Homes for Sale in 40391

• 

  

  

  /30

  $310,000

  Open Sun 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 2,285 Sq Ft

  872 Stratton Ln, Winchester, KY 40391

  Welcome home to this well-maintained, one-owner split-level offering space, comfort, and endless possibilities! Featuring 4 bedrooms and 2 full baths, this home provides room for everyone. Enjoy both a spacious living room and cozy family room wih a fireplace, perfect for relaxing or entertaining. The functional floor plan offers flexibility for today's lifestyle. New carpet and fresh paint

  Kathryn Cheuvront Coldwell Banker McMahan

  872 Stratton Ln, Winchester, KY 40391
• 

  

  

  /39

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft

  13 Lakeview Dr, Winchester, KY 40391

  Seller has accepted an offer with a 48 hour kickout clause. Beautifully updated brick ranch with a partially finished basement offering 3 bedrooms and 2 full baths! The main level features a welcoming living room with a masonry gas log fireplace that opens into the updated kitchen complete with island bar seating, eat-in dining area, and access to the screened-in deck, perfect for relaxing or

  Michelle Blackburn RE/MAX Creative, Winchester

  13 Lakeview Dr, Winchester, KY 40391
• 

  

  

  /50

  $545,000

  665 Lillies Ferry Rd, Winchester, KY 40391

  You do not want to sleep on this one, it is a beautiful working farm with multiple building sites and amazing views and tranquility. Two farms are selling together for a total of 91.28 acres that is already a very productive cattle farm. The fencing, gates, waterers and infrastructure is already in place to move right in and produce income. There are multiple possible building sites with amazing

  Carrie Taylor Taylor Real Estate, LLC

  665 Lillies Ferry Rd, Winchester, KY 40391
• 

  

  

  /24

  $289,900

  • 4 Beds
  • 2 Baths
  • 1,752 Sq Ft

  198 Hilltop Dr, Winchester, KY 40391

  Excellent location! 4 bedroom, 2 bath. This home offers one level living on the edge of town and close to the interstate! AMAZING VIEWS of country side! Two living room spaces! Split bedroom design. Covered back patio. NEW LVP flooring. Freshly painted throughout. NEW appliances. Fully fenced backyard. This home is move in ready. Come see today!

  Stephanie Hacker Kentucky Residential Real Estate, LLC

  198 Hilltop Dr, Winchester, KY 40391
• 

  

  

  /9

  $155,000

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,097 Sq Ft

  220 E Washington St, Winchester, KY 40391

  Charming 3-Bedroom Home with Great Investment Potential....Welcome to this charming 3-bedroom, 1-bath home offering comfortable living space and plenty of opportunity for homeowners or investors alike. Featuring an easy layout with generously sized bedrooms, a large eat-in kitchen, and a bright living area, Outside, you'll find a covered front porch perfect for relaxing, along with a private

  Whitney Ensor Ensor Real Estate, LLC

  220 E Washington St, Winchester, KY 40391
• 

  

  /26

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  528 Estes Dr, Winchester, KY 40391

  This home is complete with an Aurora above ground pool for all the summer fun. The 3 beds 2 bath brick ranch home is located conveniently to shopping, dining, parks, pool and more. Large open family room and kitchen with wood bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. There is an oversized storage/tool shed, and a partially

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
• 

  

  /7

  $400,000

  • Land
  • 7.31 Acres
  • $54,720 per Acre

  4095 Basin Springs Rd, Winchester, KY 40391

  Looking for land to build your dream home that is private, but convenient? This 7+ acre beautiful lot is located in Clark County, just 15 minutes from Costco, Hamburg and I-75. No HOA or deed restrictions. The perfect place to build or have a small farm. Location! Location! Location!

  Peggy Baldridge HomeFirst Real Estate

  4095 Basin Springs Rd, Winchester, KY 40391
• 

  

  /60

  $249,900

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft

  17 Holiday Rd, Winchester, KY 40391

  This classic brick ranch house is move-in ready and waiting for you to call it home! Take a step inside the front door to appreciate the gleaming laminate wood floors in the open concept living space. Around the corner, the beautiful kitchen cabinets and updated, stainless, kitchen appliances are ready for family meals and social gatherings around the dining table. In the full bath, you'll find a

  Josh Wood Freedom Realty & Property Management

  17 Holiday Rd, Winchester, KY 40391
• 

  

  /20

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,210 Sq Ft

  122 Spruce Ct, Winchester, KY 40391

  Don't miss this move-in ready brick ranch home offering the perfect blend of comfort, style and convenience. Whether you're relaxing indoors or enjoying the outdoor space, this home is ready for its next owner to move right in and start making memories. Conveniently located near shopping, dining, schools, and major roadways, this updated ranch is a must-see. Don't miss your opportunity to own

  Peggy Baldridge HomeFirst Real Estate

  122 Spruce Ct, Winchester, KY 40391
• 

  

  /42

  $420,000

  • 3 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  19 Fontaine Blvd, Winchester, KY 40391

  Charming story and a half home nestled in a well established neighborhood, featuring beautiful hardwood floors and an updated kichen with modern finishes and ample cabinet space. Relax and entertain with ease on the screened back deck overlooking the large fenced backyard and enjoy the added bonus of a charming gazebo, perect for outdoor gathers or peaceful evenings. This well maintaned home

  Kathryn Cheuvront Coldwell Banker McMahan

  19 Fontaine Blvd, Winchester, KY 40391
• 

  

  /35

  $329,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft

  8 Monroe Ave, Winchester, KY 40391

  If you love to entertain and are looking for a cozy home that is move in ready, you don't want to let the one pass you by! Includes 3 bedrooms and two full baths this home has it all. Equipped with a primary bedroom suite with spacious bathroom and walk in closet. This home has beautiful hardwood floors in kitchen living and dining areas. In the gallery kitchen you will find granite countertops,

  Lisa Barker Freedom Realty & Property Management

  8 Monroe Ave, Winchester, KY 40391
• 

  

  /31

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft

  312 Buffalo Trace, Winchester, KY 40391

  Welcome home to this inviting 3 Bedroom 2 bath home situated on a spacious 0.41 Acre lot. This home offers the perfect blend of comfort and functionality that offers a well designed layout with ample living space. Step into the spacious living room where beautiful Hardwood floors add warmth, character,and timeless appeal. Perfect for relaxing with family or entertaining guests. The Master bedroom

  Paula Cole The Agency

  312 Buffalo Trace, Winchester, KY 40391
• 

  

  /62

  $329,900

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  335 Newcastle Ln, Winchester, KY 40391

  Welcome to this well-maintained home located in a quiet, established neighborhood with convenient access to everything Winchester has to offer. The first floor features an open and inviting layout, creating a comfortable space for everyday living and entertaining alike. Upstairs, you'll find a traditional three-bedroom floor plan with generously sized bedrooms, including a spacious primary suite.

  Josh Wood Freedom Realty & Property Management

  335 Newcastle Ln, Winchester, KY 40391
• 

  

  /5

  $29,000

  $4K PRICE DROP

  • Land
  • 20,037 Sq Ft
  • $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
• 

  

  /65

  $759,000

  $66K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 2,361 Sq Ft

  455 Davis Ln, Winchester, KY 40391

  Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of

  Dale Hatton Dream Maker Realty, LLC

  455 Davis Ln, Winchester, KY 40391
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  /60

  $225,000

  $74K PRICE DROP

  • 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
• 

  

  /33

  $289,000

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

  214 S Burns Ave, Winchester, KY 40391

  Step into the timeless charm of this beautifully maintained historic home featuring 4 bedrooms, 1.5 baths, a formal dining room, living room, laundry room, and charming library with built-in bookshelves and pocket doors. Original heart pine floors, soaring ceilings, a winding staircase, and five decorative fireplaces showcase the home's historic craftsmanship, while updates provide modern

  Lindsay Heeger eXp Realty LLC

  214 S Burns Ave, Winchester, KY 40391
• 

  

  /27

  $152,500

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft

  65 Fitch Ave, Winchester, KY 40391

  Lovely older home, located witin waking distance to collage park whice offers Pickle Ball, Pool, Tennis, play gound and Walking Trail, also walking distance to Historic Downtown Winchester, with a little love house brings large rooms and a nostlogic atmosphire, take a look, view today, this a a great price for 3 bedrooms, 1 1/2 baths, nice back yard, with parking, call today! Selling "AS IS",

  Mila Ensor Ensor Real Estate, LLC

  65 Fitch Ave, Winchester, KY 40391
• 

  

  /49

  $464,000

  $5K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,296 Sq Ft

  105 Monet Blvd, Winchester, KY 40391

  Welcome to 105 Monet Blvd., located in one of Winchester's most desirable neighborhoods! This beautifully updated home offers the perfect combination of space, style, and future potential. Featuring 4 spacious bedrooms, a dedicated home office, formal dining room, family room, and an eat-in kitchen, this home was designed for both comfortable living and entertaining. The newly remodeled kitchen

  Kristey Wood eXp Realty, LLC

  105 Monet Blvd, Winchester, KY 40391
• 

  

  /14

  $650,000

  • Land
  • 3 Acres
  • $216,667 per Acre

  205 Codella Dr, Winchester, KY 40391

  Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Homes

  205 Codella Dr, Winchester, KY 40391
• 

  

  /13

  $400,000

  • Land
  • 2.19 Acres
  • $182,648 per Acre

  145 Codella Dr, Winchester, KY 40391

  Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Homes

  145 Codella Dr, Winchester, KY 40391
• 

  

  /30

  $385,000

  • 3 Beds
  • 2.5 Baths
  • 1,945 Sq Ft

  309 Gallahadion Ct, Winchester, KY 40391

  Built in 2024 and upgraded throughout, this beautiful 3-bedroom, 2.5-bath home offers modern style, functional living space, and a prime location just moments from Winchester Country Club. The open-concept main level features a spacious living room, kitchen, and dining area designed for both everyday living and entertaining, complete with granite countertops in the kitchen and baths, a deep

  Michelle Blackburn RE/MAX Creative, Winchester

  309 Gallahadion Ct, Winchester, KY 40391
• 

  

  /73

  $1,349,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,350 Sq Ft

  1200 Craig Crossing, Winchester, KY 40391

  Discover elevated living on 2.5 acres! This 3,350 sqft custom masterpiece boasts 4 bedrooms, 4.5 bathrooms with an open 2,670 sqft main level. Featuring custom solid oak cabinetry not only in kitchen, but master closets, pantry and utility areas. Custom Showers and tile in each bathroom throughout the home. Gas and electric fireplaces located in great room as well as primary first floor bedroom.

  Michael Hilario The Agency

  1200 Craig Crossing, Winchester, KY 40391
• 

  

  /22

  $229,500

  • 2 Beds
  • 1 Bath
  • 1,454 Sq Ft

  2 Western Ave, Winchester, KY 40391

  Don't miss this wonderful home offering convenience, comfort, and value!! Ideally situated near shopping, dining, schools, churches and everyday amenities. This property is perfect for first-time buyers or downsizers. The backyard provides ample space for entertaining is completely fenced in for children and pets. Home also provides room to grow. The attic space has plenty of room to add another

  A. Rebecca Woods Woods Realty Group

  2 Western Ave, Winchester, KY 40391
• 

  

  /21

  $265,000

  • 3 Beds
  • 1 Bath
  • 1,324 Sq Ft

  119 Sunset Heights, Winchester, KY 40391

  Come Home to Sunset!!!! Brick Ranch home, with 2 driveways, 3 bedrooms, 1 bathroom, Open Living Room, Dining Room and Kitchen Area, Spacious Laundry Room, Covered back patio for outdoor living! Beautiful Hardwood floors, updated bathroom and kitchen, exceptional location, building out back for he shed or she shed or storage, move in and enjoy the sunset!

  Whitney Ensor Ensor Real Estate, LLC

  119 Sunset Heights, Winchester, KY 40391
• 

  

  /55

  $558,900

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft

  108 Bella Shae Way, Winchester, KY 40391

  Nearly new French country ranch that has been gently lived in. This classy home has magnificent curb appeal. When you walk through the front door you are welcomed by a tasteful foyer area. Stroll into the wide-open space of the great room with a towering, coffered ceiling and tons of natural light. The gas fireplace adds a nice focal point to the living space. The kitchen space is equipped with

  Vickie Skeens RE/MAX Elite Lexington

  108 Bella Shae Way, Winchester, KY 40391
• 

  

  /46

  $247,000

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  30 Virginia Ave, Winchester, KY 40391

  Welcome to a well maintained 3 bedroom 1 full bath home that has been lovingly cared for by only two owners since 1962. Recent updates include new flooring and completed repairs, makiing this property ready for a new owner, while preserving its timeless character. Beautiful hardwood floors add warmth and charm throughout the home. Enjoy relaxing or entertaining on the comfortable spacious patio

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 719-2057

  30 Virginia Ave, Winchester, KY 40391
• 

  

  /49

  $254,500

  • 3 Beds
  • 1.5 Baths
  • 1,533 Sq Ft

  377 Crescent Ave, Winchester, KY 40391

  Don't miss out on this beautiful two-story, 3 BR, 1.5 BA home in a great neighborhood in the heart of Winchester! Great-sized living room with real hardwood floors, complete with a tiled fireplace with mantel (seller has never used). Spacious Kitchen with a tiled backsplash, white cabinets, and stainless-steel appliances! Large Dining Room that will accommodate nearly any size table. Half bath

  Bill VanWinkle Joyce Marcum Realty

  377 Crescent Ave, Winchester, KY 40391
• 

  

  /36

  $549,900

  • 4 Beds
  • 5 Baths
  • 4,173 Sq Ft

  600 Boone Ave, Winchester, KY 40391

  Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the

  Holly Goeing The Agency

  600 Boone Ave, Winchester, KY 40391
• 

  

  /5

  $154,900

  • Land
  • 2.53 Acres
  • $61,250 per Acre

  750 Craig Crossing Unit Lot 7, Winchester, KY 40391

  Great opportunity to own a prime lot in the exclusive Thoroughbred Estates, Winchester's most exclusive subdivision. Located between Winchester and Lexington this location is close to shopping, schools, hospitals and interstates. If your tired of living on a postage stamp lot then this lot is for you. Select your dream house plan and select your builder before it's too late.

  Keith Wilson Coldwell Banker McMahan

  750 Craig Crossing Unit Lot 7, Winchester, KY 40391
• 

  

  /20

  $354,900

  New Construction Open Sun 2PM - 4PM $14K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,266 Sq Ft

  107 Gibson Way, Winchester, KY 40391

  A beautiful designed spacious house that offers 3 bedrooms, 3 full bathrooms, and 2266 sq ft og thoughtfully designed living space. Step inside to discover an open-concept layout perfect for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into the main living areas, creating a warm and inviting atmosphere. Generously sized bedrooms provide comfort and privacy,

  Vanessa Highland Stewart & Co Realty LLC

  107 Gibson Way, Winchester, KY 40391
• 

  

  /16

  $124,500

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 876 Sq Ft

  122 Calloway St, Winchester, KY 40391

  Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless

  Darrell Tackett Dream Maker Realty, LLC

  122 Calloway St, Winchester, KY 40391
• 

  

  /46

  $949,000

  • 3 Beds
  • 3 Baths
  • 2,200 Sq Ft

  330 Spencer Ln, Winchester, KY 40391

  MIDNIGHT ON THREE - Luxury Living Meets Convenience in Clark County KY Nestled on 3.054 beautifully maintained acres, this stunning home was thoughtfully designed with quality and elegance in every detail. Just 2 minutes from Exit 10 on the Mountain Parkway, this extraordinary custom-built estate offers a rare combination of privacy, craftsmanship, and accessibility. From the moment you arrive,

  Jodie Brandenburg Red River Gorge Real Estate

  330 Spencer Ln, Winchester, KY 40391
• 

  

  /35

  $274,900

  • 2 Beds
  • 1 Bath
  • 849 Sq Ft

  955 Right Angle Rd, Winchester, KY 40391

  Newly renovated Cabin sitting on +- 5 acres. Renovations began in 2024 and were completed in 2026. An ideal property for a first-time home buyer or anyone looking for a remote quiet location located within 20 minutes of downtown Winchester.

  Rhett Hughes WTC Realty LLC

  955 Right Angle Rd, Winchester, KY 40391
• 

  

  /10

  $550,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  107 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

  Shane Underwood Keller Williams Commonwealth

  107 Bella Shae Way, Winchester, KY 40391
• 

  

  /22

  $665,000

  New Construction

  • 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
• 

  

  /9

  $785,000

  New Construction

  • 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
• 

  

  /3

  $670,000

  New Construction

  • 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
• 

  

  /4

  $625,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,405 Sq Ft

  424 Alexis Way, Winchester, KY 40391

  Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard Cove neighborhood. This exquisite floor plan features a side-turned garage and captivating curb appeal with double front entry doors. Inside, you'll find a thoughtfully designed split-bedroom layout with a spacious primary suite that includes a luxurious ensuite with a walk-in closet, double vanity, tile

  Shane Underwood Keller Williams Commonwealth

  424 Alexis Way, Winchester, KY 40391
• 

  

  /3

  $825,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,995 Sq Ft

  111 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. Thespacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a

  Shane Underwood Keller Williams Commonwealth

  111 Bella Shae Way, Winchester, KY 40391

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