Winchester, KY Homes for Sale under $400,000

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  /12

  $189,900

  $40K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,484 Sq Ft

  605 College St, Winchester, KY 40391

  Brick ranch in the College Park neighborhood. Large living area and kitchen with updated appliances and mechanicals (water heater and heat pump). The previous owner water proofed the basement and a new garage door has been installed. Bonus room could be utilized as an additional living room or bedroom.

  Steve Adams Steven D Adams Real Estate Services, LLC

  605 College St, Winchester, KY 40391
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  /60

  $375,000

  $40K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,310 Sq Ft

  382 S Main St, Winchester, KY 40391

  Built in 1893, this beautifully maintained home is filled with the charm and craftsmanship that's hard to find today, along with the modern updates buyers appreciate. Situated on a corner lot just minutes from historic downtown Winchester, you'll love the walkable location with South Main Grocery & Grill, a local favorite known for its country ham sandwiches and home-cooked meals, right across

  Michelle Blackburn RE/MAX Creative, Winchester

  382 S Main St, Winchester, KY 40391
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  /65

  $235,000

  Open Sat 1PM - 3PM

  • 2 Beds
  • 1.5 Baths
  • 1,039 Sq Ft

  47 Hughes Ave, Winchester, KY 40391

  Country living with the convenience of being in the city! This rare find offers over an acre of land inside the Winchester city limits with beautiful views of surrounding farmland. Relax on the spacious covered back deck, entertain family and friends, or enjoy plenty of room for gardening, pets, and play. The home features 2 bedrooms, 1.5 baths, and approximately 1,039 square feet of living space

  Susan Baldwin Threshold Real Estate Services

  47 Hughes Ave, Winchester, KY 40391
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  /49

  $165,000

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,202 Sq Ft

  1494 Amster Grove Rd, Winchester, KY 40391

  Welcome to this charming river front house. Step out your back door and you are immediately at the river. Open floor plan with a wood burning fireplace. Metal cabinets and epoxy floors on the first level are designed to survive in case of a flood. First floor bedroom with enough room for a King sized bed. Upstairs you will find another bedroom and a half bath. Sip your morning coffee on your back

  Libby VanMeter Marshall Lane Real Estate - Lexington

  1494 Amster Grove Rd, Winchester, KY 40391
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  /41

  $339,900

  • 3 Beds
  • 2 Baths
  • 1,858 Sq Ft

  23 Windridge Dr, Winchester, KY 40391

  Welcome home to Windridge!!! This beautifully updated all-brick ranch that perfectly blends charm and modern upgrades in a well established, desirable neighborhood is sure to please. Step inside to a bright open-concept living space featuring luxury vinyl flooring, a stunning wood-burning fireplace, and exposed wood ceiling beams that create a warm, inviting atmosphere in the spacious family

  Holly Goeing The Agency

  23 Windridge Dr, Winchester, KY 40391
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  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 13,939 Sq Ft
  • $312,500 per Acre

  141 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  141 Duclair Dr, Winchester, KY 40391
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  /6

  $299,000

  $151K PRICE DROP

  550 E Broadway St, Winchester, KY 40391

  Prime land located on the outskirts of Winchester ready for possible development. Parcel has frontage on both East Broadway and Washington Street. Land is currently zoned A-1. Utilities available. The future awaits!!!

  Keith Wilson Coldwell Banker McMahan

  550 E Broadway St, Winchester, KY 40391
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  /36

  $125,000

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  25 Oliver St, Winchester, KY 40391

  Welcome to 25 Oliver Street, an affordable 3 bedroom, 1 bathroom ranch home in Winchester offering a practical blend of charm and investment potential. With 900 sq ft of first-floor living space, this home features a comfortable layout with vinyl flooring and a manageable single-level design that works well for homeowners, renters, or buyers looking to build equity. The unfinished basement with

  Jacob Jones Keller Williams Bluegrass Realty

  25 Oliver St, Winchester, KY 40391
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  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 13,939 Sq Ft
  • $312,500 per Acre

  129 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  129 Duclair Dr, Winchester, KY 40391
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  /18

  $148,900

  $1K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,362 Sq Ft

  11 Taylor Ave, Winchester, KY 40391

  Back on Market! Buyers financing fell through. This 3 BR home located in the heart of Winchester and just minutes from the vibrant downtown area, offers the perfect blend of convenience, character, and opportunity. Great opportunity for investors or homeowners. Outside you will love the spacious yard and can relax on the back deck with your morning coffee. Enjoy being within close proximity to

  Alyssa M Boley Coldwell Banker McMahan

  11 Taylor Ave, Winchester, KY 40391
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  /27

  $235,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,297 Sq Ft

  13 Long Ave, Winchester, KY 40391

  Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviting covered front porch, perfect for morning coffee or evening unwinding. Inside, you'll find a spacious living room and dining room featuring beautiful hardwood floors that add warmth and character. The generous yard offers plenty of space for outdoor entertaining, gardening, play or future possibilities.

  Kathryn Cheuvront Coldwell Banker McMahan

  13 Long Ave, Winchester, KY 40391
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  /29

  $279,999

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  103 Southern Ct, Winchester, KY 40391

  Simply the Best! 3 Bedroom, 1 1/2 bath All Brick ranch home located within walking distance to historic downtown Winchester, Country Club, Middle School, great place to live, you will spend most of your time on the Sunporch off the Kitchen, large lot, many updates, floor, bathrooms, new furnace, fresh paint, don't miss looking at this jewel, call today

  Mila Ensor Ensor Real Estate, LLC

  103 Southern Ct, Winchester, KY 40391
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  /30

  $375,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,945 Sq Ft

  309 Gallahadion Ct, Winchester, KY 40391

  Just a 20-second golf cart ride to the Winchester Country Club driving range! Built in 2024 and upgraded throughout, this beautiful 3-bedroom, 2.5-bath home offers modern style, functional living space, and a prime location. The open-concept main level features a spacious living room, kitchen, and dining area designed for both everyday living and entertaining, complete with granite countertops in

  Michelle Blackburn RE/MAX Creative, Winchester

  309 Gallahadion Ct, Winchester, KY 40391
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  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 13,939 Sq Ft
  • $312,500 per Acre

  165 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  165 Duclair Dr, Winchester, KY 40391
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  /24

  $290,000

  $10K PRICE DROP

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

  209 Boone Ave, Winchester, KY 40391

  Space, updates, and charm all come together in this spacious 2,260 square foot 1.5-story home located in the heart of Winchester! Recently updated and full of character, this property offers a flexible layout with room for everyone. The main level offers a welcoming living room, large family room, dining area, kitchen, laundry room, full guest bath, and a spacious primary suite complete with a

  Todd Hyatt Lois Ann Disponett Real Est

  209 Boone Ave, Winchester, KY 40391
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  /21

  $265,000

  • 3 Beds
  • 1 Bath
  • 1,324 Sq Ft

  119 Sunset Heights, Winchester, KY 40391

  Come Home to Sunset!!!! Brick Ranch home, with 2 driveways, 3 bedrooms, 1 bathroom, Open Living Room, Dining Room and Kitchen Area, Spacious Laundry Room, Covered back patio for outdoor living! Beautiful Hardwood floors, updated bathroom and kitchen, exceptional location, building out back for he shed or she shed or storage, move in and enjoy the sunset!

  Whitney Ensor Ensor Real Estate, LLC

  119 Sunset Heights, Winchester, KY 40391
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  /76

  $139,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,360 Sq Ft

  404 Mount Vernon Dr, Winchester, KY 40391

  Ready to Stop Renting? Your Opportunity Is Here Step into the comfort and freedom of homeownership with this spacious, well maintained 2-bedroom, 2-bath modular home — and yes, the lot is included. An attached room addition provides even more flexibility, easily adaptable into a third bedroom, home office, hobby room, or bonus space to suit your lifestyle. --- Interior Highlights • 2 full

  Darrell Tackett Dream Maker Realty, LLC

  404 Mount Vernon Dr, Winchester, KY 40391
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  /2

  $110,000

  • Land
  • 25,700 Sq Ft
  • $186,441 per Acre

  255 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  255 Duclair Dr, Winchester, KY 40391
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  /33

  $277,000

  $12K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,170 Sq Ft

  214 S Burns Ave, Winchester, KY 40391

  Step into the timeless charm of this beautifully maintained historic home featuring 4 bedrooms, 1.5 baths, a formal dining room, living room, laundry room, and charming library with built-in bookshelves and pocket doors. Original heart pine floors, soaring ceilings, a winding staircase, and five decorative fireplaces showcase the home's historic craftsmanship, while updates provide modern

  Lindsay Heeger eXp Realty LLC

  214 S Burns Ave, Winchester, KY 40391
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  /28

  $349,900

  $5K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,325 Sq Ft

  119 Gibson Way, Winchester, KY 40391

  Updated Price, below Apprisal value...Space, Location, and Great Finishes....4 bedrooms, 2.5 bathrooms, walk in sit down and relax...Dining Room/Living Room or Office welcomes you as you enter from the covered front porch. Guests can use the 1/2 bathroom on the main level...Open Kitchen and Family Room with granite counter tops, breakfast bar, and large pantry making cooking easy, 10 ft ceilings

  Whitney Ensor Ensor Real Estate, LLC

  119 Gibson Way, Winchester, KY 40391

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