Winchester Homes for Sale

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  /31

  $505,000

  • 8 Beds
  • 4 Baths
  • 5,058 Sq Ft

  265 S Highland St, Winchester, KY 40391

  Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8

  J Corey Griffo RE/MAX Elite Lexington

  265 S Highland St, Winchester, KY 40391
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  /3

  $146,000

  • 3 Beds
  • 1 Bath
  • 1,020 Sq Ft

  228 Jackson St, Winchester, KY 40391

  Here's your chance to own a nice investment property. This single family home has a 3 bed 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  228 Jackson St, Winchester, KY 40391
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  /15

  $600,000

  • 8 Beds
  • 4 Baths
  • 5,046 Sq Ft

  101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391

  Step into a rare investment opportunity in the heart of downtown Winchester! This beautifully renovated 4-plex offers charm, space, and convenience — all within a fully restored historic building. Each of the four spacious units boasts approximately 1,296 sq ft, blending timeless character with modern updates. The entire property has been thoughtfully renovated in 2021, including a brand-new

  Priya Patel-Rossetti Big Blue Realty

  101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391
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  /14

  $189,999

  • 3 Beds
  • 1 Bath
  • 950 Sq Ft

  41 Hiawatha Trail, Winchester, KY 40391

  Investor Special with Charm & Potential! Don't miss this opportunity to bring new life to this adorable brick home full of character and promise! Featuring beautiful hardwood floors, timeless curb appeal, and a layout ready to shine again, this property is the perfect canvas for your next project. Whether you're an investor, flipper, or buyer looking to build equity, this home offers classic

  Hannah Toole Coldwell Banker McMahan

  41 Hiawatha Trail, Winchester, KY 40391
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  /4

  $10,000

  • Land
  • 0.17 Acre
  • $59,880 per Acre

  117 4th St, Winchester, KY 40391

  Discover the potential of this spacious 0.17-acre residential property nestled in a neighborhood community on clear and level vacant lot located in a Cul-de-sac of Lincoln Park Subdivision. This could be an investment opportunity as well, for ideal savvy investors looking to diversify your portfolio this property would be perfect for building a custom home, holding for future value, or develop

  Anita McDermott Keller Williams Bluegrass Realty

  117 4th St, Winchester, KY 40391
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  /22

  $250,000

  • Land
  • 14.51 Acres
  • $17,228 per Acre

  3056 Irvine Rd, Winchester, KY 40391

  Discover the perfect blend of beauty, privacy, and opportunity with this stunning 14.511-acre tract on Irvine Road. Featuring gently rolling hills, this property offers multiple ideal building sites to bring your dream home to life, whether you're envisioning a modern farmhouse, barndominium, or private country retreat. A barn is already in place, adding immediate functionality for storage,

  Christa Joynt Keller Williams Commonwealth

  3056 Irvine Rd, Winchester, KY 40391
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  /60

  $279,950

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft

  115 Watercrest Cir, Winchester, KY 40391

  Stunning Home in One of the Area's Most Coveted Neighborhoods!Experience spacious living with 3 generous bedrooms and 2 full baths on the main level, designed for comfort and everyday convenience. The walkout basement offers even more space with a large bedroom and an additional full bath, ideal for guests, extended family, or a private retreat. What truly sets this home apart? The sellers are

  Darrell Tackett Dream Maker Realty, LLC

  115 Watercrest Cir, Winchester, KY 40391
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  /13

  $400,000

  • Land
  • 2.19 Acres
  • $182,648 per Acre

  145 Codella Dr, Winchester, KY 40391

  Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Real Estate

  145 Codella Dr, Winchester, KY 40391
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  /77

  $924,900

  • 5 Beds
  • 4.5 Baths
  • 6,314 Sq Ft

  7210 Ecton Rd, Winchester, KY 40391

  Welcome to 7210 Ecton Road a stunning 5 bedroom, 4.5 bathroom home situated on 7+/- acres (awaiting final survey) of gently rolling Kentucky countryside. This property offers the perfect balance of modern comfort, privacy, and wide-open space, just minutes from downtown Winchester. Step inside to discover a spacious and well-designed floor plan featuring: 5 generously sized bedrooms including a

  Megan McCoy Keller Williams Legacy Group

  7210 Ecton Rd, Winchester, KY 40391
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  /6

  $388,000

  • 5 Beds
  • 3 Baths
  • 2,762 Sq Ft

  101 E Lexington Ave, Winchester, KY 40391

  Here's your chance to own a nice investment property. This triplex has a 2 bed 1 bath unit, 2 bed 1 bath unit, and a 1 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  101 E Lexington Ave, Winchester, KY 40391
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  /3

  $251,000

  • 6 Beds
  • 3 Baths
  • 2,302 Sq Ft

  133 S Highland St, Winchester, KY 40391

  16 Central Ave, Winchester, KY 40391Prime multi-family investment in a great Winchester location! This 2-story property features two spacious rental units, both offering strong income potential. The first unit includes 3 bedrooms and 2 bathrooms, while the second unit offers 3 bedrooms and 1 bathroom—ideal for accommodating a range of tenant needs. With an established rental history and close

  David Espinosa Bluegrass Realty Pros, Inc

  133 S Highland St, Winchester, KY 40391
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  /12

  $185,900

  • 3 Beds
  • 2 Baths
  • 1,116 Sq Ft

  41 7th St, Winchester, KY 40391

  Welcome to 41 7th Street. This brick ranch offers 3 bedrooms, 2 full baths, and hardwood floors throughout the living room, hallway, and bedrooms, ready to be refreshed with a re-sand and polish. The layout provides a foundation for a buyer looking to add personal updates and make it their own. Located at the end of the street, the home offers added privacy along with peaceful farm views behind

  Austina Bruton Re/Max Elite Realty - Hamburg

  41 7th St, Winchester, KY 40391
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  /24

  $209,900

  • 3 Beds
  • 2 Baths
  • 915 Sq Ft

  225 Buffalo Trace, Winchester, KY 40391

  This move in ready ranch home offering 3 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

  Tyler I Back The Brokerage

  225 Buffalo Trace, Winchester, KY 40391
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  /12

  $199,900

  • 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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  /9

  $102,000

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft

  39 S Highland St, Winchester, KY 40391

  Here's your chance to own a nice investment property. This Single Family home has 2 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  39 S Highland St, Winchester, KY 40391
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  /12

  $144,000

  • 3 Beds
  • 1 Bath
  • 805 Sq Ft

  150 Cook Ave, Winchester, KY 40391

  Here's your chance to own a nice investment property. This has a single family has 3 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  150 Cook Ave, Winchester, KY 40391
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  /6

  $299,000

  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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  /12

  $194,000

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  175 Magnolia St, Winchester, KY 40391

  Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is month to

  A. Rebecca Woods Woods Realty Group

  175 Magnolia St, Winchester, KY 40391
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  /52

  $199,000

  • 3 Beds
  • 1.5 Baths
  • 1,636 Sq Ft

  334 S Burns Ave, Winchester, KY 40391

  Take a look at the nice price adjustment on this one!!! Great opportunity to own this well loved home in a very convenient location in growing community of Winchester. Lots of character and charm upon entry into the entry foyer with nice staircase, opening to large living room with a lovely mantel. Spacious dining room with built in corner cabinet flows into kitchen with plenty of cabinetry and

  Jeanne Beaven Rector Hayden Realtors

  334 S Burns Ave, Winchester, KY 40391
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  /97

  $335,000

  • 3 Beds
  • 2.5 Baths
  • 1,794 Sq Ft

  322 S Burns Ave, Winchester, KY 40391

  This beautiful 1.5-story home offers all the charm of downtown in a small town, with a library, park, and restaurants nearby. Plus, just minutes to Lexington when the city is calling your name. This home has been remodeled for modern living, featuring an open floor plan. There is plenty of room for entertaining with a beautiful, well-equipped kitchen and a large island open to both the dining

  Nancy Hibbitts CENTURY 21 Advantage Realty

  322 S Burns Ave, Winchester, KY 40391
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  /24

  $300,000

  • 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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  /67

  $325,000

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft

  3622 Stamper Dr, Winchester, KY 40391

  This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. With recently installed vinyl siding, gutters and gutter guard properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming

  Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
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  /13

  $130,000

  • 2 Beds
  • 1 Bath
  • 1,254 Sq Ft

  208 4th St, Winchester, KY 40391

  Discover the potential of this spacious 0.27-acre residential home nestled in a neighborhood community on clear and level land located in a Cul-de-sac of Lincoln Park Subdivision. This Property features 2-bedrooms, 1-Bathroom, a large family room with a fireplace. There is also a large versatile barn on the property as well. This could be an investment opportunity as well, for ideal savvy

  Anita McDermott Keller Williams Bluegrass Realty

  208 4th St, Winchester, KY 40391
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  /28

  $799,900

  • Land
  • 13.19 Acres
  • $60,644 per Acre

  1600 Ironworks Rd, Winchester, KY 40391

  This property has it all! Easy access to Veterans Memorial Bypass, I-64, and downtown Winchester, plus entrances on Ironworks and clear visibility from the Bypass. This does have sewer and water located on the property. Full of potential possibilities zoned Planned Development and more acreage is available if needed. The property access is a driveway off Ironworks Road across from Center Drive

  Josh Wood Freedom Realty & Property Management

  1600 Ironworks Rd, Winchester, KY 40391

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