Winchester, KY Homes for Sale

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  /3

  $70,000

  • Land
  • 2.04 Acres
  • $34,314 per Acre

  150 Spencer Ln, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! This lot totaling 2.041 acres, offer 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 the beauty and tranquility. Don't miss your opportunity to own prime land with unmatched potential!

  Kathryn Cheuvront Coldwell Banker McMahan

  150 Spencer Ln, Winchester, KY 40391
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  /43

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,414 Sq Ft

  430 Fairholme Way, Winchester, KY 40391

  Nestled in the serene landscape of Kentucky, is this stunning 1 1/2 story brick home. It offers the perfect blend of elegance and modern comfort. This inviting home offers a timeless appeal that harmonizes beautifully with the tranquil surroundings. It's located on the outskirts of town, in a quiet neighborhood, making it the perfect retreat from the hustle and bustle of life. It's perfect

  Robyn Bradley Woods Realty Group

  430 Fairholme Way, Winchester, KY 40391
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  /2

  $135,000

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  175 Magnolia St, Winchester, KY 40391

  Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Both units are currently used as investment property. Both homes need extensive repair. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is

  A. Rebecca Woods Woods Realty Group

  175 Magnolia St, Winchester, KY 40391
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  /15

  $187,500

  • Land
  • 7 Acres
  • $25,202 per Acre

  7575 Irvine Rd, Winchester, KY 40391

  Amazing 7.44 acre country building lot / mini farm / homestead with views! Established driveway leads a nice 38' x 50' pole barn that would serve as a nice shop / garage! Partially fenced with gated entrance. Perfect spot to potentially build a pond. Water meter base and electricity pole already in place.

  Jason Townsend Kentucky Residential Real Estate, LLC

  7575 Irvine Rd, Winchester, KY 40391
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  /44

  $325,000

  • 3 Beds
  • 2 Baths
  • 2,459 Sq Ft

  43 Skylark Dr, Winchester, KY 40391

  Discover this inviting 3-bedroom, 2-bath ranch-style home with a 2 car garage on a half acre lot! This well-maintained home offers comfort, convenience, and plenty of flexible space both inside and out. There are multiple rooms that can be used as a main living room, family room, home office, or kids playroom. Additional features include vinyl plank floors, a newer roof, a cozy gas fireplace, and

  Chad Bowman The Brokerage

  43 Skylark Dr, Winchester, KY 40391
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  /14

  $285,000

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

  10 Upper St, Winchester, KY 40391

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

  E. Clark Toleman Real Estate Appraisal Services

  10 Upper St, Winchester, KY 40391
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  /39

  $549,400

  • 5 Beds
  • 3.5 Baths
  • 3,478 Sq Ft

  154 Hawthorne Dr, Winchester, KY 40391

  This outstanding 5 bedroom, 3.5 bathroom craftsman-style home boasts custom upgrades and modern finishes throughout. Built in 2020, no detail was spared during the construction of this beautiful residence, nestled on a dead end street in the heart of Earlymeade. The main level boasts an open floor plan with 9' ceilings, spacious living room with gas fireplace & built-ins, gourmet kitchen with

  Jarran Thomas The Agency

  154 Hawthorne Dr, Winchester, KY 40391
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  /3

  $93,500

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  1860 Ford Rd, Winchester, KY 40391

  AS IS property!This unique property, located near the beautiful Kentucky River, offers incredible potential for those seeking a rewarding project. The 825 square foot mobile home is ready for renovation, providing an excellent opportunity for flipping or customization to suit your vision. Alongside the home, you'll find a massive 1792 square foot detached garage, perfect for storage, a

  Omar Shalash Tru Life Real Estate

  1860 Ford Rd, Winchester, KY 40391
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  /13

  $149,400

  • Land
  • 2.30 Acres
  • $64,957 per Acre

  110 Knox Ct, Winchester, KY 40391

  The largest and most desirable lot in The Reserve is now available! Nestled in a cul-de-sac, this 2.3 acre tract offers exceptional views of Bluegrass farmland. Build your custom dream home and watch the sun set over the pond, right from your porch. Located in one of Winchester's newest luxury subdivisions, featuring carefully crafted guidelines to preserve the community's character. All of this

  Jarran Thomas The Agency

  110 Knox Ct, Winchester, KY 40391
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  /10

  $215,000

  211 Ashton Oak Way, Winchester, KY 40391

  Here is the Blank Canvas to build your Dream Home in the Plantation Subdivision. This two story brick building, formerly the Sales Office for the Subdivision, has been gutted to offer the unique opportunity to build a 3118 Sq Ft Home consisting of Four Bedrooms, Two and Half Baths, an open concept on the main level with the addition of a two car garage. Contact listing agent to discuss current

  Melia Hord Keller Williams Bluegrass Realty

  211 Ashton Oak Way, Winchester, KY 40391
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  /71

  $950,000

  • 4 Beds
  • 2.5 Baths
  • 5,290 Sq Ft

  186 Chardonnay Ct, Winchester, KY 40391

  Step into a world of both comfort and convenience with this beautiful 3/4 bedroom, two and one half bath, perfectly designed for relaxation and entertainment. Key features of this property include outdoor spaces to enjoy morning coffee or quiet evening chats. The cozy back porch extends your living space, ideal for dining and enjoying the tranquil surroundings, The beautifully designed patio

  Brenda Sipes Bridgewater Real Estate

  186 Chardonnay Ct, Winchester, KY 40391
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  $699,900

  • 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,

  Holly Goeing The Agency

  600 Boone Ave, Winchester, KY 40391
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  /17

  $459,000

  • 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

  $109,000

  • Land
  • 4.02 Acres
  • $27,114 per Acre

  2058 Athens Boonesboro Rd, Winchester, KY 40391

  Prime building lot - 4.15 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2058 and 2010 lots approved shared entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first

  Megan McCoy Keller Williams Legacy Group

  2058 Athens Boonesboro Rd, Winchester, KY 40391
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  /3

  $109,000

  • Land
  • 4.02 Acres
  • $27,114 per Acre

  2010 Athens Boonesboro Rd, Winchester, KY 40391

  Prime building lot - 4 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2010 and 2058 approved shared entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first choice on

  Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
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  /51

  $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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  /65

  $279,000

  • 4 Beds
  • 1.5 Baths
  • 1,873 Sq Ft

  151 Hilltop Dr, Winchester, KY 40391

  Lovely ranch on a basement home in a small rural neighborhood. This location is the perfect blend of rural living but very convenient to everything! Less than 1 mile from the eastern bypass that provides fast access to I-64, downtown Winchester, parks, and shopping. Large half acre lot with fenced in backyard and a chicken coop! Large deck on the back for entertaining or just relaxing while

  Jason Townsend Kentucky Residential Real Estate, LLC

  151 Hilltop Dr, Winchester, KY 40391
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  /13

  $89,900

  • 2 Beds
  • 1 Bath
  • 1,113 Sq Ft

  2431 Pine Ridge Rd, Winchester, KY 40391

  Looking for a quite place in the country that will give you enough room for a great garden, a few chickens and a huge helping of peace and quiet?? This little gem may be for you. A 1920 built wood home tucked away in the hills of Clark County. Call today for your private showing.

  A. Rebecca Woods Woods Realty Group

  2431 Pine Ridge Rd, Winchester, KY 40391
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  $1,185,000

  • 5 Beds
  • 4 Baths
  • 4,058 Sq Ft

  2447 Clintonville Rd, Winchester, KY 40391

  What a great opportunity to own 3 acres just 15 minutes from Man O War and 20 minutes to the Hamburg Shopping Area. The property features a beautiful brick home built by Michael Childers to use as his main residence. It has been beautifully updated with gleaming, newly refinished hardwood floors, tall ceilings and lavish woodwork. The two story Entry is flanked by a formal Dining Room with a

  Suzanne Elliott Berkshire Hathaway de Movellan Properties

  2447 Clintonville Rd, Winchester, KY 40391
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  /15

  $53,000

  • Land
  • 6 Acres
  • $9,481 per Acre

  199 Midway Rd, Winchester, KY 40391

  Introducing this 5.59 acre property in Central Kentucky! With city water and electric available at the road, this land offers a seamless transition for your dream home or investment project. Located just 15 minutes from Winchester, 30 minutes from Hamburg, and 30 minutes from Mt. Sterling. You will enjoy easy access to city amenities while relishing the peace of rural living. Don't miss the

  Skyler Lewis Dream Maker Realty, LLC

  199 Midway Rd, Winchester, KY 40391
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  /32

  $183,000

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

  517 Hidden Hills Way, Winchester, KY 40391

  Enjoy the convenience of a prime location with this property. Mature trees provide shade and privacy, while the screened sunroom offers a relaxing space. You'll also appreciate the proximity to restaurants, shopping, the Bypass, and the Interstate, making commuting and errands a breeze. Inside this beautifully updated home you will find 3 bedrooms, 2 full bathrooms, fresh paint, new

  Brenda Sipes Bridgewater Real Estate

  517 Hidden Hills Way, Winchester, KY 40391
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  /33

  $252,000

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  14 Calloway St, Winchester, KY 40391

  Beautiful and completely remodeled! Welcome to this stunning home. As you pull up, you will notice a brand new driveway and the inviting front entry.Upon entering, you will love the open floor plan and the brand new luxury vinyl plank flooring. The bright inviting kitchen is just waiting for you to cook and entertain. With brand new cabinets, quartz countertops, stainless steel appliances and

  Libby VanMeter Marshall Lane Real Estate - Lexington

  14 Calloway St, Winchester, KY 40391
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  /14

  $232,500

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  313 Vanover Way, Winchester, KY 40391

  Charming 3-bedroom, 2-bath brick home with both an attached and detached 1-car garage for added storage and convenience! This 1,064 sq ft home features a welcoming front entry with a ramp for easy access. Inside, enjoy a functional layout with comfortable living spaces. Outside, the detached garage offers extra workspace or storage. Conveniently located with easy access to I-64 and just minutes

  Bob Sophiea eXp Realty, LLC

  313 Vanover Way, Winchester, KY 40391
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  /26

  $239,900

  • 3 Beds
  • 2 Baths
  • 1,878 Sq Ft

  134 Boone Ave, Winchester, KY 40391

  Step into this inviting home at 134 Boone Avenue, where timeless charm and thoughtful details create a warm and welcoming atmosphere. The classic front porch sets the tone, while inside, vintage wood floors, beautiful foyer, and large windows flood each room with natural light. The spacious living room has a cozy, intimate feel, perfect for family gatherings or quiet nights in. A delightful

  steven lindsey CENTURY 21 Commonwealth R E

  134 Boone Ave, Winchester, KY 40391
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  /4

  $139,900

  • Land
  • 6 Acres
  • $24,674 per Acre

  1445 Gay Evans Rd, Winchester, KY 40391

  Welcome to The Retreat at Juett Farms! Come build your dream home on some of the best land that Clark County has to offer. This peaceful setting with unparalleled views of the countryside, is sure to impress. Imagine sitting on your front porch taking in the most amazing sunsets! This beautiful parcel has over 5 acres of unrestricted land. Schedule your showing today!

  Holly Goeing The Agency

  1445 Gay Evans Rd, Winchester, KY 40391
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  /4

  $149,900

  • Land
  • 6 Acres
  • $26,768 per Acre

  1541 Gay Evans Rd, Winchester, KY 40391

  Welcome to The Retreat at Juett Farms! Come build your dream home on some of the best land that Clark County has to offer. This peaceful setting with unparalleled views of the countryside, is sure to impress. Imagine sitting on your front porch taking in the most amazing sunsets! This beautiful parcel has over 5 acres of unrestricted land. Schedule your showing today!

  Holly Goeing The Agency

  1541 Gay Evans Rd, Winchester, KY 40391
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  /28

  $799,900

  • Land
  • 13 Acres
  • $60,644 per Acre

  1600 Ironworks Rd, Winchester, KY 40391

  This property has it all! Easy access to Veterans Memorial Bypass, I-64, and downtown Winchester, plus entrances on Ironworks road and clear visibility from the Bypass. This does have sewer and water located on the property. Full of potential possibilities zoned Planned Development and more acreage is available if needed. The property access is a driveway off Ironworks Road across from Center

  Josh Wood Freedom Realty & Property Mgt

  1600 Ironworks Rd, Winchester, KY 40391
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  /22

  $949,900

  • Land
  • 12 Acres
  • $76,729 per Acre

  1203 Irvine Rd, Winchester, KY 40391

  This 12+ acre piece of prime real estate is full of potential! Zoned for business uses, the location is conveniently located with easy access to Veterans Memorial Bypass, I-64, and downtown Winchester. Utilities are already available at this property and there is a small structure included in as-is condition. Give us a call with any further questions.

  Josh Wood Freedom Realty & Property Mgt

  1203 Irvine Rd, Winchester, KY 40391
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  /4

  $140,000

  • Land
  • 3.94 Acres
  • $35,533 per Acre

  12569 Ironworks Rd, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! These two parcels totaling 3.94 acres, offer 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 the beauty and tranquility. Don't miss your opportunity to own prime land with unmatched potential!

  Kathryn Cheuvront Coldwell Banker McMahan

  12569 Ironworks Rd, Winchester, KY 40391
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  /40

  $326,000

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

  1831 Kiddville Rd, Winchester, KY 40391

  Newly renovated! This beautiful three-bedroom two-bath home boasts Acacia wood plank flooring, custom kitchen cabinets with LED lighting, stainless-steel appliances, a vent-free gas fireplace, a primary bedroom located on the first floor with a large walk-in closet and a full master bathroom, equipped with a double walk-in shower and two sinks. The 3/4-acre lot features TWO buildings for all your

  Derrick Simpson CENTURY 21 Advantage Realty

  1831 Kiddville Rd, Winchester, KY 40391
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  /23

  $775,000

  • 4 Beds
  • 3.5 Baths
  • 2,850 Sq Ft

  240 Duclair Dr, Winchester, KY 40391

  Welcome to 'The Reserve' Winchesters newest Luxury subdivision! Located just minutes from the Winchester Bypass and a short drive to Lexington. This stunning home comes with all the Bells and Whistles from the Painted brick to charming 6' 'real hardwood floors and timeless trim throughout this elegant english cottage home. As you walk thru the mahogany front door you will notice the one of kind

  John Wilson Bluegrass Properties Group

  240 Duclair Dr, Winchester, KY 40391
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  /44

  $529,000

  • Land
  • 9 Acres
  • $59,106 per Acre

  2671 Grimes Mill Rd, Winchester, KY 40515

  Don't miss out on this amazing and rare opportunity to purchase the perfect lot for your dream home. Located just minutes from the I-75/Athens exit (Lexington Sporting Club Stadium) and I-75/Man-O-War interchange, and less than 30 minutes from downtown Lexington, this almost 9-acre, ridgetop lot, includes over 3 acres of mature forest along 350 feet of historic Boone Creek. Almost 6 acres of the

  Jason Robinson Ky Real Estate Sales and Fin

  2671 Grimes Mill Rd, Winchester, KY 40515
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  /2

  $195,000

  • Land
  • 8 Acres
  • $23,353 per Acre

  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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  $280,000 Open Thu 3PM - 5PM

  • 3 Beds
  • 2.5 Baths
  • 1,726 Sq Ft

  216 Prescott Ln, Winchester, KY 40391

  Conveniently located near shopping centers, schools and 6 minutes from the hospital. This home opens to a large den area which could easily be used for dining or flex space. The kitchen has plenty of room for entertaining with an island that opens to a spacious living room with fireplace. Plenty of room for parking in the attached garage. Upstairs features a separate laundry room, bedrooms and

  Brittany Lewis National Real Estate

  216 Prescott Ln, Winchester, KY 40391
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  $785,000

  • 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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  /31

  $525,000

  • 5 Beds
  • 3 Baths
  • 3,262 Sq Ft

  10 French Ave, Winchester, KY 40391

  Remember when things were built to last? This home was built in 1906 and recently underwent a complete renovation to bring this 118 year old home into the 21st century. The owners maintained all of the architectural details while adding the modern luxuries of today. Improvements made to the home consist of new dimensional shingle roof, gutters, soffits rebuilt including rebuilding the decorative

  Brian England Keller Williams Bluegrass Realty

  10 French Ave, Winchester, KY 40391
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  /47

  $401,000

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

  520 Bailey Ln, Winchester, KY 40391

  Beautiful large ranch completely remodeled manufactured home on 24 acres with large addition. large bedrooms, family room, dining room, formal living room, 4 Bedroom and 3 baths. 30 foot above ground pool multiple outbuildings, front porch large back patio and just minutes from downtown Winchester. All new Bathrooms, All new Kitchen, All new fixtures, All new flooring. All new paint. House

  Tony Phillips RE/MAX Creative Realty

  520 Bailey Ln, Winchester, KY 40391
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  /3

  $645,000

  • 4 Beds
  • 2.5 Baths
  • 2,526 Sq Ft

  106 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Claiborne Floor Plan by CP Builders. This stunning 4-bedroom, 2.5-bathroom home offers a luxurious and spacious living experience. The first floor features a magnificent primary suite complete with a spacious ensuite bathroom, a walk-in closet, and direct access to the backyard. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and

  Shane Underwood Keller Williams Commonwealth

  106 Bella Shae Way, Winchester, KY 40391
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  /3

  $670,000

  • 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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  /3

  $700,000

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

  415 Alexis Way, Winchester, KY 40391

  Introducing the Merango, a classic all-brick ranch home designed for both comfort and style. With stunning double front doors and a 2-car attached garage, this home offers incredible curb appeal and modern living. The spacious 3-bedroom, 2-bath layout features a split-bedroom design for added privacy, along with a dedicated study perfect for a home office. The open-concept kitchen is ideal for

  Shane Underwood Keller Williams Commonwealth

  415 Alexis Way, Winchester, KY 40391

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