Recently Sold Winchester, TN Homes

/64
$439,900

Sold Dec 26, 2025

348 Lookout Dr, Winchester, TN 37398
- 4 Beds
- 2 Baths
- 1,887 Sq Ft
- Built 2025
Last Sold Summary
- 2% Below List Price
- $233/SF
- 23 Days On Market
Last Listing Agent Christopher (Chr Tapp APP Realty

348 Lookout Dr, Winchester, TN 37398
/19
$60,000

Sold Aug 26, 2026

0 Shady Cove Ln Unit 40, Winchester, TN 37398
- Land
- 19,166 Sq Ft
- $136,364 per Acre
Last Sold Summary
- 52% Below List Price
- 129 Days On Market
Last Listing Agent Lisa Culp Taylor Onward Real Estate

0 Shady Cove Ln Unit 40, Winchester, TN 37398
/44
$375,000

Sold Sep 26, 2025

165 13th Ave NW, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 1,526 Sq Ft
- Built 2021
Last Sold Summary
- 6% Below List Price
- $246/SF
- 64 Days On Market
Current Estimated Value $403,860

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

165 13th Ave NW, Winchester, TN 37398
/38
$235,000

Sold Feb 18, 2026

811 Cumberland Dr, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 1,418 Sq Ft
- Built 1963
Last Sold Summary
- 13% Below List Price
- $166/SF
- 236 Days On Market
Current Estimated Value $239,393

Last Listing Agent Sharon Swafford Swaffords Property Shop

811 Cumberland Dr, Winchester, TN 37398
/9
$65,000

Sold Feb 03, 2026

0A Pickney Rd, Winchester, TN 37398
- Land
- 38,768 Sq Ft
- $73,034 per Acre
Last Sold Summary
- 7% Below List Price
- 17 Days On Market
Last Listing Agent Debbie DeLoach Crye-Leike, Realtors

0A Pickney Rd, Winchester, TN 37398
/23
$188,000

Sold Apr 23, 2026

103 Dalewood Dr, Winchester, TN 37398
- 3 Beds
- 1.5 Baths
- 1,120 Sq Ft
- Built 1976
Last Sold Summary
- 1% Below List Price
- $168/SF
- 7 Days On Market
Current Estimated Value $194,903

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

103 Dalewood Dr, Winchester, TN 37398
/53
$824,999

Sold Dec 04, 2025

70 Hammock Dr, Winchester, TN 37398
- 5 Beds
- 4.5 Baths
- 3,121 Sq Ft
- Built 2023
Last Sold Summary
- $264/SF
- 71 Days On Market
Current Estimated Value $860,181

Last Listing Agent David Price Crye-Leike, Inc., REALTORS

70 Hammock Dr, Winchester, TN 37398
/12
$155,000

Sold Nov 21, 2025

0 Huntington Dr N Unit RTC2988373, Winchester, TN 37398
- Land
- 26,136 Sq Ft
- $258,333 per Acre
Last Sold Summary
- 6% Below List Price
- 47 Days On Market
Last Listing Agent Rachel Stokes Benchmark Realty, LLC

0 Huntington Dr N Unit RTC2988373, Winchester, TN 37398
/29
$365,000

Sold Mar 03, 2026

17 Favre Cir, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 1,615 Sq Ft
- Built 1999
Last Sold Summary
- 3% Below List Price
- $226/SF
- 67 Days On Market
Current Estimated Value $373,327

Last Listing Agent Marcia Long Franklin County Realty

17 Favre Cir, Winchester, TN 37398
/27
$218,000

Sold Jun 18, 2026

215 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
Current Estimated Value $377,428

Last Listing Agent Earin Smotherman Reliant Realty ERA Powered

215 S Porter St, Winchester, TN 37398
/56
$1,300,000

Sold Aug 26, 2026

644 Fanning Bend Dr, Winchester, TN 37398
- 4 Beds
- 3.5 Baths
- 3,922 Sq Ft
- Built 2022
Last Sold Summary
- 15% Below List Price
- $331/SF
- 140 Days On Market
Current Estimated Value $1,539,667

Last Listing Agent Clay Kelton eXp Realty

644 Fanning Bend Dr, Winchester, TN 37398
/30
$244,900

Sold Mar 17, 2026

210 E Petty Ln, Winchester, TN 37398
- 3 Beds
- 1.5 Baths
- 1,250 Sq Ft
- Built 1970
Last Sold Summary
- 5% Below List Price
- $196/SF
- 77 Days On Market
Current Estimated Value $250,163

Last Listing Agent Patricia Mathis Lake Homes Realty, LLC

210 E Petty Ln, Winchester, TN 37398
/66
$535,000

Sold Aug 10, 2026

657 Pickney Rd, Winchester, TN 37398
- 3 Beds
- 2.5 Baths
- 2,782 Sq Ft
- Built 2008
Last Sold Summary
- 11% Below List Price
- $192/SF
- 182 Days On Market
Current Estimated Value $596,706

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

657 Pickney Rd, Winchester, TN 37398
/18
$113,000

Sold Apr 27, 2026

211 Wilson St, Winchester, TN 37398
- 4 Beds
- 2 Baths
- 1,248 Sq Ft
- Built 1989
Last Sold Summary
- 3% Above List Price
- $91/SF
- 6 Days On Market
Current Estimated Value $117,690

Last Listing Agent Donna Corbin Corbin & Company Realty, LLC

211 Wilson St, Winchester, TN 37398
/32
$382,500

Sold May 29, 2026

114 Edgefield Ct, Winchester, TN 37398
- 2 Beds
- 2 Baths
- 1,640 Sq Ft
- Built 2025
Last Sold Summary
- 4% Below List Price
- $233/SF
- 26 Days On Market
Last Listing Agent Angela Miller John Smith Jr Realty and Auction LLC

114 Edgefield Ct, Winchester, TN 37398
/31
$265,000

Sold Aug 10, 2026

112 Bel Aire Dr, Winchester, TN 37398
- 3 Beds
- 1.5 Baths
- 1,701 Sq Ft
- Built 1967
Last Sold Summary
- 7% Below List Price
- $156/SF
- 38 Days On Market
Current Estimated Value $270,177

Last Listing Agent Elizabeth Padgett Century 21 Volunteer Realty

112 Bel Aire Dr, Winchester, TN 37398
/56
$1,100,000

Sold Sep 30, 2025

645 Wildwood Trace, Winchester, TN 37398
- 2 Beds
- 3 Baths
- 2,136 Sq Ft
- Built 1992
Last Sold Summary
- 8% Below List Price
- $515/SF
- 8 Days On Market
Current Estimated Value $1,231,402

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

645 Wildwood Trace, Winchester, TN 37398
/46
$374,900

Sold Nov 05, 2025

461 Royal Oak Dr, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 2,247 Sq Ft
- Built 1977
Last Sold Summary
- 6% Below List Price
- $167/SF
- 35 Days On Market
Current Estimated Value $399,537

Last Listing Agent Chelsea Greenway Southern Middle Realty

461 Royal Oak Dr, Winchester, TN 37398
/17
$319,860

Sold Jan 09, 2026

5257 Holders Cove Rd, Winchester, TN 37398
- Land
- 17.77 Acres
- $18,000 per Acre
Last Sold Summary
- 17 Days On Market
Current Estimated Value $404,404

Last Listing Agent Thomas Ore Winton Auction & Realty Co.

5257 Holders Cove Rd, Winchester, TN 37398
/4
$195,000

Sold May 09, 2026

0 Old Estill Springs Rd Unit 4, Winchester, TN 37398
- Land
- 10.2 Acres
- $19,118 per Acre
Last Sold Summary
- 2% Below List Price
- 68 Days On Market
Last Listing Agent Mike Mcalister Woodruff Realty & Auction

0 Old Estill Springs Rd Unit 4, Winchester, TN 37398
/38
$462,500

Sold Jul 30, 2026

74 Pine Bluff Rd, Winchester, TN 37398
- 3 Beds
- 2.5 Baths
- 2,308 Sq Ft
- Built 2019
Last Sold Summary
- 1% Below List Price
- $200/SF
- 21 Days On Market
Current Estimated Value $466,100

Last Listing Agent Jeromey Cromwell RE/MAX 1st Realty

74 Pine Bluff Rd, Winchester, TN 37398
/32
$441,000

Sold Apr 23, 2026

246 Lookout Dr, Winchester, TN 37398
- 4 Beds
- 2 Baths
- 2,044 Sq Ft
- Built 2023
Last Sold Summary
- 2% Below List Price
- $216/SF
- 29 Days On Market
Current Estimated Value $455,065

Last Listing Agent Melissa Stewart Swaffords Property Shop

246 Lookout Dr, Winchester, TN 37398
/3
$73,750

Sold Feb 18, 2026

0 Deer Valley Cir Unit RTC2980785, Winchester, TN 37398
- Land
- 9,147 Sq Ft
- $351,190 per Acre
Last Sold Summary
- 4% Below List Price
- 169 Days On Market
Last Listing Agent Ashley Lynch Lynch Rigsby Realty & Auction, LLC

0 Deer Valley Cir Unit RTC2980785, Winchester, TN 37398
/31
$299,000

Sold Jun 18, 2026

70 Crestview Dr, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 1,288 Sq Ft
- Built 2023
Last Sold Summary
- 3% Below List Price
- $232/SF
- 16 Days On Market
Last Listing Agent Erin Kehely Steve Jernigan Realty

70 Crestview Dr, Winchester, TN 37398
/10
$126,000

Sold Jun 17, 2026

0 Maple Bend Rd, Winchester, TN 37398
- Land
- 2.67 Acres
- $47,191 per Acre
Last Sold Summary
- 16% Below List Price
- 254 Days On Market
Last Listing Agent Angela Miller John Smith Jr Realty and Auction LLC

0 Maple Bend Rd, Winchester, TN 37398
/37
$350,000

Sold Jul 13, 2026

52 Island Way, Winchester, TN 37398
- 2 Beds
- 2 Baths
- 1,339 Sq Ft
- Built 2019
Last Sold Summary
- 4% Below List Price
- $261/SF
- 92 Days On Market
Current Estimated Value $359,954

Last Listing Agent Shelia Lunsford Benchmark Realty, LLC

52 Island Way, Winchester, TN 37398
/6
$1

Sold Apr 07, 2026

0 Aedc Rd Unit 2, Winchester, TN 37398
- Land
- 3.72 Acres
Last Sold Summary
- 52 Days On Market
Last Listing Agent Thomas Ore Winton Auction & Realty Co.

0 Aedc Rd Unit 2, Winchester, TN 37398
/2
$60,000

Sold Aug 12, 2026

0 Old Tullahoma Rd Unit 1, Winchester, TN 37398
- Land
- 27,442 Sq Ft
- $95,238 per Acre
Last Sold Summary
- 8% Below List Price
- 34 Days On Market
Last Listing Agent Mitch Umbarger Better Homes & Gardens Real Estate Heritage Group

0 Old Tullahoma Rd Unit 1, Winchester, TN 37398
/64
$325,000

Sold Apr 09, 2026

144 Wood Bluff Rd, Winchester, TN 37398
- 4 Beds
- 3 Baths
- 2,528 Sq Ft
- Built 1978
Last Sold Summary
- 13% Below List Price
- $129/SF
- 13 Days On Market
Current Estimated Value $348,917

Last Listing Agent Melissa Stewart Swaffords Property Shop

144 Wood Bluff Rd, Winchester, TN 37398
/3
$73,750

Sold Apr 06, 2026

0 Deer Valley Cir Unit 28, Winchester, TN 37398
- Land
- 12,632 Sq Ft
- $254,310 per Acre
Last Sold Summary
- 4% Below List Price
- 169 Days On Market
Last Listing Agent Ashley Lynch Lynch Rigsby Realty & Auction, LLC

0 Deer Valley Cir Unit 28, Winchester, TN 37398
/96
$615,000

Sold Sep 17, 2026

426 Maple Bend Rd, Winchester, TN 37398
- 4 Beds
- 2.5 Baths
- 2,981 Sq Ft
- Built 2022
Last Sold Summary
- 1% Below List Price
- $206/SF
- 20 Days On Market
Current Estimated Value $702,195

Last Listing Agent Eberley Holloway Southern Middle Realty

426 Maple Bend Rd, Winchester, TN 37398
/37
$426,000

Sold Sep 17, 2026

146 Holly Dr, Winchester, TN 37398
- 3 Beds
- 3 Baths
- 2,348 Sq Ft
- Built 1990
Last Sold Summary
- 7% Below List Price
- $181/SF
- 8 Days On Market
Current Estimated Value $534,281

Last Listing Agent Samantha Dickey John Smith Jr Realty and Auction LLC

146 Holly Dr, Winchester, TN 37398
/21
$208,500

Sold Sep 24, 2025

735 Haddon Ln, Winchester, TN 37398
- 3 Beds
- 1 Bath
- 1,176 Sq Ft
- Built 2011
Last Sold Summary
- 1% Below List Price
- $177/SF
- 6 Days On Market
Current Estimated Value $237,877

Last Listing Agent Edward Brock Lynch Rigsby Realty & Auction, LLC

735 Haddon Ln, Winchester, TN 37398
/44
$349,900

Sold Mar 26, 2026

311 N Jefferson St, Winchester, TN 37398
- 4 Beds
- 2 Baths
- 3,888 Sq Ft
- Built 1923
Last Sold Summary
- 13% Below List Price
- $90/SF
- 124 Days On Market
Current Estimated Value $363,700

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

311 N Jefferson St, Winchester, TN 37398
/53
$1,550,000

Sold Mar 03, 2026

86 Simmons Cir, Winchester, TN 37398
- 4 Beds
- 5 Baths
- 4,089 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $379/SF
- 92 Days On Market
86 Simmons Cir, Winchester, TN 37398
/51
$560,000

Sold Jun 23, 2026

891 Hopkins Ln, Winchester, TN 37398
- 3 Beds
- 4 Baths
- 3,534 Sq Ft
- Built 2013
Last Sold Summary
- 3% Below List Price
- $158/SF
- 17 Days On Market
Current Estimated Value $594,753

Last Listing Agent Fhonda Hatmaker eXp Realty

891 Hopkins Ln, Winchester, TN 37398
/27
$310,000

Sold Feb 05, 2026

43 Liberty Rd, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 1,525 Sq Ft
- Built 1979
Last Sold Summary
- 3% Below List Price
- $203/SF
- 21 Days On Market
Current Estimated Value $319,554

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

43 Liberty Rd, Winchester, TN 37398
/37
$330,000

Sold May 07, 2026

6606 Old Tullahoma Rd, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 1,972 Sq Ft
- Built 1929
Last Sold Summary
- 3% Below List Price
- $167/SF
- 1 Day On Market
Current Estimated Value $436,051

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

6606 Old Tullahoma Rd, Winchester, TN 37398
/33
$390,000

Sold Oct 06, 2025

137 Favre Cir, Winchester, TN 37398
- 4 Beds
- 3 Baths
- 2,255 Sq Ft
- Built 2002
Last Sold Summary
- 7% Below List Price
- $173/SF
- 89 Days On Market
Current Estimated Value $414,671

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

137 Favre Cir, Winchester, TN 37398
/21
$342,000

Sold Jun 12, 2026

1680 Bypass Rd, Winchester, TN 37398
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
- Built 1972
Last Sold Summary
- $244/SF
- 14 Days On Market
Current Estimated Value $321,106

Last Listing Agent Pelatiah Prince Winton Auction & Realty Co.

1680 Bypass Rd, Winchester, TN 37398

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