Homes in ZIP Code 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 $281,707

  Last Listing Agent Connie Landers BHGRE Baker & Cole

  41 Cheyenne Ave, Winchester, TN 37398
• 

  

  

  /41

  Est $264,213

  Not Listed For Sale

  1750 Beth Page Rd, Estill Springs, TN 37330

  • 4 Beds
  • 2 Baths
  • 1,825 Sq Ft
  • Built 1959

  1750 Beth Page Rd, Estill Springs, TN 37330

  Last Sold Summary

  • 115 Days On Market
• 

  

  

  /31

  $195,000

  Pending

  • Land
  • 0 Sq Ft

  0 N Jefferson St Unit 41, Winchester, TN 37398

  Lakefront Homesite on Tims Ford Lake with Panoramic Water Views. Desirable lakefront homesite available on Tim's Ford Lake. This exceptional end lot offers breathtaking panoramic water views and direct water access along both the north and east sides of the property. With no neighboring lot to the north, you'll enjoy a secluded waterfront setting that captures stunning sunrises and year-round

  Tara Hays Benchmark Realty, LLC

  0 N Jefferson St Unit 41, 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 $304,785

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  1956 Old Estill Springs Rd, Winchester, TN 37398
• 

  

  

  /56

  Est $430,611

  Not Listed For Sale

  165 Maple Bend Ln, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,518 Sq Ft
  • Built 2005

  165 Maple Bend Ln, Winchester, TN 37398

  Last Sold Summary

  • 91 Days On Market
• 

  

  /30

  $499,900

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,645 Sq Ft

  2607 Old Tullahoma Rd, Winchester, TN 37398

  Let's talk about convenience! This home is located within a few minutes of everything you'll ever need. Winchester, TN is a charming lakeside town offering a blend of outdoor recreation, historic charm, and a historic down town. We have it all boutiques, locally owned restaurants, and a vintage theater. This spacious 3–4 bedroom home with 2 full baths and a half bath, offering primary bedroom on

  Valerie Wilder Century 21 Coffee County Realty & Auction

  2607 Old Tullahoma Rd, 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
• 

  

  /28

  Est $275,010

  Not Listed For Sale

  3960 Old Tullahoma Rd, Winchester, TN 37398

  • 5 Beds
  • 2 Baths
  • 1,685 Sq Ft
  • Built 1960

  3960 Old Tullahoma Rd, Winchester, TN 37398

  Last Sold Summary

  • 27 Days On Market
• 

  

  /19

  $250,000

  • Land
  • 37,026 Sq Ft
  • $294,118 per Acre

  0 E Rockcrest Cir Unit 42, Winchester, TN 37398

  Set within the serene Hopkins Point community of Winchester, this stunning 0.85-acre waterfront homesite offers a rare chance to create your own private retreat along the shores of Tims Ford Lake. With peaceful water views and a sense of seclusion, this property invites you to slow down and fully embrace the beauty of lake living. Perked for up to two bedrooms, this homesite is perfectly suited

  Lisa Culp Taylor Onward Real Estate

  0 E Rockcrest Cir Unit 42, 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 $415,370

  Last Listing Agent Billie Kay Caldwell Swaffords Property Shop

  1050 Franklin Heights Dr, Winchester, TN 37398
• 

  

  /30

  Est $365,350

  Not Listed For Sale

  106 Prince Place, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,942 Sq Ft
  • Built 1989

  106 Prince Place, Winchester, TN 37398

  Last Sold Summary

  • 195 Days On Market
• 

  

  /7

  $69,900

  • Land
  • 0 Sq Ft

  0 Why Worry Ln Unit 323, Winchester, TN 37398

  Incredible value-priced lot! Build your dream home in the beautiful Twin Creeks Village, one of the most desirable lakefront communities in the area. This lot is on the marina side and offers the perfect combination of modern amenities and an active, resort lifestyle. Enjoy the peace of mind and exclusivity that comes with living in this gated community. Residents have access to multiple swimming

  Stacy Zepeda The Sapphire Group Real Estate

  0 Why Worry Ln Unit 323, 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 $237,362

  Last Listing Agent Ben Absher Realty One Group Experts

  

  114 11th Ave NW, Winchester, TN 37398
• 

  

  /34

  Est $417,976

  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
• 

  

  /21

  $89,999

  • Land
  • 0 Sq Ft

  0 Suntan Ct Unit 267, Winchester, TN 37398

  Don’t miss your chance to own this extra-large corner lot in the prestigious Twin Creeks Subdivision. Conveniently located just a quick golf cart ride from Drafts and Watercrafts Marina, this property offers both comfort and lifestyle.Enjoy access to three community pools and a beautiful clubhouse, with lawn mowing included through the HOA for low-maintenance living. But what truly sets Twin

  Dawn Parrish Leading Edge Real Estate Group

  0 Suntan Ct Unit 267, 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 $368,613

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  1549 Mansford Rd, Winchester, TN 37398
• 

  

  /17

  Est $237,707

  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
• 

  

  /32

  $899,900

  New Construction

  • 3 Beds
  • 4 Baths
  • 3,258 Sq Ft

  98 Whippoorwill Cove Rd, Winchester, TN 37398

  Beautiful Lake home with no stairs to the water's edge.This 4 or 5 bedroom home has a private & permitted dock. New Construction built by Sun Valley Custom Homes. Large Kitchen open to the living room and outdoor deck. Master bedroom is on it's own privatefloor with large windows overlooking the lake. Upstairs are 3 more bedrooms and spacious Bonus room. Take the spiral staircasefrom the

  Whitney Jones Benchmark Realty, LLC

  98 Whippoorwill Cove Rd, 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
• 

  

  /44

  Est $994,067

  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
• 

  

  /73

  $689,900

  • 4 Beds
  • 3.5 Baths
  • 3,705 Sq Ft

  356 Ridgecrest Dr, Winchester, TN 37398

  Step into this magnificent 3,705 square foot home, an absolute gem in the highly sought-after Franklin Hills Subdivision. Designed for both grand entertaining and comfortable family living, this residence offers 4 bedrooms and 3.5 baths across two levels.You will immediately notice the architectural elegance, highlighted by premier trim work and stunning tray ceilings. The entryway is graced

  Sean Crabtree Blue Door Realty Group

  356 Ridgecrest Dr, 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 $449,272

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

  300 Old Clark Rd, Winchester, TN 37398
• 

  

  /19

  Est $329,056

  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
• 

  

  /34

  $689,900

  New Construction $10K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,150 Sq Ft

  142 Barefoot Way, Winchester, TN 37398

  Lake season is here, so what better way to enjoy it than to settle into your new lake home! This brand new home features a beautiful open layout. Downstairs offers a spacious open living room with an eat in kitchen that is equipped with all Fridgidaire Gallery series appliances along with a dining area off to the side. Off the livingroom the sliding doors open up to a screened in porch and an

  Gary Aadnes 1st Choice REALTOR

  142 Barefoot Way, Winchester, TN 37398
• 

  

  /28

  $165,000

  Sold Jul 07, 2025

  0 N Jefferson St Unit RTC2781941, Winchester, TN 37398

  • Land
  • 0 Sq Ft

  Last Sold Summary

  • 6% Below List Price
  • 128 Days On Market

  Last Listing Agent Tara Hays Benchmark Realty, LLC

  0 N Jefferson St Unit RTC2781941, Winchester, TN 37398
• 

  

  /20

  Est $257,137

  Not Listed For Sale

  808 Pleasant View Dr, Winchester, TN 37398

  • 3 Beds
  • 1.5 Baths
  • 1,472 Sq Ft
  • Built 1958

  808 Pleasant View Dr, Winchester, TN 37398

  Last Sold Summary

  • 1 Day On Market
• 

  

  /41

  $759,999

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

  112 Rogers Ave, Winchester, TN 37398

  Looking for a lake home that feels private, peaceful, and still close to everything? Welcome to 112 Rogers Ave, a newly constructed waterfront retreat inside the city limits of Winchester. Known as the “cottage on the lake,” this rare property offers direct water access, a natural path to the shoreline, and a quiet setting surrounded by nature. Set in the established Rogers Haven neighborhood,

  Chad Jeffers Compass RE

  112 Rogers Ave, Winchester, TN 37398
• 

  

  /57

  $815,000

  Sold Dec 05, 2025

  226 Kayak Way, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 2,219 Sq Ft
  • Built 2021

  Last Sold Summary

  • 2% Below List Price
  • $367/SF

  Current Estimated Value $835,375

  Last Listing Agent Dennis Sanders eXp Realty

  226 Kayak Way, Winchester, TN 37398
• 

  

  /27

  Est $326,841

  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
• 

  

  /27

  $274,999

  $25K PRICE DROP Under Contract

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

  213 S Porter St, Winchester, TN 37398

  Turnkey townhome investment opportunity with immediate income. This unit offers 3 bedrooms, 2.5 bathrooms, and approximately 1,575 sq ft, featuring an open-concept layout, modern finishes, and a fully fenced backyard. The unit is tenant occupied, providing stable cash flow from day one. Units 211, 213, and 215 are leased at $1,745/month; Unit 217 is leased at $1,895/month. Property is located in

  Grey Smotherman Reliant Realty ERA Powered

  213 S Porter St, Winchester, TN 37398
• 

  

  /16

  $130,000

  Sold Aug 14, 2025

  0 River Watch Way Unit RTC2941024, Winchester, TN 37398

  • Land
  • 16,552 Sq Ft
  • $342,105 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 6 Days On Market

  Last Listing Agent Jason Hilbelink Onward Real Estate

  0 River Watch Way Unit RTC2941024, Winchester, TN 37398
• 

  

  /34

  Est $574,146

  Not Listed For Sale

  55 Brown Rd E, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,735 Sq Ft
  • Built 1976

  55 Brown Rd E, Winchester, TN 37398

  Last Sold Summary

  • 132 Days On Market
• 

  

  /81

  $799,900

  $30K PRICE DROP Under Contract

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

  17 Cannonball Ct, Winchester, TN 37398

  Better than new! Welcome to 17 Cannonball Court—where timeless design meets effortless lakeside living in the prestigious, gated community of Twin Creeks Village on Tim's Ford Lake. This elegantly appointed 4-bedroom, 3.5-bath residence offers almost 3000k sq. ft. of thoughtfully designed living space with too many upgrades to list here. (See media for upgrades list.) From the moment you enter,

  Jennifer Watson Exit Truly Home Realty

  17 Cannonball Ct, Winchester, TN 37398
• 

  

  /30

  $210,000

  Sold Jun 03, 2026

  110 Dotson Ln, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • Built 1945

  Last Sold Summary

  • 7% Below List Price
  • $152/SF
  • 47 Days On Market

  Current Estimated Value $216,450

  Last Listing Agent Pamela Hamilton RE/MAX Unlimited

  110 Dotson Ln, Winchester, TN 37398
• 

  

  /42

  Est $542,440

  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
• 

  

  /9

  $1,800,000

  • Land
  • 25.15 Acres
  • $71,571 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
• 

  

  /55

  $281,000

  Sold Jan 28, 2026

  218 Susie Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,446 Sq Ft
  • Built 1996

  Last Sold Summary

  • 8% Below List Price
  • $194/SF
  • 189 Days On Market

  Current Estimated Value $292,616

  Last Listing Agent Sean Crabtree Blue Door Realty Group

  218 Susie Dr, Winchester, TN 37398
• 

  

  /38

  Est $369,537

  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
• 

  

  /77

  $629,000

  Under Contract

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

  192 Bell Dr W, Winchester, TN 37398

  Take a look at this beautifully maintained 19-year-old home! This property offers a variety of desirable features, including elegant trey ceilings, a well water system, and a sprinkler system to keep the yard looking its best. The roof was replaced in 2020, and a brand-new hot water heater was installed just last year, providing added peace of mind. Don’t miss your chance to see all this home has

  Bj Rigsby Lynch Rigsby Realty & Auction, LLC

  192 Bell Dr W, Winchester, TN 37398
• 

  

  /6

  $125,000

  Sold Jan 06, 2026

  3250 Lynchburg Rd, Winchester, TN 37398

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft
  • Built 1992

  Last Sold Summary

  • 17% Below List Price
  • $128/SF
  • 113 Days On Market

  Last Listing Agent Aleisha Putman Synergy Realty Network, LLC

  3250 Lynchburg Rd, Winchester, TN 37398

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