Winchester, KY Homes

• 

  

  

  /29

  Est $225,492 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  46 Hiawatha Trail, Winchester, KY 40391

  46 Hiawatha Trail, Winchester, KY 40391
• 

  

  

  /3

  $345,000

  • 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
• 

  

  

  /17

  $30,000 Sold Jun 30, 2025

  • Land
  • 1.72 Acres
  • $17,442 per Acre

  • 51 Days On Market

  12591 Ironworks Rd, Winchester, KY 40391

  This 1.722-acre lot presents a fantastic opportunity to design your ideal home in the subdivision of Eskippakithiki Overlooks. Enjoy the lovely views and ample space to unwind and relax. Located just minutes from Bert T. Combs Mountain Parkway, this property offers both convenience and tranquility. Utilities are readily available at the road, allowing you to start planning your new home right

  Cathleen Gedeon CENTURY 21 Advantage Realty

  12591 Ironworks Rd, Winchester, KY 40391
• 

  

  

  /33

  Est $236,832 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,875 Sq Ft

  14 Hiawatha Trail, Winchester, KY 40391

  14 Hiawatha Trail, Winchester, KY 40391
• 

  

  /2

  $345,000

  • 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
• 

  

  /19

  $30,000 Sold Jun 30, 2025

  • Land
  • 2.34 Acres
  • $12,821 per Acre

  • 51 Days On Market

  12651 Ironworks Rd, Winchester, KY 40391

  This 2.336-acre lot presents a fantastic opportunity to design your ideal home in the subdivision of Eskippakithiki Overlooks. Enjoy the lovely views and ample space to unwind and relax. Located just minutes from Bert T. Combs Mountain Parkway, this property offers both convenience and tranquility. Utilities are readily available at the road, allowing you to start planning your new home right

  Cathleen Gedeon CENTURY 21 Advantage Realty

  12651 Ironworks Rd, Winchester, KY 40391
• 

  

  /20

  Est $197,036 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,593 Sq Ft

  4 Hiawatha Trail, Winchester, KY 40391

  4 Hiawatha Trail, Winchester, KY 40391
• 

  

  /3

  $380,000

  • 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
• 

  

  /38

  $250,000 Sold Jun 27, 2025

  • 1,768 Sq Ft
  • $141/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  214 Southwind Dr, Winchester, KY 40391

  This turnkey home is located in a superb established location. You will love the outdoor space with a large deck overlooking the huge fenced in backyard. The tastefully updated and well-maintained home sits on a .23-acre lot. The large completely renovated kitchen with stainless appliances is ready for the cooking enthusiast. New flooring has been installed throughout and professionally painted

  Tonya Skeens RE/MAX Elite Lexington

  214 Southwind Dr, Winchester, KY 40391
• 

  

  /38

  Est $247,635 Not Listed For Sale

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

  116 Dixon Way, Winchester, KY 40391

  116 Dixon Way, Winchester, KY 40391
• 

  

  /35

  $315,000

  • 3 Beds
  • 2.5 Baths
  • 1,948 Sq Ft

  607 Colby Ridge Blvd, Winchester, KY 40391

  Built by Kessinger Construction, this open floor plan home offers plenty of layout and entertaining options. The durable luxury vinyl tile flooring is through the first floor, utility room and bathrooms. The first floor also features 9' ceilings. The kitchen offers an island ideal for bar stools and there is a spacious dining area. A door leads to a covered porch with a ceiling fan overlooking a

  Suzanne Elliott Berkshire Hathaway de Movellan Properties

  607 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /58

  $850,000 Sold Jun 27, 2025

  • 2,980 Sq Ft
  • $285/SF
  • 1 Day On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1988

  2158 Venable Rd, Winchester, KY 40391

  Perched upon 5.34 acres of flat land, this idyllic white farmhouse is ready to be loved by new owners! The property is fully fenced and has a gated entry. Step inside to an open floor plan with gleaming hardwoods throughout the main level. The family room with wood-burning stove flows into a spacious dining area. The beautifully renovated kitchen is complete with custom cabinetry, large walk-in

  Emily Miller Bluegrass Sotheby's International Realty

  2158 Venable Rd, Winchester, KY 40391
• 

  

  /21

  Est $174,289 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,102 Sq Ft

  117 Spicer Rd, Winchester, KY 40391

  117 Spicer Rd, Winchester, KY 40391
• 

  

  /33

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,527 Sq Ft

  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
• 

  

  /48

  $341,500 Sold Jun 27, 2025

  • 1,834 Sq Ft
  • $186/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1996

  401 Cedar Ct, Winchester, KY 40391

  Step into this beautifully updated 3-bedroom, 2-bath gem and fall in love with the perfect blend of charm and modern finishes! From the moment you walk through the door, you'll be greeted by an open concept living area with vaulted ceilings that fill the home with light and warmth.Enjoy new luxury vinyl plank flooring throughout the home, complemented by stylish, updated tile in the

  Geneva Wilder Selling the South Realty

  401 Cedar Ct, Winchester, KY 40391
• 

  

  /15

  Est $169,400 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  223 Ecton Rd, Winchester, KY 40391

  223 Ecton Rd, Winchester, KY 40391
• 

  

  /13

  $340,000

  • 6 Beds
  • 4 Baths
  • 4,456 Sq Ft

  410 W Lexington Ave, Winchester, KY 40391

  Estate Sale. Selling 'AS IS', in 2024 new roof, walls repaired and freshly painted throughout.Great home for a growing family, covered front porch, 10-foot ceilings upstairs and down, handicap ramp, ample parking in rear. Motivated seller, call for your private showing today

  Melisa McDonald Wrenn Realty

  410 W Lexington Ave, Winchester, KY 40391
• 

  

  /44

  $310,000 Sold Jun 27, 2025

  • 1,756 Sq Ft
  • $177/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  2482 Mina Station Rd, Winchester, KY 40391

  Move in Ready! 3 bedroom 2 full bath. Gorgeous updated kitchen with TONS of cabinet space, stainless steel appliances, and added additional cabinets with buffet space for prepartion or serving. Side entrance door with mud room area. Large dinning room with added storage and counter top space and an abundance of window light. Both bathrooms have been updated with new vanities and fixtures and

  Stephanie Hacker Kentucky Residential Real Estate, LLC

  2482 Mina Station Rd, Winchester, KY 40391
• 

  

  /28

  Est $234,603 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft

  273 Ecton Rd, Winchester, KY 40391

  273 Ecton Rd, Winchester, KY 40391
• 

  

  /73

  $339,900

  • 3 Beds
  • 2 Baths
  • 1,805 Sq Ft

  407 Fairholme Way, Winchester, KY 40391

  Looking for a newer home in a beautiful, family friendly neighborhood? Look no further than this lovely, low maintenance home in the desirable Fairholme Estates subdivision. Take a step inside and enjoy the sunlight streaming in through the abundant windows in the great room. Gleaming, easy to clean, laminate wood plank flooring spills into the spacious kitchen area which features an oversized

  Josh Wood Freedom Realty & Property Mgt

  407 Fairholme Way, Winchester, KY 40391
• 

  

  /75

  $315,000 Sold Jun 27, 2025

  • 1,848 Sq Ft
  • $170/SF
  • 46 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1991

  408 Calmes Blvd, Winchester, KY 40391

  This lovely two story home is waiting for your family to call it home! Situated in the family friendly Calmes Estates subdivision, this home includes 3 bedrooms and two full baths on the second floor, with plenty of comfortable living space on the first floor. In the front great room, natural lighting from the picture windows glows on the hardwood floors. A step around the corner into the kitchen

  Josh Wood Freedom Realty & Property Mgt

  408 Calmes Blvd, Winchester, KY 40391
• 

  

  /9

  Est $204,210 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,192 Sq Ft

  415 E Broadway St, Winchester, KY 40391

  415 E Broadway St, Winchester, KY 40391
• 

  

  /28

  $219,900

  • 3 Beds
  • 1 Bath
  • 1,053 Sq Ft

  228 Forest Ct Unit Court, Winchester, KY 40391

  This brick ranch style home is located on a quiet cul-de-sac in the residential neighborhood of Forest Park. Enjoy leisurely living in this one level home featuring a 12 X 18 Florida room overlooking a private back yard. The location is minutes from Lexington Avenue and the family/fun Legacy Park. It is move in ready and if you are ready, you may be the next owner. Make an appointment today!

  Craig Bridgewater Bridgewater Real Estate

  228 Forest Ct Unit Court, Winchester, KY 40391
• 

  

  /44

  $315,000 Sold Jun 27, 2025

  • 2,459 Sq Ft
  • $128/SF
  • 70 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  43 Skylark Dr, Winchester, KY 40391

  Discover this inviting 3-bedroom, 2-bath ranch-style home with a 2 car garage on a half acre lot! This well-maintained home offers comfort, convenience, and plenty of flexible space both inside and out. There are multiple rooms that can be used as a main living room, family room, home office, or kids playroom. Additional features include vinyl plank floors, a newer roof, a cozy gas fireplace, and

  Chad Bowman The Brokerage

  43 Skylark Dr, Winchester, KY 40391
• 

  

  /18

  Est $144,337 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  108 Crawford Ave, Winchester, KY 40391

  108 Crawford Ave, Winchester, KY 40391
• 

  

  /32

  $495,000

  • Land
  • 51 Acres
  • $9,698 per Acre

  750 Providence Ln, Winchester, KY 40391

  Welcome to your own slice of country paradise tucked away in southern Clark County! This 51+ acre tract offers a mixture of cleared pasture and mature woods, ideal for a variety of uses including cattle, crops, horses, recreation, or even your dream home site. Currently enjoyed as a private recreational family farm, the property already has electricity in place and features a cistern at an old

  Michelle Blackburn RE/MAX Creative, Winchester

  750 Providence Ln, Winchester, KY 40391
• 

  

  /41

  $272,000 Sold Jun 26, 2025

  • 1,404 Sq Ft
  • $194/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1995

  205 Beaumont Place, Winchester, KY 40391

  Immaculate 3-Bedroom Gem in Winchester! Step into this beautifully maintained 3-bedroom, 2-bath home where charm meets functionality. Gleaming hardwood floors and stylish LVP tile create a seamless flow throughout the living spaces. The fully fenced backyard offers a private oasis ideal for entertaining, relaxing, or play. Need extra space? The detached garage is perfect for a workshop, storage,

  Terry Billiter Premier Property Consultants

  205 Beaumont Place, Winchester, KY 40391
• 

  

  /30

  Est $178,704 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,432 Sq Ft

  280 Winn Ave, Winchester, KY 40391

  280 Winn Ave, Winchester, KY 40391
• 

  

  /5

  $135,000

  • Land
  • 2.50 Acres
  • $54,000 per Acre

  1200 Craig Crossing, Winchester, KY 40391

  Welcome to Lot #18 in prestigious Thoroughbred Estates?an exceptional 2.5-acre corner parcel of gently rolling countryside, graced by a serene stream and picturesque views. This remarkable homesite offers the perfect canvas for your custom estate in one of western Clark County?s most coveted locations, just off the highly sought-after McClure Road. A rare opportunity to claim a piece of

  N Seth Parker Lifstyl Real Estate

  1200 Craig Crossing, Winchester, KY 40391
• 

  

  /21

  $220,000 Sold Jun 26, 2025

  • 1,120 Sq Ft
  • $196/SF
  • 72 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1996

  520 Barlow Dr, Winchester, KY 40391

  Newly renovated home just waiting for a new owner. This 3 bedroom, 2 full bath home features all new appliances, new flooring, new paint, new roof, and much, much more. The fenced back yard is perfect for your children whether they be 2 legged or 4 legged. Located in Holiday Hills close to shopping, schools, parks, and medical care. Call your lender today to see if you qualify for the Welcome

  Keith Wilson Coldwell Banker McMahan

  520 Barlow Dr, Winchester, KY 40391
• 

  

  /10

  Est $187,650 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,230 Sq Ft

  282 Winn Ave, Winchester, KY 40391

  282 Winn Ave, Winchester, KY 40391
• 

  

  /31

  $248,000

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

  314 Carolina Ave, Winchester, KY 40391

  This beautifully 4-bedroom, 2-bath home sits on a spacious corner lot on a peaceful street near Lexington Avenue. This brick ranch style home is move in ready, and waiting for you. This home offers a great location to downtown Winchester and for all your shopping needs. Multiple fruit trees located on the property! Call and schedule your showing today!

  Travis Trimble Paragon Realty Partners

  314 Carolina Ave, Winchester, KY 40391
• 

  

  /24

  $203,000 Sold Jun 23, 2025

  • 1,289 Sq Ft
  • $157/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1990

  502 Corley Ln, Winchester, KY 40391

  You have found your 'perfect ranch'! Larger than most in the neighborhood, this 3/4 bedroom home has been very well kept and nicely updated. Under the 2 yr old roof you will find a very comfortable home with much new paint, just 1 yr old appliances, 2yr old roof and a ONE WEEK OLD HVAC system! With three bedrooms, two full baths and a bonus/4th bedroom, it will comfortably fit today's families.

  Peter doCouto Plum Tree Realty

  502 Corley Ln, Winchester, KY 40391
• 

  

  /21

  Est $147,991 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft

  48 Watts Rd, Winchester, KY 40391

  48 Watts Rd, Winchester, KY 40391
• 

  

  /41

  $254,900

  • 3 Beds
  • 2 Baths
  • 2,146 Sq Ft

  407 Walnut St, Winchester, KY 40391

  Welcome to this beautifully remodeled brick ranch sitting on a massive 1.2-acre corner lot in the heart of Winchester! This home blends modern updates with timeless charm and offers 3 spacious bedrooms, 2 full bathrooms, and a versatile bonus room that could easily serve as a fourth bedroom, home office, or playroom. Step inside to find fresh paint, brand new flooring throughout, all-new windows,

  Jason Crask THRIVE Realty

  407 Walnut St, Winchester, KY 40391
• 

  

  /36

  $300,000 Sold Jun 23, 2025

  • 2,019 Sq Ft
  • $149/SF
  • 1 Day On Market

  • 4 Beds
  • 4 Baths
  • Built 1969

  13 Shelley Dr, Winchester, KY 40391

  Gorgeous One Owner, Brick Ranch, On Basement! Meticulously Well Kept, Offering Gleaming Original Hardwoods And Fresh Paint Throughout! This 4 Bedroom, 2 1/2 Bath Home, Located In Holidays Hills Subdivision, Has Had Many Upgrades/ Additions Over The Years. Including An Updated Kitchen, Boasting Beautiful New Granite Countertops, Backsplash, Tile And Stainless Appliances! New Flooring In The

  Melissa Thompson Keller Williams Legacy Group

  13 Shelley Dr, Winchester, KY 40391
• 

  /2

  Est $174,238 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,066 Sq Ft

  64 Watts Rd, Winchester, KY 40391

  64 Watts Rd, Winchester, KY 40391
• 

  

  /25

  $255,000

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  724 Terry Dr, Winchester, KY 40391

  Nestled in the Westmeade neighborhood, this home offers the perfect blend of comfort and convenience, just minutes from the Winchester Bypass and a short drive to Lexington. With approximately 2,250 square feet of living space, this home features an inviting foyer that leads into a bright eat-in kitchen and a welcoming main living area.Down the hall, you'll find three bedrooms, along with

  Samantha Cotton National Real Estate

  724 Terry Dr, Winchester, KY 40391
• 

  

  /22

  $165,000 Sold Jun 23, 2025

  • 1,134 Sq Ft
  • $146/SF
  • 0 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1999

  515 Colby Ridge Blvd, Winchester, KY 40391

  This two bedroom, 2.5 bath townhome is located in the Colby Ridge subdivision, conveniently situated near shops, restaurants just off the bypass and minutes from I-64. The bedrooms offer ample space, while the spacious living room and eat-in kitchen provide a welcoming atmosphere. Out back, you'll find a covered patio, perfect for outdoor moments.

  Cathleen Gedeon CENTURY 21 Advantage Realty

  515 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /29

  Est $274,009 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  455 Greenway Dr, Winchester, KY 40391

  455 Greenway Dr, Winchester, KY 40391

Showing Results 81 - 120, Page 3 of 18