Winchester, KY Homes for Sale with Garage

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  /41

  $225,000

  $10K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,609 Sq Ft

  120 Windsor Dr, Winchester, KY 40391

  Nestled in a well-established neighborhood filled with charm and character, this inviting all-brick home offers the warmth and comfort you've been looking for. Featuring 4 bedrooms and 1 bath, the thoughtfully designed layout includes a primary bedroom and second bedroom on the main floor, with two additional bedrooms upstairs, providing flexibility for family, guests, or a home office. Beautiful

  Cathie Witt-Pyle Keller Williams Commonwealth

  120 Windsor Dr, Winchester, KY 40391
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  /32

  $320,000

  New Construction $30K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,310 Sq Ft

  38 N Burns Ave, Winchester, KY 40391

  Welcome to this beautiful BRAND 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

  Trina Penn RE/MAX Creative Realty

  38 N Burns Ave, Winchester, KY 40391
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  /20

  $316,900

  $100K PRICE INCREASE

  • 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
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  /32

  $175,000

  • 3 Beds
  • 1 Bath
  • 1,173 Sq Ft

  24 Spring St, Winchester, KY 40391

  Lovely one story home located minutes from downtown Winchester with large detached garage ans shed! This home as three bedrooms and one bath with covered porch and walled patio outside. The garage is equipped with large ares for parking and storage and also has its own kitchen. Don't let this one pass by. Come see TODAY!!! Note: This is an auction property. Please call agent for more info Buyer

  Jason Szaks EXIT Town & Country Realtors

  24 Spring St, Winchester, KY 40391
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  /120

  $1,595,000

  $100K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 4,518 Sq Ft

  3166 Colby Rd, Winchester, KY 40391

  NEW PRICE!!! Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points

  Alyssa M Boley Coldwell Banker McMahan

  3166 Colby Rd, Winchester, KY 40391
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  /26

  $234,900

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

  528 Estes Dr, Winchester, KY 40391

  *NEW ROOF!* Welcome home to this well-maintained 3-bedroom, 2-bath brick ranch offering easy one-level living in a convenient location close to shopping, dining, parks, and the community pool. The spacious open family room flows into the kitchen, featuring bamboo wood flooring, a large granite island, newer stainless steel appliances, and a gas range—perfect for everyday living and entertaining.

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
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  /110

  $724,889

  • 4 Beds
  • 4.5 Baths
  • 4,255 Sq Ft

  132 Lana Ln, Winchester, KY 40391

  This gorgeous home is a rare find. Perfect for anyone looking for a spacious home with room to grow. The beautiful sunroom overlooks the luxurious in-ground salt water pool. Inside the home you'll find over 4,000 square feet of easy living. A beautiful kitchen with a breakfast nook and bar top, a formal dining area, large living room, a family room with a fireplace, spacious bedrooms, and a

  Rebecca Harvey Napier Realtors

  132 Lana Ln, Winchester, KY 40391
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  /52

  $429,000

  $36K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,942 Sq Ft

  1024 Flanagan Station Rd, Winchester, KY 40391

  Nestled on 8.9 picturesque acres just off Boonesboro Road, this one-of-a-kind property offers the perfect blend of character, privacy, and endless potential. Whether you're dreaming of a horse farm, hobby farm, or simply room to roam, this beautiful property provides plenty of space for horses, livestock, gardening, or enjoying peaceful country living. Inside, you'll find a spacious open-concept

  Brooke Martin RO&CO Real Estate

  1024 Flanagan Station Rd, Winchester, KY 40391
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  /30

  $140,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 630 Sq Ft

  108 Franklin Ave, Winchester, KY 40391

  Property includes a detached secondary structure, a 600 sq. ft., 1-bedroom, 1-bath. This structure offers potential for investment use. Property and secondary structure are being sold as-is. Buyer and buyer's agent to independently verify square footage, zoning, permitted use, occupancy requirements, and suitability for buyer's intended purpose.

  Cheri Shaffer Lifstyl Real Estate

  108 Franklin Ave, Winchester, KY 40391
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  /50

  $249,900

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  215 Robyn Dr, Winchester, KY 40391

  Welcome home to this beautifully updated property offering modern finishes, a functional layout, and a fantastic location! Major improvements include an updated HVAC system, water heater, roof, windows, doors, lighting, flooring, fresh paint and more, giving the next owner plenty to appreciate from day one. Inside, the open kitchen and living area creates an inviting space for everyday living and

  Josh Wood Freedom Realty & Property Management

  215 Robyn Dr, Winchester, KY 40391
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  /74

  $489,000

  • 4 Beds
  • 3.5 Baths
  • 3,584 Sq Ft

  1137 Lafayette Blvd, Winchester, KY 40391

  Welcome home to this 4 bedroom, 3.5 bathroom home offering plenty of room to spread out. The open kitchen and living room create a comfortable gathering space, while a separate dining room provides additional space for meals and entertaining. The fully finished basement offers even more living space, including a room with a closet that could provide flexibility for a home office, hobby room or

  Brittany Nester RO&CO Real Estate

  1137 Lafayette Blvd, Winchester, KY 40391
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  /29

  $50,000

  • 1 Bed
  • 1 Bath
  • 870 Sq Ft

  141 Coffee Springs Ln, Winchester, KY 40391

  This is a public auction. You are buying as/is. Please come and preview the property. 10% Buyers premium added to the final bid. 10% down night of the sell. This property can be made into a dream home. Where else can you find a property for 50,000.00 dollars? Rony Jo Ballou Auctioneer 859-595-6808 bid at www.goochsells.com. Realtors you are welcome to bring your clients to preview this property.

  Rony Jo Ballou Power House Realty

  141 Coffee Springs Ln, Winchester, KY 40391
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  /19

  $259,900

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 2,444 Sq Ft

  2379 Big Stoner Rd, Winchester, KY 40391

  SELLING "AS IS" Welcome to country living!! approximately 1 acre lot with 3-car garage. updates include; new basement doctor system, new range, refrigerator, dishwasher, and washer/dryer. New LVP flooring, new light fixtures inside and out. New septic system, new front storm door and new sliding glass door in dining room. New electric outlets and switch plates. New garage door on lower one car

  Melisa McDonald Wrenn Realty

  2379 Big Stoner Rd, Winchester, KY 40391
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  /25

  $235,500

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  125 Kittison Dr, Winchester, KY 40391

  Charming ranch home featuring 3 bedrooms, 1 full bath with a spacious layout and inviting curb appeal. Enjoy relaxing or entertaining on the covered back patio overlooking the large backyard with plenty of room for pets, play, or gardening. The kitchen offers beautiful granite countertops, ample cabinet space, and all appliances stay for added convenience. A wonderful opportunity for comfortable

  Kathryn Cheuvront Coldwell Banker McMahan

  125 Kittison Dr, Winchester, KY 40391
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  /37

  $219,000

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,261 Sq Ft

  14 Cook Ave, Winchester, KY 40391

  Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a

  Janna Chalfant Smith United Real Estate Bluegrass

  14 Cook Ave, Winchester, KY 40391
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  /27

  $279,500

  • 3 Beds
  • 2.5 Baths
  • 1,963 Sq Ft

  304 Newcastle Ln, Winchester, KY 40391

  This house is located within walking distance of Clark County Preschool, Strode Station and Baker and is within minutes of Winchester Bypass and I-64. The house has 3 bedrooms and 2.5 baths and a bonus room on the 2nd floor that would make a great game room or office. The bonus room would also make a nice 4th bedroom. The owner of the house has replaced all of the kitchen appliances and replaced

  Craig Bridgewater Bridgewater Real Estate

  304 Newcastle Ln, Winchester, KY 40391
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  /47

  $484,900

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,381 Sq Ft

  410 Fairholme Way, Winchester, KY 40391

  Modern luxury meets everyday living in this beautiful new construction ranch home in Winchester's Fairholme Estates- where thoughtful details, timeless finishes, and incredible golf course view sunsets come together effortlessly. Inside, an inviting open-concept layout features vaulted ceilings and a fireplace anchoring the spacious living room. The timeless kitchen is designed to be both

  Morgan Withrow The Brokerage

  410 Fairholme Way, Winchester, KY 40391
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  /65

  $359,900

  • 3 Beds
  • 2 Baths
  • 2,269 Sq Ft

  15 Moundale Ave, Winchester, KY 40391

  Welcome to this beautifully maintained all-brick home nestled in one of Winchester's most established and desirable neighborhoods. Offering over 2,200 square feet of finished living space, this 3-bedroom, 2-bath home combines timeless character with an impressive list of thoughtful updates. The main level features a spacious family room with ventless gas logs, a beautifully updated kitchen with

  Josh Wood Freedom Realty & Property Management

  15 Moundale Ave, Winchester, KY 40391
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  /63

  $785,000

  • 5 Beds
  • 2.5 Baths
  • 4,676 Sq Ft

  217 Wades Mill Rd, Winchester, KY 40391

  Escape to the peace and privacy of country living with this spacious brick one-and-a-half story home situated on just over 5 acres. With plenty of room to spread out, the main level offers a welcoming foyer, formal dining room, living room with a wood-burning fireplace, kitchen featuring granite countertops, tile backsplash, breakfast nook, and laundry room, along with the primary suite, three

  Michelle Blackburn RE/MAX Creative, Winchester

  217 Wades Mill Rd, Winchester, KY 40391
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  /62

  $309,900

  $20K PRICE DROP

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

  335 Newcastle Ln, Winchester, KY 40391

  Welcome to this well-maintained home located in a quiet, established neighborhood with convenient access to everything Winchester has to offer. The first floor features an open and inviting layout, creating a comfortable space for everyday living and entertaining alike. Upstairs, you'll find a traditional three-bedroom floor plan with generously sized bedrooms, including a spacious primary suite.

  Josh Wood Freedom Realty & Property Management

  335 Newcastle Ln, Winchester, KY 40391
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  /30

  $274,500

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft

  137 Eastridge Dr, Winchester, KY 40391

  Welcome to this delightful 1.5-story home perfectly situated on a spacious corner lot just off the Eastern Bypass and only minutes from I-64. Convenience meets comfort in this beautifully maintained property offering 3 bedrooms, 2 full baths, and an inviting layout designed for everyday living. Step inside to an open living area ideal for entertaining, a spacious kitchen and dining space, and

  Kathy Burton Coldwell Banker McMahan

  137 Eastridge Dr, Winchester, KY 40391
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  /4

  $625,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,405 Sq Ft

  424 Alexis Way, Winchester, KY 40391

  Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard Cove neighborhood. This exquisite floor plan features a side-turned garage and captivating curb appeal with double front entry doors. Inside, you'll find a thoughtfully designed split-bedroom layout with a spacious primary suite that includes a luxurious ensuite with a walk-in closet, double vanity, tile

  Shane Underwood Keller Williams Commonwealth

  424 Alexis Way, Winchester, KY 40391
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  /14

  $165,000

  $15K PRICE DROP

  • 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
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  /55

  $515,000

  $10K PRICE DROP

  • 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
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  /7

  $365,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft

  204 Jett Dr, Winchester, KY 40391

  New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

  Mila Ensor Ensor Real Estate, LLC

  204 Jett Dr, Winchester, KY 40391
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  /12

  $137,500

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  48 Judy Ann Ct, Winchester, KY 40391

  Affordable and inviting townhome conveniently located in Winchester! This well-maintained home offers a functional layout with a spacious kitchen featuring plenty of room for everyday cooking and dining. The main level includes a comfortable living room, convenient half bath, and access to a private patio, perfect for relaxing or enjoying your morning coffee. A dedicated storage area provides

  Holly Spradlin KY Realty Co

  48 Judy Ann Ct, Winchester, KY 40391
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  /19

  $295,000

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft

  405 Nick Ln, Winchester, KY 40391

  Come see this beautiful 13-acre property in the Historic Boonesborough area of Clark County, offering peaceful country living with the convenience of being just minutes from Winchester, Richmond, and Lexington. The property features a 2-bedroom, 1-bath home with 1,344 sq. ft., surrounded by beautiful acreage with plenty of room for animals, recreation, gardening, or simply enjoying the outdoors.

  Taylor Norton McCallie Real Estate

  405 Nick Ln, Winchester, KY 40391
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  /40

  $295,000

  $11K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,970 Sq Ft

  428 Waycross Dr, Winchester, KY 40391

  Wow! Pack your belongings and get ready to move! Your dream house just hit the market and It is going to go quick. Imagine sitting on the back deck , sipping your favorite beverage while your children and pets play safely in this large fenced in back yard. Or set up your home theatre in the spacious finished basement. This home has so much to offer, very spacious with the primary bed room and

  Wayne Elkins RE/MAX Creative Realty

  428 Waycross Dr, Winchester, KY 40391
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  /32

  $199,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  32 Jackson St, Winchester, KY 40391

  This beautiful home is located just minutes from historic downtown Winchester. It has 3 spacious bedrooms and 1 full bath. The home has a new roof. When you walk out back you will find an oversized garage. The huge backyard is all fenced in. Make an appointment to tour this one before it's gone.

  Dale Hatton Dream Maker Realty, LLC

  32 Jackson St, Winchester, KY 40391
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  /54

  $254,900

  • 3 Beds
  • 2.5 Baths
  • 1,664 Sq Ft

  127 Bay Hill Dr, Winchester, KY 40391

  Welcome home to this spacious, low-maintenance townhome offering 3 levels of living space in a well established neighborhood. Thoughtfully maintained, a 3 year old roof, with recently replaced windows. This home offers plenty of room to spread out while keeping everyday living comfortable and convenient. The main level features a generously sized kitchen and family room with plenty of space for

  Josh Wood Freedom Realty & Property Management

  127 Bay Hill Dr, Winchester, KY 40391
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  /12

  $239,000

  $116K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,072 Sq Ft

  1128 Dale Dr, Winchester, KY 40391

  Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

  Brian Hatfield Coldwell Banker McMahan

  1128 Dale Dr, Winchester, KY 40391
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  /3

  $825,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,995 Sq Ft

  111 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. Thespacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a

  Shane Underwood Keller Williams Commonwealth

  111 Bella Shae Way, 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 Homes

  4664 Lexington Rd, Winchester, KY 40391
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  /40

  $244,000

  • 3 Beds
  • 2 Baths
  • 1,692 Sq Ft

  54 Locust Dr, Winchester, KY 40391

  SHORT SALE OPPORTUNITY! 54 Locust Dr. is an all-brick ranch in Westland Park offering 3 bedrooms, 2 baths and 1,692 sq. ft. of finished living space, plus a full unfinished basement. The home features hardwood flooring, a 2-car attached garage, fenced backyard and covered patio. Previous owners completed structural work in the basement that includes a transferable lifetime warranty. The home

  Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  54 Locust Dr, Winchester, KY 40391
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  /23

  $204,900

  • 3 Beds
  • 1 Bath
  • 1,128 Sq Ft

  38 Mackay Ave, Winchester, KY 40391

  Beautiful 3-bedroom, 1-bath home located at the end of a quiet, well established neighborhood within walking distance to downtown Winchester. This home features hardwood floors, a versatile in home office or bonus room, and several recent upgrades including a new stove, microwave, refrigerator, cabinets, and HVAC (1 year old). The property offers a backyard with a storage shed, providing

  Nena Honaker Tom Goebel & Company

  38 Mackay Ave, Winchester, KY 40391
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  /4

  $635,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,537 Sq Ft

  422 Alexis Way, Winchester, KY 40391

  Introducing the Denver, a gorgeous all-brick ranch home offering 4 bedrooms and 2.5 baths, designed for both luxury and practicality. With its stunning curb appeal, front porch, and beam accents, this home makes a lasting first impression. Inside, the split-bedroom layout offers privacy and space for everyone, with a large primary suite featuring a walk-in closet, soaking tub, separate shower,

  Shane Underwood Keller Williams Commonwealth

  422 Alexis Way, Winchester, KY 40391
• 

  

  /27

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,108 Sq Ft

  227 Leslie Dr, Winchester, KY 40391

  This 3 Bedroom, 2 bath home is quietly nestled within the Saddle Brook subdivision. Conveniently located just outside of Winchester New Bypass, this property also qualifies for zero down rural housing financing. Updates can be seen throughout along with spacious master bedroom with on-suite, large back yard and open concept living. Schedule your showing today!

  Michael Hilario The Agency

  227 Leslie Dr, Winchester, KY 40391
• 

  

  /3

  $700,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  415 Alexis Way, Winchester, KY 40391

  Introducing the Merango, a classic all-brick ranch home designed for both comfort and style. With stunning double front doors and a 2-car attached garage, this home offers incredible curb appeal and modern living. The spacious 3-bedroom, 2-bath layout features a split-bedroom design for added privacy, along with a dedicated study perfect for a home office. The open-concept kitchen is ideal for

  Shane Underwood Keller Williams Commonwealth

  415 Alexis Way, Winchester, KY 40391
• 

  

  /52

  $539,000

  • 3 Beds
  • 2.5 Baths
  • 2,732 Sq Ft

  267 Runnymeade Dr, Winchester, KY 40391

  Welcome to this beautifully designed 3-bedroom, 2.5-bath ranch in the highly sought-after Earlymeade subdivision, where comfort, style, and exceptional efficiency come together. This spacious one-story home offers an open, inviting floor plan highlighted by a stunning floor-to-ceiling stone fireplace that anchors the expansive great room. The well-appointed kitchen features granite countertops,

  Jason Caudill RE/MAX Creative Realty

  267 Runnymeade Dr, Winchester, KY 40391
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  /58

  $724,950

  $100K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 2,361 Sq Ft

  455 Davis Ln, Winchester, KY 40391

  Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of

  Dale Hatton Dream Maker Realty, LLC

  455 Davis Ln, Winchester, KY 40391

Showing Results 41 - 80, Page 2 of 3