Winchester, KY Homes for Sale under $600,000

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  /23

  $324,900

  $45K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,868 Sq Ft

  225 Plantations Dr, Winchester, KY 40391

  Welcome to 225 Plantations Drive, a beautifully maintained home in the desirable Royal Oaks Subdivision. This charming three-bedroom, two-and-a-half-bath residence is in wonderful condition and move-in ready! This is home comes with a wonderful floorplan that has a primary bedroom with built-in's on the first floor, Kitchen with granite and stainless appliances and deck has been updated with Trex

  John Wilson Bluegrass Properties Group

  225 Plantations Dr, Winchester, KY 40391
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  /2

  $490,000

  $60K PRICE DROP

  • Land
  • 1.53 Acres
  • $320,261 per Acre

  33-41 Winn Ave, Winchester, KY 40391

  Discover a rare opportunity in downtown Winchester with this assemblage of four vacant lots being sold together as a single offering. Zoned L1 and totaling approximately 1.53 acres, this property presents exceptional potential for redevelopment, infill housing, multiunit residential, mixeduse, or commercial concepts in a central location. Situated just steps from local shops, restaurants,

  Bob Sophiea eXp Realty, LLC

  33-41 Winn Ave, Winchester, KY 40391
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  /42

  $350,000

  $10K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 4,798 Sq Ft

  502 W Lexington Ave, Winchester, KY 40391

  Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, high visibility commercial space with Lexington Avenue frontage and two apartments on the upper level! Each apartment has two bedrooms, one bath. One unit has been recently remodeled, the other has potential for value add. The flexible commercial space contains 3 half baths. Laundry hook-ups in all 3 units!

  Jason Townsend Kentucky Residential Real Estate, LLC

  502 W Lexington Ave, Winchester, KY 40391
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  /62

  $329,900

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  335 Newcastle Ln, Winchester, KY 40391

  Welcome to this well-maintained home located in a quiet, established neighborhood with convenient access to everything Winchester has to offer. The first floor features an open and inviting layout, creating a comfortable space for everyday living and entertaining alike. Upstairs, you'll find a traditional three-bedroom floor plan with generously sized bedrooms, including a spacious primary suite.

  Josh Wood Freedom Realty & Property Management

  335 Newcastle Ln, Winchester, KY 40391
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  /45

  $369,000

  $46K PRICE DROP

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

  608 Colby Rd, Winchester, KY 40391

  E Anthony Phillips RE/MAX Creative Realty

  608 Colby Rd, Winchester, KY 40391
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  /55

  $515,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,563 Sq Ft

  935 Stoner-Ephesus Rd, Winchester, KY 40391

  Picture this: over five acres of Kentucky countryside, a handsome ranch-style home, and enough elbow room to finally breathe. This stunning 2,563 square foot retreat delivers the rare combination of refined interior finishes and genuine rural charm, all without sacrificing modern convenience. Inside, discover a generous family room anchored by a striking stone fireplace — the kind of space that

  Timothy Saylor Threshold Real Estate Services

  935 Stoner-Ephesus Rd, Winchester, KY 40391
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  /39

  $415,000

  • 3 Beds
  • 2 Baths
  • 2,304 Sq Ft

  215 Delaplain Rd, Winchester, KY 40391

  215 Delaplain Road is the kind of home where pride of ownership is easy to see. Inside, you'll find 3.25-inch hand-scraped hardwood flooring throughout, travertine tile in both bathrooms, updated vanities, newer light fixtures, and a beautifully tiled walk-in shower with a custom glass door in the primary bath. The kitchen offers added cabinetry/wet bar space, a newer refrigerator, and a gas line

  Alyssa Ryan Marshall Lane Real Estate - Lexington

  215 Delaplain Rd, Winchester, KY 40391
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  /5

  $575,000

  • Land
  • 1.71 Acres
  • $336,257 per Acre

  1025 Colby Rd, Winchester, KY 40391

  This 1.7+/- acre parcel represents an excellent opportunity for almost any commercial application. The property has 397 feet of frontage along busy Colby Road (9,170 AADT, 2015) near its intersection with the Winchester Bypass (23,200 AADT, 2011). Located in the main shopping corridor of Clark County, this property receives tons of exposure and traffic from the adjacent Walmart Super-center,

  Jo Gawthrop Keller Williams Bluegrass Realty

  1025 Colby Rd, Winchester, KY 40391
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  /31

  $479,000

  $26K PRICE DROP

  • 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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  /2

  $600,000

  • Land
  • 6.13 Acres
  • $97,879 per Acre

  722 Colby Rd Unit 2, Winchester, KY 40391

  Discover an exceptional opportunity for retail investment in the thriving Winchester area. Zoned B-4, this versatile property offers a wide array of possibilities for retail development, providing a strategic location for businesses seeking to establish a prominent presence. With its prime zoning and desirable position within the Winchester area, this property presents a compelling prospect for

  Cheryl Johnston CMI Properties

  722 Colby Rd Unit 2, Winchester, KY 40391
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  /42

  $399,000

  $21K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  19 Fontaine Blvd, Winchester, KY 40391

  Charming story and a half home nestled in a well established neighborhood, featuring beautiful hardwood floors and an updated kichen with modern finishes and ample cabinet space. Relax and entertain with ease on the screened back deck overlooking the large fenced backyard and enjoy the added bonus of a charming gazebo, perect for outdoor gathers or peaceful evenings. This well maintaned home

  Kathryn Cheuvront Coldwell Banker McMahan

  19 Fontaine Blvd, Winchester, KY 40391
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  /21

  $326,000

  $1K PRICE INCREASE

  • Land
  • 48.54 Acres
  • $6,716 per Acre

  380 Howard Creek Rd Unit 380, Winchester, KY 40391

  Escape to the peace and privacy of this beautiful 48.54-acre unimproved property in a remote rural setting. Featuring a mix of rolling pasture and wooded acreage with gentle slopes, this versatile tract is ideal for farming, cattle, horses, recreation, hunting, or building your dream country retreat. Whether you're looking for productive agricultural land or a private getaway, this property

  Kathy Burton Coldwell Banker McMahan

  380 Howard Creek Rd Unit 380, 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 Clean Sweeps and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Homes

  145 Codella Dr, Winchester, KY 40391
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  /55

  $324,900

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft

  1291 Muddy Creek Rd, Winchester, KY 40391

  Rare opportunity with TWO lots!! This cozy ranch home, originally built in 1952, but was completely remodeled down to the studs in 2023 (per Seller), offering the charm of an established home with the feel of modern construction. The open concept floor plan features a spacious family room flowing seamlessly into the kitchen, perfect for every day, living and entertaining. The layout provides

  Terri McGraw FC Tucker Bluegrass

  1291 Muddy Creek Rd, Winchester, KY 40391
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  /30

  $312,000

  $11K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,648 Sq Ft

  412 Pueblo Ct, Winchester, KY 40391

  Welcome to this beautifully maintained 5-year-old home nestled on a quiet cul-de-sac in the desirable Ft. Estill area of Winchester. This charming property offers 3 bedrooms and 2.5 baths, a spacious and functional layout with comfortable living areas perfect for both everyday living and entertaining. Enjoy low-maintenance flooring throughout all the main living areas and plenty of natural light

  Lisa Dickens Rector Hayden Realtors

  412 Pueblo Ct, Winchester, KY 40391
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  /30

  $329,900

  $20K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,456 Sq Ft

  410 W Lexington Ave, Winchester, KY 40391

  Whether you're looking for a large residential home, investment opportunity, business potential, or a combination of uses, this property is ready to fit your vision. Featuring 5 bedrooms, 4 baths, soaring 10 foot ceilings, and a welcoming front porch, this unique property blends character, space and versatility. Generous room sizes, timeless charm, and flexible living spaces make it ideal for

  Tracy Ison Bluegrass Home Group

  410 W Lexington Ave, 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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  /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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  /33

  $465,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  287 Logan Lick Rd, Winchester, KY 40391

  This 3 bedroom 2 bath ranch home is tucked away in a beautiful wooded area of Clark County. It is sitting on over 10 acres of land that would be great for livestock or hunting. It is just minutes from historic downtown Winchester. The property is also a short drive to retail shops, restaurants, and other amenities. Come take a look at the beautiful view from the front porch of this home in the

  Dale Hatton Dream Maker Realty, LLC

  287 Logan Lick Rd, Winchester, KY 40391
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  /2

  $550,500

  $31K PRICE INCREASE

  • Land
  • 20.78 Acres
  • $26,492 per Acre

  1395 Two Mile Rd, Winchester, KY 40391

  PLANNED DEVELOPMENT INVESTMENT OPPORTUNITY! Already Zoned Planned Development! There is an approximately 21 acre Residential tract that adjoins the Winchester Country Club. (In addition there is an approximately 24 acre tract suitable for all forms of Residential use. The remaining 103 acres is available for all forms of zoning with frontage on the approved ByPass extension. The two

  Garnett Davis Tom Goebel & Company

  1395 Two Mile Rd, 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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  /10

  $550,000

  $100K PRICE DROP

  • Land
  • 3 Acres
  • $183,333 per Acre

  609 Bullion Blvd Unit 3A, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

  Greg Leveridge Block + Lot Homes

  609 Bullion Blvd Unit 3A, Winchester, KY 40391
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  /49

  $445,500

  • 3 Beds
  • 2.5 Baths
  • 2,961 Sq Ft

  42 Mockingbird Valley Rd, Winchester, KY 40391

  This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons

  Markus Cross McCallie Real Estate

  42 Mockingbird Valley Rd, 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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