Winchester, TN Homes

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  /26

  Est $104,880 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 849 Sq Ft

  515 Plattenburg St, Winchester, TN 37398

  515 Plattenburg St, Winchester, TN 37398
• 

  

  

  /15

  $140,000

  • Land
  • 0 Acre

  0 Slalom Cir Unit RTC2618426, 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 RTC2618426, Winchester, TN 37398
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  /8

  $224,990 Sold Sep 17, 2025

  0 Kayak Way Unit RTC2924412, Winchester, TN 37398

  • Land
  • 0 Acre

  Last Sold Summary

  • 6% Below List Price
  • 67 Days On Market

  Last Listing Agent Jon Sexton Benchmark Realty, LLC

  0 Kayak Way Unit RTC2924412, Winchester, TN 37398
• 

  

  

  /16

  Est $215,925 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,425 Sq Ft

  96 Duncan Ln, Winchester, TN 37398

  96 Duncan Ln, Winchester, TN 37398
• 

  

  

  /3

  $35,000

  • Land
  • 0.53 Acre
  • $66,038 per Acre

  0 Lees Ford Ln, Winchester, TN 37398

  .053-acre vacant lot offering excellent potential for a small residential build. Located outside city limits, this property provides the advantage of no city taxes while still conveniently accessible to nearby amenities. This parcel is zoned R-2 and is approved for a one-bedroom septic system. Property restrictions prohibit mobile homes. Whether you're looking to build your first home, downsize,

  Thomas Ore Winton Auction & Realty Co.

  0 Lees Ford Ln, Winchester, TN 37398
• 

  

  /41

  $285,000 Sold Aug 11, 2025

  419 Strawberry Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft
  • Built 2011

  Last Sold Summary

  • 5% Below List Price
  • $195/SF
  • 54 Days On Market

  Current Estimated Value $290,916

  Last Listing Agent Brandy Lee Gambill Georgia Evans Realty, LLC

  419 Strawberry Dr, Winchester, TN 37398
• 

  

  /9

  Est $188,815 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 985 Sq Ft

  310 3rd Ave SE, Winchester, TN 37398

  310 3rd Ave SE, Winchester, TN 37398
• 

  

  /52

  $1,550,000 New Construction

  • 4 Beds
  • 5 Baths
  • 4,089 Sq Ft

  FB 175 Plan at Fanning Bend, Winchester, TN 37398

  Experience the epitome of lakeside living in this magnificent 4-bedroom, 5-bathroom retreat nestled in the prestigious Fanning Bend community, crafted w excellence by Legacy South. Boasting panoramic views of the sparkling waters & surrounded by nature's tranquility, this home offers an unparalleled blend of luxury & serenity. Step inside to discover an open & airy floor plan, accentuated by

  Legacy South Builder

  947 Fanning Bend Dr Unit 36901184, Winchester, TN 37398
• 

  

  /16

  $180,000 Sold Oct 01, 2025

  810 Lynwood St, Winchester, TN 37398

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1948

  Last Sold Summary

  • 3% Below List Price
  • $161/SF
  • 22 Days On Market

  Current Estimated Value $180,594

  Last Listing Agent Shawna Denby 1st Choice REALTOR

  810 Lynwood St, Winchester, TN 37398
• 

  

  /19

  Est $149,693 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,379 Sq Ft

  414 4th Ave SE, Winchester, TN 37398

  414 4th Ave SE, Winchester, TN 37398
• 

  

  /25

  $259,900

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft

  286 Strawberry Dr, Winchester, TN 37398

  Fresh paint throughout, a soft-washed exterior, and newly cleared landscaping give this home a clean, welcoming feel from the moment you arrive. Inside, the HVAC has been serviced, vents professionally cleaned, and the home well maintained so you can settle in with confidence from day one. Located just minutes from downtown Winchester and the natural beauty of Tims Ford Lake, this home offers

  Rachel Ferrell Southern Middle Realty

  286 Strawberry Dr, Winchester, TN 37398
• 

  

  /66

  $600,000 Sold Jan 16, 2026

  105 Edgewater Dr, Winchester, TN 37398

  • 3 Beds
  • 3.5 Baths
  • 1,824 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $329/SF
  • 17 Days On Market

  Last Listing Agent Justin Johnson Go Realty, LLC

  105 Edgewater Dr, Winchester, TN 37398
• 

  

  /6

  Est $222,820 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,160 Sq Ft

  406 4th Ave SE, Winchester, TN 37398

  406 4th Ave SE, Winchester, TN 37398
• 

  

  /94

  $595,000

  • 3 Beds
  • 3.5 Baths
  • 2,579 Sq Ft

  319 Campfire Ct, Winchester, TN 37398

  Welcome to a truly special home in Twin Creeks Village, where lake living meets elevated design and everyday comfort. This beautifully appointed 3-bedroom, 3-full & 1-half bath home offers just under 2,600 square feet of thoughtfully designed space, featuring soaring ceilings and a dramatic two-story foyer layered with exquisite trim, statement light fixtures, and designer wallpaper details

  Meredith Smith Benchmark Realty, LLC

  319 Campfire Ct, Winchester, TN 37398
• 

  

  /58

  $969,999 Sold Jul 15, 2025

  45 Hickory Point Dr, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,582 Sq Ft
  • Built 2022

  Last Sold Summary

  • 3% Below List Price
  • $376/SF
  • 49 Days On Market

  Current Estimated Value $925,876

  Last Listing Agent Derrick Foster Keller Williams Realty Nashville/Franklin

  45 Hickory Point Dr, Winchester, TN 37398
• 

  

  /69

  Est $293,412 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,662 Sq Ft

  408 N Jefferson St, Winchester, TN 37398

  408 N Jefferson St, Winchester, TN 37398
• 

  

  /41

  $429,900

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft

  160 Anderton Dr, Winchester, TN 37398

  Welcome to 160 Anderton Dr – a spacious and beautifully maintained 4-bedroom, 2-bath highly desirable corner unit in a golf cart and lake community! This home features all hardwood floors downstairs, plantation shutters throughout, and a gas fireplace for cozy evenings. The kitchen is equipped with a gas stove, and all appliances remain for your convenience. The primary suite offers a zero-entry

  Brittany Friedmann Benchmark Realty, LLC

  160 Anderton Dr, Winchester, TN 37398
• 

  

  /59

  $1,600,000 Sold Aug 26, 2025

  947 Fanning Bend Dr, Winchester, TN 37398

  • 6 Beds
  • 5 Baths
  • 4,352 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $368/SF
  • 117 Days On Market

  Legacy South Fanning Bend

  947 Fanning Bend Dr, Winchester, TN 37398
• 

  

  /14

  Est $188,720 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,110 Sq Ft

  307 N College St, Winchester, TN 37398

  307 N College St, Winchester, TN 37398
• 

  

  /63

  $559,900 New Construction

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

  249 Lookout Dr, Winchester, TN 37398

  Builder offering up to $10,000 toward buyer incentives!MOTIVATED BUILDER – READY TO MOVE ON! BRING ALL OFFERS! Welcome to 249 Lookout Drive in Winchester, TN — a stunning new construction home that blends modern comfort, quality craftsmanship, and timeless style. This 3-bedroom, 2.5-bath residence offers a bright, open-concept layout designed for both everyday living and effortless

  Charlie Gonzales Southern Middle Realty

  249 Lookout Dr, Winchester, TN 37398
• 

  

  /46

  $590,000 Sold Mar 12, 2025

  181 Why Worry Ln, Winchester, TN 37398

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

  Last Sold Summary

  • 1% Below List Price
  • $227/SF
  • 3 Days On Market

  Current Estimated Value $596,824

  Last Listing Agent Lise Deschenes Fridrich & Clark Realty

  181 Why Worry Ln, Winchester, TN 37398
• 

  

  /15

  Est $203,417 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,783 Sq Ft

  208 3rd Ave NW, Winchester, TN 37398

  208 3rd Ave NW, Winchester, TN 37398
• 

  

  /26

  $64,000

  • Land
  • 0.91 Acre
  • $70,330 per Acre

  0 Cooper Ln, Winchester, TN 37398

  New Price! Reduced! Beautiful! Just under an acre residential lot is partially cleared and partially wooded. 5 Minutes to Winchester City Park & Public Boat Ramp, 8 Minutes to Winchester Courthouse Square' shopping, theater, restaurants and more. Must See!

  Sharon Swafford Swaffords Property Shop

  0 Cooper Ln, Winchester, TN 37398
• 

  

  /35

  $408,000 Sold Apr 08, 2025

  8433 Lynchburg Rd, Winchester, TN 37398

  • 4 Beds
  • 2 Baths
  • 2,110 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $193/SF
  • 102 Days On Market

  Last Listing Agent Andrew Curl Better Homes & Gardens Real Estate Heritage Group

  8433 Lynchburg Rd, Winchester, TN 37398
• 

  

  /69

  Est $542,144 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,380 Sq Ft

  227 Sells St, Winchester, TN 37398

  227 Sells St, Winchester, TN 37398
• 

  

  /8

  $169,000

  • 2 Beds
  • 1 Bath
  • 885 Sq Ft

  101 Highland St, Winchester, TN 37398

  Charming cottage in the heart of Winchester offering incredible potential and a hard-to-find, large privacy-fenced backyard. This 2-bedroom, 1-bath home features a durable metal roof, newer replacement windows, a new shed, and a recently added driveway. The attic provides impressive space with exciting possibilities for future expansion or storage. While the home needs a little TLC, it’s a

  Fhonda Hatmaker eXp Realty

  101 Highland St, Winchester, TN 37398
• 

  

  /3

  $40,000 Sold Jun 20, 2025

  0 Old Tullahoma Rd Unit RTC2775155, Winchester, TN 37398

  • Land
  • 3.19 Acres
  • $12,539 per Acre

  Last Sold Summary

  • 60% Below List Price
  • 142 Days On Market

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

  0 Old Tullahoma Rd Unit RTC2775155, Winchester, TN 37398
• 

  

  /3

  Est $168,899 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 928 Sq Ft

  807 Hunt St, Winchester, TN 37398

  807 Hunt St, Winchester, TN 37398
• 

  

  /70

  $3,800,000

  • 6 Beds
  • 8 Baths
  • 8,002 Sq Ft

  1657 Boswell Rd, Winchester, TN 37398

  HIGHEST GROSSING RENTAL ON TIM'S FORD LAKE!!! Welcome to your stunning dream retreat on 14 acres on a private cove of Tims Ford Lake. This magnificent turnkey 8,000+ sqft estate comes furnished and boasts a 5 bed, 5.5 bath with luxurious accommodations and ample space for 20+ guests. The home features a modern commercial grade kitchen, endless windows for great natural light, a game room, a

  Davey Hackett Parks Compass

  1657 Boswell Rd, Winchester, TN 37398
• 

  

  /49

  $587,500 Sold Mar 26, 2025

  794 River Watch Way, Winchester, TN 37398

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

  Last Sold Summary

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

  Current Estimated Value $584,483

  Last Listing Agent Susan Baker BHGRE Baker & Cole

  794 River Watch Way, Winchester, TN 37398
• 

  

  /42

  Est $271,667 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,744 Sq Ft

  306 6th Ave NW Unit 304, Winchester, TN 37398

  306 6th Ave NW Unit 304, Winchester, TN 37398
• 

  

  /15

  $230,000 Open Sun 8AM - 5PM

  • Land
  • 0.25 Acre
  • $920,000 per Acre

  0 Kayak Way Unit RTC3033545, Winchester, TN 37398

  JUST LISTED!!! LAKE VIEW LOT with water access! Don’t miss this highly sought-after lake view lot in the Twin Creeks Development. This is an excellent opportunity to build your dream home in a resort-style, golf cart friendly community. This lot is just a short ride to the marina, beach, hiking trails, fishing ponds, cabins, and campground. HOA includes mowing, access to 3 swimming pools, and use

  Felicia Wright Leading Edge Real Estate Group

  0 Kayak Way Unit RTC3033545, Winchester, TN 37398
• 

  

  /30

  $375,000 Sold Apr 11, 2025

  743 Hopkins Ln, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 2,457 Sq Ft
  • Built 1995

  Last Sold Summary

  • 15% Below List Price
  • $153/SF
  • 214 Days On Market

  Current Estimated Value $423,905

  Last Listing Agent Tyler Henley Franklin County Realty

  743 Hopkins Ln, Winchester, TN 37398
• 

  

  /33

  Est $394,642 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,772 Sq Ft

  513 N High St, Winchester, TN 37398

  513 N High St, Winchester, TN 37398
• 

  

  /31

  $280,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  406 Asia Rd, Winchester, TN 37398

  Well-kept estate property in Winchester's Asia Community just minutes from Tims Ford Lake! This home is in a quiet, country setting with all the charm not found in new builds. Home features 3 bedrooms and 2 full baths. Main bathroom with ceramic tile. Cozy den is perfect for relaxing with family and friends. The heart of this home is the kitchen with beautiful custom cabinets and hardwood

  Lashun Burks WEICHERT, REALTORS - The Andrews Group

  406 Asia Rd, Winchester, TN 37398
• 

  

  /58

  $310,000 Sold Jan 09, 2026

  131 Freedom Ln, Winchester, TN 37398

  • 5 Beds
  • 3 Baths
  • 2,429 Sq Ft
  • Built 1978

  Last Sold Summary

  • 7% Below List Price
  • $128/SF
  • 22 Days On Market

  Last Listing Agent Elizabeth Padgett Peck Realty Group, LLC

  131 Freedom Ln, Winchester, TN 37398
• 

  

  /24

  Est $151,086 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 964 Sq Ft

  800 Lynwood St, Winchester, TN 37398

  800 Lynwood St, Winchester, TN 37398
• 

  

  /30

  $289,900

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

  4025 David Crockett Pkwy W, Winchester, TN 37398

  Welcome to this unique piece of property just minutes from town. Home sits on a generous lot with lovely mature shade trees and flowers. Inside you will find 3bdr/1bath in the main home and in the attached mother-in law suite you will find an additional bedroom and bath. Mother-in law suite also features a kitchen and living room which can be accessed from the outside for great rental

  Angela Miller John Smith Jr Realty and Auction LLC

  4025 David Crockett Pkwy W, Winchester, TN 37398
• 

  

  /34

  $405,000 Sold Apr 16, 2025

  1487 S College St, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 3,187 Sq Ft
  • Built 1967

  Last Sold Summary

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

  Current Estimated Value $438,919

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

  1487 S College St, Winchester, TN 37398
• 

  

  /28

  Est $183,938 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft

  724 N High St, Winchester, TN 37398

  724 N High St, Winchester, TN 37398

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