172

Winchester, KY Homes for Sale

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  • /22

    $221,500

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft

    443 Jameson Way, Winchester, KY 40391

    This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

    Tyler I Back The Brokerage

    443 Jameson Way, Winchester, KY 40391
  • /28

    $309,900

    • 3 Beds
    • 3.5 Baths
    • 2,526 Sq Ft

    24 N Burns Ave, Winchester, KY 40391

    Historic charm with all the modern amenities! An inviting front porch and entry lead to a welcoming space warmed by refinished original hardwood floors and a new electric fireplace. Other updates include a brand-new kitchen with granite countertops and new appliances, new lighting fixtures, tile in the foyer and bathrooms, new roof, new plumbing, new electrical, new HVAC, new windows, new spray

    Sarah Hess Keller Williams Commonwealth

    24 N Burns Ave, Winchester, KY 40391
  • /36

    $434,500

    • 4 Beds
    • 2.5 Baths
    • 2,747 Sq Ft

    134 Fontaine Blvd, Winchester, KY 40391

    Some homes are just houses—but this one was built for connection, creativity, and meaningful moments. Located in the desirable Oak Hill neighborhood, just minutes from GRC High School, this meticulously maintained 4-bedroom, 2.5-bath home offers the space and flexibility today's families are looking for. Formerly home to the beloved "2 Momma's Cooking for You," the property features a fully

    Craig Bridgewater Bridgewater Real Estate

    134 Fontaine Blvd, Winchester, KY 40391
  • /29

    $262,500

    • 3 Beds
    • 2 Baths
    • 1,192 Sq Ft

    410 Wellington Way, Winchester, KY 40391

    Discover 410 Wellington Way, a beautifully updated property in a convenient Winchester location! This fully updated, move-in-ready home delivers style, comfort, and convenience from the moment you walk in. Enjoy a bright eat-in kitchen equipped with brand-new, warrantied appliances, plus modern finishes throughout—including all-new paint, new flooring, new light fixtures, new doors, updated

    Monica Marcum Century 21 Pinnacle

    410 Wellington Way, Winchester, KY 40391
  • /14

    $129,800

    • Land
    • 2.3 Acres
    • $56,435 per Acre

    110 Knox Ct, Winchester, KY 40391

    The largest and most desirable lot in The Reserve is now available! Nestled in a cul-de-sac, this 2.3 acre tract offers exceptional views of Bluegrass farmland. Build your custom dream home and watch the sun set over the pond, right from your porch. Located in one of Winchester's newest luxury subdivisions, featuring carefully crafted guidelines to preserve the community's character. All of this

    Amanda Thomas The Agency

    110 Knox Ct, Winchester, KY 40391
  • /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
  • /3

    $430,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,855 Sq Ft

    220 Evergreen Dr, Winchester, KY 40391

    Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private

    Rex Hall United Real Estate Bluegrass

    220 Evergreen Dr, Winchester, KY 40391
  • /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
  • /15

    $925,000

    • Land
    • 3.77 Acres
    • $245,358 per Acre

    300 Rolling Hills Ln, Winchester, KY 40391

    Great location just off exit 96 on I-64 and easy access to the Mountain Parkway. Only 15 minutes from I-75. Located near the entrance to the Winchester Kentucky Industrial Park. 3.774 flat acres to build your next business location.

    Josh Wood Freedom Realty & Property Management

    300 Rolling Hills Ln, Winchester, KY 40391
  • /58

    $525,000

    • 2 Beds
    • 1.5 Baths
    • 5,054 Sq Ft

    808 Bypass Rd, Winchester, KY 40391

    Unique Mixed-Use Opportunity! This versatile property offers prime potential for a restaurant, café, or retail space in a high-visibility location. The commercial space is turn key for a culinary venture or boutique business. Attached is a separate rental unit with private entrance, offering additional income or an ideal live/work setup. Additional space available for potential 2nd Apartment.

    Diana C Brooker Lifstyl Real Estate

    808 Bypass Rd, Winchester, KY 40391
  • /13

    $252,500

    • 5 Beds
    • 3 Baths
    • 3,007 Sq Ft

    221 S Highland St, Winchester, KY 40391

    INVESTOR SPECIAL, could be a great option for an end of year cost seg study and bonus depreciation. You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in

    Joshua Lynch The Brokerage

    221 S Highland St, Winchester, KY 40391
  • /42

    $349,900

    • 3 Beds
    • 3 Baths
    • 2,821 Sq Ft

    3622 Stamper Dr, Winchester, KY 40391

    This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. Properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming laminate floors and a brick fireplace; the perfect place to

    Josh Wood Freedom Realty & Property Management

    3622 Stamper Dr, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.27 Acre
    • $407,407 per Acre

    125 Jacob Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    125 Jacob Ct, Winchester, KY 40391
  • /21

    $440,000

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

    870 Pilot View Rd, Winchester, KY 40391

    Welcome to your own slice of paradise! This 2022 doublewide sits on an impressive 39.5 acres of rolling countryside in Winchester, offering the perfect blend of modern comfort, privacy, and wide-open space. Step outside and take in the beautiful pastures, ideal for horses, cattle, or hobby farming, all complemented by a peaceful creek that winds through the property—perfect for relaxing evenings

    Chelsea Morguson McCallie Real Estate

    870 Pilot View Rd, Winchester, KY 40391
  • /8

    $195,000

    • Land
    • 6.15 Acres
    • $31,707 per Acre

    990 Craig Crossing Rd, Winchester, KY 40391

    Lot # 13 contains 6.153 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

    Keith Wilson Coldwell Banker McMahan

    990 Craig Crossing Rd, Winchester, KY 40391
  • /2

    $78,500

    • Land
    • 0.22 Acre
    • $356,818 per Acre

    Lot 5 Plantations Dr, Winchester, KY 40391

    NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

    Melia Hord Keller Williams Legacy Group

    Lot 5 Plantations Dr, Winchester, KY 40391
  • /6

    $49,500

    • Land
    • 0.98 Acre
    • $50,510 per Acre

    204 Wigeon Ct, Winchester, KY 40391

    Choose your preferred builder to construct your dream home in Mallard Place. Located in a quiet cul-de-sac at the rear of the subdivision. Only a 20 minute drive to Hamburg/Lexington and only a 5 minute drive to the Winchester Bypass. Enjoy the serenity of living in a private setting AND the convenience of being close to schools, shopping and I-64 and I-75.

    Jim Woodrum RE/MAX Creative, Winchester

    204 Wigeon Ct, Winchester, KY 40391
  • /34

    $260,000

    • Land
    • 6.08 Acres
    • $42,763 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
  • /24

    $275,000

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    120 Sunset Heights, Winchester, KY 40391

    Your search is over with this hard to find 3 bedroom 2 bathroom ranch located close to town, College Park and featured a nice fenced level yard. Your will love the cathedral ceiling in the Great Room and Kitchen as well as the above ground pool with a new liner ready to be installed. You will love the oversized rear deck which will be great for entertaining. A covered front porch as well as

    Keith Wilson Coldwell Banker McMahan

    120 Sunset Heights, Winchester, KY 40391
  • /35

    $349,000

    • 4 Beds
    • 3 Baths
    • 2,100 Sq Ft

    121 Fitch Ave, Winchester, KY 40391

    *Under contract with a 48-hour kick out clause. Please continue to show and bring offers* This beautifully updated 4-bedroom, 3-bath ranch home includes a private mother-in-law suite, offering flexible living options for guests or extended family. With 2,100 square feet of inviting living space and an attached two-car garage, this home perfectly combines timeless charm with thoughtful modern

    Ashley Spencer Keller Williams Commonwealth

    121 Fitch Ave, Winchester, KY 40391
  • /24

    $290,000

    • 12 Beds
    • 4 Baths
    • 4,010 Sq Ft

    149 Winn Ave, Winchester, KY 40391

    Welcome to this quad plex income producing property. It is a large lot and the property sits back on the lot away from the road. There are 4 units, each with 3 beds and 1 bath. The whole building has a total of bedrooms of 12 beds and 4 baths. Each unit has its own kitchen. The pictures are of the only vacant unit on the bottom left. The two lower units rent for $950 and $925. The upper units

    Libby VanMeter Marshall Lane Real Estate - Lexington

    149 Winn Ave, Winchester, KY 40391
  • /49

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 2,258 Sq Ft

    233 Cunningham Ln, Winchester, KY 40391

    Mini Farm Alert! This fabulous homestead is located less than 2 miles off the Mountain Parkway making it easily accessible. One level, ranch home that features 3 bedrooms, a luxurious primary ensuite... corner jetter tub, seperate walk in shower with glass door, double bowl raised height vanity and a linen closet complete the bathroom and the bedroom has vaulted ceilings, walk in closet and

    Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

    233 Cunningham Ln, Winchester, KY 40391
  • /3

    $146,000

    • 3 Beds
    • 1 Bath
    • 1,020 Sq Ft

    228 Jackson St, Winchester, KY 40391

    Here's your chance to own a nice investment property. This single family home has a 3 bed 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

    David Espinosa Bluegrass Realty Pros, Inc

    228 Jackson St, Winchester, KY 40391
  • /4

    $115,000

    • 4 Beds
    • 2.5 Baths
    • 2,131 Sq Ft

    205 E Washington St, Winchester, KY 40391

    PRICE DROP!!! FLIP This House! Seller Has Added A Large Primary Addition And Front Porch. This 4 Bedroom 2 1/2 Bath Home Is Ready For Your Finishes And Has A Fantastic Floor Plan With Large Loft (Whole Home At Stud Level). Finish This Home It Will Be A Showstopper Better Than New Construction With Large Sq Ft What Many Buyers Are Looking For. Great Opportunity To Make Money Or Live In This

    Patrick Arvin Keller Williams Commonwealth

    205 E Washington St, Winchester, KY 40391
  • /18

    $99,000

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft

    114 Magnolia St, Winchester, KY 40391

    Great opportunity for investors, flippers, or anyone looking for a project with tons of potential! This 2 bedroom, 1 bath home features a 2 year old roof, giving you a solid head start on future updates. With its convenient location and plenty of possibilities, this property is ready for someone to bring their vision! Selling as is. Cash or conventional financing only.

    Michelle Blackburn RE/MAX Creative, Winchester

    114 Magnolia St, Winchester, KY 40391
  • /4

    $199,900

    • Land
    • 11.36 Acres
    • $17,597 per Acre

    2996 Irvine Rd, Winchester, KY 40391

    Are you looking to build your dream home in a quiet country setting with easy access to the Interstate? Look no further! This property offers it all! Gorgeous setting with the best views and creek access. This lovely farm is 11.36 acres of gently rolling country land, in a highly desirable area with easy access to interstate 64, the Mountain Parkway and Hamburg. No city sewage. Deed restrictions

    Lura Justice Rector Hayden Realtors

    2996 Irvine Rd, Winchester, KY 40391
  • /9

    $1,350,000

    • Land
    • 3.02 Acres
    • $447,020 per Acre

    155 April Way, Winchester, KY 40391

    Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided.Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One,

    Greg Leveridge Block + Lot Real Estate

    155 April Way, Winchester, KY 40391
  • /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
  • /34

    $279,700

    • 3 Beds
    • 2 Baths
    • 1,682 Sq Ft

    404 Wellington Way, Winchester, KY 40391

    This house is located minutes from the Winchester Bypass and within walking distance of the new Clark County Pre-school. The house features 3 bedrooms and 2 full baths. The kitchen is open to a large dining area. The kitchen is supplied with all the appliances. And the house also has a washer and dryer. The large great room is perfect for watching the favorite sports teams and movies with family

    Craig Bridgewater Bridgewater Real Estate

    404 Wellington Way, Winchester, KY 40391
  • /41

    $318,000

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

    118 Windridge Dr, Winchester, KY 40391

    Start off the new year in a new home! Imagine spending summers in your own private backyard retreat, complete with an in-ground pool featuring a newer liner, pump, and filter, secure iron fencing, and a roomy concrete patio that's ideal for relaxing or entertaining. This well-cared-for brick ranch in Windridge offers 3 bedrooms, 2 full baths, and hardwood and tile floors throughout with no

    Michelle Blackburn RE/MAX Creative, Winchester

    118 Windridge Dr, Winchester, KY 40391
  • /47

    $499,000

    • 5 Beds
    • 3.5 Baths
    • 3,823 Sq Ft

    595 Earlymeade Dr, Winchester, KY 40391

    Entertaining the idea of entertaining family and friends? Looking for space for living the good life in a fun house in a great neighborhood? Then look no further. This house is ready for you to make it your new home. Located in the desirable neighborhood of Earlymeade, this house is minutes from the Winchester Bypass, I- 64 corridor and the Hamburg area of Lexington. Along with 5 bedrooms and 3.5

    Craig Bridgewater Bridgewater Real Estate

    595 Earlymeade Dr, Winchester, KY 40391
  • /15

    $600,000

    • 8 Beds
    • 4 Baths
    • 5,046 Sq Ft

    101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391

    Step into a rare investment opportunity in the heart of downtown Winchester! This beautifully renovated 4-plex offers charm, space, and convenience — all within a fully restored historic building. Each of the four spacious units boasts approximately 1,296 sq ft, blending timeless character with modern updates. The entire property has been thoughtfully renovated in 2021, including a brand-new

    Priya Patel-Rossetti Big Blue Realty

    101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391
  • /4

    $67,500

    • Land
    • 1.92 Acres
    • $35,156 per Acre

    12569 Ironworks Rd, Winchester, KY 40391

    Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Or hold as investment property and watch this land grow in value. This lot containing 1.919 acres, offer unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own

    Kathryn Cheuvront Coldwell Banker McMahan

    12569 Ironworks Rd, Winchester, KY 40391
  • /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
  • /13

    $74,900

    • Land
    • 2.14 Acres
    • $35,000 per Acre

    1751 Little Stoner Rd, Winchester, KY 40391

    Located at 1751 Little Stoner Rd in Winchester, this 2.139 acre building lot offers the kind of space and setting that's getting harder to find. Open land, rolling country views, and room to create something truly your own, all while staying conveniently connected to the places that matter most. Enjoy the rare balance of peaceful surroundings with easy access. You're just 20 minutes to Lexington,

    Kymberly McCreary EXP Realty, LLC

    1751 Little Stoner Rd, Winchester, KY 40391
  • /43

    $269,900

    • 7 Beds
    • 3 Baths
    • 3,393 Sq Ft

    146 W Lexington Ave, Winchester, KY 40391

    This investment property has strong rent potential to add to your portfolio. Property is conveniently located in the heart of Downtown Winchester and is zoned R-4. There's a great opportunity to use this property for house hacking -- leverage your money by living in one unit and renting out the other! Downstairs unit has 4 bedrooms and 2 full bathrooms, and its currently leased for $1,495 a

    Kevin Bradley KB Realty Group

    146 W Lexington Ave, Winchester, KY 40391
  • /70

    $335,000

    • 6 Beds
    • 4 Baths
    • 3,544 Sq Ft

    297 S Main St, Winchester, KY 40391

    Completely remodeled duplex offering over 3,400 sq. ft. of living space! Featuring 6 bedrooms and 4 bathrooms, this property has been fully updated with granite countertops, new appliances, fresh flooring, and paint throughout. The layout is bright and inviting with plenty of natural light. Enjoy the covered front porch, separate utility room, and unfinished basement for extra storage or future

    Silvia Torres Tru Life Real Estate

    297 S Main St, Winchester, KY 40391
  • /5

    $29,000

    • Land
    • 0.46 Acre
    • $63,043 per Acre

    102 Augusta Dr, Winchester, KY 40391

    This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

    Dale Hatton Dream Maker Realty, LLC

    102 Augusta Dr, 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
  • /62

    $259,500

    • 3 Beds
    • 2 Baths
    • 1,247 Sq Ft

    3614 Stamper Dr, Winchester, KY 40391

    Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

    Darrell Tackett Dream Maker Realty, LLC

    3614 Stamper Dr, Winchester, KY 40391

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