Winchester, TN Homes for Sale under $500,000

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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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  /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

  $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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  /30

  $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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  /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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  /23

  $364,900

  $5K PRICE DROP

  • 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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  /29

  $489,900

  • 3 Beds
  • 2 Baths
  • 2,116 Sq Ft

  647 Golf Shores Dr, Winchester, TN 37398

  Welcome to this beautiful brick home offering over 2,000 sq ft of living space in one of the most desirable setting around. This home rests on an amazing lot connecting to Tim's Ford State Park with a short hike to the lake. This property provides direct access to hiking trails and the lake, making it perfect for outdoor enthusiast who enjoy fishing, hiking or nature walks. Inside you will enjoy

  Chris Hawkersmith Lynch Rigsby Realty & Auction, LLC

  647 Golf Shores Dr, Winchester, TN 37398
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  /25

  $469,900

  • 3 Beds
  • 2 Baths
  • 1,817 Sq Ft

  172 Lookout Dr, Winchester, TN 37398

  Better than new with tons of builder and seller upgrades in a beautiful, gated community! This gem is located only 1/2 mile from a public boat ramp on the ever-popular Tims Ford Lake. You'll love the grand entrance with soaring ceilings, 8 foot doors throughout, tons of natural light, quartz countertops, and the huge custom pantry. The laundry room, with custom cabinets and folding station,

  Renee Delbridge Benchmark Realty, LLC

  172 Lookout Dr, Winchester, TN 37398
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  /70

  $450,000

  • 3 Beds
  • 3 Baths
  • 2,629 Sq Ft

  314 4th Ave NW, Winchester, TN 37398

  Charming Southern Elegance Awaits You! Step into a world of timeless beauty and modern luxury with this stunning turn-of-the-century home, meticulously renovated to blend classic charm with contemporary comfort. The heart of the home is the spacious kitchen, featuring exquisite quartz and granite countertops that will inspire your culinary adventures. Whether hosting intimate dinners or grand

  Sharon Swafford Swaffords Property Shop

  314 4th Ave NW, Winchester, TN 37398
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  /25

  $395,000

  • Land
  • 14,374 Sq Ft
  • $1,196,970 per Acre

  0 Hickory Point Dr Unit 2, Winchester, TN 37398

  Discover the perfect setting for your dream home in the sought‐after Cline Ridge subdivision on Tims Ford Lake. This gorgeous lake lot offers the ideal blend of privacy, convenience, and year‐round recreation. You’ll enjoy easy ACCESS YOUR OWN PRIVATE DOCK on Out Lot A, just a short drive from your homesite—perfect for fishing, boating, or simply relaxing by the water. Located only minutes from

  Daryl Welch Freedom Realty Group

  0 Hickory Point Dr Unit 2, Winchester, TN 37398
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  /50

  $373,500

  $21K PRICE DROP

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

  204 8th Ave SE, Winchester, TN 37398

  New Roof, just installed!! Motivated sellers. Bonus Room above the garage is not included in the square feet. Lots of living space with 3 bedrooms & 3 full bathrooms (2 are Master suites with bathrooms). There are separate living room and formal dining room, separate office/den, screened patio, open patio, and 2 outbuildings for extra storage. Whole house standby Generac generator goes with the

  Sharon Swafford Swaffords Property Shop

  204 8th Ave SE, Winchester, TN 37398
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  /55

  $295,000

  • 3 Beds
  • 2 Baths
  • 1,544 Sq Ft

  171 Raspberry Dr, Winchester, TN 37398

  New Roof 2025! Welome Home~ This 3-bedroom, 2-bath home offers 1,544 sq. ft. of thoughtfully designed living space with an inviting open-concept layout. Features include rich walnut flooring, a spacious primary suite with a walk-in closet, beautifully stained wood kitchen cabinetry, and a large 2-car garage. Step outside to enjoy the fully fenced backyard complete with a 12×12 deck — perfect for

  Sharon Swafford Swaffords Property Shop

  171 Raspberry Dr, Winchester, TN 37398
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  /75

  $499,900

  • 4 Beds
  • 3.5 Baths
  • 2,260 Sq Ft

  805 N Jefferson St, Winchester, TN 37398

  With T ims Ford Lake just across the street, be prepared to love the LAKE VIEWS year round from the front porch! GREAT location with all the conveniences nearby -- Twin Creeks Marina, restaurants, shopping on the town Square and numerous boat ramps nearby. Wonderfully open floor plan! Primary downstairs; three bedrooms and open flex space at top of stairs. Bedroom 2 upstairs with its own private

  Shelia Lunsford Benchmark Realty, LLC

  805 N Jefferson St, Winchester, TN 37398
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  /32

  $340,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,038 Sq Ft

  61 Brookfield Cir, Winchester, TN 37398

  If you’ve been waiting on a solid, beautiful brick home with REAL rooms and space for everyone... this is it. This one is not your typical open concept. You get those traditional, defined spaces that just make sense... a layout that gives you privacy, function, and room to actually live. The rooms are BIG, not cramped, not cut up... just good, comfortable space. You’ve got sitting areas on both

  Fhonda Hatmaker eXp Realty

  61 Brookfield Cir, Winchester, TN 37398
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  /26

  $224,500

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,326 Sq Ft

  208 Lillian St, Winchester, TN 37398

  $15,000 PRICE REDUCTION! Welcome home to this charming rambler in the City of Winchester. This home is bursting with character and sits on a large +/- 0.48-acre lot on a quiet street. Walking distance to the historic Winchester Square and Tim’s Ford Lake. Hardwood floors, new kitchen counters, and a fully fenced back yard for your four-legged friends. Mature trees line the back and side yard.

  Cramer Foster Lynch Rigsby Realty & Auction, LLC

  208 Lillian St, Winchester, TN 37398
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  /42

  $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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  /75

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,149 Sq Ft

  129 Meredith Ln, Winchester, TN 37398

  Looking for a home that's anything but ordinary? This one-of-a-kind property combines space, versatility, and outdoor living on 2 beautiful acres with lake access, creating the perfect place to live, work, and play. Inside, you'll find a spacious layout highlighted by an impressive primary suite that serves as your own private retreat. Need a place to work from home? The dedicated office offers

  Angela Miller John Smith Jr Realty and Auction LLC

  129 Meredith Ln, Winchester, TN 37398
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  /21

  $339,999

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,683 Sq Ft

  38 Murray Lake Dr, Winchester, TN 37398

  Motivated Seller Here!! Welcome home to this 1 owner and well took care of home that is Move In Ready. It boasts of split bedroom floor plan of 2 bedrooms with a 3rd that is a bedroom by definition and 2 nice bathrooms. The master suite has dual vanities and a spacious walk-in closet and shower too. The roof was replaced in 2023. The home has a spacious living room, kitchen, and dining area. Also

  Landon Keller Century 21 Volunteer Realty

  38 Murray Lake Dr, Winchester, TN 37398
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  /67

  $474,900

  • 4 Beds
  • 2.5 Baths
  • 2,564 Sq Ft

  65 Campfire Ct, Winchester, TN 37398

  This beautiful 4BR/2.5 bath townhome in Twin Creeks Village on Tims Ford Lake offers generous living space -- ideal for guests, hobbies, or weekend gatherings. NEW FLOORING in Primary bedroom and closets (no carpet)! Bedroom 4 offers options...either as a large bunk room or an amazing bonus room...whatever serves you best! Featuring a spacious, open floor plan and a delightful screened porch,

  Shelia Lunsford Benchmark Realty, LLC

  65 Campfire Ct, Winchester, TN 37398
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  /62

  $435,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,971 Sq Ft

  185 Favre Cir, Winchester, TN 37398

  Welcome to this beautiful well maintained all brick, one story home located in the desirable Chattin Farm Subdivision. This property boasts an attached two-car garage and a spacious detached garage with electricity. The interior features vaulted ceilings and genuine hardwood floors throughout. The primary suite includes a luxurious soaking tub and a walk in shower. The kitchen features granite

  Kimberly Rudd Keller Williams Russell Realty & Auction

  185 Favre Cir, Winchester, TN 37398
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  /59

  $495,000

  • 3 Beds
  • 3 Baths
  • 2,230 Sq Ft

  111 Campfire Ct, Winchester, TN 37398

  Experience lakeside luxury at its finest in this FULLY FURNISHED, turnkey corner townhome at 111 Campfire Ct—offering elevated design, premium upgrades, and true move-in-ready living. Featuring 3 bedrooms, 3 bathrooms, and a bonus room. This home blends comfort, function, and high-end entertainment. Step inside to a warm, inviting open concept interior with a cozy gas fireplace, fully insulated

  Alexandra Watts Southern Middle Realty

  111 Campfire Ct, Winchester, TN 37398
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  /59

  $269,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,866 Sq Ft

  1010 N High St, Winchester, TN 37398

  Lake view, location, and space—this one has it all! Welcome to 1010 North High Street, ideally situated just across the bridge from the lake and the Bass Club with boat ramp access, and only minutes from the square. This 3-bedroom, 2-bath home offers over 1,800 sq ft of convenient one-level living, featuring a huge rec room perfect for entertaining, game days, or a home theater setup. Enjoy

  Christopher Smith Synergy Realty Network, LLC

  1010 N High St, Winchester, TN 37398
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  /27

  $215,000

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  1508 Clark St, Winchester, TN 37398

  3 bed/2 bath home conveniently located near Nissan, downtown Winchester, shopping, dining, and more! Enjoy a fenced-in backyard that's perfect for pets, entertaining, or simply relaxing outdoors. Whether you're a first-time buyer, downsizing, or looking for an investment opportunity, this property is one you'll want to see! Priced below recent appraisal = instant equity! Receive 1% towards

  Timothy Crabtree Benchmark Realty, LLC

  1508 Clark St, Winchester, TN 37398
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  /39

  $300,000

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,822 Sq Ft

  111 Dogwood Ln, Winchester, TN 37398

  Updated brick ranch single story, in the Scenic Heights subdivision, featuring 1822 square feet with three bedrooms, 1 bath, hardwood floors, central air and heat. This large corner lot has a BIG backyard with fully fenced backyard, separate storage building, five parking spaces, close to downtown, minutes from Tims Ford Lake. Updates include HVAC and hot water heater less 5 years old, roof is

  Susan Holmes University Realty

  111 Dogwood Ln, Winchester, TN 37398
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  /5

  $468,000

  New Construction $22K PRICE INCREASE

  • 4 Beds
  • 3 Baths
  • 2,126 Sq Ft

  0 Sharp Springs Rd Unit RTC3259940, Decherd, TN 37324

  Your new home is officially underway! Construction has started on this beautiful new build sitting on a spacious .72-acre lot with room to enjoy. This thoughtfully designed home offers the features everyone is looking for: open living spaces, vaulted ceilings, a split-bedroom layout, a beautiful kitchen design with a large island, covered porches, and a bonus room for that extra space you always

  Fhonda Hatmaker eXp Realty

  0 Sharp Springs Rd Unit RTC3259940, Decherd, TN 37324

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