Winchester, TN Homes

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  /39

  $260,000 Under Contract

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

  301 N Shephard St, Winchester, TN 37398

  This two-bedroom charmer is only two minutes to Twin Creeks Marina, Boat ramps, Winchester Park, and the Winchester Town Square! Features an inviting and relaxing back yard! Covered patio with ceiling fan! Two large sheds, one equipped with power for endless potential! Many structural and plumbing updates recently!

  

  Timothy Collins

  SimpliHOM

  (931) 377-2832

  301 N Shephard St, Winchester, TN 37398
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  /36

  $1,650 per month

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • House for Rent

  71 Apple Dr, Winchester, TN 37398

  Now taking applications. Well maintained 3br/2bath home featuring hardwood floors, over-sized one car garage, vaulted living room, spacious eat-in kitchen, concrete drive, and nice size patio for entertaining. Utilities and lawn mowing are the tenant's responsibility. Security and background check required. 600 minimum credit score required.

  Sharon Swafford Swaffords Property Shop

  71 Apple Dr, Winchester, TN 37398
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  /20

  $192,000 Sold Apr 30, 2025

  334 Church Ln, Winchester, TN 37398

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 2016

  Last Sold Summary

  • 4% Above List Price
  • $148/SF
  • 9 Days On Market

  Last Listing Agent Ashley Hill Southern Middle Realty

  334 Church Ln, Winchester, TN 37398
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  /32

  Est $197,629 Not Listed For Sale

  408 6th Ave NW, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1950

  408 6th Ave NW, Winchester, TN 37398

  Last Sold Summary

  • 1% Above List Price
  • $169/SF
  • 337 Days On Market

  Last Sold Price $195,000

  Last Listing Agent Yvonne Stewart Winton Auction & Realty Co.
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  /26

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  1587 By Pass Rd, Winchester, TN 37398

  Beautiful 3 Bedroom, 2 bath, brick home located minutes from beautiful downtown Winchester, featuring quaint shops and a wide variety of restaurants to choose from. Also minutes Tims Ford Lake, Wood Reservoir & Nissan.Attached garage and detached garage/workshop.

  

  Patricia Boswell

  Hanson Realty & Auction Company

  (931) 369-3291

  1587 By Pass Rd, Winchester, TN 37398
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  /29

  $1,900 per month

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • House for Rent

  808 N High St, Winchester, TN 37398

  Fully Furnished! This charming vintage property features 2 bedrooms, 2 bathrooms. It has a large partially fenced backyard with an outdoor patio area. The location is great, situated between Tims Winchester City Park on Tims Ford Lake and downtown Winchester Square. The house is solidly built from tongue-and-groove oak throughout, with beautiful crown-style molding, and updated windows in almost

  Sharon Swafford Swaffords Property Shop

  808 N High St, Winchester, TN 37398
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  /2

  $109,055 Sold Aug 19, 2025

  0 Haddon Ln Unit RTC2891649, Winchester, TN 37398

  • Land
  • 7.14 Acres
  • $15,274 per Acre

  Last Sold Summary

  • 36% Below List Price
  • 48 Days On Market

  Last Listing Agent Teresa Miller Century 21 Coffee County Realty & Auction

  0 Haddon Ln Unit RTC2891649, Winchester, TN 37398
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  /56

  Est $430,696 Not Listed For Sale

  318 Shadowbrook Rd, Winchester, TN 37398

  • 5 Beds
  • 3.5 Baths
  • 3,492 Sq Ft
  • Built 1968

  318 Shadowbrook Rd, Winchester, TN 37398

  Last Sold Summary

  • 6% Above List Price
  • $116/SF
  • 54 Days On Market

  Last Sold Price $405,000

  Last Listing Agent Billie Kay Caldwell Swaffords Property Shop
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  /80

  $599,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,751 Sq Ft

  214 River Watch Way, Winchester, TN 37398

  This beautiful, well-designed home in the gated Twin Creeks Village on Tim’s Ford Lake offers a spacious, functional floor plan with great separation for guests or family. Step inside to beautiful real hardwood floors, soaring ceilings, and a dramatic catwalk that gives the home a distinctive, open feel. The gourmet kitchen features granite countertops, a gas range, built-in oven, soft-close

  

  Becca Gilbert

  SimpliHOM

  (931) 560-8055

  214 River Watch Way, Winchester, TN 37398
• 

  

  /22

  $3,900 per month

  • 5 Beds
  • 4 Baths
  • 2,753 Sq Ft
  • House for Rent

  622 River Watch Way, Winchester, TN 37398

  Furnished rental in Twin Creeks Subdivision beside Tim’s Ford lake! This home features 5 bedrooms 4 baths designed by an interior decorator. Three pools and a clubhouse in a golf cart community. Just minutes from downtown Winchester shopping and restaurants.

  Susan Bryant Keller Williams Realty Nashville/Franklin

  622 River Watch Way, Winchester, TN 37398
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  /25

  $364,000 Sold Feb 20, 2026

  6421 Lynchburg Rd, Winchester, TN 37398

  • 2 Beds
  • 2 Baths
  • 1,540 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $236/SF
  • 17 Days On Market

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

  6421 Lynchburg Rd, Winchester, TN 37398
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  /27

  Not Listed For Sale

  0 Kayak Way Unit RTC2781841, Winchester, TN 37398

  0 Kayak Way Unit RTC2781841, Winchester, TN 37398

  Last Sold Summary

  • 37 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Shelia Lunsford Benchmark Realty, LLC
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  /51

  $774,000

  • 4 Beds
  • 3.5 Baths
  • 3,017 Sq Ft

  71 Windjammer Ct, Winchester, TN 37398

  Lake Season is just around the corner and 71 Windjammer has you covered! Welcome to your dream home in Twin Creeks Village, where comfort meets style and convenience. This beautiful 4-bedroom, 3.5-bath home offers spacious living with a thoughtful layout and high-end touches throughout. Downstairs you will find a seamless flow between the living room and kitchen, perfect for entertaining or

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  (931) 740-1561

  71 Windjammer Ct, Winchester, TN 37398
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  /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
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  /13

  $229,500 Sold Feb 20, 2026

  157 Modena Cir, Decherd, TN 37324

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Above List Price
  • $174/SF
  • 88 Days On Market

  Current Estimated Value $227,077

  Last Listing Agent Benjamin Merrill Lynch Rigsby Realty & Auction, LLC

  157 Modena Cir, Decherd, TN 37324
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  /3

  Not Listed For Sale

  0 Old Tullahoma Rd Unit RTC2775156, Winchester, TN 37398

  0 Old Tullahoma Rd Unit RTC2775156, Winchester, TN 37398

  Last Sold Summary

  • 8 Days On Market

  Last Sold Price $77,000

  Last Listing Agent Tony Griffis Better Homes & Gardens Real Estate Heritage Group
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  /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
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  /10

  $895 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
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  /43

  $510,000 Sold Apr 24, 2025

  80 Huntington Dr N, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1996

  Last Sold Summary

  • 4% Below List Price
  • $291/SF
  • 94 Days On Market

  Current Estimated Value $510,930

  Last Listing Agent Alexandra Watts Southern Middle Realty

  80 Huntington Dr N, Winchester, TN 37398
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  /50

  Not Listed For Sale

  918 S Jefferson St, Winchester, AL 35798

  • 3 Beds
  • 2.5 Baths
  • 2,401 Sq Ft
  • Built 2024

  918 S Jefferson St, Winchester, AL 35798

  Last Sold Summary

  • $235/SF
  • 59 Days On Market

  Last Sold Price $565,000

  Last Listing Agent Danny Duffey Duffeys Real Estate LLC
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  /68

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  620 Maple Bend Rd, Winchester, TN 37398

  Dreaming of living close to the lake? Looking to invest in an Airbnb near Tims Ford Lake? This completely remodeled 3 bedroom 2 bathroom house on nearly an acre lot is calling your name. Interior features include LVP flooring in main living areas, carpet in the bedrooms, stainless steel appliances, and more. Exterior features include covered porches, fresh landscaping, circular driveway, barn

  

  Amanda Seibers

  Woodruff Realty & Auction

  (931) 283-2399

  620 Maple Bend Rd, Winchester, TN 37398
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  /37

  $352,000 Sold Dec 22, 2025

  1203 Liberty Rd, Winchester, TN 37398

  • 2 Beds
  • 2.5 Baths
  • 1,709 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $206/SF
  • 103 Days On Market

  Last Listing Agent Christopher (Bra Heath Simmons Realty

  1203 Liberty Rd, Winchester, TN 37398
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  /83

  Not Listed For Sale

  918 S Jefferson St, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,401 Sq Ft
  • Built 2024

  918 S Jefferson St, Winchester, TN 37398

  Last Sold Summary

  • $235/SF
  • 84 Days On Market

  Last Sold Price $565,000

  Last Listing Agent Danny Duffey Duffeys Real Estate
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  /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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  /33

  $344,000 Sold Oct 30, 2025

  906 N High St, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,976 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Below List Price
  • $174/SF
  • 66 Days On Market

  Current Estimated Value $298,164

  Last Listing Agent Patsy Truslow Sewanee Realty

  906 N High St, Winchester, TN 37398
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  /49

  Est $593,724 Not Listed For Sale

  794 River Watch Way, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft
  • Built 2022

  794 River Watch Way, Winchester, TN 37398

  Last Sold Summary

  • 1% Above List Price
  • $308/SF
  • 0 Days On Market

  Last Sold Price $587,500

  Last Listing Agent Susan Baker BHGRE Baker & Cole
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  /12

  $85,000

  • Land
  • 0 Acre

  0 Dry Fork Dr Unit 76, Winchester, TN 37398

  Great opportunity to build your dream home with breath taking lake views in the exclusive Gated Resort Community of Twin Creeks Village. Preliminary House Plans are attached. Twin Creeks is the premiere lake living on the beautiful Tims Ford Lake. Community offers boat storage, marina w/ store and restaurant, 3 pool, pavilion with fireplace, underground utilities, city water and public sewer

  

  Dena Abbott

  SimpliHOM

  (931) 616-5407

  0 Dry Fork Dr Unit 76, Winchester, TN 37398
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  /27

  $130,000 Sold Jul 08, 2025

  708 Hooper Rd, Winchester, TN 37398

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 2021

  Last Sold Summary

  • 4% Below List Price
  • $118/SF
  • 32 Days On Market

  Last Listing Agent Amber Smith Century 21 Coffee County Realty & Auction

  708 Hooper Rd, Winchester, TN 37398
• 

  

  /22

  Not Listed For Sale

  35 Pittenger Cir, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 2024

  35 Pittenger Cir, Winchester, TN 37398

  Last Sold Summary

  • $208/SF
  • 117 Days On Market

  Last Sold Price $209,900

  Last Listing Agent Daryl Welch Freedom Realty Group
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  /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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  /29

  $199,000 Sold May 14, 2025

  125 8th Ave NW, Winchester, TN 37398

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1953

  Last Sold Summary

  • 3% Below List Price
  • $213/SF
  • 51 Days On Market

  Current Estimated Value $189,798

  Last Listing Agent Stephanie Dowdy Freedom Realty Group

  125 8th Ave NW, Winchester, TN 37398
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  /12

  Est $231,180 Not Listed For Sale

  100 Modena Cir, Decherd, TN 37324

  • 3 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • Built 2007

  100 Modena Cir, Decherd, TN 37324

  Last Sold Summary

  • 4% Above List Price
  • $174/SF
  • 42 Days On Market

  Last Sold Price $222,000

  Last Listing Agent Kelly Taylor Century 21 Coffee County Realty & Auction
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  /27

  $244,000

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

  1102 N High St, Winchester, TN 37398

  Motivated seller! 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

  

  Chelsea Greenway

  Winton Auction & Realty Co.

  (931) 288-5154

  1102 N High St, Winchester, TN 37398
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  /45

  $357,500 Sold Jul 16, 2025

  3965 Aedc Rd, Winchester, TN 37398

  • 5 Beds
  • 4 Baths
  • 3,741 Sq Ft
  • Built 1978

  Last Sold Summary

  • $96/SF
  • 22 Days On Market

  Current Estimated Value $380,201

  Last Listing Agent Darrell Huffman Keller Williams Realty - Murfreesboro

  3965 Aedc Rd, Winchester, TN 37398
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  /9

  Not Listed For Sale

  786 Rowe Gap Rd, Winchester, TN 37398

  • Built 1933

  786 Rowe Gap Rd, Winchester, TN 37398

  Last Sold Summary

  • 121% Above List Price
  • $83/SF
  • 6 Days On Market

  Last Sold Price $77,500

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.
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  /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
• 

  

  /3

  $79,900 Sold Sep 16, 2025

  0 Deer Valley Cir Unit RTC2980795, Winchester, TN 37398

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

  Last Sold Summary

  • 0 Days On Market

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

  0 Deer Valley Cir Unit RTC2980795, Winchester, TN 37398
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  /46

  Est $598,915 Not Listed For Sale

  181 Why Worry Ln, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,598 Sq Ft
  • Built 2021

  181 Why Worry Ln, Winchester, TN 37398

  Last Sold Summary

  • 2% Above List Price
  • $227/SF
  • 3 Days On Market

  Last Sold Price $590,000

  Last Listing Agent Lise Deschenes Fridrich & Clark Realty
• 

  

  /3

  $76,900

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

  0 Deer Valley Cir Unit RTC2980768, 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) 303-0477

  0 Deer Valley Cir Unit RTC2980768, 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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