Newest Homes for Sale in Winchester, KY

• 

  

  

  /33

  $465,000

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

  287 Logan Lick Rd, Winchester, KY 40391

  This 3 bedroom 2 bath ranch home is tucked away in a beautiful wooded area of Clark County. It is sitting on over 10 acres of land that would be great for livestock or hunting. It is just minutes from historic downtown Winchester. The property is also a short drive to retail shops, restaurants, and other amenities. Come take a look at the beautiful view from the front porch of this home in the

  Dale Hatton Dream Maker Realty, LLC

  287 Logan Lick Rd, Winchester, KY 40391
• 

  

  

  /24

  $299,900

  • 3 Beds
  • 2.5 Baths
  • 2,260 Sq Ft

  209 Boone Ave, Winchester, KY 40391

  Space, updates, and charm all come together in this spacious 2,260 square foot 1.5-story home located in the heart of Winchester! Recently updated and full of character, this property offers a flexible layout with room for everyone. The main level offers a welcoming living room, large family room, dining area, kitchen, laundry room, full guest bath, and a spacious primary suite complete with a

  Todd Hyatt Lois Ann Disponett Real Est

  209 Boone Ave, Winchester, KY 40391
• 

  

  

  /18

  $260,000

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  280 Pine Ridge Rd, Winchester, KY 40391

  Bring your vision to life on 12+ beautiful acres in Winchester! This 3-bedroom, 1-bath home offers the charm of a 1964 build and the opportunity to create your own private retreat. With plenty of room for gardens, animals, workshops, or expansion, this property is perfect for those dreaming of country living. Renovate the existing home or reimagine the space to fit your needs — the possibilities

  Derek Blankenship Keller Williams Commonwealth

  280 Pine Ridge Rd, Winchester, KY 40391
• 

  

  

  /50

  $245,000

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,042 Sq Ft

  217 Short St, Winchester, KY 40391

  This charming ranch home in a desirable neighborhood offers the perfect opportunity for first-time buyers, downsizers, or anyone looking for a move-in ready home with simple, comfortable living. Featuring 3 bedrooms and 1 full bath, this home includes plank flooring, fresh paint updates, updated kitchen appliances, and a functional layout designed for everyday convenience. The extended carport

  Josh Wood Freedom Realty & Property Management

  217 Short St, Winchester, KY 40391
• 

  

  

  /38

  $299,900

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

  147 Sunset Heights, Winchester, KY 40391

  This charming 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and potential! On a large corner lot in a cute, established neighborhood, this property features a spacious detached garage ideal for storage, hobbies, or workshop space. Inside, you'll find a functional layout with plenty of natural light and room to make it your own. The large partially unfinished basement provides

  Lyndsey Martin Kentucky Land and Home

  147 Sunset Heights, Winchester, KY 40391
• 

  

  /9

  $199,500

  $11K PRICE DROP

  • Land
  • 7.77 Acres
  • $25,676 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
• 

  

  /14

  $269,900

  • 3 Beds
  • 1 Bath
  • 1,644 Sq Ft

  205 Providence Ln, Winchester, KY 40391

  You Wont Find A More Beautiful And Private Setting!!! This Home Features 3 Bedrooms And 1 Bath And Sits On 5.05 Acres; Two Front Porches; Large Rear Porch; A Separate Room Downstairs That Would Make A Great Master Bedroom/Suite Potentially; Huge Mudroom/Flex Space! Possibilities Are Endless With This Property. This Home Has Replacement Vinyl Clad Windows, Roof And HVAC All Replaced In Last 10

  Patrick Arvin Keller Williams Commonwealth

  205 Providence Ln, Winchester, KY 40391
• 

  

  /10

  $575,000

  $75K PRICE DROP

  • Land
  • 2.6 Acres
  • $221,154 per Acre

  529 Bullion Blvd Unit 3B, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

  Greg Leveridge Block + Lot Homes

  529 Bullion Blvd Unit 3B, Winchester, KY 40391
• 

  

  /9

  $1,350,000

  $350K PRICE INCREASE

  • Land
  • 3.02 Acres
  • $447,020 per Acre

  155 April Way, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

  Greg Leveridge Block + Lot Homes

  155 April Way, Winchester, KY 40391
• 

  

  /10

  $550,000

  $100K PRICE DROP

  • Land
  • 3 Acres
  • $183,333 per Acre

  609 Bullion Blvd Unit 3A, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

  Greg Leveridge Block + Lot Homes

  609 Bullion Blvd Unit 3A, Winchester, KY 40391
• 

  

  /118

  $665,000

  Open Sun 2PM - 4PM $10K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,765 Sq Ft

  5865 Van Meter Rd, Winchester, KY 40391

  Experience the perfect balance of peaceful country living and modern comfort at 5865 Van Meter Road. Situated on 5.05 scenic acres with breathtaking farmland views, this spacious ranch-style home offers more than 2,700 square feet of thoughtfully designed living space with privacy, versatility, and charm throughout. A brand-new roof installed in May 2026 adds even more value and peace of mind.

  Laura Hayes Carpenter Keller Williams Commonwealth

  5865 Van Meter Rd, Winchester, KY 40391
• 

  

  /59

  $499,900

  • 4 Beds
  • 3 Baths
  • 5,646 Sq Ft

  16 Manor Dr, Winchester, KY 40391

  One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home!

  Zella Rosenthal Tom Goebel & Company

  16 Manor Dr, 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
• 

  

  /42

  $360,000

  • 4 Beds
  • 5 Baths
  • 4,798 Sq Ft

  502 W Lexington Ave, Winchester, KY 40391

  Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, high visibility commercial space with Lexington Avenue frontage and two apartments on the upper level! Each apartment has two bedrooms, one bath. One unit has been recently remodeled, the other has potential for value add. The flexible commercial space contains 3 half baths. Laundry hook-ups in all 3 units!

  Jason Townsend Kentucky Residential Real Estate, LLC

  502 W Lexington Ave, Winchester, KY 40391
• 

  

  /55

  $359,900

  • 3 Beds
  • 2 Baths
  • 2,835 Sq Ft

  27 Hampton Ave, Winchester, KY 40391

  Located on desirable Hampton Avenue, this all-brick ranch is full of timeless character and thoughtful updates. Beautiful original hardwood floors run throughout the main level, highlighted by detailed craftsmanship and charm you don't find every day. The spacious living room features built-ins, a fireplace, and flows into the dining area, creating a warm and inviting space for everyday living or

  Terra Long Keller Williams Commonwealth

  27 Hampton Ave, Winchester, KY 40391
• 

  

  /8

  $1,500,000

  1015 Old Stone Church Rd, Winchester, KY 40391

  Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights

  Walker Mack Bluegrass Property Exchange

  1015 Old Stone Church Rd, Winchester, KY 40391
• 

  

  /47

  $427,000

  • 3 Beds
  • 2.5 Baths
  • 2,289 Sq Ft

  20 Edgewood Dr, Winchester, KY 40391

  Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a

  Libby VanMeter Marshall Lane Real Estate - Lexington

  20 Edgewood Dr, Winchester, KY 40391
• 

  

  /44

  $349,500

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft

  221 W Hickman St, Winchester, KY 40391

  Step into a home where history and beauty meet in the most charming way. This stunning, fully remodeled historic home offers over 2600 square feet of thoughtfully renewed living space, blending timeless character with elegant modern updates. From the moment you walk inside, you'll feel the warmth and romance of a home that has been lovingly restored while still honoring its original charm. Large,

  Brandon Hedinger Keller Williams Bluegrass Realty

  221 W Hickman St, Winchester, KY 40391
• 

  

  /47

  $445,500

  • 3 Beds
  • 2.5 Baths
  • 2,961 Sq Ft

  42 Mockingbird Valley Rd, Winchester, KY 40391

  This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons

  Markus Cross McCallie Real Estate

  42 Mockingbird Valley Rd, Winchester, KY 40391
• 

  

  /43

  $319,900

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft

  3622 Stamper Dr, Winchester, KY 40391

  This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. With recently installed vinyl siding, gutters and gutter guard properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming

  Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
• 

  

  /31

  $350,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,310 Sq Ft

  38 N Burns Ave, Winchester, KY 40391

  Welcome to this beautiful new home in downtown Winchester! The open-concept design flows into a gorgeous kitchen w/granite countertops, gas stove, stainless appliances, and lots of cabinets. A first-floor bedroom w/private bath offers convenience flexibility. Upstairs, you'll find three generously sized bedrooms, each w/large closets, plus motion-activated hallway lighting. A covered back porch

  Trina Penn RE/MAX Creative Realty

  38 N Burns Ave, Winchester, KY 40391
• 

  

  /63

  $1,149,000

  $30K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,672 Sq Ft

  2100 Irvine Rd Unit 40391, Winchester, KY 40391

  Seller will need 48 Hours to show, This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths,

  Mila Ensor Ensor Real Estate, LLC

  2100 Irvine Rd Unit 40391, Winchester, KY 40391
• 

  

  /19

  $162,900

  • 2 Beds
  • 1 Bath
  • 842 Sq Ft

  22 Magnolia St, Winchester, KY 40391

  Adorable & inviting from the moment you arrive! This charming 2-bedroom, 1-bath home welcomes you with a cozy front porch perfect for relaxing evenings. Step inside to a comfortable living room, along with the kitchen with a dedicated dining space—ideal for everyday living or entertaining. Out back, you'll find a spacious yard ready to enjoy, complete with a fire pit for those crisp fall nights

  Sabrina Tucker RE/MAX Creative Realty

  22 Magnolia St, Winchester, KY 40391
• 

  

  /68

  $2,750,000

  • 8 Beds
  • 7.5 Baths
  • 13,433 Sq Ft

  4664 Lexington Rd, Winchester, KY 40391

  Welcome to 4664 Lexington Road—a magnificent private estate on 35 rolling acres of pristine Kentucky countryside that feels worlds away, yet sits just minutes from the charm of Winchester and the vibrancy of Lexington. A stately stone entry welcomes you down a graceful, winding driveway to a sweeping circular drive, leading to a grand 13,000+ square-foot residence built in 1997 with timeless

  Adam Boardman Block + Lot Homes

  4664 Lexington Rd, Winchester, KY 40391
• 

  

  /92

  $849,900

  • 3 Beds
  • 3 Baths
  • 3,336 Sq Ft

  6356 Van Meter Rd, Winchester, KY 40391

  Nestled in the peaceful countryside of Winchester, this charming property on Van Meter Road offers the perfect blend of privacy, comfort, access and room to roam. Set on 13.74 beautiful, fenced acres and located within minutes of I-64, I-75 and the Mountain Parkway, this unique property offers easy access to Lexington, Winchester, Paris, and all of Central Kentucky. Enjoy wide-open spaces, scenic

  Josh Wood Freedom Realty & Property Management

  6356 Van Meter Rd, Winchester, KY 40391
• 

  

  /31

  $249,900

  $6K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,446 Sq Ft

  123 Sunset Heights, Winchester, KY 40391

  You will love the atmosphere of this remodeled 3 bedroom, 2 bath home located in a secluded location. The large privacy fenced back yard is perfect for the children or pets. Renovated kitchen includes granite countertops, new range, dishwasher , and refrigerator. Home has a full partially finished walk out basement. You will love the large outbuilding as well as storage closet off of carport.

  Keith Wilson Coldwell Banker McMahan

  123 Sunset Heights, Winchester, KY 40391
• 

  

  /55

  $525,000

  • 3 Beds
  • 2 Baths
  • 2,563 Sq Ft

  935 Stoner-Ephesus Rd, Winchester, KY 40391

  Picture this: over five acres of Kentucky countryside, a handsome ranch-style home, and enough elbow room to finally breathe. This stunning 2,563 square foot retreat delivers the rare combination of refined interior finishes and genuine rural charm, all without sacrificing modern convenience. Inside, discover a generous family room anchored by a striking stone fireplace — the kind of space that

  Timothy Saylor Threshold Real Estate Services

  935 Stoner-Ephesus Rd, Winchester, KY 40391
• 

  

  /38

  $289,900

  $7K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,116 Sq Ft

  618 Westmeade Dr, Winchester, KY 40391

  PRICE IMPROVEMENT + $3,000 BUYER CREDIT! Motivated seller has adjusted the price to $289,900 and are offering a $3,000 credit at closing to use toward your personal updates, closing costs, or an interest rate buy-down! Conveniently located, this charming well kept home features a functional floorplan offering space that can be tailored for those who love to entertain or the growing family. On the

  Kristi Donaldson United Real Estate Bluegrass

  618 Westmeade Dr, Winchester, KY 40391
• 

  

  /12

  $199,900

  $30K PRICE DROP

  • 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
• 

  

  /52

  $334,900

  $5K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft

  228 Holiday Rd, Winchester, KY 40391

  Back on the market at no fault of the sellers. Don't miss your chance to own this beautifully updated split-level home in Holiday Hills! Featuring 4 bedrooms and 2 full baths, this home offers a bright, open-concept kitchen and living area perfect for both everyday living and entertaining. Thoughtfully updated in recent years, the home features newer flooring, fresh paint, updated cabinets and

  Caroline Mucci CENTURY 21 Commonwealth R E

  228 Holiday Rd, Winchester, KY 40391
• 

  

  /19

  $209,000

  • Land
  • 41.69 Acres
  • $5,014 per Acre

  2697 Pine Ridge Rd, Winchester, KY 40391

  Escape to your own private retreat with this stunning 41.6± acre wooded tract nestled in the scenic countryside of Winchester, Kentucky. This expansive property offers a rare opportunity to own a secluded slice of nature, perfect for a private estate, recreational getaway, or hunting retreat. With rich with mature timber, this land presents a lot of natural beauty. A network of cleared trails and

  Derek Blankenship Keller Williams Commonwealth

  2697 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /40

  $289,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,692 Sq Ft

  54 Locust Dr, Winchester, KY 40391

  Opportunity awaits at 54 Locust Drive in Wesleyan Park subdivision. This all-brick ranch on a full unfinished basement offers 3 bedrooms, 2 baths, and 1,692 square feet of finished living space, along with an equally spacious basement ready for storage, hobbies, or future possibilities. Built in 1960, this home features hardwood flooring, a 2-car attached garage, and a fenced backyard with a

  Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  54 Locust Dr, Winchester, KY 40391
• 

  

  /13

  $1,115,000

  • Land
  • 120 Acres
  • $9,292 per Acre

  345 Providence Ln, Winchester, KY 40391

  Possible option to purchase the full 202 acres! Rare opportunity to own approximately 120 acres of beautiful rolling farmland in Clark County! This versatile property offers a mix of cleared pasture and wooded acreage, ideal for cattle, horses, recreation, or your dream homestead. Including a large pond plus county water available at the road this property is well-suited for agricultural use. The

  Megan McCoy Keller Williams Legacy Group

  345 Providence Ln, Winchester, KY 40391
• 

  

  /23

  $199,900

  $40K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,444 Sq Ft

  148 W Lexington Ave, Winchester, KY 40391

  Located in the heart of Winchester, this spacious and versatile two-story home offers incredible potential for both homeowners and savvy investors alike. With a total of 5 BR- this property provides ample space to accommodate a variety of living arrangements, from a large single-family home to a high -demand rental opportunity. The home features a welcoming covered front porch, perfect for

  Alyssa M Boley Coldwell Banker McMahan

  148 W Lexington Ave, Winchester, KY 40391
• 

  

  /60

  $395,000

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,310 Sq Ft

  382 S Main St, Winchester, KY 40391

  Spacious and full of character, this unique 4 bedroom, 3 bath home sits on a corner lot on South Main right across from the iconic South Main Grocery. Inside, you are welcomed by a two story foyer and a layout that offers flexibility with a living room, main level bedroom, full bath, and a dining room that could also function as an office with double doors. The kitchen has space for eat in dining

  Michelle Blackburn RE/MAX Creative, Winchester

  382 S Main St, Winchester, KY 40391
• 

  

  /33

  $289,999

  $40K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,648 Sq Ft

  414 Pueblo Ct, Winchester, KY 40391

  PRICE DROP and a MOTIVATED SELLER!! Currently priced below 2026 Clark County Department of Revenue Property Assessment valuation. Turn-key, dialed-in, and ready to impress! This Craftsman-style stunner delivers the space, flow, and finishes today's buyers are chasing. With 3 oversized bedrooms, 2.5 baths, and a fully finished walk-out basement, this home lives large and shows even better. The

  Walker Sabourin The Local Agents

  414 Pueblo Ct, Winchester, KY 40391
• 

  

  /51

  $69,900

  • Land
  • 4.48 Acres
  • $15,603 per Acre

  1450 Ford Rd, Winchester, KY 40391

  Darrell Tackett Dream Maker Realty, LLC

  1450 Ford Rd, Winchester, KY 40391
• 

  

  /21

  $139,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft

  9 Linden Ave, Winchester, KY 40391

  Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval,

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
• 

  

  /20

  $312,000

  $95K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,858 Sq Ft

  200 Dubuy Dr, Winchester, KY 40391

  Search no more your dream home just hit the market! You will fall in love with this one as soon as you walk through the front door. Beautiful open concept, very modern new home just built in 2022. You're going to love the open kitchen and living room area with the large kitchen island, beautiful stainless steel appliances and granite countertops. Primary bedroom on the first floor with a full

  Wayne Elkins RE/MAX Creative Realty

  200 Dubuy Dr, Winchester, KY 40391
• 

  

  /30

  $312,000

  $11K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,648 Sq Ft

  412 Pueblo Ct, Winchester, KY 40391

  Welcome to this beautifully maintained 5-year-old home nestled on a quiet cul-de-sac in the desirable Ft. Estill area of Winchester. This charming property offers 3 bedrooms and 2.5 baths, a spacious and functional layout with comfortable living areas perfect for both everyday living and entertaining. Enjoy low-maintenance flooring throughout all the main living areas and plenty of natural light

  Lisa Dickens Rector Hayden Realtors

  412 Pueblo Ct, Winchester, KY 40391

Showing Results 41 - 80, Page 2 of 6