Winchester, KY Houses for Sale

• 

  

  

  /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
• Explore Winchester

• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
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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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  /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
• 

  

  /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
• 

  

  /29

  $344,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,858 Sq Ft

  23 Windridge Dr, Winchester, KY 40391

  Welcome home!!! This beautifully updated all-brick ranch that perfectly blends charm and modern upgrades in a well established, desirable neighborhood is sure to please. Step inside to a bright open-concept living space featuring luxury vinyl flooring, a stunning wood-burning fireplace, and exposed wood ceiling beams that create a warm, inviting atmosphere in the spacious family room. The

  Holly Goeing The Agency

  23 Windridge Dr, Winchester, KY 40391
• 

  

  /72

  $406,900

  New Construction

  • 3 - 6 Beds
  • 2.5 - 5.5 Baths
  • 2,570 Sq Ft

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

  Unleash your creativity with the Jackie floor plan, a flexible and thoughtfully designed new construction home that empowers you to shape your ideal living space. Built by one of the most trusted home builders in Central Kentucky, the Jackie is a standout choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space, versatility, and modern

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824254, Winchester, KY 40391
• 

  

  /5

  $365,900

  New Construction $4K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft

  204 Jett Dr, Winchester, KY 40391

  New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

  Mila Ensor Ensor Real Estate, LLC

  204 Jett Dr, Winchester, KY 40391
• 

  

  /52

  $334,900

  $5K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft

  228 Holiday Rd, Winchester, KY 40391

  Back on the market at no fault of the sellers. Don't miss your chance to own this beautifully updated split-level home in Holiday Hills! Featuring 4 bedrooms and 2 full baths, this home offers a bright, open-concept kitchen and living area perfect for both everyday living and entertaining. Thoughtfully updated in recent years, the home features newer flooring, fresh paint, updated cabinets and

  Caroline Mucci CENTURY 21 Commonwealth R E

  228 Holiday Rd, Winchester, KY 40391
• 

  

  /33

  $350,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,310 Sq Ft

  38 N Burns Ave, Winchester, KY 40391

  Welcome to this beautiful new home in downtown Winchester! The open-concept design flows into a gorgeous kitchen w/granite countertops, gas stove, stainless appliances, and lots of cabinets. A first-floor bedroom w/private bath offers convenience flexibility. Upstairs, you'll find three generously sized bedrooms, each w/large closets, plus motion-activated hallway lighting. A covered back porch

  Trina Penn RE/MAX Creative Realty

  38 N Burns Ave, Winchester, KY 40391
• 

  

  /31

  $329,900

  $18K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  110 Powe Dr, Winchester, KY 40391

  This 4 Bedroom, 3 Bath home is quietly nestled within the Greenfield subdivision. Prime location just off the Winchester Bypass. This property has so much to offer. Updates can be seen throughout. Large first floor primary bedroom with on-suite and walk in closet, spacious family room, large yard with mature trees as well as widened driveway for additional parking, above ground pool with duel

  Michael Hilario The Agency

  110 Powe Dr, Winchester, KY 40391
• 

  

  /23

  $324,900

  $45K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,868 Sq Ft

  225 Plantations Dr, Winchester, KY 40391

  Welcome to 225 Plantations Drive, a beautifully maintained home in the desirable Royal Oaks Subdivision. This charming three-bedroom, two-and-a-half-bath residence is in wonderful condition and move-in ready! This is home comes with a wonderful floorplan that has a primary bedroom with built-in's on the first floor, Kitchen with granite and stainless appliances and deck has been updated with Trex

  John Wilson Bluegrass Properties Group

  225 Plantations Dr, Winchester, KY 40391
• 

  

  /49

  $345,000

  $15K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,628 Sq Ft

  221 Moundale Ave, Winchester, KY 40391

  Step back in time as you walk up the stone steps into this beautiful 3 bed 2.5 bath house. This house has been very well maintained and offers many updates. You get the best of both worlds the craftsmanship of an older home with all the newer amenities. Hardwood, tile and brick floors throughout the house with Granite countertops, This house sits on a lot and a half. The owners have recently

  Andrew Fugitt Coldwell Banker McMahan

  221 Moundale Ave, Winchester, KY 40391
• 

  

  /55

  $359,900

  • 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
• 

  

  /55

  $329,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft

  1291 Muddy Creek Rd, Winchester, KY 40391

  Rare opportunity with TWO lots!! This cozy ranch home, originally built in 1952, but was completely remodeled down to the studs in 2023 (per Seller), offering the charm of an established home with the feel of modern construction. The open concept floor plan features a spacious family room flowing seamlessly into the kitchen, perfect for every day, living and entertaining. The layout provides

  Terri McGraw FC Tucker Bluegrass

  1291 Muddy Creek Rd, Winchester, KY 40391
• 

  

  /43

  $319,900

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft

  3622 Stamper Dr, Winchester, KY 40391

  This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. With recently installed vinyl siding, gutters and gutter guard properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming

  Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
• 

  

  /26

  $349,900

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  614 Colby Ridge Blvd, Winchester, KY 40391

  Welcome to this beautifully maintained 4 bed 2.5 bath home built in 2020 offering the perfect blend of modern design and everyday comfort. Open-concept once you step inside with lots of space. The kitchen and dining offers entertainment space along with the back deck. Check out this house. Located right behind Kroger close to everything and more.

  Stacey Dunaway HomeLand Real Estate Inc - Mt Sterling

  614 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /60

  $395,000

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,310 Sq Ft

  382 S Main St, Winchester, KY 40391

  Spacious and full of character, this unique 4 bedroom, 3 bath home sits on a corner lot on South Main right across from the iconic South Main Grocery. Inside, you are welcomed by a two story foyer and a layout that offers flexibility with a living room, main level bedroom, full bath, and a dining room that could also function as an office with double doors. The kitchen has space for eat in dining

  Michelle Blackburn RE/MAX Creative, Winchester

  382 S Main St, Winchester, KY 40391
• 

  

  /44

  $349,500

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft

  221 W Hickman St, Winchester, KY 40391

  Step into a home where history and beauty meet in the most charming way. This stunning, fully remodeled historic home offers over 2600 square feet of thoughtfully renewed living space, blending timeless character with elegant modern updates. From the moment you walk inside, you'll feel the warmth and romance of a home that has been lovingly restored while still honoring its original charm. Large,

  Brandon Hedinger Keller Williams Bluegrass Realty

  221 W Hickman St, Winchester, KY 40391

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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

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%