Winchester, TN Homes

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  /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
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  /57

  $815,000 Sold Dec 05, 2025

  226 Kayak Way, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 2,219 Sq Ft
  • Built 2021

  Last Sold Summary

  • 2% Below List Price
  • $367/SF

  Last Listing Agent Dennis Sanders eXp Realty

  226 Kayak Way, Winchester, TN 37398
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  /65

  Est $1,235,813 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  397 Shasteen Bend Dr, Winchester, TN 37398

  397 Shasteen Bend Dr, 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
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  /16

  $130,000 Sold Aug 14, 2025

  0 River Watch Way Unit RTC2941024, Winchester, TN 37398

  • Land
  • 0.38 Acre
  • $342,105 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 6 Days On Market

  Last Listing Agent Jason Hilbelink Onward Real Estate

  0 River Watch Way Unit RTC2941024, Winchester, TN 37398
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  /36

  Est $352,083 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,773 Sq Ft

  155 Cooper Ln, Winchester, TN 37398

  155 Cooper Ln, 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
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  /2

  $980,000 Sold Apr 29, 2025

  1331 Dripping Springs Rd, Winchester, TN 37398

  • 3 Beds
  • 3 Baths
  • 1,391 Sq Ft
  • Built 1985

  Last Sold Summary

  • 2% Below List Price
  • $705/SF
  • 15 Days On Market

  Current Estimated Value $972,931

  Last Listing Agent John Peck Peck Realty Group, LLC

  1331 Dripping Springs Rd, Winchester, TN 37398
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  /32

  Est $363,738 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,768 Sq Ft

  716 Riva Lake Rd, Winchester, TN 37398

  716 Riva Lake Rd, 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
• 

  

  /22

  $226,000 Sold Apr 30, 2025

  211 N Jefferson St, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,956 Sq Ft
  • Built 1920

  Last Sold Summary

  • 19% Below List Price
  • $116/SF
  • 81 Days On Market

  Current Estimated Value $226,919

  Last Listing Agent Penny Patterson Swaffords Property Shop

  211 N Jefferson St, Winchester, TN 37398
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  /43

  Est $425,008 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft

  374 Woodcrest Dr, Winchester, TN 37398

  374 Woodcrest Dr, 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
• 

  

  /42

  $355,000 Sold Mar 07, 2025

  121 Edgefield Ct, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft
  • Built 2023

  Last Sold Summary

  • 1% Below List Price
  • $196/SF
  • 145 Days On Market

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

  121 Edgefield Ct, Winchester, TN 37398
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  /67

  Est $1,947,326 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 6,806 Sq Ft

  290 Shasteen Bend Dr, Winchester, TN 37398

  290 Shasteen Bend 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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  /2

  $459,000 Sold Mar 27, 2025

  484 Old Clark Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,817 Sq Ft
  • Built 2025

  Last Sold Summary

  • $253/SF
  • 0 Days On Market

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

  484 Old Clark Rd, Winchester, TN 37398
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  /58

  Est $491,860 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,448 Sq Ft

  271 Cedar Bluff Dr, Winchester, TN 37398

  271 Cedar Bluff Dr, 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
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  /55

  $281,000 Sold Jan 28, 2026

  218 Susie Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,446 Sq Ft
  • Built 1996

  Last Sold Summary

  • 8% Below List Price
  • $194/SF
  • 189 Days On Market

  Last Listing Agent Sean Crabtree Blue Door Realty Group

  218 Susie Dr, Winchester, TN 37398
• 

  

  /20

  Est $225,114 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  112 Cheyenne Ave, Winchester, TN 37398

  112 Cheyenne Ave, 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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  /6

  $125,000 Sold Jan 06, 2026

  3250 Lynchburg Rd, Winchester, TN 37398

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft
  • Built 1992

  Last Sold Summary

  • 17% Below List Price
  • $128/SF
  • 113 Days On Market

  Last Listing Agent Aleisha Putman Synergy Realty Network, LLC

  3250 Lynchburg Rd, Winchester, TN 37398
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  /32

  Est $282,956 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft

  766 Maple Bend Rd, Winchester, TN 37398

  766 Maple Bend Rd, 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
• 

  

  /70

  $640,000 Sold Oct 27, 2025

  239 River Watch Way, Winchester, TN 37398

  • 4 Beds
  • 3 Baths
  • 2,739 Sq Ft
  • Built 2018

  Last Sold Summary

  • 2% Below List Price
  • $234/SF
  • 327 Days On Market

  Last Listing Agent Zaya Holmes Compass

  239 River Watch Way, Winchester, TN 37398
• 

  

  /45

  Est $360,397 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,667 Sq Ft

  1132 Holders Cove Rd, Winchester, TN 37398

  1132 Holders Cove Rd, 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
• 

  

  /64

  $505,000 Sold May 01, 2025

  146 Brandi Way, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • Built 2009

  Last Sold Summary

  • 1% Below List Price
  • $243/SF
  • 102 Days On Market

  Current Estimated Value $507,788

  Last Listing Agent Melissa Wilson Southern Middle Realty

  146 Brandi Way, Winchester, TN 37398
• 

  

  /25

  Est $364,226 Not Listed For Sale

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

  463 Dripping Springs Rd, Winchester, TN 37398

  463 Dripping Springs Rd, 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
• 

  /2

  $45,000 Sold Mar 06, 2025

  0 Kay St, Winchester, TN 37398

  • Land
  • 0.45 Acre
  • $100,000 per Acre

  Last Sold Summary

  • 15 Days On Market

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

  0 Kay St, Winchester, TN 37398
• 

  

  /58

  Est $423,664 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,327 Sq Ft

  215 Franklin Heights Dr, Winchester, TN 37398

  215 Franklin Heights Dr, Winchester, TN 37398
• 

  

  /3

  $69,900

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

  0 Deer Valley Cir Unit RTC2980784, 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) 343-3768

  0 Deer Valley Cir Unit RTC2980784, Winchester, TN 37398
• 

  

  /30

  $1,050,000 Sold Jun 20, 2025

  62 Abby Cir, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,868 Sq Ft
  • Built 2022

  Last Sold Summary

  • 11% Below List Price
  • $366/SF
  • 20 Days On Market

  Current Estimated Value $1,074,347

  Last Listing Agent Grey Smotherman Reliant Realty ERA Powered

  62 Abby Cir, Winchester, TN 37398
• 

  

  /31

  Est $195,050 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft

  106 7th Ave SW, Winchester, TN 37398

  106 7th Ave SW, Winchester, TN 37398
• 

  

  /20

  $214,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  713 Hunt St, Winchester, TN 37398

  This beautifully designed 1064 sq ft home combines quality craftsmanship with modern comfort. Step inside to an open floor plan featuring quartz countertops, soft close cabinets, and luxury vinyl plank flooring throughout. The vaulted ceilings enhances the spacious feel of the kitchen and living area. The kitchen comes fully equipped with stainless steel appliances- stove, microwave, dishwasher,

  

  Shawna Denby

  1st Choice REALTOR

  (931) 369-2407

  713 Hunt St, Winchester, TN 37398
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  /38

  $260,000 Sold Aug 29, 2025

  115 Highland Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • Built 1952

  Last Sold Summary

  • 4% Below List Price
  • $192/SF
  • 96 Days On Market

  Current Estimated Value $256,121

  Last Listing Agent Fhonda Hatmaker eXp Realty

  115 Highland Dr, Winchester, TN 37398
• 

  

  /43

  Est $1,209,485 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,512 Sq Ft

  18 Brown Rd E, Winchester, TN 37398

  18 Brown Rd E, Winchester, TN 37398
• 

  

  /24

  $204,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  540 Milton Ln, Winchester, TN 37398

  This 1064 sq ft home offers modern finishes with a funtional layout. Featuring granite countertops and soft close kitchen cabinets. Luxury vinyl flooring throughout. The vaulted ceilings in the kitchen and livingroom elevate these common areas. The kitchen is equipped with a stove, microwave, dishwasher, and refrigerator. Convenient stackable washer and dryer also included. Enjoy the outdoors

  

  Shawna Denby

  1st Choice REALTOR

  (931) 575-5281

  540 Milton Ln, Winchester, TN 37398

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