Winchester, KY Homes for Sale

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  /32

  $375,000

  $50K PRICE DROP

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

  4305 Old Boonesboro Rd, Winchester, KY 40391

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 549-3072

  4305 Old Boonesboro Rd, Winchester, KY 40391
• Explore Winchester

• 

  

  

  /18

  $550,000

  $6K 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

  (859) 695-3879

  110 White Conkwright Rd, Winchester, KY 40391
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  /80

  $749,999

  $49K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 7,058 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

  (859) 470-2071

  186 Chardonnay Ct, Winchester, KY 40391
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  /12

  $185,900

  $4K PRICE DROP

  • 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

  (859) 695-6124

  41 7th St, Winchester, KY 40391
• 

  

  

  /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

  (859) 577-9032

  2996/3056 Irvine Rd, Winchester, KY 40391
• 

  

  /20

  $300,000

  • Land
  • 15.27 Acres
  • $19,652 per Acre

  4025 Jackson Ferry Rd, Winchester, KY 40391

  Opportunities like this are incredibly rare—15.266 combined acres backing to the Kentucky River, offering the ultimate private retreat. Located at the end of a scenic drive, these two tracts are being offered together, creating an expansive recreational property with unmatched access to the water. Ideal for camping, family getaways, or creating a multi-use outdoor haven, this land provides

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 208-1610

  4025 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /57

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,779 Sq Ft

  720 Terry Dr, Winchester, KY 40391

  Welcome home to this beautifully refreshed 3-bedroom, 2-bath property located in the heart of Winchester, KY, just minutes from the Winchester Bypass for quick and easy commuting. Priced at $275,000, this home offers exceptional value in a highly walkable and convenient neighborhood. Step inside to find a freshly painted interior that feels bright, clean, and move-in ready. The thoughtful layout

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 903-5709

  720 Terry Dr, Winchester, KY 40391
• 

  

  /22

  $180,000

  • Land
  • 10.05 Acres
  • $17,919 per Acre

  3925 Jackson Ferry Rd, Winchester, KY 40391

  This 10.045-acre tract offers the total package...scenic surroundings, river access, and improvements already in place. Situated along a quiet, picturesque drive, the property features a solid barn that has recently been painted and structurally reinforced, adding both character and functionality. With a picturesque build site available, this land is ready for your dream home, hobby farm, and

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 765-6501

  3925 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /29

  $70,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 750 Sq Ft

  113 Mimosa Dr, Winchester, KY 40391

  Discover the perfect balance between home ownership, affordability, and rural tranquility in this charming 3-bedroom two bath home. Conveniently located near shopping areas and interstates providing easy access to Lexington, Winchester and many central Kentucky cities. The interior features freshly updated flooring, offering a cohesive feel to living spaces. The true highlight of this property is

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 328-1402

  113 Mimosa Dr, Winchester, KY 40391
• 

  

  /36

  $319,900

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

  128 Cherokee Dr, Winchester, KY 40391

  Welcome to 128 Cherokee Drive, a beautifully maintained home in a quiet and desirable neighborhood. With 5 bedrooms, two full bathrooms, and a second living room on the lower floor, there is plenty of room for the entire family and friends. A spacious backyard , many appealing updates since 2022 including a brand new furnace installed in February of 2026, new insulation and baffling, and

  

  Tyler Hurst

  Oak & Acre

  (859) 927-8049

  128 Cherokee Dr, Winchester, KY 40391
• 

  

  /28

  $84,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft

  300 Aspen Ln, Winchester, KY 40391

  Welcome home to this well-maintained 3 bedroom, 2 bathroom double wide manufactured home in Treehaven, offering close to 2,000 square feet of comfortable living space...a rare find for buyers looking for room, functionality, and flexibility. Inside, you'll love the open-concept layout that connects the large living room, kitchen, and dining area, making it ideal for both everyday living and

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 903-5711

  300 Aspen Ln, Winchester, KY 40391
• 

  

  /17

  $97,500

  • Land
  • 7.99 Acres
  • $12,201 per Acre

  3991 Jackson Ferry Rd, Winchester, KY 40391

  Offering the same peaceful setting and rare river access, this tract provides a fantastic opportunity for recreational land ownership at an affordable price. Backing directly to the Kentucky River, it's an ideal spot for camping, weekend retreats, arrowhead hunting or enjoying the outdoors with kayaking, fishing, and more right at your fingertips. This property's fertile soil opens the door for

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 600-6640

  3991 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /23

  $150,000

  • Land
  • 9.39 Acres
  • $15,971 per Acre

  3821 Jackson Ferry Rd, Winchester, KY 40391

  If you've been dreaming of building a home with river access, this is it. Located along a breathtaking stretch of Jackson Ferry Road, this 9.392-acre tract offers a rare combination of a viable build site and direct access to the scenic Kentucky River. Whether it's morning coffee overlooking the countryside or afternoons spent kayaking and fishing, this property delivers a lifestyle that's hard

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 696-7578

  3821 Jackson Ferry Rd, 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

  (859) 459-0504

  465 Morris Rd, Winchester, KY 40391
• 

  

  /17

  $97,500

  • Land
  • 8.46 Acres
  • $11,522 per Acre

  3961 Jackson Ferry Rd, Winchester, KY 40391

  Escape to your own slice of Kentucky countryside with this 8.462-acre tract nestled along a scenic stretch of Jackson Ferry Road. Backing up to the Kentucky River, this property is perfect for recreational use, whether you're looking to camp, garden, or create a weekend getaway. This land provides plenty of space for campers and outdoor enjoyment throughout much of the year. The soil is rich and

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 295-6825

  3961 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /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

  (859) 534-9808

  3056 Irvine Rd, Winchester, KY 40391
• 

  

  /21

  $105,000

  • Land
  • 9.75 Acres
  • $10,767 per Acre

  3759 Jackson Ferry Rd, Winchester, KY 40391

  Tucked along a peaceful, scenic drive, this 9.752-acre tract offers a rare opportunity to own land backing directly to the beautiful Kentucky River. This parcel is the perfect recreational escape-ideal for parking a camper, weekend getaways, or creating your own private retreat. Spend your days kayaking, canoeing, fishing, or paddle boarding right from your property, then unwind surrounded by

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 217-4705

  3759 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /22

  $139,000

  $8K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 807 Sq Ft

  3208 Ford Hampton Rd, Winchester, KY 40391

  Escape to a lifestyle defined by the peace and natural beauty of this delightful two bedroom property just steps away from the majestic Kentucky River, this home isn't just a place to iive, it is a dedicated sanctuary whether you are seeking a cozy year round residence or a recreational retreat. One of the standout features is the exceptioal connection to the outdoors with generous porches on

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 765-6889

  3208 Ford Hampton Rd, Winchester, KY 40391
• 

  

  /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

  (859) 648-3896

  2996 Irvine Rd, 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

  $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
• 

  

  /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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  /47

  $427,000

  • 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
• 

  

  /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
• 

  

  /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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  /60

  $257,000

  $42K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,273 Sq Ft

  119 Tower Ln, Winchester, KY 40391

  A rare and refined retreat set on five unrestricted acres in Winchester. Privately positioned and surrounded by natural beauty, this renovated berm-style residence offers the perfect balance of seclusion and sophistication. Inside, you'll find thoughtfully curated updates including fresh designer paint, updated flooring, and a bright, inviting interior that feels both modern and timeless. The

  Shawna Wever Wever Realty LLC

  119 Tower Ln, Winchester, KY 40391
• 

  

  /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
• 

  

  /31

  $310,000

  $20K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,624 Sq Ft

  28 Churchill Dr, Winchester, KY 40391

  ***Motivated Sellers*** Beautifully updated ranch on a new, fully finished walk out basement. 5 bedrooms, 2 being primary suites, one on the main level and one in the basement. This house is perfect for multigenerational living. New paint, floors, back splash, kitchen cabinets and granite counter tops. The fully finished basement has a newly added primary bedroom and bath. The updated bathroom

  Libby VanMeter Marshall Lane Real Estate - Lexington

  28 Churchill Dr, 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
• 

  

  /18

  $260,000

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  280 Pine Ridge Rd, Winchester, KY 40391

  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 expansion, this property is perfect for those dreaming of country living. Renovate the existing home or reimagine the space to fit your needs — the possibilities

  Derek Blankenship Keller Williams Commonwealth

  280 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /19

  $209,000

  • Land
  • 41.69 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 Keller Williams Commonwealth

  2697 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
• 

  

  /59

  $499,900

  • 4 Beds
  • 3 Baths
  • 5,646 Sq Ft

  16 Manor Dr, Winchester, KY 40391

  One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home!

  Zella Rosenthal Tom Goebel & Company

  16 Manor Dr, Winchester, KY 40391
• 

  

  /38

  $484,900

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,418 Sq Ft

  414 Fairholme Way, Winchester, KY 40391

  Step into a lifestyle where modern luxury and brand-new construction come together seamlessly in Fairholme Estates of Winchester. Perfectly positioned with golf course views and unforgettable sunset skies, this newly built home offers the kind of setting that turns ordinary evenings into your favorite part of the day—without sacrificing style, comfort, or convenience. Inside, soaring vaulted

  Morgan Withrow The Brokerage

  414 Fairholme Way, Winchester, KY 40391
• 

  

  /57

  $350,000

  • 4 Beds
  • 2 Baths
  • 3,261 Sq Ft

  443 S Maple St, Winchester, KY 40391

  Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make

  Terra Long Keller Williams Commonwealth

  443 S Maple St, Winchester, KY 40391
• 

  

  /38

  $319,900

  $10K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 2,327 Sq Ft

  162 French Ave, Winchester, KY 40391

  Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready

  Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  162 French Ave, Winchester, KY 40391
• 

  

  /24

  $365,900

  New Construction $4K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  206 Jett Dr, Winchester, KY 40391

  New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

  Mila Ensor Ensor Real Estate, LLC

  206 Jett Dr, Winchester, KY 40391
• 

  

  /10

  $550,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  107 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

  Shane Underwood Keller Williams Commonwealth

  107 Bella Shae Way, Winchester, KY 40391
• 

  

  /55

  $569,900

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft

  108 Bella Shae Way, Winchester, KY 40391

  Nearly new French country ranch that has been gently lived in. This classy home has magnificent curb appeal. When you walk through the front door you are welcomed by a tasteful foyer area. Stroll into the wide-open space of the great room with a towering, coffered ceiling and tons of natural light. The gas fireplace adds a nice focal point to the living space. The kitchen space is equipped with

  Vickie Skeens RE/MAX Elite Lexington

  108 Bella Shae 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

Frequently Asked Questions

What is the average home price in Winchester, KY?

Homes for sale in Winchester, KY have an average home price of $341,228.

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

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

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, 40361, 40516, 40353 and 40475.

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 $272,450. If you put a 20% down payment of $54,500 and had a 30-year fixed mortgage with an interest rate of 6.36%, your estimated principal and interest payment would be $1,360 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $58K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator.

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 Trends in Winchester, KY

On average, homes in Winchester, KY sell after 34 days on the market compared to the national average of 58 days. The median sale price for homes in Winchester, KY over the last 12 months is $259,950, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$259,950

Median Single Family Sale Price

$269,000

Median Townhouse Sale Price

$185,000

Average Price Per Sq Ft

$162

Number of Homes for Sale

81

Last 12 months Home Sales

322

Months of Supply

3.00

Median List Price

$272,450

Median Change From 1st List Price

3%

Median Home Sale Price YoY Change

11%