Winchester, TN Homes

• 

  

  

  /29

  $357,000

  Sold May 23, 2025

  290 Colonial Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,644 Sq Ft
  • Built 2018

  Last Sold Summary

  • 1% Below List Price
  • $217/SF
  • 33 Days On Market

  Current Estimated Value $480,108

  Last Listing Agent Susan Baker BHGRE Baker & Cole

  290 Colonial Dr, Winchester, TN 37398
• 

  

  

  /35

  Est $263,416

  Not Listed For Sale

  259 Strawberry Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2005

  259 Strawberry Dr, Winchester, TN 37398

  Last Sold Summary

  • 3% Above List Price
  • $212/SF
  • 28 Days On Market

  • Last Sold Price $255,000
  • May 28, 2024

  Last Listing Agent Heather Burke Lynch Rigsby Realty & Auction, LLC
• 

  

  

  /15

  $140,000

  $60K PRICE DROP

  • Land
  • 0 Sq Ft

  0 Slalom Cir Unit 104, Winchester, TN 37398

  RECENTLY REDUCED! Don’t miss this opportunity to own one of the few remaining water-view building lots in the highly sought-after Twin Creeks Village community. Located on prestigious Lot #104 Slalom Circle, this prime homesite sits on one of the most desirable streets in the development—an ideal setting to build your custom water-view dream home in a peaceful, upscale lakeside

  Felicia Wright Leading Edge Real Estate Group

  0 Slalom Cir Unit 104, 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 $1,081,266

  Last Listing Agent Charlie Montgomery Comas Montgomery Realty & Auction

  481 Winding Path, Winchester, TN 37398
• 

  

  

  /35

  Est $406,521

  Not Listed For Sale

  1009 Holders Cove Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 2,148 Sq Ft
  • Built 1973

  1009 Holders Cove Rd, Winchester, TN 37398

  Last Sold Summary

  • 3% Above List Price
  • $184/SF
  • 170 Days On Market

  • Last Sold Price $395,000
  • Mar 08, 2024

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

  

  /18

  $239,900

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft

  286 Strawberry Dr, Winchester, TN 37398

  This all-brick, one-level home in Magnolia Estates offers a clean, move-in ready option just minutes from downtown Winchester and Tims Ford Lake. Inside, the layout is simple and easy to live in, with 3 bedrooms and 2 full bathrooms all on the main floor. The primary suite includes a separate tub and shower, while the secondary bedrooms offer larger closet space than you’d expect in this price

  Rachel Ferrell Southern Middle Realty

  286 Strawberry Dr, Winchester, TN 37398
• 

  

  /14

  $173,500

  Sold Jul 02, 2025

  100 Mountain View Dr, Winchester, TN 37398

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1963

  Last Sold Summary

  • 17% Below List Price
  • $181/SF
  • 92 Days On Market

  Current Estimated Value $169,830

  Last Listing Agent Mike Stubblefield Franklin County Realty

  100 Mountain View Dr, Winchester, TN 37398
• 

  

  /21

  Est $266,067

  Not Listed For Sale

  238 Crestview Dr, Winchester, TN 37398

  • 3 Beds
  • 1 Bath
  • 1,620 Sq Ft
  • Built 1967

  238 Crestview Dr, Winchester, TN 37398

  Last Sold Summary

  • 4% Above List Price
  • $157/SF
  • 8 Days On Market

  • Last Sold Price $255,000
  • Dec 06, 2024

  Last Listing Agent Chris Hawkersmith Lynch Rigsby Realty & Auction, LLC
• 

  

  /36

  $639,000

  $36K PRICE DROP

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

  124 Barefoot Way, Winchester, TN 37398

  Rare lakeview opportunity in sought-after Barefoot Bay, a gated community on Tim’s Ford Lake. Currently operating as a successful short-term rental with strong financial performance, this beautifully designed home is being offered fully turn-key with furnishings and contents remaining. Priced accordingly, with the option to purchase without select furnishings/items if preferred. Custom built by

  Marla Richardson Parks Compass

  124 Barefoot Way, Winchester, TN 37398
• 

  

  /56

  $1,400,000

  Sold Jul 24, 2025

  408 Wildwood Cir, Winchester, TN 37398

  • 4 Beds
  • 3 Baths
  • 2,080 Sq Ft
  • Built 1995

  Last Sold Summary

  • $673/SF
  • 4 Days On Market

  Current Estimated Value $1,347,265

  Last Listing Agent Marla Richardson Parks Compass

  408 Wildwood Cir, Winchester, TN 37398
• 

  

  /41

  Est $326,716

  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

  • 1% Below List Price
  • $200/SF
  • 35 Days On Market

  • Last Sold Price $329,000
  • Oct 31, 2024

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

  

  /53

  $319,900

  • 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
• 

  

  /3

  $40,000

  Sold Jun 20, 2025

  0 Old Tullahoma Rd Unit RTC2775160, Winchester, TN 37398

  • Land
  • 1.15 Acres
  • $34,783 per Acre

  Last Sold Summary

  • 50% Below List Price
  • 142 Days On Market

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

  0 Old Tullahoma Rd Unit RTC2775160, Winchester, TN 37398
• 

  

  /42

  Est $549,100

  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

  • 1% Above List Price
  • $163/SF
  • 65 Days On Market

  • Last Sold Price $544,000
  • Dec 12, 2024

  Last Listing Agent Melissa Stewart Swaffords Property Shop
• 

  

  /7

  $99,000

  Under Contract

  • Land
  • 0 Sq Ft

  0 Golf Shores Dr Unit RTC3208495, Winchester, TN 37398

  Nestled in a beautiful setting and amazing neighborhood, the gorgeous flat lot spanning over half an acre offers the perfect opportunity to build your dream home or getaway retreat. Enjoy direct access to Tim's Ford Lake making it easy to fish or simply soak in your surroundings. Bordering Tim's Ford State Park this unique property provides immediate access to miles of hiking and nature trails.

  Chris Hawkersmith Lynch Rigsby Realty & Auction, LLC

  0 Golf Shores Dr Unit RTC3208495, Winchester, TN 37398
• 

  

  /14

  $70,000

  Sold Jun 20, 2025

  0 Grammer Hill Rd, Winchester, TN 37398

  • Land
  • 5.15 Acres
  • $13,592 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 7 Days On Market

  Last Listing Agent Charlie Gonzales Southern Middle Realty

  0 Grammer Hill Rd, Winchester, TN 37398
• 

  

  /29

  Est $262,173

  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

  • 1% Above List Price
  • $150/SF
  • 3 Days On Market

  • Last Sold Price $259,900
  • Nov 15, 2024

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

  

  /8

  $169,000

  • 2 Beds
  • 1 Bath
  • 885 Sq Ft

  101 Highland St, Winchester, TN 37398

  Charming cottage in the heart of Winchester offering incredible potential and a hard-to-find, large privacy-fenced backyard. This 2-bedroom, 1-bath home features a durable metal roof, newer replacement windows, a new shed, and a recently added driveway. The attic provides impressive space with exciting possibilities for future expansion or storage. While the home needs a little TLC, it’s a

  Fhonda Hatmaker eXp Realty

  101 Highland St, Winchester, TN 37398
• 

  

  /66

  $865,000

  Sold Jan 28, 2026

  138 Kayak Way, Winchester, TN 37398

  • 4 Beds
  • 4.5 Baths
  • 3,040 Sq Ft
  • Built 2025

  Last Sold Summary

  • 9% Below List Price
  • $285/SF
  • 0 Days On Market

  Last Listing Agent Christy Bashlor Onward Real Estate

  138 Kayak Way, Winchester, TN 37398
• 

  

  /43

  Est $373,978

  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

  • 12% Above List Price
  • $118/SF
  • 153 Days On Market

  • Last Sold Price $334,000
  • Feb 04, 2025

  Last Listing Agent Melissa Stewart Swaffords Property Shop
• 

  

  /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
• 

  

  /25

  $800,000

  Sold Aug 20, 2025

  1419 Dripping Springs Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 2,411 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $332/SF
  • 67 Days On Market

  Current Estimated Value $821,308

  Last Listing Agent Chris Hawkersmith Lynch Rigsby Realty & Auction, LLC

  1419 Dripping Springs Rd, Winchester, TN 37398
• 

  

  /14

  Est $367,655

  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

  • 47% Above List Price
  • $75/SF
  • 43 Days On Market

  • Last Sold Price $249,900
  • Jan 31, 2024

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

  

  /50

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,476 Sq Ft

  118 Bel Aire Dr, Winchester, TN 37398

  Welcome to 118 Bel Aire Dr— a charming solid brick home nestled on .34 acres in an established neighborhood. This 3 bedroom, 2 bathroom home offers a spacious kitchen and living room layout, perfect for everyday living and entertaining. The thoughtful floor plan provides comfortable living spaces while the large yard offers plenty of room to enjoy the outdoors. With timeless brick construction

  Jessica London Southern Middle Realty

  118 Bel Aire Dr, Winchester, TN 37398
• 

  

  /5

  $55,000

  Sold Jul 10, 2025

  0 Lynchburg Rd Unit RTC2899279, Winchester, TN 37398

  • Land
  • 41,817 Sq Ft
  • $57,292 per Acre

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  0 Lynchburg Rd Unit RTC2899279, Winchester, TN 37398
• 

  

  /10

  Est $209,148

  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

  • 5% Below List Price
  • $182/SF
  • 47 Days On Market

  • Last Sold Price $221,000
  • Sep 10, 2024

  Last Listing Agent Aleisha Putman Synergy Realty Network, LLC
• 

  

  /39

  $1,275,000

  • 3 Beds
  • 2 Baths
  • 2,184 Sq Ft

  90 Wildwood Ct, Winchester, TN 37398

  First-time offering of this incredible lakefront property, perfectly positioned at the end of a peninsula with open, year-round water views overlooking Tim’s Ford State Park. Truly one of a kind, this home features a boat dock, an open one-level floor plan, a spacious kitchen with a large island and abundant seating, plus a beautiful stone fireplace anchoring the main living area and large dining

  Marla Richardson Parks Compass

  90 Wildwood Ct, Winchester, TN 37398
• 

  /2

  $55,000

  Sold Mar 27, 2026

  1533 Rowe Gap Rd Unit 1 (3), Winchester, TN 37398

  • Land
  • 21,780 Sq Ft
  • $110,000 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 260 Days On Market

  Last Listing Agent Thomas Ore Winton Auction & Realty Co.

  1533 Rowe Gap Rd Unit 1 (3), Winchester, TN 37398
• 

  

  /40

  Est $416,271

  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

  • 14% Above List Price
  • $132/SF
  • 50 Days On Market

  • Last Sold Price $365,000
  • Sep 29, 2023

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

  

  /15

  $230,000

  • Land
  • 10,890 Sq Ft
  • $920,000 per Acre

  0 Kayak Way Unit 489, Winchester, TN 37398

  JUST LISTED!!! 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 use

  Felicia Wright Leading Edge Real Estate Group

  0 Kayak Way Unit 489, Winchester, TN 37398
• 

  

  /56

  $590,000

  Sold Feb 27, 2026

  110 Cascade Dr, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 2,464 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Below List Price
  • $239/SF
  • 14 Days On Market

  Current Estimated Value $161,333

  Last Listing Agent Jaclyn Harney-Williams Onward Real Estate

  110 Cascade Dr, Winchester, TN 37398
• 

  

  /24

  Est $306,066

  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

  • $130/SF
  • 43 Days On Market

  • Last Sold Price $305,000
  • Jan 31, 2025

  Last Listing Agent Christopher Smith Synergy Realty Network, LLC
• 

  

  /60

  $486,800

  $10K 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
• 

  

  /41

  $970,000

  Sold Nov 07, 2025

  1108 N Jefferson St, Winchester, TN 37398

  • 4 Beds
  • 7 Baths
  • 3,157 Sq Ft
  • Built 2025

  Last Sold Summary

  • 13% Below List Price
  • $307/SF
  • 78 Days On Market

  Last Listing Agent Tara Hays Benchmark Realty, LLC

  1108 N Jefferson St, Winchester, TN 37398
• 

  

  /26

  Est $240,452

  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

  • 12% Above List Price
  • $196/SF
  • 1 Day On Market

  • Last Sold Price $215,000
  • Sep 13, 2023

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

  

  /80

  $1,479,000

  Under Contract

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

  1305 Dripping Springs Rd, Winchester, TN 37398

  Experience lakefront living at its finest at 1305 Dripping Springs Rd on beautiful Tims Ford Reservoir! This spacious all-brick split-level home offers approximately 4,500 sq. ft. with 5 bedrooms and 4.5 baths, perfectly situated on a prime waterfront lot with very level and easy access to a private 2-slip covered floating boat dock. Mature shade trees and breathtaking water views create a

  Thomas Ore Winton Auction & Realty Co.

  1305 Dripping Springs Rd, Winchester, TN 37398
• 

  

  /27

  $340,000

  Sold Sep 25, 2025

  341 Carol Cir, Winchester, TN 37398

  • 4 Beds
  • 2.5 Baths
  • 1,788 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $190/SF
  • 89 Days On Market

  Current Estimated Value $337,011

  Last Listing Agent Chris Hawkersmith Lynch Rigsby Realty & Auction, LLC

  341 Carol Cir, Winchester, TN 37398
• 

  

  /27

  Est $441,673

  Not Listed For Sale

  7115 Lynchburg Rd, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 1974

  7115 Lynchburg Rd, Winchester, TN 37398

  Last Sold Summary

  • 12% Above List Price
  • $202/SF
  • 25 Days On Market

  • Last Sold Price $395,000
  • Jul 07, 2023

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

  

  /23

  Call for Price

  • 3 Beds
  • 2 Baths
  • 3,050 Sq Ft

  219 Old Mill Rd, Winchester, TN 37398

  Visit us on Saturday May 30th at NOON as we auction one of the most beautiful houses in Winchester to the public. Built in 1860 and classically remodeled with all the modern amenities you could want. Complete with claw foot tubs and a commercial kitchen. Step back in time as you admire the tall ceilings and the amazing chandeliers and the beautiful hardwood floors. Admire the old Magnolia trees

  Johnny Messick Exit Realty Bob Lamb & Associates

  219 Old Mill Rd, Winchester, TN 37398
• 

  

  /58

  $745,000

  Sold May 05, 2026

  47 Long View Dr, Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1983

  Last Sold Summary

  • 1% Below List Price
  • $310/SF
  • 16 Days On Market

  Current Estimated Value $728,874

  Last Listing Agent Justin Briggs Keller Williams Realty Nashville/Franklin

  47 Long View Dr, Winchester, TN 37398

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