Winchester, TN Homes

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  /81

  $525,000 Sold Sep 22, 2025

  130 Golf Shores Dr, Winchester, TN 37398

  • 3 Beds
  • 4 Baths
  • 2,668 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Above List Price
  • $197/SF
  • 4 Days On Market

  Current Estimated Value $523,481

  Last Listing Agent Eberley Holloway Southern Middle Realty

  130 Golf Shores Dr, Winchester, TN 37398
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  /59

  Est $919,431 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,688 Sq Ft

  75 Bluff Dr, Winchester, TN 37398

  75 Bluff Dr, Winchester, TN 37398
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  /63

  $559,900

  • 4 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
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  /22

  $210,000 Sold Apr 29, 2025

  37 Lindbergh Ave, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1994

  Last Sold Summary

  • $190/SF
  • 12 Days On Market

  Current Estimated Value $207,839

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

  37 Lindbergh Ave, Winchester, TN 37398
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  /16

  Est $180,020 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 885 Sq Ft

  101 Highland St, Winchester, TN 37398

  101 Highland St, Winchester, TN 37398
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  /36

  $949,900

  • 5 Beds
  • 5 Baths
  • 4,748 Sq Ft

  105 Cannonball Ct, Winchester, TN 37398

  5BR /5BA Home located in a quiet cul de sac with a view of pond/water fountain. 3 Car Garage and lots of parking in the driveway. Short golf cart ride away from Twin Creeks Marina. Plenty of space for entertaining family and friends. The main floor has a spacious kitchen, large breakfast nook, formal dining, a den, large laundry room, Master Suite & 2 full baths. Kitchen has Kitchen-Aid

  Angela Privett Benchmark Realty, LLC

  105 Cannonball Ct, Winchester, TN 37398
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  /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

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  332 Country Club Rd, Winchester, TN 37398
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  /28

  Est $244,086 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,667 Sq Ft

  63 Lindbergh Ave, Winchester, TN 37398

  63 Lindbergh Ave, Winchester, TN 37398
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  /26

  $64,000

  • Land
  • 0.91 Acre
  • $70,330 per Acre

  0 Cooper Ln, Winchester, TN 37398

  New Price! Reduced! Beautiful! Just under an acre residential lot is partially cleared and partially wooded. 5 Minutes to Winchester City Park & Public Boat Ramp, 8 Minutes to Winchester Courthouse Square' shopping, theater, restaurants and more. Must See!

  Sharon Swafford Swaffords Property Shop

  0 Cooper Ln, Winchester, TN 37398
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  /27

  $574,900 Sold Mar 18, 2025

  884 Rowe Gap Rd, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,612 Sq Ft
  • Built 2025

  Last Sold Summary

  • $220/SF
  • 4 Days On Market

  Current Estimated Value $569,000

  Last Listing Agent Amy Mabry Mabry Realty, LLC

  884 Rowe Gap Rd, Winchester, TN 37398
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  /35

  Est $404,393 Not Listed For Sale

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

  95 Audobon Dr, Winchester, TN 37398

  95 Audobon Dr, Winchester, TN 37398
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  /35

  $575,000

  • 3 Beds
  • 3 Baths
  • 3,523 Sq Ft

  261 Franklin Heights Dr, Winchester, TN 37398

  Beautiful Custom Built Brick home in sought out neighborhood Franklin Hills. This gorgeous home located on a corner lot features 3 bedrooms with an office/study or work out room that is currently being used as a 4th bedroom. Two nice open Living Room/Media areas. Primary bedroom features has a double vanity, garden tub, shower and Large walk in closet. Kitchen features updated kitchen cabinets.

  Connie Wallace Century 21 Prestige Winchester

  261 Franklin Heights Dr, Winchester, TN 37398
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  /35

  $463,000 Sold Jan 27, 2025

  242 Pine Bluff Rd, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,417 Sq Ft
  • Built 2021

  Last Sold Summary

  • 3% Below List Price
  • $192/SF
  • 165 Days On Market

  Current Estimated Value $429,510

  Last Listing Agent Chelsea Greenway Winton Auction & Realty Co.

  242 Pine Bluff Rd, Winchester, TN 37398
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  /10

  Est $263,170 Not Listed For Sale

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

  140 Bel Aire Dr, Winchester, TN 37398

  140 Bel Aire Dr, Winchester, TN 37398
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  /70

  $3,800,000

  • 6 Beds
  • 8 Baths
  • 8,002 Sq Ft

  1657 Boswell Rd, Winchester, TN 37398

  HIGHEST GROSSING RENTAL ON TIM'S FORD LAKE!!! Welcome to your stunning dream retreat on 14 acres on a private cove of Tims Ford Lake. This magnificent turnkey 8,000+ sqft estate comes furnished and boasts a 5 bed, 5.5 bath with luxurious accommodations and ample space for 20+ guests. The home features a modern commercial grade kitchen, endless windows for great natural light, a game room, a

  Davey Hackett Parks Compass

  1657 Boswell Rd, Winchester, TN 37398
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  /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

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

  17 Strawberry Dr, Winchester, TN 37398
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  /24

  Est $177,603 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft

  331 Pine Bluff Rd, Winchester, TN 37398

  331 Pine Bluff Rd, Winchester, TN 37398
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  /51

  $869,900

  • 3 Beds
  • 2.5 Baths
  • 2,236 Sq Ft

  155 Cypress Point Dr, Winchester, TN 37398

  Welcome to your custom built dream home on the water, with a community boat dock plus a boat slip. Primary suite on the main level with large walk-in closet and entry door to the patio. Thoughtfully designed space with 2x6 construction and a large partially finished bonus room. Luxury vinyl plank and tile flooring. Covered porch, screened in porch and a large patio. Storage under the patio for

  Thomas Williams Crye-Leike, Inc., REALTORS

  155 Cypress Point Dr, Winchester, TN 37398
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  /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 Grey Smotherman Reliant Realty ERA Powered

  45 Hammock Ct, Winchester, TN 37398
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  /35

  Est $310,400 Not Listed For Sale

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

  280 Susie Dr, Winchester, TN 37398

  280 Susie Dr, Winchester, TN 37398
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  /3

  $69,900

  • Land
  • 0.15 Acre
  • $466,000 per Acre

  0 Deer Valley Cir Unit RTC2980805, Winchester, TN 37398

  Welcome to your next opportunity in this brand-new, gated 55+ community designed for comfort, convenience, and connection! Choose your perfect spot and create a home that fits your lifestyle. This thoughtfully planned neighborhood will include a beautifully appointed clubhouse, swimming pool, fitness center, and a dedicated dog park—perfect for active, social living. Don't miss this opportunity-

  Ashley Lynch Lynch Rigsby Realty & Auction, LLC

  0 Deer Valley Cir Unit RTC2980805, Winchester, TN 37398
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  /24

  $305,000 Sold Jan 31, 2025

  581 Rowe Gap Rd, Winchester, TN 37398

  • 4 Beds
  • 2 Baths
  • 2,341 Sq Ft
  • Built 1918

  Last Sold Summary

  • 13% Below List Price
  • $130/SF
  • 43 Days On Market

  Current Estimated Value $343,102

  Last Listing Agent Christopher Smith Synergy Realty Network, LLC

  581 Rowe Gap Rd, Winchester, TN 37398
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  /4

  Est $215,544 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,284 Sq Ft

  1309 Old Cowan Rd, Winchester, TN 37398

  1309 Old Cowan Rd, Winchester, TN 37398
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  /13

  $230,000

  • Land
  • 0.25 Acre
  • $920,000 per Acre

  0 Kayak Way Unit RTC3033545, Winchester, TN 37398

  JUST LISTED!!! LAKE VIEW LOT with water access! Don’t miss this highly sought-after lake view lot in the Twin Creeks Development. This is an excellent opportunity to build your dream home in a resort-style, golf cart friendly community. This lot is just a short ride to the marina, beach, hiking trails, fishing ponds, cabins, and campground. HOA includes mowing, access to 3 swimming pools, and use

  Felicia Wright Leading Edge Real Estate Group

  0 Kayak Way Unit RTC3033545, Winchester, TN 37398
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  /30

  $325,000 Sold Apr 16, 2025

  57 Sam Houston Place, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,505 Sq Ft
  • Built 2012

  Last Sold Summary

  • $216/SF
  • 43 Days On Market

  Current Estimated Value $327,334

  Last Listing Agent Guy Fain EXP Realty LLC

  

  57 Sam Houston Place, Winchester, TN 37398
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  /12

  Est $314,848 Not Listed For Sale

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

  152 Brookfield Cir, Winchester, TN 37398

  152 Brookfield Cir, Winchester, TN 37398
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  /31

  $280,000

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  406 Asia Rd, Winchester, TN 37398

  Well-kept estate property in Winchester's Asia Community just minutes from Tims Ford Lake! This home is in a quiet, country setting with all the charm not found in new builds. Home features 3 bedrooms and 2 full baths. Main bathroom with ceramic tile. Cozy den is perfect for relaxing with family and friends. The heart of this home is the kitchen with beautiful custom cabinets and hardwood

  Lashun Burks WEICHERT, REALTORS - The Andrews Group

  406 Asia Rd, Winchester, TN 37398
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  /3

  $77,000 Sold Mar 27, 2025

  0 Old Tullahoma Rd, Winchester, TN 37398

  • Land
  • 1.38 Acres
  • $55,797 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 8 Days On Market

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

  0 Old Tullahoma Rd, Winchester, TN 37398
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  /29

  Est $410,384 Not Listed For Sale

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

  140 Brandi Way, Winchester, TN 37398

  140 Brandi Way, Winchester, TN 37398
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  /30

  $289,900

  • 4 Beds
  • 2 Baths
  • 2,560 Sq Ft

  4025 David Crockett Pkwy W, Winchester, TN 37398

  Welcome to this unique piece of property just minutes from town. Home sits on a generous lot with lovely mature shade trees and flowers. Inside you will find 3bdr/1bath in the main home and in the attached mother-in law suite you will find an additional bedroom and bath. Mother-in law suite also features a kitchen and living room which can be accessed from the outside for great rental

  Angela Miller John Smith Jr Realty and Auction LLC

  4025 David Crockett Pkwy W, Winchester, TN 37398
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  /34

  $310,000 Sold Sep 23, 2025

  431 Haddon Ln, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft
  • Built 1900

  Last Sold Summary

  • 9% Below List Price
  • $175/SF
  • 37 Days On Market

  Current Estimated Value $311,560

  Last Listing Agent Dustyn Reed United Real Estate Middle Tennessee

  431 Haddon Ln, Winchester, TN 37398
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  /68

  Est $1,546,224 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,146 Sq Ft

  231 Beech Hill Dr, Winchester, TN 37398

  231 Beech Hill Dr, Winchester, TN 37398
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  /48

  $699,999

  • 3 Beds
  • 3.5 Baths
  • 2,841 Sq Ft

  64 Windjammer Ct, Winchester, TN 37398

  Experience refined lake living in this newly built 3 bed, 3.5 bath home in the prestigious Twin Creeks community on Tim’s Ford Lake. Offering 2,800 sqft of thoughtfully designed space, this home includes a private office, spacious bonus room, and screened-in porch. Interior highlights feature custom cabinetry, designer tile in bathrooms, detailed trim accents, and a statement fireplace in the

  Grey Smotherman Reliant Realty ERA Powered

  64 Windjammer Ct, Winchester, TN 37398
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  /54

  $710,000 Sold Apr 15, 2025

  814 River Watch Way, Winchester, TN 37398

  • 3 Beds
  • 3.5 Baths
  • 2,650 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $268/SF
  • 15 Days On Market

  Last Listing Agent Tara Hays Benchmark Realty, LLC

  814 River Watch Way, Winchester, TN 37398
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  /43

  Est $533,997 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,815 Sq Ft

  178 Sugar Leaf Cir, Winchester, TN 37398

  178 Sugar Leaf Cir, Winchester, TN 37398
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  /59

  $145,000

  • Land
  • 0.26 Acre
  • $557,692 per Acre

  0 Wakeboard Way Unit RTC2941097, Winchester, TN 37398

  Discover the perfect canvas for your lakeside dream home! This prime lot on Wakeboard Way is ideally located just steps from the gated golf cart entrance to Twin Creeks Marina & Drafts & Watercrafts restaurant. Situated in one of the most sought-after communities on Tims Ford Lake, Twin Creeks Village offers resort-style amenities including a clubhouse, heated pools, event barn, putting green,

  Charlie Gonzales Southern Middle Realty

  0 Wakeboard Way Unit RTC2941097, Winchester, TN 37398
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  /14

  $500,000 Sold Apr 18, 2025

  214 8th Ave SW, Winchester, TN 37398

  • 9 Beds
  • 6 Baths
  • 3,366 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $149/SF
  • 183 Days On Market

  Current Estimated Value $277,596

  Last Listing Agent Daryl Welch Harton Realty Company

  214 8th Ave SW, Winchester, TN 37398
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  /29

  Est $351,895 Not Listed For Sale

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

  86 Royal Oak Dr, Winchester, TN 37398

  86 Royal Oak Dr, Winchester, TN 37398
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  /37

  $299,000

  • 3 Beds
  • 2 Baths
  • 2,053 Sq Ft

  209 Franklin Park, Winchester, TN 37398

  This totally renovated brick home has been beautifully and thoughtfully done. Offering so many updates such as new roof, new windows, new doors & trim work, refinished hardwood floors, new LVP/LVT, updated 200-amp braker panel, all new plumbing, granite counter tops, and more. When you enter through the backdoor you are welcomed into a beautifully finished sunroom or rec room that can be used for

  Chelsea Greenway Winton Auction & Realty Co.

  209 Franklin Park, Winchester, TN 37398
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  /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

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

  458 Woods Edge Rd, Winchester, TN 37398

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