Winchester, KY Homes for Sale

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  /18

  $579,000

  • 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
• 

  

  

  /10

  $135,000

  • Land
  • 4.01 Acres
  • $33,666 per Acre

  1940 Athens Boonesboro Rd, Winchester, KY 40391

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

  

  Laura Sizemore

  Commonwealth Real Estate Professionals

  (859) 374-8725

  1940 Athens Boonesboro Rd, Winchester, KY 40391
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  /57

  $512,000

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

  150 Stone Crest Rd, Winchester, KY 40391

  WELCOME HOME >>>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 around the Inground

  

  Brenda Murphy

  Murphy Realty Group

  (859) 470-3329

  150 Stone Crest Rd, 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
• 

  

  

  /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

  $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
• 

  

  /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
• 

  /2

  $345,000

  • 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

  $395,000

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

  205 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, and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite bath, providing a relaxing

  Rex Hall United Real Estate Bluegrass

  205 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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  /49

  $645,000

  • 6 Beds
  • 3.5 Baths
  • 5,227 Sq Ft

  439 Lynnway Dr, Winchester, KY 40391

  Welcome to 439 Lynnway Drive, where a brand new roof was just installed April 2025. The main floor boasts a primary en-suite, office space, and laundry room, while the second floor offers additional bedrooms and a versatile bonus room. The basement offers private bed/bath, custom bar, home theater, and in-home gym. Step outside and prepare to be enchanted by an outdoor oasis. Outdoor kitchen

  Reagan Rainey Dream Maker Realty, LLC

  439 Lynnway Dr, Winchester, KY 40391
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  /34

  $385,000

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft

  148 Gibson Way, Winchester, KY 40391

  Better Than New Construction!!! This Spacious 4 Bedroom 2 1/2 Bath Home Is Move In Ready And Has A Beautiful Farm View From Your Covered Porch. Features Include A Large Open Living Room And Kitchen With Plenty Of Cabinet Space; Large Island With Faucet; Granite Countertops; Tile Backsplash; Stainless Steel Appliances; Large pantry; Gas Log Fireplace; Gas Heat; Gas Water Heater; Spacious Laundry

  Patrick Arvin Keller Williams Commonwealth

  148 Gibson Way, Winchester, KY 40391
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  /77

  $399,900

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

  101 Dorset Ln, Winchester, KY 40391

  Welcome to your perfect home retreat! This beautifully updated ranch home features a 2-car garage, spacious open layout, and large bedrooms. The backyard is a showstopper — relax under the covered patio or take a dip in the heated in-ground pool, newly installed in 2022 and surrounded by a sleek concrete patio. Inside, enjoy modern upgrades like granite kitchen countertops, resurfaced and painted

  Josh Wood Freedom Realty & Property Mgt

  101 Dorset Ln, Winchester, KY 40391
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  /73

  $339,900

  • 3 Beds
  • 2 Baths
  • 1,805 Sq Ft

  407 Fairholme Way, Winchester, KY 40391

  Looking for a newer home in a beautiful, family friendly neighborhood? Look no further than this lovely, low maintenance home in the desirable Fairholme Estates subdivision. Take a step inside and enjoy the sunlight streaming in through the abundant windows in the great room. Gleaming, easy to clean, laminate wood plank flooring spills into the spacious kitchen area which features an oversized

  Josh Wood Freedom Realty & Property Mgt

  407 Fairholme Way, Winchester, KY 40391
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  /42

  $425,000

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

  485 Mccullough Ln, Winchester, KY 40391

  The Homestead you have been looking for. Farmhouse in the country. This beauty is just 6 miles from the interstate. Spacious 5.72 acres on this mini farm. It is located at the end of McCullough Lane. This three bedroom 2 bath home has 2,120 square feet. There is a beautiful 9 feet deep inground pool. The pool had a new liner and equipment installed 3 years ago. Inside you will find 3 fireplaces

  Dale Hatton Dream Maker Realty, LLC

  485 Mccullough Ln, Winchester, KY 40391
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  /28

  $379,900

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  230 Hibiscus Ln, Winchester, KY 40391

  Beautiful 1-1/2 story home, lovingly maintained inside and out. 10' ceilings in both foyer and living room with crown molding.1st floor offers a master bedroom with full bath, jetted tub, separate shower and walk in closet. 3 spacious bedrooms & full bath upstairs. Privacy fenced backyard, quiet street with country views. Schedule your showing today!

  Anndrea Burchett Coldwell Banker McMahan

  230 Hibiscus Ln, Winchester, KY 40391
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  /62

  $384,700

  • 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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  /37

  $419,900

  • 4 Beds
  • 4.5 Baths
  • 2,800 Sq Ft

  136 College St, Winchester, KY 40391

  Attention To Detail!!! Tastefully Renovated 4 Bedroom 4 1/2 Bath Home On College Street! Each Bedroom Has Its Own Private Bathroom! This Perfect Home Has Not Only Been Completely Renovated But An Addition Added To Modernize The Layout And Give You A First Floor Master Suite. The Uniqueness Of This Home Has Been Captured Through The Wooden Staircase and Wonderful Curb Appeal That Were Saved. If

  Patrick Arvin Keller Williams Commonwealth

  136 College St, Winchester, KY 40391
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  /26

  $349,000

  • 3 Beds
  • 2.5 Baths
  • 2,065 Sq Ft

  118 Sturbridge Ln, Winchester, KY 40391

  Nestled right in the heart of town, lies this charming 2 story home that embodies the essence of rustic glam. This cozy retreat offers a convenient escape from the hustle and bustle of life. The first floor offers ample space to host friends and family gatherings. Upstairs, the bedrooms serve as serene sanctuaries. Each room offers the perfect balance of the rustic charm. The backyard boasts

  A. Rebecca Woods Woods Realty Group

  118 Sturbridge Ln, Winchester, KY 40391
• 

  

  /28

  $354,900

  • 4 Beds
  • 3 Baths
  • 3,149 Sq Ft

  512 Boone Ave, Winchester, KY 40391

  Step into this stunning home that seamlessly blends modern comfort with timeless charm. The spacious living room boasts an open-concept design, complemented by beautiful hardwood floors, an abundance of natural light, and a cozy fireplace. The large kitchen is a chef's dream, featuring ample shelving, stainless steel appliances, and breathtaking views. Step outside to a massive deck overlooking a

  Jordan James Lifstyl Real Estate

  512 Boone Ave, Winchester, KY 40391
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  /50

  $375,000

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft

  356 Boone Ave, Winchester, KY 40391

  Contract with 48 hr kickout - continue to show. Your chance to live in a beautiful, renovated home on historic Boone Avenue. Walk to downtown, the public library or college park. This two-story home has loads of renovations and is ready for you to move right in. This home features 4 bedrooms and a bonus room, currently used as an office. The updated kitchen is a cooks dream! Granite counters

  Nancy Smith Rector Hayden Realtors

  356 Boone Ave, Winchester, KY 40391
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  /33

  $370,000

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

  4074 Ironworks Rd, Winchester, KY 40391

  Welcome to country living! This newly renovated ranch on 4+ scenic acres offers peaceful living just 10 minutes from town. Inside, the open floor plan seamlessly connects the kitchen, dining, and living areas. The kitchen features granite countertops, new stainless steel appliances, a central island with bar seating, while the living room boasts a cozy fireplace. Durable LVP and tile flooring run

  Michelle Blackburn RE/MAX Creative, Winchester

  4074 Ironworks Rd, Winchester, KY 40391
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  /15

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  210 Jett Dr, Winchester, KY 40391

  Don't miss out on this wonderful ranch floor plan, New Construction, 3 bedrooms, 2 baths, covered porch, great location, Call today.Size of home may vary from plan, spec home,all specifics have already been ordered. This information will follow within a few weeks and posted on line.

  Mila Ensor Ensor Real Estate LLC

  210 Jett Dr, Winchester, KY 40391
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  /92

  $374,900

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft

  31 Mockingbird Valley Rd, Winchester, KY 40391

  This stately, split-level brick home is situated in the beautiful and desirable Hampton Manor subdivision, right in the heart of Winchester. On the main level, gleaming hardwood floors extend throughout, including the newly renovated kitchen with new granite countertops, new cabinets, all new appliances, new faucet and a large island providing plenty of space to prepare family meals. Three

  Josh Wood Freedom Realty & Property Mgt

  31 Mockingbird Valley Rd, Winchester, KY 40391
• 

  

  /3

  $369,900 New Construction

  • 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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  /36

  $829,900

  • 4 Beds
  • 3 Baths
  • 12,900 Sq Ft

  8129 Wades Mill Rd, Winchester, KY 40391

  This is what BARDOMINIUM Dreams are made of!!!! Welcome to your barndo retreat — an expansive 92' x 120' steel-framed structure situated on 4.27 partially fenced acres with breathtaking pond views and unmatched amenities for both living and working.This massive structure boasts an open-concept interior layout with endless potential! Ideal for combining luxury living with functional workspace.

  Holly Goeing The Agency

  8129 Wades Mill Rd, Winchester, KY 40391
• 

  

  /31

  $229,900

  • 3 Beds
  • 1.5 Baths
  • 1,404 Sq Ft

  619 Laura Dr, Winchester, KY 40391

  This beautiful 3-bedroom ranch is ready for you to make it your own. The home boasts 1400 SQ FT and has a wonderful floor plan. Step inside and check out the living room, which has great natural light and lots of space to relax or enjoy company. Home also has a bonus room next to the living room that adds a ton of space for living, work, or play. The formal dining area allows for easy mealtimes

  Kevin Bradley KB Realty Group

  619 Laura Dr, Winchester, KY 40391
• 

  

  /26

  $244,700

  • 3 Beds
  • 2.5 Baths
  • 2,017 Sq Ft

  129 Bay Hill Dr, Winchester, KY 40391

  Located in an established neighborhood this low maintenance spacious townhome with over 2000 square foot has curb appeal and backs to a greenspace with a large backyard and rear facing garage. The home has been well maintained and updated with a new roof and new flooring. The kitchen and family room are nice sized for all your gatherings. For an added convenience the lower level offers a bonus

  Tonya Skeens RE/MAX Elite Lexington

  129 Bay Hill Dr, Winchester, KY 40391
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  /33

  $184,900

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  307 Blair Ave, Winchester, KY 40391

  This charming 3-bedroom, 1-bath ranch offers fresh updates throughout, including brand new flooring and interior paint. The inviting side porch features a ramp for easy accessibility and leads to a spacious patio—perfect for relaxing or entertaining. A detached two-car garage adds great storage and functionality. Located just minutes from downtown Winchester and I-64, this move-in-ready home

  Brooke Otis-Mull Ro&Co Real Estate

  307 Blair Ave, Winchester, KY 40391
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  /20

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft

  800 Country Club Ct, Winchester, KY 40391

  Great Investment Property. This cozy Winchester duplex is in a prime location. Just minutes from the Bypass and downtown. Two bedrooms with 2 full baths. The location is close to several retail stores, restaurants, and golf courses. Property is being sold together and will not separate.

  Dale Hatton Dream Maker Realty, LLC

  800 Country Club Ct, Winchester, KY 40391
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  /41

  $275,000

  • 3 Beds
  • 2 Baths
  • 2,142 Sq Ft

  363 S Main St, Winchester, KY 40391

  Welcome to 363 South Main Street in the heart of Winchester, Kentucky! This charming 3-bedroom, 2-bath home offers the perfect blend of timeless character and modern convenience. Built in 1940, the home exudes classic appeal with thoughtful updates that meet today's lifestyle. With 2,142 square feet of living space, there's plenty of room for a growing family to spread out and feel right at home.

  Zachary Otis HomeLand Real Estate Inc

  363 S Main St, Winchester, KY 40391
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  /8

  $129,000

  • 2 Beds
  • 1 Bath
  • 637 Sq Ft

  109 Spring St, Winchester, KY 40391

  Investment opportunity in Winchester! This 2-bedroom, 1-bath home at 109 Spring St is currently tenant-occupied and leased at $900/month. Functional layout with a spacious kitchen and separate living area. Conveniently located near downtown, schools, and local amenities. Whether you're expanding your portfolio or looking for a starter investment, this property offers steady rental income from day

  Shari Frasure Keller Williams Commonwealth

  109 Spring St, Winchester, KY 40391
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  /5

  $29,000

  • Land
  • 0.46 Acre
  • $63,043 per Acre

  102 Augusta Dr, Winchester, KY 40391

  This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

  Dale Hatton Dream Maker Realty, LLC

  102 Augusta Dr, Winchester, KY 40391
• 

  

  /5

  $189,900 Open Thu 5PM - 7PM

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  11 Apache Trail, Winchester, KY 40391

  MOTIVATED SELLER! This Is The One You Have Been Waiting For!! This Updated 3 Bedroom 1 Bath Home Has A Large Partially Fenced Backyard With A Nice Deck To Enjoy The Warm Spring Weather! Features Include An Open Kitchen/Living Area; Beautiful Shaker Cabinets; Tile Backsplash; Kitchen Aide Gallery Appliances; Side Access Door To Kitchen From Extended Driveway; Roof Replaced February 2022; New

  Patrick Arvin Keller Williams Commonwealth

  11 Apache Trail, Winchester, KY 40391
• 

  

  /13

  $69,900

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  315 Aspen Ln, Winchester, KY 40391

  Home can stay in the park. This beautiful manufactured home is located in a quiet neighborhood with easy access to all the amenities you need. It has a spacious floor plan with three bedrooms, two bathrooms. The kitchen is equipped with modern appliances and plenty of counter space, making it perfect for cooking and entertaining. The primary suite is a retreat with a spacious walk-in closet and a

  Neely Gray VMF Homes

  315 Aspen Ln, Winchester, KY 40391
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  /24

  $219,000

  • 3 Beds
  • 1 Bath
  • 1,420 Sq Ft

  13365 Ironworks Rd, Winchester, KY 40391

  Charming and fully renovated, this 3-bedroom, 1-bathroom home offers the perfect blend of modern style and cozy comfort. With a fresh white exterior accented in black and a brand-new metal roof, it stands out with timeless curb appeal and lasting durability.Inside, every detail has been thoughtfully updated, from the sleek modern kitchen to the stylish lighting fixtures that brighten the space.

  Joshua Davis The Agency

  13365 Ironworks Rd, Winchester, KY 40391
• 

  

  /34

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  37 7th St, Winchester, KY 40391

  Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

  Andrew Fugitt Coldwell Banker McMahan

  37 7th St, Winchester, KY 40391
• 

  

  /35

  $276,500

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  606 Laura Dr, Winchester, KY 40391

  PRICE REDUCTION! Charming ranch home with full finished basement in Verna Hills. Just minutes from Lexington & Winchester. This spacious ranch home offers 3 bedrooms and 2.5 baths. New vinyl windows throughout (except the front living room). Large kitchen with new appliances is open and offers tons of prep space and a pantry. Downstairs the large finished basement provides endless

  Bradley Morgan The Local Agents

  606 Laura Dr, Winchester, KY 40391

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