Winchester, TN Homes

• 

  

  

  /16

  $175,000

  Sold Sep 08, 2025

  148 Galloway Ln, Winchester, TN 37398

  Last Sold Summary

  • 45% Below List Price
  • 46 Days On Market

  Last Listing Agent Tabitha Staples Sewanee Realty

  148 Galloway Ln, Winchester, TN 37398
• 

  

  

  /50

  Est $1,142,372

  Not Listed For Sale

  326 Loop Dr, Winchester, TN 37398

  • 3 Beds
  • 3 Baths
  • 3,154 Sq Ft
  • Built 1984

  326 Loop Dr, Winchester, TN 37398

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Patricia Mathis Lake Homes Realty, LLC
• 

  

  

  /84

  $1,650,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,900 Sq Ft

  220 Deer View Ln, Winchester, TN 37398

  This stunning Franklin County, Tennessee, farm offers a pristine rural setting for those seeking a beautiful 3 bedroom, 2 bathroom home with acreage! The property includes +/- 50 acres of highly productive tillable land, yielding exceptional row crops, alongside rolling pastures, barns, and gorgeous front porch views. The updated home provides ample space for a growing family or future expansion.

  Brian Whitt Arrowhead Land Company

  220 Deer View Ln, Winchester, TN 37398
• 

  

  

  /33

  $285,000

  Sold Dec 11, 2025

  145 Susie Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft
  • Built 1997

  Last Sold Summary

  • 1% Below List Price
  • $176/SF
  • 24 Days On Market

  Current Estimated Value $302,902

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

  145 Susie Dr, Winchester, TN 37398
• 

  

  

  /43

  Est $543,858

  Not Listed For Sale

  80 Huntington Dr N, Winchester, TN 37398

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

  80 Huntington Dr N, Winchester, TN 37398

  Last Sold Summary

  • 94 Days On Market

  Last Listing Agent Alexandra Watts Southern Middle Realty
• 

  /2

  $249,900

  $25K PRICE DROP

  • 1,930 Sq Ft

  810 N High St, Winchester, TN 37398

  Great duplex in perfect location...convenient to Tims Ford lake, Twin Creeks marina and downtown Winchester! One side had an extensive overhaul in 2025. Both sides are currently rented at 975.00 each. Great return on your money! Allow 24hr showing notice to alert tenants.

  Curtis Benchmark Realty, LLC

  810 N High St, Winchester, TN 37398
• 

  

  /14

  $221,400

  Sold Aug 12, 2025

  707 Hunt St, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 2024

  Last Sold Summary

  • 11% Below List Price
  • $188/SF
  • 57 Days On Market

  Last Listing Agent Shawna Denby 1st Choice REALTOR

  707 Hunt St, Winchester, TN 37398
• 

  

  /47

  Est $191,384

  Not Listed For Sale

  4756 Old Tullahoma Rd, Winchester, TN 37398

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft
  • Built 1955

  4756 Old Tullahoma Rd, Winchester, TN 37398

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Jessica London Southern Middle Realty
• 

  

  /45

  $997,500

  $2K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  423 Shasteen Bend Dr, Winchester, TN 37398

  Nestled in the exclusive community of Lee Ford Estates, this exceptional lakefront retreat offers breathtaking waterfront living just minutes from downtown Winchester. Designed to maximize the beauty of the lake from every angle, the home features French doors throughout, creating stunning panoramic water views and seamless indoor-outdoor living. This beautiful home offers 3 bedrooms and 2 baths,

  Yvonne Stewart Winton Auction & Realty Co.

  423 Shasteen Bend Dr, Winchester, TN 37398
• 

  

  /79

  $710,000

  Sold Aug 21, 2025

  106 Hammock Dr, Winchester, TN 37398

  • 3 Beds
  • 3.5 Baths
  • 3,028 Sq Ft
  • Built 2022

  Last Sold Summary

  • 11% Below List Price
  • $234/SF
  • 33 Days On Market

  Current Estimated Value $767,015

  Last Listing Agent Tara Hays Benchmark Realty, LLC

  106 Hammock Dr, Winchester, TN 37398
• 

  

  /10

  Est $114,288

  Not Listed For Sale

  512 Elm St, Winchester, TN 37398

  • 2 Beds
  • 1 Bath
  • 948 Sq Ft
  • Built 1942

  512 Elm St, Winchester, TN 37398

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Bj Rigsby Lynch Rigsby Realty & Auction, LLC
• 

  

  /38

  $344,900

  New Construction $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  253 Brookfield Cir, Winchester, TN 37398

  Beautiful NEW construction just minutes away from Twin Creeks Marina! This beautifully crafted home features a durable Hardiboard exterior and an inviting open floor plan designed for comfortable everyday living and entertaining. Split bedroom concept, luxury vinyl flooring in main living areas, custom shelving in all closets and pantry, walk in tile shower in primary bathroom, stunning lighting

  Jackson Lynch Lynch Rigsby Realty & Auction, LLC

  253 Brookfield Cir, Winchester, TN 37398
• 

  /2

  $18,000

  Sold Mar 30, 2026

  1508 Old Cowan Rd, Winchester, TN 37398

  • Land
  • 13,068 Sq Ft
  • $60,000 per Acre

  Last Sold Summary

  Current Estimated Value $96,000

  Last Listing Agent Aleisha Putman Synergy Realty Network, LLC

  1508 Old Cowan Rd, Winchester, TN 37398
• 

  

  /63

  Est $1,683,129

  Not Listed For Sale

  20 W Rockcrest Cir, Winchester, TN 37398

  • 3 Beds
  • 3 Baths
  • 2,546 Sq Ft
  • Built 2000

  20 W Rockcrest Cir, Winchester, TN 37398

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Christy Frewin Vastland Realty Group, LLC
• 

  

  /17

  $1,199,000

  • 4 Beds
  • 6 Baths
  • 3,812 Sq Ft

  221 Hammock Dr, Winchester, TN 37398

  BEST LAKE VIEW in the neighborhood and MULTIPLE RESORT STYLE SWIMMING POOLS!!! Welcome to 221 Hammock Drive, an exceptional custom residence located in the prestigious Twin Creeks Village community. Built in 2022, this approximately 3,812-square-foot home boasts 4 BR, 4BTH and 2 HBTH and offers a Master Bedroom on the main and second floor. Step inside to a luxurious feel and open floorplan and

  Howard Hicks Benchmark Realty, LLC

  221 Hammock Dr, Winchester, TN 37398
• 

  

  /17

  $610,000

  Sold May 29, 2026

  57 Wakeboard Way, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 1,939 Sq Ft
  • Built 2020

  Last Sold Summary

  • 2% Above List Price
  • $315/SF
  • 2 Days On Market

  Current Estimated Value $608,101

  Last Listing Agent Daniel Demers Sell Your Home Services, LLC

  57 Wakeboard Way, Winchester, TN 37398
• 

  

  /29

  Est $151,022

  Not Listed For Sale

  407 Plattenburg St, Winchester, TN 37398

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft
  • Built 1932

  407 Plattenburg St, Winchester, TN 37398

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Gary Ashton The Ashton Real Estate Group of RE/MAX Advantage
• 

  

  /17

  $299,999

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,213 Sq Ft

  99 N Shephard St, Winchester, TN 37398

  Welcome to Green River—where front porch living, walkable convenience, and small-town charm come together. Located just a half-mile from Winchester’s historic square and only 1.5 miles from Tims Ford Lake, this brand-new home offers the perfect balance of downtown accessibility and outdoor recreation. Enjoy local dining, shopping, festivals, boating, and lake days—all just minutes from your front

  Ashley Nelson Franklin County Realty

  99 N Shephard St, Winchester, TN 37398
• 

  

  /23

  $280,000

  Sold Aug 15, 2025

  0 Anderton Dr, Winchester, TN 37398

  • Land
  • 2.99 Acres
  • $93,771 per Acre

  Last Sold Summary

  • 26% Below List Price
  • 28 Days On Market

  Last Listing Agent isaac zimmerle Benchmark Realty, LLC

  0 Anderton Dr, Winchester, TN 37398
• 

  

  /38

  Est $310,127

  Not Listed For Sale

  107 Jensen Ln, Winchester, TN 37398

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1979

  107 Jensen Ln, Winchester, TN 37398

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Sam Hatfield Sam Hatfield Realty, Inc.
• 

  

  /19

  $205,000

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,333 Sq Ft

  205 8th Ave NW, Winchester, TN 37398

  Welcome to this delightful brick home nestled on a generous corner lot surrounded by mature shade trees. Full of character and timeless appeal, this home features gleaming original hardwood floors that add warmth and authenticity throughout. Perfectly situated close to town and just minutes from Tims Ford Lake. This combines peaceful living with everyday convenience. Replacement windows

  Angela Miller John Smith Jr Realty and Auction LLC

  205 8th Ave NW, Winchester, TN 37398
• 

  

  /70

  $570,000

  Sold Dec 12, 2025

  504 River Watch Way, Winchester, TN 37398

  • 4 Beds
  • 3 Baths
  • 2,906 Sq Ft
  • Built 2022

  Last Sold Summary

  • 12% Below List Price
  • $196/SF
  • 226 Days On Market

  Current Estimated Value $611,272

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

  504 River Watch Way, Winchester, TN 37398
• 

  

  /65

  Est $1,178,546

  Not Listed For Sale

  397 Shasteen Bend Dr, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 1989

  397 Shasteen Bend Dr, Winchester, TN 37398

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Sam Hatfield Sam Hatfield Realty, Inc.
• 

  /2

  Call for Price

  Pending

  • 2 Beds
  • 1 Bath
  • 1,014 Sq Ft

  408 S Shephard St, Winchester, TN 37398

  Sold As Is at Auction July 18 @ !2 Noon subject to Chancery Court Approval. Note a 25ftx142 additional lot will be Sold with the house and lot giving a total frontage of 106 ft per tax Info, which will give it Duplex Construction approval per lot size.

  John Smith, Jr. John Smith Jr Realty and Auction LLC

  408 S Shephard St, Winchester, TN 37398
• 

  

  /27

  $218,000

  Sold Jun 18, 2026

  213 S Porter St, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 1,575 Sq Ft
  • Built 2025

  Last Sold Summary

  • 27% Below List Price
  • $138/SF
  • 50 Days On Market

  Last Listing Agent Grey Smotherman Reliant Realty ERA Powered

  213 S Porter St, Winchester, TN 37398
• 

  

  /36

  Est $332,369

  Not Listed For Sale

  155 Cooper Ln, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 1,773 Sq Ft
  • Built 1966

  155 Cooper Ln, Winchester, TN 37398

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Jenny Orr WEICHERT, REALTORS Joe Orr & Associates
• 

  

  /33

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  266 Woods Edge Rd, Winchester, TN 37398

  Welcome to your forever haven - where comfort meets timeless charm. Step inside to vaulted ceilings with exposed beam, a ceiling fan, and rich finished wood floors that flow seamlessly into the living area. Cozy up by the natural gas fireplace or open the dining room's double doors to a sun-drenched three-season room - your retreat for morning coffee or evening breezes. The kitchen is sure to

  Sharon Swafford Swaffords Property Shop

  266 Woods Edge Rd, Winchester, TN 37398
• 

  

  /44

  $313,000

  Sold Jan 06, 2026

  196 Brookfield Cir, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,194 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Above List Price
  • $262/SF
  • 6 Days On Market

  Current Estimated Value $318,920

  Last Listing Agent Dennis Sanders eXp Realty

  196 Brookfield Cir, Winchester, TN 37398
• 

  

  /32

  Est $368,637

  Not Listed For Sale

  716 Riva Lake Rd, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 1,768 Sq Ft
  • Built 1975

  716 Riva Lake Rd, Winchester, TN 37398

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent John Peck Century 21 Volunteer Realty
• 

  /2

  $59,900

  $3K PRICE DROP Under Contract

  • Land
  • 12,632 Sq Ft
  • $206,552 per Acre

  0 Lookout Dr Unit 12, Winchester, TN 37398

  This lot is ready for your new home! Bring your own builder or use our preferred builder! Water, Sewer and gas available. Underground utilities. Gated Community with Common area. 1800 square foot minimum. Located less than one minute from Tim's Ford Lake (public boat launch on Sharp Springs Rd). Convenient to shopping and dining. Taxes are for land only - Owner Agent

  Nick Jenkins Go Realty, LLC

  0 Lookout Dr Unit 12, Winchester, TN 37398
• 

  

  /81

  $799,900

  Sold Jun 29, 2026

  17 Cannonball Ct, Winchester, TN 37398

  • 4 Beds
  • 3.5 Baths
  • 2,989 Sq Ft
  • Built 2021

  Last Sold Summary

  • 4% Below List Price
  • $268/SF
  • 95 Days On Market

  Current Estimated Value $781,433

  Last Listing Agent Jennifer Watson Exit Truly Home Realty

  17 Cannonball Ct, Winchester, TN 37398
• 

  

  /51

  Est $800,138

  Not Listed For Sale

  994 Cline Ridge Rd, Winchester, TN 37398

  • 3 Beds
  • 3 Baths
  • 2,982 Sq Ft
  • Built 1987

  994 Cline Ridge Rd, Winchester, TN 37398

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Jenny Orr WEICHERT, REALTORS Joe Orr & Associates
• 

  /2

  Call for Price

  Pending

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  184 Edgewood Ln, Winchester, TN 37398

  Selling at Auction July 18 @ 9:30 am Subject to Chancery Court Approval

  John Smith, Jr. John Smith Jr Realty and Auction LLC

  184 Edgewood Ln, Winchester, TN 37398
• 

  

  /77

  $615,000

  Sold Jul 10, 2026

  192 Bell Dr W, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 3,040 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Below List Price
  • $202/SF
  • 61 Days On Market

  Current Estimated Value $628,458

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

  192 Bell Dr W, Winchester, TN 37398
• 

  

  /32

  Est $253,453

  Not Listed For Sale

  278 Cessna Cir, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2002

  278 Cessna Cir, Winchester, TN 37398

  Last Sold Summary

  • 141 Days On Market

  Last Listing Agent Crystal Hill RE/MAX 1st Realty
• 

  

  /89

  $774,900

  • 3 Beds
  • 4 Baths
  • 3,241 Sq Ft

  153 Cascade Dr, Winchester, TN 37398

  Custom-built by a local builder, this exceptional home combines quality craftsmanship, luxury upgrades, and thoughtfully designed indoor-outdoor living. From the professionally landscaped curb appeal to the fenced backyard, every detail has been carefully considered. Inside, you'll find an open-concept floor plan centered around a stunning custom kitchen featuring premium finishes, a large

  Robbie Roate Benchmark Realty, LLC

  153 Cascade Dr, Winchester, TN 37398
• 

  

  /58

  $745,000

  Sold Mar 26, 2026

  20 Windjammer Ct, Winchester, TN 37398

  • 4 Beds
  • 3 Baths
  • 3,032 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $246/SF
  • 12 Days On Market

  Current Estimated Value $737,005

  Last Listing Agent Felicia Wright Leading Edge Real Estate Group

  20 Windjammer Ct, Winchester, TN 37398
• 

  

  /43

  Est $423,284

  Not Listed For Sale

  374 Woodcrest Dr, Winchester, TN 37398

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 1986

  374 Woodcrest Dr, Winchester, TN 37398

  Last Sold Summary

  • 133 Days On Market

  Last Listing Agent Steve Jernigan Steve Jernigan Realty
• 

  

  /35

  $229,500

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

  1102 N High St, Winchester, TN 37398

  Discover this delightful all-brick home, perfect as a starter abode or a savvy investment opportunity! Nestled on a spacious lot, this property offers much. Just a 30-second drive to the city park and boat ramp. This home boasts a large backyard with a small, fenced area next to the back door, ideal for your furry friends. Extra storage room on the carport for convenience. Inviting hardwood and

  Sharon Swafford Swaffords Property Shop

  1102 N High St, Winchester, TN 37398
• 

  

  /35

  $1,450,000

  Sold Oct 24, 2025

  130 Phillips Dr, Winchester, TN 37398

  • 3 Beds
  • 4.5 Baths
  • 4,193 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Below List Price
  • $346/SF
  • 72 Days On Market

  Current Estimated Value $1,513,180

  Last Listing Agent Heather Boldizsar Lake Homes Realty, LLC

  130 Phillips Dr, Winchester, TN 37398

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