Winchester, TN Homes

• 

  

  

  /80

  $1,450,000

  Sold Jul 01, 2026

  1305 Dripping Springs Rd, Winchester, TN 37398

  • 3 Beds
  • 4.5 Baths
  • 4,497 Sq Ft
  • Built 1975

  Last Sold Summary

  • 2% Below List Price
  • $322/SF
  • 7 Days On Market

  Current Estimated Value $1,429,061

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  1305 Dripping Springs Rd, Winchester, TN 37398
• 

  

  

  /44

  Est $387,157

  Not Listed For Sale

  176 Susie Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,961 Sq Ft
  • Built 1995

  176 Susie Dr, Winchester, TN 37398

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Pelatiah Prince Winton Auction & Realty Co.
• 

  

  

  /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
• 

  

  /2

  $247,000

  Sold Jul 15, 2026

  0 Kayak Way Unit 482, Winchester, TN 37398

  • Land
  • 11,761 Sq Ft
  • $914,815 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 3 Days On Market

  Last Listing Agent Felicia Wright Leading Edge Real Estate Group

  0 Kayak Way Unit 482, Winchester, TN 37398
• 

  

  

  /55

  Est $495,543

  Not Listed For Sale

  106 Crouch Ln, Winchester, TN 37398

  • 4 Beds
  • 3.5 Baths
  • 4,291 Sq Ft
  • Built 1900

  106 Crouch Ln, Winchester, TN 37398

  Last Sold Summary

  • 7 Days On Market

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

  

  /64

  $470,000

  $5K PRICE DROP

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

  309 2nd Ave NW, Winchester, TN 37398

  SELLER OFFERING OWNER FINANCING AT 5.75% — An ideal income-producing property just over a block from downtown Winchester, provides a rare opportunity for buyers seeking investment property in Tennessee with flexibility for different uses. Built in 1917, this historic, commercially zoned 5-bedroom, 2-bath residence includes approximately 3,922 sq ft on a .34-acre lot in the heart of Winchester.

  Robert Duncan eXp Realty

  309 2nd Ave NW, Winchester, TN 37398
• 

  

  /75

  $1,960,000

  Sold Jan 27, 2026

  97 Shady Cove Ln, Winchester, TN 37398

  • 2 Beds
  • 3.5 Baths
  • 3,410 Sq Ft
  • Built 1997

  Last Sold Summary

  • 7% Below List Price
  • $575/SF
  • 152 Days On Market

  Current Estimated Value $1,955,643

  Last Listing Agent Timothy Crabtree Benchmark Realty, LLC

  97 Shady Cove Ln, Winchester, TN 37398
• 

  

  /64

  Est $410,402

  Not Listed For Sale

  160 Old Huntsville Rd, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 2,640 Sq Ft
  • Built 1938

  160 Old Huntsville Rd, Winchester, TN 37398

  Last Sold Summary

  • 126 Days On Market

  Last Listing Agent Sharon Swafford Swaffords Property Shop
• 

  

  /31

  $499,000

  $46K PRICE DROP

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

  23 Skidmore Ln, Winchester, TN 37398

  All-brick home with stunning mountain views, a detached 3-car garage with bonus space above, and nearly an acre of level country living just minutes from Winchester. Situated on a beautiful corner lot just minutes from Winchester, this all-brick home offers over 2,200 square feet of living space with stunning countryside and mountain views. Featuring 3 bedrooms, 2.5 baths, a dedicated office, and

  Ashley Nelson Franklin County Realty

  23 Skidmore Ln, Winchester, TN 37398
• 

  

  /31

  $255,000

  Sold Apr 08, 2026

  406 Asia Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft
  • Built 1974

  Last Sold Summary

  • 22% Below List Price
  • $180/SF
  • 153 Days On Market

  Current Estimated Value $235,888

  Last Listing Agent Lashun Burks WEICHERT, REALTORS - The Andrews Group

  406 Asia Rd, Winchester, TN 37398
• 

  

  /44

  Est $725,720

  Not Listed For Sale

  64 Queens Cir, Winchester, TN 37398

  • 5 Beds
  • 4.5 Baths
  • 3,672 Sq Ft
  • Built 2008

  64 Queens Cir, Winchester, TN 37398

  Last Sold Summary

  • 227 Days On Market

  Last Listing Agent Leanne Bonning Benchmark Realty, LLC
• 

  

  /99

  $729,900

  $5K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 3,960 Sq Ft

  323 Ridgecrest Dr, Winchester, TN 37398

  BE A PART OF THE FRANKLIN HILLS COMMUNITY! Relax in this stunning 4BR/5BA home in sought after Franklin Hills subdivision, where timeless elegance meets contemporary convenience. Nestled minutes from Tims Ford Lake and the Winchester city park, this home offers unparalleled living, sophisticated design and impressive amenities. Enjoy the grandeur of the 18 foot ceilings in the LR, accented by

  Daryl Welch Freedom Realty Group

  323 Ridgecrest Dr, Winchester, TN 37398
• 

  

  /91

  $2,800,000

  Sold Aug 31, 2026

  323 Sunset Cove Ln, Winchester, TN 37398

  • 3 Beds
  • 4.5 Baths
  • 4,637 Sq Ft
  • Built 2024

  Last Sold Summary

  • 7% Below List Price
  • $604/SF
  • 23 Days On Market

  Last Listing Agent Justin Briggs Freedom Realty

  323 Sunset Cove Ln, Winchester, TN 37398
• 

  

  /49

  Est $731,374

  Not Listed For Sale

  469 Pickney Rd, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 3,147 Sq Ft
  • Built 2007

  469 Pickney Rd, Winchester, TN 37398

  Last Sold Summary

  • 19 Days On Market

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

  

  /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
• 

  

  /22

  $1,250,000

  Sold Mar 30, 2026

  517 Bluff Dr, Winchester, TN 37398

  • 2 Beds
  • 4 Baths
  • 3,384 Sq Ft
  • Built 1998

  Last Sold Summary

  • 5% Above List Price
  • $369/SF
  • 7 Days On Market

  Current Estimated Value $1,209,432

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

  517 Bluff Dr, Winchester, TN 37398
• 

  

  /40

  Est $732,384

  Not Listed For Sale

  612 Pickney Rd, Winchester, TN 37398

  • 4 Beds
  • 4 Baths
  • 4,331 Sq Ft
  • Built 2000

  612 Pickney Rd, Winchester, TN 37398

  Last Sold Summary

  • 187 Days On Market

  Last Listing Agent Leanne Bonning Benchmark Realty, LLC
• 

  

  /15

  $210,000

  $20K PRICE DROP

  • Land
  • 10,890 Sq Ft
  • $840,000 per Acre

  0 Kayak Way Unit 489, Winchester, TN 37398

  JUST REDUCED!!! 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

  Felicia Wright Leading Edge Real Estate Group

  0 Kayak Way Unit 489, Winchester, TN 37398
• 

  

  /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

  Current Estimated Value $501,467

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  332 Country Club Rd, Winchester, TN 37398
• 

  

  /33

  Est $320,000

  Not Listed For Sale

  93 Chase Cir, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,739 Sq Ft
  • Built 2003

  93 Chase Cir, Winchester, TN 37398

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Melissa Stewart Swaffords Property Shop
• 

  

  /64

  $449,900

  $47K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,160 Sq Ft

  103 Anderton Dr, Winchester, TN 37398

  Welcome to a Gem of a Townhome, Immaculate and Well-Kept by Original Owner. Located in Twin Creeks Village and Resort, a Gated Community on Tim's Ford Lake in Winchester, Tennessee. This Unique Townhome Boasts 5 Bedrooms and a Spacious Feel Throughout, with TWO Bedrooms and TWO Full Bathrooms on the Main Level! Extra Privacy and Space on this Lot, with a Beautiful Pond to the Side, with

  Tara Hays Benchmark Realty, LLC

  103 Anderton Dr, Winchester, TN 37398
• 

  

  /49

  $380,000

  Sold Mar 23, 2026

  657 Country Club Ln, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 2,101 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $181/SF
  • 6 Days On Market

  Current Estimated Value $391,676

  Last Listing Agent Sabrina Kimball Simple Real Estate - Keller Williams

  657 Country Club Ln, Winchester, TN 37398
• 

  

  /51

  Est $383,233

  Not Listed For Sale

  360 Chase Cir, Winchester, TN 37398

  • 2 Beds
  • 2.5 Baths
  • 2,959 Sq Ft
  • Built 2003

  360 Chase Cir, Winchester, TN 37398

  Last Sold Summary

  • 170 Days On Market

  Last Listing Agent Brandy Moore Benchmark Realty, LLC
• 

  /2

  $399,000

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,716 Sq Ft

  0 Edgefield Ct Unit 3592518, Winchester, TN 37398

  Maintenance-free living at its finest! Step into comfort, style, and convenience with this beautifully appointed townhome located in a desirable gated community. Inside, you'll find gorgeous granite countertops, custom cabinetry, stainless steel appliances, and luxury vinyl plank flooring that combine modern style with easy everyday living. A one-car garage provides added convenience and storage,

  Angela Miller John Smith Jr Realty and Auction LLC

  0 Edgefield Ct Unit 3592518, Winchester, TN 37398
• 

  

  /10

  $65,000

  Sold Jul 21, 2026

  5468 Old Tullahoma Rd, Winchester, TN 37398

  • Land
  • 41,382 Sq Ft
  • $68,421 per Acre

  Last Sold Summary

  • 19% Below List Price
  • 69 Days On Market

  Last Listing Agent Mandi Oakes Fridrich & Clark Realty

  5468 Old Tullahoma Rd, Winchester, TN 37398
• 

  

  /18

  Est $402,023

  Not Listed For Sale

  446 Favre Cir, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,959 Sq Ft
  • Built 2007

  446 Favre Cir, Winchester, TN 37398

  Last Sold Summary

  • 93 Days On Market

  Last Listing Agent Patsy Truslow Sewanee Realty
• 

  

  /21

  $574,900

  $40K PRICE DROP

  • Land
  • 1.13 Acres
  • $508,761 per Acre

  0 Dry Creek Ln Unit 3, Winchester, TN 37398

  Rare Lakefront Opportunity: Just Over an Acre of Private Paradise! Septic approved. TVA LARGE DOCK APPROVED!!!! Documentation is available in MLS.Discover the perfect canvas for your dream lake home on this exceptional 1.13-acre lot, beautifully situated in the desirable Dripping Springs area within Dry Creek Estates. Offering the ultimate combination of convenience and serenity, this

  Amy Wingo eXp Realty

  0 Dry Creek Ln Unit 3, Winchester, TN 37398
• 

  

  /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

  Current Estimated Value $327,309

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

  17 Strawberry Dr, Winchester, TN 37398
• 

  

  /19

  Est $369,641

  Not Listed For Sale

  76 Wood Bluff Rd, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft
  • Built 1992

  76 Wood Bluff Rd, Winchester, TN 37398

  Last Sold Summary

  • 214 Days On Market

  Last Listing Agent Patsy Truslow Sewanee Realty
• 

  

  /41

  $349,900

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,640 Sq Ft

  205 Houghton Dr, Winchester, TN 37398

  Welcome home to this spacious, all-brick ranch offering a versatile one-level floor plan, generous storage, and wonderful outdoor living space! With two primary suites located on opposite ends of the home, this layout offers exceptional privacy and flexibility for family, guests, or multigenerational living.The main living areas feature beautiful hardwood and tile flooring, two

  Danielle Wolff Holland Coldwell Banker Southern Realty

  205 Houghton Dr, Winchester, TN 37398
• 

  

  /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 Earin Smotherman Reliant Realty ERA Powered

  45 Hammock Ct, Winchester, TN 37398
• 

  

  /34

  Est $479,204

  Not Listed For Sale

  1487 S College St, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 3,187 Sq Ft
  • Built 1967

  1487 S College St, Winchester, TN 37398

  Last Sold Summary

  • 77 Days On Market

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

  

  /17

  $999,500

  $101K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 6,152 Sq Ft

  236 Tims Ford Dr, Winchester, TN 37398

  This fantastic large custom home is located upon entering picturesque Tims Ford State Park. This home offers endless opportunities for outdoor enthusiasts.Spend your weekends golfing,hiking,boating or cycling through stunning trails,or enjoy a day on or by the lake. This property is horse-friendly & ideal for those who love the outdoors. As you explore the nearby walking trails, enjoy wildlife

  Debbie Goodman Professional Realty

  236 Tims Ford Dr, Winchester, TN 37398
• 

  

  /3

  $112,000

  Sold Jul 31, 2026

  4 Anderton Dr, Winchester, TN 37398

  • Land
  • 2.13 Acres
  • $52,533 per Acre

  Last Sold Summary

  • 28% Below List Price
  • 385 Days On Market

  Last Listing Agent isaac zimmerle Benchmark Realty, LLC

  4 Anderton Dr, Winchester, TN 37398
• 

  

  /18

  Est $248,287

  Not Listed For Sale

  206 Edgewater Dr, Winchester, TN 37398

  • 2 Beds
  • 1 Bath
  • 1,372 Sq Ft
  • Built 1960

  206 Edgewater Dr, Winchester, TN 37398

  Last Sold Summary

  • 3 Days On Market

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

  

  /57

  $587,900

  $10K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 2,753 Sq Ft

  8 Latitude Dr, Winchester, TN 37398

  Beautiful, Like-New Home! Well Taken Care Of, Upgraded Finishes. Main Level Primary Bedroom with Private Bathroom, Double Vanities, Beautifully Tiled Shower, and Walk-in Closet. Second Bedroom is Also on The Main Level with Hallway Full Bathroom. Laundry Room has Tiled Floor. Living Room and Dining Room Feature Beautiful Wainscoting, Gas Fireplace, and Designer Light Fixtures. The Kitchen has A

  Tara Hays Benchmark Realty, LLC

  8 Latitude Dr, Winchester, TN 37398
• 

  

  /11

  $64,999

  Sold Aug 10, 2026

  0 Lookout Dr Unit 42, Winchester, TN 37398

  • Land
  • 12,196 Sq Ft
  • $232,139 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Alexia Cain Home and Farms Inc

  0 Lookout Dr Unit 42, Winchester, TN 37398
• 

  

  /44

  Est $701,801

  Not Listed For Sale

  337 Pickney Rd, Winchester, TN 37398

  • 4 Beds
  • 3 Baths
  • 3,497 Sq Ft
  • Built 2007

  337 Pickney Rd, Winchester, TN 37398

  Last Sold Summary

  • 5 Days On Market

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

  

  /23

  $89,900

  $15K PRICE DROP

  • Land
  • 0 Sq Ft

  0 Why Worry Ln Unit 255, Winchester, TN 37398

  REDUCED ! ! ! Come and check out this terrific value -- Lot 255 in beautiful Twin Creeks Village -- a great lot choice for your new lake home! This level lot is just beyond the gated entrance and is only a stone's throw to the newly constructed Pool #3. Whether you are looking to build your forever home or a family vacation home, this lot is in a great location. Amenities galore in TCV -- 3

  Shelia Lunsford Benchmark Realty, LLC

  0 Why Worry Ln Unit 255, Winchester, TN 37398
• 

  

  /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

  Current Estimated Value $227,186

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

  458 Woods Edge Rd, Winchester, TN 37398

Showing Results 401 - 440, Page 11 of 18