Winchester, TN Homes

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  /57

  $842,900

  $34K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,484 Sq Ft

  282 Owl Hollow Ln, Winchester, TN 37398

  VERY MOTVATED SELLER, Beautiful Lake house perfect for multi families. A cozy fireplace adds a touch of warmth and charm to the inviting living space. w/master located on top floor w/custom walk-in shower, oversized Jacuzzi tub and private entrance to the covered deck. 2 guest rooms upstairs, and extra guest suite downstairs and lots of open space for entertaining, back patio for relaxing

  Sam Hatfield Sam Hatfield Realty, Inc.

  282 Owl Hollow Ln, Winchester, TN 37398
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  /38

  $260,000

  Sold Aug 29, 2025

  115 Highland Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • Built 1952

  Last Sold Summary

  • 4% Below List Price
  • $192/SF
  • 96 Days On Market

  Current Estimated Value $259,155

  Last Listing Agent Fhonda Hatmaker eXp Realty

  115 Highland Dr, Winchester, TN 37398
• 

  

  

  /16

  Est $177,574

  Not Listed For Sale

  101 Highland St, Winchester, TN 37398

  • 2 Beds
  • 1 Bath
  • 885 Sq Ft
  • Built 1950

  101 Highland St, Winchester, TN 37398

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Fhonda Hatmaker eXp Realty
• 

  

  

  /62

  $429,900

  $19K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,431 Sq Ft

  90 Owl Hollow Ln, Winchester, TN 37398

  Located near Tims Ford Lake with deeded lake access, this well-built all brick home offers privacy, space, and plenty of potential on 2.64 wooded acres. With 2,431 sq ft, the home features 3 bedrooms, 2.5 bathrooms, a sunroom, large basement, garage, and attached carport. Mature trees provide a peaceful setting with room to enjoy the outdoors while still being just minutes from Tims Ford State

  Clay Dunivan Simple Real Estate - Keller Williams

  90 Owl Hollow Ln, Winchester, TN 37398
• 

  

  

  /18

  $228,000

  Sold Jun 25, 2026

  286 Strawberry Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 2003

  Last Sold Summary

  • 16% Below List Price
  • $198/SF
  • 146 Days On Market

  Current Estimated Value $232,033

  Last Listing Agent Rachel Ferrell Southern Middle Realty

  286 Strawberry Dr, Winchester, TN 37398
• 

  

  /14

  Est $184,862

  Not Listed For Sale

  100 Mountain View Dr, Winchester, TN 37398

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1963

  100 Mountain View Dr, Winchester, TN 37398

  Last Sold Summary

  • 92 Days On Market

  Last Listing Agent Mike Stubblefield Franklin County Realty
• 

  

  /5

  $177,000

  $43K PRICE DROP

  • Land
  • 3.16 Acres
  • $56,013 per Acre

  5 Anderton Dr, Winchester, TN 37398

  Tims Ford Lake WATER VIEW large lot. 3.16 acreLot. AMAZING water views. water access very very close. Hard to find LARGE LOT near the Lake. Build your custom dream home on this beautiful, year round water view site. This lot is situated on a private driveway access and enjoys additional privacy with Tim’s Ford State Park property next door. Enjoy 180-degree view of beautiful Tims Ford Lake and

  isaac zimmerle Benchmark Realty, LLC

  5 Anderton Dr, Winchester, TN 37398
• 

  

  /26

  $389,000

  Sold Mar 31, 2026

  295 Metcalf Rd, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 1999

  Last Sold Summary

  • 9% Below List Price
  • $216/SF
  • 115 Days On Market

  Current Estimated Value $398,344

  Last Listing Agent Jerry Shelton Shelton Auction and Realty

  295 Metcalf Rd, Winchester, TN 37398
• 

  

  /13

  Est $177,033

  Not Listed For Sale

  117 11th Ave NW, Winchester, TN 37398

  • 3 Beds
  • 1 Bath
  • 1,003 Sq Ft
  • Built 1953

  117 11th Ave NW, Winchester, TN 37398

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Moronke Olubola United Real Estate Middle Tennessee
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  /62

  $1,229,900

  • 4 Beds
  • 4 Baths
  • 3,720 Sq Ft

  160 Wakeboard Way, Winchester, TN 37398

  Incredible opportunity to own a well appointed custom designed home that can be purchased with a Varity of furnishings The list price includes a 8000# hydro hoist lift and 12 months of paid boat slip rental that is 32 ft long. In this is a home you will find attention to finest details speaks for themselves. Starting with the porcelain pavers at the front entry, hardwood throughout the main floor

  Angela Privett Benchmark Realty, LLC

  160 Wakeboard Way, 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 $789,914

  Last Listing Agent Rachel Ferrell Southern Middle Realty

  190 Cascade Dr, Winchester, TN 37398
• 

  

  /35

  Est $399,100

  Not Listed For Sale

  95 Audobon Dr, Winchester, TN 37398

  • 4 Beds
  • 2 Baths
  • 1,948 Sq Ft
  • Built 1994

  95 Audobon Dr, Winchester, TN 37398

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Teresa Young WEICHERT, REALTORS Joe Orr & Associates
• 

  

  /4

  $64,900

  • Land
  • 23,958 Sq Ft
  • $118,000 per Acre

  66 Edgefield Ct, Winchester, TN 37398

  New Gated Community, The Highlands! Located less than one minute from Tims Ford Lake (public boat launch on Sharp Springs Rd). Convenient to shopping and dining.

  Sharon Swafford Swaffords Property Shop

  66 Edgefield Ct, Winchester, TN 37398
• 

  

  /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 $252,347

  Last Listing Agent Sharon Swafford Swaffords Property Shop

  136 Bel Aire Dr, Winchester, TN 37398
• 

  

  /10

  Est $255,189

  Not Listed For Sale

  140 Bel Aire Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,238 Sq Ft
  • Built 1965

  140 Bel Aire Dr, Winchester, TN 37398

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Jonathan Harris ResultsMLS Realtors
• 

  

  /89

  $1,050,000

  $145K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,906 Sq Ft

  208 Loop Dr, Winchester, TN 37398

  Welcome to Luxury Lake Life on Tims Ford Lake!! Discover refined waterfront living with this stately brick home complete with your very own private boat dock. Boasting 4 spacious bedrooms and 3.5 beautifully appointed bathrooms, this home offers the perfect blend of elegance and comfort. Step inside to find exquisite custom trim and architectural details throughout. The culinary kitchen is a

  Jessica London Southern Middle Realty

  208 Loop Dr, Winchester, TN 37398
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  /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
• 

  

  /35

  Est $291,141

  Not Listed For Sale

  280 Susie Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Built 1993

  280 Susie Dr, Winchester, TN 37398

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Bonnie Schiffner John Smith Jr Realty and Auction LLC
• 

  

  /40

  $435,000

  $25K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,425 Sq Ft

  102 Cannonball Ct, Winchester, TN 37398

  Every great lake story begins with finding the perfect place to call home.. and this one is waiting for its next chapter. Nestled inside a gated lake community, this charming 2 master bedroom, 2 bath retreat is where everyday life feels like a getaway. Wake up with a cup of coffee on the porch swing as the morning breeze drifts through the lush landscaping, then end your evenings gathered around

  Angela Miller John Smith Jr Realty and Auction LLC

  102 Cannonball Ct, Winchester, TN 37398
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  /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 $229,075

  Last Listing Agent Rachel Ferrell Southern Middle Realty

  190 Cheyenne Ave, Winchester, TN 37398
• 

  

  /4

  Est $211,648

  Not Listed For Sale

  1309 Old Cowan Rd, Winchester, TN 37398

  • 2 Beds
  • 1 Bath
  • 1,284 Sq Ft
  • Built 1949

  1309 Old Cowan Rd, Winchester, TN 37398

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Sean Crabtree Blue Door Realty Group
• 

  

  /48

  $1,750,000

  903 Old Estill Springs Rd, Winchester, TN 37398

  Exceptional 47.5± acre residential development opportunity in the heart of Winchester, TN. This predominantly level, well-drained farm offers frontage on Old Estill Springs Rd., Bible Crossing Rd., and Myers Rd., providing multiple access points for a future subdivision or master-planned community. Adjacent to Winchester City Park, the property presents a rare opportunity to create a

  Thomas Ore Winton Auction & Realty Co.

  903 Old Estill Springs Rd, 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 $341,495

  Last Listing Agent Greg Sitz Parks Auction & Realty

  2425 Old Tullahoma Rd, Winchester, TN 37398
• 

  

  /12

  Est $315,072

  Not Listed For Sale

  152 Brookfield Cir, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1998

  152 Brookfield Cir, Winchester, TN 37398

  Last Sold Summary

  • 28 Days On Market

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

  

  /15

  $125,000

  $75K PRICE DROP

  • Land
  • 0 Sq Ft

  0 Slalom Cir Unit 104, Winchester, TN 37398

  RECENTLY REDUCED! Don’t miss this opportunity to own one of the few remaining water-view building lots in the highly sought-after Twin Creeks Village community. Located on prestigious Lot #104 Slalom Circle, this prime homesite sits on one of the most desirable streets in the development—an ideal setting to build your custom water-view dream home in a peaceful, upscale lakeside

  Felicia Wright Leading Edge Real Estate Group

  0 Slalom Cir Unit 104, 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 $517,581

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

  105 Twilight Dr, Winchester, TN 37398
• 

  

  /58

  Est $605,647

  Not Listed For Sale

  3836 Decherd Estill Rd, Winchester, TN 37398

  • 4 Beds
  • 3.5 Baths
  • 2,938 Sq Ft
  • Built 1993

  

  3836 Decherd Estill Rd, Winchester, TN 37398

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Shannon Ball Tennessee Mountain Properties
• 

  

  /26

  $799,900

  $15K PRICE DROP Under Contract

  • 4 Beds
  • 3 Baths
  • 3,279 Sq Ft

  206 Knott Rd, Winchester, TN 37398

  206 Knott Rd is a private 4.3-acre retreat that offers flexible living space and a peaceful lifestyle that's hard to put a price tag on. Step inside, where the open-concept floor plan creates a seamless flow between the living room, dining area, and kitchen. A double-sided custom tile gas fireplace with a beautiful, stained wood mantel serves as the centerpiece. The spacious living areas are

  Aleisha Putman Synergy Realty Network, LLC

  206 Knott Rd, 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
• 

  

  /30

  Est $467,282

  Not Listed For Sale

  743 Hopkins Ln, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 2,457 Sq Ft
  • Built 1995

  743 Hopkins Ln, Winchester, TN 37398

  Last Sold Summary

  • 214 Days On Market

  Last Listing Agent Tyler Henley Franklin County Realty
• 

  

  /27

  $499,999

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

  512 Cline Ridge Rd, Winchester, TN 37398

  Fresh opportunity on Tims Ford Lake with improved pricing! If you have been looking for privacy, land, and lake life, this one deserves a second look. Set on a wooded lot with space for backyard bonfires, quiet evenings under the stars, and outdoor living, this property also includes private dock access approximately 400 yards from the home. Be on the water in minutes with no long idle zones and

  Jordan Crouch Benchmark Realty, LLC

  512 Cline Ridge Rd, 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
• 

  

  /29

  Est $410,750

  Not Listed For Sale

  140 Brandi Way, Winchester, TN 37398

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 1997

  140 Brandi Way, Winchester, TN 37398

  Last Sold Summary

  • 1 Day On Market

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

  

  /18

  $940,000

  • Land
  • 37.6 Acres
  • $25,000 per Acre

  0 Norwood Creek Rd, Winchester, TN 37398

  Beautiful acreage. Mountain views with a secluded feel. Creek runs through property. Ready for your dream house or mini farm. Owner has current survey. No perk site has been established so choose where you would want to build. All information deemed to be accurate please verify any important information.

  Benjamin Merrill Lynch Rigsby Realty & Auction, LLC

  0 Norwood Creek Rd, 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
• 

  

  /70

  Est $2,843,602

  Not Listed For Sale

  51 W Rockcrest Cir, Winchester, TN 37398

  • 3 Beds
  • 6.5 Baths
  • 7,901 Sq Ft
  • Built 2006

  51 W Rockcrest Cir, Winchester, TN 37398

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Marla Richardson Parks Compass
• 

  

  /40

  $545,000

  $44K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  18 Shady Cove Ln, Winchester, TN 37398

  Newer build in the quiet, wooded Hopkins Point Subdivision! The main level features 3 bedrooms, 2 full baths, an open layout, and a whole-home water purification system. The unfinished walkout basement provides clear upside to add square footage, or increase value. Enjoy a private, wooded setting with community boat ramp access to Tims Ford Lake, plus no HOA and no city taxes—making this a rare

  Jennifer Cummings SimpliHOM

  18 Shady Cove Ln, 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
• 

  

  /29

  Est $338,728

  Not Listed For Sale

  86 Royal Oak Dr, Winchester, TN 37398

  • 3 Beds
  • 3 Baths
  • 1,847 Sq Ft
  • Built 1977

  86 Royal Oak Dr, Winchester, TN 37398

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Ann Hoke Huffaker & Hoke Realty Partners
• 

  

  /55

  $489,900

  • 4 Beds
  • 4 Baths
  • 2,084 Sq Ft

  65 Duncan Ln, Winchester, TN 37398

  Rare opportunity to own a nearly new, high-end duplex built in 2023. The property features two beautifully finished 2-bedroom, 2-bath units, each offering 888 square feet of modern, efficient living space with an attached one-car garage. Both units are thoughtfully designed with open-concept layouts, upscale finishes, modern kitchens, and spacious bedrooms with private baths. One unit is

  Charlie Gonzales Southern Middle Realty

  65 Duncan Ln, Winchester, TN 37398

Showing Results 361 - 400, Page 10 of 18