Winchester, KY Homes for Sale

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  /84

  $649,000

  $150K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 4,928 Sq Ft

  186 Chardonnay Ct, Winchester, KY 40391

  Fontaine Estates, a great place to call home. This spacious 4 bedroom 3 bath property offers an abundance of storage,, including charming window seats. Enjoy the convenience of an oversized driveway and garage, along with a beautifully designed outdoor setting, feauring a fire pit and a dedicated entertainment space. The thoughtfully planned, custom designed landscaping enhances the home's curb

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  186 Chardonnay Ct, Winchester, KY 40391
• Explore Winchester

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  /45

  $855,000

  Open Sun 2PM - 4PM

  • 3 Beds
  • 3 Baths
  • 2,872 Sq Ft

  5960 Van Meter Rd, Winchester, KY 40391

  Discover the charm of country living on nearly 15 acres of beautiful, mostly flat to gently rolling farmland, offering picturesque views and plenty of space to enjoy the outdoors. This well-maintained property features a barn, equipment shed, workshop, and an attached three-bay garage, providing exceptional storage and workspace for equipment, hobbies, or farm use. Inside the home, you'll find

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  5960 Van Meter Rd, Winchester, KY 40391
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  /31

  $275,000

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  4305 Old Boonesboro Rd, Winchester, KY 40391

  Enjoy peaceful country living on this beautiful 2+ acre property featuring a nearly new manufactured home and a spacious barn. Surrounded by scenic countryside views, this property offers plenty of privacy, comfort, and room to enjoy the outdoors. The well-kept home provides a cozy place to relax, while the large barn and open space give you plenty of options for storage, hobbies, gardening,

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  4305 Old Boonesboro Rd, Winchester, KY 40391
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  /26

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  317 Vanover Way, Winchester, KY 40391

  Welcome to 317 Vanover Way! This beautiful, well-maintained 3-bedroom, 2-bath home is move-in ready and waiting for its next owner. Step inside to a spacious living room with the bedrooms conveniently located just off the main living area. Coming in from the garage, you'll find a functional mudroom and laundry area that leads directly into the kitchen. Outside, enjoy a nice-sized fenced backyard

  

  Austina Bruton

  Rector Hayden Realtors

  317 Vanover Way, Winchester, KY 40391
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  /50

  $239,900

  $15K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,533 Sq Ft

  377 Crescent Ave, Winchester, KY 40391

  "Motivated sellers—bring your offers!" Step into this charming 3-bedroom, 2-bath home that's full of character and timeless appeal. From the beautiful hardwood floors to the inviting living spaces, this older home offers warmth and personality you simply don't find in newer construction. The spacious living room provides plenty of room to relax or entertain, while the separate dining room is

  

  Bill VanWinkle

  Joyce Marcum Realty

  377 Crescent Ave, Winchester, KY 40391
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  /64

  $420,000

  • 3 Beds
  • 2 Baths
  • 2,027 Sq Ft

  187 Hawthorne Dr, Winchester, KY 40391

  Welcome to 187 Hawthorne Drive, a beautifully maintained brick home in one of Winchester's most sought-after neighborhoods. Offering convenient one-level living, this 3-bedroom, 2-bath home features an inviting open floor plan that's perfect for everyday living and entertaining. The spacious living room is anchored by a cozy natural gas fireplace with gas logs, creating a warm and welcoming

  

  Christa Joynt

  Keller Williams Commonwealth

  187 Hawthorne Dr, Winchester, KY 40391
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  /74

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  2725 Goshen Rd, Winchester, KY 40391

  Welcome to this one-owner home offering the perfect combination of space, thoughtful updates, and country living! Built in 1996 and situated on 1.67 beautiful acres, this well-maintained 3-bedroom, 2-bath home features 1,344 square feet of comfortable living space with numerous improvements already completed for its next owner. Inside, you'll find updated interior paint, durable LifeProof

  

  Christa Joynt

  Keller Williams Commonwealth

  2725 Goshen Rd, Winchester, KY 40391
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  /18

  $490,000

  $66K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,102 Sq Ft

  110 White Conkwright Rd, Winchester, KY 40391

  Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

  

  Philip 'PJ' Elder

  Omega Real Estate Brokerage LLC

  110 White Conkwright Rd, Winchester, KY 40391
• 

  

  /64

  $379,000

  $41K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,978 Sq Ft

  107 Hibiscus Ln, Winchester, KY 40391

  Welcome to 107 Hibiscus, where thoughtful updates, quality craftsmanship, and exceptional maintenance come together in this spacious 4-bedroom, 2.5-bath home. Offering a versatile floor plan with generous living spaces, this move-in-ready property has benefited from approximately nearly $70,000 in improvements over the past several years, providing peace of mind and modern finishes throughout.

  

  Christa Joynt

  Keller Williams Commonwealth

  107 Hibiscus Ln, Winchester, KY 40391
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  /2

  $78,500

  • Land
  • 16,552 Sq Ft
  • $206,579 per Acre

  2395 Paris Rd Unit Lot 1, Winchester, KY 40391

  Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family

  

  Melia Hord

  MELIA Realty LLC

  2395 Paris Rd Unit Lot 1, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 21,780 Sq Ft
  • $157,000 per Acre

  2395 Paris Rd Unit Lot 5, Winchester, KY 40391

  Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family

  

  Melia Hord

  MELIA Realty LLC

  2395 Paris Rd Unit Lot 5, Winchester, KY 40391
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  /2

  $78,500

  • Land
  • 19,166 Sq Ft
  • $178,409 per Acre

  2395 Paris Rd Unit Lot 3, Winchester, KY 40391

  Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family

  

  Melia Hord

  MELIA Realty LLC

  2395 Paris Rd Unit Lot 3, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 15,158 Sq Ft
  • $225,575 per Acre

  2395 Paris Rd Unit Lot 6, Winchester, KY 40391

  Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family

  

  Melia Hord

  MELIA Realty LLC

  2395 Paris Rd Unit Lot 6, Winchester, KY 40391
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  /29

  $150,000

  • 3 Beds
  • 1 Bath
  • 1,842 Sq Ft

  5 S Burns Ave, Winchester, KY 40391

  Welcome home to this charming 3-bedroom, 1-bathroom property featuring a comfortable living room, dedicated dining room, and a functional layout with plenty of potential. Outside, you'll find a detached 1-car garage and a long driveway. Whether you're looking for your first home or your next investment opportunity, this property offers a great combination of space, functionality, and potential.

  

  Tirza Howard

  The Howard Realty Co

  5 S Burns Ave, Winchester, KY 40391
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  /35

  $299,900

  $20K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,082 Sq Ft

  128 Cherokee Dr, Winchester, KY 40391

  Welcome to 128 Cherokee Drive, where space, versatility, and convenience come together! This all-brick split-foyer home offers 5 bedrooms, 2 full bathrooms, and over 2,000 square feet of comfortable living space, making it ideal for growing families, multi-generational living, or anyone needing extra room. The main level features a bright and inviting living room, while the finished lower level

  

  Tyler Hurst

  Oak & Acre

  128 Cherokee Dr, Winchester, KY 40391
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  /2

  $78,500

  • Land
  • 22,651 Sq Ft
  • $150,962 per Acre

  2395 Paris Rd Unit Lot 4, Winchester, KY 40391

  Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family

  

  Melia Hord

  MELIA Realty LLC

  2395 Paris Rd Unit Lot 4, Winchester, KY 40391
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  /46

  $749,900

  • 3 Beds
  • 2.5 Baths
  • 2,735 Sq Ft

  2180 Big Stoner Rd, Winchester, KY 40391

  Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides

  

  Ashley Barreto

  Indigo & Co

  2180 Big Stoner Rd, Winchester, KY 40391
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  /4

  $64,900

  • Land
  • 27,878 Sq Ft
  • $101,406 per Acre

  102 Royal Oak Dr, Winchester, KY 40391

  One of the Few Remaining Estate Homesites in Royal Oaks Estates! An exceptional opportunity awaits to build your custom dream home in the Estate Section of Royal Oaks, one of Clark County's most established and desirable communities. Situated on 0.64 acres, 102 Royal Oak Drive offers the space, setting, and flexibility to create a home tailored to your lifestyle while enjoying the beauty and

  

  Melia Hord

  MELIA Realty LLC

  102 Royal Oak Dr, Winchester, KY 40391
• 

  /2

  $14,100,000

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

  2395 Paris Rd, Winchester, KY 40391

  Welcome to Deerlawn, Winchester's newest approved residential development and a major new-construction opportunity in Clark County. Located at 2395 Paris Road, Deerlawn is a 274-acre master-planned community designed to deliver 438 single-family homes, along with additional duplex and townhome opportunities, creating long-term scale for builders and more choices for buyers looking to build in

  

  Melia Hord

  MELIA Realty LLC

  2395 Paris Rd, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 15,246 Sq Ft
  • $224,286 per Acre

  2395 Paris Rd Unit Lot 2, Winchester, KY 40391

  Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family

  

  Melia Hord

  MELIA Realty LLC

  2395 Paris Rd Unit Lot 2, Winchester, KY 40391
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  /23

  $249,500

  • Land
  • 14.51 Acres
  • $17,194 per Acre

  3056 Irvine Rd, Winchester, KY 40391

  Discover the perfect blend of beauty, privacy, and opportunity with this stunning 14.511-acre tract on Irvine Road. Featuring gently rolling hills, this property offers multiple ideal building sites to bring your dream home to life, whether you're envisioning a modern farmhouse, barndominium, or private country retreat. A barn is already in place, adding immediate functionality for storage,

  

  Christa Joynt

  Keller Williams Commonwealth

  3056 Irvine Rd, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 13,982 Sq Ft
  • $244,548 per Acre

  2395 Paris Rd Unit LOT 7, Winchester, KY 40391

  Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family

  

  Melia Hord

  MELIA Realty LLC

  2395 Paris Rd Unit LOT 7, Winchester, KY 40391
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  /41

  $343,900

  New Construction

  • 3 - 5 Beds
  • 2 - 4 Baths
  • 1,424 Sq Ft

  Lucy Plan at Boone's Crossing, Winchester, KY 40391

  Experience the Lucy floor plan, a versatile and thoughtfully designed new construction home that gives every member of the family the space they need to live, work, and thrive. Built by one of the most trusted home builders in Central Kentucky, the Lucy is a top choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want flexibility, comfort, and

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824256, Winchester, KY 40391
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  /37

  $378,900

  New Construction

  • 3 - 5 Beds
  • 2.5 - 3.5 Baths
  • 2,098 Sq Ft

  Nancy Plan at Boone's Crossing, Winchester, KY 40391

  Experience the Nancy floor plan, a masterfully designed two-story new construction home that blends smart functionality with open-concept living. Built by one of the most trusted home builders in Central Kentucky, the Nancy is an ideal choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want style, flexibility, and efficient use of space.From the

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824252, Winchester, KY 40391
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  /45

  $429,900

  New Construction

  • 3 - 5 Beds
  • 2.5 - 4.5 Baths
  • 2,722 Sq Ft

  Eleanor Plan at Boone's Crossing, Winchester, KY 40391

  Experience elevated living with the Eleanor floor plan, a thoughtfully designed new construction home available through one of the most trusted home builders in Central Kentucky. Created for today’s buyers seeking flexibility, luxury, and energy efficiency, the Eleanor blends timeless design with modern functionality for families looking for new construction homes in Lexington KY and surrounding

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824255, Winchester, KY 40391
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  /35

  $360,900

  New Construction

  • 3 - 4 Beds
  • 2.5 - 3.5 Baths
  • 1,828 Sq Ft

  Grace Plan at Boone's Crossing, Winchester, KY 40391

  Discover the Grace floor plan, a thoughtfully designed new construction home that blends open-concept living with private, comfortable bedroom spaces. Built by one of the leading home builders in Central Kentucky, the Grace is a perfect fit for buyers searching for new construction homes in Lexington KY and nearby communities who want flexibility, style, and energy efficiency.From the moment you

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824257, Winchester, KY 40391
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  /46

  $347,900

  New Construction

  • 3 - 6 Beds
  • 2 - 4 Baths
  • 1,580 Sq Ft

  Martha Plan at Boone's Crossing, Winchester, KY 40391

  The Martha floor plan is your canvas for creating a home that perfectly fits your lifestyle, offering unmatched flexibility, thoughtful design, and timeless appeal. Built by one of the leading home builders in Central Kentucky, the Martha is an excellent choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space that adapts to how they

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824258, Winchester, KY 40391
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  /28

  $363,900

  New Construction

  • 4 - 5 Beds
  • 2.5 - 3.5 Baths
  • 2,100 Sq Ft

  Elizabeth Plan at Boone's Crossing, Winchester, KY 40391

  Experience the Elizabeth floor plan, a beautifully crafted new construction home designed for families who value open-concept living, thoughtful organization, and flexible bedroom space. Offered by one of the most trusted home builders in Central Kentucky, the Elizabeth is a standout option for buyers searching for new construction homes in Lexington KY and surrounding communities.From the moment

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824250, Winchester, KY 40391
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  /85

  $397,900

  New Construction

  • 3 - 5 Beds
  • 2.5 - 4.5 Baths
  • 2,263 Sq Ft

  Abigail Plan at Boone's Crossing, Winchester, KY 40391

  Step into the award-winning Abigail floor plan, a standout choice for buyers searching for new construction homes in Lexington, KY and Central Kentucky. Designed with today’s lifestyle in mind, this home offers the perfect blend of flexible floor plans, energy efficiency, and modern comfort—everything you expect from a trusted home builder in Lexington, KY.From the moment you arrive, the Abigail

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824251, Winchester, KY 40391
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  /52

  $369,900

  New Construction

  • 3 - 6 Beds
  • 2 Baths
  • 1,770 Sq Ft

  Barbara Plan at Boone's Crossing, Winchester, KY 40391

  Experience the true essence of homecoming with the Barbara floor plan, a beautifully designed new construction home available through one of the most trusted home builders in Central Kentucky. Thoughtfully crafted for modern living, this plan blends timeless exterior charm with a warm, open interior designed for comfort, flexibility, and everyday functionality.Step onto the inviting covered front

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824253, Winchester, KY 40391
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  /127

  $3,450,000

  • 2 Beds
  • 2.5 Baths
  • 2,725 Sq Ft

  510 - 612 Quisenberry Ln, Winchester, KY 40391

  Adjoining the banks of the Lower Howard's Creek in Clark County lies a very special 145.6± acre farm. With some of the oldest settlements in the county, this region near the Old Stone Church (or Old Providence Church) is immensely historic. Daniel Boone's first eleven surveys in Kentucky were conducted for the Bush family, early inhabitants of the area and farm. With gated stone entrances and

  Zach Davis Kirkpatrick & Company

  510 - 612 Quisenberry Ln, Winchester, KY 40391
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  /51

  $399,900

  $27K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,289 Sq Ft

  20 Edgewood Dr, Winchester, KY 40391

  Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a

  Libby VanMeter Marshall Lane Real Estate - Lexington

  20 Edgewood Dr, Winchester, KY 40391
• 

  

  /19

  $189,000

  $20K PRICE DROP

  • Land
  • 41.69 Acres
  • $4,534 per Acre

  2697 Pine Ridge Rd, Winchester, KY 40391

  Escape to your own private retreat with this stunning 41.6± acre wooded tract nestled in the scenic countryside of Winchester, Kentucky. This expansive property offers a rare opportunity to own a secluded slice of nature, perfect for a private estate, recreational getaway, or hunting retreat. With rich with mature timber, this land presents a lot of natural beauty. A network of cleared trails and

  Derek Blankenship Keller Williams Commonwealth

  2697 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /17

  $260,000

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  280 Pine Ridge Rd, Winchester, KY 40391

  This listing includes 3 lots in total, 251, 270 and 280 Pine Ridge Rd. All total 12.04 Acres per the PVA. The home is being sold as is.Public Remarks: Bring your vision to life on 12+ beautiful acres in Winchester! This 3-bedroom, 1-bath home offers the charm of a 1964 build and the opportunity to create your own private retreat. With plenty of room for gardens, animals, workshops, or

  Derek Blankenship Overland Properties Group @ KW Commonwealth

  280 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /19

  $460,000

  $39K PRICE DROP

  • Land
  • 36.94 Acres
  • $12,453 per Acre

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391

  Don't miss this rare chance to own 36.45 premium acres on the outskirts of Winchesteran unbeatable blend of open farmland, development potential, and a truly top-tier location. Just minutes from I-64 and a quick drive to Lexington, this tract offers the convenience buyers want with the space and freedom they rarely find. The gorgeous rolling fields make this property ideal for farming, hay

  Greg Meade Whitetail Properties Real Estate

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391
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  /48

  $304,900

  • 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
• 

  /2

  $1,200,000

  $596K PRICE INCREASE

  • Land
  • 24.15 Acres
  • $49,689 per Acre

  1395 Two Mile Rd, Winchester, KY 40391

  PLANNED DEVELOPMENT INVESTMENT INVESTMENT OPPORTUNITY! Already zoned Planned Development! There is an approximately 24 acre tract zoned for all forms of Residential use. (In addition there is an approximately 21 acre Residential tract that adjoins the Winchester Country Club. The two Residential tracts have access to gravity flow sewer. Sewer maps available. The remaining

  Garnett Davis Tom Goebel & Company

  1395 Two Mile Rd, Winchester, KY 40391
• 

  /2

  $110,000

  • Land
  • 16,552 Sq Ft
  • $289,474 per Acre

  200 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

  200 Duclair Dr, Winchester, KY 40391
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  /27

  $265,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  15 Kittison Dr, Winchester, KY 40391

  Welcome home to 15 Kittison Drive! Perfectly blending classic 1960s character with modern convenience, this Winchester residence offers comfort, space, and an unbeatable location just one mile from I-64. Inside, you'll find three spacious bedrooms and two full bathrooms designed for effortless daily living. The versatile, light-filled layout includes a large living room, a functional kitchen, and

  Cheri Shaffer Lifstyl Real Estate

  15 Kittison Dr, Winchester, KY 40391
• 

  

  /3

  $399,000

  • Land
  • 11.3 Acres
  • $35,310 per Acre

  0 Fairholme Way, Winchester, KY 40391

  11 acres of golf course adjacent land with development plan. Owner/Broker. Road and utility estimates available upon request. A list of individuals interested in lots available upon contract.

  Steve Adams Steven D Adams Real Estate Services, LLC

  0 Fairholme Way, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 6

Why Live in Winchester

Winchester, KY, the largest city in Clark County, is known for its vibrant community and unique local flavors, including the birthplace of beer cheese and Ale-8-One soda. Main Street is the hub for dining, featuring popular spots like La Trattoria and Loma’s, and the Beer Cheese Trail, which includes around 15 restaurants with signature beer cheese recipes. The city offers practical amenities with nearby grocery stores like Kroger and Walmart Supercenter, and retail options such as TJ Maxx and Lowe’s. Housing in Winchester includes Victorian-era inspired homes and newer subdivisions, with properties often featuring gravel driveways and spacious lawns suitable for gardens. Clark County Public Schools provide strong academic programs, including AP and dual enrollment courses at George Rogers Clark High School. For outdoor activities, residents enjoy Legacy Grove Park, College Park, and Lykins Park, which offer facilities for basketball, tennis, hiking, and disc golf. Winchester hosts annual events like the Beer Cheese Festival and the Daniel Boone Pioneer Festival, attracting visitors with arts, crafts, and food. The Bluegrass Heritage Museum showcases the history of Central Kentucky. Commuting is convenient with Winchester located 16 miles from Lexington and 20 miles from Richmond. The city has a cooperative community spirit, bolstered by investments from younger residents and a thriving local economy.

Learn more about living in Winchester

Winchester, KY Home Prices vs. Nearby Neighborhoods

	Winchester, KY	Becknerville
Median Home Price	$270,000	$382,500
Median Sale Price	$264,000 +10% YoY	$345,000 +15% YoY
Avg. Price per Square Foot	$160	$186
Median Single Family Price	$267,000	$392,000
Median Townhouse Price	$195,000	$207,500
Total Active Listings	207 listings	33 listings
Market Conditions	3 Months of Supply Seller's Market	5 Months of Supply Balanced Market

Frequently Asked Questions

What is the average home price in Winchester, KY?

Homes for sale in Winchester, KY have an average home price of $333,353.

How many homes have sold over the last 12 months in Winchester, KY?

285 homes have sold in Winchester, KY over the last 12 months.

What is the average household income in Winchester, KY?

The average household income in Winchester, KY is $68K.

What are the most popular zip codes in Winchester, KY?

The most popular zip codes in Winchester, KY include 40391, 40516, 40509, 40361 and 40353.

What are the most popular neighborhoods in Winchester, KY?

The most popular neighborhoods in Winchester, KY with the most homes for sale are Old Pine Grove, Becknerville and Wyandotte.

How much do you need to make to afford a house in Winchester?

The median home price in Winchester is $270,000. If you put a 20% down payment of $54,000 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $1,430 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $61K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winchester is $68K.

How are the schools in Winchester, KY?

Winchester, KY has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are Baker Intermediate School, Strode Station Elementary School and George Rogers Clark High School. The neighborhoods in Winchester with the highest rated schools are Old Pine Grove, Becknerville and Wyandotte. Browse all the schools in Winchester, KY to learn more.