Recently Sold Homes in 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 $227,546

Last Listing Agent Rachel Ferrell Southern Middle Realty

190 Cheyenne Ave, Winchester, TN 37398
/41
$349,900

Sold Jul 20, 2026

2425 Old Tullahoma Rd, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 1,567 Sq Ft
- Built 2018
Last Sold Summary
- $223/SF
- 6 Days On Market
Current Estimated Value $348,746

Last Listing Agent Greg Sitz Parks Auction & Realty

2425 Old Tullahoma Rd, Winchester, TN 37398
/36
$585,000

Sold Aug 11, 2026

124 Barefoot Way, Winchester, TN 37398
- 3 Beds
- 2.5 Baths
- 1,848 Sq Ft
- Built 2022
Last Sold Summary
- 13% Below List Price
- $317/SF
- 127 Days On Market
Current Estimated Value $572,200

Last Listing Agent Marla Richardson Parks Compass

124 Barefoot Way, 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 $515,009

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

105 Twilight Dr, 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 Earin Smotherman Reliant Realty ERA Powered

159 Canoe Ct, 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
/7
$94,000

Sold Jun 24, 2026

0 Golf Shores Dr Unit RTC3208495, Winchester, TN 37398
- Land
- 0 Sq Ft
Last Sold Summary
- 5% Below List Price
- 3 Days On Market
Last Listing Agent Chris Hawkersmith Lynch Rigsby Realty & Auction, LLC

0 Golf Shores Dr Unit RTC3208495, Winchester, TN 37398
/63
$515,000

Sold Jul 17, 2026

249 Lookout Dr, Winchester, TN 37398
- 3 Beds
- 2.5 Baths
- 2,973 Sq Ft
- Built 2025
Last Sold Summary
- 10% Below List Price
- $173/SF
- 295 Days On Market
Last Listing Agent Charlie Gonzales Southern Middle Realty

249 Lookout Dr, 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 $254,556

Last Listing Agent Timothy Collins SimpliHOM

301 N Shephard St, Winchester, TN 37398
/39
$1,225,000

Sold Sep 11, 2026

90 Wildwood Ct, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 2,184 Sq Ft
- Built 1999
Last Sold Summary
- 4% Below List Price
- $561/SF
- 18 Days On Market
Current Estimated Value $1,254,882

Last Listing Agent Marla Richardson Parks Compass

90 Wildwood Ct, Winchester, TN 37398
/42
$315,000

Sold Oct 30, 2025

2425 Old Tullahoma Rd, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 1,567 Sq Ft
- Built 2018
Last Sold Summary
- 21% Below List Price
- $201/SF
- 104 Days On Market
Current Estimated Value $348,746

Last Listing Agent Breean Hewitt Compass

2425 Old Tullahoma Rd, Winchester, TN 37398
/80
$1,450,000

Sold Jul 01, 2026

1305 Dripping Springs Rd, Winchester, TN 37398
- 3 Beds
- 4.5 Baths
- 4,497 Sq Ft
- Built 1975
Last Sold Summary
- 2% Below List Price
- $322/SF
- 7 Days On Market
Current Estimated Value $1,429,061

Last Listing Agent Thomas Ore Winton Auction & Realty Co.

1305 Dripping Springs Rd, Winchester, TN 37398
/2
$247,000

Sold Jul 15, 2026

0 Kayak Way Unit 482, Winchester, TN 37398
- Land
- 11,761 Sq Ft
- $914,815 per Acre
Last Sold Summary
- 8% Below List Price
- 3 Days On Market
Last Listing Agent Felicia Wright Leading Edge Real Estate Group

0 Kayak Way Unit 482, Winchester, TN 37398
/75
$1,960,000

Sold Jan 27, 2026

97 Shady Cove Ln, Winchester, TN 37398
- 2 Beds
- 3.5 Baths
- 3,410 Sq Ft
- Built 1997
Last Sold Summary
- 7% Below List Price
- $575/SF
- 152 Days On Market
Current Estimated Value $1,955,643

Last Listing Agent Timothy Crabtree Benchmark Realty, LLC

97 Shady Cove Ln, Winchester, TN 37398
/31
$255,000

Sold Apr 08, 2026

406 Asia Rd, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 1,416 Sq Ft
- Built 1974
Last Sold Summary
- 22% Below List Price
- $180/SF
- 153 Days On Market
Current Estimated Value $235,888

Last Listing Agent Lashun Burks WEICHERT, REALTORS - The Andrews Group

406 Asia Rd, Winchester, TN 37398
/91
$2,800,000

Sold Aug 31, 2026

323 Sunset Cove Ln, Winchester, TN 37398
- 3 Beds
- 4.5 Baths
- 4,637 Sq Ft
- Built 2024
Last Sold Summary
- 7% Below List Price
- $604/SF
- 23 Days On Market
Last Listing Agent Justin Briggs Freedom Realty

323 Sunset Cove Ln, Winchester, TN 37398
/22
$1,250,000

Sold Mar 30, 2026

517 Bluff Dr, Winchester, TN 37398
- 2 Beds
- 4 Baths
- 3,384 Sq Ft
- Built 1998
Last Sold Summary
- 5% Above List Price
- $369/SF
- 7 Days On Market
Current Estimated Value $1,209,432

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

517 Bluff Dr, Winchester, TN 37398
/49
$484,900

Sold Oct 14, 2025

332 Country Club Rd, Winchester, TN 37398
- 4 Beds
- 3 Baths
- 2,081 Sq Ft
- Built 2022
Last Sold Summary
- 7% Below List Price
- $233/SF
- 48 Days On Market
Current Estimated Value $501,467

Last Listing Agent Thomas Ore Winton Auction & Realty Co.

332 Country Club Rd, Winchester, TN 37398
/49
$380,000

Sold Mar 23, 2026

657 Country Club Ln, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 2,101 Sq Ft
- Built 2003
Last Sold Summary
- 3% Below List Price
- $181/SF
- 6 Days On Market
Current Estimated Value $391,676

Last Listing Agent Sabrina Kimball Simple Real Estate - Keller Williams

657 Country Club Ln, Winchester, TN 37398
/10
$65,000

Sold Jul 21, 2026

5468 Old Tullahoma Rd, Winchester, TN 37398
- Land
- 41,382 Sq Ft
- $68,421 per Acre
Last Sold Summary
- 19% Below List Price
- 69 Days On Market
Last Listing Agent Mandi Oakes Fridrich & Clark Realty

5468 Old Tullahoma Rd, Winchester, TN 37398
/21
$300,000

Sold Oct 30, 2025

17 Strawberry Dr, Winchester, TN 37398
- 4 Beds
- 2.5 Baths
- 2,402 Sq Ft
- Built 2003
Last Sold Summary
- 12% Below List Price
- $125/SF
- 181 Days On Market
Current Estimated Value $327,309

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

17 Strawberry Dr, Winchester, TN 37398
/73
$1,080,000

Sold Dec 19, 2025

45 Hammock Ct, Winchester, TN 37398
- 5 Beds
- 4.5 Baths
- 3,596 Sq Ft
- Built 2025
Last Sold Summary
- 6% Below List Price
- $300/SF
- 11 Days On Market
Last Listing Agent Earin Smotherman Reliant Realty ERA Powered

45 Hammock Ct, Winchester, TN 37398
/3
$112,000

Sold Jul 31, 2026

4 Anderton Dr, Winchester, TN 37398
- Land
- 2.13 Acres
- $52,533 per Acre
Last Sold Summary
- 28% Below List Price
- 385 Days On Market
Last Listing Agent isaac zimmerle Benchmark Realty, LLC

4 Anderton Dr, Winchester, TN 37398
/11
$64,999

Sold Aug 10, 2026

0 Lookout Dr Unit 42, 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 42, Winchester, TN 37398
/26
$219,900

Sold Dec 02, 2025

458 Woods Edge Rd, Winchester, TN 37398
- 3 Beds
- 1.5 Baths
- 1,040 Sq Ft
- Built 1998
Last Sold Summary
- $211/SF
- 11 Days On Market
Current Estimated Value $227,186

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

458 Woods Edge Rd, Winchester, TN 37398
/7
$225,000

Sold May 27, 2026

0 Ross Ln, Winchester, TN 37398
- Land
- 1.78 Acres
- $126,404 per Acre
Last Sold Summary
- 15% Above List Price
- 6 Days On Market
Last Listing Agent Cramer Foster Lynch Rigsby Realty & Auction, LLC

0 Ross Ln, Winchester, TN 37398
/45
$450,000

Sold Sep 14, 2026

188 Wiseman Ln, Winchester, TN 37398
- 4 Beds
- 2 Baths
- 2,269 Sq Ft
- Built 2025
Last Sold Summary
- 6% Below List Price
- $198/SF
- 58 Days On Market
Last Listing Agent Andrew Curl Better Homes & Gardens Real Estate Heritage Group

188 Wiseman Ln, Winchester, TN 37398
/52
$335,000

Sold Jun 17, 2026

1718 Galloway Ln, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 1,726 Sq Ft
- Built 2025
Last Sold Summary
- 14% Below List Price
- $194/SF
- 300 Days On Market
Last Listing Agent isaac zimmerle Benchmark Realty, LLC

1718 Galloway Ln, Winchester, TN 37398
/32
$495,000

Sold May 29, 2026

3115 Holders Cove Rd, Winchester, TN 37398
- 4 Beds
- 2.5 Baths
- 2,758 Sq Ft
- Built 2006
Last Sold Summary
- $179/SF
- 18 Days On Market
Current Estimated Value $528,031

Last Listing Agent James R. Cash James R. Cash II Auctions & Real Estate

3115 Holders Cove Rd, Winchester, TN 37398
/15
$135,000

Sold Oct 31, 2025

0 Lakeview Way, Winchester, TN 37398
- Land
- 1.19 Acres
- $113,828 per Acre
Last Sold Summary
- 103 Days On Market
Last Listing Agent Pelatiah Prince Winton Auction & Realty Co.

0 Lakeview Way, Winchester, TN 37398
/2
$615,000

Sold May 11, 2026

175 Dry Fork Dr, Winchester, TN 37398
- 3 Beds
- 3.5 Baths
- 2,523 Sq Ft
- Built 2021
Last Sold Summary
- $244/SF
- 0 Days On Market
Current Estimated Value $617,142

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

175 Dry Fork Dr, Winchester, TN 37398
/3
$115,000

Sold Mar 25, 2026

0 Cascade Dr Unit 7, Winchester, TN 37398
- Land
- 27,007 Sq Ft
- $185,484 per Acre
Last Sold Summary
- 21% Below List Price
- 9 Days On Market
Last Listing Agent Angela Miller John Smith Jr Realty and Auction LLC

0 Cascade Dr Unit 7, Winchester, TN 37398
/78
$750,000

Sold May 15, 2026

630 Shadowbrook Rd, Winchester, TN 37398
- 4 Beds
- 3.5 Baths
- 3,896 Sq Ft
- Built 1989
Last Sold Summary
- 5% Below List Price
- $193/SF
- 45 Days On Market
Current Estimated Value $761,185

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

630 Shadowbrook Rd, Winchester, TN 37398
/36
$270,000

Sold May 08, 2026

201&203 3rd Ave NE, Winchester, TN 37398
- 4 Beds
- 2 Baths
- 1,344 Sq Ft
- Built 1940
Last Sold Summary
- 2% Below List Price
- $201/SF
- 0 Days On Market
Last Listing Agent Lindsey Bruce Highlands Elite Real Estate LLC - Baxter

201&203 3rd Ave NE, Winchester, TN 37398
/31
$294,200

Sold Jun 16, 2026

102 Lisa Cir, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 1,380 Sq Ft
- Built 1986
Last Sold Summary
- 2% Below List Price
- $213/SF
- 32 Days On Market
Current Estimated Value $295,580

Last Listing Agent Eberley Holloway Southern Middle Realty

102 Lisa Cir, Winchester, TN 37398
/35
$535,000

Sold Feb 17, 2026

261 Franklin Heights Dr, Winchester, TN 37398
- 3 Beds
- 2.5 Baths
- 3,523 Sq Ft
- Built 2005
Last Sold Summary
- 7% Below List Price
- $152/SF
- 0 Days On Market
Current Estimated Value $558,410

Last Listing Agent Connie Wallace Century 21 Coffee County Realty & Auction

261 Franklin Heights Dr, Winchester, TN 37398
/53
$418,000

Sold Jul 23, 2026

123 Lookout Dr, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 1,869 Sq Ft
- Built 2026
Last Sold Summary
- $224/SF
- 21 Days On Market
Last Listing Agent Sandra Ayad Keller Williams Realty Mt. Juliet

123 Lookout Dr, Winchester, TN 37398
/48
$699,999

Sold May 14, 2026

64 Windjammer Ct, Winchester, TN 37398
- 3 Beds
- 3.5 Baths
- 2,841 Sq Ft
- Built 2025
Last Sold Summary
- $246/SF
- 0 Days On Market
Last Listing Agent Earin Smotherman Reliant Realty ERA Powered

64 Windjammer Ct, Winchester, TN 37398
/22
$168,000

Sold Feb 13, 2026

7010 Lynchburg Rd, Winchester, TN 37398
- 4 Beds
- 2 Baths
- 1,900 Sq Ft
- Built 2004
Last Sold Summary
- 11% Below List Price
- $88/SF
- 8 Days On Market
Last Listing Agent Daniel Prince John Smith Jr Realty and Auction LLC

7010 Lynchburg Rd, Winchester, TN 37398
/62
$740,000

Sold Oct 03, 2025

163 Wakeboard Way, Winchester, TN 37398
- 4 Beds
- 2.5 Baths
- 2,856 Sq Ft
- Built 2022
Last Sold Summary
- 1% Below List Price
- $259/SF
- 10 Days On Market
Current Estimated Value $676,266

Last Listing Agent Andrew (Andy) McInturff Zach Taylor Real Estate

163 Wakeboard Way, Winchester, TN 37398

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