Winchester, KY Homes

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  $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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  /27

  $270,000 Sold Aug 25, 2025

  • 1,813 Sq Ft
  • $149/SF
  • 13 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2005

  9 Hillcrest Dr, Winchester, KY 40391

  Built To Last, This Extra Solid Ranch Home, Was Built With Top Of The Line Materials! Turn It Into Your Dream Home Or Use As A Great Investment Property, Where As, You Can Easily Double Your Square Footage When Finishing The Basement. A Beautiful Layout, Offering 3 Bedrooms, 2 Full Baths, Chef's Kitchen, Separate Laundry, Off The Attached Garage, Open Concept Living & Dining Space, On The Main.

  Melissa Brown Keller Williams Legacy Group

  9 Hillcrest Dr, Winchester, KY 40391
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  /76

  Est $561,289 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,623 Sq Ft

  110 White Conkwright Rd, Winchester, KY 40391

  110 White Conkwright Rd, Winchester, KY 40391
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  /13

  $270,000

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

  130 E Broadway St, Winchester, KY 40391

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

  Andrew Jarvis Lifstyl Real Estate

  130 E Broadway St, Winchester, KY 40391
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  /52

  $500,000 Sold Aug 25, 2025

  • 2,020 Sq Ft
  • $248/SF
  • 103 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2015

  1778 Elkin Rd, Winchester, KY 40391

  Peaceful Living on 8.83 acres of gently rolling hills in the heart of Kentucky. Breathtaking countryside features a newer custom-built home that offers peace, privacy and serene surroundings. Wake up to birdsong, watch deer wander at dusk and soak in the golden sunsets from your own front porch. Highlights include: spacious open concept kitchen with white custom cabinetry, beautiful engineered

  Vicki VanWinkle Pacesetters Real Estate

  1778 Elkin Rd, Winchester, KY 40391
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  /52

  Est $325,212 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,340 Sq Ft

  3282 Old Ruckerville Rd, Winchester, KY 40391

  3282 Old Ruckerville Rd, Winchester, KY 40391
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  /42

  $169,000

  • 2 Beds
  • 1 Bath
  • 1,046 Sq Ft

  2317 Muddy Creek Rd, Winchester, KY 40391

  Want a home with a couple of acres close to town? Then this one is for you! Located just outside of the city limits, this ranch style home offers a large living room that opens into an updated eat-in kitchen , 2 Bedrooms , 1-Bath, plus unfinished basement on a 2-Acre Lot. Step into the backyard and enjoy the view of the creek and wooded area. Plus you have a detached garage with covered

  Kathy Burton Coldwell Banker McMahan

  2317 Muddy Creek Rd, Winchester, KY 40391
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  /19

  $281,000 Sold Aug 22, 2025

  • 1,708 Sq Ft
  • $165/SF
  • 11 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1999

  223 Cross Brook Ln, Winchester, KY 40391

  Nice 3 bedroom 2 1/2 bath in one of the most desirable neighborhoods in Winchester, Colby Ridge. Brand new hvac units, large yard, and convenient to almost everything in Winchester

  Dwight Donaldson Murphy Realty Group

  223 Cross Brook Ln, Winchester, KY 40391
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  /39

  Est $361,999 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  3232 Old Ruckerville Rd, Winchester, KY 40391

  3232 Old Ruckerville Rd, Winchester, KY 40391
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  /88

  $849,900 Open Sat 1PM - 3PM

  • 3 Beds
  • 3.5 Baths
  • 4,345 Sq Ft

  1701 Gay Evans Rd, Winchester, KY 40391

  BACK ON MARKET AT NO FAULT TO SELLERS!!! 3bds with 3 BONUS ROOMS!! Your dream country retreat awaits! Nestled on 8+ scenic acres, this stunning brick ranch offers the perfect blend of modern efficiency, functional living space, and peaceful country charm. A brand-new geothermal heating and cooling system ensures year-round comfort and energy savings, giving you confidence in your home's

  Nora Williams Keller Williams Commonwealth

  1701 Gay Evans Rd, Winchester, KY 40391
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  /45

  $269,000 Sold Aug 22, 2025

  • 2,136 Sq Ft
  • $126/SF
  • 2 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1986

  402 Mcdowell Dr, Winchester, KY 40391

  Very clean, well kept home! Split foyer with plenty of space including a large kitchen with peninsula and open to dining area. Four bedrooms, 2.5 baths. Nice size living room on main level with additional family room with wood burning fireplace featuring full brick wall on lower level.Very large 2 car garage. Beautiful back covered deck that leads to a lovely gazebo in the spacious fenced in

  Christine McDonald FC Tucker Bluegrass

  402 Mcdowell Dr, Winchester, KY 40391
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  /34

  Est $465,885 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,556 Sq Ft

  5934 Irvine Rd, Winchester, KY 40391

  5934 Irvine Rd, Winchester, KY 40391
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  /25

  $250,000 Open Sat 2PM - 4PM

  • 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

  $369,500 Sold Aug 22, 2025

  • 2,456 Sq Ft
  • $150/SF
  • 11 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2022

  148 Gibson Way, Winchester, KY 40391

  NEW PRICE!Better Than New Construction!!! This Spacious 4 Bedroom 2 1/2 Bath Home Is Move In Ready And Has A Beautiful Farm View From Your Covered Porch. Features Include A Large Open Living Room And Kitchen With Plenty Of Cabinet Space; Large Island With Faucet; Granite Countertops; Tile Backsplash; Stainless Steel Appliances; Large pantry; Gas Log Fireplace; Gas Heat; Gas Water Heater;

  W Patrick Arvin Keller Williams Commonwealth

  148 Gibson Way, Winchester, KY 40391
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  /36

  Est $507,084 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,892 Sq Ft

  5487 Irvine Rd, Winchester, KY 40391

  5487 Irvine Rd, 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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  /3

  $94,000 Sold Aug 22, 2025

  • Land
  • 4.02 Acres
  • $23,383 per Acre

  • 140 Days On Market

  2010 Athens Boonesboro Rd, Winchester, KY 40391

  Prime building lot - 4 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2010 and 2058 approved shared entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first choice on

  Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
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  /34

  Est $337,641 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,633 Sq Ft

  4759 Ironworks Rd, Winchester, KY 40391

  4759 Ironworks Rd, Winchester, KY 40391
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  /7

  $45,000

  1559 Amster Grove Rd, Winchester, KY 40391

  Looking for your next investment or weekend escape? This unique property offers two dwellings on one lot, right along the KY River. While it needs a full restoration, the possibilities are endless—whether you're dreaming of a private vacation retreat, a charming getaway spot, or a high-income short-term rental, this is a diamond in the rough ready to shine. Key Highlights: Two dwellings on one

  Erin Lewis Christies International Real Estate Bluegrass

  1559 Amster Grove Rd, Winchester, KY 40391
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  /24

  $277,500 Sold Aug 21, 2025

  • 1,588 Sq Ft
  • $175/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  10 Howard Dr, Winchester, KY 40391

  Charming All-Brick Ranch with Bonus Space & Huge Yard!This beautifully updated 3-bedroom, 2-bathroom all-brick ranch offers timeless charm and modern touches throughout. Situated on a generous, fully fenced lot with mature trees, this home features fresh neutral paint, stylish shiplap accents, and abundant natural light. The spacious detached bonus room is perfect for a home office, gym,

  Holly Goeing The Agency

  10 Howard Dr, Winchester, KY 40391
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  /41

  Est $357,310 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft

  2100 Miller Hunt Rd, Winchester, KY 40391

  2100 Miller Hunt Rd, 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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  /23

  $225,000 Sold Aug 21, 2025

  • 1,080 Sq Ft
  • $208/SF
  • 12 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1972

  26 Stefanie Ct, Winchester, KY 40391

  Welcome to this charming 3BR-1BA brick ranch nestled in a quiet court in Winchester. The home features classic hardwood flooring throughout, offering timeless style and easy maintenance. Outback you will enjoy a fenced in yard and a detached 1 car garage. Don't miss the opportunity to own a move-in-ready gem. Call today for your showing.

  Alyssa M Boley Coldwell Banker McMahan

  26 Stefanie Ct, Winchester, KY 40391
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  /38

  Est $355,357 Not Listed For Sale

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

  875 Miller Hunt Rd, Winchester, KY 40391

  875 Miller Hunt Rd, Winchester, KY 40391
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  /34

  $275,000

  • Land
  • 6.08 Acres
  • $45,230 per Acre

  190 Privacy Ln, Winchester, KY 40391

  6.08 acres settled in Clark County with access from both Privacy Ln and Little Stoner Rd. This property boasts a 30x56 with 10 foot wall Kentucky Steel Truss building with concrete floors, gas and wood burning heat, full bath, and a car lift. Additionally, there is a barn with a 3 bay shed attached.

  Jason Joseph Keller Williams Commonwealth

  190 Privacy Ln, Winchester, KY 40391
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  /33

  $335,000 Sold Aug 20, 2025

  • 1,527 Sq Ft
  • $219/SF
  • 38 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1946

  543 S Maple St, Winchester, KY 40391

  Nestled on the charming street of South Maple this beautiful ranch home offers the perfect blend of comfort and convenience. Featuring three bedrooms and two modern bathrooms, this single-level living space is designed for ease and elegance. The open floor plan seamlessly connects the living room, dining area, and kitchen, creating a welcoming atmosphere for gatherings. Large windows fill

  Lucy Martin Jenkins United Real Estate Bluegrass

  543 S Maple St, Winchester, KY 40391
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  /35

  Est $390,087 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,964 Sq Ft

  4476 Ecton Rd, Winchester, KY 40391

  4476 Ecton Rd, Winchester, KY 40391
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  /4

  $25,000

  • Land
  • 0.17 Acre
  • $147,059 per Acre

  117 4th St, Winchester, KY 40391

  Discover the potential of this spacious 0.17-acre residential property nestled in a neighborhood community on clear and level vacant lot located in a Cul-de-sac of Lincoln Park Subdivision. This could be an investment opportunity as well, for ideal savvy investors looking to diversify your portfolio this property would be perfect for building a custom home, holding for future value, or develop

  Anita McDermott Keller Williams Bluegrass Realty

  117 4th St, Winchester, KY 40391
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  /25

  $287,000 Sold Aug 20, 2025

  • 1,402 Sq Ft
  • $205/SF
  • 36 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  220 Mcdowell Dr, Winchester, KY 40391

  This beautiful 3BR, 2BA ranch style home offers a blend of comfort and style. Featuring an inviting open concept layout, the spacious living area flows effortlessly into the kitchen and dining spaces- perfect for family gatherings or entertaining guests. The exterior boasts charming curb appeal with a well maintained lawn, new siding, stone accents, and a cozy covered front porch. A 2 car

  Alyssa M Boley Coldwell Banker McMahan

  220 Mcdowell Dr, Winchester, KY 40391
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  /42

  Est $316,510 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  1570 Little Stoner Rd, Winchester, KY 40391

  1570 Little Stoner 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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  /20

  $205,000 Sold Aug 19, 2025

  • 1,113 Sq Ft
  • $184/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1999

  202 Custer Ct, Winchester, KY 40391

  Welcome to this inviting 3-bedroom, 2-bath home. Whether you're looking for a starter home to make your own or a smart investment property, this one checks all the boxes. Living area filled with natural lighting leading into the kitchen. The primary suite features its own private bath and walk in closet. While two additional bedrooms share a full hall bathroom. Outside, enjoy a generous

  Brittany Beer EXP Realty, LLC

  202 Custer Ct, Winchester, KY 40391
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  /41

  Est $355,027 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,988 Sq Ft

  5751 Mount Sterling Rd, Winchester, KY 40391

  5751 Mount Sterling Rd, 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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  /32

  $200,000 Sold Aug 19, 2025

  • 1,164 Sq Ft
  • $172/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1945

  116 Linden Ave, Winchester, KY 40391

  Welcome to 116 Linden Avenue located minutes from Winchester's charming downtown. This move in ready 3-bedroom, 2-bath home is complete with fresh paint and a great layout that offers both comfort and functionality. Enjoy the convenience of a first-floor primary bedroom and the bonus of a spacious yard, perfect for outdoor entertaining, gardening, or relaxing. Whether you're looking for your next

  Robert Bratton Bluegrass Sotheby's International Realty

  116 Linden Ave, Winchester, KY 40391
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  /36

  Est $363,719 Not Listed For Sale

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

  610 Old Ruckerville Rd, Winchester, KY 40391

  610 Old Ruckerville Rd, Winchester, KY 40391
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  /31

  $245,000

  • 3 Beds
  • 2.5 Baths
  • 1,935 Sq Ft

  203 Inverness Ln, Winchester, KY 40391

  At 203 Inverness Lane, life feels a little easier. Set on a corner lot at the entry of a quiet street, this townhome welcomes you in with beautiful hardwood floors and natural light pouring through the windows. The layout flows effortlessly. Picture laughter in the living room drifting into the dining space as dinner simmers in the kitchen, or doors opening to the deck where summer evenings are

  Kymberly McCreary EXP Realty, LLC

  203 Inverness Ln, Winchester, KY 40391
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  /22

  $600,000 Sold Aug 19, 2025

  • Land
  • 12.38 Acres
  • $48,465 per Acre

  • 125 Days On Market

  1203 Irvine Rd, Winchester, KY 40391

  This 12+ acre piece of prime real estate is full of potential! Zoned for business uses, the location is conveniently located with easy access to Veterans Memorial Bypass, I-64, and downtown Winchester. Utilities are already available at this property and there is a small structure included in as-is condition. Give us a call with any further questions.

  Josh Wood Freedom Realty & Property Management

  1203 Irvine Rd, Winchester, KY 40391
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  /16

  Est $135,910 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft

  2584 Irvine Rd, Winchester, KY 40391

  2584 Irvine Rd, 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

Showing Results 121 - 160, Page 4 of 18