Winchester, TN Homes

• 

  

  

  /8

  $110,000

  Sold Nov 14, 2025

  0 Old Cowan Rd Unit RTC2970796, Winchester, TN 37398

  • Land
  • 32,103 Sq Ft
  • $149,254 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 63 Days On Market

  Last Listing Agent Sean Crabtree Blue Door Realty Group

  0 Old Cowan Rd Unit RTC2970796, Winchester, TN 37398
• 

  

  

  /10

  Est $122,263

  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
• 

  

  

  /54

  $460,000

  Sold Mar 02, 2026

  67 Summerset Dr, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,543 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $181/SF
  • 29 Days On Market

  Last Listing Agent Mena Shaker Dream Homes Realty

  67 Summerset Dr, Winchester, TN 37398
• 

  

  

  /63

  Est $1,669,433

  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
• 

  

  /53

  $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
• 

  

  /26

  $1,550,000

  Sold Nov 25, 2025

  947 Fanning Bend Dr, Winchester, TN 37398

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

  Last Sold Summary

  • 3% Below List Price
  • $356/SF
  • 19 Days On Market

  Current Estimated Value $1,661,965

  Last Listing Agent Mikayla Wurth Southern Middle Realty

  947 Fanning Bend Dr, Winchester, TN 37398
• 

  

  /29

  Est $157,248

  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

  $295,999

  New Construction $4K PRICE DROP

  • 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
• 

  

  /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 $301,074

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

  145 Susie Dr, Winchester, TN 37398
• 

  

  /38

  Est $344,967

  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 Pending

  • 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
• 

  /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 $18,000

  Last Listing Agent Aleisha Putman Synergy Realty Network, LLC

  1508 Old Cowan Rd, Winchester, TN 37398
• 

  

  /65

  Est $1,322,733

  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
• 

  

  /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 $612,983

  Last Listing Agent Daniel Demers Sell Your Home Services, LLC

  57 Wakeboard Way, Winchester, TN 37398
• 

  

  /36

  Est $368,440

  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

  $299,900

  $35K PRICE DROP

  • 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
• 

  

  /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 $607,994

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

  504 River Watch Way, Winchester, TN 37398
• 

  

  /32

  Est $375,824

  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

  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
• 

  

  /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
• 

  

  /51

  Est $841,581

  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
• 

  

  /89

  $774,900

  Under Contract

  • 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
• 

  

  /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 $314,748

  Last Listing Agent Dennis Sanders eXp Realty

  196 Brookfield Cir, Winchester, TN 37398
• 

  

  /32

  Est $271,551

  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
• 

  

  /3

  $580,458

  • 3 Beds
  • 2 Baths
  • 2,274 Sq Ft

  0 Deer Valley Unit 3529310, Winchester, TN 37398

  Winchesters newest 55 plus community ideal for low maintenance living. This new neighborhood features amenities such as Clubhouse, fitness center , pool, dog park and lawn maintenance. Located less than 1/2 mile to Food City and is a short drive to downtown. Tims Ford Lake Homes will be constructing a variety of floor plans in Deer Valley along with other quality custom home builders. This floor

  Angela Privett Benchmark Realty, LLC

  0 Deer Valley Unit 3529310, 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 $797,792

  Last Listing Agent Jennifer Watson Exit Truly Home Realty

  17 Cannonball Ct, Winchester, TN 37398
• 

  

  /56

  Est $384,539

  Not Listed For Sale

  715 N Vine St, Winchester, TN 37398

  • 4 Beds
  • 3.5 Baths
  • 3,010 Sq Ft
  • Built 1948

  715 N Vine St, Winchester, TN 37398

  Last Sold Summary

  • 120 Days On Market

  Last Listing Agent Terry Christian Noble Real Estate
• 

  

  /35

  $224,900

  $5K PRICE DROP Under Contract

  • 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
• 

  

  /77

  $610,000

  Sold Jun 23, 2026

  192 Bell Dr W, Winchester, TN 37398

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

  Last Sold Summary

  • 3% Below List Price
  • $201/SF
  • 61 Days On Market

  Current Estimated Value $609,616

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

  192 Bell Dr W, Winchester, TN 37398
• 

  

  /67

  Est $1,996,446

  Not Listed For Sale

  290 Shasteen Bend Dr, Winchester, TN 37398

  • 5 Beds
  • 6 Baths
  • 6,806 Sq Ft
  • Built 1992

  290 Shasteen Bend Dr, Winchester, TN 37398

  Last Sold Summary

  • 30 Days On Market

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

  

  /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 Century 21 Volunteer Realty

  209 N Jefferson St, Winchester, TN 37398
• 

  /2

  $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 $760,879

  Last Listing Agent Felicia Wright Leading Edge Real Estate Group

  20 Windjammer Ct, Winchester, TN 37398
• 

  

  /58

  Est $528,857

  Not Listed For Sale

  271 Cedar Bluff Dr, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 3,448 Sq Ft
  • Built 1990

  271 Cedar Bluff Dr, Winchester, TN 37398

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent LeighAnn Tillett Lamica Realty
• 

  

  /47

  $530,000

  $20K PRICE DROP Under Contract

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

  379 Bell Dr W, Winchester, TN 37398

  Custom-built and designed with quality living in mind, this spacious home offers 3 bedrooms, 3.5 baths, and 3,578 sq. ft. of well-planned living space. Features include a heated and cooled sunroom, bonus room, dedicated office, spacious kitchen, detached and attached garage, with a 4-car garage capacity. The property also includes two water meters, with a separate meter for the garden and yard.

  Dawn Parrish Leading Edge Real Estate Group

  379 Bell Dr W, 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 $1,515,021

  Last Listing Agent Heather Boldizsar Lake Homes Realty, LLC

  130 Phillips Dr, Winchester, TN 37398
• 

  

  /58

  Est $774,000

  Not Listed For Sale

  6086 Lynchburg Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1973

  6086 Lynchburg Rd, Winchester, TN 37398

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Fhonda Hatmaker eXp Realty
• 

  

  /20

  $369,000

  • 2 Beds
  • 2 Baths
  • 1,615 Sq Ft

  101 Edgefield Ct, Winchester, TN 37398

  Welcome to maintenance-free living in this beautifully maintained townhome! Enjoy the convenience of low-maintenance living with exterior maintenance taken care of, giving you more time to relax and enjoy your new home. This inviting property offers comfortable living space, a functional layout, and a welcoming atmosphere. Ideally suited for those looking for the ease of townhome living without

  Angela Miller John Smith Jr Realty and Auction LLC

  101 Edgefield Ct, Winchester, TN 37398
• 

  

  /28

  $1,492,843

  Sold May 08, 2026

  1584 Liberty Rd, Winchester, TN 37398

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Fallon Massey Van Massey Realty & Auction

  1584 Liberty Rd, Winchester, TN 37398

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