Winchester, KY Homes for Sale under $600,000

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  /65

  $359,900

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

  15 Moundale Ave, Winchester, KY 40391

  Welcome to this beautifully maintained all-brick home nestled in one of Winchester's most established and desirable neighborhoods. Offering over 2,200 square feet of finished living space, this 3-bedroom, 2-bath home combines timeless character with an impressive list of thoughtful updates. The main level features a spacious family room with ventless gas logs, a beautifully updated kitchen with

  Josh Wood Freedom Realty & Property Management

  15 Moundale Ave, Winchester, KY 40391
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  /62

  $309,900

  $20K PRICE DROP

  • 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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  /12

  $495,000

  $34K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,054 Sq Ft

  443 Oxford Dr Unit 443,445,447,449, Winchester, KY 40391

  Don't miss this rare quadruplex opportunity in Winchester. Featuring four units (443, 445,447 and 449 Oxford Drive), this property is perfect for investors seeking multiple income streams in one location. Each unit offers a similar layout with approximately 1,054 ft, 2 bedrooms, and 1.5 baths. The photos shown are from one updated unit, and all units have comparable layouts—making this an ideal

  Tracey Goebel Tom Goebel & Company

  443 Oxford Dr Unit 443,445,447,449, 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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  /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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  /7

  $365,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft

  204 Jett Dr, Winchester, KY 40391

  New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

  Mila Ensor Ensor Real Estate, LLC

  204 Jett Dr, Winchester, KY 40391
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  /31

  $455,000

  $50K 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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  /15

  $450,000

  • Land
  • 9,583 Sq Ft
  • $2,045,455 per Acre

  1320 Fulton Rd, Winchester, KY 40391

  Prime commercial opportunity in an ideally located area of Winchester! This versatile commercial building offers an excellent location for an established business, growing company, or investor seeking a property with strong potential. Conveniently situated with easy access to major roadways and surrounding communities, the property provides excellent visibility and accessibility for customers and

  Holly Spradlin KY Realty Co

  1320 Fulton Rd, 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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  /52

  $536,000

  $3K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,732 Sq Ft

  267 Runnymeade Dr, Winchester, KY 40391

  Welcome to this beautifully designed 3-bedroom, 2.5-bath ranch in the highly sought-after Earlymeade subdivision, where comfort, style, and exceptional efficiency come together. This spacious one-story home offers an open, inviting floor plan highlighted by a stunning floor-to-ceiling stone fireplace that anchors the expansive great room. The well-appointed kitchen features granite countertops,

  Jason Caudill RE/MAX Creative Realty

  267 Runnymeade Dr, Winchester, KY 40391
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  /55

  $395,000

  Open Sun 1PM - 4PM $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 3,306 Sq Ft

  351 Boone Ave, Winchester, KY 40391

  Classic Williamsburg inspired home with charming dormers, timeless character, and an exceptional location that's a short walk to historic downtown Winchester. This spacious 4-bedroom , 2 bath home offers a flexible floor plan with 2 main-level bedrooms and a full bath, plus two additional bedrooms and a full bath upstairs. Enjoy elegant formal living and dining rooms, a large home office, and a

  Jim Woodrum RE/MAX Creative, Winchester

  351 Boone Ave, 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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  /20

  $345,900

  New Construction

  • 3 Beds
  • 4.5 Baths
  • 1,559 Sq Ft

  Julia Plan at Boone's Crossing, Winchester, KY 40391

  Discover the Julia floor plan, a thoughtfully designed new construction home that blends elegant open-concept living with private, comfortable bedroom spaces. Built by one of the most trusted home builders in Central Kentucky, the Julia is a standout choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want modern style, everyday functionality,

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 41774552, Winchester, KY 40391
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  /61

  $419,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,204 Sq Ft

  322 Calmes Blvd, Winchester, KY 40391

  Welcome to this superbly maintained home located in one of the area's most desirable neighborhoods. Offering 11 spacious rooms, this property delivers exceptional comfort, versatility, and charm. A beautiful front wrap around covered porch creates an inviting first impression, perfect for relaxing or greeting guests. The rear of the home features a covered back porch and an adjoining open deck,

  Darrell Tackett Dream Maker Realty, LLC

  322 Calmes Blvd, Winchester, KY 40391
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  /31

  $300,000

  • 4 Beds
  • 2 Baths
  • 2,479 Sq Ft

  224 W Hickman St, Winchester, KY 40391

  Classic character and generous living space come together at 224 W Hickman Street in Winchester. This single-family residence offers 4 bedrooms, 2 full bathrooms, and approximately 2,479 square feet, providing a flexible layout with room for a variety of everyday living needs. The home's substantial interior footprint creates opportunities for comfortable gathering spaces, private bedrooms, a

  Bob Sophiea eXp Realty, LLC

  224 W Hickman St, Winchester, KY 40391
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  /41

  $329,900

  $10K PRICE DROP

  • 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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  /46

  $475,000

  • 3 Beds
  • 2 Baths
  • 2,174 Sq Ft

  625 Pine Ridge Rd, Winchester, KY 40391

  Beautiful all brick ranch home on 4.1 acres that has 3 bedrooms, 2 bathrooms, open concept floor plan, large stone fireplace with wood burning stove & blower. Kitchen has butcher block countertops, garbage disposal, pot filler, range hood, ample cabinets with large pantry cabinet & island. Large primary suite that includes a walk-in tiled shower, with 2 shower heads, has a place for soaking tub

  Tonya Morrow KY Local

  625 Pine Ridge Rd, Winchester, KY 40391
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  /33

  $435,000

  $30K PRICE DROP

  • 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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  /33

  $359,000

  $26K 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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  /24

  $365,900

  New Construction $100K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  206 Jett Dr, Winchester, KY 40391

  New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

  Mila Ensor Ensor Real Estate, LLC

  206 Jett Dr, Winchester, KY 40391
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  /72

  $544,900

  $5K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,741 Sq Ft

  130 Winterberry Cir, Winchester, KY 40391

  Welcome to this beautifully maintained modern home located in the highly sought-after Royal Oaks Estates, perfectly positioned on the edge of Winchester with quick access to shopping, dining, and more. From the moment you step inside, you'll be captivated by the soaring vaulted ceilings in the central great room--an impressive space filled with natural light and designed for both comfort and

  Josh Wood Freedom Realty & Property Management

  130 Winterberry Cir, 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

  $344,900

  $10K 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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