Winchester, TN Homes

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  /36

  $299,900

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,999 Sq Ft

  206 Homeward Ave, Winchester, TN 37398

  Welcome home to this beautifully maintained 4-bedroom, 2-bath gem that checks every box — and then some. From the moment you step inside, rich hardwood flooring, fresh interior paint, recessed lighting, and stylish new light fixtures set the tone for a home that feels move-in ready and thoughtfully cared for. The spacious layout gives you room to truly live — multiple living areas mean everyone

  

  Tekesha Fuqua-Taylor

  Keller Williams Realty - Murfreesboro

  206 Homeward Ave, Winchester, TN 37398
• 

  

  

  /12

  $1,950 Per Month

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft
  • House for Rent

  389 Colonial Dr, Winchester, TN 37398

  This inviting home in beautiful Cherokee Estates offers the perfect blend of comfort and convenience. Featuring three spacious bedrooms and two well-appointed bathrooms, the property includes a large garage ideal for storage or hobbies, a cozy fireplace that anchors the living area, and a generous backyard perfect for outdoor enjoyment. With its warm character and desirable neighborhood setting,

  Angela Miller John Smith Jr Realty and Auction LLC

  389 Colonial Dr, Winchester, TN 37398
• 

  

  

  /33

  $344,000

  Sold Oct 30, 2025

  906 N High St, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,976 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Below List Price
  • $174/SF
  • 66 Days On Market

  Current Estimated Value $348,744

  Last Listing Agent Patsy Truslow Sewanee Realty

  906 N High St, Winchester, TN 37398
• 

  

  

  /34

  Est $279,612

  Not Listed For Sale

  174 Apple Dr, Winchester, TN 37398

  • 4 Beds
  • 2 Baths
  • 1,521 Sq Ft
  • Built 2009

  174 Apple Dr, Winchester, TN 37398

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Houston Poston BHHS Southern Routes Realty
• 

  

  

  /5

  $459,999

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 2,355 Sq Ft

  262 Crimson Dr, Winchester, TN 37398

  Coming Soon along with professional pictures! Brick Ranch in Prime Winchester Location! Welcome home to this 3-bedroom, 2-full-bath brick home situated on a spacious 0.7-acre lot in a quiet, established subdivision. Featuring a desirable split-bedroom floor plan, this property offers the perfect blend of privacy, comfort, and convenience. The primary bedroom is a true sanctuary, featuring 252' sq

  

  Melissa Stewart

  Swaffords Property Shop

  262 Crimson Dr, Winchester, TN 37398
• 

  

  /21

  $1,250 Per Month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Recently Remodeled Duplex

  201 9th Ave NW Unit 1, Winchester, TN 37398

  Located within walking distance of the beautiful Downtown Winchester Square, with lots of shopping and fine dining. As well as the Famous Oldham Theater.Also located walking distance from Tims Ford Lake, where there is always something to do, with tennis courts, blueway, ball fields, dog park, tennis, basketball and pickle ball, fishing, disc golf, playground, boat launch, or just sitting on

  201 9th Ave NW Unit 1, Winchester, TN 37398
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  /72

  $419,000

  Sold Apr 02, 2026

  225 Crimson Dr, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 2,485 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $169/SF
  • 21 Days On Market

  Current Estimated Value $429,484

  Last Listing Agent Charlie Gonzales Southern Middle Realty

  225 Crimson Dr, Winchester, TN 37398
• 

  

  /64

  Est $478,681

  Not Listed For Sale

  146 Brandi Way, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • Built 2009

  146 Brandi Way, Winchester, TN 37398

  Last Sold Summary

  • 102 Days On Market

  Last Listing Agent Melissa Wilson Southern Middle Realty
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  /85

  $1,445,000

  $80K PRICE DROP

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

  71 Slalom Cir, Winchester, TN 37398

  Luxury Lakefront Home in Gated Community – Over 4,500 Sq Ft of Elegant Living. Discover the epitome of upscale living in this stunning lakefront estate, nestled within a secure gated community. Meticulously designed space, this residence offers sweeping views of TVA grounds and the tranquil lake from Primary Bedroom and Office. **Key Features Include:** - **Spacious & Elegant Interiors:** 10 and

  

  Billie Kay Caldwell

  Swaffords Property Shop

  71 Slalom Cir, Winchester, TN 37398
• 

  

  /49

  $478,000

  Sold Jun 01, 2026

  146 Island Way, Winchester, TN 37398

  • 4 Beds
  • 3 Baths
  • 2,578 Sq Ft
  • Built 2019

  Last Sold Summary

  • 4% Below List Price
  • $185/SF
  • 235 Days On Market

  Current Estimated Value $490,885

  Last Listing Agent Alley Christenson Synergy Realty Network, LLC

  146 Island Way, Winchester, TN 37398
• 

  

  /15

  Est $147,051

  Not Listed For Sale

  816 Mason Ave, Winchester, TN 37398

  • 3 Beds
  • 1 Bath
  • 808 Sq Ft
  • Built 1950

  816 Mason Ave, Winchester, TN 37398

  Last Sold Summary

  • 50 Days On Market

  Last Listing Agent Sean Crabtree Blue Door Realty Group
• 

  

  /14

  $199,000

  • Land
  • 0 Sq Ft

  0 Slalom Cir Unit 119, Winchester, TN 37398

  Large corner lot located directly next to the golf cart path to take you straight to Tim's Ford Lake, the Marina and Drafts and Watercrafts (the floating restaurant and bar!) This lot is perfect for a multi level home to take in lake views from the 2nd story! Enjoy all the amenities that Twin Creeks Village has to offer: Clubhouse on site, 3 swimming pools, sandy beach, walking trails, campground

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  0 Slalom Cir Unit 119, Winchester, TN 37398
• 

  

  /3

  $79,900

  Sold Sep 16, 2025

  0 Deer Valley Cir Unit RTC2980795, Winchester, TN 37398

  • Land
  • 16,988 Sq Ft
  • $204,872 per Acre

  Last Sold Summary

  • 0 Days On Market

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

  0 Deer Valley Cir Unit RTC2980795, Winchester, TN 37398
• 

  

  /86

  Est $851,892

  Not Listed For Sale

  264 Cascade Dr, Winchester, TN 37398

  • 5 Beds
  • 3.5 Baths
  • 3,729 Sq Ft
  • Built 2008

  264 Cascade Dr, Winchester, TN 37398

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Jessica London Southern Middle Realty
• 

  

  /13

  $159,000

  • Land
  • 2.19 Acres
  • $72,603 per Acre

  0 Metcalf Rd Unit RTC3243837, Winchester, TN 37398

  Discover the possibilities on this beautiful 2.19-acre property, ready for your next project. Whether you're envisioning a mini farm, a custom dream home, or an investment opportunity, this versatile tract offers exceptional potential. A preliminary soil test supports a 4-bedroom home site, making it easier to start planning your build. Zoned R-2, the property may also accommodate duplex

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  0 Metcalf Rd Unit RTC3243837, Winchester, TN 37398
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  /36

  $325,000

  Sold Jun 23, 2026

  1517 Paynes Church Rd, Winchester, TN 37398

  • 3 Beds
  • 2.5 Baths
  • 1,508 Sq Ft
  • Built 2025

  Last Sold Summary

  • 7% Below List Price
  • $216/SF
  • 229 Days On Market

  Last Listing Agent Kasidy Lowe Compass Tennessee, LLC

  1517 Paynes Church Rd, Winchester, TN 37398
• 

  

  /32

  Est $261,370

  Not Listed For Sale

  1322 Marble Hill Rd, Winchester, TN 37398

  • 4 Beds
  • 1 Bath
  • 2,138 Sq Ft
  • Built 1930

  1322 Marble Hill Rd, Winchester, TN 37398

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Joe Orr WEICHERT, REALTORS Joe Orr & Associates
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  /51

  $279,900

  • 3 Beds
  • 1.5 Baths
  • 1,697 Sq Ft

  801 S High St, Winchester, TN 37398

  Move-in ready with charm, space, and versatility. This beautifully refreshed home has been updated with fresh paint throughout, new light fixtures, and fresh landscaping. The spacious primary bedroom features vaulted ceilings and natural lighting. A brand new water heater and included washer and dryer add convenience for the new owner. Step outside to enjoy the large, beautiful backyard, perfect

  

  Chelsea Greenway

  Southern Middle Realty

  801 S High St, Winchester, TN 37398
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  /26

  $175,000

  Sold Jul 24, 2026

  714 N Cedar St, Winchester, TN 37398

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Below List Price
  • $152/SF
  • 157 Days On Market

  Current Estimated Value $174,060

  Last Listing Agent Eberley Holloway Southern Middle Realty

  714 N Cedar St, Winchester, TN 37398
• 

  

  /4

  Est $176,141

  Not Listed For Sale

  1770 Short Creek Rd, Winchester, TN 37398

  • Built 1900

  1770 Short Creek Rd, Winchester, TN 37398

  Last Sold Summary

  • 364 Days On Market

  Last Listing Agent James Sutton SUTTON REALTY CO.
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  /38

  $875,500

  $325K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,640 Sq Ft

  182 Loop Dr, Winchester, TN 37398

  Property has added a floating dock - Welcome to 182 Loop Drive, where lake living meets comfort, flexibility, & endless opportunities for entertaining, relaxing, or generating income. Perfectly positioned on a scenic hillside lot, beautiful lake views, spacious 5 bedroom, 3 Bath home has been thoughtfully designed to accommodate everything from large family gatherings to weekend getaways &

  

  Billie Kay Caldwell

  Swaffords Property Shop

  182 Loop Dr, Winchester, TN 37398
• 

  

  /17

  $189,471

  Sold Nov 05, 2025

  0 Aedc Rd Unit RTC3007773, Winchester, TN 37398

  • Land
  • 3.38 Acres
  • $56,057 per Acre

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Vandy VanMeter Parks Auction & Realty

  0 Aedc Rd Unit RTC3007773, Winchester, TN 37398
• 

  

  /69

  Est $723,190

  Not Listed For Sale

  200 Greenleaf Ln, Winchester, TN 37398

  • 5 Beds
  • 3 Baths
  • 2,957 Sq Ft
  • Built 1987

  200 Greenleaf Ln, Winchester, TN 37398

  Last Sold Summary

  • 111 Days On Market

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

  

  /40

  $695,900

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

  59 Turtle Ct, Winchester, TN 37398

  Lake Life at its FINEST- this remarkable home in Twin Creeks Subdivision has everything you need! Open Living concept for easy entertaining featuring vaulted ceilings, 5 burner Gas cooktop, double ovens, Quartz countertops and designer lighting. Primary suite is on the main level. Upstairs features 3 large bedrooms all with walk in closets as well as built in bunks perfect for sleepovers! Large

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  59 Turtle Ct, Winchester, TN 37398
• 

  

  /3

  $73,750

  Sold Feb 18, 2026

  0 Deer Valley Cir Unit RTC2980801, Winchester, TN 37398

  • Land
  • 16,988 Sq Ft
  • $189,103 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 169 Days On Market

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

  0 Deer Valley Cir Unit RTC2980801, Winchester, TN 37398
• 

  

  /48

  Est $568,065

  Not Listed For Sale

  124 Sugar Leaf Cir, Winchester, TN 37398

  • 5 Beds
  • 3.5 Baths
  • 3,776 Sq Ft
  • Built 1993

  124 Sugar Leaf Cir, Winchester, TN 37398

  Last Sold Summary

  • 234 Days On Market

  Last Listing Agent Mike Stubblefield Franklin County Realty
• 

  

  /75

  $879,900

  • 5 Beds
  • 4.5 Baths
  • 3,095 Sq Ft

  53 River Watch Way, Winchester, TN 37398

  Experience elevated lake living in the highly sought-after Twin Creeks Village on beautiful Tims Ford Lake. This stunning 2-story brick home offers 5 bedrooms, 4.5 baths, and 3,095 sq ft of thoughtfully designed living space within a gated, resort-style waterfront community. The open-concept living area with fireplace flows seamlessly into the kitchen, creating a warm yet sophisticated setting

  

  John Peck

  Century 21 Volunteer Realty

  53 River Watch Way, Winchester, TN 37398
• 

  

  /3

  $112,500

  Sold May 08, 2026

  0 Pickney Rd, Winchester, TN 37398

  • Land
  • 40,075 Sq Ft
  • $122,283 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 6 Days On Market

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

  0 Pickney Rd, Winchester, TN 37398
• 

  

  /22

  Est $244,963

  Not Listed For Sale

  211 N Jefferson St, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,956 Sq Ft
  • Built 1920

  211 N Jefferson St, Winchester, TN 37398

  Last Sold Summary

  • 81 Days On Market

  Last Listing Agent Penny Patterson Swaffords Property Shop
• 

  

  /17

  $99,999

  • Land
  • 0 Sq Ft

  0 Campfire Ct Unit 463, Winchester, TN 37398

  

  Billie Kay Caldwell

  Swaffords Property Shop

  0 Campfire Ct Unit 463, Winchester, TN 37398
• 

  

  /70

  $1,615,000

  Sold Jul 15, 2026

  959 Fanning Bend Dr, Winchester, TN 37398

  • 6 Beds
  • 8 Baths
  • 4,678 Sq Ft
  • Built 2026

  Last Sold Summary

  • 5% Below List Price
  • $345/SF
  • 58 Days On Market

  Last Listing Agent Brandon Bubis Legacy South Brokerage

  959 Fanning Bend Dr, Winchester, TN 37398
• 

  

  /13

  Est $181,761

  Not Listed For Sale

  808 N High St, Winchester, TN 37398

  • 2 Beds
  • 1.5 Baths
  • 971 Sq Ft
  • Built 1941

  808 N High St, Winchester, TN 37398

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Timothy Anderson Anderson Realty Services
• 

  

  /39

  $544,900

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,327 Sq Ft

  215 Franklin Heights Dr, Winchester, TN 37398

  This beautiful all-brick, single-level home offers the perfect blend of comfort, style, and convenience. Featuring 3 spacious bedrooms and 2.5 bathrooms, this move-in-ready property sits on a large corner lot, providing both space and privacy. Recent upgrades include a brand-new roof, energy-efficient windows, and a new HVAC system for peace of mind. Inside, you’ll find fresh paint throughout,

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  215 Franklin Heights Dr, Winchester, TN 37398
• 

  

  /8

  $199,900

  Sold Mar 24, 2026

  141 Modena Cir, Decherd, TN 37324

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 2003

  Last Sold Summary

  • $161/SF
  • 31 Days On Market

  Current Estimated Value $206,395

  Last Listing Agent Benjamin Merrill Lynch Rigsby Realty & Auction, LLC

  141 Modena Cir, Decherd, TN 37324
• 

  

  /30

  Est $275,508

  Not Listed For Sale

  759 Little Hurricane Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1979

  759 Little Hurricane Rd, Winchester, TN 37398

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Melissa Stewart Swaffords Property Shop
• 

  

  /24

  $319,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft

  1687 Georgia Crossing Rd, Winchester, TN 37398

  Charming 2 bed, 2 bath home situated on 2.4 acres, offering the perfect blend of modern comfort and peaceful country living. This 1,080 sqft home features high ceilings, updated finishes, and a beautifully renovated primary bathroom. Enjoy year-round relaxation in the Florida room, or step outside to take in the scenic surroundings. The newly built shop provides excellent space for storage,

  

  John Peck

  Century 21 Volunteer Realty

  1687 Georgia Crossing Rd, Winchester, TN 37398
• 

  

  /32

  $309,000

  Sold Mar 06, 2026

  25 Glasner Ln, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 2025

  Last Sold Summary

  • 8% Below List Price
  • $206/SF
  • 102 Days On Market

  Current Estimated Value $305,159

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  25 Glasner Ln, Winchester, TN 37398
• 

  

  /49

  Est $600,769

  Not Listed For Sale

  1026 Franklin Heights Dr, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 2,972 Sq Ft
  • Built 1996

  1026 Franklin Heights Dr, Winchester, TN 37398

  Last Sold Summary

  • 71 Days On Market

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

  

  /71

  $451,500

  $38K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,228 Sq Ft

  270 Wood Bluff Rd, Winchester, TN 37398

  Bring your fishing pole or Kayak! This charming 4-bedroom, 2.5-bathroom home is all about easy living and great views, especially with its direct access to the peaceful Boiling Fork Creek and Tim's Ford Lake. Tucked away in a lovely neighborhood full of mature trees and super close to everything you need, it features a fully fenced-in backyard that’s perfect for pets or just hanging out. Inside,

  

  Ashley Lynch

  Lynch Rigsby Realty & Auction, LLC

  270 Wood Bluff Rd, Winchester, TN 37398
• 

  

  /26

  $210,000

  Sold Jun 05, 2026

  3926 Old Tullahoma Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1969

  Last Sold Summary

  • 813% Above List Price
  • $162/SF
  • 36 Days On Market

  Current Estimated Value $219,292

  Last Listing Agent Linda McCall Coldwell Banker Southern Realty

  3926 Old Tullahoma Rd, Winchester, TN 37398

Showing Results 41 - 80, Page 2 of 18