Winchester, KY 1-Story Homes for Sale

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  /40

  $355,000

  • 3 Beds
  • 3 Baths
  • 2,166 Sq Ft

  115 Woodford Dr, Winchester, KY 40391

  Discover a perfect blend of comfort and elegance as you step inside this charming home. Sitting on a generous 1/4 acre lot, this property offers a peaceful retreat with space to relax and entertain both inside and out. The heart of the home is the airy and open kitchen, featuring an oversized island that is perfect for gathering and sharing a meal. A dedicated keeping room provides a cozy

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 251-8500

  115 Woodford Dr, Winchester, KY 40391
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  Explore Winchester

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  /71

  $799,999

  • 4 Beds
  • 2.5 Baths
  • 5,290 Sq Ft

  186 Chardonnay Ct, Winchester, KY 40391

  Step into a world of both comfort and convenience with this beautiful 3/4 bedroom, two and one half bath, perfectly designed for relaxation and entertainment. Key features of this property include outdoor spaces to enjoy morning coffee or quiet evening chats. The cozy back porch extends your living space, ideal for dining and enjoying the tranquil surroundings, The beautifully designed patio

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 813-4308

  186 Chardonnay Ct, Winchester, KY 40391
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  /14

  $312,975

  • 2 Beds
  • 1 Bath
  • 1,116 Sq Ft

  1363 Clintonville Rd, Winchester, KY 40391

  Here's your chance to own a rare 5-acre property in Clark County, one of Central Kentucky's most desirable areas. Tucked just minutes from downtown Winchester, the Hamburg corridor, and Lexington, this property blends convenience with the peacefulness of country living. Whether you're dreaming of building a brand-new home, expanding into a mini farm, or investing in future growth, this land gives

  

  Rebakah Goodpaster

  Keller Williams Legacy Group

  (859) 659-6863

  1363 Clintonville Rd, Winchester, KY 40391
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  /75

  $435,000

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  291 Log Lick Rd, Winchester, KY 40391

  Beautiful home on 5 acres of land. Approximately 2 acres are cleared; the other 3 acres are wooded. There is a metal barn and a 3-car detached garage. Pond is stocked with catfish and blue gill. You might look out at any time and see deer or wild turkeys. The 2 fireplaces do not work. New HVAC and all duct work replaced 6 or 7 years ago. Zoned. Entire house was professionally painted last year

  Joyce Ratliff Tom Goebel & Company

  291 Log Lick Rd, Winchester, KY 40391
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  /31

  $365,000

  • 3 Beds
  • 3 Baths
  • 1,832 Sq Ft

  536 S Maple St, Winchester, KY 40391

  No Expense was spared on this beautiful, updated home! The Living Room showcases new hardwood flooring and an electric fireplace with changing lights to set the mood! Updated kitchen with new white cabinets, granite counter tops, tile backsplash and all new appliances for easy entertaining! A dining room with a pantry make storage and dinner a breeze! 3 generous sized bedrooms, 3 full bathrooms

  Whitney Ensor Ensor Real Estate, LLC

  536 S Maple St, Winchester, KY 40391
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  /28

  $325,000

  • 2 Beds
  • 1 Bath
  • 1,170 Sq Ft

  398 Pine Ridge Rd, Winchester, KY 40391

  Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment you walk in. Enjoy the outdoors from

  Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
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  /34

  $312,750

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  123 Strawberry Ln, Winchester, KY 40391

  Priced below recent appraisal this almost new 3 bed 2 bath open layout ranch. This split bedroom design places two bedrooms and the hall bath off the entry and the primary bedroom suite at the rear of the home. The central kitchen offers both a breakfast area and countertop dining at the island, and opens to the family room. Granite kitchen counter tops with stainless steel 50/50 under-mount sink

  Joseph Smallwood Christies International Real Estate Bluegrass

  123 Strawberry Ln, Winchester, KY 40391
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  /14

  $394,999

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  408 Corinne Ct, Winchester, KY 40391

  Come see this immaculate 3 bedroom, 2 bath single-story ranch with an open-concept split bedroom layout and 1,604 square feet of living space. This home has been beautifully maintained and is ready for its next owner. Inside you will find laminate and tile floors and stainless steel appliances that make daily living easy and stylish. The spacious design flows seamlessly, creating a bright and

  Caleb Gonzalez The Brokerage

  408 Corinne Ct, Winchester, KY 40391
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  /37

  $350,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft

  103 Mayfair Ct, Winchester, KY 40391

  This well-maintained ranch offers 3 bedrooms, 2 full baths, and a 3-car garage that's insulated, heated, and wired with a — Looks good. The garage has a 100amp service, 3each. 220v 30amp breakers—ideal for hobbies or extra storage. The property sits on a great lot with a fenced-in backyard, perfect for both privacy and entertaining. Inside, the split-bedroom design separates the secondary

  Carlos Elliott Tru Life Real Estate

  103 Mayfair Ct, Winchester, KY 40391
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  /19

  $410,000

  • 4 Beds
  • 2.5 Baths
  • 3,806 Sq Ft

  410 Lyon Dr, Winchester, KY 40391

  Presenting this lovely, move in ready brick ranch on a full walkout basement located in a desirable neighborhood within minutes to downtown, schools, and the bypass. With four bedrooms and three bathrooms, a large updated kitchen, and spacious finished basement, this home has space for everyone! Meticulously maintained, and thoughtfully updated with new floors, fresh paint, new windows and more!

  Natalie Nohel CENTURY 21 Advantage Realty

  410 Lyon Dr, Winchester, KY 40391
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  /53

  $459,000

  • 4 Beds
  • 3 Baths
  • 2,844 Sq Ft

  129 Lana Ln, Winchester, KY 40391

  Open House -Sunday 1-3 p.m.! Stunning renovated 4-BR,3BA brick ranch with walkout basement, in-ground pool & pool house! This home has undergone extensive remodeling to improve traffic flow while preserving distinct living spaces. These updates create a seamless and intuitive flow through, enhancing both functionality and style! Recent Improvements and Updates-fully remodeled kitchen, bathrooms,

  Jo Gawthrop Keller Williams Bluegrass Realty

  129 Lana Ln, Winchester, KY 40391
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  /57

  $630,000

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

  670 Lillies Ferry Rd, Winchester, KY 40391

  Escape to this serene and private 12+ acre property, boasting a 3BR/2BA home sitting on a partially finished walkout basement, that provides ample space for a home office, playroom, or additional living area. This charming home has lots of recent upgrades, including a brand new HVAC system, ensuring a comfortable living space year-round. The exterior of the home has been upgraded with new

  Jennifer Helton EXP Realty, LLC

  670 Lillies Ferry Rd, Winchester, KY 40391
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  /9

  $365,000

  • 3 Beds
  • 2.5 Baths
  • 2,868 Sq Ft

  508 Boone Ave, Winchester, KY 40391

  3 bedroom, 2 1/2 bath brick home in Witherspoon Subdivision. New roof, new freeze resistant water lines, new heat and air, new appliances, and backsplash. Full basement with double space garage. Spacious formal living room and separate formal dining room. Great room includes breakfast area and sitting area, and fireplace. Large master ensuite includes closet with plenty of storage space.

  Donna C. Slone-Crumbie Wright Realty

  508 Boone Ave, Winchester, KY 40391
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  /27

  $399,000

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft

  5705 Mount Sterling Rd, Winchester, KY 40391

  The one you've been waiting for. This beautiful home has so much to offer. 4 bedrooms, 2 1/2 bathrooms, with full basement and mother in law suite. It sits on just over 3 spacious acres. There is a 24X36 work shop just built in 2022. The roof and HVAC are just 6 years old. The water heater is 6 months old. The property has 10 beautiful apple trees and 3 pear trees. The home is just minutes from

  Dale Hatton Dream Maker Realty, LLC

  5705 Mount Sterling Rd, Winchester, KY 40391
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  /36

  $360,000

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  208 Citation Ct, Winchester, KY 40391

  One owner, all electric, 2 BR/2Ba ranch with a bonus room that could be an office or a third bedroom. The open floor great room with ample windows to brighten it supports the handicapped features of the primary bedroom, primary bathroom, garage and more. Enjoy the large pantry off the kitchen area and the island that has room to slide a chair under. (see photos) Kitchen appliances include

  Garnett Davis Tom Goebel & Company

  208 Citation Ct, Winchester, KY 40391
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  /41

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft

  118 Windridge Dr, Winchester, KY 40391

  Located in the Windridge neighborhood with easy access to both Bypass Rd and Boone Ave, this charming brick ranch offers 3 bedrooms, 2 full baths, and character throughout. Inside, you'll find hardwood and tile floors (no carpet!), a spacious kitchen with plenty of cabinet space that opens into the dining area and living room, complete with a cozy ventless gas fireplace. Step out back to your own

  Michelle Blackburn RE/MAX Creative, Winchester

  118 Windridge Dr, Winchester, KY 40391
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  /80

  $524,000

  • 3 Beds
  • 2.5 Baths
  • 4,933 Sq Ft

  160 Agawam Rd, Winchester, KY 40391

  Welcome to this beautifully maintained brick ranch home set on a spacious and private 5-acre fenced lot. This versatile property offers the perfect blend of comfort, functionality, and rural charm - ideal for families, hobby farmers, or equestrian enthusiasts. Inside, you'll find 3 bedrooms and 3 bathrooms with a fully finished basement that offers ample space for additional bedrooms, a home gym,

  Megan McCoy Keller Williams Legacy Group

  160 Agawam Rd, Winchester, KY 40391
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  /18

  $389,900

  • 3 Beds
  • 3 Baths
  • 2,516 Sq Ft

  110 Hampton Ave, Winchester, KY 40391

  Move-in ready mid- century brick ranch home! Features 3 bedrooms, 3 full baths, new kitchen with granite countertops, 3 woodburning fireplaces, formal dining or family room, full basement with huge rec room or space to have 4th bedroom, 1 car garage, 2 storage buildings & fenced in yard! Updates include windows, doors, metal roof, new paint inside & out, new flooring in basement & bedrooms, all

  Angie Conley Dixon Dixon Properties

  110 Hampton Ave, Winchester, KY 40391
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  /4

  $369,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  206 Jett Dr, Winchester, KY 40391

  New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

  Mila Ensor Ensor Real Estate, LLC

  206 Jett Dr, Winchester, KY 40391
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  /3

  $380,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  270 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms on unfinished walkout basement.The large primary suite is a true retreat, complete with a generously sized walk-in closet

  Rex Hall United Real Estate Bluegrass

  270 Evergreen Dr, Winchester, KY 40391
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  /3

  $380,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  230 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

  Rex Hall United Real Estate Bluegrass

  230 Evergreen Dr, Winchester, KY 40391
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  /3

  $345,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  225 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

  Rex Hall United Real Estate Bluegrass

  225 Evergreen Dr, Winchester, KY 40391
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  /2

  $345,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  215 Evergreen Dr, Winchester, KY 40391

  Welcome to Triple Crown - a stunning proposed construction home nestled in the beautiful Locust Hill Acres community. Thoughtfully designed with an open-concept layout, this home offers 3 comfortable bedrooms, 2 full bathrooms, and versatile living spaces perfect for today's lifestyle.The expansive primary suite serves as a private sanctuary, complete with a spacious walk-in closet and a

  Rex Hall United Real Estate Bluegrass

  215 Evergreen Dr, Winchester, KY 40391
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  /3

  $380,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  200 Evergreen Dr, Winchester, KY 40391

  Introducing the Run For The Roses - Proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms. The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite bathroom. The kitchen

  Rex Hall United Real Estate Bluegrass

  200 Evergreen Dr, Winchester, KY 40391
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  /29

  $252,500

  • 4 Beds
  • 2 Baths
  • 1,593 Sq Ft

  306 Snowden Dr, Winchester, KY 40391

  Home is quietly nestled within the Wesleyan Park subdivision just off the Winchester Bypass. While convenient location is obvious this home boast many updates throughout. Including flooring, appliances, New roof, HVAC, Water heater and so much more. Schedule your showing while you can!

  Michael Hilario The Agency

  306 Snowden Dr, Winchester, KY 40391
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  /50

  $850,000

  • 4 Beds
  • 3 Baths
  • 3,311 Sq Ft

  7300 Old Boonesboro Rd, Winchester, KY 40391

  This beautiful home sits on over 7 acres of peaceful countryside. The private outdoor space includes a huge deck with a lovely view and an inviting covered front porch. The backyard would make the perfect space for your own dream swimming pool. Since the property has a 3-car detached garage; a 2-car attached garage plus a 1275 square feet equipment building there is plenty of space for all of

  Tonya Skeens RE/MAX Elite Lexington

  7300 Old Boonesboro Rd, Winchester, KY 40391
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  /41

  $74,950

  • 1 Bed
  • 1 Bath

  145 Riverbend Ln, Winchester, KY 40391

  --- **Riverside Cabin Retreat - Almost 5 Acres at the Mouth of the KY & Red Rivers** Discover unlimited possibilities with this rare gem nestled where the Kentucky and Red Rivers meet. This scenic 5-acre property offers: - **Multiple camping spots** surrounded by natural beauty - **River access** perfect for fishing, kayaking, and duck hunting - A cozy **cabin** ideal for a

  Darrell Tackett Dream Maker Realty, LLC

  145 Riverbend Ln, Winchester, KY 40391
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  /46

  $284,900

  • 3 Beds
  • 2 Baths
  • 1,454 Sq Ft

  165 Hilltop Dr, Winchester, KY 40391

  This stunning property is ideally located and is an absolute must see! This lovely home is located on over a quarter acre lot with gorgeous farm views. Featuring an open floor plan that is perfect for entertaining, a beautiful kitchen with granite countertops, stainless appliances, and a large island. The primary suite offers a large en-suite full bath with a double bowl raised vanity. This

  Tyson Walters Kassie & Associates

  165 Hilltop Dr, Winchester, KY 40391
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  /32

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,958 Sq Ft

  727 Terry Dr, Winchester, KY 40391

  Located near the end of a quiet cul-de-sac, this brick ranch features a finished basement and loads of character—completely move-in ready! Step inside to an inviting open-concept living, dining, and kitchen area with high ceilings and a warm wood beam accent. Hardwood and tile flooring run throughout the home, plus don't miss the granite countertops in the kitchen. Down the hall are 3 bedrooms,

  Michelle Blackburn RE/MAX Creative, Winchester

  727 Terry Dr, Winchester, KY 40391
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  /25

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,438 Sq Ft

  231 Leslie Dr, Winchester, KY 40391

  This adorable three-bedroom, two-bath home is ready for it's new owner to love! The open floor plan makes this home feel spacious and bright. The yard is perfect for family fun or entertaining.

  Destiny Darby Keller Williams Commonwealth

  231 Leslie Dr, Winchester, KY 40391
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  /34

  $235,000

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

  37 7th St, Winchester, KY 40391

  Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

  Andrew Fugitt Coldwell Banker McMahan

  37 7th St, Winchester, KY 40391
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  /26

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,295 Sq Ft

  175 Waterworks Rd, Winchester, KY 40391

  The country house you have been looking for! 3 bed, 2 bath with an amazing front porch where you can sit and view the small stream in the front yard! Sitting on 3.17 acres with approximately 735 feet of road frontage which should allow for division for a second lot / home. 565 sq ft all metal detached garage, a livestock barn with 3 stalls, and a back deck with farm views. High speed internet

  Jason Townsend Kentucky Residential Real Estate, LLC

  175 Waterworks Rd, Winchester, KY 40391
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  /13

  $150,000

  • 2 Beds
  • 1 Bath
  • 1 Sq Ft

  208 4th St, Winchester, KY 40391

  Discover the potential of this spacious 0.27-acre residential home nestled in a neighborhood community on clear and level land located in a Cul-de-sac of Lincoln Park Subdivision. This Property features 2-bedrooms, 1-Bathroom, a large family room with a fireplace. There is also a large versatile barn on the property as well. This could be an investment opportunity as well, for ideal savvy

  Anita McDermott Keller Williams Bluegrass Realty

  208 4th St, Winchester, KY 40391
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  /24

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft

  27 Ashland Ave, Winchester, KY 40391

  Move right in and enjoy this well-maintained 3 bed, 2 bath ranch in the heart of Massie Addition! Thoughtfully updated with a recent roof on home and garage, new hot water heater (2025), and a modern, fresh interior paint palette, this home is ready for you. The generous ~half-acre lot offers room to garden, play, or relax under the trees, while the detached 2-car garage adds excellent storage

  Robin Mobley-Mosher Marshall Lane Real Estate - Lexington

  27 Ashland Ave, Winchester, KY 40391
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  /20

  $289,000

  • 2 Beds
  • 2 Baths
  • 1,674 Sq Ft

  800 Country Club Ct, Winchester, KY 40391

  Great Investment Property. This cozy Winchester duplex is in a prime location. Just minutes from the Bypass and downtown. Two bedrooms with 2 full baths. The location is close to several retail stores, restaurants, and golf courses. Property is being sold together and will not separate.

  Dale Hatton Dream Maker Realty, LLC

  800 Country Club Ct, Winchester, KY 40391
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  /31

  $174,900

  • 3 Beds
  • 1 Bath
  • 1,332 Sq Ft

  120 E Lexington Ave, Winchester, KY 40391

  Looking for an affordable home? Look no further than this recently updated 3 bedroom 1 bath with possible 4th bedroom or bonus room. New flooring, appliances, fixtures and new hvac. Replacement windows before current owner. Great starter home located convenient to downtown area and shopping.

  Chris Johnson Plum Tree Realty

  120 E Lexington Ave, Winchester, KY 40391
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  /21

  $149,000

  • 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

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
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  /20

  $159,900

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  103 Yorktowne Ct, Winchester, KY 40391

  Affordable and move-in ready! 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, dining, and easy access to I-64 while still tucked away on a quiet

  Susy Esquivel Allied Realty

  103 Yorktowne Ct, Winchester, KY 40391
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  /13

  $185,000

  • 2 Beds
  • 1 Bath
  • 902 Sq Ft

  220 Pendleton St, Winchester, KY 40391

  Fully renovated home with new exterior vinyl walls and dimensional shingle rood. Interior has received new insulation, drywall, all new wiring, partial windows, new appliances and counters, new bathroom vanity/tub/toilet, new LVP floor coverings, new interior/exterior doors, new heat pump/water heater.

  Steve Adams Steven D Adams Real Estate Services, LLC

  220 Pendleton St, Winchester, KY 40391
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  /36

  $285,000

  • 3 Beds
  • 2.5 Baths
  • 1,715 Sq Ft

  103 Hampton Ave, Winchester, KY 40391

  A timeless brick ranch in one of Winchester's most established neighborhoods on a corner lot. This 3 bedroom, 2.5 bath home offers two living areas and a cozy fireplace. Spacious backyard, covered front porch, and a wrap-around driveway for a private entrance. All just minutes from downtown, schools, and I-64. The home combines classic comfort, location, and room to grow on a walk-out basement.

  Brett Bussell Turf Town Properties

  103 Hampton Ave, Winchester, KY 40391

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