Homes for Sale in 40391

• 

  

  

  /22

  $225,000

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  443 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 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

  443 Jameson Way, Winchester, KY 40391
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• 

  

  

  /25

  $248,000

  • 3 Beds
  • 2.5 Baths
  • 1,342 Sq Ft

  120 Jackson St, Winchester, KY 40391

  Step into modern comfort just minutes from the heart of downtown Winchester. This nearly new home blends contemporary style with timeless charm. Featuring bright, open living spaces, and thoughtful upgrades throughout, it offers a move-in-ready opportunity in one of Winchester's most convenient locations.

  Hannah Toole Coldwell Banker McMahan

  120 Jackson St, Winchester, KY 40391
• 

  

  

  /30

  $230,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  2721 Pretty Run Rd, Winchester, KY 40391

  Back on market due to buyer financing, no fault of the seller! Situated on 5 scenic acres along a highly sought-after country road, this 3-bedroom, 2-bath property presents an excellent opportunity to create your dream rural retreat. The home features a functional layout with a spacious living area, an eat-in kitchen, and a primary suite with its own bath. Two additional bedrooms offer

  Michelle Blackburn RE/MAX Creative, Winchester

  2721 Pretty Run Rd, Winchester, KY 40391
• 

  

  

  /87

  $3,100,000

  • 3 Beds
  • 3 Baths
  • 3,693 Sq Ft

  3049 Ironworks Rd, Winchester, KY 40391

  First time offered - in the same family since 1803! This 150-acre Clark County cattle farm is a rare blend of history, natural beauty, and potential. Fully fenced with an automatic watering system, four barns, two storage sheds, four ponds and a creek, this property is ready for livestock, agriculture, or outdoor pursuits. Two home sit on the property: a 2322 Sq.Ft. ranch with a 1371 Sq.Ft

  Zova Rothchild Keller Williams Legacy Group

  3049 Ironworks Rd, Winchester, KY 40391
• 

  

  

  /23

  $255,000

  • 3 Beds
  • 2.5 Baths
  • 1,416 Sq Ft

  208 Watercrest Way, Winchester, KY 40391

  Welcome home! This charming 3 bedroom, 2.5 bath property offers comfort and style with thoughtful updates, a 1-car garage, and a spacious fenced yard with covered deck. Enjoy a view of the large backyard from your eat-in kitchen that features a tiled backsplash and new appliances. Primary bedroom includes a new tiled shower and multiple closets. Second and third bedrooms conveniently share a full

  Chad Bowman The Brokerage

  208 Watercrest Way, Winchester, KY 40391
• 

  

  /55

  $318,500

  • 4 Beds
  • 1.5 Baths
  • 2,170 Sq Ft

  214 S Burns Ave, Winchester, KY 40391

  Own a beautifully maintained piece of Winchester, KY history on desirable South Burns Avenue. This charming home features an inviting wrap-around porch perfect for year-round enjoyment and outstanding curb appeal. Step into a warm and welcoming entryway where refinished hardwood floors flow throughout the main level. Original pocket doors open into the library, showcasing the home's timeless

  Christa Joynt Keller Williams Commonwealth

  214 S Burns Ave, Winchester, KY 40391
• 

  

  /15

  $210,000

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft

  246 Geronimo Ct, Winchester, KY 40391

  This little cutie sits at the end a cul-de-sac and backs to a farm. I'm not sure it gets much better! This 3 bedroom/2 full bath home is ready for you! The living room opens up into the eat-in kitchen boasting stainless steel appliances. The kitchen leads to the back deck that overlooks your fenced in backyard and views of the farm behind the house. 3 bedrooms and 2 full bathrooms round out this

  Devon Ramage The Brokerage

  246 Geronimo Ct, Winchester, KY 40391
• 

  

  /21

  $249,900

  • 3 Beds
  • 1 Bath
  • 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
• 

  

  /22

  $167,500

  • 3 Beds
  • 1 Bath
  • 1,274 Sq Ft

  146 Cook Ave, Winchester, KY 40391

  Sellers willing to pay towards closing cost! Welcome to 146 Cook Avenue in Winchester, Kentucky — an updated home combining classic charm with modern style. This 3-bedroom, 1-bath property offers around 1,274 sq. ft. of comfortable living space with an open-concept layout, newer flooring throughout, and a completely renovated kitchen. The tiled bathroom includes space for a washer and dryer, and

  Autumn Johannes National Real Estate

  146 Cook Ave, Winchester, KY 40391
• 

  

  /7

  $190,000

  • 3 Beds
  • 2 Baths
  • 1,116 Sq Ft

  41 7th St, Winchester, KY 40391

  Welcome to 41 7th Street! This all-brick ranch features 3 bedrooms, 2 full baths, and beautiful hardwood floors throughout the living room, hallway, and bedrooms. Tucked at the end of the street, the property offers added privacy and peaceful farm views behind the home. Enjoy newer windows, a new HVAC system, and a new water heater for added comfort and efficiency. The attached garage provides

  Austina Bruton Re/Max Elite Realty - Hamburg

  41 7th St, Winchester, KY 40391
• 

  

  /14

  $159,900

  • Land
  • 2.66 Acres
  • $60,113 per Acre

  590 Craig Crossing, Winchester, KY 40391

  Don't let this opportunity pass you by again. This prime lot in Thoroughbred Estates is back on the market due to Current owners change of plans. This lot is ready for your new home with a beautiful setting and located close to Winchester and Lexington in a new Luxury Subdivision. Watch the sun set each night from your rear deck or pool. Call today!!!

  Keith Wilson Coldwell Banker McMahan

  590 Craig Crossing, Winchester, KY 40391
• 

  

  /33

  $255,000

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

  357 Crescent Ave, Winchester, KY 40391

  Welcome to this charming 3-bedroom, 1.5-bath home situated on a lovely corner lot. Step inside to discover a well-maintained interior with a thoughtful layout that flows effortlessly from room to room. The cozy living area opens to the dining space. You'll also find two versatile flex spaces, each filled with natural light from large windows-perfect for a home office, playroom, or creative

  Samantha Gray National Real Estate

  357 Crescent Ave, Winchester, KY 40391
• 

  

  /13

  $245,000

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

  130 E Broadway St, Winchester, KY 40391

  Wonderful investment opportunity! Cash flowing triplex located in the heart of Winchester. One unit has just been renovated and is ready for a new tenant. The other two have longstanding tenants who pay every month. Great price for the rent potential!

  Andrew Jarvis Lifstyl Real Estate

  130 E Broadway St, Winchester, KY 40391
• 

  

  /27

  $72,500

  • 3 Beds
  • 2 Baths
  • 1,128 Sq Ft

  725 Berry Ct, Winchester, KY 40391

  Looking for affordable homeownership in Winchester, KY? This move-in ready 3-bedroom, 2-bath manufactured home offers modern living at an incredible value. Built just 3 years ago and meticulously maintained, this home feels like new from the moment you step inside. Located in the heart of Winchester, you'll enjoy easy access to local restaurants, shopping, grocery stores, parks, and everyday

  Christa Joynt Keller Williams Commonwealth

  725 Berry Ct, Winchester, KY 40391
• 

  

  /55

  $425,000

  • 5 Beds
  • 3.5 Baths
  • 2,564 Sq Ft

  6504 Combs Ferry Rd, Winchester, KY 40391

  Welcome to an extraordinary residence where luxury, craftsmanship, and natural beauty come together. This house has been taken down to the studs, and thoughtfully rebuilt. This two story home with a walk-out basement sits on 8 acres, adjoining the Lower Howard Creek Preserve, offering unmatched privacy and an exceptional standard of living. The owner spared no expense—every detail has been

  Lucy Martin Jenkins United Real Estate Bluegrass

  6504 Combs Ferry Rd, Winchester, KY 40391
• 

  

  /39

  $295,000

  • 3 Beds
  • 2 Baths
  • 1,979 Sq Ft

  8 Village Dr, Winchester, KY 40391

  Newly renovated 3 bedroom, 2 full bathroom home located close to downtown, shopping, and medical services as well as College Park which features a indoor pool, tennis, pickleball courts, and much more. Home features all new paint, flooring, updated bathrooms, updated appliances, new lighting, and much, much more. Basement has large Family Room with bar. This home is ready for all your family

  Keith Wilson Coldwell Banker McMahan

  8 Village Dr, Winchester, KY 40391
• 

  

  /65

  $489,000

  • 3 Beds
  • 2 Baths
  • 2,053 Sq Ft

  670 Lillies Ferry Rd, Winchester, KY 40391

  *MOTIVATED SELLERS* Escape to this serene and private 12+ acre property, boasting a 3BR/2BA home sitting on a partially finished walkout basement providing a versatile space for relaxation, recreation, or additional living quarters. This charming home has lots of recent upgrades, including a brand new HVAC system and energy-efficient windows, ensuring a comfortable and sustainable living

  Jennifer Helton EXP Realty, LLC

  670 Lillies Ferry Rd, Winchester, KY 40391
• 

  

  /18

  $115,000

  • 2 Beds
  • 1 Bath
  • 910 Sq Ft

  114 Magnolia St, Winchester, KY 40391

  Great opportunity for investors, flippers, or anyone looking for a project with tons of potential! This 2 bedroom, 1 bath home features a 2 year old roof, giving you a solid head start on future updates. With its convenient location and plenty of possibilities, this property is ready for someone to bring their vision! Selling as is. Cash or conventional financing only.

  Michelle Blackburn RE/MAX Creative, Winchester

  114 Magnolia St, Winchester, KY 40391
• 

  

  /5

  $29,000

  • Land
  • 0.46 Acre
  • $63,043 per Acre

  102 Augusta Dr, Winchester, KY 40391

  This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

  Dale Hatton Dream Maker Realty, LLC

  102 Augusta Dr, Winchester, KY 40391
• 

  

  /9

  $206,000

  • Land
  • 7.77 Acres
  • $26,512 per Acre

  368 Flanagan Station Rd, Winchester, KY 40391

  Build your dream retreat on this beautiful 7.77-acre parcel nestled in a peaceful rural setting just outside Winchester. The gently rolling terrain provides a serene backdrop for your custom home, hobby farm, or equestrian space, offering plenty of room to roam, garden, or simply enjoy the privacy. With easy access from Flanagan Station Road, this property combines a quiet country feel with

  Shari Frasure Keller Williams Commonwealth

  368 Flanagan Station Rd, Winchester, KY 40391
• 

  

  /5

  $70,000

  • Land
  • 1.72 Acres
  • $40,698 per Acre

  12541 Ironworks Rd, Winchester, KY 40391

  Discover the perfect place to build your dream home in Eskippakithiki Overlooks. This beautiful 1.72 acre parcel offers ample space, peaceful surroundings, and stunning natural views. Enjoy the serenity of country living, this land provides an ideal canvas for a custom home or family getaway. Don't miss this opportunity to secure your own piece of paradise.

  Daniela Virguez National Real Estate

  12541 Ironworks Rd, Winchester, KY 40391
• 

  

  /34

  $240,000

  • 3 Beds
  • 2 Baths

  12 Linden Ave, Winchester, KY 40391

  Cute ranch with easy access to I-64 and downtown Winchester. 3 bedrooms with 2 full baths with 1 car detached garage with fenced in back yard. This property has a interesting feature of a building that's 14 x 40 that has been a rental but can be used as storage or a mother in-law suite.

  Roni Porter RE/MAX Creative Realty

  12 Linden Ave, Winchester, KY 40391
• 

  /2

  $882,000

  • Land
  • 3.93 Acres
  • $224,427 per Acre

  Lot 1 - 12 Plantations Dr, Winchester, KY 40391

  NOW SELLING PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build your New

  Melia Hord Keller Williams Legacy Group

  Lot 1 - 12 Plantations Dr, Winchester, KY 40391
• 

  

  /29

  $268,000

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft

  410 Wellington Way, Winchester, KY 40391

  Discover 410 Wellington Way, a beautifully updated property in a convenient Winchester location! This fully updated, move-in-ready home delivers style, comfort, and convenience from the moment you walk in. Enjoy a bright eat-in kitchen equipped with brand-new, warrantied appliances, plus modern finishes throughout—including all-new paint, new flooring, new light fixtures, new doors, updated

  Monica Marcum Century 21 Pinnacle

  410 Wellington Way, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 0.22 Acre
  • $356,818 per Acre

  Lot 5 Plantations Dr, Winchester, KY 40391

  NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

  Melia Hord Keller Williams Legacy Group

  Lot 5 Plantations Dr, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 0.22 Acre
  • $356,818 per Acre

  Lot 3 Plantations Dr, Winchester, KY 40391

  NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

  Melia Hord Keller Williams Legacy Group

  Lot 3 Plantations Dr, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 0.22 Acre
  • $356,818 per Acre

  Lot 4 Plantations Dr, Winchester, KY 40391

  NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

  Melia Hord Keller Williams Legacy Group

  Lot 4 Plantations Dr, Winchester, KY 40391
• 

  

  /100

  $1,889,000

  • 3 Beds
  • 2.5 Baths
  • 4,518 Sq Ft

  3166 Colby Rd, Winchester, KY 40391

  Welcome to this beautiful 33± acre estate, offering the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, retains timeless character and can be registered with the Historical Home Society. Enjoy stunning mountain views — located at one of the highest points in Clark County, where you can see the dormitories at EKU in Richmond and

  Alyssa M Boley Coldwell Banker McMahan

  3166 Colby Rd, Winchester, KY 40391
• 

  

  /12

  $230,000

  • 2 Beds
  • 1 Bath
  • 1,484 Sq Ft

  605 College St, Winchester, KY 40391

  Brick ranch in the College Park neighborhood. Large living area and kitchen with updated appliances and mechanicals (water heater and heat pump). The previous owner water proofed the basement and a new garage door has been installed. Bonus room could be utilized as an additional living room or bedroom.

  Steve Adams Steven D Adams Real Estate Services, LLC

  605 College St, Winchester, KY 40391
• 

  

  /4

  $124,900

  • 4 Beds
  • 2.5 Baths
  • 2,131 Sq Ft

  205 E Washington St, Winchester, KY 40391

  PRICE DROP!!! FLIP This House! Seller Has Added A Large Primary Addition And Front Porch. This 4 Bedroom 2 1/1 Bath Home Is Ready For Your Finishes And Has A Fantastic Floor Plan With Large Loft (Whole Home At Stud Level). Finish This Home It Will Be A Showstopper Better Than New Construction With Large Sq Ft What Many Buyers Are Looking For. Great Opportunity To Make Money Or Live In This

  W Patrick Arvin Keller Williams Commonwealth

  205 E Washington St, Winchester, KY 40391
• 

  

  /27

  $269,000

  • 3 Beds
  • 2.5 Baths
  • 1,456 Sq Ft

  222 Bracken Ct, Winchester, KY 40391

  Great flloor plan -- great location -- GREAT price! Nice open space on the first level with fully-equipped kitchen and dining area and a very generously-sized family room. Backs up to Ecton Road so you are not looking at the back of another house. Primary bedroom and laundry upstairs with two other bedrooms. All three bedrooms have walk-in closets! The storage building conveys. This home is less

  Jim Woodrum RE/MAX Creative, Winchester

  222 Bracken Ct, Winchester, KY 40391
• 

  

  /6

  $200,000

  • Land
  • 0.81 Acre
  • $246,914 per Acre

  550 Bullion Blvd, Winchester, KY 40391

  Rarely available Bypass frontage lot for sale! Exciting opportunity to locate alongside a new Chipotle that is soon to be under construction. Retention in place, leaving approximately 1/2-acre developable. Perfect location for a national retailer. Ideally located along the heart of Bypass Road in Winchester, Kentucky between Kroger and Walmart shopping centers. Winchester, Kentucky is the county

  Greg Leveridge Block + Lot Real Estate

  550 Bullion Blvd, Winchester, KY 40391
• 

  

  /42

  $475,000

  • 5 Beds
  • 3 Baths
  • 3,718 Sq Ft

  1503 Schollsville Rd, Winchester, KY 40391

  Do you ever wonder what it would be like to live in the days of "Gone with the Wind"? Well, here is your chance to own your own personal "Tara". Spacious country home with acreage suitable for children, pets, and livestock. This home is perfect for escaping city life and crowds. Home consists of 5 bedrooms, 3 full bathrooms, Living Room, Dining Room, large Kitchen, room for an office or craft

  Keith Wilson Coldwell Banker McMahan

  1503 Schollsville Rd, Winchester, KY 40391
• 

  

  /64

  $420,000

  • 5 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  1857 Ironworks Rd, Winchester, KY 40391

  Get a piece of Bluegrass heaven in this move-in ready modern farmhouse on just under 5acres in Clark County. Dreaming of the country life? This is it, originally built in 1865 this timeless home has been completely updated and seamlessly blended the history with modern elegant design and livability. Classic farmhouse style with tons of natural light that bring the outside in. Spacious great room

  Meredith Walker Bluegrass Sotheby's International Realty

  1857 Ironworks Rd, Winchester, KY 40391
• 

  

  /15

  $600,000

  • 8 Beds
  • 4 Baths
  • 5,046 Sq Ft

  101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391

  Step into a rare investment opportunity in the heart of downtown Winchester! This beautifully renovated 4-plex offers charm, space, and convenience — all within a fully restored historic building. Each of the four spacious units boasts approximately 1,296 sq ft, blending timeless character with modern updates. The entire property has been thoughtfully renovated in 2021, including a brand-new

  Priya Patel-Rossetti Big Blue Realty

  101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391
• 

  

  /33

  $225,000

  • 4 Beds
  • 1 Bath
  • 1,743 Sq Ft

  218 E Washington St, Winchester, KY 40391

  Four Bedroom home in Winchester, Ky which includes a bonus room ready for a makeover for whatever you would like to make it. Enjoy a good sized backyard that is fenced in, along with a detached garage.

  Fernando Andrade Rector Hayden Realtors

  218 E Washington St, Winchester, KY 40391
• 

  

  /34

  $279,700

  • 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 open to a large dining area. 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

  Craig Bridgewater Bridgewater Real Estate

  404 Wellington Way, Winchester, KY 40391
• 

  

  /3

  $146,000

  • 3 Beds
  • 1 Bath
  • 1,020 Sq Ft

  228 Jackson St, Winchester, KY 40391

  Here's your chance to own a nice investment property. This single family home has a 3 bed 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  228 Jackson St, Winchester, KY 40391
• 

  

  /3

  $70,000

  • Land
  • 2.04 Acres
  • $34,314 per Acre

  150 Spencer Ln, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Or hold as investment property and let the land grow in value. This lot totaling 2.041 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

  Kathryn Cheuvront Coldwell Banker McMahan

  150 Spencer Ln, Winchester, KY 40391
• 

  

  /4

  $137,500

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

  12569 Ironworks Rd, 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 gows 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

  12569 Ironworks Rd, Winchester, KY 40391

Showing Results 41 - 80, Page 2 of 6