Winchester, KY Homes for Sale

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  $785,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft

  425 Alexis Way, Winchester, KY 40391

  Introducing the Highland, an elegant all-brick ranch home offering 4 bedrooms and 2.5 full baths in a thoughtfully designed split-bedroom layout. The spacious primary suite is a true highlight, featuring a luxurious tile shower, separate soaking tub, double vanities, and a large walk-in closet. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for

  Shane Underwood Keller Williams Commonwealth

  425 Alexis Way, Winchester, KY 40391
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  /4

  $137,500

  • Land
  • 3.94 Acres
  • $34,898 per Acre

  12569 Ironworks Rd, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it gows in value. Offering 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

  Kathryn Cheuvront Coldwell Banker McMahan

  12569 Ironworks Rd, Winchester, KY 40391
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  /19

  $125,000

  • Land
  • 4.01 Acres
  • $31,172 per Acre

  1940 Athens Boonesboro Rd, Winchester, KY 40391

  Escape to tranquility with this beautiful 4-acre lot in Clark County, offering the perfect setting to build your dream home. Tucked away on a quiet road, this property is surrounded by expansive farmland, ensuring ultimate privacy and peaceful living. A serene pond adds to the charm, providing a perfect spot to relax and enjoy the natural beauty of the land. This lot sits directly across from the

  Laura Sizemore Kentucky Land and Home

  1940 Athens Boonesboro Rd, Winchester, KY 40391
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  /17

  $439,000

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

  104 Colby Hills Dr, Winchester, KY 40391

  (Reducted 50,000) for fast sell. 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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  /3

  $380,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  230 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

  Rex Hall United Real Estate Bluegrass

  230 Evergreen Dr, Winchester, KY 40391
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  /22

  $270,000

  • 4 Beds
  • 2 Baths
  • 2,332 Sq Ft

  35 Cherokee Ct, Winchester, KY 40391

  Step into this 4-bedroom, 2 full bath split-foyer home, perfectly designed for comfortable everyday living. The upper level features three generously sized bedrooms, a full bath, a bright living room, kitchen, and dining area—ideal for gathering with family and friends. Just off the kitchen, enjoy easy access to the covered deck overlooking a spacious backyard. The lower level offers even more

  Brenda Rue Keller Williams Bluegrass Realty

  35 Cherokee Ct, Winchester, KY 40391
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  /2

  $110,000

  • Land
  • 0.32 Acre
  • $343,750 per Acre

  250 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  250 Duclair Dr, Winchester, KY 40391
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  /21

  $139,000

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft

  9 Linden Ave, Winchester, KY 40391

  Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval,

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
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  /54

  $312,000

  • 4 Beds
  • 1.5 Baths
  • 2,170 Sq Ft

  214 S Burns Ave, Winchester, KY 40391

  Own a beautifully maintained piece of Winchester, KY history on desirable South Burns Avenue. This charming home features an inviting wrap-around porch perfect for year-round enjoyment and outstanding curb appeal. Step into a warm and welcoming entryway where refinished hardwood floors flow throughout the main level. Original pocket doors open into the library, showcasing the home's timeless

  Christa Joynt Keller Williams Commonwealth

  214 S Burns Ave, Winchester, KY 40391
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  /36

  $379,000

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

  133 Shala-Mar Rue, Winchester, KY 40391

  Welcome to your next home in one of Clark County's most desirable neighborhoods—Shala Mar Estates! This beautifully updated 3-bedroom, 2-bathroom home offers the perfect blend of comfort, space, and modern convenience. Step into the expansive primary bedroom, a true retreat, complete with a stunning ensuite bathroom featuring a brand-new soaking tub and a separate tiled shower. The additional

  Nena Honaker Tom Goebel & Company

  133 Shala-Mar Rue, Winchester, KY 40391
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  /38

  $389,900

  • 4 Beds
  • 2 Baths
  • 2,659 Sq Ft

  6239 Old Boonesboro Rd, Winchester, KY 40391

  Welcome Home to the beautiful country! If you've been looking for quiet, space, and a place that truly feels like home, this charming Cape Cod on nearly 2 acres in Clark County checks all the boxes. Tucked into a peaceful rural setting yet conveniently located near I-75, I-64 and the Winchester Bypass, this property offers the best of country living with easy access to town. With over 2,600

  Kenya Woods United Real Estate Bluegrass

  6239 Old Boonesboro Rd, Winchester, KY 40391
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  /103

  $3,500,000

  • 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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  /2

  $369,900 New Construction

  • 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
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  /25

  $310,000

  • 2 Beds
  • 1 Bath
  • 1,170 Sq Ft

  398 Pine Ridge Rd, Winchester, KY 40391

  Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment you walk in. Enjoy the outdoors from the

  Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
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  /2

  $195,000

  6699 Boonesboro Rd, Winchester, KY 40391

  READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

  Jennifer Ray RE/MAX Elite Lexington

  6699 Boonesboro Rd, Winchester, KY 40391
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  /3

  $670,000 New Construction

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

  113 Bella Shae Way, Winchester, KY 40391

  Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen

  Shane Underwood Keller Williams Commonwealth

  113 Bella Shae Way, Winchester, KY 40391
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  $255,000

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft

  21 Virginia Ave, Winchester, KY 40391

  Nicely updated and offering plenty of functional space, this home gives you flexibility and room to grow. The main living area flows into an updated kitchen featuring modern finishes, new appliances, butcher-block countertops, and convenient access to the sunroom. Enjoy your morning coffee in the oversized sunroom, then step out to the fully fenced backyard — great for chickens, kids, pets,

  Emily Crump EXP Realty, LLC

  21 Virginia Ave, Winchester, KY 40391
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  /19

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,072 Sq Ft

  117 Buffalo Trace, Winchester, KY 40391

  Move-In Ready! 3 bedrooms, 2 bath, brand new kitchen cabinets with stylish butcher block counter tops, fresh light fixtures throughout, and durable, sleek laminate flooring. This home combines comfort and style with updates that make it truly shine. Perfect for families or first-time home buyers! Conveniently located in a great neighborhood. Owner/Agent

  Nena Honaker Tom Goebel & Company

  117 Buffalo Trace, Winchester, KY 40391
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  /13

  $1,250,000

  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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  /31

  $379,717

  • 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 3-bedroom, 2.5-bath residence offers generous living space and a layout perfect for families or entertaining guests. Highlights: *Expansive open-concept living areas *three 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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  /64

  $420,000

  • 5 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  1857 Ironworks Rd, Winchester, KY 40391

  Get a piece of Bluegrass heaven in this move-in ready modern farmhouse on just under 5acres in Clark County. Dreaming of the country life? This is it, originally built in 1865 this timeless home has been completely updated and seamlessly blended the history with modern elegant design and livability. Classic farmhouse style with tons of natural light that bring the outside in. Spacious great room

  Meredith Walker Bluegrass Sotheby's International Realty

  1857 Ironworks Rd, Winchester, KY 40391
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  /9

  $500,000

  • Land
  • 1.52 Acres
  • $328,947 per Acre

  1005 Early Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

  Whitney Ensor Ensor Real Estate, LLC

  1005 Early Dr, Winchester, KY 40391
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  /14

  $650,000

  • Land
  • 3 Acres
  • $216,667 per Acre

  205 Codella Dr, Winchester, KY 40391

  Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Real Estate

  205 Codella Dr, Winchester, KY 40391
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  /6

  $110,000

  • Land
  • 2.06 Acres
  • $53,398 per Acre

  1185 Craig Crossing Rd, Winchester, KY 40391

  Lot # 30 contains 2.058 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  1185 Craig Crossing Rd, Winchester, KY 40391
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  /21

  $249,900

  • 3 Beds
  • 1 Bath
  • 1,494 Sq Ft

  720 Estes Dr, Winchester, KY 40391

  This charming brick ranch is truly move-in ready. Offering 3 bedrooms, 1.5 baths, a welcoming living room, a cozy den, and kitchen with appliances, this home blends comfort and convenience with ease. Enjoy the natural light and peaceful views from the screened-in sunporch, perfect for relaxing. Updates include new kitchen flooring, refinished hardwood floors, and updated trim that gives the home

  Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  720 Estes Dr, 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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  /23

  $345,900

  • 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
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  /27

  $269,000

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

  222 Bracken Ct, Winchester, KY 40391

  Great flloor plan -- great location -- GREAT price! Nice open space on the first level with fully-equipped kitchen and dining area and a very generously-sized family room. Backs up to Ecton Road so you are not looking at the back of another house. Primary bedroom and laundry upstairs with two other bedrooms. All three bedrooms have walk-in closets! The storage building conveys. This home is less

  Jim Woodrum RE/MAX Creative, Winchester

  222 Bracken Ct, 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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  /33

  $215,000

  • 4 Beds
  • 1 Bath
  • 1,743 Sq Ft

  218 E Washington St, Winchester, KY 40391

  Motivated seller! Bring your offers. This home is a charming 4 bedroom 1 bath. It boasts a large bonus room which could be an office or 5th bedroom. This home offers a nice sized laundry room with space to add a second bathroom. This home has a nicely shaded fully fenced in back yard with a gate for easy accessibility . There is also a detached storage garage and a long driveway. Within walking

  Fernando Andrade Rector Hayden Realtors

  218 E Washington St, Winchester, KY 40391
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  /22

  $221,500

  • 4 Beds
  • 2 Baths
  • 1,370 Sq Ft

  521 Acadia Way, Winchester, KY 40391

  This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

  Tyler I Back The Brokerage

  521 Acadia Way, Winchester, KY 40391
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  /7

  $270,000

  • Land
  • 0.84 Acre
  • $321,429 per Acre

  800 Interstate Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat buyer to verify, zoned B-3. .84 acres located and visible at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property and or inspections sold as is. Buyer to verify water, gas, and electric locations and availability.

  Whitney Ensor Ensor Real Estate, LLC

  800 Interstate Dr, Winchester, KY 40391
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  /86

  $550,000

  • 4 Beds
  • 3.5 Baths
  • 3,848 Sq Ft

  125 Casa Landa Way, Winchester, KY 40391

  Stoney Brook Subdivision! Second time ever offered for sale. Beautiful two story brick home with first and second floor en-suites. Each of the 4 bedrooms has its own walk in closet. Formal family room and dinning rooms, great room with fireplace, breakfast area, all season room with natural lighting, and large flex space located on second floor. All of this setting on .40 of an acre lot with side

  Maggie Napier Napier Realtors

  125 Casa Landa Way, Winchester, KY 40391
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  /65

  $609,900

  • 5 Beds
  • 4 Baths
  • 4,515 Sq Ft

  6595 Mount Sterling Rd, Winchester, KY 40391

  INCREDIBLE! This custom-built home sits on 2.59 acres in a prime location just minutes from I-64 and perfectly positioned between Winchester and Mount Sterling. The main level features a grand formal dining room, a family room with a vaulted coffered ceiling, and an eat-in kitchen open to the living area for easy entertaining. You'll also find the first primary suite plus two additional bedrooms

  Brooke Otis Mullins RO&CO Real Estate

  6595 Mount Sterling Rd, Winchester, KY 40391
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  /39

  $612,900

  • 4 Beds
  • 5 Baths
  • 4,374 Sq Ft

  600 Boone Ave, Winchester, KY 40391

  Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the

  Holly Goeing The Agency

  600 Boone Ave, Winchester, KY 40391
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  /2

  $550,000

  • Land
  • 1.53 Acres
  • $359,477 per Acre

  33-41 Winn Ave, Winchester, KY 40391

  Discover a rare opportunity in downtown Winchester with this assemblage of four vacant lots being sold together as a single offering. Zoned L1 and totaling approximately 1.53 acres, this property presents exceptional potential for redevelopment, infill housing, multiunit residential, mixeduse, or commercial concepts in a central location. Situated just steps from local shops, restaurants,

  Bob Sophiea eXp Realty, LLC

  33-41 Winn Ave, Winchester, KY 40391
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  /19

  $189,500

  • 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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  /2

  $150,000

  • Land
  • 2.16 Acres
  • $69,444 per Acre

  120 Knox Ct, Winchester, KY 40391

  Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  120 Knox Ct, Winchester, KY 40391
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  /63

  $1,149,000

  • 3 Beds
  • 3.5 Baths
  • 3,672 Sq Ft

  2100 Irvine Rd Unit 40391, Winchester, KY 40391

  Seller will need 48 Hours to show, This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths,

  Mila Ensor Ensor Real Estate, LLC

  2100 Irvine Rd Unit 40391, Winchester, KY 40391
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  /47

  $452,500

  • 3 Beds
  • 2.5 Baths
  • 2,961 Sq Ft

  42 Mockingbird Valley Rd, Winchester, KY 40391

  This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons

  Markus Cross McCallie Real Estate

  42 Mockingbird Valley Rd, Winchester, KY 40391

Showing Results 41 - 80, Page 2 of 5