Winchester, TN Homes

• 

  

  

  /5

  $60,000

  Sold Aug 13, 2025

  0 Lynchburg Rd Unit RTC2899282, Winchester, TN 37398

  • Land
  • 37,897 Sq Ft
  • $68,966 per Acre

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  0 Lynchburg Rd Unit RTC2899282, Winchester, TN 37398
• 

  

  

  /34

  Est $444,697

  Not Listed For Sale

  261 Dry Creek Ln, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 2,230 Sq Ft
  • Built 1993

  261 Dry Creek Ln, Winchester, TN 37398

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Darian Norman Southern Middle Realty
• 

  

  

  /62

  $559,500

  • 4 Beds
  • 2.5 Baths
  • 2,494 Sq Ft

  92 Freeman Ct, Winchester, TN 37398

  Welcome to 92 Freeman Court in Winchester, Tennessee, where comfort, convenience, and exceptional amenities come together just minutes from Historic Downtown Winchester and beautiful Tims Ford Lake. Enjoy easy access to multiple nearby boat launches, marinas, and waterfront recreation, making this property ideal for lake lovers and outdoor enthusiasts. This well-maintained home features beautiful

  Misty Guzman Century 21 Wright Realty

  92 Freeman Ct, Winchester, TN 37398
• 

  

  

  /18

  $280,000

  Sold Sep 11, 2025

  117 Raspberry Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,489 Sq Ft
  • Built 2018

  Last Sold Summary

  • 8% Below List Price
  • $188/SF
  • 88 Days On Market

  Current Estimated Value $296,377

  Last Listing Agent John Smith, Jr. John Smith Jr Realty and Auction LLC

  117 Raspberry Dr, Winchester, TN 37398
• 

  

  

  /17

  Est $251,066

  Not Listed For Sale

  1338 Blue Spring Rd, Decherd, TN 37324

  • 2 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • Built 1965

  1338 Blue Spring Rd, Decherd, TN 37324

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Donna Barber Synergy Realty Network, LLC
• 

  

  /9

  $1,400,000

  $400K PRICE DROP

  • Land
  • 25.15 Acres
  • $55,666 per Acre

  3819 Tullahoma Hwy, Winchester, TN 37398

  Prime opportunity on Hwy 41A! 25 acres with road frontage along Tullahoma Highway, currently zoned agricultural but offering excellent potential for rezoning to commercial use. This property is located in a high-traffic corridor with strong visibility, making it ideal for future development. Rare chance to secure acreage in such a prime location—don’t miss it! Less than 0.8 miles to Home Depot

  Jennifer Murdock Horizon Realty Group dba Keller Williams Horizon

  3819 Tullahoma Hwy, Winchester, TN 37398
• 

  

  /50

  $299,900

  Sold Nov 13, 2025

  115 Oak Leaf Cir, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Built 1990

  Last Sold Summary

  • $204/SF
  • 12 Days On Market

  Current Estimated Value $307,732

  Last Listing Agent Jessica London Southern Middle Realty

  115 Oak Leaf Cir, Winchester, TN 37398
• 

  

  /44

  Est $983,660

  Not Listed For Sale

  363 Wildwood Cir, Winchester, TN 37398

  • 4 Beds
  • 2 Baths
  • 2,160 Sq Ft
  • Built 1992

  363 Wildwood Cir, Winchester, TN 37398

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent John Peck Century 21 Volunteer Realty
• 

  /2

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,544 Sq Ft

  171 Raspberry Dr, Winchester, TN 37398

  Welcome home to this beautifully maintained 3-bedroom, 2-bath home located in a quiet, family-friendly neighborhood! Conveniently situated between the historic Winchester Square and the recreational beauty of Tim’s Ford Lake. This home offers the perfect blend of small-town charm and everyday convenience. Step inside to an inviting open-concept floor plan featuring warm wood flooring,

  Sommer Denby Southern Elite Realty

  171 Raspberry Dr, Winchester, TN 37398
• 

  

  /55

  $439,900

  Sold Dec 02, 2025

  197 Murray Lake Dr, Winchester, TN 37398

  • 3 Beds
  • 3 Baths
  • 2,528 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Below List Price
  • $174/SF
  • 22 Days On Market

  Current Estimated Value $454,451

  Last Listing Agent David Janke Canopy Real Estate

  197 Murray Lake Dr, Winchester, TN 37398
• 

  

  /19

  Est $326,466

  Not Listed For Sale

  221 Ridgefield Cir, Winchester, TN 37398

  • 2 Beds
  • 1.5 Baths
  • 1,616 Sq Ft
  • Built 1978

  221 Ridgefield Cir, Winchester, TN 37398

  Last Sold Summary

  • 127 Days On Market

  Last Listing Agent Candice Lynn Realty One Group Music City
• 

  

  /53

  $443,900

  New Construction $41K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,290 Sq Ft

  108 Lookout Dr, Winchester, TN 37398

  Welcome to this beautiful 1.5-level home designed for comfort, convenience, and style! This 3-bedroom home features a zoned primary suite on the main floor, offering privacy and functionality for modern living. The open-concept layout creates an inviting space perfect for entertaining family and friends, while the spacious covered back porch provides the ideal spot to relax and unwind outdoors.

  Mitchell Bowman simpliHOM - The Results Team

  108 Lookout Dr, Winchester, TN 37398
• 

  

  /42

  $220,000

  Sold Jul 30, 2026

  1466 Bible Crossing Rd, Winchester, TN 37398

  • 2 Beds
  • 1 Bath
  • 1,116 Sq Ft
  • Built 1948

  Last Sold Summary

  • 7% Below List Price
  • $197/SF
  • 31 Days On Market

  Current Estimated Value $227,311

  Last Listing Agent Marcia Long Franklin County Realty

  1466 Bible Crossing Rd, Winchester, TN 37398
• 

  

  /27

  Est $344,647

  Not Listed For Sale

  404 Lynchburg Rd, Winchester, TN 37398

  • 4 Beds
  • 1.5 Baths
  • 2,450 Sq Ft
  • Built 1900

  404 Lynchburg Rd, Winchester, TN 37398

  Last Sold Summary

  • 107 Days On Market

  Last Listing Agent Leah Edwards StillWater Realty & Auction
• 

  

  /15

  $195,000

  • Land
  • 1.35 Acres
  • $144,444 per Acre

  16 Cascade Dr, Winchester, TN 37398

  Build your dream home on this beautiful lot located in luxurious Stone Field Heights subdivision. Lot 16 is one of the largest lots (1.35 acres) which includes mature trees, city water, natural gas, underground utilities and sewer connections. Because it is located in the back of the subdivision, you will enjoy a very private, large back yard with over 230' width at the rear of the lot. Stone

  Lisa Hayes 1st Choice REALTOR

  16 Cascade Dr, Winchester, TN 37398
• 

  

  /46

  $275,000

  Sold Feb 20, 2026

  41 Cheyenne Ave, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,563 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Below List Price
  • $176/SF
  • 40 Days On Market

  Current Estimated Value $286,207

  Last Listing Agent Connie Landers BHGRE Baker & Cole

  41 Cheyenne Ave, Winchester, TN 37398
• 

  

  /61

  Est $667,139

  Not Listed For Sale

  95 Freeman Ct, Winchester, TN 37398

  • 5 Beds
  • 4 Baths
  • 5,018 Sq Ft
  • Built 2004

  95 Freeman Ct, Winchester, TN 37398

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Matt Sargent Matt Sargent Homes
• 

  

  /19

  $139,900

  $25K PRICE DROP

  • Land
  • 0 Sq Ft

  0 Dry Fork Dr Unit 50, Winchester, TN 37398

  MOTIVATED SELLER!!! One of the LAST remaining WATER VIEW building lots in beautiful Twin Creeks Village! Lot #50 Dry Fork Dr is a premium location to build your dream home overlooking the water — just imagine ending every day on your back porch with a front-row seat to the sunset over Tims Ford Lake. This resort-style, golf-cart-friendly community gives you access to THREE swimming pools,

  Felicia Wright Leading Edge Real Estate Group

  0 Dry Fork Dr Unit 50, Winchester, TN 37398
• 

  

  /30

  $295,000

  Sold Apr 30, 2026

  1956 Old Estill Springs Rd, Winchester, TN 37398

  • 3 Beds
  • 1.5 Baths
  • 1,668 Sq Ft
  • Built 1977

  Last Sold Summary

  • 6% Below List Price
  • $177/SF
  • 1 Day On Market

  Current Estimated Value $301,822

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  1956 Old Estill Springs Rd, Winchester, TN 37398
• 

  

  /42

  Est $569,678

  Not Listed For Sale

  610 Shadowbrook Rd, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2002

  610 Shadowbrook Rd, Winchester, TN 37398

  Last Sold Summary

  • 78 Days On Market

  Last Listing Agent Billie Kay Caldwell Swaffords Property Shop
• 

  

  /30

  $310,999

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft

  101 Royal Oak Dr, Winchester, TN 37398

  Welcome to this well-maintained 3 bedroom, 2 bath brick home situated on 1.3 acre lot in a quiet well-established neighborhood just minutes from the lake. This charming property offers the perfect balance of privacy space and convenience, making it ideal for families, downsizing, or anyone looking to enjoy peaceful living close to outdoor recreation. The home features a bright and inviting living

  Chesney Luttrell John Smith Jr Realty and Auction LLC

  101 Royal Oak Dr, Winchester, TN 37398
• 

  

  /26

  $413,500

  Sold Nov 14, 2025

  53 Summerset Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,813 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Below List Price
  • $228/SF
  • 10 Days On Market

  Last Listing Agent Amanda Koziol eXp Realty

  53 Summerset Dr, Winchester, TN 37398
• 

  

  /38

  Est $373,657

  Not Listed For Sale

  3723 Keith Cove Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,451 Sq Ft
  • Built 1997

  3723 Keith Cove Rd, Winchester, TN 37398

  Last Sold Summary

  • 1 Day On Market

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

  

  /36

  $325,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft

  1543 Paynes Church Rd, Winchester, TN 37398

  **Move in for only $99 AND a fixed rate as low as 5.5%** BRAND NEW! ONE LEVEL, 3BD | 2BTH home LVP flooring throughout, NO CARPET OR STAIRS! ideal for easy maintenance! The kitchen features custom cabinetry, and SS kitchen appliances with brush nickel finishes. Open Concept layout & split bedroom floorplan- providing added privacy to the primary suite. This large yard offers plenty of space to

  Kasidy Lowe Compass Tennessee, LLC

  1543 Paynes Church Rd, Winchester, TN 37398
• 

  

  /30

  $390,000

  Sold Nov 21, 2025

  1050 Franklin Heights Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 2,346 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Below List Price
  • $166/SF
  • 5 Days On Market

  Current Estimated Value $422,487

  Last Listing Agent Billie Kay Caldwell Swaffords Property Shop

  1050 Franklin Heights Dr, Winchester, TN 37398
• 

  

  /19

  Est $302,887

  Not Listed For Sale

  41 Carol Cir, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,413 Sq Ft
  • Built 1989

  41 Carol Cir, Winchester, TN 37398

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Sharon Swafford Swaffords Property Shop
• 

  

  /14

  $64,999

  Under Contract

  • Land
  • 12,196 Sq Ft
  • $232,139 per Acre

  0 Lookout Dr Unit 43, Winchester, TN 37398

  Available now in The Highlands! Convenient access to Tim's Ford Lake and Downtown Winchester, this is a sought-after neighborhood for good reason! This lot (43) is available as well as the neighboring lot right next door (Lot 42). Water, Sewer, and Gas available. Ask about our builder incentive!

  Alexia Cain Home and Farms Inc

  0 Lookout Dr Unit 43, Winchester, TN 37398
• 

  

  /8

  $285,000

  Sold Dec 11, 2025

  1549 Mansford Rd, Winchester, TN 37398

  • Land
  • 12.7 Acres
  • $22,441 per Acre

  Last Sold Summary

  • 90% Above List Price
  • 69 Days On Market

  Current Estimated Value $405,181

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  1549 Mansford Rd, Winchester, TN 37398
• 

  

  /20

  Est $169,489

  Not Listed For Sale

  723 N Vine St, Winchester, TN 37398

  • 2 Beds
  • 1 Bath
  • 869 Sq Ft
  • Built 1945

  723 N Vine St, Winchester, TN 37398

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Elisa Chessor Century 21 Coffee County Realty & Auction
• 

  /2

  $110,000

  • Land
  • 37,461 Sq Ft
  • $127,907 per Acre

  0 Summer Lake Unit 4, Winchester, TN 37398

  Build your new home in this quiet and secluded subdivision. Walking trail for all lot owners to access the trail to Owl Hollow Cove on the Tims Ford Lake. Summer Lake TVA Access Trail for golf carts, ATV, bicycle, hiking, paddle boat, swimming and fishing. Boats can be driven into the cove. Currently a boat dock is not permitted but there are several boat docks within a short distance of the

  Yvette Lowe Century 21 Coffee County Realty & Auction

  0 Summer Lake Unit 4, Winchester, TN 37398
• 

  

  /20

  $235,000

  Sold Jan 28, 2026

  114 11th Ave NW, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $226/SF
  • 5 Days On Market

  Current Estimated Value $238,546

  Last Listing Agent Ben Absher Realty One Group Experts

  

  114 11th Ave NW, Winchester, TN 37398
• 

  

  /42

  Est $1,251,967

  Not Listed For Sale

  321 Wildwood Cir, Winchester, TN 37398

  • 3 Beds
  • 3.5 Baths
  • 2,769 Sq Ft
  • Built 2002

  321 Wildwood Cir, Winchester, TN 37398

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Elizabeth Huddleston Keller Williams Realty Nashville/Franklin
• 

  

  /4

  $94,900

  $14K PRICE DROP

  • Land
  • 2.44 Acres
  • $38,893 per Acre

  0 Sugar Leaf Cir Unit Lot 31, Winchester, TN 37398

  Build your dream home on this 2.44-acre lot! There’s plenty of space and room for privacy, with a minimum house size of 1,800 sq. ft. Public utilities at street-water, sewer, electricity, cable, telephone. There is a small inactive sinkhole on the back of the property that poses no threats according to the geological report that is listed under documents

  Jackson Lynch Lynch Rigsby Realty & Auction, LLC

  0 Sugar Leaf Cir Unit Lot 31, Winchester, TN 37398
• 

  

  /5

  $65,000

  Sold Mar 02, 2026

  0 Ridgecrest Dr Unit RTC2986099, Winchester, TN 37398

  • Land
  • 25,264 Sq Ft
  • $112,069 per Acre

  Last Sold Summary

  • 32% Below List Price
  • 157 Days On Market

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

  0 Ridgecrest Dr Unit RTC2986099, Winchester, TN 37398
• 

  

  /21

  Est $332,361

  Not Listed For Sale

  102 Ridgefield Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,765 Sq Ft
  • Built 1986

  102 Ridgefield Dr, Winchester, TN 37398

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Josh Cook Benchmark Realty, LLC
• 

  

  /7

  $79,900

  $5K PRICE DROP

  • Land
  • 6,359 Sq Ft
  • $547,260 per Acre

  0 River Watch Way Unit 364, Winchester, TN 37398

  Motivated Sellers! All reasonable offers considered. Come enjoy this Summer ! Get access to all the amenities and enjoy your weekends at the lake This level lot is ready for your dream home! Bring the house plans. (The lot next door *365, MLS * is also for sale so you could build on both lots. Located in family-friendly, gated lakeside community, Twin Creeks offers everything you need for

  Amy Rivera Marcoma Realty, Inc.

  0 River Watch Way Unit 364, Winchester, TN 37398
• 

  

  /43

  $459,000

  Sold Apr 03, 2026

  300 Old Clark Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $249/SF
  • 39 Days On Market

  Current Estimated Value $458,667

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

  300 Old Clark Rd, Winchester, TN 37398
• 

  

  /14

  Est $221,385

  Not Listed For Sale

  214 8th Ave SW, Winchester, TN 37398

  • 9 Beds
  • 6 Baths
  • 3,366 Sq Ft
  • Built 2024

  214 8th Ave SW, Winchester, TN 37398

  Last Sold Summary

  • 183 Days On Market

  Last Listing Agent Daryl Welch Freedom Realty Group
• 

  

  /38

  $825,000

  Open House 8/16

  • 3 Beds
  • 2.5 Baths
  • 2,611 Sq Ft

  150 Edie Mae Ln, Winchester, TN 37398

  Escape to your own private Tennessee retreat on 9 picturesque acres just minutes from Tims Ford Lake! This stunning 3-bedroom, 2.5-bath custom home offers the perfect blend of modern comfort, peaceful country living, and recreational convenience. Built in 2020, the thoughtfully designed open floor plan features abundant natural light, soaring ceilings, built-in cabinetry, and a cozy wood-burning

  Matt Sargent Matt Sargent Homes

  150 Edie Mae Ln, Winchester, TN 37398
• 

  

  /4

  $111,100

  Sold Jul 24, 2026

  0 River Watch Way Unit RTC3246455, Winchester, TN 37398

  • Land
  • 24,393 Sq Ft
  • $198,393 per Acre

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent James R. Cash James R. Cash II Auctions & Real Estate

  0 River Watch Way Unit RTC3246455, Winchester, TN 37398

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