Homes in ZIP Code 37398

• 

  

  

  /46

  $114,900

  $45K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 1,444 Sq Ft

  7334 Lynchburg Rd, Winchester, TN 37398

  Opportunity near Tims Ford Lake! This 1954-built home offers 3 bedrooms, 2.5 baths, 1,444 sq ft of living space, and 1.24 mostly level acres with mature trees and plenty of usable outdoor space. Additional features include a 2-car carport, screened porch, above-ground pool, and approximately 1,300 sq ft unfinished walk-out basement per tax records.This property is a true fixer-upper and

  Jordan Mitchell SimpliHOM

  7334 Lynchburg Rd, Winchester, TN 37398
• 

  

  

  /33

  $245,000

  Sold May 15, 2026

  119 Kenmore Ave, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • Built 2025

  Last Sold Summary

  • $192/SF
  • 22 Days On Market

  Current Estimated Value $208,521

  Last Listing Agent Andrea Cruz John Smith Jr Realty and Auction LLC

  119 Kenmore Ave, Winchester, TN 37398
• 

  

  

  /67

  Est $1,851,195

  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.
• 

  

  

  /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
• 

  

  

  /54

  $300,000

  Sold Oct 16, 2025

  285 Crimson Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,761 Sq Ft
  • Built 2001

  Last Sold Summary

  • 13% Below List Price
  • $170/SF
  • 92 Days On Market

  Current Estimated Value $328,366

  Last Listing Agent Kristin Swan-White Reliant Realty ERA Powered

  285 Crimson Dr, Winchester, TN 37398
• 

  

  /58

  Est $484,500

  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
• 

  

  /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
• 

  

  /60

  $875,000

  Sold May 01, 2026

  1000 N Vine St, Winchester, TN 37398

  • 4 Beds
  • 2 Baths
  • 2,164 Sq Ft
  • Built 1925

  Last Sold Summary

  • 30% Below List Price
  • $404/SF
  • 27 Days On Market

  Current Estimated Value $857,851

  Last Listing Agent Melissa Stewart Swaffords Property Shop

  1000 N Vine St, Winchester, TN 37398
• 

  

  /58

  Est $713,000

  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
• 

  /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
• 

  

  /23

  $326,500

  Sold Apr 20, 2026

  170 Brandi Cir, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,663 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Below List Price
  • $196/SF
  • 25 Days On Market

  Current Estimated Value $337,809

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

  170 Brandi Cir, Winchester, TN 37398
• 

  

  /20

  Est $228,955

  Not Listed For Sale

  112 Cheyenne Ave, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1998

  112 Cheyenne Ave, Winchester, TN 37398

  Last Sold Summary

  • 4 Days On Market

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

  

  /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
• 

  

  /14

  $64,999

  Sold Aug 10, 2026

  0 Lookout Dr Unit 43, Winchester, TN 37398

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

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Alexia Cain Home and Farms Inc

  0 Lookout Dr Unit 43, Winchester, TN 37398
• 

  

  /32

  Est $276,831

  Not Listed For Sale

  766 Maple Bend Rd, Winchester, TN 37398

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft
  • Built 1994

  766 Maple Bend Rd, Winchester, TN 37398

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Melissa Stewart Swaffords Property Shop
• 

  /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
• 

  

  /5

  $27,500

  Sold Feb 26, 2026

  0 Lynchburg Rd Unit 6, Winchester, TN 37398

  • Land
  • 34,412 Sq Ft
  • $34,810 per Acre

  Last Sold Summary

  • 39% Below List Price
  • 256 Days On Market

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  0 Lynchburg Rd Unit 6, Winchester, TN 37398
• 

  

  /22

  Est $218,850

  Not Listed For Sale

  37 Lindbergh Ave, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1994

  37 Lindbergh Ave, Winchester, TN 37398

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Maria Checchin AXEN Realty, LLC
• 

  

  /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
• 

  

  /17

  $58,200

  Sold Mar 03, 2026

  0 Union Rd Unit 12, Winchester, TN 37398

  • Land
  • 30,927 Sq Ft
  • $81,972 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 175 Days On Market

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  0 Union Rd Unit 12, Winchester, TN 37398
• 

  

  /45

  Est $326,452

  Not Listed For Sale

  1132 Holders Cove Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,667 Sq Ft
  • Built 2000

  1132 Holders Cove Rd, Winchester, TN 37398

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Sharon Swafford Swaffords Property Shop
• 

  

  /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
• 

  

  /28

  $167,000

  Sold Oct 02, 2025

  500 S Jefferson St, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,499 Sq Ft
  • Built 1965

  Last Sold Summary

  • 12% Below List Price
  • $111/SF
  • 12 Days On Market

  Current Estimated Value $183,243

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

  500 S Jefferson St, Winchester, TN 37398
• 

  

  /32

  Est $193,543

  Not Listed For Sale

  408 6th Ave NW, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1950

  408 6th Ave NW, Winchester, TN 37398

  Last Sold Summary

  • 337 Days On Market

  Last Listing Agent Yvonne Stewart Winton Auction & Realty Co.
• 

  

  /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
• 

  

  /18

  $210,000

  Sold Apr 10, 2026

  119 Highland Dr, Winchester, TN 37398

  • 3 Beds
  • 1 Bath
  • 1,433 Sq Ft
  • Built 1949

  Last Sold Summary

  • 18% Below List Price
  • $147/SF
  • 35 Days On Market

  Current Estimated Value $217,090

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

  119 Highland Dr, Winchester, TN 37398
• 

  

  /55

  Est $1,346,176

  Not Listed For Sale

  668 Bluff Dr, Winchester, TN 37398

  • 2 Beds
  • 2.5 Baths
  • 3,076 Sq Ft
  • Built 1994

  668 Bluff Dr, Winchester, TN 37398

  Last Sold Summary

  • 78 Days On Market

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

  

  /16

  $296,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  383 Strawberry Dr, Winchester, TN 37398

  Move In Ready!!! This cozy 3 bed 2 bath home is nestled on one of the largest lots in the neighborhood. Inside boasts a split floorplan with the owner's suite on one end while the additional beds and bath are on the opposite side. Plenty of natural light throughout, Stainless steel appliances with washer and dryer included. New laminate flooring throughout. Large separate laundry room located

  Josh Hammonds Craig and Wheeler Realty & Auction

  383 Strawberry Dr, Winchester, TN 37398
• 

  

  /49

  $334,000

  Sold Apr 23, 2026

  362 Chase Cir, Winchester, TN 37398

  • 2 Beds
  • 2 Baths
  • 1,701 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Below List Price
  • $196/SF
  • 290 Days On Market

  Current Estimated Value $345,857

  Last Listing Agent John Peck Century 21 Volunteer Realty

  362 Chase Cir, Winchester, TN 37398
• 

  

  /31

  Est $183,442

  Not Listed For Sale

  106 7th Ave SW, Winchester, TN 37398

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft
  • Built 1988

  106 7th Ave SW, Winchester, TN 37398

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Victoria Hinson The Realty Association
• 

  

  /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
• 

  

  /5

  $295,000

  Sold Sep 29, 2025

  804 N Jefferson St, Winchester, TN 37398

  • Land
  • 27,442 Sq Ft
  • $468,254 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 3 Days On Market

  Current Estimated Value $294,302

  Last Listing Agent Peter Noble Crye-Leike Realty

  804 N Jefferson St, Winchester, TN 37398
• 

  

  /43

  Est $1,297,252

  Not Listed For Sale

  18 Brown Rd E, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,512 Sq Ft
  • Built 1973

  18 Brown Rd E, Winchester, TN 37398

  Last Sold Summary

  • 4 Days On Market

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

  

  /61

  $299,900

  $30K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,798 Sq Ft

  30 W Paradise Dr, Winchester, TN 37398

  Nice 3BR, 2BA home on a double corner lot in Pine Bluff Subdivision! Features include a stone fireplace, large utility room, primary bedroom with walk-in closet, screened back patio, mature shade trees, and carport with workshop. Enjoy access to Pine Bluff's private boat launch and boat storage with convenient access to Tims Ford Lake. Great location between Winchester and Tullahoma!

  W. M. Anderton Winton Auction & Realty Co.

  30 W Paradise Dr, Winchester, TN 37398
• 

  

  /36

  $565,000

  Sold Feb 13, 2026

  346 Campfire Ct, Winchester, TN 37398

  • 4 Beds
  • 3 Baths
  • 2,265 Sq Ft
  • Built 2021

  Last Sold Summary

  • 1% Below List Price
  • $249/SF
  • 199 Days On Market

  Current Estimated Value $587,172

  Last Listing Agent Kimberly Henderson Compass

  346 Campfire Ct, Winchester, TN 37398
• 

  

  /20

  Est $197,350

  Not Listed For Sale

  715 N High St, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1950

  715 N High St, Winchester, TN 37398

  Last Sold Summary

  • 32 Days On Market

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

  

  /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
• 

  

  /34

  $284,800

  Sold Feb 27, 2026

  14 Hazelwood Ln, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft
  • Built 2003

  Last Sold Summary

  • 5% Below List Price
  • $184/SF
  • 64 Days On Market

  Current Estimated Value $290,187

  Last Listing Agent Bernie Gallerani Bernie Gallerani Real Estate

  14 Hazelwood Ln, Winchester, TN 37398
• 

  

  /30

  Est $279,510

  Not Listed For Sale

  106 Hillcrest Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft
  • Built 1957

  106 Hillcrest Dr, Winchester, TN 37398

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Lauren Bailey Swaffords Property Shop
• 

  

  /4

  $49,500

  Pending

  • Land
  • 14,374 Sq Ft
  • $150,000 per Acre

  0 Sherry St, Winchester, TN 37398

  Location and already has city utilities. Just blocks off the main Lynchburg Rd for a great building site that backs up to an empty parcel and trees to the right. This lot is also walking distance to the public Dry Creek Beach. If you are in the mood for a dinner on the lake...Twin Creeks Drafts and Watercrafts is right past the public beach.Feel free to drive by of call with any questions.The

  Donna Barber Synergy Realty Network, LLC

  0 Sherry St, Winchester, TN 37398

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