Newest Homes for Sale in Winchester, KY

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  /4

  $67,500

  • Land
  • 1.92 Acres
  • $35,156 per Acre

  12569 Ironworks Rd, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Or hold as investment property and watch this land grow in value. This lot containing 1.919 acres, offer unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own

  Kathryn Cheuvront Coldwell Banker McMahan

  12569 Ironworks Rd, Winchester, KY 40391
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  /36

  $262,500

  • 3 Beds
  • 2 Baths
  • 1,234 Sq Ft

  433 Wellington Way, Winchester, KY 40391

  Completely renovated and move-in ready! This 3-bedroom, 2-bath home offers 1,234 sq. ft. of stylish living with beautiful hardwood floors, fresh finishes, and a bright open layout. The vaulted ceiling in the main living area adds space and light, while the updated kitchen features modern cabinetry and new appliances. Both bathrooms have been tastefully redone, and every detail reflects quality

  Stephen Brashear Real Broker LLC

  433 Wellington Way, Winchester, KY 40391
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  /19

  $387,000

  • 3 Beds
  • 2.5 Baths
  • 2,636 Sq Ft

  300 Calmes Blvd, Winchester, KY 40391

  Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates Welcome to your dream home in the highly sought-after Calmes Estates neighborhood! This beautifully maintained 4-bedroom, 2.5-bath residence offers generous living space and a layout perfect for families or entertaining guests. Highlights: *Expansive open-concept living areas *Four spacious bedrooms with ample closet space *Two and a half

  Darrell Tackett Dream Maker Realty, LLC

  300 Calmes Blvd, Winchester, KY 40391
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  /30

  $349,000

  • 3 Beds
  • 2.5 Baths
  • 2,475 Sq Ft

  212 Woodbine Ct, Winchester, KY 40391

  Step right up - come on in! Its appeal is undeniable, both inside and out! Move-in ready. This well-maintained all-brick ranch on a full basement is full of charm and functionality! — Inside, you'll love having two separate living areas, 1 upstairs and 1 in the basement with a wood burning fireplace in both rooms. Enjoy the cold winter evenings in front of either of the fireplaces with family and

  Kathy Burton Coldwell Banker McMahan

  212 Woodbine Ct, Winchester, KY 40391
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  /13

  $262,500

  • 5 Beds
  • 3 Baths
  • 3,007 Sq Ft

  221 S Highland St, Winchester, KY 40391

  INVESTOR SPECIAL, could be a great option for an end of year cost seg study and bonus depreciation. You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in

  Joshua Lynch The Brokerage

  221 S Highland St, Winchester, KY 40391
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  /29

  $432,500

  • 8 Beds
  • 8 Baths
  • 4,000 Sq Ft

  17 W Lexington Ave, Winchester, KY 40391

  Investment Opportunity in the Heart of Downtown Winchester! Discover 17 W. Lexington Avenue — a converted commercial building now featuring 8 studio/one-bedroom apartments. Each unit includes a full kitchen and private bath, offering the perfect blend of comfort and convenience for tenants. This turn-key multifamily property is ideally situated in historic downtown Winchester, within walking

  Joshua Lynch The Brokerage

  17 W Lexington Ave, Winchester, KY 40391
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  /105

  $355,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 3 Baths
  • 2,520 Sq Ft

  145 Shanahan Ln, Winchester, KY 40391

  This 4-bedroom, 3-bath ranch on a basement offers over 2,500 sq ft of living space with modern updates, a welcoming layout and a safe neighborhood to live in. The large living room with cathedral ceilings flows into a well-appointed kitchen featuring ample counter space and newer appliances. New LVP flooring runs throughout the main level, while new patio doors open to a large deck—perfect for

  Josh Wood Freedom Realty & Property Management

  145 Shanahan Ln, Winchester, KY 40391
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  /53

  $279,500

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  724 Terry Dr, Winchester, KY 40391

  Charming Split-Level Home in a Peaceful Winchester Neighborhood Discover this beautiful 3-bedroom, 2 full bath split-level home featuring a cozy finished basement perfect for relaxing or entertaining. Enjoy both front and rear porches, ideal for morning coffee or evening gatherings. The spacious, fenced-in backyard offers privacy and room to play, garden, or unwind. Nestled in a quiet

  Darrell Tackett Dream Maker Realty, LLC

  724 Terry Dr, Winchester, KY 40391
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  /41

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft

  118 Windridge Dr, Winchester, KY 40391

  Imagine spending summers in your own private backyard retreat, complete with an in-ground pool featuring a newer liner, pump, and filter, secure iron fencing, and a roomy concrete patio that's ideal for relaxing or entertaining. This well-cared-for brick ranch in Windridge offers 3 bedrooms, 2 full baths, and hardwood and tile floors throughout with no carpet. Inside, the kitchen offers generous

  Michelle Blackburn RE/MAX Creative, Winchester

  118 Windridge Dr, Winchester, KY 40391
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  /18

  $209,900

  • 3 Beds
  • 1 Bath
  • 1,074 Sq Ft

  245 Ecton Rd, Winchester, KY 40391

  Welcome to this fully updated home that is cozy and full of character. Featuring brand new central heating and air, electric, drywall, spray foam insulation, kitchen cabinets, water heater, and stunning hardwood floors throughout. This beautiful kitchen boasts all brand new appliances, butcher block countertops, sage green cabinets, a 30 inch farmhouse sink, and also features a 6 foot island

  Anthony Gigilo ListWithFreedom.com

  245 Ecton Rd, Winchester, KY 40391
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  /13

  $1,300,000

  345 Providence Ln, Winchester, KY 40391

  120 Acres of Scenic Farmland in Winchester, KY. Discover the beauty and tranquility of country living on this remarkable 120-acre farm nestled in the heart of Clark County, Kentucky. Featuring a picturesque mix of rolling pastureland, mature woodlands, and pond, this property offers endless possibilities for farming, livestock, recreation, or building your dream home. Conveniently located just

  Megan McCoy Keller Williams Legacy Group

  345 Providence Ln, Winchester, KY 40391
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  /42

  $319,000

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  410 Corinne Ct, Winchester, KY 40391

  Charming Ranch-Style Home with Lots of Room- Step inside this 8 year old beautiful 1,604 sq. ft. ranch-style home featuring 9-foot ceilings and an open, inviting layout. With 3 comfortable bedrooms and a large, laundry room and back hallway, this home offers both style and functionality. The spacious living areas are enhanced by wood and tile flooring, adding a modern touch and easy maintenance.

  Shelly Sutton Kentucky Realty Group, LLC

  410 Corinne Ct, Winchester, KY 40391
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  /6

  $49,500

  • Land
  • 0.98 Acre
  • $50,510 per Acre

  204 Wigeon Ct, Winchester, KY 40391

  Choose your preferred builder to construct your dream home in Mallard Place. Located in a quiet cul-de-sac at the rear of the subdivision. Only a 20 minute drive to Hamburg/Lexington and only a 5 minute drive to the Winchester Bypass. Enjoy the serenity of living in a private setting AND the convenience of being close to schools, shopping and I-64 and I-75.

  Jim Woodrum RE/MAX Creative, Winchester

  204 Wigeon Ct, Winchester, KY 40391
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  /35

  $349,000 Open Sun 1:30PM - 3:30PM

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

  121 Fitch Ave, Winchester, KY 40391

  This beautifully updated 4-bedroom, 3-bath ranch home includes a private mother-in-law suite, offering flexible living options for guests or extended family. With 2,100 square feet of inviting living space and an attached two-car garage, this home perfectly combines timeless charm with thoughtful modern updates. Conveniently located just minutes from the interstate close to Lexington, it offers

  Ashley Spencer Keller Williams Commonwealth

  121 Fitch Ave, Winchester, KY 40391
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  /53

  $275,000 Open Sun 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,521 Sq Ft

  174 Hidden Grove Ln, Winchester, KY 40391

  Welcome home to your Kentucky River retreat! This freshly remodeled 2-bedroom, 2-bath charmer offers two inviting covered decks with beautiful river views, a fenced yard for pets or play and even a personal lift for easy access. Inside, enjoy warm, modern updates, with a bright open floor plan. All new flooring, kitchen, baths and much more! Perfect for full-time living or a peaceful getaway just

  Kathryn Cheuvront Coldwell Banker McMahan

  174 Hidden Grove Ln, Winchester, KY 40391
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  /19

  $294,900 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,966 Sq Ft

  729 Wayland Dr, Winchester, KY 40391

  This charming 3-bedroom, 2-bath split level home offers the perfect blend of comfort and convenience-located just minutes from Lexington's popular Hamburg area with endless shopping, dining and entertainment options right at your fingertips! Step inside to find a beautifully updated kitchen featuring brand-new granite countertops and a stylish new island, perfect for family meals or entertaining

  Brittany Beer EXP Realty, LLC

  729 Wayland Dr, Winchester, KY 40391
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  /8

  $25,000

  • Land
  • 0.1 Acre
  • $250,000 per Acre

  61 Melbourne St, Winchester, KY 40391

  Opportunity is knocking to build your dream home or investment property on this 0.1035 -acre residential lot at 61 Melbourne St, located in the North Park neighborhood right cross the street from the park and easy access to local amenities, schools, and roadways. With public utilities available, this lot offers endless possibilities for new construction or future development, providing a great

  Brian Lewis Guide Realty, Inc.

  61 Melbourne St, Winchester, KY 40391
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  /14

  $129,800

  • Land
  • 2.3 Acres
  • $56,435 per Acre

  110 Knox Ct, Winchester, KY 40391

  The largest and most desirable lot in The Reserve is now available! Nestled in a cul-de-sac, this 2.3 acre tract offers exceptional views of Bluegrass farmland. Build your custom dream home and watch the sun set over the pond, right from your porch. Located in one of Winchester's newest luxury subdivisions, featuring carefully crafted guidelines to preserve the community's character. All of this

  Amanda Thomas The Agency

  110 Knox Ct, Winchester, KY 40391
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  /87

  $829,000

  • 4 Beds
  • 3.5 Baths
  • 4,345 Sq Ft

  1701 Gay Evans Rd, Winchester, KY 40391

  Move into INSTANT equity Listed BELOW appraisal! This 4bd 4bath home has 2 BONUS ROOMS, a pool PLUS an attached and detached garage with finished space! This is a MUST see! Your dream country retreat awaits! Nestled on 8+ scenic acres, this stunning brick ranch offers the perfect blend of modern efficiency, functional living space, and peaceful country charm. A brand-new geothermal heating and

  

  Nora Williams

  Keller Williams Commonwealth

  (859) 544-2514

  1701 Gay Evans Rd, Winchester, KY 40391
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  /21

  $195,500

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft

  109 Quail Ridge Rd, Winchester, KY 40391

  Move-In Ready Brick Townhome with Garage and Fireplace Step into this charming brick townhome offering comfort, style, and convenience in every detail. The spacious living room features a cozy fireplace, soft neutral tones, and natural light that make it easy to feel at home. The open layout flows to the kitchen and dining area, creating the perfect setting for everyday living or entertaining

  Kim Dice EXP Realty, LLC

  109 Quail Ridge Rd, Winchester, KY 40391
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  /19

  $197,500

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft

  111 Quail Ridge Rd, Winchester, KY 40391

  Move-In Ready Brick Townhome with Garage and Fireplace Step into this charming brick townhome offering comfort, style, and convenience in every detail. The spacious living room features a cozy fireplace, soft neutral tones, and natural light that make it easy to feel at home. The open layout flows to the kitchen and dining area, creating the perfect setting for everyday living or entertaining

  Kim Dice EXP Realty, LLC

  111 Quail Ridge Rd, Winchester, KY 40391
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  /12

  $199,000

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  175 Magnolia St, Winchester, KY 40391

  Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is

  A. Rebecca Woods Woods Realty Group

  175 Magnolia St, Winchester, KY 40391
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  /31

  $234,000

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  209 Allan Place, Winchester, KY 40391

  Charming 3 Bedroom Home with Vaulted Ceilings and Wooded Views Welcome to this inviting 3-bedroom, 2-bath home offering an open-concept layout filled with natural light and soaring vaulted ceilings. The spacious living area flows seamlessly into the kitchen and dining spaces—perfect for both everyday living and entertaining. Enjoy peace of mind with a brand-new HVAC system, Gutter guards

  Julie Wiggington RE/MAX Creative, Winchester

  209 Allan Place, Winchester, KY 40391
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  /31

  $274,900

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  407 Corinne Ct, Winchester, KY 40391

  Welcome to 407 Corinne Court a beautifully maintained 3-bedroom, 2-bath all-electric home offering a perfect blend of comfort, style, and functionality. This one-level open-concept ranch sits on a crawl space foundation with a brick and vinyl exterior and features an attached two-car garage. Step inside to find fresh paint throughout, new carpet in the living room and bedrooms, and hardwood

  Shane Underwood Keller Williams Commonwealth

  407 Corinne Ct, Winchester, KY 40391
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  /79

  $499,000

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

  1410 Dry Fork Creek Rd, Winchester, KY 40391

  This breathtaking 92.3 +/- acre turnkey property is a nature lover's dream, offering endless opportunities for recreation, relaxation, and country living at its finest. Enjoy gently rolling terrain with a perfect blend of pasture, woods, and scenic trails, along with approximately one mile of road and creek frontage in a peaceful, private setting. Roughly 25 acres of hay field provide excellent

  Skyler Lewis Dream Maker Realty, LLC

  1410 Dry Fork Creek Rd, Winchester, KY 40391
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  /34

  $325,000

  • 2 Beds
  • 1 Bath
  • 1,531 Sq Ft

  1508 Ford Hampton Rd, Winchester, KY 40391

  Welcome home to this adorable 2 bedroom, 1 bathroom farmhouse on 5 peaceful acres. Inside, the layout is open and inviting with LVP and hardwood flooring throughout with a tiled bath. The kitchen and family room flow together and feature beautiful exposed wood beams that are hundreds of years old and reclaimed from an old church. A wood-burning stove in the family room adds warmth and character

  Michelle Blackburn RE/MAX Creative, Winchester

  1508 Ford Hampton Rd, Winchester, KY 40391
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  /47

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft

  23 Kittison Dr, Winchester, KY 40391

  ONE-OWNER BRICK RANCH HOME!! Now that I have your attention, schedule a showing quickly, this one won't last long!! This cozy home has 3 spacious bedrooms, 2 bath, and a family room and kitchen area that are wonderful for family gatherings. You will love the beautiful hardwood floors throughout the home. Don't forget the garage /workshop area out back with room to grow if needed.

  Teresa Richmond Freedom Realty & Property Management

  23 Kittison Dr, Winchester, KY 40391
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  /23

  $218,500

  • 3 Beds
  • 2.5 Baths
  • 1,348 Sq Ft

  363 Silverton Way, Winchester, KY 40391

  Unique Setting... Unlike Any Other! Wake up to the beauty of the surrounding countryside every single day. This 3-bedroom, 2.5-bath townhome is nestled in the desirable Royal Oaks Village, just one mile from I-64, making it a perfect location for both homeowners and renters alike. This low-maintenance property features tile flooring in the foyer, kitchen, and baths. The kitchen comes fully

  Kim Dice EXP Realty, LLC

  363 Silverton Way, Winchester, KY 40391
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  /32

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  528 Estes Dr, Winchester, KY 40391

  Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
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  /80

  $524,000

  • 3 Beds
  • 2.5 Baths
  • 4,933 Sq Ft

  160 Agawam Rd, Winchester, KY 40391

  Welcome to this beautifully maintained brick ranch home set on a spacious and private 5-acre fenced lot. This versatile property offers the perfect blend of comfort, functionality, and rural charm - ideal for families, hobby farmers, or equestrian enthusiasts. Inside, you'll find 3 bedrooms and 3 bathrooms with a fully finished basement that offers ample space for additional bedrooms, a home gym,

  Megan McCoy Keller Williams Legacy Group

  160 Agawam Rd, Winchester, KY 40391
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  /19

  $225,000

  • Land
  • 24 Acres
  • $9,375 per Acre

  3934 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Wonderful 24 acre retreat with gently sloping land, and a creek bed running thru the front portion of the lots (6.1 acre parcel & 18.4 acre parcel at the rear). Build your home/farm or just use as recreational or farm land until you do. 1 !/2 miles to !st Mountain Parkway exit#10. 12 miles to I-64. See attached pictures & plat/overhead pictures.

  Travis Emnett Top Ten Realty

  3934 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  /24

  $369,000

  • 4 Beds
  • 2.5 Baths
  • 2,811 Sq Ft

  446 Tremont Ln, Winchester, KY 40391

  Agent is Seller. 2800 square feet with four bedrooms and 2-1/2 baths. A large corner lot with side entry 2 car garage. Walkout patio, remodeled front porch, fully privacy fenced back yard, upgraded hot-water heaters, Upgraded fully insulated garage with steel back insulated door, walk in master closet, two story entry, and gas fireplace are just a few of the features in this home. Call today

  Dylan Langdon The Agency

  446 Tremont Ln, Winchester, KY 40391
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  /31

  $389,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  133 Shala-Mar Rue, Winchester, KY 40391

  Charming 3 Bedroom, 2 Bath Ranch Near Hamburg - Fully Renovated! Don't miss this beautifully updated 3-bedroom, 2-bath ranch-style home located just minutes from Hamburg! This move-in ready gem features brand new windows, siding, gutters, roof, and exterior doors, ensuring both curb appeal and peace of mind. Step inside to a spacious, light-filled living room—perfect for entertaining. The

  Nena Honaker Tom Goebel & Company

  133 Shala-Mar Rue, Winchester, KY 40391
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  /27

  $182,000

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft

  6 Monroe Ave, Winchester, KY 40391

  Charming and Updated Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a beautifully maintained 3-bedroom, 2-bath home full of character and modern touches. Step inside to find an inviting family room with an updated shiplap fireplace surround, perfect for cozy evenings. The kitchen is filled with natural light and features granite countertops, making it both stylish and functional.

  Lindsey Bivens Berkshire Hathaway de Movellan Properties

  6 Monroe Ave, Winchester, KY 40391
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  /34

  $330,000

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

  213 Orchid Ct, Winchester, KY 40391

  Kasey McCarty 5.23 Real Estate

  213 Orchid Ct, Winchester, KY 40391
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  /30

  $230,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  2721 Pretty Run Rd, Winchester, KY 40391

  Back on market due to buyer financing, no fault of the seller! Situated on 5 scenic acres along a highly sought-after country road, this 3-bedroom, 2-bath property presents an excellent opportunity to create your dream rural retreat. The home features a functional layout with a spacious living area, an eat-in kitchen, and a primary suite with its own bath. Two additional bedrooms offer

  Michelle Blackburn RE/MAX Creative, Winchester

  2721 Pretty Run Rd, Winchester, KY 40391
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  /47

  $372,900

  • 4 Beds
  • 3 Baths
  • 2,105 Sq Ft

  114 Mallard Ln, Winchester, KY 40391

  Nestled in a quiet cul-de-sac just minutes from shopping, dining, and the interstate, this unique ranch-style home offers a space, flexibility, and convenience. Originally designed as a duplex, the property has been thoughtfully renovated and modernized for an easy lifestyle. The main living area welcomes you with a light-filled, open concept layout featuring beautiful hardwood floors, a

  

  Robin Jones

  Keller Williams Legacy Group

  (859) 809-3100

  114 Mallard Ln, Winchester, KY 40391
• 

  

  /36

  $434,500

  • 4 Beds
  • 2.5 Baths
  • 2,747 Sq Ft

  134 Fontaine Blvd, Winchester, KY 40391

  Some homes are just houses—but this one was built for connection, creativity, and meaningful moments. Located in the desirable Oak Hill neighborhood, just minutes from GRC High School, this meticulously maintained 4-bedroom, 2.5-bath home offers the space and flexibility today's families are looking for. Formerly home to the beloved "2 Momma's Cooking for You," the property features a fully

  Craig Bridgewater Bridgewater Real Estate

  134 Fontaine Blvd, Winchester, KY 40391
• 

  

  /36

  $319,900

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

  128 Cherokee Dr, Winchester, KY 40391

  **Open House Sunday 11/16 1-3PM** 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, and exceptional curb appeal and charm, this home is just waiting

  

  Tyler Hurst

  Thwaites Realtors LLC

  (859) 681-9697

  128 Cherokee Dr, Winchester, KY 40391
• 

  

  /8

  $1,500,000

  1015 Old Stone Church Rd, Winchester, KY 40391

  Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights

  Walker Mack Bluegrass Property Exchange

  1015 Old Stone Church Rd, Winchester, KY 40391

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