Winchester, TN Homes

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  /19

  $244,900

  • 3 Beds
  • 1.5 Baths
  • 1,333 Sq Ft

  205 8th Ave NW, Winchester, TN 37398

  Welcome to this delightful brick home nestled on a generous corner lot surrounded by mature shade trees. Full of character and timeless appeal, this home features gleaming original hardwood floors that add warmth and authenticity throughout. Perfectly situated close to town and just minutes from Tims Ford Lake. This combines peaceful living with everyday convenience. Replacement windows

  Angela Miller John Smith Jr Realty and Auction LLC

  205 8th Ave NW, Winchester, TN 37398
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  /27

  $520,000 Sold Apr 22, 2025

  185 Lookout Dr, Winchester, TN 37398

  • 3 Beds
  • 4 Baths
  • 2,556 Sq Ft
  • Built 2022

  Last Sold Summary

  • 5% Below List Price
  • $203/SF
  • 74 Days On Market

  Current Estimated Value $526,689

  Last Listing Agent Amanda Koziol eXp Realty

  185 Lookout Dr, Winchester, TN 37398
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  /14

  Est $194,250 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,110 Sq Ft

  307 N College St, Winchester, TN 37398

  307 N College St, Winchester, TN 37398
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  /32

  $215,000

  • Land
  • 0.91 Acre
  • $236,264 per Acre

  0 River Watch Way Unit RTC3032406, Winchester, TN 37398

  Lots 523 and 524 bundled together to offer you the best opportunity in the community to build two custom homes! Enjoy TWO incredible lots with lake views in a secluded and private section of the neighborhood that has an abundance of amenities. Ready to start living the lake life? This is the spot you have been looking for! Enjoy the clubhouse, pool, putting green, fire pit, pavilion, boat storage

  Jason Hilbelink Onward Real Estate

  0 River Watch Way Unit RTC3032406, Winchester, TN 37398
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  /87

  $1,300,000 Sold May 21, 2025

  2090 Little Hurricane Rd, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,454 Sq Ft
  • Built 1978

  Last Sold Summary

  • $530/SF
  • 39 Days On Market

  Current Estimated Value $1,210,051

  Last Listing Agent Lea Anne Bedsole Compass

  2090 Little Hurricane Rd, Winchester, TN 37398
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  /15

  Est $197,149 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,783 Sq Ft

  208 3rd Ave NW, Winchester, TN 37398

  208 3rd Ave NW, Winchester, TN 37398
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  /37

  $694,900 Pending

  • 4 Beds
  • 4.5 Baths
  • 3,017 Sq Ft

  255 Ridgecrest Dr, Winchester, TN 37398

  This customized Brick home has been expanded to Approx. 3017 SQ FT. Home is finished with Scratch proof and waterproof LVP and tile flooring( no carpet ) Kitchen is completed with Upgraded Kitchen Aid SS Appliance. Garage has been stretched to accommodate larger vehicles. Great room has12ft coffered ceiling. Laundry room has been expanded to allow for butlers pantry. Walk in pantry is adjacent to

  Angela Privett Benchmark Realty, LLC

  255 Ridgecrest Dr, Winchester, TN 37398
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  /8

  $224,990 Sold Sep 17, 2025

  0 Kayak Way Unit RTC2924412, Winchester, TN 37398

  • Land
  • 0 Acre

  Last Sold Summary

  • 6% Below List Price
  • 67 Days On Market

  Last Listing Agent Jon Sexton Benchmark Realty, LLC

  0 Kayak Way Unit RTC2924412, Winchester, TN 37398
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  /18

  Est $216,341 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,538 Sq Ft

  111 S Oak St, Winchester, TN 37398

  111 S Oak St, Winchester, TN 37398
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  /21

  $449,000

  • 4 Beds
  • 2.5 Baths
  • 2,305 Sq Ft

  58 Island Way, Winchester, TN 37398

  Spacious luxury townhome in gated community. Community has three swimming pools and a clubhouse and is adjacent to a full service marina on Tim's Ford lake. Grass and exterior maintenance is included in association fees. Back yard is fenced and ready for your furry friends. Gated community with golf cart access to marina. Community is near to golf courses, state parks and downtown Winchester.

  Daniel Demers Sell Your Home Services, LLC

  58 Island Way, Winchester, TN 37398
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  /41

  $285,000 Sold Aug 11, 2025

  419 Strawberry Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft
  • Built 2011

  Last Sold Summary

  • 5% Below List Price
  • $195/SF
  • 54 Days On Market

  Current Estimated Value $288,681

  Last Listing Agent Brandy Lee Gambill Georgia Evans Realty, LLC

  419 Strawberry Dr, Winchester, TN 37398
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  /69

  Est $518,244 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,380 Sq Ft

  227 Sells St, Winchester, TN 37398

  227 Sells St, Winchester, TN 37398
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  /40

  $344,900

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  605 Strawberry Dr, Winchester, TN 37398

  Charming, stylish, and move-in ready — this 3 bedroom, 2 bath home feels like new and offers the perfect mix of comfort and convenience! Step inside to an inviting open-concept layout with stainless steel appliances, plenty of natural light, and a smart split-bedroom design for added privacy.Love outdoor living? You’ll swoon over the large front porch for morning coffee and the expansive

  Kate Bryant RE/MAX 1st Realty

  605 Strawberry Dr, Winchester, TN 37398
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  /16

  $180,000 Sold Oct 01, 2025

  810 Lynwood St, Winchester, TN 37398

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1948

  Last Sold Summary

  • 3% Below List Price
  • $161/SF
  • 22 Days On Market

  Last Listing Agent Shawna Denby 1st Choice REALTOR

  810 Lynwood St, Winchester, TN 37398
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  /30

  Est $226,827 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,352 Sq Ft

  207 Hilldale Dr, Winchester, TN 37398

  207 Hilldale Dr, Winchester, TN 37398
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  /3

  $76,900

  • Land
  • 0.16 Acre
  • $480,625 per Acre

  0 Deer Valley Cir Unit RTC2980737, 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 RTC2980737, Winchester, TN 37398
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  /58

  $969,999 Sold Jul 15, 2025

  45 Hickory Point Dr, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,582 Sq Ft
  • Built 2022

  Last Sold Summary

  • 3% Below List Price
  • $376/SF
  • 49 Days On Market

  Current Estimated Value $940,761

  Last Listing Agent Derrick Foster Keller Williams Realty Nashville/Franklin

  45 Hickory Point Dr, Winchester, TN 37398
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  /3

  Est $171,619 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 928 Sq Ft

  807 Hunt St, Winchester, TN 37398

  807 Hunt St, Winchester, TN 37398
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  /28

  $140,000

  • Land
  • 0.66 Acre
  • $212,121 per Acre

  0 River Watch Way Unit RTC3032408, Winchester, TN 37398

  Fabulous opportunity to build your dream lake home on a large level lot in one of the most private and secluded areas of the community. It is hard to get any closer to Tims Ford Lake with the potential for lake views right from your home! Want a big yard? Build on this lot and purchase the one next door from us too. Enjoy the clubhouse, pool, putting green, fire pit, pavilion, boat storage lot,

  Jason Hilbelink Onward Real Estate

  0 River Watch Way Unit RTC3032408, Winchester, TN 37398
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  /59

  $1,600,000 Sold Aug 26, 2025

  • 4,352 Sq Ft
  • $368/SF

  • 6 Beds
  • 5 Baths
  • Built 2025

  947 Fanning Bend Dr, Winchester, TN 37398

  Experience lakeside luxury in this stunning 6-bedroom, 5-bath home on beautiful Tims Ford Lake. With 4,352 square feet of serene living space, this home is designed for comfort, style, and breathtaking views. Start your mornings with coffee in the charming breakfast nook and wind down your evenings on the screened porch—both overlooking the peaceful waters of the lake. The high-end kitchen

  947 Fanning Bend Dr, Winchester, TN 37398
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  /42

  Est $235,333 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,744 Sq Ft

  306 6th Ave NW Unit 304, Winchester, TN 37398

  306 6th Ave NW Unit 304, Winchester, TN 37398
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  /4

  $89,900

  • Land
  • 1.01 Acres
  • $89,010 per Acre

  0 Rowe Gap Rd, Winchester, TN 37398

  Beautiful 1-acre lot located in Winchester, TN. This property offers a peaceful country setting. Perfect for building your dream home or a weekend getaway. Enjoy the charm of small-town living while being just minutes from Tims Ford Lake, shopping, and schools. Don’t miss this opportunity to own your slice of Tennessee!

  LeighAnn Tillett Lamica Realty

  0 Rowe Gap Rd, Winchester, TN 37398
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  /46

  $590,000 Sold Mar 12, 2025

  181 Why Worry Ln, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,598 Sq Ft
  • Built 2021

  Last Sold Summary

  • 1% Below List Price
  • $227/SF
  • 3 Days On Market

  Current Estimated Value $591,328

  Last Listing Agent Lise Deschenes Fridrich & Clark Realty

  181 Why Worry Ln, Winchester, TN 37398
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  /33

  Est $379,749 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,772 Sq Ft

  513 N High St, Winchester, TN 37398

  513 N High St, Winchester, TN 37398
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  /2

  $165,000

  • Land
  • 0.7 Acre
  • $235,714 per Acre

  0 Cascade Dr Unit RTC2987667, Winchester, TN 37398

  Build your dream home on this beautiful lot in Stone Field Heights Ph I. Subdivision conveniently located to downtown Winchester, Tim's Food Lake, shopping and restaurants. Has city water, underground utilities, sewer available. Minium square footage requirements are 2300 ft and plans must be approved by developer.

  Renee Keene WEICHERT, REALTORS Joe Orr & Associates

  0 Cascade Dr Unit RTC2987667, Winchester, TN 37398
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  /35

  $408,000 Sold Apr 08, 2025

  8433 Lynchburg Rd, Winchester, TN 37398

  • 4 Beds
  • 2 Baths
  • 2,110 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $193/SF
  • 102 Days On Market

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

  8433 Lynchburg Rd, Winchester, TN 37398
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  /24

  Est $131,782 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 964 Sq Ft

  800 Lynwood St, Winchester, TN 37398

  800 Lynwood St, Winchester, TN 37398
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  /55

  $275,000 Under Contract

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

  201&203 3rd Ave NE, Winchester, TN 37398

  Incredible Dual-Home Investment Opportunity in the Heart of Winchester! Unlock immediate cash flow with TWO separate 2-bedroom, 1-bath homes situated on a single parcel in a sought-after Winchester location. Each home is currently leased at $340 per week—making this an ideal turnkey investment. Perfect for both seasoned investors and newcomers to the rental market, these low-maintenance

  Lindsey Bruce

  201&203 3rd Ave NE, Winchester, TN 37398
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  /3

  $40,000 Sold Jun 20, 2025

  0 Old Tullahoma Rd Unit RTC2775155, Winchester, TN 37398

  • Land
  • 3.19 Acres
  • $12,539 per Acre

  Last Sold Summary

  • 60% Below List Price
  • 142 Days On Market

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

  0 Old Tullahoma Rd Unit RTC2775155, Winchester, TN 37398
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  /28

  Est $161,173 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft

  724 N High St, Winchester, TN 37398

  724 N High St, Winchester, TN 37398
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  /41

  $374,900

  • 3 Beds
  • 2 Baths
  • 2,172 Sq Ft

  120 Dogwood Ln, Winchester, TN 37398

  Charming updated one-level home offering 3 bedrooms and 2 bathrooms, plus a possible 4th bedroom that could also serve as a bonus room, playroom, office, or separate living space. The spacious kitchen features granite countertops, ample cabinetry, and an eat-in area that opens to a formal dining space. Hardwood floors and stylish updates flow throughout, creating a warm and inviting atmosphere. A

  Sara Beth Bryant Tree City Realty

  120 Dogwood Ln, Winchester, TN 37398
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  /49

  $587,500 Sold Mar 26, 2025

  794 River Watch Way, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft
  • Built 2022

  Last Sold Summary

  • 1% Below List Price
  • $308/SF
  • 0 Days On Market

  Current Estimated Value $583,760

  Last Listing Agent Susan Baker BHGRE Baker & Cole

  794 River Watch Way, Winchester, TN 37398
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  /13

  Est $129,298 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  712 N Vine St, Winchester, TN 37398

  712 N Vine St, Winchester, TN 37398
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  /11

  $454,900

  • 4 Beds
  • 2 Baths
  • 1,890 Sq Ft

  0 Lookout Dr Unit RTC3015909, Winchester, TN 37398

  Welcome to the Winchester Plan—a beautifully designed 1-level, 4-bedroom home offering comfort, style, and functionality! The open living concept creates a warm and inviting atmosphere, perfect for family gatherings and entertaining guests. Enjoy relaxing evenings on the covered back porch, ideal for outdoor dining or simply taking in the peaceful surroundings. Located in a gated, family-friendly

  Mitchell Bowman simpliHOM - The Results Team

  0 Lookout Dr Unit RTC3015909, Winchester, TN 37398
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  /30

  $375,000 Sold Apr 11, 2025

  743 Hopkins Ln, Winchester, TN 37398

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

  Last Sold Summary

  • 15% Below List Price
  • $153/SF
  • 214 Days On Market

  Current Estimated Value $399,805

  Last Listing Agent Tyler Henley Franklin County Realty

  743 Hopkins Ln, Winchester, TN 37398
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  /16

  Est $151,127 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 683 Sq Ft

  721 N Vine St, Winchester, TN 37398

  721 N Vine St, Winchester, TN 37398
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  /17

  $245,000 Pending

  • Land
  • 0 Acre

  0 Kayak Way Unit RTC3018220, Winchester, TN 37398

  Welcome to this beautiful LAKEFRONT lot in the coveted Twin Creeks community! Nestled directly on the water, this lot is cleared and ready to build. Choose your own builder and design the home of your dreams in a community rich with amenities. Twin Creeks offers three inviting pools, a clubhouse for social gatherings, scenic walking trails, and a full-service marina with boat slips, rentals, and

  Heather Boldizsar Lake Homes Realty, LLC

  0 Kayak Way Unit RTC3018220, Winchester, TN 37398
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  /34

  $405,000 Sold Apr 16, 2025

  1487 S College St, Winchester, TN 37398

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

  Last Sold Summary

  • 13% Below List Price
  • $127/SF
  • 77 Days On Market

  Current Estimated Value $447,536

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

  1487 S College St, Winchester, TN 37398
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  /15

  Est $182,021 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 928 Sq Ft

  708 N Cedar St, Winchester, TN 37398

  708 N Cedar St, Winchester, TN 37398
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  /4

  $74,900

  • Land
  • 0.76 Acre
  • $98,553 per Acre

  0 Rocky Hollow Dr Unit RTC3066568, Winchester, TN 37398

  Excellent build lot available in the desirable Hopkins Point neighborhood. Private boat launch in neighborhood. House for sale next door at 21 Hilltop Dr. Buy one or buy both!

  Frederick Moore Compass

  0 Rocky Hollow Dr Unit RTC3066568, Winchester, TN 37398

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