Winchester, KY Homes

• 

  

  

  /33

  $379,900 Sold Apr 25, 2025

  • 1,800 Sq Ft
  • $211/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2019

  151 Hawthorne Dr, Winchester, KY 40391

  This beautiful, one-owner ranch in a highly desired neighborhood is about to hit the market! With 3 bedrooms, 2 baths, and over 1,800 sq. ft., this home has been completely updated and is truly move-in ready. The brick and vinyl exterior keeps maintenance easy, while the covered front and back porches make the perfect spot to relax.Inside, the large primary suite offers a private retreat,

  Kymberly McCreary EXP Realty, LLC

  151 Hawthorne Dr, Winchester, KY 40391
• 

  

  

  /37

  Est $283,316 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,783 Sq Ft

  17 Short St, Winchester, KY 40391

  17 Short St, Winchester, KY 40391
• 

  

  

  /22

  $269,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  115 Ashley Dr, Winchester, KY 40391

  Well maintained 3 bedroom 2 bath ranch with a fenced in backyard and 2 car garage on a very desirable street! All one level! Not a single step on the entire property! Double driveway plus street parking! Open concept living / dining area connects to an enclosed sunroom on the back. Just minutes from shopping, dining, and the interstate. Third bedroom is non-conforming due to not having an egress

  Jason Townsend Kentucky Residential Real Estate, LLC

  115 Ashley Dr, Winchester, KY 40391
• 

  

  

  /16

  $225,000 Sold Apr 25, 2025

  • 943 Sq Ft
  • $239/SF
  • 2 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1968

  39 Hillcrest Dr, Winchester, KY 40391

  Looking for a house on one level, and in a conveniently located, established neighborhood? This ranch with an attached garage is one that you'll want to see! It has a large living room, 3 bedrooms, and a kitchen with dining area that leads out to a large patio. The fenced yard is wonderful for children or pets and there is a nice size storage shed. You don't want to miss this one! Schedule

  Tracey Goebel Tom Goebel & Company

  39 Hillcrest Dr, Winchester, KY 40391
• 

  

  

  /34

  Est $367,624 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,928 Sq Ft

  214 Boone Ave, Winchester, KY 40391

  214 Boone Ave, Winchester, KY 40391
• 

  

  /43

  $399,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,041 Sq Ft

  7236 Old Boonesboro Rd, Winchester, KY 40391

  This lovely brick ranch on a basement sits on a beautiful, secluded 3 acre lot with mature trees, a garden area, and perimeter fencing! One owner home that has been well maintained in a great location. Very private and peaceful! The main level features the primary bedroom and bathroom with a tile shower and large closet, living room, kitchen with dining area, large utility room, full bathroom,

  Jason Townsend Kentucky Residential Real Estate, LLC

  7236 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /34

  $174,000 Sold Apr 25, 2025

  • 1,655 Sq Ft
  • $105/SF
  • 44 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1940

  397 College St, Winchester, KY 40391

  Located just across from the spacious and fun College Park in the heart of Winchester, this home is awaiting new owners to breathe new life into it. There is a multi-purpose room on first level that seller planned as their primary bedroom. This stately Craftsman style house will make a wonderful home full of charm and character. The current owner has completed some renovations including

  Josh Wood Freedom Realty & Property Management

  397 College St, Winchester, KY 40391
• 

  

  /65

  Est $365,012 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,372 Sq Ft

  408 S Maple St, Winchester, KY 40391

  408 S Maple St, Winchester, KY 40391
• 

  

  /71

  $419,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft

  188 Big Stoner Rd, Winchester, KY 40391

  48 hr kick-out- Come home every day to this 2-story beauty! You need country life? Well here is it! A little over 1 acre to spread out & enjoy the outdoors w/farm views & beautiful sunsets in the evening. This home opens up to a huge living room with hardwood floors and a vaulted ceiling. Kitchen has all stainless steel appliances & granite counter tops. First floor has a primary suite

  Trina Penn RE/MAX Creative Realty

  188 Big Stoner Rd, Winchester, KY 40391
• 

  

  /88

  $740,000 Sold Apr 25, 2025

  • 2,146 Sq Ft
  • $345/SF
  • 88 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1997

  865 Sugar Ridge Rd, Winchester, KY 40391

  This is a meticulously built and cared for farm. From the gorgeous log home, pond behind, beautiful 8 stall barn, wash rack, Tack room, ramp to load into manure spreader, and indoor arena 110x 70, LED Lights, and a run in 14' overhang. Easy parking area for trailers and a very wide gate to access the barn area, separate from the house. This property is completely ready to move you and your

  Alysia Niva Century 21 Advantage Realty - Georgetown

  865 Sugar Ridge Rd, Winchester, KY 40391
• 

  

  /57

  Est $440,777 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,864 Sq Ft

  402 S Maple St, Winchester, KY 40391

  402 S Maple St, Winchester, KY 40391
• 

  

  /39

  $472,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,727 Sq Ft

  865 Pretty Run Rd, Winchester, KY 40391

  Situated on 1.5 acres along a sought after country road, this one level home features a split bedroom layout with a primary suite that includes an en suite bath and walk in closet. The living room offers vaulted ceilings, hardwood floors, and a gas log fireplace, opening to a dining area and an eat in kitchen. A sunroom provides additional living space with skylights and views of the backyard.

  Shane Underwood Keller Williams Commonwealth

  865 Pretty Run Rd, Winchester, KY 40391
• 

  

  /22

  $332,000 Sold Apr 25, 2025

  • 2,384 Sq Ft
  • $139/SF
  • 203 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  502 Hewlett Ct, Winchester, KY 40391

  OPEN HOUSE, Saturday, March 22, 2025 from 12-2Happiness is this two story home with lots of room, great corner lot, large patio for entertaining and grilling, great room, master bedroom with large closet, close to shopping, schools, hospital, restaurants, double garage, located on a cul-de-sac, call today!

  Mila Ensor Ensor Real Estate, LLC

  502 Hewlett Ct, Winchester, KY 40391
• 

  

  /60

  Est $438,065 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,718 Sq Ft

  405 Boone Ave, Winchester, KY 40391

  405 Boone Ave, Winchester, KY 40391
• 

  

  /37

  $949,950 Pending

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

  700 Nick Ln, Winchester, KY 40391

  🚨 BIG PRICE DROP ALERT! 🚨 Motivated sellers are ready to make a deal—this is your chance to snag an unbeatable offer! 💰🏡Step into country living with this amazing 120-acre working farm! You'll love the brand-new 3-bedroom, 2.5-bath home that features an open floor plan, perfect for hanging out with family or hosting friends. It's got all the modern touches, so you

  Darrell Tackett Dream Maker Realty, LLC

  700 Nick Ln, Winchester, KY 40391
• 

  

  /23

  $130,000 Sold Apr 24, 2025

  • 1,008 Sq Ft
  • $129/SF
  • 13 Days On Market

  • 2 Beds
  • 1.5 Baths

  103 Gary Ct, Winchester, KY 40391

  Why rent when you can BUY! This renovated townhouse is perfect and affordable for first time buyers not wanting to throw away their money. This home offers a large living/dining/ kitchen open floor plan with granite countertops , newer stainless steel appliances and check out the craftsmanship tongue & groove ceiling. There is newer LVP flooring throughout and the bathrooms have updated vanities.

  Dawn Wheeler United Real Estate Bluegrass

  103 Gary Ct, Winchester, KY 40391
• 

  

  /57

  Est $285,300 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,270 Sq Ft

  10 Northern Ave, Winchester, KY 40391

  10 Northern Ave, Winchester, KY 40391
• 

  

  /42

  $349,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,625 Sq Ft

  19 Snowfall Dr, Winchester, KY 40391

  Overlooking the 16th green of the Winchester Country Club, this mid-century modern ranch blends classic 1950 design with thoughtful modern updates. With 1,625 square feet, the home is light, bright, and designed for easy living.The kitchen features custom cabinetry, KitchenAid appliances, and updated flooring, while a stone fireplace with gas insert anchors the living area. Gleaming

  Bradford Queen Bluegrass Sotheby's International Realty

  19 Snowfall Dr, Winchester, KY 40391
• 

  

  /13

  $210,000 Sold Apr 24, 2025

  • 1,053 Sq Ft
  • $199/SF
  • 15 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1978

  28 Stefanie Ct, Winchester, KY 40391

  Discover this beautifully updated 3-bedroom, 1-bath all-brick ranch in Winchester—a fantastic find! From the durable metal roof and contemporary interior renovations to the workshop-ready outbuilding with electric, every detail has been thoughtfully upgraded. Enjoy low-maintenance tile floors throughout, upgraded electricity to 200 amp, new Carrier A/C and furnace, a refreshed backyard with new

  Angela Newby Calumet Realty

  28 Stefanie Ct, Winchester, KY 40391
• 

  

  /15

  Est $204,710 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,036 Sq Ft

  215 Short St, Winchester, KY 40391

  215 Short St, Winchester, KY 40391
• 

  

  /102

  $547,900 Pending

  • 6 Beds
  • 4.5 Baths
  • 3,846 Sq Ft

  1953 Cabin Creek Rd, Winchester, KY 40391

  ***Click on the Virtual Tour section to see the video walk through!*** This unique property includes not only one, but two beautiful homes in the heart of Kentucky Bluegrass country. The first home is a brick ranch with a covered front porch and back patio that overlook this beautiful piece of farm land. This 2046 sq ft home contains 3 bedrooms and 2 full baths with a large great room in the

  Josh Wood Freedom Realty & Property Management

  1953 Cabin Creek Rd, Winchester, KY 40391
• 

  

  /24

  $215,000 Sold Apr 24, 2025

  • 1,400 Sq Ft
  • $154/SF
  • 31 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2002

  445 Jameson Way, Winchester, KY 40391

  This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of AMI for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, HVAC, 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

  445 Jameson Way, Winchester, KY 40391
• 

  

  /38

  Est $415,307 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,470 Sq Ft

  26 Manor Dr, Winchester, KY 40391

  26 Manor Dr, Winchester, KY 40391
• 

  

  /64

  $369,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  309 Gallahadion Ct, Winchester, KY 40391

  This beautiful, new-construction home located in desirable Fairholme Estates is a must see!! Amazing open floor plan with kitchen granite countertops, a large island and upgraded Frigidaire Elite Stainless Appliances. The waterproof Pergo laminate flooring is throughout the home. The builder has installed window blinds throughout the home and stained the back deck. Don't miss the primary

  Josh Wood Freedom Realty & Property Management

  309 Gallahadion Ct, Winchester, KY 40391
• 

  

  /62

  $325,000 Sold Apr 24, 2025

  • 1,888 Sq Ft
  • $172/SF
  • 88 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1996

  138 Shanahan Ln, Winchester, KY 40391

  This wonderful ranch home is located in the Stoney Brook Subdivision off of Casa Landa Way and has been cared for and updated by the seller. Entry foyer opens to a great room that features a beautiful stone faced fireplace with new gas logs for cozy nights in the approaching winter months. Eating area off the great room with efficient kitchen area. New stainless appliances in 2024, include

  Christine McDonald FC Tucker Bluegrass

  138 Shanahan Ln, Winchester, KY 40391
• 

  

  /32

  Est $361,206 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,044 Sq Ft

  505 Boone Ave, Winchester, KY 40391

  505 Boone Ave, Winchester, KY 40391
• 

  

  /33

  $332,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft

  1831 Kiddville Rd, Winchester, KY 40391

  Offering a perfect blend of modern comfort, energy efficiency, and country charm. Conveniently located just 1.3 miles from Exit 10 off the Bert T. Combs Mountain Parkway, this property provides easy access to both natural beauty and city amenities, with Downtown Winchester only 15 miles away and Natural Bridge State Park just 27 miles down the road. The living area features a cozy vent-free gas

  Joshua Davis The Agency

  1831 Kiddville Rd, Winchester, KY 40391
• 

  

  /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
• 

  

  /35

  Est $363,789 Not Listed For Sale

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

  121 Hampton Ave, Winchester, KY 40391

  121 Hampton Ave, Winchester, KY 40391
• 

  

  /39

  $350,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,929 Sq Ft

  219 Hampton Ave, Winchester, KY 40391

  Open House-Sunday 3:30-5:30 This beautiful brick ranch-style home sits on a generous .31 acre lot -property extends to the right, well beyond the fenced area, reaching to the tree stump & pink flag, offering more space, & on a quiet dead end street with mature trees. The property features a natural stone front and partial stone skirt(added in 2023), enhancing its curb appeal. Inside, you'll

  Jo Gawthrop Keller Williams Bluegrass Realty

  219 Hampton Ave, 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
• 

  

  /27

  Est $226,612 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,598 Sq Ft

  118 Southern Ct, Winchester, KY 40391

  118 Southern Ct, Winchester, KY 40391
• 

  

  /11

  $194,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,110 Sq Ft

  322 Buffalo Trace, Winchester, KY 40391

  Handicap-accessible ranch home has exterior ramps out the front and rear, 36-inch wide all and doors, and a handicap-accessible hall bath with a tiled shower. The home has been freshly painted and cleaned. Brand new appliance package. No traffic, end-of-street location. Lots of recent improvements - ready for occupancy.

  Sondra Clark Taylor Real Estate, LLC

  322 Buffalo Trace, Winchester, KY 40391
• 

  

  /6

  $225,000 Sold Apr 22, 2025

  • Land
  • 8.59 Acres
  • $26,193 per Acre

  • 35 Days On Market

  845 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 8.5 acres of unrestricted land and 500+ feet of road frontage. Minutes from I-64 and a

  Holly Goeing The Agency

  845 Gay Evans Rd, Winchester, KY 40391
• 

  

  /46

  Est $347,361 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,676 Sq Ft

  14 Western Ave, Winchester, KY 40391

  14 Western Ave, Winchester, KY 40391
• 

  

  /49

  $109,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,386 Sq Ft

  33 Bon Haven Ave, Winchester, KY 40391

  Attention investors and DIY enthusiasts! Multiple exit strategies: finish this remodel then either flip, rent or move in! Home being sold as is. Cash preferred but will consider financed all offers. *Foundation work is needed.

  Dustin Hepburn

  33 Bon Haven Ave, 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
• 

  

  /37

  Est $279,485 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,853 Sq Ft

  120 Milwood Dr, Winchester, KY 40391

  120 Milwood Dr, Winchester, KY 40391
• 

  

  /40

  $269,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,736 Sq Ft

  58 Fitch Ave, Winchester, KY 40391

  Fully Remodeled 4-Bedroom Home Across from College Park!Welcome to this beautifully remodeled 4-bedroom, 2.5-bath home perfectly located right across the street from College Park. From top to bottom, this home has been thoughtfully updated with modern finishes and a fresh, open layout ideal for comfortable living and entertaining.Step inside to find a light-filled interior

  Andrea Coughtry Lifstyl Real Estate

  58 Fitch Ave, 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

Showing Results 641 - 680, Page 17 of 18