Winchester, TN Homes for Sale under $500,000

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  /54

  $439,000

  • 4 Beds
  • 2.5 Baths
  • 2,660 Sq Ft

  58 Island Way, Winchester, TN 37398

  Low maintenance living meets lake life luxury in this beautifully designed townhome tucked inside a gated community loaded with amenities! Whether you're looking for a full-time residence or the perfect weekend escape, this one checks all the boxes. Step inside to find a spacious layout featuring a primary suite on the main level, offering convenience and comfort. The spa-like bath is your

  Angela Miller John Smith Jr Realty and Auction LLC

  58 Island Way, Winchester, TN 37398
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  /10

  $255,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,575 Sq Ft

  110 Allen Dr, Winchester, TN 37398

  Great investment property, located in cul de sac. All brick! Two units with central heating and cooling, one with a brand new unit. Large, private back yard. Located close to grocery store, shopping, restaurants, etc. Great return on your money. Both units are rented at 875.00 and 950.00.

  Curtis Benchmark Realty, LLC

  110 Allen Dr, Winchester, TN 37398
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  /62

  $444,000

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,431 Sq Ft

  90 Owl Hollow Ln, Winchester, TN 37398

  Located near Tims Ford Lake with deeded lake access, this well-built all brick home offers privacy, space, and plenty of potential on 2.64 wooded acres. With 2,431 sq ft, the home features 3 bedrooms, 2.5 bathrooms, a sunroom, large basement, garage, and attached carport. Mature trees provide a peaceful setting with room to enjoy the outdoors while still being just minutes from Tims Ford State

  Clay Dunivan Simple Real Estate - Keller Williams

  90 Owl Hollow Ln, Winchester, TN 37398
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  /40

  $435,000

  $25K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,425 Sq Ft

  102 Cannonball Ct, Winchester, TN 37398

  Every great lake story begins with finding the perfect place to call home.. and this one is waiting for its next chapter. Nestled inside a gated lake community, this charming 2 master bedroom, 2 bath retreat is where everyday life feels like a getaway. Wake up with a cup of coffee on the porch swing as the morning breeze drifts through the lush landscaping, then end your evenings gathered around

  Angela Miller John Smith Jr Realty and Auction LLC

  102 Cannonball Ct, Winchester, TN 37398
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  /27

  $499,999

  • 3 Beds
  • 2 Baths
  • 1,388 Sq Ft

  512 Cline Ridge Rd, Winchester, TN 37398

  Fresh opportunity on Tims Ford Lake with improved pricing! If you have been looking for privacy, land, and lake life, this one deserves a second look. Set on a wooded lot with space for backyard bonfires, quiet evenings under the stars, and outdoor living, this property also includes private dock access approximately 400 yards from the home. Be on the water in minutes with no long idle zones and

  Jordan Crouch Benchmark Realty, LLC

  512 Cline Ridge Rd, Winchester, TN 37398
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  /55

  $489,900

  • 4 Beds
  • 4 Baths
  • 2,084 Sq Ft

  65 Duncan Ln, Winchester, TN 37398

  Rare opportunity to own a nearly new, high-end duplex built in 2023. The property features two beautifully finished 2-bedroom, 2-bath units, each offering 888 square feet of modern, efficient living space with an attached one-car garage. Both units are thoughtfully designed with open-concept layouts, upscale finishes, modern kitchens, and spacious bedrooms with private baths. One unit is

  Charlie Gonzales Southern Middle Realty

  65 Duncan Ln, Winchester, TN 37398
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  /53

  $309,900

  $10K PRICE DROP

  • 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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  /64

  $475,000

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

  309 2nd Ave NW, Winchester, TN 37398

  SELLER OFFERING OWNER FINANCING AT 5.75% — This income-producing property just over a block from downtown Winchester, provides a rare opportunity for buyers seeking investment property in Tennessee with immediate rental income and future flexibility. Built in 1917, this historic, commercially zoned 5-bedroom, 2-bath residence generates approximately $2,000/month in rental income and includes

  Robert Duncan eXp Realty

  309 2nd Ave NW, Winchester, TN 37398
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  /50

  $239,900

  $10K PRICE DROP

  • 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
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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

  $476,800

  Open House 7/25 $20K 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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  /21

  $375,000

  $45K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,803 Sq Ft

  25 Billy Goat Hill Rd, Winchester, TN 37398

  Custom built 3-bedroom, 2-bath single-family home offering 1,800 square feet of living space on a large corner lot. Freshly painted in 2025, this home features crown molding throughout, including custom detail work. The large living room is perfect for hosting family and friends and is wired for surround sound so you can truly enjoy the big games. The kitchen offers granite countertops and custom

  Ashley Nelson Franklin County Realty

  25 Billy Goat Hill Rd, Winchester, TN 37398
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  /41

  $364,500

  $10K PRICE DROP

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

  205 Houghton Dr, Winchester, TN 37398

  Motivated Seller!! 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

  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
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  /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

  • 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 8 for access to

  Greg Sitz Parks Auction & Realty

  9 Summer Lake Ct, Winchester, TN 37398
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  /45

  $469,900

  New Construction $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,269 Sq Ft

  188 Wiseman Ln, Winchester, TN 37398

  Discover this beautiful home featuring custom-built cabinets, granite countertops, spacious walk-in closets, a welcoming covered front porch, and a back deck perfect for relaxing or entertaining. Sitting on 1.386 acres, the property boasts a huge, flat, and cleared backyard—ideal for kids, pets, and outdoor activities. Located in a peaceful and desirable new neighborhood, this home offers

  Andrew Curl Better Homes & Gardens Real Estate Heritage Group

  188 Wiseman Ln, 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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  /25

  $210,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,348 Sq Ft

  107 Highland Dr, Winchester, TN 37398

  Assumable 5.7% Mortage Rate Rare opportunity in Winchester offering 2 bedrooms, 1 full bath, and a large bonus room that easily functions as a third bedroom. Flexible floor plans with this level of space and versatility near Tim’s Ford Lake are increasingly hard to find at this price point. This home delivers both lifestyle appeal and long-term value potential in a growing Franklin County market.

  Brooke Wooley LPT Realty LLC

  107 Highland Dr, Winchester, TN 37398
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  /36

  $300,000

  • 4 Beds
  • 3 Baths
  • 1,960 Sq Ft

  240 Myers Rd, Winchester, TN 37398

  Welcome to peaceful country living in beautiful Winchester, Tennessee. Priced below appraised value, this is the perfect option to have instant equity in your next home. This charming property at 240 Myers Road offers the perfect blend of privacy and convenience, nestled on a serene setting just minutes from Tims Ford Lake, city parks, and the historic Winchester town square. Enjoy the quiet

  Wade Trammell Keller Williams Realty

  

  240 Myers Rd, Winchester, TN 37398
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  /36

  $325,000

  New Construction

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

  1563 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

  1563 Paynes Church Rd, Winchester, TN 37398
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  /27

  $389,999

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

  131 Charlotte Dr, Winchester, TN 37398

  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 Move In Ready

  Landon Keller Century 21 Volunteer Realty

  131 Charlotte Dr, Winchester, TN 37398
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  /37

  $449,000

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

  109 Oak Park, Winchester, TN 37398

  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 for gathering with family and friends. The updated interior offers

  Penny Bowen Bowen Signature Properties

  109 Oak Park, Winchester, TN 37398
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  /36

  $325,000

  New Construction

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

  1585 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

  1585 Paynes Church Rd, Winchester, TN 37398
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  /15

  $369,500

  • 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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  /55

  $309,000

  New Construction $6K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,472 Sq Ft

  6265 Lynchburg Rd, Winchester, TN 37398

  Come take a look and settle yourself right in. This home offers 1472 sqft of newly constructed living space. With a well thought out floorplan and an open concept layout you will not be disappointed. The kitchen and bathrooms feature custom cabinetry and stainless-steel appliances with brushed nickel finishes. The open concept layout with 2 beds and 2 bath and split bedroom floorplan provide

  Sabrina Watts Swaffords Property Shop

  6265 Lynchburg Rd, Winchester, TN 37398
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  /24

  $475,000

  $25K PRICE DROP

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

  615 Lakeview Way, Winchester, TN 37398

  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 stained glass windows that bathe the entry in soft, colorful light. Inside, the

  Landon Keller Century 21 Volunteer Realty

  615 Lakeview Way, Winchester, TN 37398
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  /37

  $344,900

  New Construction $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft

  267 Brookfield Cir, Winchester, TN 37398

  Beautiful NEW construction just minutes away from Twin Creeks Marina! This beautifully crafted home features a durable Hardiboard exterior and an inviting open floor plan designed for comfortable everyday living and entertaining. Split bedroom concept, luxury vinyl flooring in main living areas, custom shelving in all closets and pantry, walk in tile shower in primary bathroom, stunning lighting

  Jackson Lynch Lynch Rigsby Realty & Auction, LLC

  267 Brookfield Cir, Winchester, TN 37398
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  /31

  $249,000

  New Construction $16K PRICE DROP

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

  62 Modena Place, Decherd, TN 37324

  $3,000 Allowance for appliances! 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.

  Sharon Swafford Swaffords Property Shop

  62 Modena Place, Decherd, TN 37324
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  /52

  $310,000

  $40K PRICE DROP

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

  1200 Little St, Winchester, TN 37398

  Room for everyone! Fully updated from top to bottom and located just minutes from Tims Ford Lake and Boiling Fork Creek. This rare, single-level ranch features no stairs and TWO separate living areas, making it the perfect setup for a large family or a high-yield "heads-in-beds" rental investment. Enjoy total peace of mind with a brand-new metal roof, siding, windows, and a gorgeous designer

  Seth Choate Keller Williams Realty Nashville/Franklin

  1200 Little St, Winchester, TN 37398
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  /27

  $369,900

  $10K PRICE DROP

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

  67 Lake Ln, Winchester, TN 37398

  Welcome to 67 Lake Ln. in Winchester! This beautifully maintained 3-bedroom, 2-bath home sits on nearly an acre and offers the perfect Iblend 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 features hardwood floors throughout the main living area. Step outside to an

  Brandy Scott Winton Auction & Realty Co.

  67 Lake Ln, Winchester, TN 37398
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  /49

  $465,000

  New Construction

  • 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
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  /30

  $349,900

  $40K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft

  5630 Mansford Rd, Winchester, TN 37398

  If you’re dreaming of a charming brick home nestled in a peaceful countryside surrounded by pastureland. This charming brick home on 0.68 acres in a country setting combines the warmth and durability of brick with the peace and space of rural living, making it ideal for those who value both style and tranquility also would make great starter home. Home sales partial furnished. Garage is plumbed

  Sam Hatfield Sam Hatfield Realty, Inc.

  5630 Mansford Rd, Winchester, TN 37398
• 

  

  /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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  /80

  $369,900

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,653 Sq Ft

  401 E Petty Ln, Winchester, TN 37398

  BASEMENT HOME! Step into this beautifully updated 3BR/2.5BA home offering comfort, style, and room to grow. The open kitchen shines with stainless appliances and a modern hood, flowing easily into the den where a welcoming fireplace sets the tone for cozy evenings. A bright Florida room and a partially finished basement with new flooring add versatile living areas. Separate Living room offers

  Daryl Welch Freedom Realty Group

  401 E Petty Ln, Winchester, TN 37398
• 

  

  /7

  $429,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,706 Sq Ft

  0 Mansford Rd Unit RTC3155736, Winchester, TN 37398

  Construction will start once we have an agreement for purchase. Builder offering financing!! This is a brand-new, customizable 3-bedroom, 2-bath home featuring an open floor plan. Buyers have the opportunity to choose finishes and adjust the floor plan to fit their lifestyle. Standard features include luxury vinyl plank flooring throughout, beautiful granite countertops, soft-close cabinetry, a

  Bo Davis Keller Williams Realty - Murfreesboro

  0 Mansford Rd Unit RTC3155736, 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
• 

  

  /54

  $444,900

  New Construction $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,890 Sq Ft

  124 Lookout Dr, Winchester, TN 37398

  Welcome to the Winchester Plan—a beautifully designed 1-level, 4-bedroom home offering comfort, style, and functionality! The open living concept creates a warm and inviting atmosphere, perfect for family gatherings and entertaining guests. Enjoy relaxing evenings on the covered back porch, ideal for outdoor dining or simply taking in the peaceful surroundings. Located in a gated, family-friendly

  Mitchell Bowman simpliHOM - The Results Team

  124 Lookout Dr, Winchester, TN 37398

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