Winchester, TN Homes for Sale under $500,000

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  /64

  $470,000

  $5K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 3,922 Sq Ft

  309 2nd Ave NW, Winchester, TN 37398

  SELLER OFFERING OWNER FINANCING AT 5.75% — An ideal income-producing property just over a block from downtown Winchester, provides a rare opportunity for buyers seeking investment property in Tennessee with flexibility for different uses. Built in 1917, this historic, commercially zoned 5-bedroom, 2-bath residence includes approximately 3,922 sq ft on a .34-acre lot in the heart of Winchester.

  Robert Duncan eXp Realty

  309 2nd Ave NW, Winchester, TN 37398
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  /31

  $499,000

  $46K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,276 Sq Ft

  23 Skidmore Ln, Winchester, TN 37398

  All-brick home with stunning mountain views, a detached 3-car garage with bonus space above, and nearly an acre of level country living just minutes from Winchester. Situated on a beautiful corner lot just minutes from Winchester, this all-brick home offers over 2,200 square feet of living space with stunning countryside and mountain views. Featuring 3 bedrooms, 2.5 baths, a dedicated office, and

  Ashley Nelson Franklin County Realty

  23 Skidmore Ln, Winchester, TN 37398
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  /15

  $230,000

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

  0 Kayak Way Unit 489, Winchester, TN 37398

  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 of the

  Felicia Wright Leading Edge Real Estate Group

  0 Kayak Way Unit 489, Winchester, TN 37398
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  /64

  $449,900

  Open House 9/20 $47K 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
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  /41

  $349,900

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,640 Sq Ft

  205 Houghton Dr, Winchester, TN 37398

  Great one-level floor plan featuring two primary suites located on opposite ends of the home—perfect for privacy and flexibility. This home offers abundant storage throughout, including an oversized utility room with a walk-in pantry. A heated and cooled basement provides additional storage space or could serve as a potential storm shelter. Hardwood and tile flooring run throughout the main

  Danielle Wolff Holland Coldwell Banker Southern Realty

  205 Houghton Dr, Winchester, TN 37398
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  /18

  $475,000

  • Land
  • 1.27 Acres
  • $374,016 per Acre

  0 2nd Ave SE, Winchester, TN 37398

  Rare opportunity to acquire development-ready waterfront land for sale in Winchester, TN with flexible R3A zoning, dual road access, and strong residential development potential on Boiling Fork Creek with access to Tims Ford Lake. This 1.27-acre tract in Franklin County offers level topography, scenic water views, and a highly desirable location just minutes from downtown Winchester and the

  Robert Duncan eXp Realty

  0 2nd Ave SE, Winchester, TN 37398
• 

  

  /13

  $324,000

  • 3 Beds
  • 2.5 Baths
  • 2,047 Sq Ft

  173 Country Club Terrace, Winchester, TN 37398

  Lovely neighborhood! Landscaping in the flower beds to be tidied up and shrubs to be pruned. 'Selling As Is".

  Sharon Swafford Swaffords Property Shop

  173 Country Club Terrace, Winchester, TN 37398
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  /56

  $500,000

  Open Sun 1PM - 3PM

  • 6 Beds
  • 4 Baths
  • 3,158 Sq Ft

  109 Carter Farris Ln, Winchester, TN 37398

  This charming country home has been lovingly maintained and cared for by one family since it was built. Located in one of Franklin County's most sought-after countryside settings, the mountains, lake, and shopping are all close by. The owners have spared no expense in making sure that the home has zero deferred maintenance and is entirely move-in ready for its next owner. Situated on a spacious

  Wade Trammell Keller Williams Realty

  

  109 Carter Farris Ln, Winchester, TN 37398
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  /5

  $250,000

  • Land
  • 1.24 Acres
  • $201,613 per Acre

  9 Summer Lake Ct, Winchester, TN 37398

  Nice building tract with 3 BR building soil site on 1.24 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 5 for access to

  Greg Sitz Parks Auction & Realty

  9 Summer Lake Ct, Winchester, TN 37398
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  /53

  $299,900

  • 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
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  /40

  $320,000

  $80K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  667 Maple Bend Rd, Winchester, TN 37398

  Close to the Fairview Boat Ramp.Fantastic 3.5 acres with mature trees, abundant wildlife, and privacy. Property extends 75 feet into woods. Room for a Garden or a Mini Farm Home is a 2 bedroom 1.5 half baths. Original Septic Permit is for a 3 Bedroom home. Room to Expand. New Roof and HVAC. 30x30 Detached Garage/shop with Wood Burning Stove or use the Propane Heater. 2 Metal Sheds for Storage.

  Pam Ford Benchmark Realty, LLC

  667 Maple Bend Rd, Winchester, TN 37398
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  /36

  $315,000

  New Construction $10K PRICE DROP

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

  1563 Paynes Church Rd, Winchester, TN 37398

  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 host BBQ's, Garden or let the pups run & play! Take in the

  Kasidy Lowe Compass Tennessee, LLC

  1563 Paynes Church Rd, Winchester, TN 37398
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  /49

  $369,900

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

  1111 Holders Cove Rd, Winchester, TN 37398

  **Double lot with large shop** This beautiful, well-maintained brick home is convenient to everywhere - less than 1.5 miles from downtown Winchester - a mile from the Country Club -1.2 miles from the Hospital and 2 miles from Food City! It's perfectly positioned on a desirable corner lot and includes a second lot as well! Offering 3 bedrooms and 1.5 baths, this home combines timeless charm with

  Sean Crabtree Blue Door Realty Group

  1111 Holders Cove Rd, Winchester, TN 37398
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  /40

  $374,900

  • 3 Beds
  • 2 Baths
  • 1,657 Sq Ft

  95 Luttrell Dr, Winchester, TN 37398

  Beautifully maintained 3-bedroom, 2-bath home offering a spacious split-bedroom, open-concept floor plan with custom kitchen cabinetry, abundant storage, and an inviting living area. The primary suite features a tray ceiling, dual walk-in closets, and a private bath. Relax in the new two-person hot tub (which conveys) while enjoying beautiful views of Tims Ford Lake. A unique bonus is the vacant

  Thomas Ore Winton Auction & Realty Co.

  95 Luttrell Dr, Winchester, TN 37398
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  /27

  $349,999

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,548 Sq Ft

  131 Charlotte Dr, Winchester, TN 37398

  Bring Offers! Welcome Home!! Such a cute, well designed and spaciously laid out home that proudly boasts of 1,548 sq ft of comfortable living space!! The home welcomes you through the foyer into the roomy Living Room with a gas fireplace and custom tilework. The hardwood floors throughout this home are so beautiful and compliment every room only to add to the elegance of this beautifully designed

  Landon Keller Century 21 Volunteer Realty

  131 Charlotte Dr, Winchester, TN 37398
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  /83

  $399,900

  • 2 Beds
  • 2 Baths
  • 1,450 Sq Ft

  924 Cline Ridge Rd, Winchester, TN 37398

  Enjoy the best of Tennessee living in this charming lakefront home nestled on 0.78± acres on Tims Ford Lake! Offering approximately 1,450 square feet of comfortable living space, oversized decks and porches this property combines peaceful country surroundings with convenient access to outdoor recreation.Inside, you'll find a spacious layout featuring an inviting living area with Panoramic

  Dayla Bray Keller Williams Russell Realty & Auction

  924 Cline Ridge Rd, Winchester, TN 37398
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  /37

  $429,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,157 Sq Ft

  109 Oak Park, Winchester, TN 37398

  SELLER IS OFFERING $15,000 TOWARDS CLOSING COSTS OR RATE BUY DOWN!! Step into this beautifully renovated 1950s ranch where timeless charm meets modern comfort. This move-in ready home features 3 bedrooms and 2 full bathrooms, thoughtfully updated throughout. The spacious great room is the heart of the home, highlighted by the original stone fireplace that creates a warm and inviting atmosphere

  Penny Bowen Bowen Signature Properties

  109 Oak Park, Winchester, TN 37398
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  /36

  $315,000

  New Construction $10K PRICE DROP

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

  1585 Paynes Church Rd, Winchester, TN 37398

  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 host BBQ's, Garden or let the pups run & play! Take in the

  Kasidy Lowe Compass Tennessee, LLC

  1585 Paynes Church Rd, Winchester, TN 37398
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  /15

  $354,500

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,797 Sq Ft

  145 Murray Lake Dr, Winchester, TN 37398

  Welcome to this beautiful 3 br 2 ba brick home located in the areas most desirable subdivision. This home features an inviting open floor plan perfect for entertaining or everyday living. You'll love the gorgeous HW floors, custom cabinetry, and abundant counterspace. The oversize laundry room provides additional convenience while the huge closets ensure plenty of organization. The huge primary

  Chris Hawkersmith Lynch Rigsby Realty & Auction, LLC

  145 Murray Lake Dr, Winchester, TN 37398
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  /79

  $455,000

  $5K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft

  106 Chattin St, Winchester, TN 37398

  Welcome home to this beautifully remodeled all-brick ranch offering the convenience of one-level living in one of Winchester’s most sought-after lake communities. Located just a block from a boat ramp, you’ll enjoy easy access to the lake & all the recreation it has to offer. Step inside to an inviting open floor plan designed for comfortable living & entertaining. The stunning newly remodeled

  Amberly (Abbi) Tomme Legion Realty

  106 Chattin St, Winchester, TN 37398
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  /8

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  80 Tanya Terrace, Winchester, TN 37398

  Welcome Home! Check out this well-maintained 3 bedroom, 2 bath home that has so much to offer! Convenient to Highway 64 and minutes away from Twin Creeks. This home comes with a large fenced in back yard in a quiet neighborhood, built in 2016 with 1,400 square foot of living space and a two-car garage. More Pictures Coming Soon!Need 24 Hour Notice to Show

  Daniel Prince John Smith Jr Realty and Auction LLC

  80 Tanya Terrace, Winchester, TN 37398
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  /41

  $269,900

  $30K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,373 Sq Ft

  102 Oak Park, Winchester, TN 37398

  Make plans now to see this extensively renovated home with a FULL basement in the heart of Winchester! Sitting on a huge corner lot and surrounded by mature shade trees, there is still room to expand. Beautifully renovated inside and out, some of the major updates include a new roof, new Hardie Board siding, new heat/air system, new plumbing, new electric, new water heater, new windows, new

  Shelia Lunsford Benchmark Realty, LLC

  102 Oak Park, Winchester, TN 37398
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  /24

  $225,000

  • 3 Beds
  • 2.5 Baths
  • 2,146 Sq Ft

  1325 Joyce Ln, Winchester, TN 37398

  3-bedroom, 2.5 bath brick house with kitchen, dining area, utility room, and additional flex room. Home features a split bedroom concept with oversized master suite, attached carport, and nice back deck. Approximately 2146 sq. ft. living space. Sitting on 0.62-acre lot. Great investment or starter home!

  Thomas Ore Winton Auction & Realty Co.

  1325 Joyce Ln, Winchester, TN 37398
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  /24

  $473,000

  $27K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,067 Sq Ft

  615 Lakeview Way, Winchester, TN 37398

  SELLER NOW OFFERING $5000 TOWARD UPDATES OF BUYER'S CHOICE AT THE CLOSING TABLE!! Seller says to bring an offer!! They are ready to sell!! This distinguished residence at 615 Lakeview Way offers a rare blend of timeless elegance and everyday comfort within the desirable lakefront subdivision of Winchester. Set on a serene, park-like 1 acre corner lot, the 3,067-square-foot home welcomes you with

  Landon Keller Century 21 Volunteer Realty

  615 Lakeview Way, Winchester, TN 37398
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  /60

  $499,000

  $31K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,266 Sq Ft

  44 Hammock Dr, Winchester, TN 37398

  Beautiful Twin Creeks home with lake views, just one block from the water! This stunning 3-bedroom, 2.5-bath home with a 2-car garage offers an inviting open-concept floor plan featuring custom cabinetry, detailed millwork, a gorgeous stone fireplace, and abundant natural light throughout. Step outside to a fully fenced backyard with a covered concrete patio perfect for relaxing, entertaining, or

  Michelle Sampson Benchmark Realty, LLC

  44 Hammock Dr, Winchester, TN 37398
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  /28

  $259,000

  • Land
  • 33,541 Sq Ft
  • $336,364 per Acre

  0 Twilight Dr Unit 108, Winchester, TN 37398

  This cleared lakeview lot sits in Dripping Springs, an established Winchester subdivision with community boat dock and ramp access — so you're on the water the same day you close.The homesite is already cleared and ready for construction, with mature hardwoods along the rear property line for privacy and shade. Soil testing is complete and the lot is permitted for a three-bedroom septic

  Alexander Brandau Aperture Global

  0 Twilight Dr Unit 108, Winchester, TN 37398
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  /36

  $235,000

  New Construction $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,268 Sq Ft

  62 Modena Place, Decherd, TN 37324

  New Price!!! Smart Layout! Vaulted ceiling Great Room opens to privacy fenced backyard safe place for kids with concrete patio great for grilling. Master bedroom suite enjoys a full private bath and walk in closet. Split floorplan puts Bedroom two and Bedroom three are on the opposite side of the home. Spacious and open living room with lots of natural sunlight. Laundry/pantry right off kitchen.

  Sharon Swafford Swaffords Property Shop

  62 Modena Place, Decherd, TN 37324
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  /29

  $350,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,886 Sq Ft

  67 Lake Ln, Winchester, TN 37398

  Price Improvement! Owners are offering $3,000 for any updates!Welcome to 67 Lake Ln. in Winchester! This beautifully maintained 3-bedroom, 2-bath home sits on nearly an acre and offers the perfect blend of comfort, convenience, and outdoor living. The open-concept kitchen and living area create a spacious, inviting atmosphere ideal for entertaining or everyday life. This home also

  Brandy Scott Winton Auction & Realty Co.

  67 Lake Ln, Winchester, TN 37398
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  /30

  $399,000

  $50K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 3,560 Sq Ft

  3754 Aedc Rd, Winchester, TN 37398

  NEW, IMPROVED price on prime real estate in Franklin County!! With over 600' of road frontage on AEDC Rd and next door to Scenic View Golf Course, 3754 AEDC Rd boasts TWO viable dwellings, along with 9.57 acres of picturesque farm land, complete with panoramic views of the mountains. Build your dream home or develop the parcel into smaller lots. Rehab the dwellings to have the perfect mini farm.

  Adam Brock Canopy Real Estate

  3754 Aedc Rd, Winchester, TN 37398
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  /49

  $455,000

  New Construction Open Sat 1PM - 3PM $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,543 Sq Ft

  201 Lookout Dr, Winchester, TN 37398

  Welcome to this meticulously designed new home! The residence features three spacious bedrooms and two bathrooms, along with a supplemental room with a half bath. It includes upscale features like top-of-the-line stainless steel appliances, custom-built expansive wardrobes, and an exquisite coffered ceiling in the main living area. Through precise craftsmanship and the use of premium materials,

  Mena Shaker Dream Homes Realty

  201 Lookout Dr, Winchester, TN 37398
• 

  

  /21

  $340,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  117 Carol Cir, Winchester, TN 37398

  3 BR, 2 bath home, all on a 1/2 acre in desirable neighborhood! Hardwood floors in main area and main bedroom. With beautiful cabinetry in the kitchen, stainless appliances and a 6-burner stove. Large jack/jill bath w/double vanities and walk-in closets throughout each bedroom of the house. Large master bedroom, with a huge closet, double vanity sink, tile shower, and large whirlpool tub.

  Daniel Prince John Smith Jr Realty and Auction LLC

  117 Carol Cir, Winchester, TN 37398
• 

  /2

  $325,000

  New Construction

  • 1,672 Sq Ft

  1012 Hunt St, Winchester, TN 37398

  Investors, take notice! 1012/1014 Hunt St, Winchester, TN! This new-construction duplex offers an excellent opportunity to add a modern, low-maintenance property to your portfolio in a convenient Winchester location. Each unit features 2 bedrooms and 2 full bathrooms, an attractive floor plan for renters seeking comfortable, functional living space. Both units offer desirable modern finishes,

  Daryl Welch Freedom Realty Group

  1012 Hunt St, Winchester, TN 37398
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  /16

  $298,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  23 Woods Edge Rd, Winchester, TN 37398

  A welcoming living space boasts a stunning double-opening fireplace, perfect for cozy evenings spent with family and friends. The abundant natural light streaming through replacement windows creates an airy ambiance that will make you feel right at home. The dining room conveniently opens to an outdoor patio through sliding doors, making it an entertainer's dream. Imagine hosting gatherings with

  Sharon Swafford Swaffords Property Shop

  23 Woods Edge Rd, Winchester, TN 37398
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  /32

  $230,000

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft

  525 Sharp Springs Rd, Winchester, TN 37398

  Whether you're buying your very first home, looking to simplify life with less maintenance, or searching for the perfect vacation retreat, this charming 2-bedroom, 2-bath home checks every box.Thoughtfully designed with comfortable living spaces and a functional layout, this home offers the perfect balance of convenience and comfort. Its unbeatable location near Tims Ford Lake and Twin

  Madeleine Duncan Steve Jernigan Realty

  525 Sharp Springs Rd, Winchester, TN 37398
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  /47

  $355,000

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft

  79 Charlotte Dr, Winchester, TN 37398

  Welcome home to this beautifully remodeled 3-bedroom, 2-bath ranch offering the ease of all one-level living & stylish updates throughout. From the moment you step inside, you’ll appreciate the fresh, modern feel created by brand-new luxury vinyl plank flooring throughout the home & new tile flooring in both bathrooms. The spacious living area is warm & inviting, offering the perfect place to

  Amberly (Abbi) Tomme Legion Realty

  79 Charlotte Dr, Winchester, TN 37398
• 

  

  /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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  /52

  $399,900

  • 3 Beds
  • 2 Baths
  • 2,260 Sq Ft

  810 Cumberland Dr, Winchester, TN 37398

  Welcome to 810 Cumberland Dr.! This charming 3-bedroom, 2-bath home offers 2,260 square feet of living space in a beautiful, established Winchester setting. Thoughtfully updated throughout, the home features all-new windows, a new HVAC system with gas heat, new dishwasher, sink, disposal and microwave, professionally cleaned ductwork, fresh interior and exterior paint, new LED recessed lighting

  Matt Sargent Matt Sargent Homes

  810 Cumberland Dr, Winchester, TN 37398
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  /33

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 3,960 Sq Ft

  401 E Petty Ln, Winchester, TN 37398

  Welcome to 401 East Petty Lane, where classic charm meets central convenience. Nestled in a peaceful neighborhood on an oversized lot, this timeless single-level ranch provides an exceptional location with effortless access to local work commutes, shopping, dining, and entertainment. Outdoor living is a delight on the private stone patio, which overlooks the expansive yard and serves as an ideal

  Wade Trammell Keller Williams Realty

  

  401 E Petty Ln, Winchester, TN 37398
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  /44

  $389,900

  Open House 9/19 $40K 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
• 

  

  /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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