Clark County KY Homes under $300,000

• 

  

  

  /22

  $255,000

  • 4 Beds
  • 2 Baths
  • 2,332 Sq Ft

  35 Cherokee Ct, Winchester, KY 40391

  Step into this 4-bedroom, 2 full bath split-foyer home, perfectly designed for comfortable everyday living. The upper level features three generously sized bedrooms, a full bath, a bright living room, kitchen, and dining area—ideal for gathering with family and friends. Just off the kitchen, enjoy easy access to the covered deck overlooking a spacious backyard. The lower level offers even more

  

  Brenda Rue

  Keller Williams Bluegrass Realty

  (859) 470-8131

  35 Cherokee Ct, Winchester, KY 40391
• 

  

  

  /59

  $289,000

  • 3 Beds
  • 1 Bath
  • 1,273 Sq Ft

  119 Tower Ln, Winchester, KY 40391

  A rare and refined retreat set on five unrestricted acres in Winchester. Privately positioned and surrounded by natural beauty, this renovated berm-style residence offers the perfect balance of seclusion and sophistication. Inside, you'll find thoughtfully curated updates including fresh designer paint, updated flooring, and a bright, inviting interior that feels both modern and timeless. The

  Shawna Wever Wever Realty LLC

  119 Tower Ln, Winchester, KY 40391
• 

  

  

  /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
• 

  

  

  /32

  $265,000

  • 4 Beds
  • 2 Baths
  • 1,739 Sq Ft

  504 Harvard Dr, Winchester, KY 40391

  A spacious Ranch style home with many recent updates. With 4 bedrooms and 2 bath you'll find plenty of space for the everyone. With new laminate flooring, several new doors, and new paint throughout; this home is move in ready! Other updates include a new shower in the master bath, new microwave, new tile in the Utility room, new island top, new shelving in the walk in closet, and new gutters.

  Justin Lee JL Realty Group, LLC

  504 Harvard Dr, Winchester, KY 40391
• 

  

  

  /32

  $249,900

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

  528 Estes Dr, Winchester, KY 40391

  Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
• 

  

  /31

  $204,900

  • 3 Beds
  • 1 Bath
  • 1,290 Sq Ft

  60 Hiawatha Trail, Winchester, KY 40391

  Updated, affordable, and ready for you! This 3-bedroom, 1-bath home offers approximately 1,300 square feet of comfortable living space with tasteful updates that make it easy to move right in. The layout provides a welcoming feel with bright living areas and an updated kitchen and bath. Downstairs you have a possible 4th bedroom or office space. Conveniently located in Winchester close to

  Christina Bucher Keller Williams Legacy Group

  60 Hiawatha Trail, Winchester, KY 40391
• 

  

  /13

  $246,400

  • 5 Beds
  • 3 Baths
  • 3,007 Sq Ft

  221 S Highland St, Winchester, KY 40391

  INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered

  Joshua Lynch The Brokerage

  221 S Highland St, Winchester, KY 40391
• 

  

  /36

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  415 L East Junction Rd, Winchester, KY 40391

  Tucked away on just under 3 peaceful acres in Winchester, this charming 3-bedroom, 2-bath manufactured home on a permanent foundation offers the perfect blend of comfort and country living. Enjoy the privacy and space you've been looking for, with a beautiful creek running along the back of the property—creating a serene backdrop for relaxing evenings or outdoor entertaining. Inside, you'll find

  Rachel Rainey Kentucky Land and Home

  415 L East Junction Rd, Winchester, KY 40391
• 

  

  /30

  $200,000

  • 3 Beds
  • 2 Baths
  • 1,289 Sq Ft

  128 Bay Hill Dr, Winchester, KY 40391

  Opportunity knocks in Royal Oaks Village—be part of Winchester's next chapter. Located within the expanding Deerlawn development, this single-story ranch townhome offers incredible upside in an area poised for growth. With future plans bringing hundreds of new homes, townhomes, and duplexes nearby, this is your chance to get in early and build equity. Inside, you'll find a spacious and functional

  Melia Hord Keller Williams Legacy Group

  128 Bay Hill Dr, Winchester, KY 40391
• 

  

  /24

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,304 Sq Ft

  201 Prescott Ln, Winchester, KY 40391

  This Is The One You Have Been Waiting For!!! Perfect Location, Flat Fully Fenced Backyard And A Large Rear Covered Patio. This 1 1/2 Story 3 Bedroom 2 Bath Home Has Vaulted Ceilings; Lots Of Cabinets; Stainless ' Steel Appliances; Good Size Primary Bedroom With En Suite; Walk In Closet; 2 More Generous Sized Bedrooms And So Much More!

  Patrick Arvin Keller Williams Commonwealth

  201 Prescott Ln, Winchester, KY 40391
• 

  

  /52

  $275,000

  • 4 Beds
  • 2 Baths
  • 2,417 Sq Ft

  104 Jackson Ferry Rd, Winchester, KY 40391

  Located in Winchester, this 4-bedroom, 2-bath home offers approximately 2,417 square feet of living space with room to spread out both indoors and out. The home features a spacious living room with a fireplace, providing a comfortable central gathering area. Multiple bedrooms offer flexibility for guests, home office space, or changing household needs. Recent updates include a renovated kitchen

  Bob Sophiea eXp Realty, LLC

  104 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /29

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  11 Shelley Dr, Winchester, KY 40391

  SELLER is motivated to offers! Welcoming you to this lovely updated throughout 3 bedroom, 2 full bath ranch! As you step into the home with its cozy feeling, and spacious space in every room, including a full unfinished basement wonderful for storage or to finish that into living square footage, great size back yard with large back patio perfect for the family gatherings, also a partial fenced in

  Nichole Bingham CENTURY 21 Advantage Realty

  11 Shelley Dr, Winchester, KY 40391
• 

  

  /28

  $235,000

  • 4 Beds
  • 2 Baths
  • 1,431 Sq Ft

  13 Arlington Rd, Winchester, KY 40391

  One Level Living!!!! This home boasts all the curb appeal with new vinyl siding, new roof and new leaf filter gutter system on home all in 2025!! A vinyl style privacy fenced in back yard, mature trees and beautiful landscaping! 4 bedrooms, 2 full bathrooms, Kitchen with all appliances (range, dishwasher, refrigerator, microwave) with updated flooring! Hardwood floors are showcased in the main

  Whitney Ensor Ensor Real Estate, LLC

  13 Arlington Rd, Winchester, KY 40391
• 

  

  /24

  $225,000

  • Land
  • 24 Acres
  • $9,375 per Acre

  3934 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Wonderful 24 acre retreat with gentle sloping land, and a creek bed running thru part of the front portion of the lots (6.1 acre parcel & 18.4 acre parcel at the rear). Build your dream home or just use as recreational or farm land until you do. 1 1/2 miles to the first exit on the Mountain Parkway exit #10. 12 miles to I-64 at Winchester. See attached pictures & plat/overhead pictures.

  Travis Emnett Top Ten Realty

  3934 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  

  /43

  $269,000

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

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Private 12-Acre Property in Winchester, KY - Convenient to Lexington & Red River Gorge This 3-bedroom, 2-bath single-family home with an office/flex room is situated on 12 acres in Winchester, KY, offering a combination of open and primarily wooded land. The property is located less than 40 minutes from Lexington and approximately 30 minutes from Red River Gorge. The home offers 1,960 square feet

  Felicia Mayes The Real Estate Co.

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  

  /34

  $255,000

  • Land
  • 6.08 Acres
  • $41,941 per Acre

  190 Privacy Ln, Winchester, KY 40391

  6.08 acres settled in Clark County with access from both Privacy Ln and Little Stoner Rd. This property boasts a 30x56 with 10 foot wall Kentucky Steel Truss building with concrete floors, gas and wood burning heat, full bath, and a car lift. Additionally, there is a barn with a 3 bay shed attached.

  Jason Joseph Keller Williams Commonwealth

  190 Privacy Ln, Winchester, KY 40391
• 

  

  /12

  $299,900

  • 4 Beds
  • 4 Baths
  • 2,072 Sq Ft

  1128 Dale Dr, Winchester, KY 40391

  Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

  Brian Hatfield Coldwell Banker McMahan

  1128 Dale Dr, Winchester, KY 40391
• 

  

  /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
• 

  

  /12

  $297,000

  • 4 Beds
  • 2.5 Baths
  • 1,693 Sq Ft

  327 Newcastle Ln, Winchester, KY 40391

  Welcome home to this cozy cute FOUR bedroom house with 2 full bath/ 1 half bath! Rare to find- Primary bedroom and full bath on first floor. Large living area with plenty of sunlight through insulated windows and skylights. This open floorpan also showcases a nice open staircase that overlooks the main floor. Upstairs are 3 additional bedrooms and a full bathroom. Fenced yard and covered patio to

  Huong Dunn Bluegrass Property Exchange

  327 Newcastle Ln, Winchester, KY 40391
• 

  

  /7

  $300,000

  • Land
  • 5.01 Acres
  • $59,880 per Acre

  3811 Combs Ferry Rd, Ford, KY 40391

  Discover the perfect blend of privacy and potential on this beautiful 5-acre property located on highly desirable Combs Ferry Road in Winchester. With plenty of open, level ground, this property offers an ideal setting to build the custom home you've always envisioned while enjoying the peace and space of country living. Already in place is a 1,260-square-foot RV barn equipped with electric and

  Karen Bishop Saltzman National Real Estate

  3811 Combs Ferry Rd, Ford, KY 40391
• 

  

  /32

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,656 Sq Ft

  17 Euclid Ave, Winchester, KY 40391

  Welcome home to 17 Euclid Ave in beautiful College Park area of Winchester. This three bedroom two full bath home may be the one you are looking for. Beautiful Hardwood floors throughout most of the home. Two additional bedrooms are upstairs with a full bath. Fenced in back yard and a large deck for you summertime entertaining. Don't wait, let's take a look.

  Donna Thwaites Thwaites Realtors LLC

  17 Euclid Ave, Winchester, KY 40391
• 

  

  /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
• 

  

  /25

  $254,900

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft

  1407 Ironworks Rd, Winchester, KY 40391

  Welcome to this beautifully remodeled 3 bedroom, 2 full bathroom home situated on a desirable corner lot. With 1,530 sq ft of living space, this home offers great combination of modern updates and comfortable living. Features Include 3 spacious bedrooms, 2 full bathrooms, Private master suite with ensuite bath, Fully remodeled interior, corner lot, Stainless appliances, full tiled showers and the

  Michael Hilario The Agency

  1407 Ironworks Rd, Winchester, KY 40391
• 

  

  /19

  $265,000

  • 4 Beds
  • 3 Baths
  • 2,445 Sq Ft

  130 E Broadway St, Winchester, KY 40391

  Turnkey downtown triplex with tenants already in place. An excellent addition to any investor's portfolio. Two units have been recently updated, while the third features a long-term tenant with future value-add potential. Property includes two 1BD/1BA units and one 2BD/1BA unit. Tenants pay all utilities directly except water, which is on a RUB system, keeping operating costs low. Strong income

  Sarah May Mayca Property Solutions

  130 E Broadway St, Winchester, KY 40391
• 

  

  /12

  $296,000

  • 5 Beds
  • 2 Baths
  • 2,214 Sq Ft

  55 Hillcrest Dr, Winchester, KY 40391

  All-brick ranch with a full walk-out basement! This charming home offers excellent potential for the right buyer. The main level features three bedrooms, a full bath, a comfortable living room, and an eat-in kitchen. The walk-out basement expands the living space with two additional bedrooms, full bath, family room with a kitchenette area, utility room, and ample storage with built-in shelving.

  Nina Vanetten RE/MAX Elite Lexington

  55 Hillcrest Dr, Winchester, KY 40391
• 

  

  /62

  $259,500

  • 3 Beds
  • 2 Baths
  • 1,247 Sq Ft

  3614 Stamper Dr, Winchester, KY 40391

  Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

  Darrell Tackett Dream Maker Realty, LLC

  3614 Stamper Dr, Winchester, KY 40391
• 

  

  /19

  $239,999

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft

  357 Silverton Way, Winchester, KY 40391

  This updated home offers easy access to I-64 and downtown Winchester. See ceiling fans in every room, upstairs bonus room, modern lighting in the kitchen and bath, and new appliances, countertops, and backsplash. Enjoy a peaceful, quiet neighborhood and a relaxing rural view from the backyard. A clean, comfortable, move-in-ready home with thoughtful upgrades throughout.

  Frank Mulder Tru Life Real Estate

  357 Silverton Way, Winchester, KY 40391
• 

  

  /33

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,790 Sq Ft

  211 Lindsey Ct, Winchester, KY 40391

  Nicely updated split-level home with a large, fenced backyard, located on a quiet cul-de-sac. This energy-efficient home boasts a brand-new HVAC system, a recently replaced roof, fresh paint and stylish new LVP flooring throughout the house. The large kitchen has updated countertops and cabinets, as well as brand-new stainless steel appliances with three-year warranties. Both bathrooms have been

  Lesley Ward Biederman Real Estate

  211 Lindsey Ct, Winchester, KY 40391
• 

  

  /12

  $259,900

  • 4 Beds
  • 1 Bath
  • 1,610 Sq Ft

  120 Windsor Dr, Winchester, KY 40391

  Welcome home to this cozy brick charmer in the desirable Belair Subdivision of Winchester, KY! This inviting 4 bedroom, 1 bath home offers comfortable living with a warm electric fireplace perfect for relaxing evenings. The spacious layout provides flexibility for family, guests, or a home office. Step outside to a fully fenced backyard ideal for pets, play, or enjoying quiet mornings with your

  Team Farthing - Mitch Farthing Southern Legacy Realty

  120 Windsor Dr, Winchester, KY 40391
• 

  

  /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
• 

  

  /23

  $270,000

  • 4 Beds
  • 2 Baths
  • 1,984 Sq Ft

  108 Ashley Dr, Winchester, KY 40391

  Be among the first to discover this exceptional property! This is a brand new listing, presenting a unique opportunity to own a home in a highly sought-after location. Imagine living in a neighborhood where everything you need is just a stone's throw away. This fabulous property boasts not only a full basement, offering endless possibilities for recreation, storage, or a home office, but also an

  A. Rebecca Woods Woods Realty Group

  108 Ashley Dr, Winchester, KY 40391
• 

  

  /25

  $295,000

  • Land
  • 10 Acres
  • $29,500 per Acre

  398 Pine Ridge Rd, Winchester, KY 40391

  Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment you walk in. Enjoy the outdoors from the

  Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /14

  $205,000

  • 3 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  10 Upper St, Winchester, KY 40391

  Modern Ranch residence full un-finished basement, large lot.

  E. Clark Toleman Real Estate Appraisal Services

  10 Upper St, Winchester, KY 40391
• 

  

  /30

  $229,900

  • 4 Beds
  • 2 Baths
  • 2,683 Sq Ft

  217 S Highland St, Winchester, KY 40391

  This Spacious investment property is ready for its new owner. The home features fresh updates throughout, large living spaces and endless possibilities. Schedule your showing while you can!

  Michael Hilario The Agency

  217 S Highland St, Winchester, KY 40391
• 

  

  /21

  $244,900

  • 3 Beds
  • 1.5 Baths
  • 1,494 Sq Ft

  720 Estes Dr, Winchester, KY 40391

  This charming brick ranch is truly move-in ready. Offering 3 bedrooms, 1.5 baths, a welcoming living room, a cozy den, and kitchen with appliances, this home blends comfort and convenience with ease. Enjoy the natural light and peaceful views from the screened-in sunporch, perfect for relaxing. Updates include new kitchen flooring, refinished hardwood floors, and updated trim that gives the home

  Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  720 Estes Dr, Winchester, KY 40391
• 

  

  /33

  $210,000

  • 4 Beds
  • 1 Bath
  • 1,743 Sq Ft

  218 E Washington St, Winchester, KY 40391

  Motivated seller! Bring your offers. This home is a charming 4 bedroom 1 bath. It boasts a large bonus room which could be an office or 5th bedroom. This home offers a nice sized laundry room with space to add a second bathroom. This home has a nicely shaded fully fenced in back yard with a gate for easy accessibility . There is also a detached storage garage and a long driveway. Within walking

  Fernando Andrade Rector Hayden Realtors

  218 E Washington St, Winchester, KY 40391
• 

  

  /34

  $275,700

  • 3 Beds
  • 2 Baths
  • 1,682 Sq Ft

  404 Wellington Way, Winchester, KY 40391

  This house is located minutes from the Winchester Bypass and within walking distance of the new Clark County Pre-school. The house features 3 bedrooms and 2 full baths. The kitchen is supplied with all the appliances. And the house also has a washer and dryer. The large great room is perfect for watching the favorite sports teams and movies with family and friends. The sellers added fiber optics

  Craig Bridgewater Bridgewater Real Estate

  404 Wellington Way, Winchester, KY 40391
• 

  

  /4

  $225,000

  • Land
  • 8.09 Acres
  • $27,812 per Acre

  2110 Athens Boonesboro Rd, Ford, KY 40391

  Prime building lot - 8.092 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2110 approved for its own entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first choice on

  Megan McCoy Keller Williams Legacy Group

  2110 Athens Boonesboro Rd, Ford, KY 40391
• 

  

  /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
• 

  

  /17

  $285,000

  • Land
  • 14.51 Acres
  • $19,642 per Acre

  3056 Irvine Rd, Winchester, KY 40391

  Own a genuine piece of Kentucky splendor! Beautiful 14.5 acres of gently rolling land is ideal for building your custom home! The property offers creek access and a barn with electric and water. Don't miss this opportunity to own a farm only 20 miles to Hamburg and 5 miles to Winchester Bypass. No city sewage. Deed restrictions apply. Additional parcel with 11.36 acres is also available. Perfect

  Lura Justice Rector Hayden Realtors

  3056 Irvine Rd, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 2