Winchester, KY Homes

• 

  

  

  /33

  $240,000 Sold Sep 10, 2025

  • 2,472 Sq Ft
  • $97/SF
  • 18 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1969

  752 Wayland Dr, Winchester, KY 40391

  This ranch style house is located minutes from Fayette County line and minutes from the I-64 and I-75 corridors. This house features 4 bedrooms and 2 full baths on a walk-out basement. The owners remodeled several years ago with new kitchen and primary suite. The house is situated on a .53 acre lot within a quiet residential neighborhood. Looking for a house to make your home? come see this

  Craig Bridgewater Bridgewater Real Estate

  752 Wayland Dr, Winchester, KY 40391
• 

  

  

  /16

  Est $129,000 Not Listed For Sale

  • Studio
  • 1,271 Sq Ft

  4523 Trapp Goffs Corner Rd, Winchester, KY 40391

  4523 Trapp Goffs Corner Rd, Winchester, KY 40391
• 

  

  

  /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
• 

  

  

  /17

  $190,000 Sold Sep 10, 2025

  • 1,059 Sq Ft
  • $179/SF
  • 50 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1960

  114 Sunset Heights, Winchester, KY 40391

  Conveniently located, well maintained ranch with 3 bedrooms in established neighborhood, awaiting its new owner! With a newer roof, gutters (with guards), furnace and water heater...it helps take some maintenance worries away! Ample storage with storage closet in carport, and detached shed. Three hundred sq.ft. 3-seasons area in rear of home, which could be used year-round with the addition of a

  Susan Baldwin Rector Hayden Realtors

  114 Sunset Heights, Winchester, KY 40391
• 

  

  

  /66

  Est $589,795 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,479 Sq Ft

  5078 Trapp Goffs Corner Rd, Winchester, KY 40391

  5078 Trapp Goffs Corner Rd, Winchester, KY 40391
• 

  

  /37

  $350,000

  • 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
• 

  

  /36

  $472,500 Sold Sep 09, 2025

  • 2,593 Sq Ft
  • $182/SF
  • 1 Day On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2007

  208 Royal Oak Dr, Winchester, KY 40391

  Elegant brick and Stone Beauty in sought-after Royal Oak Subdivision! This stunning 4-bedroom, 2.5 bath home seamlessly blends timeless charm with modern comfort. The spacious primary suite is conveniently located on the main level, featuring a luxurious ensuite bath and soaring cathedral ceilings that create a serene retreat. Entertain in style with a grand living room, also boasting cathedral

  Megan McCoy Keller Williams Legacy Group

  208 Royal Oak Dr, Winchester, KY 40391
• 

  

  /58

  Est $348,882 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,064 Sq Ft

  3076 Thomson Station Rd, Winchester, KY 40391

  3076 Thomson Station Rd, Winchester, KY 40391
• 

  

  /64

  $440,000

  • 5 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  1857 Ironworks Rd, Winchester, KY 40391

  Get a piece of Bluegrass heaven in this move-in ready modern farmhouse on just under 5acres in Clark County. Dreaming of the country life? This is it, originally built in 1865 this timeless home has been completely updated and seamlessly blended the history with modern elegant design and livability. Classic farmhouse style with tons of natural light that bring the outside in. Spacious great room

  Meredith Walker Bluegrass Sotheby's International Realty

  1857 Ironworks Rd, Winchester, KY 40391
• 

  

  /57

  $260,000 Sold Sep 09, 2025

  • 1,633 Sq Ft
  • $159/SF
  • 4 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1945

  7934 Ironworks Rd, Winchester, KY 40391

  Strategically located, this two story home was built to allow for a nice breeze during hotter months, leading to lower electricity bills. The home remains in pristine working order, as well as detached garage and 3 stall barn with water hookup. Nearly 5 acres, the property is already set up with multiple sized paddocks for horses, cattle, goats, etc. Built with the original house, the oversized

  Greg Wood Freedom Realty & Property Management

  7934 Ironworks Rd, Winchester, KY 40391
• 

  

  /39

  Est $413,952 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,314 Sq Ft

  900 Vienna Rd, Winchester, KY 40391

  900 Vienna Rd, Winchester, KY 40391
• 

  

  /58

  $457,900 Open Sat 2PM - 4PM

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

  42 Mockingbird Valley Rd, Winchester, KY 40391

  The term 'Move In Ready' really and truly applies here at 42 Mockingbird Valley Road! Versatility, Family Friendly, Well Constructed and Maintained, Mature Landscaping and Quiet Location are among the many attributes you'll find. This beautiful one level home on a full basement is ready for your personal touches.Sparking hardwood floors throughout will highlight and set off your furniture

  Markus Cross Keller Williams Commonwealth

  42 Mockingbird Valley Rd, Winchester, KY 40391
• 

  

  /37

  $392,500 Sold Sep 08, 2025

  • 2,991 Sq Ft
  • $131/SF
  • 24 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1991

  576 Marseille Blvd, Winchester, KY 40391

  **Priced to sell and well below the attached appraisal dated 7/16/2025.** Welcome to this beautifully maintained 4-bedroom, 3-bathroom home with a walkout basement, nestled in the desirable Oak Hill subdivision. Thoughtfully designed and extensively landscaped both front and back, this home offers the perfect blend of comfort, functionality, and outdoor living. Step inside to discover spacious

  James Turek Bluegrass Sotheby's International Realty

  576 Marseille Blvd, Winchester, KY 40391
• 

  

  /43

  Est $245,914 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,358 Sq Ft

  2270 Mina Station Rd, Winchester, KY 40391

  2270 Mina Station Rd, Winchester, KY 40391
• 

  

  /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
• 

  

  /38

  $258,900 Sold Sep 08, 2025

  • 1,678 Sq Ft
  • $154/SF
  • 1 Day On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2000

  313 Geronimo Ct, Winchester, KY 40391

  Welcome to 313 Geronimo Court in Winchester, KY well-maintained home nestled on a quiet cul-de-sac, offering comfortable living with a functional layout and great outdoor space. Inside, you will find water-resistant laminate wood-look flooring and tile throughout the main living areas, creating a clean and durable foundation. The kitchen includes refrigerator and stove with a cozy dining area

  Shari Frasure Keller Williams Commonwealth

  313 Geronimo Ct, Winchester, KY 40391
• 

  

  /42

  Est $411,526 Not Listed For Sale

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

  920 Log Lick Rd, Winchester, KY 40391

  920 Log Lick Rd, Winchester, KY 40391
• 

  

  /82

  $429,000

  • 4 Beds
  • 3.5 Baths
  • 2,637 Sq Ft

  397 Calmes Blvd, Winchester, KY 40391

  This stunning, renovated home is move-in ready and packed with upgrades that make it an absolute must-see! Step inside and enjoy the fresh, modern feel of the newly painted interior, with updated flooring throughout—including brand-new flooring in the basement, kitchen, and upstairs hall, along with plush new carpet on the upper level. The two remodeled bathrooms feature sleek finishes that add a

  Omar Shalash Tru Life Real Estate

  397 Calmes Blvd, Winchester, KY 40391
• 

  

  /38

  $599,500 Sold Sep 08, 2025

  • 2,204 Sq Ft
  • $272/SF
  • 72 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2025

  102 Bella Shae Way, Winchester, KY 40391

  Introducing the Stonewall plan—a stunning brick and stone ranch ideally positioned on a corner lot in Mallard Cove. This 4 bedroom, 2 full bath home with a side-entry garage offers timeless curb appeal and high-end features throughout. The thoughtfully designed layout includes a spacious living room with vaulted ceilings, arched and lighted built-ins, and a gas fireplace with a floor-to-ceiling

  Shane Underwood Keller Williams Commonwealth

  102 Bella Shae Way, Winchester, KY 40391
• 

  

  /38

  Est $299,692 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  306 Trapp Goffs Corner Rd, Winchester, KY 40391

  306 Trapp Goffs Corner Rd, Winchester, KY 40391
• 

  

  /67

  $539,000

  • 4 Beds
  • 2.5 Baths
  • 3,989 Sq Ft

  415 David Ln, Winchester, KY 40391

  Location, location, location!! This house, 415 David Lane, is located in the most sought after neighborhood, Stoneybrook. It is approximately 20 minutes from the Hamburg area of Lexington and minutes from the I-75 corridor. Enter the house from the welcoming front porch to a entryway and notice immediately the gleaming hardwood floors and the stairway leading to the second floor. The primary

  Craig Bridgewater Bridgewater Real Estate

  415 David Ln, Winchester, KY 40391
• 

  

  /56

  $639,000 Sold Sep 06, 2025

  • 4,021 Sq Ft
  • $159/SF
  • 37 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1975

  4455 Colby Rd, Winchester, KY 40391

  Gorgeous Ranch Home On Basement, Situated Perfectly On Over 3.5 Lush Acres Of Level Seclusion, As Property Is Lined Beautiful, Mature Trees! Enjoy Peace & Quiet In This Newly Renovated Home, Offering 6 Bedrooms, 5 Baths, Ample Family Space, Home Office, (Fiber Optic Internet), Large Separate Laundry, Sun Room, 2 Covered Porches, Deck, Fire Pit, 2 Car Garage, Barn/ Workshop... THE LIST GOES ON!

  Melissa Brown Keller Williams Legacy Group

  4455 Colby Rd, Winchester, KY 40391
• 

  

  /70

  Est $574,473 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,712 Sq Ft

  519 Right Angle Rd, Winchester, KY 40391

  519 Right Angle Rd, Winchester, KY 40391
• 

  

  /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
• 

  

  /32

  $263,000 Sold Sep 05, 2025

  • 1,397 Sq Ft
  • $188/SF
  • 2 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1960

  2 Chickadee Ln, Winchester, KY 40391

  Beautifully updated 1,397 sq ft ranch-style home with modern upgrades throughout! This move-in ready property features a new roof, HVAC, water heater, gutters, and fresh landscaping. The exterior has been freshly painted, including the back deck, and the driveway and sidewalk have been pressure washed. Inside, you'll find all-new flooring and fresh paint throughout. The kitchen features updated

  Ashley Spencer Keller Williams Commonwealth

  2 Chickadee Ln, Winchester, KY 40391
• 

  

  /69

  Est $408,712 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,021 Sq Ft

  3975 Wills Rupard Rd, Winchester, KY 40391

  3975 Wills Rupard Rd, Winchester, KY 40391
• 

  

  /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
• 

  

  /55

  $174,900 Sold Sep 05, 2025

  • 1,222 Sq Ft
  • $143/SF
  • 26 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1988

  20 Heather Ln, Winchester, KY 40391

  This charming 2-bedroom, 1.5-bath brick townhome offers a comfortable living space in a prime location. Inside, you'll find all-new LVP flooring, fresh carpet, and a fresh coat of paint throughout. The spacious living room flows into a well-sized kitchen featuring brand-new countertops and ample counter space—perfect for everyday cooking and entertaining.Appliances including the washer,

  Josh Wood Freedom Realty & Property Management

  20 Heather Ln, Winchester, KY 40391
• 

  

  /45

  Est $240,963 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 750 Sq Ft

  2240 Crowe Ridge Rd, Winchester, KY 40391

  2240 Crowe Ridge Rd, Winchester, KY 40391
• 

  

  /24

  $340,000

  • 4 Beds
  • 2.5 Baths
  • 2,008 Sq Ft

  118 Strawberry Ln, Winchester, KY 40391

  Welcome Home!Kick back and relax on either the covered front porch or the spacious back patio of this charming 4-bedroom, 2.5-bath home. Perfectly positioned in a prime, central location. Just a short drive to Lexington, and only minutes from shopping, dining, schools, the hospital, and easy access to I-64 and the bypass, this home offers the perfect blend of comfort and

  Susan Baldwin Rector Hayden Realtors

  118 Strawberry Ln, Winchester, KY 40391
• 

  

  /64

  $929,000 Sold Sep 05, 2025

  • 2,670 Sq Ft
  • $348/SF
  • 23 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2025

  1110 Craig Crossing, Winchester, KY 40391

  Discover timeless elegance and modern luxury in this newly constructed residence, perfectly situated on over 2.5 acres in Winchester. With 2,670 sq ft of custom designed living space, this 4-bedroom, 2.5-bath home offers craftsmanship, high-end finishes, and exceptional outdoor living. White oak engineered hardwood flooring, moulding throughout, and exquisite details. The spacious great room

  Michael Hilario The Agency

  1110 Craig Crossing, Winchester, KY 40391
• 

  

  /45

  Est $409,040 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,846 Sq Ft

  1600 Crowe Ridge Rd, Winchester, KY 40391

  1600 Crowe Ridge Rd, Winchester, KY 40391
• 

  

  /58

  $350,000

  • 4 Beds
  • 2.5 Baths
  • 2,179 Sq Ft

  205 Chardonnay Ct, Winchester, KY 40391

  This charming 4-bedroom, 2.5-bath home with a classic white picket fence sits on a quiet cul-de-sac in Fontaine Estates. Inside, the versatile layout offers space for every occasion—a formal dining room for special gatherings, a bright sunroom for morning coffee, a comfortable living room, and a cozy family room featuring a masonry fireplace with built-ins. The eat-in kitchen is perfect for

  Janna Smith United Real Estate Bluegrass

  205 Chardonnay Ct, Winchester, KY 40391
• 

  

  /16

  $201,000 Sold Sep 05, 2025

  • 1,526 Sq Ft
  • $132/SF
  • 66 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1930

  128 Alabama St, Winchester, KY 40391

  Charm meets convenience in this delightful newly renovated home! Experience city living at its finest with the tranquility of your own spacious backyard, yet be within walking distance to shops and restaurants! Step inside the living room and let the natural light peeking through the large windows welcome you home. With a bedroom on the main floor, two bedrooms upstairs, and a bonus room that

  Paul Eads Woods Realty Group

  128 Alabama St, Winchester, KY 40391
• 

  

  /56

  Est $642,764 Not Listed For Sale

  • 6 Beds
  • 2.5 Baths
  • 3,800 Sq Ft

  9953 Ironworks Rd, Winchester, KY 40391

  9953 Ironworks Rd, Winchester, KY 40391
• 

  

  /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
• 

  

  /31

  $485,000 Sold Sep 05, 2025

  • 3,262 Sq Ft
  • $149/SF
  • 11 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1906

  10 French Ave, Winchester, KY 40391

  Remember when things were built to last? This home was built in 1906 and recently underwent a complete renovation to bring this 118 year old home into the 21st century. The owners maintained all of the architectural details while adding the modern luxuries of today. Improvements made to the home consist of new dimensional shingle roof, gutters, soffits rebuilt including rebuilding the decorative

  Brian England Keller Williams Bluegrass Realty

  10 French Ave, Winchester, KY 40391
• 

  

  /45

  Est $304,004 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 300 Sq Ft

  9680 Ironworks Rd, Winchester, KY 40391

  9680 Ironworks Rd, Winchester, KY 40391
• 

  

  /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
• 

  

  /27

  $210,000 Sold Sep 04, 2025

  • 1,150 Sq Ft
  • $183/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1999

  305 Geronimo Ct, Winchester, KY 40391

  Welcome home to this beautifully appointed 3-bedroom, 2-bathroom residence designed for style and comfort. Step inside to a bright, open-concept living space featuring brand-new stainless steel appliances, complemented by luxurious granite and marble backsplash in the gourmet kitchen—perfect for culinary enthusiasts. Entertain or unwind on the expansive front and back decks, ideal for morning

  Aaron Kendall Lifstyl Real Estate

  305 Geronimo Ct, Winchester, KY 40391

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