Winchester, KY Homes for Sale

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  /18

  $574,000

  • 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) 209-6934

  110 White Conkwright Rd, Winchester, KY 40391
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  /58

  $488,000

  • 4 Beds
  • 4 Baths
  • 4,448 Sq Ft

  150 Stone Crest Rd, Winchester, KY 40391

  IMMEDIATE OCCUPANCY! WELCOME HOME with Room to spread out in this SPACIOUS Home of over 4000 sq. ft. sitting on 5.5 Acres! Offering 4 Bedrooms, 4 Bathrooms, Living Room, Beautiful Kitchen with appliances and tons of cherry cabinets, Den, utility room and 2 Large Bonus Rooms in the Basement. one could be a bedroom. There is a 3-car Detached Garage, 2-car attached Garage, Large Carport, Huge Patio

  

  Brenda Murphy

  Murphy Realty Group

  (859) 374-8718

  150 Stone Crest Rd, Winchester, KY 40391
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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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  /117

  $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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  /51

  $445,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 2 Baths
  • 3,181 Sq Ft

  17 Hampton Ave, Winchester, KY 40391

  This meticulous house is located within walking distance of many popular Winchester destinations; The Winchester Country Club, The Public Library and the indoor gym and swimming facility at College Park. Now back to the meticulous house. When you enter the front door you will immediately feel the how the owners have taken such great care of this house. The gleaming hardwoods, the large living

  Craig Bridgewater Bridgewater Real Estate

  17 Hampton Ave, Winchester, KY 40391
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  /39

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft

  600 Ferry Rd, Winchester, KY 40391

  Experience abundant wildlife with turkey and deer in your own hunting retreat, or simply enjoy the views from your backyard on this stunning 33-acre property. Conveniently located near the Kentucky River, with a boat ramp nearby, this home offers the perfect blend of nature and accessibility, making it ideal for nature lovers or those who enjoy fishing and hunting.Step inside to the foyer,

  Cathleen Gedeon CENTURY 21 Advantage Realty

  600 Ferry Rd, Winchester, KY 40391
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  /33

  $400,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 3 Baths
  • 2,741 Sq Ft

  113 Shala Mar Rue, Winchester, KY 40391

  Beautifully maintained brick ranch on a full basement, offering over 4,000 square feet under roof in a highly desirable location just minutes from Hamburg, I-64, Lexington, and Clark County Regional Hospital. This spacious home features 4 bedrooms, 3 full baths, and stunning hardwood floors. Two impressive floor-to-ceiling fireplaces add charm on both levels. The kitchen includes new stainless

  Rebakah Goodpaster Keller Williams Legacy Group

  113 Shala Mar Rue, Winchester, KY 40391
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  /114

  $649,000

  • 5 Beds
  • 4.5 Baths
  • 5,524 Sq Ft

  315 The Woods Ln, Winchester, KY 40391

  Beautiful 1.5-story brick home on a cul-de-sac with in-ground pool and walkout basement! The main level features hardwood floors, office, formal dining room, and spacious family room with gas fireplace. The kitchen includes stainless appliances (all convey), double oven, gas cooktop, island, eat-in area, and large pantry. Oversized mudroom/laundry adds great storage. First-floor primary suite

  Terri McGraw FC Tucker Bluegrass

  315 The Woods Ln, Winchester, KY 40391
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  /3

  $380,000

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

  270 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 on unfinished walkout basement.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a

  Rex Hall United Real Estate Bluegrass

  270 Evergreen Dr, Winchester, KY 40391
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  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  265 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, walkout unfinished basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  265 Evergreen Dr, Winchester, KY 40391
• 

  

  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,885 Sq Ft

  250 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391
• 

  

  /3

  $380,000

  • 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
• 

  

  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,935 Sq Ft

  220 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  220 Evergreen Dr, Winchester, KY 40391
• 

  

  /3

  $380,000

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

  200 Evergreen Dr, Winchester, KY 40391

  Introducing the Run For The Roses - 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 bathroom. The kitchen

  Rex Hall United Real Estate Bluegrass

  200 Evergreen Dr, Winchester, KY 40391
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  /52

  $555,000

  • 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 your

  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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  /48

  $570,000

  • 5 Beds
  • 3 Baths
  • 3,489 Sq Ft

  594 Earlymeade Dr, Winchester, KY 40391

  This stunning 5BR,3BA brick home blends classic charm with modern comfort, all situated in a highly desirable neighborhood. The exterior features clean lime wash brick with contrasting painted trim and a crisp new black roof, new black 6mm gutters, exuding timeless curb appeal. A wide front porch with elegant columns welcomes you into the home, perfect for relaxing or greeting guest.Inside you

  Alyssa M Boley Coldwell Banker McMahan

  594 Earlymeade Dr, Winchester, KY 40391
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  /62

  $379,900

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

  309 Gallahadion Ct, Winchester, KY 40391

  This beautiful 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. Don't miss the primary bedrooms with walk in closet, double sinks and tile shower in the bathroom. The two car garage is located on

  Josh Wood Freedom Realty & Property Mgt

  309 Gallahadion Ct, Winchester, KY 40391
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  /17

  $450,000

  • 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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  /4

  $369,900

  • 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
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  /46

  $455,000

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

  42 Mockingbird Valley Rd, Winchester, KY 40391

  Beautiful Hampton Manor home offers easy access to all Winchester has to offer! Located right off Boone Ave, this home boasts tons of updates including an Entertaiment Kitchen with granite countertops, Bosch appliances and great storage, refinished hardwoods, new windows, Updated bathroom showers, a pool, covered front porch back porch and separate covered area outback to enjoy all summer long. 3

  Whitney Ensor Ensor Real Estate LLC

  42 Mockingbird Valley Rd, Winchester, KY 40391
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  /2

  $399,000

  • 4 Beds
  • 2.5 Baths
  • 2,189 Sq Ft

  4541 Colby Rd, Winchester, KY 40391

  ''Discover the perfect blend of comfort and country charm in this 4-bedroom, 2.5-bath home! Nestled in a serene setting, this property boasts a beautifully front and back yard, offering ample space for relaxation and outdoor enjoyment. Whether you're savoring the peaceful surroundings or entertaining guests, this home is a true gem. Don't miss your chance—More pictures to come,Not available for

  Darrell Tackett Dream Maker Realty, LLC

  4541 Colby Rd, Winchester, KY 40391
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  /34

  $332,900

  • 4 Beds
  • 2.5 Baths
  • 2,162 Sq Ft

  366 Hanover Dr, Winchester, KY 40391

  Gorgeous 2 Story Home, Offering 4 Bedrooms, 3 Baths, Oversized Bonus Room, First Floor Primary, With Large Walk-In Closet, And En-Suite, Separate Dining, Attached Garage, First Floor Laundry & Mud Room.... You Need To Schedule! Centrally Located To All Main Shopping, Hospitals And Schools, This Home Has Everything! Choose From Two Covered Porches For Morning Coffee Or An Evening Tea. Or Spend

  Melissa Thompson Keller Williams Legacy Group

  366 Hanover Dr, Winchester, KY 40391
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  /31

  $179,900

  • 3 Beds
  • 1 Bath
  • 1,332 Sq Ft

  120 E Lexington Ave, Winchester, KY 40391

  Looking for an affordable home? Look no further than this recently updated 3 bedroom 1 bath with possible 4th bedroom or bonus room. New flooring, appliances, fixtures and new hvac. Replacement windows before current owner. Great starter home located convenient to downtown area and shopping.

  Chris Johnson Plum Tree Realty

  120 E Lexington 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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  /58

  $274,900

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  137 Sturbridge Ln, Winchester, KY 40391

  This lovely story and a half home is conveniently located close to Bypass road with easy access to everything Winchester has to offer. The main floor offers a comfortable living area that connects to the spacious eat-in kitchen, a convenient half bathroom, and the laundry room. Take a step out the back patio door to experience the generous, shaded, privacy fenced back yard perfect for kids or

  Josh Wood Freedom Realty & Property Mgt

  137 Sturbridge Ln, Winchester, KY 40391
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  /21

  $289,000

  • 3 Beds
  • 2.5 Baths
  • 1,696 Sq Ft

  219 Bartram Ct, Winchester, KY 40391

  This charming residence features a desirable first-floor primary bedroom and a spacious kitchen complete with a breakfast bar—perfect for everyday living and entertaining. Enjoy peace of mind with a brand-new roof and updated systems throughout. Located in a sought-after neighborhood close to everything you need. Don't miss the opportunity to make this home yours—schedule your showing today!

  Nora Williams Keller Williams Commonwealth

  219 Bartram Ct, Winchester, KY 40391
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  /55

  $174,900

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

  20 Heather Ln, Winchester, KY 40391

  This charming 2-bedroom, 1.5-bath brick townhome offers a comfortable living space in a prime location. Inside, you'll find all-new LVP flooring, fresh carpet, and a fresh coat of paint throughout. The spacious living room flows into a well-sized kitchen featuring brand-new countertops and ample counter space—perfect for everyday cooking and entertaining.Appliances including the washer,

  Josh Wood Freedom Realty & Property Mgt

  20 Heather Ln, Winchester, KY 40391
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  /14

  $265,000

  • Land
  • 52 Acres
  • $5,048 per Acre

  3020 Dry Fork Creek Rd, Winchester, KY 40391

  Unmatched Opportunity - 52.5 Acres Just 30 Minutes from Lexington!Escape to your own private retreat with this expansive 52.5-acre property, ideally located just 30 minutes from Lexington and only 15 minutes from downtown Winchester. Whether you're dreaming of building your custom home surrounded by nature or creating the perfect hunting getaway, this property offers endless

  Danielle Hatton The Brokerage

  3020 Dry Fork Creek Rd, Winchester, KY 40391
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  /39

  $258,000

  • 3 Beds
  • 2 Baths
  • 1,235 Sq Ft

  172 Ryans Mill Rd, Winchester, KY 40391

  This nicely maintained 3-bedroom, 2-bath ranch offers the perfect blend of comfort and convenience. Enjoy abundant natural light throughout the open floor plan, creating a bright and inviting atmosphere. The spacious kitchen and living areas are perfect for both daily living and entertaining. Step outside to a generous, fully fenced backyard, ideal for pets, play, or outdoor gatherings. Located

  Elizabeth Herrington Bluegrass Sotheby's International Realty

  172 Ryans Mill Rd, Winchester, KY 40391
• 

  

  /22

  $219,900

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  517 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 AMI 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

  517 Acadia Way, Winchester, KY 40391
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  /28

  $49,500

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft

  706 Pear Ct, Winchester, KY 40391

  Cozy and full of charm! This 3-bedroom, 2-bath manufactured home offers an inviting space with plenty of natural light, a roomy kitchen, and comfortable bedrooms. Located on leased land in a peaceful community, this home is a hidden gem for those looking to own without the high price tag. Current lot rent is $420/ month. Includes a shed for extra storage. Call your agent to schedule an

  Deangela Robinson Keller Williams Commonwealth

  706 Pear Ct, Winchester, KY 40391
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  /44

  $834,000

  • 5 Beds
  • 3.5 Baths
  • 3,384 Sq Ft

  150 Jones Nursery Rd, Winchester, KY 40391

  Experience the perfect blend of modern comfort and country charm in this stunning 4-bedroom, 3.5-bathroom Craftsman-style home, built in 2018. Nestled on 2.58 acres of scenic countryside, this property offers the serenity of rural living with convenient access to Lexington.Designed for both style and functionality, the spacious interior features a chef's kitchen with custom countertops, a

  Joshua Davis The Agency

  150 Jones Nursery Rd, Winchester, KY 40391
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  /33

  $350,000

  • 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
• 

  

  /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
• 

  

  /23

  $229,000

  • 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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  /40

  $342,000

  • 3 Beds
  • 2 Baths
  • 1,988 Sq Ft

  13544 Irvine Rd, Winchester, KY 40391

  Ready for beautiful sunrises and bird watching? This home offers that and more! Almost 4 acres with a tree grove, surrounds this brick ranch on full basement. The possibility to finish the basement and downstairs bath, could add to your sq. ft. Room for a garden/chickens, if that is your thing. Come welcome the peacefulness of country living!

  Susan Baldwin Rector Hayden Realtors

  13544 Irvine Rd, Winchester, KY 40391
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  /34

  $299,900

  • 4 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  410 E Broadway St, Winchester, KY 40391

  Completely remodeled 4 bedroom, 2.5 bath home located in the heart of downtown Winchester. This home features a spacious open floor plan, a first-floor primary suite and a lot of charm. The kitchen, living, and dining areas flow together seamlessly, offering ample space and natural light. Upstairs includes three additional bedrooms and a full bath. Outside, enjoy a large backyard with pool and

  Erin Hurst Bluegrass Properties Group

  410 E Broadway St, Winchester, KY 40391
• 

  

  /3

  $345,000

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

  225 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

  225 Evergreen Dr, Winchester, KY 40391

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