 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-

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  (931) 914-3785

  0 Deer Valley Cir Unit RTC2980748, Winchester, TN 37398
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  /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
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  /34

  Est $546,752 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,350 Sq Ft

  267 Bryan Dr, Winchester, TN 37398

  267 Bryan Dr, Winchester, TN 37398
• 

  

  /3

  $69,900

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

  0 Deer Valley Cir Unit RTC2980782, 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-

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  (931) 904-3514

  0 Deer Valley Cir Unit RTC2980782, 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
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  /8

  Not Listed For Sale

  0 Charles Ave, Winchester, TN 37398

  0 Charles Ave, Winchester, TN 37398
• 

  

  /27

  $259,900

  • 3 Beds
  • 2 Baths
  • 1,353 Sq Ft

  1102 N High St, Winchester, TN 37398

  Charming all-brick 3-bedroom, 2 bath home just minutes from the heart of downtown Winchester and a short jog to the boat ramp at the bass club on Tims Ford Lake. Enjoy beautiful lake views from the front yard and beautiful hardwood floors throughout much of the home. The spacious kitchen offers ample cabinet and counter space, perfect for everyday living and entertaining. An attached carport with

  

  Chelsea Greenway

  Winton Auction & Realty Co.

  (931) 288-5154

  1102 N High St, 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 $252,145

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

  408 Style St, Winchester, TN 37398
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  /29

  Est $417,804 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,891 Sq Ft

  23 Anderton Dr, Winchester, TN 37398

  23 Anderton Dr, Winchester, TN 37398
• 

  

  /3

  $69,900

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

  0 Deer Valley Cir Unit RTC2980758, 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-

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  (931) 616-5552

  0 Deer Valley Cir Unit RTC2980758, Winchester, TN 37398
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  /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

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