Winchester, TN Homes

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  $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 $792,302

  Last Listing Agent Rachel Ferrell Southern Middle Realty

  190 Cascade Dr, Winchester, TN 37398
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  Est $280,225 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft

  106 Hillcrest Dr, Winchester, TN 37398

  106 Hillcrest Dr, Winchester, TN 37398
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  $543,900

  • 4 Beds
  • 2 Baths
  • 1,925 Sq Ft

  290 Maple Bend Rd, Winchester, TN 37398

  Nearly new custom home on acreage in the highly desirable Maple Bend / Tims Ford Lake area. Built in 2022, this brick and Hardie residence offers a bright, open-concept layout with upscale finishes and no HOA. The spacious living room features luxury vinyl plank flooring, crown molding, recessed lighting, and a beautiful fireplace with a custom wood mantel and built-in shelving. An oversized

  Charlie Gonzales Southern Middle Realty

  290 Maple Bend Rd, Winchester, TN 37398
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  $175,000 Sold May 28, 2025

  802 Old Cowan Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2004

  Last Sold Summary

  • 9% Above List Price
  • $125/SF
  • 3 Days On Market

  Last Listing Agent Kisha Sanders Elam Real Estate

  802 Old Cowan Rd, Winchester, TN 37398
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  /24

  Est $194,827 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  406 7th Ave NW, Winchester, TN 37398

  406 7th Ave NW, Winchester, TN 37398
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  $399,900 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,208 Sq Ft

  44 Rocky Hollow Dr, Winchester, TN 37398

  Check out this delightful home in the coveted Hopkins Point subdivision with access to Tims Ford Lake via a private neighborhood boat ramp! A spacious interior provides 3 bedrooms/3 baths, an office space (currently used as an additional bedroom!) and a finished basement, perfect for movie/game nights, etc. Or, kick back and relax to the sounds of nature on the large screened in deck. In addition

  Timothy Crabtree Benchmark Realty, LLC

  44 Rocky Hollow Dr, Winchester, TN 37398
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  /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

  Last Listing Agent Sharon Swafford Swaffords Property Shop

  136 Bel Aire Dr, Winchester, TN 37398
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  /24

  Est $182,505 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 783 Sq Ft

  1401 Old Cowan Rd, Winchester, TN 37398

  1401 Old Cowan Rd, Winchester, TN 37398
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  $305,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  383 Strawberry Dr, Winchester, TN 37398

  Welcome to this well-maintained, move in ready, 3 bedroom, 2 full bath home situated on a full one-acre lot, offering space, privacy, and outdoor enjoyment. The fully fenced backyard is perfect for entertaining and everyday living, featuring a swimming pool, fire pit, and play set. Enjoy relaxing or hosting gatherings on the covered concrete patio, ideal for year-round use. There is a 50 amp

  Aubrey Layne Century 21 Coffee County Realty & Auction

  383 Strawberry 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
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  /47

  Est $408,147 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,932 Sq Ft

  371 Chase Cir, Winchester, TN 37398

  371 Chase Cir, Winchester, TN 37398
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  $363,899

  • 3 Beds
  • 1.5 Baths
  • 1,812 Sq Ft

  1445 Georgia Crossing Rd, Winchester, TN 37398

  This stunning Franklin County, Tennessee, country home, originally built in 1912, has undergone a complete modernization while retaining its rustic 1900s charm! The exterior boasts new windows, updated trim, and a new front door, while the interior has been virtually gutted and completely redone with a new HVAC system, flooring, updated ceiling heights, and beautiful wooden staircase accents.

  Brian Whitt Arrowhead Land Company

  1445 Georgia Crossing Rd, Winchester, TN 37398
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  $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

  Last Listing Agent Rachel Ferrell Southern Middle Realty

  190 Cheyenne Ave, Winchester, TN 37398
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  /30

  Est $240,391 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,700 Sq Ft

  1390 Water Tank Rd, Winchester, TN 37398

  1390 Water Tank Rd, Winchester, TN 37398
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  $1,650,000

  • 3 Beds
  • 2 Baths
  • 2,900 Sq Ft

  220 Deer View Ln, Winchester, TN 37398

  This stunning Franklin County, Tennessee, farm offers a pristine rural setting for those seeking a beautiful 3 bedroom, 2 bathroom home with acreage! The property includes +/- 50 acres of highly productive tillable land, yielding exceptional row crops, alongside rolling pastures, barns, and gorgeous front porch views. The updated home provides ample space for a growing family or future expansion.

  Brian Whitt Arrowhead Land Company

  220 Deer View Ln, Winchester, TN 37398
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  /3

  $40,000 Sold Jun 20, 2025

  0 Old Tullahoma Rd Unit RTC2775157, Winchester, TN 37398

  • Land
  • 0.63 Acre
  • $63,492 per Acre

  Last Sold Summary

  • 38% Below List Price
  • 142 Days On Market

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

  0 Old Tullahoma Rd Unit RTC2775157, Winchester, TN 37398
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  /44

  Est $301,334 Not Listed For Sale

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

  117 Dogwood Ln, Winchester, TN 37398

  117 Dogwood Ln, Winchester, TN 37398
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  $649,900

  • 4 Beds
  • 3.5 Baths
  • 2,680 Sq Ft

  60 Lake Life Ct, Winchester, TN 37398

  This 4 bedroom, 3.5 bath home with loft area works beautifully as a primary residence or as your serene vacation retreat. The open floor plan downstairs is filled with natural light, featuring a vaulted living room ceiling, gas fireplace and windows galore--perfect for gathering after a day on the lake. Beautiful wood and tile flooring make this home a standout! TWO large primary suites, one on

  Shelia Lunsford Benchmark Realty, LLC

  60 Lake Life Ct, Winchester, TN 37398
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  $417,000 Sold Apr 07, 2025

  83 Holly Dr, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,320 Sq Ft
  • Built 1991

  Last Sold Summary

  • $180/SF
  • 0 Days On Market

  Current Estimated Value $420,880

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

  83 Holly Dr, Winchester, TN 37398
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  Est $469,492 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,518 Sq Ft

  165 Maple Bend Ln, Winchester, TN 37398

  165 Maple Bend Ln, Winchester, TN 37398
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  $549,900

  • 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
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  /45

  $764,900 Sold Jun 23, 2025

  467 Wildwood Trace, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 1,998 Sq Ft
  • Built 2019

  Last Sold Summary

  • $383/SF
  • 3 Days On Market

  Current Estimated Value $777,230

  Last Listing Agent Donna Mason Botsko Properties, Inc.

  467 Wildwood Trace, Winchester, TN 37398
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  /30

  Est $399,396 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,942 Sq Ft

  106 Prince Place, Winchester, TN 37398

  106 Prince Place, Winchester, TN 37398
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  $429,900 New Construction

  • 4 Beds
  • 2 Baths
  • 2,094 Sq Ft

  52 Wiseman Ln, Winchester, TN 37398

  This brand-new vinyl-siding home offers 4 bedrooms and 2 full baths with a thoughtfully designed open floor plan. Luxury vinyl plank flooring flows throughout the main living areas, while the bathrooms and utility room feature durable tile flooring. The spacious kitchen showcases custom cabinetry, granite countertops, and an open layout that’s perfect for entertaining or everyday living. The

  Lisa Curl Better Homes & Gardens Real Estate Heritage Group

  52 Wiseman Ln, Winchester, TN 37398
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  /52

  $429,900 Sold Jun 20, 2025

  8343 Lynchburg Rd, Winchester, TN 37398

  • 4 Beds
  • 2 Baths
  • 2,297 Sq Ft
  • Built 2024

  Last Sold Summary

  • 7% Below List Price
  • $187/SF
  • 181 Days On Market

  Last Listing Agent Lisa Curl Better Homes & Gardens Real Estate Heritage Group

  8343 Lynchburg Rd, Winchester, TN 37398
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  /34

  Est $450,547 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,230 Sq Ft

  261 Dry Creek Ln, Winchester, TN 37398

  261 Dry Creek Ln, Winchester, TN 37398
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  $485,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,543 Sq Ft

  201 Lookout Dr, Winchester, TN 37398

  Special 4.99% Fixed Interest Rate Offer! Welcome to this meticulously designed new home! The residence features three spacious bedrooms and two bathrooms, along with a supplemental room with a half bath. It includes upscale features like top-of-the-line stainless steel appliances, custom-built expansive wardrobes, and an exquisite coffered ceiling in the main living area. Through precise

  Mena Shaker Dream Homes Realty

  201 Lookout Dr, Winchester, TN 37398
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  $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

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

  105 Twilight Dr, Winchester, TN 37398
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  Est $246,990 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,736 Sq Ft

  1338 Blue Spring Rd, Decherd, TN 37324

  1338 Blue Spring Rd, Decherd, TN 37324
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  $499,900

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

  148 Brandi Way, Winchester, TN 37398

  Welcome to your Dream Home in the heart of Winchester's highly sought-after Winchester Village on Tims Ford Lake!Discover this Gorgeous Home that has been meticulously maintained with Amenities that include access to Community Lake Lot and Dock as this home is across the street from Tims Ford Lake with a Lake View. This home is ready to impress the moment you walk in. Please ask if the

  Elizabeth Padgett Peck Realty Group, LLC

  148 Brandi Way, Winchester, TN 37398
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  /22

  $209,900 Sold Mar 26, 2025

  35 Pittenger Cir, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Above List Price
  • $208/SF
  • 117 Days On Market

  Last Listing Agent Daryl Welch Freedom Realty Group

  35 Pittenger Cir, Winchester, TN 37398
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  Est $1,081,611 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,160 Sq Ft

  363 Wildwood Cir, Winchester, TN 37398

  363 Wildwood Cir, Winchester, TN 37398
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  $575,000

  • 4 Beds
  • 4 Baths
  • 2,749 Sq Ft

  54 Foyer Dr, Winchester, TN 37398

  Charming 4-Bedroom Brick Home in Bell Acres!REDUCED! BUYER CONCESSIONS OF UP TO $10,000! Don’t miss this opportunity to live in lovely Bell Acres! This well-maintained brick home offers 4 bedrooms, 2 full baths, and 2 half baths. Features include wide hallways, a spacious central living/family room, and a large family kitchen perfect for gatherings. Enjoy the cozy gas fireplace and a

  Dawn Parrish Leading Edge Real Estate Group

  54 Foyer Dr, Winchester, TN 37398
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  /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
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  /19

  Est $319,204 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,616 Sq Ft

  221 Ridgefield Cir, Winchester, TN 37398

  221 Ridgefield Cir, Winchester, TN 37398
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  $669,000

  • 4 Beds
  • 3 Baths
  • 2,592 Sq Ft

  65 Pontoon Place, Winchester, TN 37398

  Discover refined lake living in this exquisite, gated community, where peace and luxury come together. Selling Fully Furnished!! Residents here enjoy an impressive list of amenities, including a full-service marina, clubhouse, and several pools. Low maintenance with a HOA that takes care of your lawn and all amenities. This stunning home is crafted with timeless detail featuring both an indoor

  Angela Miller John Smith Jr Realty and Auction LLC

  65 Pontoon Place, Winchester, TN 37398
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  $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
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  Est $419,366 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,603 Sq Ft

  47 Long View Dr, Winchester, TN 37398

  47 Long View Dr, Winchester, TN 37398
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  $465,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,543 Sq Ft

  67 Summerset Dr, Winchester, TN 37398

  Welcome to this beautifully crafted new home featuring three spacious bedrooms and two full bathrooms, plus a versatile bonus room with its own half bath. Enjoy top-of-the-line stainless steel appliances, custom-built oversized wardrobes, and an elegant coffered ceiling in the main living area. Built with premium materials and exceptional craftsmanship, this home blends luxury and sophistication

  Mena Shaker Dream Homes Realty

  67 Summerset Dr, Winchester, TN 37398
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  /40

  $765,000 Sold May 02, 2025

  1000 N Jefferson St, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 1,796 Sq Ft
  • Built 2021

  Last Sold Summary

  • 1% Below List Price
  • $426/SF
  • 33 Days On Market

  Current Estimated Value $739,076

  Last Listing Agent Gary Aadnes 1st Choice REALTOR

  1000 N Jefferson St, Winchester, TN 37398

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