Winchester, TN Homes

• 

  

  

  /8

  $63,000

  Sold Nov 14, 2025

  0 Lookout Dr Unit RTC2976836, Winchester, TN 37398

  • Land
  • 42,253 Sq Ft
  • $64,948 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 58 Days On Market

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

  0 Lookout Dr Unit RTC2976836, Winchester, TN 37398
• 

  

  

  /22

  Est $215,369

  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

  • 3% Above List Price
  • $190/SF
  • 12 Days On Market

  • Last Sold Price $210,000
  • Apr 29, 2025

  Last Listing Agent Maria Checchin Crye-Leike Realtors South, Inc.
• 

  

  

  /54

  $439,000

  • 4 Beds
  • 2.5 Baths
  • 2,660 Sq Ft

  58 Island Way, Winchester, TN 37398

  Low maintenance living meets lake life luxury in this beautifully designed townhome tucked inside a gated community loaded with amenities! Whether you're looking for a full-time residence or the perfect weekend escape, this one checks all the boxes. Step inside to find a spacious layout featuring a primary suite on the main level, offering convenience and comfort. The spa-like bath is your

  Angela Miller John Smith Jr Realty and Auction LLC

  58 Island Way, Winchester, TN 37398
• 

  

  

  /5

  $60,000

  Sold Aug 13, 2025

  0 Lynchburg Rd Unit RTC2899282, Winchester, TN 37398

  • Land
  • 37,897 Sq Ft
  • $68,966 per Acre

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  0 Lynchburg Rd Unit RTC2899282, Winchester, TN 37398
• 

  

  

  /45

  Est $325,177

  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

  • 5% Above List Price
  • $186/SF
  • 14 Days On Market

  • Last Sold Price $310,000
  • Jul 31, 2024

  Last Listing Agent Sharon Swafford Swaffords Property Shop
• 

  

  /64

  $475,000

  • 5 Beds
  • 2 Baths
  • 3,922 Sq Ft

  309 2nd Ave NW, Winchester, TN 37398

  Income-producing property just over a block from downtown Winchester, offering a rare opportunity for buyers seeking investment property in Tennessee with immediate rental income and future flexibility. Built in 1917, this historic, commercially zoned 5-bedroom, 2-bath residence generates approximately $2,000/month in rental income and includes approximately 3,922 sq ft on a .34-acre lot in the

  Robert Duncan eXp Realty

  309 2nd Ave NW, Winchester, TN 37398
• 

  

  /18

  $280,000

  Sold Sep 11, 2025

  117 Raspberry Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,489 Sq Ft
  • Built 2018

  Last Sold Summary

  • 8% Below List Price
  • $188/SF
  • 88 Days On Market

  Current Estimated Value $283,739

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

  117 Raspberry Dr, Winchester, TN 37398
• 

  

  /32

  Est $194,594

  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

  • $169/SF
  • 337 Days On Market

  • Last Sold Price $195,000
  • Mar 28, 2025

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

  

  /63

  $559,900

  New Construction $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,973 Sq Ft

  249 Lookout Dr, Winchester, TN 37398

  Builder offering up to $10,000 toward buyer incentives!MOTIVATED BUILDER – READY TO MOVE ON! BRING ALL OFFERS! Welcome to 249 Lookout Drive in Winchester, TN — a stunning new construction home that blends modern comfort, quality craftsmanship, and timeless style. This 3-bedroom, 2.5-bath residence offers a bright, open-concept layout designed for both everyday living and effortless

  Charlie Gonzales Southern Middle Realty

  249 Lookout Dr, Winchester, TN 37398
• 

  

  /50

  $299,900

  Sold Nov 13, 2025

  115 Oak Leaf Cir, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Built 1990

  Last Sold Summary

  • $204/SF
  • 12 Days On Market

  Current Estimated Value $294,781

  Last Listing Agent Jessica London Southern Middle Realty

  115 Oak Leaf Cir, Winchester, TN 37398
• 

  

  /31

  Est $190,229

  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% Below List Price
  • $211/SF
  • 4 Days On Market

  • Last Sold Price $197,900
  • Jul 17, 2024

  Last Listing Agent Victoria Hinson The Realty Association
• 

  

  /23

  $545,000

  • 3 Beds
  • 2.5 Baths
  • 2,276 Sq Ft

  23 Skidmore Ln, Winchester, TN 37398

  Large open layout home, a detached 3 car garage with bonus room above, and all on a gorgeous corner country lot - this home checks all of the boxes... All-brick home on almost a full acre corner lot just minutes from Winchester offering over 2,200 sq ft, with 3 bedrooms, and 2.5 baths and an office space. Features a spacious layout with generous living areas, a well-designed kitchen, and a large

  Ashley Nelson Franklin County Realty

  23 Skidmore Ln, Winchester, TN 37398
• 

  

  /55

  $439,900

  Sold Dec 02, 2025

  197 Murray Lake Dr, Winchester, TN 37398

  • 3 Beds
  • 3 Baths
  • 2,528 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Below List Price
  • $174/SF
  • 22 Days On Market

  Current Estimated Value $437,973

  Last Listing Agent David Janke Canopy Real Estate

  197 Murray Lake Dr, Winchester, TN 37398
• 

  

  /43

  Est $1,099,213

  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

  • 15% Below List Price
  • $518/SF
  • 4 Days On Market

  • Last Sold Price $1,300,000
  • Sep 15, 2023

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

  

  /38

  $510,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,388 Sq Ft

  512 Cline Ridge Rd, Winchester, TN 37398

  Most people think you have to choose between land and lake life... but here, you get both. Enjoy backyard bonfires, nights under the stars and private dock access just ~400 yards from the house. You're on the water in minutes with no long idle zones and quick access to open water for boating, surfing, swimming, and sunset cruises. Located in a calm no-wake zone, the water stays peaceful and safe,

  Jordan Crouch Benchmark Realty, LLC

  512 Cline Ridge Rd, Winchester, TN 37398
• 

  

  /9

  $250,000

  Sold Jun 23, 2025

  75 Troy Ct, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Built 2017

  Last Sold Summary

  • $195/SF
  • 3 Days On Market

  Current Estimated Value $255,716

  Last Listing Agent Kelly Smith RE/MAX 1st Realty

  75 Troy Ct, Winchester, TN 37398
• 

  

  /20

  Est $197,081

  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

  • 15% Above List Price
  • $153/SF
  • 32 Days On Market

  • Last Sold Price $171,000
  • Apr 19, 2024

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

  

  /24

  $479,900

  New Construction

  • 4 Beds
  • 2 Baths
  • 2,269 Sq Ft

  188 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 1.386 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

  188 Wiseman Ln, Winchester, TN 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 $272,399

  Last Listing Agent Connie Landers BHGRE Baker & Cole

  41 Cheyenne Ave, Winchester, TN 37398
• 

  

  /30

  Est $270,836

  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

  • 2% Above List Price
  • $151/SF
  • 40 Days On Market

  • Last Sold Price $265,000
  • Nov 20, 2023

  Last Listing Agent Lauren Bailey Swaffords Property Shop
• 

  

  /54

  $499,000

  • 6 Beds
  • 4 Baths
  • 3,158 Sq Ft

  109 Carter Farris Ln, Winchester, TN 37398

  Nestled on 2.4 enchanting acres, this grand 6-bedroom, 4 bath country estate feels like a storybook come to life. Beneath a canopy of towering shade trees, the home rises with grace and charm, offering space as vast as imagination itself. Inside each room is generous in size. Perfect for gathering with family and friends. Full unfinished basement offers plenty of space for storage, workshop, etc.

  Angela Miller John Smith Jr Realty and Auction LLC

  109 Carter Farris Ln, 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 $331,772

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  1956 Old Estill Springs Rd, Winchester, TN 37398
• 

  

  /24

  Est $179,897

  Not Listed For Sale

  406 7th Ave NW, Winchester, TN 37398

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1953

  406 7th Ave NW, Winchester, TN 37398

  Last Sold Summary

  • 14% Below List Price
  • $175/SF
  • 23 Days On Market

  • Last Sold Price $209,900
  • Apr 16, 2024

  Last Listing Agent Stephanie Dowdy Freedom Realty Group
• 

  

  /33

  $469,900

  Pending

  • 4 Beds
  • 3 Baths
  • 2,348 Sq Ft

  146 Holly Dr, Winchester, TN 37398

  Beautiful home located in the desirable Holly Hills neighborhood of Winchester, Tennessee. Minutes from shopping, dining and recreational opportunities like our beautiful lake at Tims Ford. This home offers 4 bedrooms and 3 baths with an attached 2 car garage on a .72 acre level lot. It also includes an insulated 24x24 shop and a 12x24 outbuilding for ample storage. Come see why this could be the

  Samantha Dickey John Smith Jr Realty and Auction LLC

  146 Holly Dr, 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
• 

  

  /56

  Est $446,184

  Not Listed For Sale

  318 Shadowbrook Rd, Winchester, TN 37398

  • 5 Beds
  • 3.5 Baths
  • 3,492 Sq Ft
  • Built 1968

  318 Shadowbrook Rd, Winchester, TN 37398

  Last Sold Summary

  • 10% Above List Price
  • $116/SF
  • 54 Days On Market

  • Last Sold Price $405,000
  • Mar 20, 2025

  Last Listing Agent Billie Kay Caldwell Swaffords Property Shop
• 

  

  /82

  $464,900

  • 4 Beds
  • 3 Baths
  • 2,038 Sq Ft

  963 Lynchburg Rd, Winchester, TN 37398

  Income producing property. Used as short term and long term rental with healthy returns.Located across the street from Twin Creeks Marina on Tims Ford Lake, this perfectly renovated, 4 bedroom, 3 bath home is selling fully furnished with high-end furniture and decor. Open, spacious, and airy floor plan offers 2 bedrooms down, kitchen with stainless appliances, dining room, 2 bedrooms upstairs

  Mimi Genet Parks Auction & Realty

  963 Lynchburg Rd, 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 $399,317

  Last Listing Agent Billie Kay Caldwell Swaffords Property Shop

  1050 Franklin Heights Dr, Winchester, TN 37398
• 

  

  /24

  Est $171,832

  Not Listed For Sale

  1401 Old Cowan Rd, Winchester, TN 37398

  • 2 Beds
  • 1 Bath
  • 783 Sq Ft
  • Built 1928

  1401 Old Cowan Rd, Winchester, TN 37398

  Last Sold Summary

  • 1% Below List Price
  • $222/SF
  • 92 Days On Market

  • Last Sold Price $173,900
  • Aug 31, 2023

  Last Listing Agent Sheila Chilton Keller Williams Russell Realty & Auction
• 

  

  /33

  $439,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,564 Sq Ft

  211 Miller Farm Ln, Winchester, TN 37398

  “Reduced Price"... BEAUTIFUL HOME on 5.42 acres just minutes from Winchester! This 3 BR, 2 BA home, built in 2023, features a modern black metal exterior and metal roof for durability and low maintenance, along with a spacious 2-car garage. Enjoy comfortable living with large covered porch on both front and back, an open layout with generous bedrooms, plus a large crawl space offering excellent

  Donald Barnes Coldwell Banker Southern Realty

  211 Miller Farm Ln, 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
• 

  

  /19

  Est $235,258

  Not Listed For Sale

  208 Franklin Park, Winchester, TN 37398

  • 3 Beds
  • 1 Bath
  • 1,242 Sq Ft
  • Built 1956

  208 Franklin Park, Winchester, TN 37398

  Last Sold Summary

  • 1% Above List Price
  • $187/SF
  • 112 Days On Market

  • Last Sold Price $232,500
  • Oct 18, 2024

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

  

  /92

  $570,000

  $30K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,510 Sq Ft

  101 Westmeade Dr, Winchester, TN 37398

  Welcome to this beautifully crafted residence in the highly desirable Franklin Heights subdivision. Offering over 3,500 sq. ft. of living space, this two-story home features 5 bedrooms, 4.5 bathrooms, a dedicated office and a 2 car garage. From the moment you step into the grand foyer, you’re greeted with timeless details, including a formal dining room to your left and a private office to your

  Eberley Holloway Southern Middle Realty

  101 Westmeade Dr, 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 $232,635

  Last Listing Agent Ben Absher Realty One Group Experts

  

  114 11th Ave NW, Winchester, TN 37398
• 

  

  /30

  Est $248,690

  Not Listed For Sale

  1390 Water Tank Rd, Winchester, TN 37398

  • 3 Beds
  • 1 Bath
  • 1,700 Sq Ft
  • Built 1900

  1390 Water Tank Rd, Winchester, TN 37398

  Last Sold Summary

  • 12% Above List Price
  • $131/SF
  • 9 Days On Market

  • Last Sold Price $223,000
  • Dec 02, 2024

  Last Listing Agent Logan Iliescu Bradford Real Estate
• 

  

  /56

  $550,000

  $60K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,682 Sq Ft

  145 Franklin Heights Dr, Winchester, TN 37398

  Welcome home to comfort, space, and peaceful surroundings in this beautifully designed mostly one-level home nestled on one of the largest lots in Franklin Hills-- a generous 1.64 acres. Thoughtfully laid out with everyday living on the main floor, this home is ideal for those seeking easy convenient living without sacrificing room to spread out. The main level features three spacious bedrooms

  Thomas Ore Winton Auction & Realty Co.

  145 Franklin Heights Dr, 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 $285,351

  Not Listed For Sale

  117 Dogwood Ln, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 2,158 Sq Ft
  • Built 1949

  117 Dogwood Ln, Winchester, TN 37398

  Last Sold Summary

  • 14% Above List Price
  • $116/SF
  • 38 Days On Market

  • Last Sold Price $250,000
  • Nov 19, 2024

  Last Listing Agent Eberley Holloway Southern Middle Realty
• 

  /2

  $275,000

  • 4 Beds
  • 2 Baths
  • 1,930 Sq Ft

  810 N High St, Winchester, TN 37398

  Great duplex in perfect location...convenient to Tims Ford lake, Twin Creeks marina and downtown Winchester! One side had an extensive overhaul in 2025. Both sides are currently rented at 975.00 each. Great return on your money! Allow 24hr showing notice to alert tenants.

  Curtis Benchmark Realty, LLC

  810 N High St, 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 $454,432

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

  300 Old Clark Rd, Winchester, TN 37398

Showing Results 241 - 280, Page 7 of 18