Winchester, TN Homes for Sale with Acreage

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  $999,500

  $251K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 6,803 Sq Ft

  2124 Boswell Rd, Winchester, TN 37398

  BRAND NEW ROOF!* W/ Transferable Warranty. Ask Me About Our 1% Preferred Lender Credit To Be Used For Closing Costs Or Rate Buydown* *COMPLIMENTARY Home Warranty*Just MINUTES from Tim's Ford Lake! When Your Custom-Built Home Is Masterfully Crafted By A Brilliant Engineer, You’re Investing In A Home Designed For Generations. Set On An Expansive 2.6-Acre Estate, This Property Combines

  Robert Evanoff Berkshire Hathaway HomeServices Woodmont Realty

  2124 Boswell Rd, Winchester, TN 37398
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  $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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  $412,000

  $18K 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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  $315,000

  $20K 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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  $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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  $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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  $1,475,000

  $100K PRICE DROP

  • 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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  $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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  $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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  $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
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  $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
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  $845,000

  • 3 Beds
  • 2.5 Baths
  • 2,411 Sq Ft

  150 Edie Mae Ln, Winchester, TN 37398

  BRING YOUR HORSES! PLUS LAKE ACCESS Nestled on 9 scenic acres adjacent to Tims Ford Lake, this stunning modern home offers the perfect blend of comfort, style and tranquility.Built just 6 years ago, the residence features a bright, open floor plan designed for both everyday living and entertaining.The home boasts 3 spacious. bedrooms a huge bonus room, and 2 1/2 beautifully appointed bathrooms.

  Sheila Bair Century 21 Coffee County Realty & Auction

  150 Edie Mae Ln, Winchester, TN 37398
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  $118,000

  $2K PRICE DROP

  • Land
  • 2.32 Acres
  • $50,862 per Acre

  0 Old Estill Springs Rd Unit RTC3180497, Winchester, TN 37398

  An incredible opportunity to design and build your dream home or a weekend gateway nestled in a peaceful and well established neighborhood tin Winchester, TN. This spacious lot offers the perfect balance of peaceful country setting, privacy, convenience, and natural beauty.

  Erika Solano Reliant Realty ERA Powered

  0 Old Estill Springs Rd Unit RTC3180497, Winchester, TN 37398
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  $1,500,000

  • Land
  • 19.58 Acres
  • $76,609 per Acre

  405 Sharp Springs Rd, Winchester, TN 37398

  Prime Residential Development Tract – Inside the City Limits of Winchester. This exceptional 19.5± acre development tract presents a rare, in-town opportunity for residential builders and developers seeking scale, location, and long-term upside. The property is strategically located behind Watson Funeral Home and directly adjacent to the established lakefront community of Winchester Village,

  Thomas Ore Winton Auction & Realty Co.

  405 Sharp Springs Rd, Winchester, TN 37398
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  $150,000

  $40K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,580 Sq Ft

  2077 Holders Cove Rd, Winchester, TN 37398

  This home is a perfect opportunity for those looking to remodel. It does need significant repairs, offering a blank slate to create your dream home. The spacious 2-acre lot adds potential, giving you room to create your space inside and out. This home offers 4 rooms, one of which is ideal as a home office.

  Andrea Cruz John Smith Jr Realty and Auction LLC

  2077 Holders Cove Rd, Winchester, TN 37398
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  $455,000

  $10K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,420 Sq Ft

  71 David Crockett Hwy, Winchester, TN 37398

  Completely remodeled and move-in ready, this stunning home offers the perfect blend of modern upgrades and functional space. Situated on approximately one acre, this property features 5 bedrooms, an office, a spacious recreation/game room upstairs, and a 2-car garage. Inside, you’ll find beautiful new flooring throughout, custom cabinetry, granite countertops, and stylish finishes at every turn.

  Eberley Holloway Southern Middle Realty

  71 David Crockett Hwy, Winchester, TN 37398
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  $325,000

  New Construction $25K PRICE DROP

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

  1543 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

  1543 Paynes Church Rd, Winchester, TN 37398
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  $143,000

  $45K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 880 Sq Ft

  6004 Lynchburg Rd, Winchester, TN 37398

  Project in process ready to be completed on 1.5 acres. Great location between Winchester and Lynchburg and less than 10 minutes from Tim's Ford State Park,Tim's Ford Damn and the Elk River. The prebuilt home is brand new and has been wired and plumbed. The rest needs to be finished. Was constructed to be a 2 bedroom and 2 bath but can be modified.

  Josh Cook Benchmark Realty, LLC

  6004 Lynchburg Rd, Winchester, TN 37398
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  $134,900

  • Land
  • 5.16 Acres
  • $26,143 per Acre

  0 Haddon Ln Unit 8, Winchester, TN 37398

  Build your dream home in the peaceful Metcalf Crossings community, where quiet country living meets everyday convenience. This beautiful 5.16 acre tract offers a perfect blend of open space and privacy surrounded by scenic views. The property has already been surveyed and soil mapped, with city water and power available at the road and room for your own septic system. Gentle topography and

  Dennis Sanders eXp Realty

  0 Haddon Ln Unit 8, Winchester, TN 37398
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  $649,900

  New Construction

  • 3 Beds
  • 4 Baths
  • 3,706 Sq Ft

  766 Awalt Dr, Winchester, TN 37398

  New custom built 3 BR home in a fabulous area close to Tims Ford Lake. This spacious home features a large master suite with a separate tub and tile shower, double vanities, and a large walk in closet. The kitchen is equipped with all new stainless appliances, stove and range are both gas, plenty of custom cabinets, and large island for extra counter space. This home also has a large Florida

  Greg Sitz Parks Auction & Realty

  766 Awalt Dr, Winchester, TN 37398
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  $184,999

  $37K PRICE DROP

  0 Holders Cove Rd, Winchester, TN 37398

  Sellers will cut in driveway with acceptable offer. +/- 7.77 Acre tract in beautiful Holders Cove! This piece of land has mountain views to the east and south and is shovel ready with access to city water, power, and suitable soils for a septic system. This is your chance to own a slice of heaven in the country yet only a short 10 minute drive the historic downtown square in Winchester! Enter

  Pelatiah Prince Winton Auction & Realty Co.

  0 Holders Cove Rd, Winchester, TN 37398

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