Winchester, TN Homes for Sale

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  /63

  $307,900

  $2K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,213 Sq Ft

  103 N Shephard St, Winchester, TN 37398

  Welcome home to “A Whiter Shade of Pale,” a home that beautifully blends classic character with modern comfort. Perfectly situated within walking distance of downtown Winchester and just 1.5 miles from stunning Tims Ford Lake, this home offers the best of small-town living and outdoor adventure. Step inside to discover an inviting open-concept main level designed for both everyday living and

  Eberley Holloway Southern Middle Realty

  103 N Shephard St, Winchester, TN 37398
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  /47

  $650,000

  Open House 6/20 $49K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,952 Sq Ft

  16 Bingham Ct, Winchester, TN 37398

  Tucked inside the highly sought-after lake community of Dripping Springs, this beautifully fully updated home offers the kind of lifestyle people dream about. With year-round lake views and your very own private pier dock, every day feels like a getaway. Inside has been completely updated. The show-stopping floor-to-ceiling fireplace anchors the main living space creating a warm atmosphere.

  Thomas Ore Winton Auction & Realty Co.

  16 Bingham Ct, Winchester, TN 37398
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  /34

  $225,000

  • Land
  • 3 Acres
  • $75,000 per Acre

  0 Spring Hill Dr, Winchester, TN 37398

  Discover the perfect blend of convenience and freedom with this rare 3-acre parcel inside Winchester city limits. If you’ve been searching for a few acres to build your dream home—just minutes from downtown—this one checks every box. Located just beyond a neatly maintained grass-lined fence row at the edge of Winchester Village Phase II, the property offers the benefits of subdivision proximity

  Leah Dickert Noble Real Estate

  0 Spring Hill Dr, Winchester, TN 37398
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  /44

  $419,900

  $10K PRICE DROP

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

  802 Evans Rd, Winchester, TN 37398

  Escape to this peaceful, fully furnished home nestled on a 2.5 acre wooded lot just minutes from Tim's Ford Lake, a public boat ramp, and the world-famous Jack Daniel’s Distillery. This charming and successful Airbnb offers the perfect mix of charm and modern comfort. Inside, you'll find an updated kitchen with modern appliances, perfect for home-cooked meals, and cozy fireplaces to warm up after

  Hannah Monilaw Better Homes & Gardens Real Estate Heritage Group

  802 Evans Rd, Winchester, TN 37398
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  /30

  $325,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft

  101 Royal Oak Dr, Winchester, TN 37398

  Welcome to this well-maintained 3 bedroom, 2 bath brick home situated on 1.3 acre lot in a quiet well-established neighborhood just minutes from the lake. This charming property offers the perfect balance of privacy space and convenience, making it ideal for families, downsizing, or anyone looking to enjoy peaceful living close to outdoor recreation. The home features a bright and inviting living

  Chesney Luttrell John Smith Jr Realty and Auction LLC

  101 Royal Oak Dr, Winchester, TN 37398
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  /3

  $84,900

  $5K PRICE INCREASE

  • Land
  • 7,840 Sq Ft
  • $471,667 per Acre

  0 Kayak Way Unit 413, Winchester, TN 37398

  One of the prettiest gated lake communities in Tennessee. Come stay and play in this beautiful, gated community on Tims Ford Lake. Always something to do with walking trails, event center, waterfront dinning at Drafts & Watercrafts, clubhouse, heated pools, full-service marina w/dock, boat slip rental, underground utilities, High speed fiber internet, boat club, boat rentals and more. Only thing

  Sam Hatfield Sam Hatfield Realty, Inc.

  0 Kayak Way Unit 413, Winchester, TN 37398
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  /13

  $149,900

  $5K PRICE DROP

  • Land
  • 15,681 Sq Ft
  • $416,389 per Acre

  0 Paddleboard Ct Unit 229, Winchester, TN 37398

  Large cul-de-sac lot in Twin Creeks Village! This beautiful lot sits on the marina side of the neighborhood, placing you within easy walking or golf cart ride to the full-service marina, boat slips, a lakefront restaurant/bar, three resort-style pools, clubhouse, scenic walking trails, and a sandy beach area. Come design your multi-level dream home and take in the serene views and peaceful

  Andrew (Andy) McInturff Zach Taylor Real Estate

  0 Paddleboard Ct Unit 229, Winchester, TN 37398
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  /2

  $90,000

  • Land
  • 0 Sq Ft

  0 Turtle Ct Unit 375, Winchester, TN 37398

  Outstanding opportunity on a prime homesite in Twin Creeks Village, offering an attractive price point for a resort-style lake community. This level lot sets up beautifully for your future custom lake home and sits just inside the gated entrance, only a short walk or quick golf cart ride from the newly added third community pool. Whether you envision a full-time residence or a weekend retreat,

  Christopher Wilson APP Realty

  0 Turtle Ct Unit 375, Winchester, TN 37398
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  /19

  $199,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft

  95 Reid Ln, Winchester, TN 37398

  Charming three-bedroom, two-bath home situated on a beautiful three-quarter acre lot surrounded by mature hardwood trees. This property offers the perfect blend of privacy and convenience with plenty of room for kids, pets, or outdoor entertaining. Inside, you’ll find fresh neutral paint throughout, new flooring, and a spacious kitchen with ample cabinetry and workspace. The desirable

  Christopher Smith Synergy Realty Network, LLC

  95 Reid Ln, Winchester, TN 37398
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  /18

  $79,900

  $5K PRICE DROP

  • Land
  • 6,359 Sq Ft
  • $547,260 per Acre

  0 River Watch Way Unit 365, Winchester, TN 37398

  Motivated Sellers! All reasonable offers considered.Come enjoy all the amenities this Summer ! And the 4th of July fireworks - at Twin Creeks Marina. This level lot is ready for your dream home! Bring the house plans. (The lot next door *365, MLS * is also for sale so you could build on both lots. Located in family-friendly, gated lakeside community, Twin Creeks offers everything you need for

  Amy Rivera Marcoma Realty, Inc.

  0 River Watch Way Unit 365, Winchester, TN 37398
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  /21

  $749,900

  $80K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,738 Sq Ft

  101 Cypress Point Dr, Winchester, TN 37398

  Lakefront Luxury – Priced Well Below Appraised Value. Wake up to peaceful mornings and unwind with breathtaking sunset views over Tim’s Ford Lake, all from your own covered back porch. This stunning home is tucked away in a quiet, sought-after neighborhood with access to a community dock, slip included, offering the perfect balance of privacy, beauty, and connection. Inside, you’ll find a

  Emily Goodgame simpliHOM

  101 Cypress Point Dr, Winchester, TN 37398
• 

  

  /17

  $249,900

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

  70 Woods Edge Rd, Winchester, TN 37398

  Charming 3-Bedroom, 2-Bath Home in a Great Location! This adorable home offers endless potential! Featuring three bedrooms, two baths, and a fenced-in backyard, it’s perfect for anyone looking to add their own personal touch. Conveniently located near the city park, disc golf course, Bass Club, Tim’s Ford Lake, and all the great amenities Winchester has to offer. Whether you’re looking for a

  April Smith John Smith Jr Realty and Auction LLC

  70 Woods Edge Rd, Winchester, TN 37398
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  /62

  $879,000

  $16K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,684 Sq Ft

  73 Cypress Point Dr, Winchester, TN 37398

  Lake Front Living! Located in Cypress Point Subdivision. Step inside to a beautiful foyer that opens into open concept living designed for relaxation and entertaining! The first floor features a screened-in back porch with a gas fireplace perfect for cozy evenings. Adjacent is the open deck perfect for grilling, dinner, soaking in the hot tub and outdoor entertaining. The primary suite is located

  Melissa Stewart Swaffords Property Shop

  73 Cypress Point Dr, Winchester, TN 37398
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  /39

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,490 Sq Ft

  1400 Holders Cove Rd, Winchester, TN 37398

  2.3 +/- acres in country like setting just minutes from the square in Winchester.

  Bj Rigsby Lynch Rigsby Realty & Auction, LLC

  1400 Holders Cove Rd, Winchester, TN 37398
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  /16

  $109,900

  • Land
  • 9,016 Sq Ft
  • $530,918 per Acre

  0 Kayak Way Unit RTC3213420, Winchester, TN 37398

  Ready to build? Corner lot in Twin Creeks with community pool and gated entrance in sight. This lot is directly in front of you when you enter the gate towards Canoe Ct. road.This beautiful lot is flat and ready for your dream home. Located within a short drive by golf cart to a full service marina, restaurant, convenience store, boat slip, and pools. Located minutes from shopping and dining-

  Valerie Wilder Century 21 Coffee County Realty & Auction

  0 Kayak Way Unit RTC3213420, Winchester, TN 37398
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  /7

  $99,900

  • Land
  • 0 Sq Ft

  0 Pontoon Place Unit RTC3129038, Winchester, TN 37398

  Lot 435 One of the few lots left in Twin Creeks Village. Enjoy all the amenities of this community. Restrictions apply.

  Bj Rigsby Lynch Rigsby Realty & Auction, LLC

  0 Pontoon Place Unit RTC3129038, Winchester, TN 37398
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  /6

  $175,000

  • Land
  • 1.04 Acres
  • $168,269 per Acre

  0 Cascade Dr Unit 9, Winchester, TN 37398

  Build your dream home on this spacious 1.04-acre lot located in the highly desirable Stone Field Heights subdivision. This premium homesite is one of the largest parcels in the neighborhood, providing both space and privacy. Situated at the front corner of the subdivision, the property backs up to a beautiful horse farm—ensuring no future development behind you—with breathtaking sunset views

  Steven Koleno Beycome Brokerage Realty, LLC

  0 Cascade Dr Unit 9, Winchester, TN 37398
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  /44

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,045 Sq Ft

  1405 Old Estill Springs Rd, Winchester, TN 37398

  Tucked away on over 3 beautiful acres right in the heart of town, this lovely home feels like your own private retreat while still being only minutes from shopping, dining, and the sparkling waters of Tims Ford Lake. From the moment you pull into the driveway, you can feel the warmth and charm this property offers. Step inside and imagine cozy evenings gathered around the stunning

  Angela Miller John Smith Jr Realty and Auction LLC

  1405 Old Estill Springs Rd, Winchester, TN 37398
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  /100

  $974,900

  $125K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 3,622 Sq Ft

  11 Hammock Dr, Winchester, TN 37398

  This stunning home offers beautiful views and is just steps from Twin Creeks Marina & Resort, with scenic overlooks of Tim’s Ford Lake. Nestled in the heart of Winchester, this location is surrounded by rolling hills, peaceful coves, and sparkling lake waters, creating the perfect blend of relaxation and recreation. The area is celebrated for its welcoming community, laid-back lifestyle, and

  Megan Jones Onward Real Estate

  11 Hammock Dr, Winchester, TN 37398
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  /32

  $327,900

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,358 Sq Ft

  101 N Shephard St, Winchester, TN 37398

  Welcome home to “Tangerine,” a vibrant and inviting residence inspired by the warmth and soul of the classic Tangerine. Nestled within the colorful Terrapin Station subdivision, this thoughtfully designed home offers both personality and modern comfort. Step onto the large covered front porch with striking wood accents and into an open-concept living space filled with natural light. Luxury vinyl

  Eberley Holloway Southern Middle Realty

  101 N Shephard St, Winchester, TN 37398
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  /63

  $2,119,040

  Coming Soon

  • 4 Beds
  • 5.5 Baths
  • 6,160 Sq Ft

  318 N Porter St, Winchester, TN 37398

  Elevated Lake Living. Lakeside Luxury at the Finest! 3 Level Home that Has It All and More. In Gated Boutique Community Close to Downtown Winchester. HOA incl Lawn Mowing, Gate Maintenance, Common Area and Dock Maintenance/Insurance. This Home is 3 Level of Luxury with 3 Private Primary Suites - 1 on the Main Level, and 2 Upstairs- all with Double Vanities, Large Showers, Water Closets, and

  Tara Hays Benchmark Realty, LLC

  318 N Porter St, Winchester, TN 37398
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  /60

  $1,389,900

  • 4 Beds
  • 4 Baths
  • 3,720 Sq Ft

  160 Wakeboard Way, Winchester, TN 37398

  Incredible opportunity to own a well appointed custom designed home. The list price includes a 2019 Cobalt R- 7 luxury Watercraft in mint condition with very low hours - (valued at over $120,000) and your first years boat slip rental at Twin Creeks marina. In this is a home you will find attention to finest details speaks for themselves. Starting with the porcelain pavers at the front entry,

  Angela Privett Benchmark Realty, LLC

  160 Wakeboard Way, Winchester, TN 37398
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  /76

  $357,900

  $22K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,864 Sq Ft

  305 Oak Leaf Cir, Winchester, TN 37398

  This spacious four-bedroom home with a bonus room and three full baths offers a wonderful blend of comfort, character, and opportunity. A detached garage with a versatile room above provides ideal space for a storage or a studio. The backyard is an entertainer’s retreat, featuring an in-ground pool surrounded by a generous deck and framed by a serene wooded backdrop that offers both privacy and

  Hannah Monilaw Better Homes & Gardens Real Estate Heritage Group

  305 Oak Leaf Cir, Winchester, TN 37398
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  /62

  $699,900

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,884 Sq Ft

  64 Blairmont Ct, Winchester, TN 37398

  The Brooklyn Plan is a fan favorite, offering 4 bedrooms and 3 bathrooms with a thoughtfully designed layout. The primary suite and a secondary bedroom are conveniently located on the main floor, ideal for guests or multigenerational living. Upstairs, you’ll find two additional bedrooms, along with a spacious bonus room and a private office hidden behind a custom Murphy door, adding both function

  Mitchell Bowman simpliHOM - The Results Team

  64 Blairmont Ct, Winchester, TN 37398
• 

  

  /5

  $110,000

  $40K PRICE DROP

  • Land
  • 41,382 Sq Ft
  • $115,789 per Acre

  7 Summer Lake, Winchester, TN 37398

  Nice building tract with 3 BR building soil site on .95 acres. This lot is only minutes to Tims Ford Lake & located in the center of all the attractions. Only minutes to the state park, marinas, restaurants, and Jack Daniels Distillery. Located in southern middle Tennessee, this property is 1 1/2 hours to Nashville and 1 hour to Huntsville AL. There is a deeded easement on Lot 8 for access to the

  Greg Sitz Parks Auction & Realty

  7 Summer Lake, Winchester, TN 37398
• 

  

  /23

  $369,900

  • 6 Beds
  • 4 Baths
  • 2,052 Sq Ft

  1316 Old Cowan Rd, Winchester, TN 37398

  INVESTOR SPECIAL! INCLUDES 1316/1318 OLD COWAN RD! Duplex featuring 3BR/2BA units with stainless appliances, tile flooring, and city water and sewer. Strong rental potential in a convenient location just minutes from downtown Winchester. Low‐maintenance finishes and solid layout make this an excellent income‐producing opportunity for any portfolio.

  Daryl Welch Freedom Realty Group

  1316 Old Cowan Rd, Winchester, TN 37398
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  /24

  $135,000

  • Land
  • 28,749 Sq Ft
  • $204,545 per Acre

  0 River Watch Way Unit 524, 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 524, Winchester, TN 37398
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  /2

  $55,000

  $5K PRICE DROP

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

  1533 Rowe Gap Rd Unit 1 (4), Winchester, TN 37398

  1/2 Acre vacant building lot with approval for 3-bedroom septic system. 92' x 238'. Zoned R-1 (single family only, no mobile homes). Otherwise unrestricted. Great lot for house or barn-dominium.

  Thomas Ore Winton Auction & Realty Co.

  1533 Rowe Gap Rd Unit 1 (4), Winchester, TN 37398
• 

  

  /5

  $110,000

  $90K PRICE DROP

  • Land
  • 41,382 Sq Ft
  • $115,789 per Acre

  11 Summer Lake Ct, Winchester, TN 37398

  Nice building tract with 3 BR building soil site on .95 acres. This lot is only minutes to Tims Ford Lake & located in the center of all the attractions. Only minutes to the state park, marinas, restaurants, and Jack Daniels Distillery. Located in southern middle Tennessee, this property is 1 1/2 hours to Nashville and 1 hour to Huntsville AL. There is a deeded easement on Lot 8 for access to the

  Greg Sitz Parks Auction & Realty

  11 Summer Lake Ct, Winchester, TN 37398
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  /86

  $1,575,000

  • 3 Beds
  • 5 Baths
  • 6,300 Sq Ft

  1485 Water Tank Rd, Winchester, TN 37398

  We are introducing this breath taking home crafted on a beautifully wooded 12.1 acres in one of the most desired locations. Meticulously designed and constructed this remarkable traditional residence spans 4000 square feet, offering a seamless concept of traditional and modern floor plan. This home presents 3 bedrooms with 3 ensuite bathrooms and an additional guest half bath, a library, and a

  Sharon Swafford Swaffords Property Shop

  1485 Water Tank Rd, Winchester, TN 37398
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  /58

  $149,900

  • Land
  • 0 Sq Ft

  0 Kayak Way Unit 516, Winchester, TN 37398

  Lake View Lot- On the South Side of Twin Creeks Village and Resort! Imagine Yourself on the Upper Story Watching the Sun Set On The Lake From Your Future Home! Beautiful Lot and READY TO BUILD. LAKE VIEW LOT on the TWIN CREEKS SOUTH SIDE. Very Close to the Largest Twin Creeks Pool, Close to the Serene Side of Tim's Ford Lake, Come Build Your Dream Lake House! HOA cuts the grass, even after you

  Tara Hays Benchmark Realty, LLC

  0 Kayak Way Unit 516, Winchester, TN 37398
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  /4

  $100,000

  • Land
  • 1.71 Acres
  • $58,480 per Acre

  0 Old Clark Rd, Winchester, TN 37398

  Ivy Hankins Southern Middle Realty

  0 Old Clark Rd, Winchester, TN 37398
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  /67

  $1,475,000

  New Construction

  • 4 Beds
  • 6 Baths
  • 4,080 Sq Ft

  86 Simmons Cir, Winchester, TN 37398

  Welcome to lakeside living in the prestegious Fanning Bend community on scenic Tims Ford Lake in Winchester, TN. This newly built, 4 Bed, 4.5 bath home blends timeless design with high-end finishes, while maximizing the gorgeous lake views. The open floor plan features vaulted ceilings, rich hardwoods, and expansive windows that flood the home with natural light. A stunning stone fireplace

  Brandon Bubis Legacy South Brokerage

  86 Simmons Cir, Winchester, TN 37398
• 

  

  /10

  $159,900

  • Land
  • 5.01 Acres
  • $31,916 per Acre

  0 Lynchburg Rd Unit 1, Winchester, TN 37398

  Beautiful 5 acre Tract Ready for You to Build Your Dream Home. Nestled in the heart of Franklin County, perfectly positioned between the charm of Historic Lynchburg, Tim's Ford Lake and State Park Area, with the convenience of Winchester. Property Already Has Three Defined Soils Areas possibility to divide property. Do not miss your chance to own this Tract.

  Troy Stacy Parks Auction & Realty

  0 Lynchburg Rd Unit 1, Winchester, TN 37398
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  /5

  $69,000

  $6K PRICE DROP

  • Land
  • 2.05 Acres
  • $33,659 per Acre

  1533 Rowe Gap Rd Unit 2 (4), Winchester, TN 37398

  2.05 Acre vacant building lot with approval for 5-bedroom septic system. 359' x 257'. Zoned R-1 (single family only, no mobile homes). Otherwise unrestricted. Great lot for house or barn-dominium.

  Thomas Ore Winton Auction & Realty Co.

  1533 Rowe Gap Rd Unit 2 (4), Winchester, TN 37398
• 

  

  /51

  $869,900

  • 3 Beds
  • 2.5 Baths
  • 2,236 Sq Ft

  155 Cypress Point Dr, Winchester, TN 37398

  Welcome to your custom-built dream home on the water, with a community boat dock plus a boat slip. Extensive, detailed ceilings. Solid wood cabinetry with quartz tops and tile showers—primary suite on the main level with a large walk-in closet and entry door to the patio. Thoughtfully designed space with 2x6 construction and a large partially finished bonus room. Luxury vinyl plank and tile

  Thomas Williams Crye-Leike, Inc., REALTORS

  155 Cypress Point Dr, Winchester, TN 37398
• 

  

  /5

  $110,000

  $40K PRICE DROP

  • Land
  • 33,541 Sq Ft
  • $142,857 per Acre

  3 Summer Lake Ct, Winchester, TN 37398

  Nice building tract with 3 BR building soil site on .77 acres. This lot is only minutes to Tims Ford Lake & located in the center of all the attractions. Only minutes to the state park, marinas, restaurants, and Jack Daniels Distillery. Located in southern middle Tennessee, this property is 1 1/2 hours to Nashville and 1 hour to Huntsville AL. There is a deeded easement on Lot 8 for access to the

  Greg Sitz Parks Auction & Realty

  3 Summer Lake Ct, Winchester, TN 37398
• 

  /2

  $89,000

  • Land
  • 11,761 Sq Ft
  • $329,630 per Acre

  612 N Jefferson St, Winchester, TN 37398

  Corner residential building lot just a stone's throw from Tims Ford Lake and the adorable downtown district of Winchester, TN! This lot is just 7 blocks from the public square and 1 mile from the nearest boat launching ramp which is located in the Winchester City Park. This lot also benefits from a variance that was granted to allow for a larger building footprint. This blank canvas is filled

  Thomas Ore Winton Auction & Realty Co.

  612 N Jefferson St, Winchester, TN 37398
• 

  

  /17

  $130,000

  • Land
  • 5.17 Acres
  • $25,145 per Acre

  0 Haddon Ln Unit lot 7, Winchester, TN 37398

  There’s something special about a piece of land that just feels right the moment you step onto it—and this one truly does.This 5-acre property offers the kind of space and stillness that’s getting harder to find. A peaceful pond sits at the heart of the land, creating a natural backdrop for slow mornings, evening sunsets, and everything in between.Build your dream home with city water and

  Trisha Aldrup Tyler York Real Estate Brokers, LLC

  0 Haddon Ln Unit lot 7, Winchester, TN 37398
• 

  

  /72

  $627,781

  • 4 Beds
  • 2.5 Baths
  • 2,893 Sq Ft

  49 Driftwood Ct, 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, Soaking Tub with Tile Accent Wall, and Walk-in Closet. Beautiful White Kitchen with Tile Backsplash, Wall Oven and Sleek Electric Cooktop. Second Bedroom on the Main Level Could also be Used as a Nursery, Office, Formal Dining, Sitting Room,

  Tara Hays Benchmark Realty, LLC

  49 Driftwood Ct, Winchester, TN 37398

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