Winchester, KY Homes for Sale with Garage

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  /67

  $699,000

  • 3 Beds
  • 4 Baths
  • 4,123 Sq Ft

  1775 Irvine Rd, Winchester, KY 40391

  Just 12 minutes from Lexington, own the most charming home atop a scenic hill at Blue Ridge Manor, a breathtaking 5.13 acre retreat where modern comfort meets classic elegance. As you drive up the long, private driveway, you'll feel like you're entering your own exclusive retreat, a sanctuary of peace and tranquility. Lovingly maintained by its original owner for the past 30 years, this

  

  Oxana Lopetegui-Pineda

  Lifstyl Real Estate

  (859) 659-6462

  1775 Irvine Rd, Winchester, KY 40391
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  Explore Winchester

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  /48

  $398,000

  • 4 Beds
  • 4 Baths
  • 3,087 Sq Ft

  213 Honeysuckle Ln, Winchester, KY 40391

  Welcome to one of Winchester's most established neighborhoods. This charming 2 story offers 4 bedrooms, 2 full baths, and 2 half baths, one in the finished basement. The layout features cozy nooks throughout the second story and a recently added bedroom over the garage with its own mini split hvac, perfect for guests, a home office, or creative space. The finished basement provides room for

  Shari Frasure Keller Williams Commonwealth

  213 Honeysuckle Ln, Winchester, KY 40391
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  $3,175,000

  • 8 Beds
  • 7.5 Baths
  • 12,702 Sq Ft

  4664 Lexington Rd, Winchester, KY 40391

  Visitors to the farm are greeted by a substantial stone entry before traveling a gently winding path to the circular drive. There rests the grand residence, offering an ideal setting for entertaining family & friends. Ten minutes from Hamburg, the farm is located on the convenient Lexington/Winchester Road. Lovely views abound and the property retains remarkable privacy. The 13,500 square foot

  Zach Davis Kirkpatrick & Company

  4664 Lexington Rd, Winchester, KY 40391
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  /75

  $535,000

  • 5 Beds
  • 3.5 Baths
  • 3,741 Sq Ft

  130 Winterberry Cir, Winchester, KY 40391

  Welcome to this beautifully maintained modern home located in the highly sought-after Royal Oaks Estates, perfectly positioned on the edge of Winchester with quick access to shopping, dining, and more. From the moment you step inside, you'll be captivated by the soaring vaulted ceilings in the central great room—an impressive space filled with natural light and designed for both comfort and

  Josh Wood Freedom Realty & Property Management

  130 Winterberry Cir, Winchester, KY 40391
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  /85

  $650,000

  • 4 Beds
  • 3.5 Baths
  • 4,779 Sq Ft

  180 Casa Landa Way, Winchester, KY 40391

  This stately yet inviting residence in the highly desirable Stoney Brook subdivision offers the perfect blend of elegance and comfort. Thoughtfully designed for everyday living and entertaining, the home features generously sized rooms throughout.The main level includes formal living and dining spaces, a convenient half bath, and a beautifully appointed kitchen with granite countertops,

  Janna Chalfant Smith United Real Estate Bluegrass

  180 Casa Landa Way, Winchester, KY 40391
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  /120

  $559,900

  • 6 Beds
  • 3.5 Baths
  • 3,846 Sq Ft

  1953 Cabin Creek Rd, Winchester, KY 40391

  ***Click on the Virtual Tour section to see the video walk through!*** This unique property includes not only one, but two beautiful homes in the heart of Kentucky Bluegrass country. The first home is a brick ranch with a covered front porch and back patio that overlook this beautiful piece of farm land. This 2046 sq ft home contains 3 bedrooms and 2 full baths with a large great room in the

  Josh Wood Freedom Realty & Property Management

  1953 Cabin Creek Rd, Winchester, KY 40391
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  /99

  $749,000

  • 4 Beds
  • 4 Baths
  • 4,644 Sq Ft

  110 Camelot Dr, Winchester, KY 40391

  Don't miss this rare opportunity to abide in one of Winchester's finest locations, Camelot Drive. A hidden gem tucked away in the back of Hampton Manor, this home boasts space and privacy on an idyllic cul-de-sac just off Boone Avenue. Details such as crown molding, built-in cabinetry, high ceilings, 2 fireplaces, transom windows, and hardwood floors fill this home with character and charm.

  Joyce Ratliff Tom Goebel & Company

  110 Camelot Dr, Winchester, KY 40391
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  /39

  $472,000

  • 3 Beds
  • 2 Baths
  • 2,727 Sq Ft

  865 Pretty Run Rd, Winchester, KY 40391

  Situated on 1.5 acres along a sought after country road, this one level home features a split bedroom layout with a primary suite that includes an en suite bath and walk in closet. The living room offers vaulted ceilings, hardwood floors, and a gas log fireplace, opening to a dining area and an eat in kitchen. A sunroom provides additional living space with skylights and views of the backyard.

  Shane Underwood Keller Williams Commonwealth

  865 Pretty Run Rd, Winchester, KY 40391
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  /80

  $574,900

  • 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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  /46

  $629,000

  • 3 Beds
  • 3.5 Baths
  • 2,900 Sq Ft

  433 Fairholme Way, Winchester, KY 40391

  This elegant ranch on a basement offers refined main-level living with upscale finishes throughout. The chef's kitchen is a standout featuring double ovens, custom soft-close cabintry, granite countertops, a large island with seating, a spacious walk-in pantry for entertaining and everyday ease. Primary bedroom has Amish cutom built closet. Enjoy quiet evenings on the covered front porch with

  Kathryn Cheuvront Coldwell Banker McMahan

  433 Fairholme Way, Winchester, KY 40391
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  /52

  $549,900

  • 4 Beds
  • 2 Baths
  • 2,940 Sq Ft

  5515 Van Meter Rd, Winchester, KY 40391

  Welcome to your dream home, perfectly nestled in a highly desired location. This stunning property spans a generous 5 acres, offering an idyllic setting for homesteading. Experience the best of country living with the convenience of nearby amenities.The home boasts beautiful views that will take your breath away every morning. Imagine waking up to the serene beauty of nature, right at

  Robyn Bradley Woods Realty Group

  5515 Van Meter Rd, Winchester, KY 40391
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  /67

  $549,000

  • 4 Beds
  • 2.5 Baths
  • 3,989 Sq Ft

  415 David Ln, Winchester, KY 40391

  Location, location, location!! This house, 415 David Lane, is located in the most sought after neighborhood, Stoneybrook. It is approximately 20 minutes from the Hamburg area of Lexington and minutes from the I-75 corridor. Enter the house from the welcoming front porch to a entryway and notice immediately the gleaming hardwood floors and the stairway leading to the second floor. The primary

  Craig Bridgewater Bridgewater Real Estate

  415 David Ln, Winchester, KY 40391
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  /17

  $445,000

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft

  104 Colby Hills Dr, Winchester, KY 40391

  Welcome to this beautiful ranch home, located in this desirable Colby Hill subdivision this house has been updated with new interior painting, new flooring, new kitchen cabinets, and tops, new bathrooms, large new lighting, 2 car garage, 2 fireplaces, living room, family room, dinning area, large new deck ,all this on a large corner lot. Owner/Broker

  Garry Milton Milton and Associates Real Estate

  104 Colby Hills Dr, Winchester, KY 40391
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  /10

  $550,000

  • 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
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  /41

  $259,900

  • 3 Beds
  • 2.5 Baths
  • 1,544 Sq Ft

  315 Newcastle Ln, Winchester, KY 40391

  Nestled in a cul-de-sac in Winchester's Oakmont neighborhood, this 3-bedroom, 2.5-bath home offers comfort and convenience. The main level features vinyl plank flooring throughout, a spacious living room, and an eat-in kitchen, plus a laundry area and half bath. Upstairs, you'll find three generously sized bedrooms, including a primary suite with a walk-in closet and private bath. A second full

  Terra Long Keller Williams Commonwealth

  315 Newcastle Ln, Winchester, KY 40391
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  /6

  $171,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  102 W Hickman St, Winchester, KY 40391

  102 W Hickman St, Winchester, KY 40391Cozy and full of potential! This 11⁄2-story home offers 2 bedrooms and 1 bathroom, making it a great fit for a small household or as part of a rental investment portfolio. Currently used as a rental, the property features a functional layout with living spaces on the main floor and additional space upstairs. Located on a quiet street yet close to downtown

  David Espinosa Bluegrass Realty Pros, Inc

  102 W Hickman St, Winchester, KY 40391
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  /2

  $131,000

  • 2 Beds
  • 1 Bath
  • 804 Sq Ft

  206 Chaplin Ave, Winchester, KY 40391

  206 Chaplin Ave, Winchester, KY 40391Cozy and full of potential! This 11⁄2-story home offers 2 bedrooms and 1 bathroom, making it a great fit for a small household or as part of a rental investment portfolio. Currently used as a rental, the property features a functional layout with living spaces on the main floor and additional space upstairs. Located on a quiet street yet close to downtown

  David Espinosa Bluegrass Realty Pros, Inc

  206 Chaplin Ave, Winchester, KY 40391
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  /103

  $3,330,000

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 78-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
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  /71

  $419,000

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft

  188 Big Stoner Rd, Winchester, KY 40391

  Come home every day to this 2-story beauty! You need country life? Well here is it! A little over 1 acre to spread out & enjoy the outdoors w/farm views & beautiful sunsets in the evening. This home opens up to a huge living room with hardwood floors and a vaulted ceiling. Kitchen has all stainless steel appliances & granite counter tops. First floor has a primary suite and a bonus room

  Trina Penn RE/MAX Creative Realty

  188 Big Stoner Rd, Winchester, KY 40391
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  /36

  $360,000

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  208 Citation Ct, Winchester, KY 40391

  One owner, all electric, 2 BR/2Ba ranch with a bonus room that could be an office or a third bedroom. The open floor great room with ample windows to brighten it supports the handicapped features of the primary bedroom, primary bathroom, garage and more. Enjoy the large pantry off the kitchen area and the island that has room to slide a chair under. (see photos) Kitchen appliances include

  Garnett Davis Tom Goebel & Company

  208 Citation Ct, Winchester, KY 40391
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  /41

  $335,000

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

  118 Windridge Dr, Winchester, KY 40391

  Located in the Windridge neighborhood with easy access to both Bypass Rd and Boone Ave, this charming brick ranch offers 3 bedrooms, 2 full baths, and character throughout. Inside, you'll find hardwood and tile floors (no carpet!), a spacious kitchen with plenty of cabinet space that opens into the dining area and living room, complete with a cozy ventless gas fireplace. Step out back to your own

  Michelle Blackburn RE/MAX Creative, Winchester

  118 Windridge Dr, Winchester, KY 40391
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  $269,950

  • 3 Beds
  • 2 Baths
  • 1,247 Sq Ft

  3614 Stamper Dr, Winchester, KY 40391

  Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

  Darrell Tackett Dream Maker Realty, LLC

  3614 Stamper Dr, Winchester, KY 40391
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  /26

  $215,000

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  271 April Way, Winchester, KY 40391

  This charming 2 - story townhouse is in a prime location.. Welcome to this beautifully maintained 2 bedroom, 1.5 bath townhouse offering the perfect blend of comfort, style and convenience. Spread over two spacious levels, this home features an inviting living area, a modern kitchen with ample cabinetry and a cozy dining space-perfect for every day living or entertaining guests. Upstairs,

  Kimberly Fugate Keller Williams Commonwealth

  271 April Way, Winchester, KY 40391
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  /39

  $365,000

  • 4 Beds
  • 2.5 Baths
  • 2,929 Sq Ft

  219 Hampton Ave, Winchester, KY 40391

  Open House-Sun 2-4 p.m. This beautiful brick ranch-style home sits on a generous .31 acre lot -property extends to the right, well beyond the fenced area, reaching to the tree stump & pink flag, offering more space, & on a quiet dead end street with mature trees. The property features a natural stone front and partial stone skirt(added in 2023), enhancing its curb appeal. Inside, you'll find

  Jo Gawthrop Keller Williams Bluegrass Realty

  219 Hampton Ave, Winchester, KY 40391
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  /37

  $399,900

  • 4 Beds
  • 3 Baths
  • 2,991 Sq Ft

  576 Marseille Blvd, Winchester, KY 40391

  **Priced to sell and well below the attached appraisal dated 7/16/2025.** Welcome to this beautifully maintained 4-bedroom, 3-bathroom home with a walkout basement, nestled in the desirable Oak Hill subdivision. Thoughtfully designed and extensively landscaped both front and back, this home offers the perfect blend of comfort, functionality, and outdoor living. Step inside to discover spacious

  James Turek Bluegrass Sotheby's International Realty

  576 Marseille Blvd, Winchester, KY 40391
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  $374,900

  • 3 Beds
  • 2.5 Baths
  • 1,750 Sq Ft

  714 Concord Ave, Winchester, KY 40391

  This beautiful modern home is conveniently located in the Colby Ridge subdivision with easy access to all that Winchester has to offer. From the comfortable front porch, take a step inside to enjoy the open floor plan great room with living space, dining space and a stunning kitchen. Also on the first floor is a bonus family room area that could be used as a small bedroom (without a closet) as

  Josh Wood Freedom Realty & Property Management

  714 Concord Ave, Winchester, KY 40391
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  /35

  $318,000

  • 3 Beds
  • 2.5 Baths
  • 1,903 Sq Ft

  329 Hanover Dr, Winchester, KY 40391

  Welcome home to this well-maintained two-story home on an unfinished basement! This home features 3 bedrooms, 2 bathrooms, a bonus room overlooking the living room, kitchen with all the appliances to convey, basement is roughed in for a bathroom already as well. Outside you will find a covered front porch, spacious deck and a patio. Located right off the bypass in Winchester this property is

  Bradley Warford Century 21 Pinnacle

  329 Hanover Dr, Winchester, KY 40391
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  /64

  $989,000

  • 4 Beds
  • 2.5 Baths
  • 2,670 Sq Ft

  1110 Craig Crossing, Winchester, KY 40391

  Discover timeless elegance and modern luxury in this newly constructed residence, perfectly situated on over 2.5 acres in Winchester. With 2,670 sq ft of custom designed living space, this 4-bedroom, 2.5-bath home offers craftsmanship, high-end finishes, and exceptional outdoor living. White oak engineered hardwood flooring, moulding throughout, and exquisite details. The spacious great room

  Michael Hilario The Agency

  1110 Craig Crossing, Winchester, KY 40391
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  /64

  $369,900

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  309 Gallahadion Ct, Winchester, KY 40391

  This beautiful, new-construction home located in desirable Fairholme Estates is a must see!! Amazing open floor plan with kitchen granite countertops, a large island and upgraded Frigidaire Elite Stainless Appliances. The waterproof Pergo laminate flooring is throughout the home. The builder has installed window blinds throughout the home and stained the back deck. Don't miss the primary

  Josh Wood Freedom Realty & Property Management

  309 Gallahadion Ct, Winchester, KY 40391
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  /64

  $364,900

  • 3 Beds
  • 2 Baths
  • 1,612 Sq Ft

  616 Colby Ridge Blvd, Winchester, KY 40391

  This beautiful ranch home located in Colby Ridge Subdivision is a must see!! Located close to shopping, schools and the interstate and parkway. Amazing open floor plan with granite kitchen countertops, tile backsplash, walk-in pantry, a large island and upgraded Frigidaire Elite Stainless Appliances. The waterproof vinyl plank flooring is throughout the home. Don't miss the primary bedroom suite

  Josh Wood Freedom Realty & Property Management

  616 Colby Ridge Blvd, Winchester, KY 40391
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  $235,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  37 7th St, Winchester, KY 40391

  Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

  Andrew Fugitt Coldwell Banker McMahan

  37 7th St, Winchester, KY 40391
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  /31

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,201 Sq Ft

  210 Moss Ct, Winchester, KY 40391

  Nice 3 bedroom, 2 bath, all one level, ranch home! Convenient location! Nice patio to sit out back in the mostly privacy fenced in yard. Only needs a few panels to be completely fenced if desired. One car garage. Easy to maintain lot. Large kitchen. Good sized bedrooms. Windows, HVAC, and roof all replaced within the last 8 years. This will make someone a great home!

  Jason Townsend Kentucky Residential Real Estate, LLC

  210 Moss Ct, Winchester, KY 40391
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  /65

  $713,500

  • 6 Beds
  • 4.5 Baths
  • 6,243 Sq Ft

  418 David Ln, Winchester, KY 40391

  This impeccable house is a Buyer's Delight. Located in the most desirable residential neighborhood, Stoney Brook. Discover a serene retreat in this beautifully appointed home, offering spacious interiors and breathtaking outdoor spaces. Step into the front door and discover the soaring ceilings with beautifully appointed crown molding. The flowing space from the dining room to the great room to

  Craig Bridgewater Bridgewater Real Estate

  418 David Ln, Winchester, KY 40391
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  /14

  $265,000

  • 3 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  10 Upper St, Winchester, KY 40391

  Modern Ranch residence full un-finished basement, large lot.

  E. Clark Toleman Real Estate Appraisal Services

  10 Upper St, Winchester, KY 40391
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  /18

  $389,900

  • 3 Beds
  • 3 Baths
  • 2,516 Sq Ft

  110 Hampton Ave, Winchester, KY 40391

  Move-in ready mid- century brick ranch home! Features 3 bedrooms, 3 full baths, new kitchen with granite countertops, 3 woodburning fireplaces, formal dining or family room, full basement with huge rec room or space to have 4th bedroom, 1 car garage, 2 storage buildings & fenced in yard! Updates include windows, doors, metal roof, new paint inside & out, new flooring in basement & bedrooms, all

  Angie Conley Dixon Dixon Properties

  110 Hampton Ave, Winchester, KY 40391
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  /57

  $357,000

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft

  356 Boone Ave, Winchester, KY 40391

  Step into timeless charm with this beautifully renovated home on one of Winchesters most historic streets. Built over 100 years ago, this 3200 sq ft residence blends classic character with modern updates. You will love the updated kitchen featuring granite countertops, stainless appliances and plenty of space for cooking and entertaining in the large dining room. This home showcases re-tiled

  Nancy Smith Rector Hayden Realtors

  356 Boone Ave, Winchester, KY 40391
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  /37

  $1,249,500

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  700 Nick Ln, Winchester, KY 40391

  🚨 BIG PRICE DROP ALERT! 🚨 Motivated sellers are ready to make a deal—this is your chance to snag an unbeatable offer! 💰🏡Step into country living with this amazing 120-acre working farm! You'll love the brand-new 3-bedroom, 2.5-bath home that features an open floor plan, perfect for hanging out with family or hosting friends. It's got all the modern touches, so you

  Darrell Tackett Dream Maker Realty, LLC

  700 Nick Ln, Winchester, KY 40391
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  /33

  $339,000

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft

  1831 Kiddville Rd, Winchester, KY 40391

  Offering a perfect blend of modern comfort, energy efficiency, and country charm. Conveniently located just 1.3 miles from Exit 10 off the Bert T. Combs Mountain Parkway, this property provides easy access to both natural beauty and city amenities, with Downtown Winchester only 15 miles away and Natural Bridge State Park just 27 miles down the road. The living area features a cozy vent-free gas

  Joshua Davis The Agency

  1831 Kiddville Rd, Winchester, KY 40391
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  /20

  $207,500

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

  111 Quail Ridge Rd, Winchester, KY 40391

  Welcome Home - Comfortable Living or Smart Investment!Step into this inviting townhome, offering both spacious comfort and excellent investment potential. Featuring two bedrooms and two and a half bathrooms, this well-designed unit boasts a generous living area with a ventless fireplace, creating a warm, welcoming atmosphere.The home's layout connects the living room, dining area, and kitchen

  Kim Dice EXP Realty, LLC

  111 Quail Ridge Rd, Winchester, KY 40391
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  /21

  $205,000

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

  109 Quail Ridge Rd, Winchester, KY 40391

  Welcome Home - Comfortable Living or Smart Investment!Step into this inviting townhome, offering both spacious comfort and excellent investment potential. Featuring two bedrooms and two and a half bathrooms, this well-designed unit boasts a generous living area with a ventless fireplace, creating a warm, welcoming atmosphere.The home's layout connects the living room, dining area, and kitchen

  Kim Dice EXP Realty, LLC

  109 Quail Ridge Rd, Winchester, KY 40391

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