Winchester, KY 1-Story Homes for Sale

• 

  

  

  /32

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  4305 Old Boonesboro Rd, Winchester, KY 40391

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 549-3072

  4305 Old Boonesboro Rd, Winchester, KY 40391
• Explore Winchester

• 

  

  

  /18

  $556,000

  • 5 Beds
  • 3 Baths
  • 3,102 Sq Ft

  110 White Conkwright Rd, Winchester, KY 40391

  Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

  

  Philip 'PJ' Elder

  Omega Real Estate Brokerage LLC

  (859) 695-3879

  110 White Conkwright Rd, Winchester, KY 40391
• 

  

  

  /71

  $799,000

  • 4 Beds
  • 2.5 Baths
  • 7,058 Sq Ft

  186 Chardonnay Ct, Winchester, KY 40391

  Fontaine Estates, a great place to call home. This spacious 4 bedroom 3 bath property offers an abundance of storage,, including charming window seats. Enjoy the convenience of an oversized driveway and garage, along with a beautifully designed outdoor setting, feauring a fire pit and a dedicated entertainment space. The thoughtfully planned, custom designed landscaping enhances the home's curb

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 470-2071

  186 Chardonnay Ct, Winchester, KY 40391
• 

  

  

  /22

  $139,000

  • 2 Beds
  • 1 Bath
  • 807 Sq Ft

  3208 Ford Hampton Rd, Winchester, KY 40391

  Escape to a lifestyle defined by the peace and natural beauty of this delightful two bedroom property just steps away from the majestic Kentucky River, this home isn't just a place to iive, it is a dedicated sanctuary whether you are seeking a cozy year round residence or a recreational retreat. One of the standout features is the exceptioal connection to the outdoors with generous porches on

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 765-6889

  3208 Ford Hampton Rd, Winchester, KY 40391
• 

  

  

  /46

  $347,900 New Construction

  • 3 - 6 Beds
  • 2 - 4 Baths
  • 1,580 Sq Ft

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

  The Martha floor plan is your canvas for creating a home that perfectly fits your lifestyle, offering unmatched flexibility, thoughtful design, and timeless appeal. Built by one of the leading home builders in Central Kentucky, the Martha is an excellent choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space that adapts to how they

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824258, 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
• 

  

  /52

  $369,900 New Construction

  • 3 - 6 Beds
  • 2 Baths
  • 1,770 Sq Ft

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

  Experience the true essence of homecoming with the Barbara floor plan, a beautifully designed new construction home available through one of the most trusted home builders in Central Kentucky. Thoughtfully crafted for modern living, this plan blends timeless exterior charm with a warm, open interior designed for comfort, flexibility, and everyday functionality.Step onto the inviting covered front

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824253, Winchester, KY 40391
• 

  

  /41

  $343,900 New Construction

  • 3 - 5 Beds
  • 2 - 4 Baths
  • 1,424 Sq Ft

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

  Experience the Lucy floor plan, a versatile and thoughtfully designed new construction home that gives every member of the family the space they need to live, work, and thrive. Built by one of the most trusted home builders in Central Kentucky, the Lucy is a top choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want flexibility, comfort, and

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824256, Winchester, KY 40391
• 

  

  /41

  $169,900

  • 1 Bed
  • 2 Baths
  • 1,056 Sq Ft

  101 Alabama St, Winchester, KY 40391

  Step back in time and discover the possibilities in this classic 1930-built home full of character and opportunity! With solid bones and vintage details, this property is the perfect canvas for investors, renovators, or anyone dreaming of restoring a piece of history. Featuring spacious rooms, original architectrual touches, and a layout just waiting to be reimagined. This home offers incredible

  A. Rebecca Woods Woods Realty Group

  101 Alabama St, Winchester, KY 40391
• 

  

  /47

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft

  23 Kittison Dr, Winchester, KY 40391

  ONE-OWNER BRICK RANCH HOME!! Now that I have your attention, schedule a showing quickly, this one won't last long!! This cozy home has 3 spacious bedrooms, 2 bath, and a family room and kitchen area that are wonderful for family gatherings. You will love the beautiful hardwood floors throughout the home. Don't forget the garage /workshop area out back with room to grow if needed.

  Teresa Richmond Freedom Realty & Property Management

  23 Kittison Dr, Winchester, KY 40391
• 

  

  /101

  $1,290,000

  • 5 Beds
  • 5 Baths
  • 5,666 Sq Ft

  3760 Old Boonesboro Rd, Winchester, KY 40391

  Step through the striking red front doors and into a home where craftsmanship, character, and comfort come together. This beautifully maintained property sits on nearly 13 acres at the edge of Winchester, offering a peaceful retreat with the charm of a mid century floorplan and rich woodwork, tile, and hardwood floors throughout. The spacious kitchen and all three full baths feature high end

  Josh Wood Freedom Realty & Property Management

  3760 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /67

  $307,900

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft

  118 Windridge Dr, Winchester, KY 40391

  Enjoy rest, relaxation and all the outdoor activities you can dream up with this home. Cozy, 3-bedroom, 2-bathroom home ranch with attached one car garage in a well-established neighborhood. Home features new gas stove & range hood, new bathroom updates, hardwood floors, pocket doors, updated finishes, ventless gas fireplace, sunroom and professionally maintained in-ground pool with concrete

  Amber Hunt Whalen & Company

  118 Windridge Dr, Winchester, KY 40391
• 

  

  /33

  $219,900

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft

  21 Kentucky St, Winchester, KY 40391

  Updated, move-in ready, and right in the heart of Winchester. This is the kind of home that checks boxes and feels good the second you walk in. Start your mornings or wind down in the evenings on the inviting covered front porch—it's the kind of space that makes you want to slow down for a minute. Inside, everything has been updated so you can skip the projects and just enjoy your home from day

  Jenny Mateyoke Keller Williams Legacy Group

  21 Kentucky St, Winchester, KY 40391
• 

  

  /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
• 

  

  /58

  $239,900

  • 3 Beds
  • 2 Baths
  • 1,148 Sq Ft

  3610 Stamper Dr, Winchester, KY 40391

  You will absolutely love this well cared for and wonderfully updated ranch! This home has been lovingly cared for, is beautiful inside and out, and is absolutely ready to move into! Enjoy a large Eat-In kitchen with new granite countertops ( ten year warranty), and a marvelous, deep sink, stainless steel appliances, lots of cabinet space and more! You will find all new paint throughout the house

  Peter doCouto Plum Tree Realty

  3610 Stamper Dr, Winchester, KY 40391
• 

  

  /30

  $174,900

  • 2 Beds
  • 2 Baths
  • 1,122 Sq Ft

  403 Country Club Dr, Winchester, KY 40391

  Charming and recently updated, this 1.5-story townhome is located in the Spencer Community Development Subdivision. Offering 2 bedrooms and 2 full bathrooms, this home sits on a generous 0.37 acre lot. Inside, you'll find a beautifully remodeled interior with brand new vinyl flooring, fresh paint, and stylish new light fixtures. The completely updated kitchen boasts modern cabinetry and stainless

  Edgar Saborit Lifstyl Real Estate

  403 Country Club Dr, 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
• 

  

  /36

  $435,000

  • 4 Beds
  • 2 Baths
  • 1,692 Sq Ft

  3886 Jackson Ferry Rd, Winchester, KY 40391

  Take in the scenery, enjoy the quite county life, sitting on 5 acres, this brick ranch home offers easy living and peaceful country life. Four Bedrooms 2 full updated baths, Primary Suite with walk in closet, hardwood floors, beautiful brick fireplace in Living Room with Vaulted ceiling and built in shelving, Dining Room, Kitchen with breakfast area granite counter tops and all appliances (range,

  Whitney Ensor Ensor Real Estate, LLC

  3886 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /16

  $179,900

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

  47 Buckner St, Winchester, KY 40391

  This 3-bedroom, 2 full bath home is nestled in a convenient location and ready for new owners. Updates can be admired throughout. Property boats spacious bedrooms including primary bedroom with on-suite, large back yard with garage and so much more. Schedule your showing today!

  Michael Hilario The Agency

  47 Buckner St, 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
• 

  

  /15

  $139,900

  • 2 Beds
  • 1 Bath
  • 986 Sq Ft

  174 Cook Ave, Winchester, KY 40391

  Charming Fixer-Upper with Endless Potential - Priced to Sell!! This older gem is full of character and opportunity! Featuring solid bones and classic charm, this property is perfect for buyers with a vision who are not afraid to add a little TLC! Whether you're an investor, DIY entusiast, or someone dreaming of restoring a home to its former glory, this is your chance to build equity and create

  A. Rebecca Woods Woods Realty Group

  174 Cook Ave, 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
• 

  

  /31

  $145,000

  • 3 Beds
  • 1 Bath
  • 1,160 Sq Ft

  730 Byrd Ave, Winchester, KY 40391

  Full of opportunity on a large lot! With mostly cosmetic updates needed, this is an ideal project for a flip or a rental refresh. The layout and lot size provide flexibility, and this property has excellent potential to add value quickly. Being sold as-is.

  Patricia Weiderman Kentucky Land and Home

  730 Byrd Ave, Winchester, KY 40391
• 

  

  /12

  $160,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  471 Goose Creek Rd, Winchester, KY 40391

  CASH BUYERS! This 3-bedroom, 2-bath manufactured home on 1.49 acres offers strong potential for those looking to renovate, rent, or resell. Property is being sold as-is and will require repairs, making it best suited for cash buyers. Located just minutes from I-64 and convenient to Lexington, this property combines rural privacy with accessibility — a desirable combination for future resale or

  Shari Frasure Keller Williams Commonwealth

  471 Goose Creek Rd, Winchester, KY 40391
• 

  

  /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
• 

  

  /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
• 

  

  /63

  $460,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Enjoy peaceful country living on 17 beautiful acres in Clark County! This 3-bedroom, 2-bath ranch home sits on a scenic stretch of Trapp-Goffs Corner Road and offers the perfect blend of privacy, space, and convenience just minutes from Winchester and an easy drive to Lexington. The home features comfortable main-level living with a functional layout and a partially finished basement that

  Cheri Shaffer Lifstyl Real Estate

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  

  /76

  $149,000

  • 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
• 

  

  /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
• 

  

  /36

  $369,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  133 Shala-Mar Rue, Winchester, KY 40391

  Welcome to your next home in one of Clark County's most sought after communities—Shala Mar Estates. This beautifully updated 3-bedroom, 2-bathroom residence offers the perfect blend of comfort, style, and modern convenience. The expansive primary suite is a true retreat, featuring a stunning ensuite bathroom with a brand new soaking tub and a separate tiled shower. Two additional bedrooms provide

  Nena Honaker Tom Goebel & Company

  133 Shala-Mar Rue, Winchester, KY 40391
• 

  

  /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
• 

  

  /55

  $334,900

  • 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
• 

  

  /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
• 

  

  /44

  $349,500 Open Sun 2PM - 4PM

  • 4 Beds
  • 3 Baths
  • 3,440 Sq Ft

  221 W Hickman St, Winchester, KY 40391

  Step into a home where history and beauty meet in the most charming way. This stunning, fully remodeled historic home offers over 3,400 square feet of thoughtfully renewed living space, blending timeless character with elegant modern updates. From the moment you walk inside, you'll feel the warmth and romance of a home that has been lovingly restored while still honoring its original charm.

  Brandon Hedinger Keller Williams Bluegrass Realty

  221 W Hickman St, Winchester, KY 40391
• 

  

  /49

  $350,000

  • 3 Beds
  • 2.5 Baths
  • 2,628 Sq Ft

  221 Moundale Ave, Winchester, KY 40391

  Step back in time as you walk up the stone steps into this beautiful 3 bed 2.5 bath house. This house has been very well maintained and offers many updates. You get the best of both worlds the craftsmanship of an older home with all the newer amenities. Hardwood, tile and brick floors throughout the house with Granite countertops, This house sits on a lot and a half. The owners have recently

  Andrew Fugitt Coldwell Banker McMahan

  221 Moundale 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
• 

  

  /17

  $425,000

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft

  104 Colby Hills Dr, Winchester, KY 40391

  (Reducted 50,000) for fast sell. Welcome to this beautiful ranch home, located in this desirable Colby Hill subdivision this house has been updated with new interior painting, new flooring, new kitchen cabinets, and tops, new bathrooms, large new lighting, 2 car garage, 2 fireplaces, living room, family room, dinning area, large new deck ,all this on a large corner lot. Owner/Broker

  Garry Milton Milton and Associates Real Estate

  104 Colby Hills Dr, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 3