Winchester, KY Homes for Sale

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  /64

  $419,500

  • 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
• Explore Winchester

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  /84

  $675,000

  $124K 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
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  /55

  $249,900

  • 3 Beds
  • 1 Bath
  • 1,204 Sq Ft

  10 Chickadee Ln, Winchester, KY 40391

  Welcome to 10 Chickadee Lane, Winchester, KY—a beautifully updated 3-bedroom, 1-bath ranch offering the perfect combination of modern upgrades, timeless character, and an unbeatable location. If you're searching for a move-in ready home in Winchester, Kentucky, this one deserves a spot at the top of your list. Extensively renovated in 2020, this home provides peace of mind with major improvements

  

  Christa Joynt

  Keller Williams Commonwealth

  10 Chickadee Ln, Winchester, KY 40391
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  /24

  $280,000

  • 4 Beds
  • 3.5 Baths
  • 3,276 Sq Ft

  133 Bay Hill Dr, Winchester, KY 40391

  Welcome to 133 Bay Hill Drive in Winchester, Kentucky — a spacious and beautifully maintained home offering over 3,200 square feet of living space in one of the area's desirable subdivisions. Conveniently located just minutes from town and close to local factories and major employers, this property offers the perfect blend of comfort, convenience, and neighborhood living. Inside, you'll find

  

  Dustin Pennington

  Keller Williams Legacy Group

  133 Bay Hill Dr, Winchester, KY 40391
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  /31

  $315,000

  • 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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  /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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  /18

  $515,000

  Open Sun 1PM - 3PM $41K 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
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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
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  /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
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  /2

  $78,500

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

  231 Plantations Dr Unit LOT 2, Winchester, KY 40391

  Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #2 is now available and ready for you to bring your own builder and create the home you've

  

  Melia Hord

  MELIA Realty LLC

  231 Plantations Dr Unit LOT 2, Winchester, KY 40391
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  /72

  $775,000

  • 5 Beds
  • 3 Baths
  • 4,437 Sq Ft

  465 Morris Rd, Winchester, KY 40391

  Dreaming of wide-open spaces and country charm? This beautiful 16-acre property in Clark County offers the perfect blend of comfort and functionality. The stately brick home provides generous living space with classic appeal, offering endless potential. With five bedrooms and three full baths, the home accommodates a variety of living arrangements, whether you need space for guests, a home

  

  Brenda Leigh Walters

  United Real Estate Bluegrass

  465 Morris Rd, Winchester, KY 40391
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  /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
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  /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
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  /23

  $250,000

  • Land
  • 14.51 Acres
  • $17,228 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
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  /2

  $78,500

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

  241 Plantations Dr Unit LOT 7, Winchester, KY 40391

  Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #7 is now available and ready for you to bring your own builder and create the home you've

  

  Melia Hord

  MELIA Realty LLC

  241 Plantations Dr Unit LOT 7, Winchester, KY 40391
• 

  /2

  $78,500

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

  229 Plantations Dr Unit LOT 1, Winchester, KY 40391

  **Welcome to DEERLAWN at Royal Oaks—Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #1** is now available and ready for you to bring your own builder and create

  

  Melia Hord

  MELIA Realty LLC

  229 Plantations Dr Unit LOT 1, Winchester, KY 40391
• 

  /2

  $78,500

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

  237 Plantations Dr Unit LOT 5, Winchester, KY 40391

  **Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #5** is now available and ready for you to bring your own builder and create

  

  Melia Hord

  MELIA Realty LLC

  237 Plantations Dr Unit LOT 5, Winchester, KY 40391
• 

  /2

  $78,500

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

  233 Plantations Dr Unit LOT 3, Winchester, KY 40391

  Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #3 is now available and ready for you to bring your own builder and create the home you've

  

  Melia Hord

  MELIA Realty LLC

  233 Plantations Dr Unit LOT 3, Winchester, KY 40391
• 

  /2

  $78,500

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

  239 Plantations Dr Unit LOT 6, Winchester, KY 40391

  **Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #6** is now available and ready for you to bring your own builder and create

  

  Melia Hord

  MELIA Realty LLC

  239 Plantations Dr Unit LOT 6, Winchester, KY 40391
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  /46

  $239,000

  $8K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  30 Virginia Ave, Winchester, KY 40391

  Welcome to a well maintained 3 bedroom 1 full bath home that has been lovingly cared for by only two owners since 1962. Recent updates include new flooring and completed repairs, makiing this property ready for a new owner, while preserving its timeless character. Beautiful hardwood floors add warmth and charm throughout the home. Enjoy relaxing or entertaining on the comfortable spacious patio

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  30 Virginia Ave, Winchester, KY 40391
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  /35

  $319,900

  • 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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  /21

  $175,000

  • Land
  • 11.36 Acres
  • $15,402 per Acre

  2996 Irvine Rd, Winchester, KY 40391

  Discover the perfect blend of convenience and countryside charm with this beautiful 11+ acre tract located just outside of Winchester in Clark County. Offering gently rolling terrain and multiple potential building sites, this property provides an ideal setting for your dream home, mini-farm, or private retreat.Enjoy the peace and privacy of rural living without sacrificing accessibility and just

  

  Christa Joynt

  Keller Williams Commonwealth

  2996 Irvine Rd, Winchester, KY 40391
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  /74

  $329,000

  $10K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,068 Sq Ft

  13 Bel Air Dr, Winchester, KY 40391

  Don't let this charming brick ranch fool you—it's what's waiting out back that will absolutely steal the show! Nestled in the heart of Winchester, this 3BR/3BA home offers an incredible backyard oasis that's perfect for entertaining, relaxing, and making memories all summer long. The sparkling in-ground pool is the centerpiece of this private retreat, surrounded by expansive concrete decking and

  

  Robin Jones

  Keller Williams Legacy Group

  13 Bel Air Dr, Winchester, KY 40391
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  /25

  $425,000

  • Land
  • 25.87 Acres
  • $16,426 per Acre

  2996/3056 Irvine Rd, Winchester, KY 40391

  Rare opportunity to own over 25 acres of beautiful Kentucky countryside on Irvine Road, combining two adjoining tracts into one exceptional offering. With gently rolling hills and multiple ideal building sites, this property provides the perfect setting to create your dream home, private estate, or mini-farm. The land offers a wonderful balance of usability and natural beauty, featuring a scenic

  

  Christa Joynt

  Keller Williams Commonwealth

  2996/3056 Irvine Rd, Winchester, KY 40391
• 

  /2

  $78,500

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

  MELIA Realty LLC

  Lot 3 Plantations Dr, Winchester, KY 40391
• 

  /2

  $78,500

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

  235 Plantations Dr Unit LOT 4, Winchester, KY 40391

  Welcome to DEERLAWN at Royal Oaks—Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #4 is now available and ready for you to bring your own builder and create the home you've

  

  Melia Hord

  MELIA Realty LLC

  235 Plantations Dr Unit LOT 4, 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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  /55

  $270,000

  • 6 Beds
  • 4 Baths
  • 3,090 Sq Ft

  21 Beckner St, Winchester, KY 40391

  Outstanding opportunity for investors or owner-occupants! This beautifully updated duplex is located in Winchester's desirable Stuarts Addition and offers two spacious units, each featuring approximately 1,545 square feet with 3 bedrooms and 2 full bathrooms. Both units have been thoughtfully renovated and feature hardwood flooring throughout the main living areas with tile in the wet areas for

  Rex Hall United Real Estate Bluegrass

  21 Beckner St, 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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  /47

  $413,000

  Open Sun 2PM - 4PM $14K 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
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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
• 

  

  /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
• 

  

  /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
• 

  

  /85

  $1,349,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,350 Sq Ft

  1200 Craig Crossing, Winchester, KY 40391

  Discover elevated living on 2.5 acres! This 3,350 sqft custom masterpiece boasts 4 bedrooms, 4.5 bathrooms with an open 2,670 sqft main level. Featuring custom solid oak cabinetry not only in kitchen, but master closets, pantry and utility areas. Custom Showers and tile in each bathroom throughout the home. Gas and electric fireplaces located in great room as well as primary first floor bedroom.

  Michael Hilario The Agency

  1200 Craig Crossing, Winchester, KY 40391
• 

  

  /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
• 

  

  /19

  $209,000

  • Land
  • 41.68 Acres
  • $5,014 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 Overland Properties Group @ KW Commonwealth

  2697 Pine Ridge Rd, 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

Frequently Asked Questions

What is the average home price in Winchester, KY?

Homes for sale in Winchester, KY have an average home price of $333,470.

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

308 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.

Is Winchester, KY a safe city?

In general, the safest neighborhoods in Winchester, KY with lower crime scores are Old Pine Grove, Becknerville and Wyandotte.

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 $274,950. If you put a 20% down payment of $55,000 and had a 30-year fixed mortgage with an interest rate of 6.58%, your estimated principal and interest payment would be $1,400 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $60K 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.

Home Prices in Winchester, KY

The median home sale price in Winchester, KY is $262,750, up 9% year-over-year. Homes in Winchester sell in 32 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price $262,750	Median Single Family Sale Price $270,000
Median Townhouse Sale Price $195,000	Median 2 Bedroom Sale Price $164,500
Median 1 Bedroom Sale Price $164,900	Average Price Per Sq Ft $163
Number of Homes for Sale 90	Last 12 months Home Sales 308
Months of Supply 3.50	Median List Price $274,950
Median Change From 1st List Price 2%	Median Home Sale Price YoY Change 9%