Winchester, KY Homes

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  /39

  $155,000 Sold Apr 24, 2025

  • 953 Sq Ft
  • $163/SF
  • 207 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1961

  10 Sylvania Ave, Winchester, KY 40391

  Come check out this sweet home that would make a perfect starter! All one level with a recently updated front porch, and a new roof/awning over the back patio, this home with a fully fenced in back yard will be the perfect oasis for summer and fall evenings. Keep the wood stove for an alternate heat source or switch it out for more space in the living room. Enjoy the original hardwood floors and

  Christa Joynt Keller Williams Commonwealth

  10 Sylvania Ave, Winchester, KY 40391
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  /79

  Est $432,550 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,494 Sq Ft

  421 Lynnway Dr, Winchester, KY 40391

  421 Lynnway Dr, Winchester, KY 40391
• 

  

  

  /70

  $999,900

  • 5 Beds
  • 4 Baths
  • 4,058 Sq Ft

  2447 Clintonville Rd, Winchester, KY 40391

  What a great opportunity to own 3 acres just 15 minutes from Man O War and 20 minutes to the Hamburg Shopping Area. The move in ready property features a beautiful brick home built by builder, Michael Childers, to use as his main residence. The property also has a 3 car detached Garage which is deep enough to hold 6 cars and one door is tall for storage of a Recreational Vehicle. It has been

  Suzanne Elliott Berkshire Hathaway de Movellan Properties

  2447 Clintonville Rd, Winchester, KY 40391
• 

  

  

  /19

  $220,000 Sold Apr 23, 2025

  • 1,200 Sq Ft
  • $183/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  112 Central Ave, Winchester, KY 40391

  NEW CONSTRUCTION! Located just steps from Winchester's charming downtown area, you'll have access to shops, restaurants, local events and more. This beautiful home offers 3 bedrooms, 2 baths, sleek modern kitchen with granite counter tops and stainless still appliances. At $217,000, this home offers unbeatable value for a brand-new construction in a well-established neighborhood in downtown

  Nena Honaker Tom Goebel & Company

  112 Central Ave, Winchester, KY 40391
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  /36

  Est $480,715 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,804 Sq Ft

  227 Casa Landa Way, Winchester, KY 40391

  227 Casa Landa Way, Winchester, KY 40391
• 

  

  /15

  $53,000

  • Land
  • 6 Acres
  • $9,481 per Acre

  199 Midway Rd, Winchester, KY 40391

  Introducing this 5.59 acre property in Central Kentucky! With city water and electric available at the road, this land offers a seamless transition for your dream home or investment project. Located just 15 minutes from Winchester, 30 minutes from Hamburg, and 30 minutes from Mt. Sterling. You will enjoy easy access to city amenities while relishing the peace of rural living. Don't miss the

  Skyler Lewis Dream Maker Realty, LLC

  199 Midway Rd, Winchester, KY 40391
• 

  

  /29

  $385,000 Sold Apr 21, 2025

  • 2,800 Sq Ft
  • $138/SF
  • 25 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1982

  1623 Little Stoner Rd, Winchester, KY 40391

  A ranch house on a basement with 7 Acres sounds like an ideal setup for someone who wants space, privacy, and the potential for a variety of activities! The combination of a ranch-style home and basement gives you flexibility-whether it's extra storage, living space, or even a potential hobby area. A Must See!

  Sharon Ben David Berkshire Hathaway de Movellan Properties

  1623 Little Stoner Rd, Winchester, KY 40391
• 

  

  /72

  Est $467,037 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,162 Sq Ft

  16 Heritage Place, Winchester, KY 40391

  16 Heritage Place, Winchester, KY 40391
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  /4

  $139,900

  • Land
  • 6 Acres
  • $24,674 per Acre

  1445 Gay Evans Rd, Winchester, KY 40391

  Welcome to The Retreat at Juett Farms! Come build your dream home on some of the best land that Clark County has to offer. This peaceful setting with unparalleled views of the countryside, is sure to impress. Imagine sitting on your front porch taking in the most amazing sunsets! This beautiful parcel has over 5 acres of unrestricted land. Schedule your showing today!

  Holly Goeing The Agency

  1445 Gay Evans Rd, Winchester, KY 40391
• 

  

  /19

  $175,000 Sold Apr 18, 2025

  • 1,188 Sq Ft
  • $147/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  11 Shelley Dr, Winchester, KY 40391

  Investors take a look! 3 bedrooms, 2 bathrooms brick ranch on full unfinished basement with large 2 car detached garage & large, covered patio on back of home. Hardwood flooring, updated bathrooms, one with walk-in shower, newer roof and newer HVAC system. Home is selling As-Is but inspections are welcome.

  Tonya Morrow KY Local

  11 Shelley Dr, Winchester, KY 40391
• 

  

  /32

  Est $405,468 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,367 Sq Ft

  20 Edgewood Dr, Winchester, KY 40391

  20 Edgewood Dr, Winchester, KY 40391
• 

  

  /4

  $149,900

  • Land
  • 6 Acres
  • $26,768 per Acre

  1541 Gay Evans Rd, Winchester, KY 40391

  Welcome to The Retreat at Juett Farms! Come build your dream home on some of the best land that Clark County has to offer. This peaceful setting with unparalleled views of the countryside, is sure to impress. Imagine sitting on your front porch taking in the most amazing sunsets! This beautiful parcel has over 5 acres of unrestricted land. Schedule your showing today!

  Holly Goeing The Agency

  1541 Gay Evans Rd, Winchester, KY 40391
• 

  

  /27

  $190,000 Sold Apr 18, 2025

  • 1,550 Sq Ft
  • $123/SF
  • 7 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1969

  7 Pocahontas Trail, Winchester, KY 40391

  Step inside this raised ranch, sun filled rooms, hardwood in most of the upstairs, kitchen with all the appliances, washer/dryer stay, large detached garage, hot tub on covered deck, great space in back yard, some fencing, lovely home close to historic downtown Winchester, not far from I-75 and I-64, shopping, church, schools, large partial finished walkout basement, call today this one won't

  Mila Ensor Ensor Real Estate LLC

  7 Pocahontas Trail, Winchester, KY 40391
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  /84

  Est $583,925 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,695 Sq Ft

  107 Camelot Dr, Winchester, KY 40391

  107 Camelot Dr, Winchester, KY 40391
• 

  

  /28

  $799,900

  • Land
  • 13 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 road 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

  Josh Wood Freedom Realty & Property Mgt

  1600 Ironworks Rd, Winchester, KY 40391
• 

  

  /87

  $250,000 Sold Apr 18, 2025

  • 1,680 Sq Ft
  • $149/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1996

  418 Jameson Way, Winchester, KY 40391

  Welcome to this charming split-level home in Maple Ridge subdivision! Designed with comfort and convenience in mind, this home features an updated eat-in kitchen with granite countertops, an all purpose kitchen island that fits 2 barstools and a stylish tiled backsplash. All bedrooms are on the first level, complete with your very own primary bathroom. The inviting living room offers a cozy

  Josh Wood Freedom Realty & Property Mgt

  418 Jameson Way, Winchester, KY 40391
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  /33

  Est $413,885 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  505 Colby Rd, Winchester, KY 40391

  505 Colby Rd, Winchester, KY 40391
• 

  

  /4

  $140,000

  • Land
  • 3.94 Acres
  • $35,533 per Acre

  12569 Ironworks Rd, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! These two parcels totaling 3.94 acres, offer 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 the beauty and tranquility. Don't miss your opportunity to own prime land with unmatched potential!

  Kathryn Cheuvront Coldwell Banker McMahan

  12569 Ironworks Rd, Winchester, KY 40391
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  /49

  $442,500 Sold Apr 18, 2025

  • 3,882 Sq Ft
  • $114/SF
  • 134 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 2005

  321 Frontier Way, Winchester, KY 40391

  OPEN HOUSE Saturday 3/1/25 2-4pm. Apart from home being in a great location, right across the street from the Elementary School, home is minutes from shopping, food and entertainment (Applebees,Woody's Bar and Grill, Tjmaxx, Kroger, Movie Theatre, Ft. Boonesborough) & only a 20 minute drive to Hamburg in Lexington or 15 miutes to Mt. Sterling. This beautiful home is complete with a newly finished

  Olivia White Deborah Ball Realty

  321 Frontier Way, Winchester, KY 40391
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  /47

  Est $337,061 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,570 Sq Ft

  206 Carter Dr, Winchester, KY 40391

  206 Carter Dr, Winchester, KY 40391
• 

  

  /32

  $335,000

  • 3 Beds
  • 1.5 Baths
  • 1,356 Sq Ft

  4074 Ironworks Rd, Winchester, KY 40391

  Welcome to country living! This newly renovated ranch on 4+ scenic acres offers peaceful living just 10 minutes from town. Inside, the open floor plan seamlessly connects the kitchen, dining, and living areas. The kitchen features granite countertops, new stainless steel appliances, a central island with bar seating, while the living room boasts a cozy fireplace. Durable LVP and tile flooring run

  Michelle Blackburn RE/MAX Creative, Winchester

  4074 Ironworks Rd, Winchester, KY 40391
• 

  /2

  $110,000 Sold Apr 18, 2025

  • Land
  • 0.59 Acre
  • $186,441 per Acre

  • 847 Days On Market

  210 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  210 Duclair Dr, Winchester, KY 40391
• 

  

  /32

  Est $224,589 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  17 Maryland Ave, Winchester, KY 40391

  17 Maryland Ave, Winchester, KY 40391
• 

  

  /9

  $785,000

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft

  425 Alexis Way, Winchester, KY 40391

  Introducing the Highland, an elegant all-brick ranch home offering 4 bedrooms and 2.5 full baths in a thoughtfully designed split-bedroom layout. The spacious primary suite is a true highlight, featuring a luxurious tile shower, separate soaking tub, double vanities, and a large walk-in closet. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for

  Shane Underwood Keller Williams Commonwealth

  425 Alexis Way, Winchester, KY 40391
• 

  

  /34

  $260,000 Sold Apr 17, 2025

  • 1,565 Sq Ft
  • $166/SF
  • 63 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1993

  597 Marseille Blvd, Winchester, KY 40391

  Welcome to this 3-bedroom, 2-bathroom ranch-style home conveniently located off McClure Road in a desirable neighborhood, perfect for those looking to create their dream space. The layout features a spacious yet cozy living area with a fireplace and a functional kitchen, ready for your personal touch. Step outside to a large fenced backyard that's perfect for outdoor activities, pets, or

  Michelle Blackburn RE/MAX Creative, Winchester

  597 Marseille Blvd, Winchester, KY 40391
• 

  

  /11

  Est $256,204 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,123 Sq Ft

  10 Arlington Rd, Winchester, KY 40391

  10 Arlington Rd, Winchester, KY 40391
• 

  

  /3

  $645,000

  • 4 Beds
  • 2.5 Baths
  • 2,526 Sq Ft

  106 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Claiborne Floor Plan by CP Builders. This stunning 4-bedroom, 2.5-bathroom home offers a luxurious and spacious living experience. The first floor features a magnificent primary suite complete with a spacious ensuite bathroom, a walk-in closet, and direct access to the backyard. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and

  Shane Underwood Keller Williams Commonwealth

  106 Bella Shae Way, Winchester, KY 40391
• 

  

  /17

  $390,000 Sold Apr 16, 2025

  • 1,854 Sq Ft
  • $210/SF
  • 73 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1983

  3750 Becknerville Rd, Winchester, KY 40391

  Are you longing for a quiet country home? A place to have a few farm animals, raise a garden and enjoy the peacefulness of living away from town. Presenting to you 3750 Becknerville Road. It checks all of the boxes! This lovely 5.5 acre mini farm is situated between Winchester and Lexington on a gorgeous, partially fenced tract, with amazing mature trees. With roughly 1850 square feet of living

  Holly Goeing The Agency

  3750 Becknerville Rd, Winchester, KY 40391
• 

  

  /58

  Est $243,237 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,358 Sq Ft

  203 Holiday Rd, Winchester, KY 40391

  203 Holiday Rd, Winchester, KY 40391
• 

  

  /3

  $670,000

  • 3 Beds
  • 2 Baths
  • 2,261 Sq Ft

  113 Bella Shae Way, Winchester, KY 40391

  Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen

  Shane Underwood Keller Williams Commonwealth

  113 Bella Shae Way, Winchester, KY 40391
• 

  

  /17

  $278,000 Sold Apr 15, 2025

  • 1,292 Sq Ft
  • $215/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2005

  218 Bracken Ct, Winchester, KY 40391

  Since warm weather is near you will love the updated huge back deck with new railing overlooking a large, fenced backyard. This spacious turnkey open concept 3-bedroom 2-bath home sitting on a .29-acre lot has been completely updated and ready for you to move in and enjoy. Since it is located in a cul-de-sac no worries regarding busy traffic. This budget friendly home has a newer roof less than

  Tonya Skeens RE/MAX Elite Lexington

  218 Bracken Ct, Winchester, KY 40391
• 

  

  /23

  Est $218,645 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  106 Holiday Rd, Winchester, KY 40391

  106 Holiday Rd, Winchester, KY 40391
• 

  

  /3

  $700,000

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  415 Alexis Way, Winchester, KY 40391

  Introducing the Merango, a classic all-brick ranch home designed for both comfort and style. With stunning double front doors and a 2-car attached garage, this home offers incredible curb appeal and modern living. The spacious 3-bedroom, 2-bath layout features a split-bedroom design for added privacy, along with a dedicated study perfect for a home office. The open-concept kitchen is ideal for

  Shane Underwood Keller Williams Commonwealth

  415 Alexis Way, Winchester, KY 40391
• 

  

  /16

  $240,000 Sold Apr 15, 2025

  • 1,350 Sq Ft
  • $178/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  13385 Ironworks Rd, Winchester, KY 40391

  Charming and move-in ready, this 3-bedroom, 2-bath ranch home on 1 acre offers the perfect blend of space, comfort, and convenience. The low-maintenance vinyl siding allows for easy upkeep, while the freshly painted interior creates a bright and inviting atmosphere. The large 10x20 covered rear porch provides the perfect spot to relax or entertain, with the potential to be converted into a

  Joshua Davis The Agency

  13385 Ironworks Rd, Winchester, KY 40391
• 

  

  /47

  Est $319,575 Not Listed For Sale

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

  106 Harkins Dr, Winchester, KY 40391

  106 Harkins Dr, Winchester, KY 40391
• 

  

  /4

  $635,000

  • 4 Beds
  • 2.5 Baths
  • 2,537 Sq Ft

  422 Alexis Way, Winchester, KY 40391

  Introducing the Denver, a gorgeous all-brick ranch home offering 4 bedrooms and 2.5 baths, designed for both luxury and practicality. With its stunning curb appeal, front porch, and beam accents, this home makes a lasting first impression. Inside, the split-bedroom layout offers privacy and space for everyone, with a large primary suite featuring a walk-in closet, soaking tub, separate shower,

  Shane Underwood Keller Williams Commonwealth

  422 Alexis Way, Winchester, KY 40391
• 

  

  /24

  $179,500 Sold Apr 11, 2025

  • 1,050 Sq Ft
  • $171/SF
  • 44 Days On Market

  • 2 Beds
  • 1 Bath

  606 College St, Winchester, KY 40391

  Imagine yourself in this stunning home, where classic charm blends seamlessly with modern sophistication. This lovely, remodeled ranch home is ready for you to make your own. As you step inside, you'll be greeted by an open concept living area, complete with a beautiful fireplace and built-ins that add warmth and character. The newly renovated kitchen is a culinary dream, boasting crisp white

  Angelica Hebert Lifstyl Real Estate

  606 College St, Winchester, KY 40391
• 

  

  /29

  Est $236,664 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,326 Sq Ft

  230 Holiday Rd, Winchester, KY 40391

  230 Holiday Rd, Winchester, KY 40391
• 

  

  /22

  $665,000

  • 3 Beds
  • 2.5 Baths
  • 2,643 Sq Ft

  414 Alexis Way, Winchester, KY 40391

  Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added

  Shane Underwood Keller Williams Commonwealth

  414 Alexis Way, Winchester, KY 40391
• 

  

  /16

  $221,000 Sold Apr 10, 2025

  • 1,053 Sq Ft
  • $210/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  717 Estes Dr, Winchester, KY 40391

  Cozy 3 Bed, 2 Bath ranch in Winchester, KY. This delightful home offers a perfect blend of comfort and convenience, located just minutes from shopping and only 25 minutes from Lexington. Ideal for anyone looking to enjoy the tranquility of suburban living while being close to city amenities. Enjoy the beauty of hardwood floors throughout the main living areas and bedrooms and plenty of extra

  Rebecca Worth Redfin

  717 Estes Dr, Winchester, KY 40391

Showing Results 401 - 440, Page 11 of 18