Winchester, TN Homes

• 

  

  

  /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

  

  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

  

  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-

  

  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-

  

  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-

  

  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-

  

  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.

  

  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

  

  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

  

  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-

  

  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

  

  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

  

  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!

  

  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

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  (931) 283-6057

  59 Turtle Ct, Winchester, TN 37398

Showing Results 81 - 120, Page 3 of 18