Studio to 5 Bedroom Homes for Sale in Winchester, KY

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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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  /58

  $457,900

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

  42 Mockingbird Valley Rd, Winchester, KY 40391

  The term 'Move In Ready' really and truly applies here at 42 Mockingbird Valley Road! Versatility, Family Friendly, Well Constructed and Maintained, Mature Landscaping and Quiet Location are among the many attributes you'll find. This beautiful one level home on a full basement is ready for your personal touches.Sparking hardwood floors throughout will highlight and set off your furniture

  Markus Cross McCallie Real Estate

  42 Mockingbird Valley Rd, Winchester, KY 40391
• 

  

  

  /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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  /3

  $430,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,855 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

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391
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  /79

  $435,000

  • 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
• 

  

  /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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  /24

  $188,900

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft

  27 Ashland Ave, Winchester, KY 40391

  Motivated Seller! Move right in and enjoy this well-maintained 3-bed, 2-bath ranch in the heart of Massie Addition! Thoughtfully updated with a recent roof on both the home and garage, a brand-new hot water heater (2025), and a modern, fresh interior paint palette, this home is ready for you. A home warranty covering all major systems and appliances is included for added peace of mind. This

  Robin Mobley-Mosher Marshall Lane Real Estate - Lexington

  27 Ashland Ave, Winchester, KY 40391
• 

  

  /23

  $354,900

  • 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

  $225,000

  • 4 Beds
  • 1 Bath
  • 1,743 Sq Ft

  218 E Washington St, Winchester, KY 40391

  Located towards the heart of downtown Winchester, walkable distance to the local shops and restaurants ! 4 bedrooms but with a big bonus room which you can easily turn into a 5th bedroom or a office. This house has a fenced in back yard which is shaded and is a very nice size as well, along with a detached garage, and a longer driveway. Updates have been made to the residence over the past few

  Fernando Andrade Rector Hayden Realtors

  218 E Washington St, 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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  /85

  $609,900

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

  180 Casa Landa Way, Winchester, KY 40391

  Back on the market at no fault of the property or sellers!! 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

  Janna Smith United Real Estate Bluegrass

  180 Casa Landa Way, Winchester, KY 40391
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  /30

  $210,500

  • 3 Beds
  • 1 Bath
  • 1,354 Sq Ft

  40 Garner St, Winchester, KY 40391

  Check out this lovely all brick, beautifully renovated 3-bedroom,1bath home located in Winchester perfectly blending timeless charm with modern updates. This move-in ready home features a new roof, updated electrical and plumbing, an upgraded kitchen, new flooring, a fully renovated bathroom, fresh paint throughout, and all new appliances. Situated on a spacious corner lot, the property offers

  Nicole Seals Guide Realty, Inc.

  40 Garner St, 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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  /28

  $309,900

  • 3 Beds
  • 3.5 Baths
  • 2,526 Sq Ft

  24 N Burns Ave, Winchester, KY 40391

  Historic charm with all the modern amenities! An inviting front porch and entry lead to a welcoming space warmed by refinished original hardwood floors and a new electric fireplace. Other updates include a brand-new kitchen with granite countertops and new appliances, new lighting fixtures, tile in the foyer and bathrooms, new roof, new plumbing, new electrical, new HVAC, new windows, new spray

  Sarah Hess Keller Williams Commonwealth

  24 N Burns Ave, Winchester, KY 40391
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  /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
• 

  

  /65

  $489,000

  • 3 Beds
  • 2 Baths
  • 2,053 Sq Ft

  670 Lillies Ferry Rd, Winchester, KY 40391

  *MOTIVATED SELLERS* Escape to this serene and private 12+ acre property, boasting a 3BR/2BA home sitting on a partially finished walkout basement providing a versatile space for relaxation, recreation, or additional living quarters. This charming home has lots of recent upgrades, including a brand new HVAC system and energy-efficient windows, ensuring a comfortable and sustainable living

  Jennifer Helton EXP Realty, LLC

  670 Lillies Ferry Rd, Winchester, KY 40391
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  /29

  $268,000

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft

  410 Wellington Way, Winchester, KY 40391

  Discover 410 Wellington Way, a beautifully updated property in a convenient Winchester location! This fully updated, move-in-ready home delivers style, comfort, and convenience from the moment you walk in. Enjoy a bright eat-in kitchen equipped with brand-new, warrantied appliances, plus modern finishes throughout—including all-new paint, new flooring, new light fixtures, new doors, updated

  Monica Marcum Century 21 Pinnacle

  410 Wellington Way, Winchester, KY 40391
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  /37

  $1,595,000

  • 37 Beds
  • 19.5 Baths
  • 26,124 Sq Ft

  2 N Main St, Winchester, KY 40391

  Major CAPEX in 2022 & 2024 — Facade transformation, fully restored and renovated.Current grossing $168,000 annual rent, with $4,000/month upside — beats the 1% rule!The Kerr Building, the largest downtown historical landmark, features structural repairs, new roofing, brick tuck-pointing, secure key-fob entrances, central HVAC, modern kitchens, updated baths, and new flooring. 18 LIHTC

  Blanca Cheung Tsubaki Group, LLC

  2 N Main St, Winchester, KY 40391
• 

  /2

  $345,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  215 Evergreen Dr, Winchester, KY 40391

  Welcome to Triple Crown - a stunning proposed construction home nestled in the beautiful Locust Hill Acres community. Thoughtfully designed with an open-concept layout, this home offers 3 comfortable bedrooms, 2 full bathrooms, and versatile living spaces perfect for today's lifestyle.The expansive primary suite serves as a private sanctuary, complete with a spacious walk-in closet and a

  Rex Hall United Real Estate Bluegrass

  215 Evergreen Dr, Winchester, KY 40391
• 

  

  /3

  $430,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,855 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

  Rex Hall United Real Estate Bluegrass

  220 Evergreen Dr, Winchester, KY 40391
• 

  

  /4

  $625,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,405 Sq Ft

  424 Alexis Way, Winchester, KY 40391

  Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard Cove neighborhood. This exquisite floor plan features a side-turned garage and captivating curb appeal with double front entry doors. Inside, you'll find a thoughtfully designed split-bedroom layout with a spacious primary suite that includes a luxurious ensuite with a walk-in closet, double vanity, tile

  Shane Underwood Keller Williams Commonwealth

  424 Alexis Way, Winchester, KY 40391
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  /58

  $525,000

  • 2 Beds
  • 1.5 Baths
  • 5,054 Sq Ft

  808 Bypass Rd, Winchester, KY 40391

  Unique Mixed-Use Opportunity! This versatile property offers prime potential for a restaurant, café, or retail space in a high-visibility location. The commercial space is turn key for a culinary venture or boutique business. Attached is a separate rental unit with private entrance, offering additional income or an ideal live/work setup. Additional space available for potential 2nd Apartment.

  Diana C Brooker Lifstyl Real Estate

  808 Bypass Rd, Winchester, KY 40391
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  /13

  $252,500

  • 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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  /42

  $349,900

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

  3622 Stamper Dr, Winchester, KY 40391

  This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. Properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming laminate floors and a brick fireplace; the perfect place to

  Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
• 

  

  /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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  /49

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,258 Sq Ft

  233 Cunningham Ln, Winchester, KY 40391

  Mini Farm Alert! This fabulous homestead is located less than 2 miles off the Mountain Parkway making it easily accessible. One level, ranch home that features 3 bedrooms, a luxurious primary ensuite... corner jetter tub, seperate walk in shower with glass door, double bowl raised height vanity and a linen closet complete the bathroom and the bedroom has vaulted ceilings, walk in closet and

  Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  233 Cunningham Ln, Winchester, KY 40391
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  /36

  $345,000

  • 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. Great for downsizing or first time homeowner! 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.

  Garnett Davis Tom Goebel & Company

  208 Citation Ct, Winchester, KY 40391
• 

  

  /3

  $146,000

  • 3 Beds
  • 1 Bath
  • 1,020 Sq Ft

  228 Jackson St, Winchester, KY 40391

  Here's your chance to own a nice investment property. This single family home has a 3 bed 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  228 Jackson St, Winchester, KY 40391
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  /4

  $124,900

  • 4 Beds
  • 2.5 Baths
  • 2,131 Sq Ft

  205 E Washington St, Winchester, KY 40391

  PRICE DROP!!! FLIP This House! Seller Has Added A Large Primary Addition And Front Porch. This 4 Bedroom 2 1/1 Bath Home Is Ready For Your Finishes And Has A Fantastic Floor Plan With Large Loft (Whole Home At Stud Level). Finish This Home It Will Be A Showstopper Better Than New Construction With Large Sq Ft What Many Buyers Are Looking For. Great Opportunity To Make Money Or Live In This

  W Patrick Arvin Keller Williams Commonwealth

  205 E Washington St, Winchester, KY 40391
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  /18

  $115,000

  • 2 Beds
  • 1 Bath
  • 910 Sq Ft

  114 Magnolia St, Winchester, KY 40391

  Great opportunity for investors, flippers, or anyone looking for a project with tons of potential! This 2 bedroom, 1 bath home features a 2 year old roof, giving you a solid head start on future updates. With its convenient location and plenty of possibilities, this property is ready for someone to bring their vision! Selling as is. Cash or conventional financing only.

  Michelle Blackburn RE/MAX Creative, Winchester

  114 Magnolia St, Winchester, KY 40391
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  /32

  $309,000

  • 3 Beds
  • 1.5 Baths
  • 1,356 Sq Ft

  4074 Ironworks Rd, Winchester, KY 40391

  Escape to your own slice of paradise on 4.06 private acres, complete with a peaceful pond perfect for relaxing or fishing. Discover this beautifully updated 3-bedroom, 2-bath home offering 1,356 sq. ft. of inviting, open-concept living. Built in 1973, this charming property features new flooring, a warm, welcoming fireplace, and a modern kitchen with stainless steel appliances. Enjoy added peace

  Ashley Spencer Keller Williams Commonwealth

  4074 Ironworks Rd, Winchester, KY 40391
• 

  

  /3

  $380,000 New Construction

  • 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
• 

  

  /34

  $279,700

  • 3 Beds
  • 2 Baths
  • 1,682 Sq Ft

  404 Wellington Way, Winchester, KY 40391

  This house is located minutes from the Winchester Bypass and within walking distance of the new Clark County Pre-school. The house features 3 bedrooms and 2 full baths. The kitchen is open to a large dining area. The kitchen is supplied with all the appliances. And the house also has a washer and dryer. The large great room is perfect for watching the favorite sports teams and movies with family

  Craig Bridgewater Bridgewater Real Estate

  404 Wellington Way, Winchester, KY 40391
• 

  

  /41

  $318,000

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

  118 Windridge Dr, Winchester, KY 40391

  Start off the new year in a new home! 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

  Michelle Blackburn RE/MAX Creative, Winchester

  118 Windridge Dr, Winchester, KY 40391
• 

  

  /47

  $499,000

  • 5 Beds
  • 3.5 Baths
  • 3,823 Sq Ft

  595 Earlymeade Dr, Winchester, KY 40391

  Entertaining the idea of entertaining family and friends? Looking for space for living the good life in a fun house in a great neighborhood? Then look no further. This house is ready for you to make it your new home. Located in the desirable neighborhood of Earlymeade, this house is minutes from the Winchester Bypass, I- 64 corridor and the Hamburg area of Lexington. Along with 5 bedrooms and 3.5

  Craig Bridgewater Bridgewater Real Estate

  595 Earlymeade Dr, Winchester, KY 40391

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