184

Winchester, KY Homes for Sale

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  • /12

    $345,000

    • 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.

    Brian Hatfield Coldwell Banker McMahan

    1128 Dale Dr, Winchester, KY 40391
  • /34

    $275,700

    • 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 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 and friends. The sellers added fiber optics

    Craig Bridgewater Bridgewater Real Estate

    404 Wellington Way, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    155 Duclair Dr, 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

    155 Duclair 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
  • /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
  • /2

    $110,000

    • Land
    • 0.32 Acre
    • $343,750 per Acre

    135 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

    135 Jacob 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
  • /27

    $72,500

    • 3 Beds
    • 2 Baths
    • 1,128 Sq Ft

    725 Berry Ct, Winchester, KY 40391

    Looking for affordable homeownership in Winchester, KY? This move-in ready 3-bedroom, 2-bath manufactured home offers modern living at an incredible value. Built just 3 years ago and meticulously maintained, this home feels like new from the moment you step inside. Located in the heart of Winchester, you'll enjoy easy access to local restaurants, shopping, grocery stores, parks, and everyday

    Christa Joynt Keller Williams Commonwealth

    725 Berry Ct, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.32 Acre
    • $343,750 per Acre

    115 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

    115 Jacob Ct, Winchester, KY 40391
  • /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

    $160,000

    • 2 Beds
    • 1 Bath
    • 1,088 Sq Ft

    233 E Washington St, Winchester, KY 40391

    Welcome to 233 E. Washington Street, a charming ranch-style home offering comfort, space, and convenience in the heart of Winchester. The Roof, Windows and HVAC are updated. This 2-bedroom, 1-bath residence features an open-concept layout designed for easy living and everyday functionality. LVP flooring runs throughout the home, providing a clean, modern look that's both durable and low

    Lukas Owens The Brokerage

    233 E Washington St, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.5 Acre
    • $220,000 per Acre

    260 Duclair Dr, 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

    260 Duclair Dr, Winchester, KY 40391
  • /55

    $419,900

    • 5 Beds
    • 3.5 Baths
    • 2,564 Sq Ft

    6504 Combs Ferry Rd, Winchester, KY 40391

    PRICE IMPROVEMENT PLUS SELLERS ARE OFFERING UP TO $7,500 TOWARD BUYERS CLOSING COSTS, PREPAIDS OR RATE BUYDOWN. Welcome to an extraordinary residence where luxury, craftsmanship, and natural beauty come together. This house has been taken down to the studs, and thoughtfully rebuilt. This two story home with a walk-out basement sits on 8 acres, adjoining the Lower Howard Creek Preserve, offering

    Lucy Martin Jenkins United Real Estate Bluegrass

    6504 Combs Ferry Rd, Winchester, KY 40391
  • /27

    $175,000

    • 3 Beds
    • 2 Baths
    • 1,305 Sq Ft

    6 Monroe Ave, Winchester, KY 40391

    Charming Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a 3-bedroom, 2-bath home full of character and modern touches. Step inside to find an inviting family room with an updated shiplap fireplace surround, perfect for cozy evenings. The kitchen is filled with natural light and features granite countertops, making it both stylish and functional. Recent updates include an HVAC system

    Lindsey Bivens Berkshire Hathaway de Movellan Properties

    6 Monroe Ave, Winchester, KY 40391
  • /53

    $265,000

    • 2 Beds
    • 2 Baths
    • 1,521 Sq Ft

    174 Hidden Grove Ln, Winchester, KY 40391

    Welcome home to your Kentucky River retreat! This freshly remodeled 2-bedroom, 2-bath charmer offers two inviting covered decks with beautiful river views, a fenced yard for pets or play and even a personal lift for easy access. Inside, enjoy warm, modern updates, with a bright open floor plan. All new flooring, kitchen, baths and much more! Perfect for full-time living or a peaceful getaway just

    Kathryn Cheuvront Coldwell Banker McMahan

    174 Hidden Grove Ln, Winchester, KY 40391
  • /4

    $10,000

    • Land
    • 0.17 Acre
    • $58,824 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
  • /7

    $150,000

    • Land
    • 4.21 Acres
    • $35,629 per Acre

    1030 Craig Crossing Rd, Winchester, KY 40391

    Lot # 14 contains 4.21 acres of gently rolling land with small stream 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

    1030 Craig Crossing Rd, Winchester, KY 40391
  • /14

    $159,900

    • Land
    • 2.66 Acres
    • $60,113 per Acre

    590 Craig Crossing, Winchester, KY 40391

    Don't let this opportunity pass you by again. This prime lot in Thoroughbred Estates is back on the market due to Current owners change of plans. This lot is ready for your new home with a beautiful setting and located close to Winchester and Lexington in a new Luxury Subdivision. Watch the sun set each night from your rear deck or pool. Call today!!!

    Keith Wilson Coldwell Banker McMahan

    590 Craig Crossing, Winchester, KY 40391
  • /2

    $78,500

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

    Lot 3 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 3 Plantations Dr, Winchester, KY 40391
  • /34

    $235,000

    • 3 Beds
    • 2 Baths
    • 1,050 Sq Ft

    12 Linden Ave, Winchester, KY 40391

    Cute ranch with easy access to I-64 and downtown Winchester. Walk to the breweries, shopping and restaurants. 3 bedrooms with 2 full baths with 1 car detached garage with fenced in back yard. This property has a interesting feature of a building that's 14 x 40 that has been a rental but can be used as storage or a mother in-law suite.

    Roni Porter RE/MAX Creative Realty

    12 Linden Ave, 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
  • /60

    $279,950

    • 4 Beds
    • 3 Baths
    • 2,112 Sq Ft

    115 Watercrest Cir, Winchester, KY 40391

    Stunning Home in One of the Area's Most Coveted Neighborhoods!Experience spacious living with 3 generous bedrooms and 2 full baths on the main level, designed for comfort and everyday convenience. The walkout basement offers even more space with a large bedroom and an additional full bath, ideal for guests, extended family, or a private retreat. What truly sets this home apart? The sellers are

    Darrell Tackett Dream Maker Realty, LLC

    115 Watercrest Cir, Winchester, KY 40391
  • /13

    $400,000

    • Land
    • 2.19 Acres
    • $182,648 per Acre

    145 Codella Dr, Winchester, KY 40391

    Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

    Greg Leveridge Block + Lot Real Estate

    145 Codella Dr, Winchester, KY 40391
  • /2

    $100,000

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

    100 Duclair Dr, 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

    100 Duclair Dr, Winchester, KY 40391
  • /59

    $820,000

    • 2 Beds
    • 1.5 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
  • /2

    $110,000

    • Land
    • 0.29 Acre
    • $379,310 per Acre

    160 Duclair Dr, 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

    160 Duclair Dr, Winchester, KY 40391
  • /14

    $240,000

    • 3 Beds
    • 2.5 Baths
    • 2,380 Sq Ft

    10 Upper St, Winchester, KY 40391

    Modern Ranch residence full un-finished basement, large lot.

    E. Clark Toleman Real Estate Appraisal Services

    10 Upper St, Winchester, KY 40391
  • /3

    $645,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,526 Sq Ft

    106 Bella Shae Way, Winchester, KY 40391

    Welcome Home to the Claiborne Floor Plan by CP Builders. This stunning 4-bedroom, 2.5-bathroom home offers a luxurious and spacious living experience. The first floor features a magnificent primary suite complete with a spacious ensuite bathroom, a walk-in closet, and direct access to the backyard. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and

    Shane Underwood Keller Williams Commonwealth

    106 Bella Shae Way, Winchester, KY 40391
  • /9

    $206,000

    • Land
    • 7.77 Acres
    • $26,512 per Acre

    368 Flanagan Station Rd, Winchester, KY 40391

    Build your dream retreat on this beautiful 7.77-acre parcel nestled in a peaceful rural setting just outside Winchester. The gently rolling terrain provides a serene backdrop for your custom home, hobby farm, or equestrian space, offering plenty of room to roam, garden, or simply enjoy the privacy. With easy access from Flanagan Station Road, this property combines a quiet country feel with

    Shari Frasure Keller Williams Commonwealth

    368 Flanagan Station Rd, Winchester, KY 40391
  • /6

    $388,000

    • 5 Beds
    • 3 Baths
    • 2,762 Sq Ft

    101 E Lexington Ave, Winchester, KY 40391

    Here's your chance to own a nice investment property. This triplex has a 2 bed 1 bath unit, 2 bed 1 bath unit, and a 1 bed 1 bath unit. 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

    101 E Lexington Ave, Winchester, KY 40391
  • /21

    $189,500

    • 2 Beds
    • 2.5 Baths
    • 1,197 Sq Ft

    109 Quail Ridge Rd, Winchester, KY 40391

    Move-In Ready Brick Townhome with Garage and Fireplace Step into this charming brick townhome offering comfort, style, and convenience in every detail. The spacious living room features a cozy fireplace, soft neutral tones, and natural light that make it easy to feel at home. The open layout flows to the kitchen and dining area, creating the perfect setting for everyday living or entertaining

    Kim Dice EXP Realty, LLC

    109 Quail Ridge Rd, Winchester, KY 40391
  • /41

    $575,000

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

    2100 Stoner-Ephesus Rd, Winchester, KY 40391

    Beautiful 44.21 acre farm has so much to offer. The main residence features 2 spacious bedrooms and 2 full bathrooms, offering inviting living spaces and peaceful views of the surrounding countryside. The separate guest quarters has 1 bedroom and 1 bathroom and is ideal accommodations for visitors, extended family or staff. You will appreciate the thoughtfully designed facilities, including two

    Kelly Nisbet Coldwell Banker McMahan

    2100 Stoner-Ephesus Rd, Winchester, KY 40391
  • /84

    $849,900

    • 4 Beds
    • 3.5 Baths
    • 4,922 Sq Ft

    2509 Mount Sterling Rd, Winchester, KY 40391

    Embrace Bluegrass living with this beautiful fieldstone ranch on 10+ acres in the heart of horse country. Just minutes from interstate access, yet surrounded by rolling hills and scenic views, this mini farm offers a larger barn with 6 stalls, including water and electric connection, 90 foot roof hangover on the barn, 5 paddocks, each with their own gate and water ran along each paddock. The home

    Josh Wood Freedom Realty & Property Management

    2509 Mount Sterling Rd, Winchester, KY 40391
  • /11

    $249,000

    • 3 Beds
    • 2 Baths
    • 1,534 Sq Ft

    646 Laura Dr, Winchester, KY 40391

    Three bedrooms ranch, that has been updated with a new kitchen, with granite tops ,new appliances, new flooring ,new interior paintiing ,plus much more, located in Verna Hills S/D located between Winchester and Lexington . Owner/Agent

    Garry Milton Milton and Associates Real Estate

    646 Laura Dr, Winchester, KY 40391
  • /12

    $188,900

    • 3 Beds
    • 2 Baths
    • 1,116 Sq Ft

    41 7th St, Winchester, KY 40391

    Welcome to 41 7th Street. This brick ranch offers 3 bedrooms, 2 full baths, and hardwood floors throughout the living room, hallway, and bedrooms, ready to be refreshed with a re-sand and polish. The layout provides a foundation for a buyer looking to add personal updates and make it their own. Located at the end of the street, the home offers added privacy along with peaceful farm views behind

    Austina Bruton Re/Max Elite Realty - Hamburg

    41 7th St, Winchester, KY 40391
  • /30

    $259,900

    • 4 Beds
    • 1.5 Baths
    • 1,405 Sq Ft

    6 Hart Ave, Winchester, KY 40391

    Welcome to 6 Hart Avenue in Winchester, Kentucky — a home that just feels right from the moment you pull up. This well-maintained tri-level offers 4 bedrooms, 1.5 baths, and a smart layout that gives everyone room to spread out while still feeling connected. The tri-level design creates natural separation of space — perfect for busy households, guests, or a dedicated home office. Rich hardwood

    Joshua Warren Freedom Realty & Property Management

    6 Hart Ave, Winchester, KY 40391
  • /12

    $110,000

    • 3 Beds
    • 1.5 Baths
    • 1,260 Sq Ft

    400 Wexford Dr, Winchester, KY 40391

    Welcome! This home offers a practical layout with 3 bedrooms and 1.5 baths on a manageable 0.2-acre lot. The interior has been well maintained, and fenced backyard creates a private outdoor space ideal for gatherings, pets, or future improvements. A detached 2-car garage provides secure parking and storage. Approximately 5 minutes to downtown Winchester and 15 minutes to Lexington, positioning

    Katie Allen Keller Williams Legacy Group

    400 Wexford Dr, Winchester, KY 40391

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