Winchester, TN Homes

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  /49

  $305,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft

  367 Carol Cir, Winchester, TN 37398

  Welcome home to this move-in ready 3-bedroom, 2-bath home perfectly situated on a corner lot in a quiet Winchester neighborhood—located outside the city limits and just minutes from Tims Ford Lake and Twin Creeks Marina. Built in 2003, this 1,420 sq. ft. home offers a comfortable, functional layout with an attached two-car garage and thoughtful updates throughout. Inside, you’ll find welcoming

  Paige Morris Southern Middle Realty

  367 Carol Cir, Winchester, TN 37398
• 

  

  

  /53

  $795,000

  Sold Nov 04, 2025

  190 Cascade Dr, Winchester, TN 37398

  • 4 Beds
  • 3.5 Baths
  • 3,515 Sq Ft
  • Built 2009

  Last Sold Summary

  • 10% Below List Price
  • $226/SF
  • 200 Days On Market

  Current Estimated Value $785,340

  Last Listing Agent Rachel Ferrell Southern Middle Realty

  190 Cascade Dr, Winchester, TN 37398
• 

  

  

  /20

  Est $172,135

  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

  • 3% Below List Price
  • $204/SF
  • 43 Days On Market

  • Last Sold Price $177,000
  • Jul 30, 2024

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

  

  /2

  $95,000

  • Land
  • 5.34 Acres
  • $17,790 per Acre

  0 Haddon Ln Unit RTC3190742, Winchester, TN 37398

  5.34 acres on the desirable Broadview side of Winchester! This beautiful tract is ready to go with a perk site already established—bring your plans and start building. Enjoy the perfect blend of privacy and convenience, located less than 10 minutes from Devil Step boat ramp and Tims Ford Lake. Whether you're looking for a homesite or weekend getaway, this one checks all the boxes! More pictures

  Nathan Smith John Smith Jr Realty and Auction LLC

  0 Haddon Ln Unit RTC3190742, Winchester, TN 37398
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  /37

  $175,000

  Sold May 28, 2025

  802 Old Cowan Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2004

  Last Sold Summary

  • 9% Above List Price
  • $125/SF
  • 3 Days On Market

  Last Listing Agent Kisha Sanders Elam Real Estate

  802 Old Cowan Rd, Winchester, TN 37398
• 

  

  /42

  Est $1,171,761

  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

  • 7% Above List Price
  • $397/SF
  • 0 Days On Market

  • Last Sold Price $1,100,000
  • Apr 08, 2024

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

  

  /18

  $509,450

  • Land
  • 22.15 Acres
  • $23,000 per Acre

  0 Haddon Ln Unit RTC2946006, Winchester, TN 37398

  TAX ID has not been split off from the original 50 +/- parcel. This parcel has been survey and will be recorded when sold. There is a well on property, and property has been surveyed into tracts/perked. RARE-FIND! Minutes to Tims Ford Lake. Seller selling as a whole, and SOLD AS IS.

  Teresa Miller Century 21 Coffee County Realty & Auction

  0 Haddon Ln Unit RTC2946006, Winchester, TN 37398
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  /35

  $235,000

  Sold Jan 12, 2026

  136 Bel Aire Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1964

  Last Sold Summary

  • 18% Below List Price
  • $121/SF
  • 187 Days On Market

  Current Estimated Value $241,885

  Last Listing Agent Sharon Swafford Swaffords Property Shop

  136 Bel Aire Dr, Winchester, TN 37398
• 

  

  /21

  Est $347,480

  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

  • 9% Above List Price
  • $181/SF
  • 38 Days On Market

  • Last Sold Price $320,000
  • Mar 27, 2024

  Last Listing Agent Josh Cook Benchmark Realty, LLC
• 

  

  /5

  $99,900

  $25K PRICE DROP

  • Land
  • 39,204 Sq Ft
  • $111,000 per Acre

  0 Owl Hollow Ln Unit Lot 1, Winchester, TN 37398

  This lot is just waiting on a lake lover to build their get-a-way retreat. The .90 acre lot has been septic approved for a 3 bedroom home. An adjacent neighbor includes acres of TWRA wildlife protected property in a quiet lake cove, perfect for launching kayaks and canoes. Just minutes away from several boat ramps, Tim's Ford State Park, Bear Trace Golf Course at Tim's Ford, Twin Creeks Marina,

  Jaine Colley WEICHERT, REALTORS Joe Orr & Associates

  0 Owl Hollow Ln Unit Lot 1, Winchester, TN 37398
• 

  

  /34

  $270,000

  Sold Dec 03, 2025

  805 S Shephard St, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,310 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Below List Price
  • $206/SF
  • 99 Days On Market

  Last Listing Agent Pelatiah Prince Winton Auction & Realty Co.

  805 S Shephard St, Winchester, TN 37398
• 

  

  /14

  Est $237,125

  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

  • 53% Below List Price
  • $149/SF
  • 183 Days On Market

  • Last Sold Price $500,000
  • Apr 18, 2025

  Last Listing Agent Daniel Garner Keller Williams Realty - Murfreesboro
• 

  

  /16

  $429,900

  New Construction Pending

  • 4 Beds
  • 2 Baths
  • 2,089 Sq Ft

  106 Wiseman Ln, Winchester, TN 37398

  Discover this beautiful home featuring custom-built cabinets, granite countertops, spacious walk-in closets, a welcoming covered front porch, and a back deck perfect for relaxing or entertaining. Sitting on 1.2 acres, the property boasts a huge, flat, and cleared backyard—ideal for kids, pets, and outdoor activities. Located in a peaceful and desirable new neighborhood, this home offers

  Andrew Curl Better Homes & Gardens Real Estate Heritage Group

  106 Wiseman Ln, Winchester, TN 37398
• 

  

  /49

  $220,000

  Sold Dec 12, 2025

  190 Cheyenne Ave, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,118 Sq Ft
  • Built 1998

  Last Sold Summary

  • 4% Below List Price
  • $197/SF
  • 22 Days On Market

  Current Estimated Value $220,899

  Last Listing Agent Rachel Ferrell Southern Middle Realty

  190 Cheyenne Ave, Winchester, TN 37398
• 

  

  /27

  Est $291,563

  Not Listed For Sale

  122 Highland Dr, Winchester, TN 37398

  • 3 Beds
  • 1.5 Baths
  • 1,689 Sq Ft
  • Built 1955

  122 Highland Dr, Winchester, TN 37398

  Last Sold Summary

  • 3% Below List Price
  • $178/SF
  • 2 Days On Market

  • Last Sold Price $300,000
  • Jan 05, 2024

  Last Listing Agent Candice Bedwell Epique Realty
• 

  

  /17

  $114,900

  $20K PRICE DROP

  • Land
  • 2.46 Acres
  • $46,764 per Acre

  0 Lakeview Way Unit 51, Winchester, TN 37398

  Come build your dream home on this +/- 2.457 acre lot in the desirable Holly Hill Subdivision! Ideally located within walking distance to Winchester City Park and walking trail, this lot is also just down the road from a public boat launch on the beautiful Tims Ford Lake. Enjoy the convenience of being less than five minutes from all the shopping, dining, and amenities that Winchester and Decherd

  Pelatiah Prince Winton Auction & Realty Co.

  0 Lakeview Way Unit 51, Winchester, TN 37398
• 

  

  /3

  $40,000

  Sold Jun 20, 2025

  0 Old Tullahoma Rd Unit RTC2775157, Winchester, TN 37398

  • Land
  • 27,442 Sq Ft
  • $63,492 per Acre

  Last Sold Summary

  • 38% Below List Price
  • 142 Days On Market

  Last Listing Agent Tony Griffis Better Homes & Gardens Real Estate Heritage Group

  0 Old Tullahoma Rd Unit RTC2775157, Winchester, TN 37398
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  /68

  Est $1,103,479

  Not Listed For Sale

  702 Bluff Dr, Winchester, TN 37398

  • 4 Beds
  • 3.5 Baths
  • 2,884 Sq Ft
  • Built 1994

  702 Bluff Dr, Winchester, TN 37398

  Last Sold Summary

  • 1% Below List Price
  • $385/SF
  • 1 Day On Market

  • Last Sold Price $1,110,000
  • Nov 08, 2024

  Last Listing Agent Alison Davis Pilkerton Realtors
• 

  

  /23

  $149,000

  • Land
  • 14,374 Sq Ft
  • $451,515 per Acre

  0 Hammock Dr Unit 241, Winchester, TN 37398

  Large corner lot in Twin Creeks! This beautiful lot sits on the marina side of the neighborhood, placing you within easy walking distance to the full-service marina, boat slips, a lakefront restaurant/bar, three resort-style pools, clubhouse, scenic walking trails, and a sandy beach area. Its corner location offers excellent building flexibility and open sight lines. With only a single-story home

  Heather Boldizsar Lake Homes Realty, LLC

  0 Hammock Dr Unit 241, Winchester, TN 37398
• 

  

  /45

  $764,900

  Sold Jun 23, 2025

  467 Wildwood Trace, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 1,998 Sq Ft
  • Built 2019

  Last Sold Summary

  • $383/SF
  • 3 Days On Market

  Current Estimated Value $773,114

  Last Listing Agent Donna Mason Botsko Properties, Inc.

  467 Wildwood Trace, Winchester, TN 37398
• 

  

  /27

  Est $140,038

  Not Listed For Sale

  408 7th Ave NW, Winchester, TN 37398

  • 2 Beds
  • 1 Bath
  • 926 Sq Ft
  • Built 1953

  408 7th Ave NW, Winchester, TN 37398

  Last Sold Summary

  • 5% Above List Price
  • $144/SF
  • 114 Days On Market

  • Last Sold Price $133,600
  • Oct 26, 2024

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

  

  /28

  $239,000

  $16K PRICE DROP

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

  525 Sharp Springs Rd, Winchester, TN 37398

  Charming and efficiently designed home offering incredible value with generous square footage! This well-maintained property features 2 spacious bedrooms upstairs along with a full bath, plus an additional full bath on the main level for added convenience. The open-concept layout connects the great room, dining area, and a large, updated kitchen—perfect for everyday living and entertaining. Enjoy

  Stephanie Dowdy Freedom Realty Group

  525 Sharp Springs Rd, Winchester, TN 37398
• 

  

  /52

  $429,900

  Sold Jun 20, 2025

  8343 Lynchburg Rd, Winchester, TN 37398

  • 4 Beds
  • 2 Baths
  • 2,297 Sq Ft
  • Built 2024

  Last Sold Summary

  • 7% Below List Price
  • $187/SF
  • 181 Days On Market

  Last Listing Agent Lisa Curl Better Homes & Gardens Real Estate Heritage Group

  8343 Lynchburg Rd, Winchester, TN 37398
• 

  

  /57

  Est $2,264,363

  Not Listed For Sale

  1640 Cline Ridge Rd, Winchester, TN 37398

  • 3 Beds
  • 3 Baths
  • 4,100 Sq Ft
  • Built 2005

  1640 Cline Ridge Rd, Winchester, TN 37398

  Last Sold Summary

  • 21% Below List Price
  • $695/SF
  • 6 Days On Market

  • Last Sold Price $2,850,000
  • May 15, 2023

  Last Listing Agent Tim King French King Fine Properties
• 

  

  /13

  $139,900

  • Land
  • 40,075 Sq Ft
  • $152,065 per Acre

  0 Sharp Springs Rd Unit RTC3134214, Winchester, TN 37398

  Commercial C-2 zoned lot! Location! Location! Location!! Just under an acre (0.92 +/- Acres) a half mile from Walmart Shopping Center, convenient also to city park, eateries, downtown Winchester, Decherd and Tims Ford Lake High Traffic Area Build your new business here!

  Debra (L.D.) Thompson Swaffords Property Shop

  0 Sharp Springs Rd Unit RTC3134214, Winchester, TN 37398
• 

  

  /47

  $485,000

  Sold Nov 24, 2025

  105 Twilight Dr, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 3,570 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $136/SF
  • 20 Days On Market

  Current Estimated Value $520,380

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

  105 Twilight Dr, Winchester, TN 37398
• 

  

  /22

  Est $336,675

  Not Listed For Sale

  102 10th Ave NW, Winchester, TN 37398

  • 4 Beds
  • 3 Baths
  • 3,150 Sq Ft
  • Built 2001

  102 10th Ave NW, Winchester, TN 37398

  Last Sold Summary

  • 1% Above List Price
  • $106/SF
  • 32 Days On Market

  • Last Sold Price $333,000
  • Sep 25, 2024

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

  

  /13

  $114,900

  $5K PRICE DROP

  • Land
  • 1.16 Acres
  • $98,796 per Acre

  0 Lakeview Way Unit 52, Winchester, TN 37398

  Come build your dream home on this +/- 1.163 acre lot in the desirable Holly Hill Subdivision! Ideally located within walking distance to Winchester City Park and walking trail, this lot is also just down the road from a public boat launch on the beautiful Tims Ford Lake. Enjoy the convenience of being less than five minutes from all the shopping, dining, and amenities that Winchester and Decherd

  Pelatiah Prince Winton Auction & Realty Co.

  0 Lakeview Way Unit 52, Winchester, TN 37398
• 

  

  /30

  $478,000

  Sold Jan 16, 2026

  159 Canoe Ct, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 2,232 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $214/SF
  • 68 Days On Market

  Last Listing Agent Grey Smotherman Reliant Realty ERA Powered

  159 Canoe Ct, Winchester, TN 37398
• 

  

  /38

  Est $325,821

  Not Listed For Sale

  810 Cumberland Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 2,260 Sq Ft
  • Built 1948

  810 Cumberland Dr, Winchester, TN 37398

  Last Sold Summary

  • $144/SF
  • 72 Days On Market

  • Last Sold Price $325,000
  • Feb 18, 2025

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

  

  /27

  $274,999

  $25K PRICE DROP Under Contract

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

  217 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

  217 S Porter St, Winchester, TN 37398
• 

  

  /4

  $741,300

  Sold Nov 19, 2025

  0 Old Tullahoma Rd Unit RTC3048163, Winchester, TN 37398

  Last Sold Summary

  Last Listing Agent Shawna Denby 1st Choice REALTOR

  0 Old Tullahoma Rd Unit RTC3048163, Winchester, TN 37398
• 

  

  /37

  Est $680,783

  Not Listed For Sale

  2233 Georgia Crossing Rd, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,765 Sq Ft
  • Built 2004

  2233 Georgia Crossing Rd, Winchester, TN 37398

  Last Sold Summary

  • 6% Below List Price
  • $262/SF
  • 115 Days On Market

  • Last Sold Price $724,000
  • Mar 07, 2025

  Last Listing Agent Landon Keller Century 21 Volunteer Realty
• 

  

  /6

  $79,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,139 Sq Ft

  503 Elm St, Winchester, TN 37398

  2 story home, Fenced back yard, Screened in front porch. Separate garage. Property being sold as-is.

  Brent Liston Sr. Lynch Rigsby Realty & Auction, LLC

  503 Elm St, Winchester, TN 37398
• 

  

  /39

  $250,000

  Sold Apr 02, 2026

  301 N Shephard St, Winchester, TN 37398

  • 2 Beds
  • 2 Baths
  • 1,313 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Below List Price
  • $190/SF
  • 22 Days On Market

  Current Estimated Value $258,088

  Last Listing Agent Timothy Collins SimpliHOM

  301 N Shephard St, Winchester, TN 37398
• 

  

  /23

  Est $249,835

  Not Listed For Sale

  414 S Vine St, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft
  • Built 2024

  414 S Vine St, Winchester, TN 37398

  Last Sold Summary

  • 4% Above List Price
  • $183/SF
  • 39 Days On Market

  • Last Sold Price $240,000
  • Dec 10, 2024

  Last Listing Agent Christopher (Bra Heath Simmons Realty
• 

  

  /70

  $649,000

  $40K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,592 Sq Ft

  65 Pontoon Place, Winchester, TN 37398

  Discover refined lake living in this exquisite, gated community, where peace and luxury come together. Selling Fully Furnished!! Residents here enjoy an impressive list of amenities, including a full-service marina, clubhouse, and several pools. Low maintenance with a HOA that takes care of your lawn and all amenities. This stunning home is crafted with timeless detail featuring both an indoor

  Angela Miller John Smith Jr Realty and Auction LLC

  65 Pontoon Place, Winchester, TN 37398
• 

  

  /37

  $400,000

  Sold Jun 13, 2025

  8377 Lynchburg Rd, Winchester, TN 37398

  • 4 Beds
  • 2 Baths
  • 2,101 Sq Ft
  • Built 2024

  Last Sold Summary

  • 6% Below List Price
  • $190/SF
  • 171 Days On Market

  Last Listing Agent Lisa Curl Better Homes & Gardens Real Estate Heritage Group

  8377 Lynchburg Rd, Winchester, TN 37398
• 

  

  /21

  Est $236,332

  Not Listed For Sale

  601 Sharp Springs Rd, Winchester, TN 37398

  • 2 Beds
  • 1 Bath
  • 1,618 Sq Ft
  • Built 1946

  601 Sharp Springs Rd, Winchester, TN 37398

  Last Sold Summary

  • 10% Above List Price
  • $133/SF
  • 84 Days On Market

  • Last Sold Price $215,000
  • Nov 27, 2024

  Last Listing Agent Brent Liston Sr. Lynch Rigsby Realty & Auction, LLC
• 

  

  /98

  $649,000

  $51K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,224 Sq Ft

  154 Barefoot Way, Winchester, TN 37398

  The best value in Barefoot Bay, offering more space, more flexibility, & fully furnished. With 4 bedrooms (sleeps 12) & sold turnkey, this home stands apart from anything else currently available, giving buyers more sleeping capacity, immediate usability, & long-term versatility whether for personal use, second home, or short-term rental. Seller will pay TWO years of HOA dues w/ an acceptable

  Julianne Richard Compass Tennessee, LLC

  154 Barefoot Way, Winchester, TN 37398

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