213

Winchester, KY Homes for Sale

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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
  • /25

    $260,000

    • 3 Beds
    • 2 Baths
    • 1,809 Sq Ft

    316 Maryland Ave, Winchester, KY 40391

    Brick ranch on a partially finished basement offering 3 bedrooms and 2 full baths! The main level welcomes you into a comfortable living room featuring a masonry wood-burning fireplace, along with a spacious kitchen, all three bedrooms, and a full bath located down the hall. The kitchen provides access to the basement where you'll find additional living space in the cozy den area complete with a

    Michelle Blackburn RE/MAX Creative, Winchester

    316 Maryland Ave, Winchester, KY 40391
  • /14

    $1,115,000

    • Land
    • 120 Acres
    • $9,292 per Acre

    345 Providence Ln, Winchester, KY 40391

    Possible option to purchase the full 202 acres! Rare opportunity to own approximately 120 acres of beautiful rolling farmland in Clark County! This versatile property offers a mix of cleared pasture and wooded acreage, ideal for cattle, horses, recreation, or your dream homestead. Including a large pond plus county water available at the road this property is well-suited for agricultural use. The

    Megan McCoy Keller Williams Legacy Group

    345 Providence Ln, Winchester, KY 40391
  • /14

    $180,000

    • 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
  • /55

    $525,000

    • 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
  • /14

    $269,900

    • 3 Beds
    • 1 Bath
    • 1,644 Sq Ft

    205 Providence Ln, Winchester, KY 40391

    You Wont Find A More Beautiful And Private Setting!!! This Home Features 3 Bedrooms And 1 Bath And Sits On 5.05 Acres; Two Front Porches; Large Rear Porch; A Separate Room Downstairs That Would Make A Great Master Bedroom/Suite Potentially; Huge Mudroom/Flex Space! Possibilities Are Endless With This Property. This Home Has Replacement Vinyl Clad Windows, Roof And HVAC All Replaced In Last 10

    Patrick Arvin Keller Williams Commonwealth

    205 Providence Ln, Winchester, KY 40391
  • /5

    $575,000

    • Land
    • 1.71 Acres
    • $336,257 per Acre

    1025 Colby Rd, Winchester, KY 40391

    This 1.7+/- acre parcel represents an excellent opportunity for almost any commercial application. The property has 397 feet of frontage along busy Colby Road (9,170 AADT, 2015) near its intersection with the Winchester Bypass (23,200 AADT, 2011). Located in the main shopping corridor of Clark County, this property receives tons of exposure and traffic from the adjacent Walmart Super-center,

    Jo Gawthrop Keller Williams Bluegrass Realty

    1025 Colby Rd, Winchester, KY 40391
  • /55

    $350,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,835 Sq Ft

    27 Hampton Ave, Winchester, KY 40391

    Located on desirable Hampton Avenue, this all-brick ranch is full of timeless character and thoughtful updates. Beautiful original hardwood floors run throughout the main level, highlighted by detailed craftsmanship and charm you don't find every day. The spacious living room features built-ins, a fireplace, and flows into the dining area, creating a warm and inviting space for everyday living or

    Terra Long Keller Williams Commonwealth

    27 Hampton Ave, 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
  • /2

    $110,000

    • Land
    • 11,761 Sq Ft
    • $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
  • /8

    $175,000

    $20K PRICE DROP
    • Land
    • 6.59 Acres
    • $26,555 per Acre

    990 Craig Crossing Rd, Winchester, KY 40391

    Lot # 13 contains 6.588 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
  • /22

    $139,900

    • 2 Beds
    • 1 Bath
    • 986 Sq Ft

    174 Cook Ave, Winchester, KY 40391

    Charming Fixer-Upper with Endless Potential - Priced to Sell!! This older gem is full of character and opportunity! Featuring solid bones and classic charm, this property is perfect for buyers with a vision who are not afraid to add a little TLC! Whether you're an investor, DIY entusiast, or someone dreaming of restoring a home to its former glory, this is your chance to build equity and create

    A. Rebecca Woods Woods Realty Group

    174 Cook Ave, Winchester, KY 40391
  • /4

    $169,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,472 Sq Ft

    13 Maryland Ave, Winchester, KY 40391

    Welcome Home! Located across the street from a park with walking trails and 2 dog runs, this home is ready for a new owner. Featuring 2 bedrooms on the first floor and an optional 3rd bedroom or bonus room in the partially finished attic space. The original hardwood floors are located throughout the home. VA assumable loan with a 2.99% interest rate - you can't beat that in today's market! Home

    Clay David Sutherland ERA Select Real Estate

    13 Maryland Ave, Winchester, KY 40391
  • /26

    $390,000

    Open Sun 2PM - 4PM
    • 3 Beds
    • 2.5 Baths
    • 2,156 Sq Ft

    178 Hawthorne Dr, Winchester, KY 40391

    Welcome to your Kentucky haven. This charming 3 bedroom, 2.5 bath home has a covered front porch and a partially covered back deck that's perfect for enjoying the Summer outdoors. It's located in a well established neighborhood while only being 8 years old. As you step inside you will love the beautiful hardwood and tile flooring that run throughout the house. A separate mudroom is complete with

    Tiffani Casey Waizenhofer Real Estate

    178 Hawthorne Dr, Winchester, KY 40391
  • /31

    $479,000

    $26K PRICE DROP
    • 8 Beds
    • 4 Baths
    • 5,058 Sq Ft

    265 S Highland St, Winchester, KY 40391

    Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8

    J Corey Griffo RE/MAX Elite Lexington

    265 S Highland St, Winchester, KY 40391
  • /2

    $14,100,000

    • Land
    • 274.52 Acres
    • $51,362 per Acre

    2395 Paris Rd, Winchester, KY 40391

    NOW PRE-SELLING: Deerlawn Development is Winchester, Ky's most anticipated residential development--an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods. Located at 2395 Paris Road, and positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 single-family homes, and

    Melia Hord MELIA Realty LLC

    2395 Paris Rd, Winchester, KY 40391
  • /6

    $49,500

    • Land
    • 42,688 Sq Ft
    • $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

    $245,000

    $30K PRICE DROP
    • Land
    • 6.08 Acres
    • $40,296 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
  • /2

    $600,000

    • Land
    • 6.13 Acres
    • $97,879 per Acre

    722 Colby Rd Unit 2, Winchester, KY 40391

    Discover an exceptional opportunity for retail investment in the thriving Winchester area. Zoned B-4, this versatile property offers a wide array of possibilities for retail development, providing a strategic location for businesses seeking to establish a prominent presence. With its prime zoning and desirable position within the Winchester area, this property presents a compelling prospect for

    Cheryl Johnston CMI Properties

    722 Colby Rd Unit 2, Winchester, KY 40391
  • /21

    $104,900

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    563 Constitution Dr, Winchester, KY 40391

    Affordable housing! Check out this newly remodeled and updated home! 2 bedroom, 2 full bath! All new flooring, cabinets, vanities, and so much more! No lot rent here! You will own the lot as well, making this a great option for starter, downsizing, investment property (previously rented for $925), or just an affordable home. Nice covered porch, 2 storage sheds, brand new metal roof! $150 per

    Jason Townsend Kentucky Residential Real Estate, LLC

    563 Constitution Dr, Winchester, KY 40391
  • /9

    $1,350,000

    $350K PRICE INCREASE
    • 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, and

    Greg Leveridge Block + Lot Homes

    155 April Way, Winchester, KY 40391
  • /38

    $294,900

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,128 Sq Ft

    147 Sunset Heights, Winchester, KY 40391

    This charming 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and potential! On a large corner lot in a cute, established neighborhood, this property features a spacious detached garage ideal for storage, hobbies, or workshop space. Inside, you'll find a functional layout with plenty of natural light and room to make it your own. The large partially unfinished basement provides

    Lyndsey Martin Kentucky Land and Home

    147 Sunset Heights, Winchester, KY 40391
  • /2

    $100,000

    $10K PRICE DROP
    • Land
    • 13,503 Sq Ft
    • $322,581 per Acre

    215 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

    215 Duclair Dr, Winchester, KY 40391
  • /21

    $249,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,064 Sq Ft

    12 Pocahontas Trail, Winchester, KY 40391

    Here is your opportunity to purchase a new construction home built in an established neighborhood. Approaching the home you notice the large covered front porch with plenty of room for seating. When you walk in the home, you have white oak LVP flooring running throughout the living room, kitchen and dining area that are all open to one another. The kitchen has white Shaker style cabinets, granite

    Brian England Keller Williams Bluegrass Realty

    12 Pocahontas Trail, Winchester, KY 40391
  • /2

    $100,000

    $10K PRICE DROP
    • Land
    • 13,939 Sq Ft
    • $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
  • /38

    $289,900

    $7K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,116 Sq Ft

    618 Westmeade Dr, Winchester, KY 40391

    PRICE IMPROVEMENT + $3,000 BUYER CREDIT! Motivated seller has adjusted the price to $289,900 and are offering a $3,000 credit at closing to use toward your personal updates, closing costs, or an interest rate buy-down! Conveniently located, this charming well kept home features a functional floorplan offering space that can be tailored for those who love to entertain or the growing family. On the

    Kristi Donaldson United Real Estate Bluegrass

    618 Westmeade Dr, 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
  • /40

    $289,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,692 Sq Ft

    54 Locust Dr, Winchester, KY 40391

    Opportunity awaits at 54 Locust Drive in Wesleyan Park subdivision. This all-brick ranch on a full unfinished basement offers 3 bedrooms, 2 baths, and 1,692 square feet of finished living space, along with an equally spacious basement ready for storage, hobbies, or future possibilities. Built in 1960, this home features hardwood flooring, a 2-car attached garage, and a fenced backyard with a

    Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

    54 Locust Dr, Winchester, KY 40391
  • /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
  • /2

    $882,000

    • Land
    • 3.93 Acres
    • $224,427 per Acre

    Lot 1 - 7 Plantations Dr, Winchester, KY 40391

    NOW SELLING PHASE ONE: 7 of the 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 you to build

    Melia Hord MELIA Realty LLC

    Lot 1 - 7 Plantations Dr, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 13,939 Sq Ft
    • $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

    $10K PRICE DROP
    • 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
  • /2

    $110,000

    • Land
    • 13,939 Sq Ft
    • $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
  • /36

    $290,000

    Open Sun 2PM - 4PM
    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft

    20 Jackson St, Winchester, KY 40391

    Beautifully updated and move-in ready, this 3-bedroom, 2-bath home offers comfort, style, and versatility throughout. Inside, you'll find a spacious living room, an updated kitchen with ample cabinetry, tile showers, original hardwood, modern LVP, and thoughtful finishes throughout. A large utility room offers flexible space for a home office, playroom, or extra storage. The unfinished basement,

    Zova Rothchild Keller Williams Legacy Group

    20 Jackson St, Winchester, KY 40391
  • /52

    $785,000

    • 4 Beds
    • 3 Baths
    • 3,311 Sq Ft

    7300 Old Boonesboro Rd, Winchester, KY 40391

    This beautiful home sits on over 7 acres of peaceful countryside. Bring your horse! The back portion of the land is completely fenced. The private outdoor space includes a huge deck with a lovely view and an inviting covered front porch. The backyard would make the perfect space for your own dream swimming pool. Since the property has a 3-car detached garage; a 2-car attached garage plus a 1275

    Vickie Skeens RE/MAX Elite Lexington

    7300 Old Boonesboro Rd, 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
  • /2

    $78,500

    • Land
    • 9,600 Sq Ft
    • $356,171 per Acre

    Lot 4 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 MELIA Realty LLC

    Lot 4 Plantations Dr, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 21,780 Sq Ft
    • $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
  • /12

    $279,000

    $26K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,214 Sq Ft

    55 Hillcrest Dr, Winchester, KY 40391

    Open house 05/10 2-*4 pm **Don't miss this exciting opportunity to pick out the new flooring for the basement and kitchen with a full price offer.****New roof (6 months old), one year old AC and heating unit, new large storage shed, and one year old wooden fence All of the expensive upgrades have been done. Come make this home your own. All-brick ranch with a full walk-out basement! This charming

    Nina Vanetten RE/MAX Elite Lexington

    55 Hillcrest Dr, Winchester, KY 40391
  • /14

    $189,999

    • 3 Beds
    • 1 Bath
    • 950 Sq Ft

    41 Hiawatha Trail, Winchester, KY 40391

    Investor Special with Charm & Potential! Don't miss this opportunity to bring new life to this adorable brick home full of character and promise! Featuring beautiful hardwood floors, timeless curb appeal, and a layout ready to shine again, this property is the perfect canvas for your next project. Whether you're an investor, flipper, or buyer looking to build equity, this home offers classic

    Hannah Toole Coldwell Banker McMahan

    41 Hiawatha Trail, Winchester, KY 40391

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