Winchester, KY Homes for Sale with Garage

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  /18

  $525,000

  $31K PRICE DROP

  • 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

  110 White Conkwright Rd, Winchester, KY 40391
• Explore Winchester

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  /64

  $419,500

  • 4 Beds
  • 2.5 Baths
  • 1,978 Sq Ft

  107 Hibiscus Ln, Winchester, KY 40391

  Welcome to 107 Hibiscus, where thoughtful updates, quality craftsmanship, and exceptional maintenance come together in this spacious 4-bedroom, 2.5-bath home. Offering a versatile floor plan with generous living spaces, this move-in-ready property has benefited from approximately nearly $70,000 in improvements over the past several years, providing peace of mind and modern finishes throughout.

  

  Christa Joynt

  Keller Williams Commonwealth

  107 Hibiscus Ln, Winchester, KY 40391
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  /84

  $699,999

  $99K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 7,058 Sq Ft

  186 Chardonnay Ct, Winchester, KY 40391

  Fontaine Estates, a great place to call home. This spacious 4 bedroom 3 bath property offers an abundance of storage,, including charming window seats. Enjoy the convenience of an oversized driveway and garage, along with a beautifully designed outdoor setting, feauring a fire pit and a dedicated entertainment space. The thoughtfully planned, custom designed landscaping enhances the home's curb

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  186 Chardonnay Ct, Winchester, KY 40391
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  /64

  $420,000

  • 3 Beds
  • 2 Baths
  • 2,027 Sq Ft

  187 Hawthorne Dr, Winchester, KY 40391

  Welcome to 187 Hawthorne Drive, a beautifully maintained brick home in one of Winchester's most sought-after neighborhoods. Offering convenient one-level living, this 3-bedroom, 2-bath home features an inviting open floor plan that's perfect for everyday living and entertaining. The spacious living room is anchored by a cozy natural gas fireplace with gas logs, creating a warm and welcoming

  

  Christa Joynt

  Keller Williams Commonwealth

  187 Hawthorne Dr, Winchester, KY 40391
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  /89

  $919,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 4,019 Sq Ft

  200 Old Log Lick Rd, Winchester, KY 40391

  Behind a private, gated entrance on 14.38 acres, this 3,481 sq ft all-wood cabin estate is a truly rare find in Central Kentucky. Offering 3 bedrooms, 2 bathrooms, and a flexible bonus room perfect as a 4th bedroom or home office, every inch of this home reflects true craftsmanship — rich wood features throughout, a large sunroom, and a screened-in back porch made for long evenings and unhurried

  

  Brad Smith

  Keller Williams Commonwealth - Gorge

  200 Old Log Lick Rd, Winchester, KY 40391
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  /72

  $775,000

  • 5 Beds
  • 3 Baths
  • 4,437 Sq Ft

  465 Morris Rd, Winchester, KY 40391

  Dreaming of wide-open spaces and country charm? This beautiful 16-acre property in Clark County offers the perfect blend of comfort and functionality. The stately brick home provides generous living space with classic appeal, offering endless potential. With five bedrooms and three full baths, the home accommodates a variety of living arrangements, whether you need space for guests, a home

  

  Brenda Leigh Walters

  United Real Estate Bluegrass

  465 Morris Rd, Winchester, KY 40391
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  /35

  $245,000

  Open Sun 1PM - 3PM

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

  216 Robyn Dr, Winchester, KY 40391

  Meticulously maintained 3-bedroom, 2-bath home on a full basement with wonderful curb appeal! Beautiful landscaping and a welcoming covered front porch invite you into this charming home. Inside, you'll find a warm and inviting main level featuring handsome hardwood flooring, a cozy fireplace, and a spacious living area. The adorable kitchen offers plenty of cabinet and counter space, making meal

  

  Robin Jones

  Keller Williams Legacy Group

  216 Robyn Dr, Winchester, KY 40391
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  /46

  $239,000

  $8K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  30 Virginia Ave, Winchester, KY 40391

  Welcome to a well maintained 3 bedroom 1 full bath home that has been lovingly cared for by only two owners since 1962. Recent updates include new flooring and completed repairs, makiing this property ready for a new owner, while preserving its timeless character. Beautiful hardwood floors add warmth and charm throughout the home. Enjoy relaxing or entertaining on the comfortable spacious patio

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  30 Virginia Ave, Winchester, KY 40391
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  /80

  $339,000

  • 3 Beds
  • 3 Baths
  • 2,068 Sq Ft

  13 Bel Air Dr, Winchester, KY 40391

  Don't let this charming brick ranch fool you—it's what's waiting out back that will absolutely steal the show! Nestled in the heart of Winchester, this 3BR/3BA home offers an incredible backyard oasis that's perfect for entertaining, relaxing, and making memories all summer long. The sparkling in-ground pool is the centerpiece of this private retreat, surrounded by expansive concrete decking and

  

  Robin Jones

  Keller Williams Legacy Group

  13 Bel Air Dr, Winchester, KY 40391
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  /46

  $749,900

  • 3 Beds
  • 2.5 Baths
  • 2,735 Sq Ft

  2180 Big Stoner Rd, Winchester, KY 40391

  Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides

  

  Ashley Barreto

  Indigo & Co

  2180 Big Stoner Rd, Winchester, KY 40391
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  /41

  $343,900

  New Construction

  • 3 - 5 Beds
  • 2 - 4 Baths
  • 1,424 Sq Ft

  Lucy Plan at Boone's Crossing, Winchester, KY 40391

  Experience the Lucy floor plan, a versatile and thoughtfully designed new construction home that gives every member of the family the space they need to live, work, and thrive. Built by one of the most trusted home builders in Central Kentucky, the Lucy is a top choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want flexibility, comfort, and

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824256, Winchester, KY 40391
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  /37

  $378,900

  New Construction

  • 3 - 5 Beds
  • 2.5 - 3.5 Baths
  • 2,098 Sq Ft

  Nancy Plan at Boone's Crossing, Winchester, KY 40391

  Experience the Nancy floor plan, a masterfully designed two-story new construction home that blends smart functionality with open-concept living. Built by one of the most trusted home builders in Central Kentucky, the Nancy is an ideal choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want style, flexibility, and efficient use of space.From the

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824252, Winchester, KY 40391
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  /45

  $429,900

  New Construction

  • 3 - 5 Beds
  • 2.5 - 4.5 Baths
  • 2,722 Sq Ft

  Eleanor Plan at Boone's Crossing, Winchester, KY 40391

  Experience elevated living with the Eleanor floor plan, a thoughtfully designed new construction home available through one of the most trusted home builders in Central Kentucky. Created for today’s buyers seeking flexibility, luxury, and energy efficiency, the Eleanor blends timeless design with modern functionality for families looking for new construction homes in Lexington KY and surrounding

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824255, Winchester, KY 40391
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  /35

  $360,900

  New Construction

  • 3 - 4 Beds
  • 2.5 - 3.5 Baths
  • 1,828 Sq Ft

  Grace Plan at Boone's Crossing, Winchester, KY 40391

  Discover the Grace floor plan, a thoughtfully designed new construction home that blends open-concept living with private, comfortable bedroom spaces. Built by one of the leading home builders in Central Kentucky, the Grace is a perfect fit for buyers searching for new construction homes in Lexington KY and nearby communities who want flexibility, style, and energy efficiency.From the moment you

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824257, Winchester, KY 40391
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  /46

  $347,900

  New Construction

  • 3 - 6 Beds
  • 2 - 4 Baths
  • 1,580 Sq Ft

  Martha Plan at Boone's Crossing, Winchester, KY 40391

  The Martha floor plan is your canvas for creating a home that perfectly fits your lifestyle, offering unmatched flexibility, thoughtful design, and timeless appeal. Built by one of the leading home builders in Central Kentucky, the Martha is an excellent choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space that adapts to how they

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824258, Winchester, KY 40391
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  /28

  $363,900

  New Construction

  • 4 - 5 Beds
  • 2.5 - 3.5 Baths
  • 2,100 Sq Ft

  Elizabeth Plan at Boone's Crossing, Winchester, KY 40391

  Experience the Elizabeth floor plan, a beautifully crafted new construction home designed for families who value open-concept living, thoughtful organization, and flexible bedroom space. Offered by one of the most trusted home builders in Central Kentucky, the Elizabeth is a standout option for buyers searching for new construction homes in Lexington KY and surrounding communities.From the moment

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824250, Winchester, KY 40391
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  /85

  $1,349,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,350 Sq Ft

  1200 Craig Crossing, Winchester, KY 40391

  Discover elevated living on 2.5 acres! This 3,350 sqft custom masterpiece boasts 4 bedrooms, 4.5 bathrooms with an open 2,670 sqft main level. Featuring custom solid oak cabinetry not only in kitchen, but master closets, pantry and utility areas. Custom Showers and tile in each bathroom throughout the home. Gas and electric fireplaces located in great room as well as primary first floor bedroom.

  Michael Hilario The Agency

  1200 Craig Crossing, Winchester, KY 40391
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  /85

  $397,900

  New Construction

  • 3 - 5 Beds
  • 2.5 - 4.5 Baths
  • 2,263 Sq Ft

  Abigail Plan at Boone's Crossing, Winchester, KY 40391

  Step into the award-winning Abigail floor plan, a standout choice for buyers searching for new construction homes in Lexington, KY and Central Kentucky. Designed with today’s lifestyle in mind, this home offers the perfect blend of flexible floor plans, energy efficiency, and modern comfort—everything you expect from a trusted home builder in Lexington, KY.From the moment you arrive, the Abigail

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824251, Winchester, KY 40391
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  /52

  $369,900

  New Construction

  • 3 - 6 Beds
  • 2 Baths
  • 1,770 Sq Ft

  Barbara Plan at Boone's Crossing, Winchester, KY 40391

  Experience the true essence of homecoming with the Barbara floor plan, a beautifully designed new construction home available through one of the most trusted home builders in Central Kentucky. Thoughtfully crafted for modern living, this plan blends timeless exterior charm with a warm, open interior designed for comfort, flexibility, and everyday functionality.Step onto the inviting covered front

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824253, Winchester, KY 40391
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  /47

  $427,000

  • 3 Beds
  • 2.5 Baths
  • 2,289 Sq Ft

  20 Edgewood Dr, Winchester, KY 40391

  Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a

  Libby VanMeter Marshall Lane Real Estate - Lexington

  20 Edgewood Dr, Winchester, KY 40391
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  /25

  $275,000

  • 3 Beds
  • 2.5 Baths
  • 1,787 Sq Ft

  304 Newcastle Ln, Winchester, KY 40391

  This house is located within walking distance of Clark County preschool, Strode Station, and Baker and is within minutes of Winchester Bypass and I-64. This house has 3 bedrooms, 2.5 baths and a bonus room on the 2nd floor for a game room or an office. It has a large open great room with a wood burning fireplace. The current owner has this as an investment property and is now ready to sell to a

  Craig Bridgewater Bridgewater Real Estate

  304 Newcastle Ln, Winchester, KY 40391
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  /59

  $499,900

  • 4 Beds
  • 3 Baths
  • 5,646 Sq Ft

  16 Manor Dr, Winchester, KY 40391

  One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home!

  Zella Rosenthal Tom Goebel & Company

  16 Manor Dr, Winchester, KY 40391
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  /26

  $274,900

  $5K PRICE DROP

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

  136 Sturbridge Ln, Winchester, KY 40391

  ***OPEN HOUSE This Thursday 7-16-26 from 5-7pm*** Good things absolutely do come in affordable packages! This well maintained 3 bed 2.5 bath home on the Lexington side of Winchester has a beautiful back yard with a deck and built-in porch swing. It is privacy fenced and ready for you to enjoy, but not at the expense of access to town! With shopping right around the corner, and access to the

  Sarah MacHarg Kentucky Land and Home

  136 Sturbridge Ln, Winchester, KY 40391
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  /57

  $340,000

  $10K PRICE DROP

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

  443 S Maple St, Winchester, KY 40391

  Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make

  Terra Long Keller Williams Commonwealth

  443 S Maple St, Winchester, KY 40391
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  /92

  $795,000

  • 3 Beds
  • 3 Baths
  • 3,336 Sq Ft

  6356 Van Meter Rd, Winchester, KY 40391

  **Click on the Virtual Tour section to see the video walk through!** Nestled in the peaceful countryside of Winchester, this charming property on Van Meter Road offers the perfect blend of privacy, comfort, access and room to roam. Set on 13.74 beautiful, fenced acres and located within minutes of I-64, I-75 and the Mountain Parkway, this unique property offers easy access to Lexington,

  Josh Wood Freedom Realty & Property Management

  6356 Van Meter Rd, Winchester, KY 40391
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  /24

  $365,900

  New Construction $4K PRICE DROP

  • 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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  /10

  $550,000

  New Construction

  • 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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  /55

  $549,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft

  108 Bella Shae Way, Winchester, KY 40391

  Nearly new French country ranch that has been gently lived in. This classy home has magnificent curb appeal. When you walk through the front door you are welcomed by a tasteful foyer area. Stroll into the wide-open space of the great room with a towering, coffered ceiling and tons of natural light. The gas fireplace adds a nice focal point to the living space. The kitchen space is equipped with

  Vickie Skeens RE/MAX Elite Lexington

  108 Bella Shae Way, Winchester, KY 40391
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  /87

  $2,999,000

  $101K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 3,693 Sq Ft

  3049 Ironworks Rd, Winchester, KY 40391

  Some properties are special simply because of the story behind them. This 150-acre farm with 3,168 ft of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek

  Zova Rothchild Keller Williams Legacy Group

  3049 Ironworks Rd, Winchester, KY 40391
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  /63

  $524,900

  • 3 Beds
  • 2.5 Baths
  • 2,514 Sq Ft

  275 Runnymeade Dr, Winchester, KY 40391

  OK! WOW!!! Location is yes, yes, yes! This house is located in a quiet residential neighborhood and in minutes you can be at the I-64 or I-75 interstate corridors. OK enough about location. This house is pristine! The owners have improved the property with new dimensional style roof shingles in 2025 along with new gutters. They have freshly painted the interior. They have added a new

  Craig Bridgewater Bridgewater Real Estate

  275 Runnymeade Dr, Winchester, KY 40391
• 

  

  /22

  $665,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,643 Sq Ft

  414 Alexis Way, Winchester, KY 40391

  Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added

  Shane Underwood Keller Williams Commonwealth

  414 Alexis Way, Winchester, KY 40391
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  /9

  $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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  /72

  $406,900

  New Construction

  • 3 - 6 Beds
  • 2.5 - 5.5 Baths
  • 2,570 Sq Ft

  Jackie Plan at Boone's Crossing, Winchester, KY 40391

  Unleash your creativity with the Jackie floor plan, a flexible and thoughtfully designed new construction home that empowers you to shape your ideal living space. Built by one of the most trusted home builders in Central Kentucky, the Jackie is a standout choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space, versatility, and modern

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824254, Winchester, KY 40391
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  /36

  $540,000

  $10K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 4,173 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
• 

  

  /23

  $99,900

  • 3 Beds
  • 2 Baths
  • 675 Sq Ft

  2799 Pine Ridge Rd, Winchester, KY 40391

  If your looking for a fixer upper, this is it. House on 2 acres in the country with lots of potential. Laundry is off the kitchen, but floor is soft from a water leak. From the kitchen you will see a guest bath, dining and living area. To the left is a hallway that leads to 2 bedrooms, drywalled just needs to be finished. To the right of the living area is your master bedroom and bath. With some

  Robin Horn Keller Williams Commonwealth

  2799 Pine Ridge Rd, Winchester, KY 40391
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  /17

  $395,000

  $69K PRICE DROP

  • 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
• 

  

  /25

  $235,500

  $4K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  125 Kittison Dr, Winchester, KY 40391

  Charming ranch home featuring 3 bedrooms, 1 full bath with a spacious layout and inviting curb appeal. Enjoy relaxing or entertaining on the covered back patio overlooking the large backyard with plenty of room for pets, play, or gardening. The kitchen offers beautiful granite countertops, ample cabinet space, and all appliances stay for added convenience. A wonderful opportunity for comfortable

  Kathryn Cheuvront Coldwell Banker McMahan

  125 Kittison Dr, Winchester, KY 40391
• 

  

  /30

  $315,000

  • 4 Beds
  • 3 Baths
  • 1,840 Sq Ft

  209 Connie Ln, Winchester, KY 40391

  Get here first, make an offer on this 4 bedroom, 3 bath, 1 1/2 story home, 2 car garage, showroom fresh condition, vaulted ceiling, hardwood floors, tile, carpet, deck, nice back yard, call today to view.

  Mila Ensor Ensor Real Estate, LLC

  209 Connie Ln, Winchester, KY 40391
• 

  

  /86

  $789,000

  • 3 Beds
  • 2 Baths
  • 2,148 Sq Ft

  6500 Mount Sterling Rd, Winchester, KY 40391

  **Drone video and outside pictures available.** Enjoy the space and privacy you've been searching for at 6500 Mount Sterling Rd. Situated on a beautiful rural setting, this property offers the tranquility of country living while remaining conveniently close to Winchester and Lexington. Located less than a minute off exit 101 on I-64. The gorgeous property offers plenty of room for horses,

  Josh Wood Freedom Realty & Property Management

  6500 Mount Sterling Rd, Winchester, KY 40391
• 

  

  /7

  $365,900

  New Construction $4K PRICE DROP

  • 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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