Winchester, TN Homes

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  /53

  $299,900

  • 4 Beds
  • 1.5 Baths
  • 1,923 Sq Ft

  128 Bel Aire Dr, Winchester, TN 37398

  Welcome to 128 Bel Aire Dr — where modern updates, functional space, and an unbeatable location come together! This beautifully updated 4-bedroom, 1.5-bath home offers just under 2,000 square feet of comfortable living space. Inside, you’ll find brand new LVP flooring, giving the home a fresh, modern feel from the moment you walk in. Enjoy the flexibility of multiple living areas with both a

  Jessica London Southern Middle Realty

  128 Bel Aire Dr, Winchester, TN 37398
• 

  

  

  /35

  $535,000

  Sold Feb 17, 2026

  261 Franklin Heights Dr, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 3,523 Sq Ft
  • Built 2005

  Last Sold Summary

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

  Current Estimated Value $571,650

  Last Listing Agent Connie Wallace Century 21 Coffee County Realty & Auction

  261 Franklin Heights Dr, Winchester, TN 37398
• 

  

  

  /41

  Est $315,940

  Not Listed For Sale

  1147 Holders Cove Rd, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 1,642 Sq Ft
  • Built 1963

  1147 Holders Cove Rd, Winchester, TN 37398

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.
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  /16

  $794,500

  • 4 Beds
  • 3.5 Baths
  • 3,165 Sq Ft

  0 Ridgecrest Dr Unit RTC3220663, Winchester, TN 37398

  Come Home to Franklin Hills where you have all bedrooms on the main floor, a spacious bonus room over the 26x26 side load garage and a tree lined back yard with lots of privacy. Exterior of home will be 85 % Brick with Cement Fiber Board accents. The expansive foyer leads you directly into the great room with 12ft ceilings All other rooms will have 10 ft ceilings with 8 ft interior and exterior

  Angela Privett Benchmark Realty, LLC

  0 Ridgecrest Dr Unit RTC3220663, Winchester, TN 37398
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  /53

  $418,000

  Sold Jul 23, 2026

  123 Lookout Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,869 Sq Ft
  • Built 2026

  Last Sold Summary

  • $224/SF
  • 21 Days On Market

  Last Listing Agent Sandra Ayad Keller Williams Realty Mt. Juliet

  123 Lookout Dr, Winchester, TN 37398
• 

  

  /42

  Est $548,622

  Not Listed For Sale

  614 Country Club Rd, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 3,330 Sq Ft
  • Built 2006

  614 Country Club Rd, Winchester, TN 37398

  Last Sold Summary

  • 65 Days On Market

  Last Listing Agent Melissa Stewart Swaffords Property Shop
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  /48

  $599,900

  $30K PRICE DROP

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

  229 Ridgecrest Dr, Winchester, TN 37398

  Beautifully remodeled and truly move-in ready, this exceptional 2,815 sq. ft. one-level home is located in the highly desirable Franklin Hills subdivision, one of Winchester’s most established and sought-after neighborhoods. Situated in the newer rear section of the subdivision on a quiet dead-end street with no through traffic, this home offers both privacy and convenience, just minutes from

  Trent Poteat Realty Executives Associates

  229 Ridgecrest Dr, Winchester, TN 37398
• 

  

  /4

  $200,000

  Sold Sep 17, 2025

  0 Rocky Hollow Dr Unit RTC2739750, Winchester, TN 37398

  • Land
  • 1.58 Acres
  • $126,582 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 346 Days On Market

  Last Listing Agent Sam Hatfield Sam Hatfield Realty, Inc.

  0 Rocky Hollow Dr Unit RTC2739750, Winchester, TN 37398
• 

  

  /29

  Est $259,508

  Not Listed For Sale

  202 8th Ave SE, Winchester, TN 37398

  • 3 Beds
  • 1.5 Baths
  • 1,736 Sq Ft
  • Built 1957

  202 8th Ave SE, Winchester, TN 37398

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Ashley Lynch Lynch Rigsby Realty & Auction, LLC
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  /40

  $320,000

  $80K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  667 Maple Bend Rd, Winchester, TN 37398

  Close to the Fairview Boat Ramp.Fantastic 3.5 acres with mature trees, abundant wildlife, and privacy. Property extends 75 feet into woods. Room for a Garden or a Mini Farm Home is a 2 bedroom 1.5 half baths. Original Septic Permit is for a 3 Bedroom home. Room to Expand. New Roof and HVAC. 30x30 Detached Garage/shop with Wood Burning Stove or use the Propane Heater. 2 Metal Sheds for Storage.

  Pam Ford Benchmark Realty, LLC

  667 Maple Bend Rd, Winchester, TN 37398
• 

  

  /41

  $360,000

  Sold Oct 23, 2025

  1106 Old Cowan Rd, Winchester, TN 37398

  • 2,052 Sq Ft
  • Built 2022

  Last Sold Summary

  • 6% Below List Price
  • $175/SF
  • 18 Days On Market

  Current Estimated Value $263,344

  Last Listing Agent Amy Mullins Benchmark Realty LLC

  

  1106 Old Cowan Rd, Winchester, TN 37398
• 

  

  /43

  Est $378,627

  Not Listed For Sale

  112 8th Ave SE, Winchester, TN 37398

  • 5 Beds
  • 3 Baths
  • 2,837 Sq Ft
  • Built 1952

  112 8th Ave SE, Winchester, TN 37398

  Last Sold Summary

  • 153 Days On Market

  Last Listing Agent Melissa Stewart Swaffords Property Shop
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  /36

  $330,000

  $9K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,898 Sq Ft

  135 Chickamauga Trail, Winchester, TN 37398

  This beautiful 3-bedroom, 2 bath all brick home was designed with comfort, style, and everyday living in mind. From the moment you step inside, you'll love the inviting open-concept floorplan that creates the perfect space for gathering with family and friends. The thoughtfully designed split-bedroom layout offers added privacy, with the spacious primary suite tucked away from the secondary

  Angela Miller John Smith Jr Realty and Auction LLC

  135 Chickamauga Trail, Winchester, TN 37398
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  /29

  $376,000

  Sold Aug 13, 2025

  8405 Lynchburg Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,963 Sq Ft
  • Built 2024

  Last Sold Summary

  • 6% Below List Price
  • $192/SF
  • 232 Days On Market

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

  8405 Lynchburg Rd, Winchester, TN 37398
• 

  

  /14

  Est $354,615

  Not Listed For Sale

  108 8th Ave SE, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 3,330 Sq Ft
  • Built 1942

  108 8th Ave SE, Winchester, TN 37398

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Lora Pratt-Umbarger Better Homes & Gardens Real Estate Heritage Group
• 

  

  /14

  $144,900

  • Land
  • 21,344 Sq Ft
  • $295,714 per Acre

  0 Cannonball Ct Unit 187, Winchester, TN 37398

  Come build your dream home on this large lot in the Twin Creeks Community. Whether you live here year round or get away here on weekends, you can build to suit what you are looking for. Amenities include Marina with Boat Slips Rental, Restaurant with Water Front Dining, Guest Rental Cottages, Club house, Three Swimming Pools, Tennis, RV Campground, Sandy Beach with Boat Launch, Event Pavillion,

  Connie Wallace Century 21 Coffee County Realty & Auction

  0 Cannonball Ct Unit 187, Winchester, TN 37398
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  /48

  $699,999

  Sold May 14, 2026

  64 Windjammer Ct, Winchester, TN 37398

  • 3 Beds
  • 3.5 Baths
  • 2,841 Sq Ft
  • Built 2025

  Last Sold Summary

  • $246/SF
  • 0 Days On Market

  Last Listing Agent Grey Smotherman Reliant Realty ERA Powered

  64 Windjammer Ct, Winchester, TN 37398
• 

  

  /10

  Est $201,661

  Not Listed For Sale

  105 7th Ave SW, Winchester, TN 37398

  • 3 Beds
  • 1 Bath
  • 1,216 Sq Ft
  • Built 1958

  105 7th Ave SW, Winchester, TN 37398

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Aleisha Putman Synergy Realty Network, LLC
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  /36

  $325,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft

  1563 Paynes Church Rd, Winchester, TN 37398

  **Move in for only $99 AND a fixed rate as low as 5.5%**** BRAND NEW! ONE LEVEL, 3BD | 2BTH home LVP flooring throughout, NO CARPET OR STAIRS! ideal for easy maintenance! The kitchen features custom cabinetry, and SS kitchen appliances with brush nickel finishes. Open Concept layout & split bedroom floorplan- providing added privacy to the primary suite. This large yard offers plenty of space to

  Kasidy Lowe Compass Tennessee, LLC

  1563 Paynes Church Rd, Winchester, TN 37398
• 

  

  /22

  $168,000

  Sold Feb 13, 2026

  7010 Lynchburg Rd, Winchester, TN 37398

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 2004

  Last Sold Summary

  • 11% Below List Price
  • $88/SF
  • 8 Days On Market

  Last Listing Agent Daniel Prince John Smith Jr Realty and Auction LLC

  7010 Lynchburg Rd, Winchester, TN 37398
• 

  

  /40

  Est $396,990

  Not Listed For Sale

  400 S High St, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 2,770 Sq Ft
  • Built 1908

  400 S High St, Winchester, TN 37398

  Last Sold Summary

  • 50 Days On Market

  Last Listing Agent Amanda Lynch WEICHERT, REALTORS Joe Orr & Associates
• 

  

  /49

  $369,900

  • 3 Beds
  • 1.5 Baths
  • 1,508 Sq Ft

  1111 Holders Cove Rd, Winchester, TN 37398

  **Double lot with large shop** This beautiful, well-maintained brick home is convenient to everywhere - less than 1.5 miles from downtown Winchester - a mile from the Country Club -1.2 miles from the Hospital and 2 miles from Food City! It's perfectly positioned on a desirable corner lot and includes a second lot as well! Offering 3 bedrooms and 1.5 baths, this home combines timeless charm with

  Sean Crabtree Blue Door Realty Group

  1111 Holders Cove Rd, Winchester, TN 37398
• 

  

  /62

  $740,000

  Sold Oct 03, 2025

  163 Wakeboard Way, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 2,856 Sq Ft
  • Built 2022

  Last Sold Summary

  • 1% Below List Price
  • $259/SF
  • 10 Days On Market

  Current Estimated Value $676,266

  Last Listing Agent Andrew (Andy) McInturff Zach Taylor Real Estate

  163 Wakeboard Way, Winchester, TN 37398
• 

  

  /24

  Est $310,625

  Not Listed For Sale

  581 Rowe Gap Rd, Winchester, TN 37398

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

  581 Rowe Gap Rd, Winchester, TN 37398

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Christopher Smith Synergy Realty Network, LLC
• 

  

  /40

  $374,900

  • 3 Beds
  • 2 Baths
  • 1,657 Sq Ft

  95 Luttrell Dr, Winchester, TN 37398

  Beautifully maintained 3-bedroom, 2-bath home offering a spacious split-bedroom, open-concept floor plan with custom kitchen cabinetry, abundant storage, and an inviting living area. The primary suite features a tray ceiling, dual walk-in closets, and a private bath. Relax in the new two-person hot tub (which conveys) while enjoying beautiful views of Tims Ford Lake. A unique bonus is the vacant

  Thomas Ore Winton Auction & Realty Co.

  95 Luttrell Dr, Winchester, TN 37398
• 

  

  /16

  $275,000

  Sold Jan 10, 2026

  132 Highland Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,466 Sq Ft
  • Built 1953

  Last Sold Summary

  • 2% Below List Price
  • $188/SF
  • 74 Days On Market

  Current Estimated Value $277,652

  Last Listing Agent Daniel Demers Sell Your Home Services, LLC

  132 Highland Dr, Winchester, TN 37398
• 

  

  /26

  Est $228,439

  Not Listed For Sale

  117 Riley Ln, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,096 Sq Ft
  • Built 1997

  117 Riley Ln, Winchester, TN 37398

  Last Sold Summary

  • 1 Day On Market

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

  

  /14

  $57,000

  $5K PRICE DROP

  • Land
  • 0 Sq Ft

  0 Dry Fork Unit 62, Winchester, TN 37398

  Build your dream home in the exclusive, gated Twin Creeks Village on Tim’s Ford Lake—ideally located within walking distance to one of the community’s resort-style pools and pool house. This prime homesite places you in the heart of one of Winchester’s most sought-after lake communities, offering unmatched convenience and lifestyle appeal. Twin Creeks is a golf-cart-friendly, amenity-rich

  Eberley Holloway Southern Middle Realty

  0 Dry Fork Unit 62, Winchester, TN 37398
• 

  

  /82

  $410,000

  Sold Jun 30, 2026

  963 Lynchburg Rd, Winchester, TN 37398

  • 4 Beds
  • 3 Baths
  • 2,038 Sq Ft
  • Built 1910

  Last Sold Summary

  • 12% Below List Price
  • $201/SF
  • 59 Days On Market

  Current Estimated Value $447,256

  Last Listing Agent Mimi Genet Parks Auction & Realty

  963 Lynchburg Rd, Winchester, TN 37398
• 

  

  /32

  Est $187,726

  Not Listed For Sale

  42 Kitchen Hollow Rd, Winchester, TN 37398

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1954

  42 Kitchen Hollow Rd, Winchester, TN 37398

  Last Sold Summary

  • 34 Days On Market

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

  /2

  Call for Price

  Pending

  • Land
  • 0 Sq Ft

  0 Gem SW Unit RTC3244799, Winchester, TN 37398

  Selling At Auction on July !8 @ 11am Subject to Chancery Court Approval

  John Smith, Jr. John Smith Jr Realty and Auction LLC

  0 Gem SW Unit RTC3244799, Winchester, TN 37398
• 

  

  /33

  $430,000

  Sold Jun 11, 2026

  211 Miller Farm Ln, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,564 Sq Ft
  • Built 2023

  Last Sold Summary

  • 7% Below List Price
  • $275/SF
  • 57 Days On Market

  Current Estimated Value $424,711

  Last Listing Agent Donald Barnes Coldwell Banker Southern Realty

  211 Miller Farm Ln, Winchester, TN 37398
• 

  

  /31

  Est $273,171

  Not Listed For Sale

  103 Allen Dr, Winchester, TN 37398

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • Built 1965

  103 Allen Dr, Winchester, TN 37398

  Last Sold Summary

  • 61 Days On Market

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

  

  /8

  $47,500

  • Land
  • 22,651 Sq Ft
  • $91,346 per Acre

  60 Lees Ford Ln, Winchester, TN 37398

  Opportunity awaits on this wooded corner lot close to Tims Ford Lake! Just a short drive to either Tullahoma or Winchester, or multiple Lakes within 30 mins. This lot was a previous home site and would be ideal for your new home or recreational use. This property is being sold strictly as-is. The buyer will be responsible for verifying all zoning, utility availability, lot dimensions, access, and

  Victoria Monilaw Better Homes & Gardens Real Estate Heritage Group

  60 Lees Ford Ln, Winchester, TN 37398
• 

  

  /82

  $1,188,412

  Sold Aug 13, 2025

  481 Winding Path, Winchester, TN 37398

  • 3 Beds
  • 4 Baths
  • 4,115 Sq Ft
  • Built 1978

  Last Sold Summary

  • $289/SF
  • 33 Days On Market

  Current Estimated Value $1,099,228

  Last Listing Agent Charlie Montgomery Comas Montgomery Realty & Auction

  481 Winding Path, Winchester, TN 37398
• 

  

  /23

  Est $270,179

  Not Listed For Sale

  109 Allen Dr, Winchester, TN 37398

  • 4 Beds
  • 2 Baths
  • 1,575 Sq Ft
  • Built 1967

  109 Allen Dr, Winchester, TN 37398

  Last Sold Summary

  • 102 Days On Market

  Last Listing Agent Melissa Stewart Swaffords Property Shop
• 

  

  /35

  $79,900

  • Land
  • 0 Sq Ft

  0 Campfire Ct Unit 394, Winchester, TN 37398

  Build your dream home in the exclusive, gated Twin Creeks Village on Tim’s Ford Lake—ideally located directly across from one of the community’s resort-style pools and pool house. This prime homesite places you in the heart of one of Winchester’s most sought-after lake communities, offering unmatched convenience and lifestyle appeal. Twin Creeks is a golf-cart-friendly, amenity-rich neighborhood

  Eberley Holloway Southern Middle Realty

  0 Campfire Ct Unit 394, Winchester, TN 37398
• 

  

  /15

  $279,000

  Sold Jul 02, 2026

  0 Crestfield Cir Unit 14, Winchester, TN 37398

  • Land
  • 34,848 Sq Ft
  • $348,750 per Acre

  Last Sold Summary

  • 3 Days On Market

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

  0 Crestfield Cir Unit 14, Winchester, TN 37398
• 

  

  /44

  Est $250,431

  Not Listed For Sale

  110 Kay St, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,514 Sq Ft
  • Built 1960

  110 Kay St, Winchester, TN 37398

  Last Sold Summary

  • 75 Days On Market

  Last Listing Agent Jeromey Cromwell RE/MAX 1st Realty
• 

  

  /27

  $369,999

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,548 Sq Ft

  131 Charlotte Dr, Winchester, TN 37398

  Bring Offers! Welcome Home!! Such a cute, well designed and spaciously laid out home that proudly boasts of 1,548 sq ft of comfortable living space!! The home welcomes you through the foyer into the roomy Living Room with a gas fireplace and custom tilework. The hardwood floors throughout this home are so beautiful and compliment every room only to add to the elegance of this beautifully designed

  Landon Keller Century 21 Volunteer Realty

  131 Charlotte Dr, Winchester, TN 37398

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