Newest Homes for Sale in Winchester, KY

• 

  

  

  /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
• Explore Winchester

• 

  

  

  /31

  $189,000

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  5434 Pine Ridge Rd, Winchester, KY 40391

  Jim Woodrum RE/MAX Creative, Winchester

  5434 Pine Ridge Rd, 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 Open Sat 2PM - 4PM

  • 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
• 

  

  

  /59

  $274,900

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft

  403 Pueblo Ct, Winchester, KY 40391

  Built in 2020, this well-maintained Craftsman-style ranch offers the benefits of newer construction without the wait or added cost. Located in Winchester, KY, this home combines comfort, functionality, and convenience in one clean package. Featuring 3 bedrooms and 2 full baths, the layout is designed for everyday living with an open feel and thoughtful flow throughout. The kitchen includes

  Josh Wood Freedom Realty & Property Management

  403 Pueblo Ct, Winchester, KY 40391
• 

  

  /21

  $200,000

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft

  265 Cunningham Ln, Winchester, KY 40391

  There's nothing sweeter than countryside views! 30 Minutes to Hamburg in Lexington & USDA eligible at 0% down! Located off the Mountain Parkway & Ironworks Rd, this property features over an acre of land, a fenced-in backyard, and a new septic tank system. Well maintained and only 2 years old, this home is the perfect opportunity to start your mini farm. (3rd bedroom not photographed, being used

  Kierstin Shaffer Berkshire Hathaway HomeServices Foster Realtors

  265 Cunningham Ln, Winchester, KY 40391
• 

  

  /21

  $240,000

  • 3 Beds
  • 2 Baths
  • 1,244 Sq Ft

  407 Pueblo Ct, Winchester, KY 40391

  Welcome to 407 Pueblo Court! This well-kept 3 bed, 2 bath home sits on a quiet cul-de-sac and offers easy one-level living in a convenient Winchester location. Inside, you'll find a functional layout, great natural light, and comfortable living spaces that feel like home. The spacious backyard gives you plenty of room to relax, entertain, or enjoy time with family and friends. Whether you're a

  Joseph Miller Keller Williams Legacy Group

  407 Pueblo Ct, 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 3,400 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.

  Brandon Hedinger Keller Williams Bluegrass Realty

  221 W Hickman St, Winchester, KY 40391
• 

  

  /20

  $130,000

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  103 Yorktowne Ct, Winchester, KY 40391

  Affordable and move in ready! This home will qualify for FHA, VA &/or Rural Housing Loan. This charming 3 bedroom, 1 bath home offers the perfect opportunity for first-time buyers, down-sizers, or investors. With a welcoming layout, comfortable living spaces, and a great location in Winchester, this property is an excellent value in today's market. Enjoy the convenience of nearby shopping,

  Susy Esquivel Allied Realty

  103 Yorktowne Ct, 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
• 

  

  /22

  $230,000

  • 4 Beds
  • 2 Baths
  • 2,106 Sq Ft

  108 Spruce Ct, Winchester, KY 40391

  Charming home located on a quiet cul-de-sac in Winchester. This 4-bedroom, 2-bath home offers great potential for homeowners and investors alike. Featuring a functional layout and spacious yard, this property is ready for your personal touch. The kitchen includes a stainless steel refrigerator, with an additional refrigerator located in the basement. Enjoy a bar area in the basement, perfect for

  Tierra Newkirk Keller Williams Commonwealth

  108 Spruce Ct, Winchester, KY 40391
• 

  

  /33

  $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
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  /63

  $1,149,000

  • 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
• 

  

  /38

  $329,900

  • 4 Beds
  • 1 Bath
  • 2,327 Sq Ft

  162 French Ave, Winchester, KY 40391

  Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready

  Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  162 French Ave, 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
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  /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 Real Estate

  4664 Lexington Rd, Winchester, KY 40391
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  /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

  $255,900

  • 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

  $296,900

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

  618 Westmeade Dr, Winchester, KY 40391

  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 main level you'll find the living room, an eat in kitchen, 3 bedrooms and a full bathroom. Off of the kitchen is a large deck that's perfect for get togethers with family or friends. Downstairs has a second living

  Kristi Donaldson United Real Estate Bluegrass

  618 Westmeade Dr, Winchester, KY 40391
• 

  

  /25

  $270,000

  • 3 Beds
  • 2 Baths
  • 1,190 Sq Ft

  164 Buckingham Ln, Winchester, KY 40391

  Welcome home to easy, one-level living in this inviting 3-bedroom, 2-bath ranch! From the moment you step inside, the foyer opens to a spacious living room with a vaulted ceiling, creating a bright and open feel. The desirable split-bedroom layout offers privacy, with the primary suite tucked away on one side of the home featuring a large walk-in closet and full bath. Two additional bedrooms and

  Heather Baber Rector Hayden Realtors

  164 Buckingham Ln, Winchester, KY 40391
• 

  

  /12

  $199,900

  • 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

  $339,900

  • 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

  $299,000

  • 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
• 

  

  /57

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,779 Sq Ft

  720 Terry Dr, Winchester, KY 40391

  Welcome home to this beautifully refreshed 3-bedroom, 2-bath property located in the heart of Winchester, KY, just minutes from the Winchester Bypass for quick and easy commuting. Priced at $275,000, this home offers exceptional value in a highly walkable and convenient neighborhood. Step inside to find a freshly painted interior that feels bright, clean, and move-in ready. The thoughtful layout

  Christa Joynt Keller Williams Commonwealth

  720 Terry 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

  $219,900

  • 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

  $415,000

  • 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
• 

  

  /18

  $149,900

  • 3 Beds
  • 1 Bath
  • 1,362 Sq Ft

  11 Taylor Ave, Winchester, KY 40391

  This 3 BR home located in the heart of Winchester and just minutes from the vibrant downtown area, offers the perfect blend of convenience, character, and opportunity. Great opportunity for investors or homeowners. Outside you will love the spacious yard and can relax on the back deck with your morning coffee. Enjoy being within close proximity to local shops, dining, and community events-

  Alyssa M Boley Coldwell Banker McMahan

  11 Taylor Ave, Winchester, KY 40391
• 

  

  /33

  $309,999 Open Fri 5PM - 7PM

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

  414 Pueblo Ct, Winchester, KY 40391

  PRICE DROP and a MOTIVATED SELLER!! 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 main level hits immediately with an open, airy layout that connects living, dining, and kitchen

  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

  • 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 Open Sun 1PM - 3PM

  • 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

  $320,500

  • 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
• 

  

  /31

  $320,000

  • 5 Beds
  • 3 Baths
  • 2,624 Sq Ft

  28 Churchill Dr, Winchester, KY 40391

  ***Motivated Sellers*** Beautifully updated ranch on a new, fully finished walk out basement. 5 bedrooms, 2 being primary suites, one on the main level and one in the basement. This house is perfect for multigenerational living. New paint, floors, back splash, kitchen cabinets and granite counter tops. The fully finished basement has a newly added primary bedroom and bath. The updated bathroom

  Libby VanMeter Marshall Lane Real Estate - Lexington

  28 Churchill Dr, Winchester, KY 40391
• 

  

  /12

  $179,000

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  175 Magnolia St, Winchester, KY 40391

  Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is month to

  A. Rebecca Woods Woods Realty Group

  175 Magnolia St, Winchester, KY 40391
• 

  

  /14

  $180,000

  • 4 Beds
  • 3 Baths
  • 3,462 Sq Ft

  229 S Highland St, Winchester, KY 40391

  Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass

  Michelle Blackburn RE/MAX Creative, Winchester

  229 S Highland St, Winchester, KY 40391
• 

  

  /14

  $129,300

  • Land
  • 2.3 Acres
  • $56,217 per Acre

  110 Knox Ct, Winchester, KY 40391

  This exceptional 2.3 acre homesite offers the perfect canvas to bring your vision to life. With ample space, a prime cul-de-sac setting, and stunning surroundings, it's an ideal opportunity to create the custom home you've always wanted. Located in The Reserve, one of Winchester's premier subdivisions, this property boasts scenic daytime views and unforgettable sunsets each evening. Enjoy the

  Jarran Thomas The Agency

  110 Knox Ct, Winchester, KY 40391
• 

  /2

  $110,000

  • Land
  • 14,810 Sq Ft
  • $323,529 per Acre

  230 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

  230 Duclair Dr, Winchester, KY 40391

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