Newest Homes for Sale in Winchester, KY

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  /29

  $289,000

  • 5 Beds
  • 2 Baths
  • 1,838 Sq Ft

  426 E Broadway St, Winchester, KY 40391

  Welcome home to this beautifully reimagined property in Winchester! Originally built in 1945, this 1.5-story home has been completely transformed from the ground up, offering the perfect blend of classic charm and modern peace of mind. With approximately 1,838 square feet, this home has been fully gutted to the studs and thoughtfully rebuilt—featuring all-new electrical, plumbing, HVAC system,

  Alyssa M Boley Coldwell Banker McMahan

  426 E Broadway St, Winchester, KY 40391
• Explore Winchester

• 

  

  

  /26

  $369,900

  • 4 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  614 Colby Ridge Blvd, Winchester, KY 40391

  Welcome to this beautifully maintained 4 bed 2.5 bath home built in 2020 offering the perfect blend of modern design and everyday comfort. Open-concept once you step inside with lots of space. The kitchen and dining offers entertainment space along with the back deck. Check out this house. Located right behind Kroger close to everything and more.

  Stacey Dunaway HomeLand Real Estate Inc - Mt Sterling

  614 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  

  /11

  $155,000

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  19 3rd St, Winchester, KY 40391

  3BR/1BA | Winchester, KY Affordable single-family homes are hard to come by at this price — here's your chance. This cozy 3-bedroom, 1-bath home in Winchester sits on a generous lot with a large backyard, long driveway with plenty of parking, a welcoming covered front porch, and accessible front entry with both steps and a ramp. it's efficient and easy to maintain — and don't let the square

  Anthony Gigilo ListWithFreedom.com

  19 3rd St, 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
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  /59

  $335,000

  • 4 Beds
  • 2.5 Baths
  • 2,513 Sq Ft

  201 Boone Ave, Winchester, KY 40391

  Beautifully updated historic cottage-style home in Winchester's Historic Thomson Neighborhood featuring a recently updated wraparound front porch, and a new roof installed in September 2024. Inside, this character-filled home offers original hardwood floors, tall ceilings, classic millwork, four decorative fireplaces, a spacious, updated kitchen, and a formal dining room. Just off the

  Donna Woeste Rector Hayden Realtors

  201 Boone Ave, 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
• 

  

  /57

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  220 Hibiscus Ln, Winchester, KY 40391

  Welcome home to this immaculate gem nestled in the charming Hibiscus Terrace Subdivision! This beautifully maintained three-bedroom, two-bathroom home offers 1,640 square feet of thoughtfully designed living space that blends comfort with everyday functionality. Inside, discover a warm, inviting interior where fresh carpet installed in 2022 greets you with plush softness throughout. The

  Timothy Saylor Threshold Real Estate Services

  220 Hibiscus Ln, Winchester, KY 40391
• 

  

  /27

  $388,000

  • 8 Beds
  • 8 Baths
  • 4,000 Sq Ft

  17 W Lexington Ave, Winchester, KY 40391

  Great investment opportunity right in heart Downtown Winchester!!! Welcome to this income producing apartment complex of 8 studio apartments. Two levels of apartments, 4 on the first floor and 4 on the second. Each unit features a living area, full kitchen, and full bathroom. 5 units are currently rented out. The roof was put on 2 years ago. The basement has 2 entrances and could easily be

  Libby VanMeter Marshall Lane Real Estate - Lexington

  17 W Lexington Ave, Winchester, KY 40391
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  /32

  $222,500

  • 4 Beds
  • 1.5 Baths
  • 2,450 Sq Ft

  34 Hays St, Winchester, KY 40391

  This spacious 4-bedroom bungalow is tucked away in downtown Winchester in a great walkable location. Located less than a 5-minute walk to the College Park recreation center. This charming home blends timeless character with modern comfort. The kitchen and baths have been updated. The main living space has the original hardwood flooring and new flooring throughout the remaining house. The living

  Vickie Skeens RE/MAX Elite Lexington

  34 Hays St, Winchester, KY 40391
• 

  

  /33

  $209,900

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  59 Holiday Rd, Winchester, KY 40391

  Don't Wait - this home is priced to Sell! All one level brick ranch features 3 Bedrooms, 1-bath. Newer updates include interior paint and laminate flooring giving the home a clean modern feel. The living spaces are filled with natural light, making the home feel warm and inviting. Step out to a spacious deck and large backyard - great for entertaining or just enjoying the outdoor space. Need

  Kathy Burton Coldwell Banker McMahan

  59 Holiday Rd, Winchester, KY 40391
• 

  

  /33

  $339,900

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft

  740 Pilot Ridge Ln, Winchester, KY 40391

  Tucked away on 1.25 fully fenced acres, this custom-built home offers some of the most breathtaking views in Winchester. Designed with charm and comfort in mind, this 3-bedroom, 2.5-bath home blends modern convenience with timeless farmhouse style. Step inside to an open, inviting layout filled with natural light and warm finishes throughout. The spacious vaulted master suite is a true retreat,

  Holly Goeing The Agency

  740 Pilot Ridge Ln, Winchester, KY 40391
• 

  

  /33

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,634 Sq Ft

  402 Harney Dr, Winchester, KY 40391

  This well-kept split-level home in the Westmeade neighborhood offers a practical layout in a location that's close to the bypass, restaurants, and shopping. Upstairs, you'll find a roomy living area with a freestanding electric fireplace, along with an open kitchen and dining space. There are also three bedrooms and a full shared bathroom on this level. Downstairs, you'll find a finished basement

  Michelle Blackburn RE/MAX Creative, Winchester

  402 Harney Dr, Winchester, KY 40391
• 

  

  /72

  $775,000

  • 5 Beds
  • 3 Baths
  • 4,437 Sq Ft

  465 Morris Rd, Winchester, KY 40391

  Dreaming of wide-open spaces and country charm? This beautiful 16-acre property in Clark County offers the perfect blend of comfort and functionality. The stately brick home provides generous living space with classic appeal, offering endless potential. With five bedrooms and three full baths, the home accommodates a variety of living arrangements, whether you need space for guests, a home

  

  Brenda Leigh Walters

  United Real Estate Bluegrass

  (859) 459-0504

  465 Morris Rd, 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
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  /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
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  /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
• 

  

  /19

  $300,000

  • Land
  • 15.27 Acres
  • $19,652 per Acre

  4025 Jackson Ferry Rd, Winchester, KY 40391

  Opportunities like this are incredibly rare—15.266 combined acres backing to the Kentucky River, offering the ultimate private retreat. Located at the end of a scenic drive, these two tracts are being offered together, creating an expansive recreational property with unmatched access to the water. Ideal for camping, family getaways, or creating a multi-use outdoor haven, this land provides

  Christa Joynt Keller Williams Commonwealth

  4025 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /20

  $180,000

  • Land
  • 10.05 Acres
  • $17,919 per Acre

  3925 Jackson Ferry Rd, Winchester, KY 40391

  This 10.045-acre tract offers the total package...scenic surroundings, river access, and improvements already in place. Situated along a quiet, picturesque drive, the property features a solid barn that has recently been painted and structurally reinforced, adding both character and functionality. With a picturesque build site available, this land is ready for your dream home, hobby farm, and

  Christa Joynt Keller Williams Commonwealth

  3925 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /54

  $749,900

  • 3 Beds
  • 3.5 Baths
  • 3,388 Sq Ft

  1480 Irvine Rd, Winchester, KY 40391

  Beautifully remodeled farmhouse on 10 fenced acres! This 3 bedroom, 3.5 bath home with a fully finished basement offers the perfect blend of modern upgrades and country living. Inside, you'll find refinished hardwood floors and fresh paint throughout. The custom kitchen is designed to impress with new cabinetry, granite countertops, glass subway tile backsplash, double ovens, two dishwashers, and

  Ivanna Barko National Real Estate

  1480 Irvine Rd, Winchester, KY 40391
• 

  

  /16

  $97,500

  • Land
  • 7.99 Acres
  • $12,201 per Acre

  3991 Jackson Ferry Rd, Winchester, KY 40391

  Offering the same peaceful setting and rare river access, this tract provides a fantastic opportunity for recreational land ownership at an affordable price. Backing directly to the Kentucky River, it's an ideal spot for camping, weekend retreats, arrowhead hunting or enjoying the outdoors with kayaking, fishing, and more right at your fingertips. This property's fertile soil opens the door for

  Christa Joynt Keller Williams Commonwealth

  3991 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /22

  $150,000

  • Land
  • 9.39 Acres
  • $15,971 per Acre

  3821 Jackson Ferry Rd, Winchester, KY 40391

  If you've been dreaming of building a home with river access, this is it. Located along a breathtaking stretch of Jackson Ferry Road, this 9.392-acre tract offers a rare combination of a viable build site and direct access to the scenic Kentucky River. Whether it's morning coffee overlooking the countryside or afternoons spent kayaking and fishing, this property delivers a lifestyle that's hard

  Christa Joynt Keller Williams Commonwealth

  3821 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /15

  $97,500

  • Land
  • 8.46 Acres
  • $11,522 per Acre

  3961 Jackson Ferry Rd, Winchester, KY 40391

  Escape to your own slice of Kentucky countryside with this 8.462-acre tract nestled along a scenic stretch of Jackson Ferry Road. Backing up to the Kentucky River, this property is perfect for recreational use, whether you're looking to camp, garden, or create a weekend getaway. This land provides plenty of space for campers and outdoor enjoyment throughout much of the year. The soil is rich and

  Christa Joynt Keller Williams Commonwealth

  3961 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /19

  $105,000

  • Land
  • 9.75 Acres
  • $10,767 per Acre

  3759 Jackson Ferry Rd, Winchester, KY 40391

  Tucked along a peaceful, scenic drive, this 9.752-acre tract offers a rare opportunity to own land backing directly to the beautiful Kentucky River. This parcel is the perfect recreational escape-ideal for parking a camper, weekend getaways, or creating your own private retreat. Spend your days kayaking, canoeing, fishing, or paddle boarding right from your property, then unwind surrounded by

  Christa Joynt Keller Williams Commonwealth

  3759 Jackson Ferry Rd, 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
• 

  

  /25

  $425,000

  • Land
  • 25.87 Acres
  • $16,426 per Acre

  2996/3056 Irvine Rd, Winchester, KY 40391

  Rare opportunity to own over 25 acres of beautiful Kentucky countryside on Irvine Road, combining two adjoining tracts into one exceptional offering. With gently rolling hills and multiple ideal building sites, this property provides the perfect setting to create your dream home, private estate, or mini-farm. The land offers a wonderful balance of usability and natural beauty, featuring a scenic

  Christa Joynt Keller Williams Commonwealth

  2996/3056 Irvine Rd, Winchester, KY 40391
• 

  

  /20

  $175,000

  • Land
  • 11.36 Acres
  • $15,402 per Acre

  2996 Irvine Rd, Winchester, KY 40391

  Discover the perfect blend of convenience and countryside charm with this beautiful 11+ acre tract located just outside of Winchester in Clark County. Offering gently rolling terrain and multiple potential building sites, this property provides an ideal setting for your dream home, mini-farm, or private retreat.Enjoy the peace and privacy of rural living without sacrificing accessibility and just

  Christa Joynt Keller Williams Commonwealth

  2996 Irvine Rd, 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
• 

  

  /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
• 

  

  /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
• 

  

  /4

  $137,500

  • Land
  • 3.94 Acres
  • $34,898 per Acre

  150 Spencer Ln, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it grows in value. Offering unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by

  Kathryn Cheuvront Coldwell Banker McMahan

  150 Spencer Ln, Winchester, KY 40391
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  /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
• 

  

  /15

  $925,000

  • Land
  • 3.77 Acres
  • $245,358 per Acre

  300 Rolling Hills Ln, Winchester, KY 40391

  Great location just off exit 96 on I-64 and easy access to the Mountain Parkway. Only 15 minutes from I-75. Located near the entrance to the Winchester Kentucky Industrial Park. 3.774 flat acres to build your next business location.

  Josh Wood Freedom Realty & Property Management

  300 Rolling Hills Ln, Winchester, KY 40391
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /11

  $50,000

  • Land
  • 0.41 Acre
  • $121,951 per Acre

  308 Duclair Dr, Winchester, KY 40391

  Tucked away on a quiet cul-de-sac in Mallard Place, this .41-acre lot is ready for your vision. Imagine your dream home in a neighborhood known for its charm and convenience. Bring your house plans—your future starts here!

  Joseph Miller Keller Williams Legacy Group

  308 Duclair Dr, 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
• 

  

  /59

  $695,000

  • 3 Beds
  • 4 Baths
  • 4,008 Sq Ft

  1775 Irvine Rd, Winchester, KY 40391

  Absolutely fabulous all brick home with incredible views, one owner, what makes this home special is the feeling of elegance, a total renovation offers the ultimate in living, spacious lower level provides full bath, family room, firepalce, walk out door to a large patio, first level dining room, great room with firepalce, showcase kitchen, living room, upstairs with large master suite, side

  Mila Ensor Ensor Real Estate, LLC

  1775 Irvine Rd, Winchester, KY 40391
• 

  

  /36

  $215,000

  • 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

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