Winchester, KY Homes for Sale

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  $345,000 New Construction

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

  225 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

  Rex Hall United Real Estate Bluegrass

  225 Evergreen Dr, Winchester, KY 40391
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  $72,500

  • 3 Beds
  • 2 Baths
  • 1,128 Sq Ft

  725 Berry Ct, Winchester, KY 40391

  Looking for affordable homeownership in Winchester, KY? This move-in ready 3-bedroom, 2-bath manufactured home offers modern living at an incredible value. Built just 3 years ago and meticulously maintained, this home feels like new from the moment you step inside. Located in the heart of Winchester, you'll enjoy easy access to local restaurants, shopping, grocery stores, parks, and everyday

  Christa Joynt Keller Williams Commonwealth

  725 Berry Ct, Winchester, KY 40391
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  $200,000

  • Land
  • 0.81 Acre
  • $246,914 per Acre

  550 Bullion Blvd, Winchester, KY 40391

  Rarely available Bypass frontage lot for sale! Exciting opportunity to locate alongside a new Chipotle that is soon to be under construction. Retention in place, leaving approximately 1/2-acre developable. Perfect location for a national retailer. Ideally located along the heart of Bypass Road in Winchester, Kentucky between Kroger and Walmart shopping centers. Winchester, Kentucky is the county

  Greg Leveridge Block + Lot Real Estate

  550 Bullion Blvd, Winchester, KY 40391
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  $110,000

  • Land
  • 0.32 Acre
  • $343,750 per Acre

  115 Jacob Ct, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  115 Jacob Ct, Winchester, KY 40391
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  $384,900 New Construction

  • 4 Beds
  • 4.5 Baths

  3600 Crowe Ridge Rd, Winchester, KY 40391

  Newly constructed unfinished multigenerational home located on 4 acres. Separate level living with 2 kitchens, 2 laundry rooms, and an en-suite for every bedroom. The main floor features 21' cathedral ceilings, 8' doors and 15 3'x6' windows creating a spacious home boasting panoramic views. Includes an additional 20'x24' loft space and 2 flex rooms with ANSI standard windows. Secondary living

  Maggie Napier Napier Realtors

  3600 Crowe Ridge Rd, Winchester, KY 40391
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  $635,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,537 Sq Ft

  422 Alexis Way, Winchester, KY 40391

  Introducing the Denver, a gorgeous all-brick ranch home offering 4 bedrooms and 2.5 baths, designed for both luxury and practicality. With its stunning curb appeal, front porch, and beam accents, this home makes a lasting first impression. Inside, the split-bedroom layout offers privacy and space for everyone, with a large primary suite featuring a walk-in closet, soaking tub, separate shower,

  Shane Underwood Keller Williams Commonwealth

  422 Alexis Way, Winchester, KY 40391
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  $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 Legacy Group

  211 Ashton Oak Way, Winchester, KY 40391
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  $110,000

  • Land
  • 0.5 Acre
  • $220,000 per Acre

  260 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  260 Duclair Dr, Winchester, KY 40391
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  $425,000

  • 5 Beds
  • 3.5 Baths
  • 2,564 Sq Ft

  6504 Combs Ferry Rd, Winchester, KY 40391

  Welcome to an extraordinary residence where luxury, craftsmanship, and natural beauty come together. This house has been taken down to the studs, and thoughtfully rebuilt. This two story home with a walk-out basement sits on 8 acres, adjoining the Lower Howard Creek Preserve, offering unmatched privacy and an exceptional standard of living. The owner spared no expense—every detail has been

  Lucy Martin Jenkins United Real Estate Bluegrass

  6504 Combs Ferry Rd, Winchester, KY 40391
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  /27

  $182,000

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft

  6 Monroe Ave, Winchester, KY 40391

  Charming and Updated Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a beautifully maintained 3-bedroom, 2-bath home full of character and modern touches. Step inside to find an inviting family room with an updated shiplap fireplace surround, perfect for cozy evenings. The kitchen is filled with natural light and features granite countertops, making it both stylish and functional.

  Lindsey Bivens Berkshire Hathaway de Movellan Properties

  6 Monroe Ave, Winchester, KY 40391
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  $265,000

  • 2 Beds
  • 2 Baths
  • 1,521 Sq Ft

  174 Hidden Grove Ln, Winchester, KY 40391

  Welcome home to your Kentucky River retreat! This freshly remodeled 2-bedroom, 2-bath charmer offers two inviting covered decks with beautiful river views, a fenced yard for pets or play and even a personal lift for easy access. Inside, enjoy warm, modern updates, with a bright open floor plan. All new flooring, kitchen, baths and much more! Perfect for full-time living or a peaceful getaway just

  Kathryn Cheuvront Coldwell Banker McMahan

  174 Hidden Grove Ln, Winchester, KY 40391
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  $64,900

  • Land
  • 0.52 Acre
  • $124,808 per Acre

  101 Royal Oak Dr, Winchester, KY 40391

  A Unique Opportunity to Build your Dream Home in the Estate Section of Royal Oaks in Clark County. Situated on..52 acres of land and Conveniently located off Exit 96 on I-64, with close proximity to the Industrial Park, Shopping, Dining and downtown Winchester. Call listing agent for additional details and information on the few lots left to build on in this subdivision!

  Melia Hord Keller Williams Legacy Group

  101 Royal Oak Dr, Winchester, KY 40391
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  $10,000

  • Land
  • 0.17 Acre
  • $58,824 per Acre

  117 4th St, Winchester, KY 40391

  Discover the potential of this spacious 0.17-acre residential property nestled in a neighborhood community on clear and level vacant lot located in a Cul-de-sac of Lincoln Park Subdivision. This could be an investment opportunity as well, for ideal savvy investors looking to diversify your portfolio this property would be perfect for building a custom home, holding for future value, or develop

  Anita McDermott Keller Williams Bluegrass Realty

  117 4th St, Winchester, KY 40391
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  $180,000

  • Land
  • 4.45 Acres
  • $40,449 per Acre

  1030 Craig Crossing Rd, Winchester, KY 40391

  Lot # 14 contains 4.450 acres of gently rolling land with small stream perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  1030 Craig Crossing Rd, Winchester, KY 40391
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  $159,900

  • Land
  • 2.66 Acres
  • $60,113 per Acre

  590 Craig Crossing, Winchester, KY 40391

  Don't let this opportunity pass you by again. This prime lot in Thoroughbred Estates is back on the market due to Current owners change of plans. This lot is ready for your new home with a beautiful setting and located close to Winchester and Lexington in a new Luxury Subdivision. Watch the sun set each night from your rear deck or pool. Call today!!!

  Keith Wilson Coldwell Banker McMahan

  590 Craig Crossing, Winchester, KY 40391
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  $78,500

  • Land
  • 0.22 Acre
  • $356,818 per Acre

  Lot 3 Plantations Dr, Winchester, KY 40391

  NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

  Melia Hord Keller Williams Legacy Group

  Lot 3 Plantations Dr, Winchester, KY 40391
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  $349,000

  • 3 Beds
  • 2.5 Baths
  • 2,475 Sq Ft

  212 Woodbine Ct, Winchester, KY 40391

  Step right up - come on in! Its appeal is undeniable, both inside and out! Move-in ready. This well-maintained all-brick ranch on a full basement is full of charm and functionality! — Inside, you'll love having two separate living areas, 1 upstairs and 1 in the basement with a wood burning fireplace in both rooms. Enjoy the cold winter evenings in front of either of the fireplaces with family and

  Kathy Burton Coldwell Banker McMahan

  212 Woodbine Ct, Winchester, KY 40391
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  $240,000

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft

  12 Linden Ave, Winchester, KY 40391

  Cute ranch with easy access to I-64 and downtown Winchester. 3 bedrooms with 2 full baths with 1 car detached garage with fenced in back yard. This property has a interesting feature of a building that's 14 x 40 that has been a rental but can be used as storage or a mother in-law suite.

  Roni Porter RE/MAX Creative Realty

  12 Linden Ave, Winchester, KY 40391
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  $700,000 New Construction

  • 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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  $400,000

  • Land
  • 2.19 Acres
  • $182,648 per Acre

  145 Codella Dr, Winchester, KY 40391

  Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Real Estate

  145 Codella Dr, Winchester, KY 40391
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  $430,000 New Construction

  • 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

  Rex Hall United Real Estate Bluegrass

  265 Evergreen Dr, Winchester, KY 40391
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  $100,000

  • Land
  • 0.68 Acre
  • $147,059 per Acre

  100 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  100 Duclair Dr, Winchester, KY 40391
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  $825,000

  • 2 Beds
  • 1.5 Baths
  • 2,361 Sq Ft

  455 Davis Ln, Winchester, KY 40391

  Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of

  Dale Hatton Dream Maker Realty, LLC

  455 Davis Ln, Winchester, KY 40391
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  $240,000

  • 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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  $645,000 New Construction

  • 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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  $206,000

  • Land
  • 7.77 Acres
  • $26,512 per Acre

  368 Flanagan Station Rd, Winchester, KY 40391

  Build your dream retreat on this beautiful 7.77-acre parcel nestled in a peaceful rural setting just outside Winchester. The gently rolling terrain provides a serene backdrop for your custom home, hobby farm, or equestrian space, offering plenty of room to roam, garden, or simply enjoy the privacy. With easy access from Flanagan Station Road, this property combines a quiet country feel with

  Shari Frasure Keller Williams Commonwealth

  368 Flanagan Station Rd, Winchester, KY 40391
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  $388,000

  • 5 Beds
  • 3 Baths
  • 2,762 Sq Ft

  101 E Lexington Ave, Winchester, KY 40391

  Here's your chance to own a nice investment property. This triplex has a 2 bed 1 bath unit, 2 bed 1 bath unit, and a 1 bed 1 bath unit. 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

  101 E Lexington Ave, Winchester, KY 40391
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  $189,500

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft

  109 Quail Ridge Rd, Winchester, KY 40391

  Move-In Ready Brick Townhome with Garage and Fireplace Step into this charming brick townhome offering comfort, style, and convenience in every detail. The spacious living room features a cozy fireplace, soft neutral tones, and natural light that make it easy to feel at home. The open layout flows to the kitchen and dining area, creating the perfect setting for everyday living or entertaining

  Kim Dice EXP Realty, LLC

  109 Quail Ridge Rd, Winchester, KY 40391
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  $849,900

  • 4 Beds
  • 3.5 Baths
  • 4,922 Sq Ft

  2509 Mount Sterling Rd, Winchester, KY 40391

  Embrace Bluegrass living with this beautiful fieldstone ranch on 10+ acres in the heart of horse country. Just minutes from interstate access, yet surrounded by rolling hills and scenic views, this mini farm offers a larger barn with 6 stalls, including water and electric connection, 90 foot roof hangover on the barn, 5 paddocks, each with their own gate and water ran along each paddock. The home

  Josh Wood Freedom Realty & Property Management

  2509 Mount Sterling Rd, Winchester, KY 40391
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  $249,000

  • 3 Beds
  • 2 Baths
  • 1,534 Sq Ft

  646 Laura Dr, Winchester, KY 40391

  Three bedrooms ranch, that has been updated with a new kitchen, with granite tops ,new appliances, new flooring ,new interior paintiing ,plus much more, located in Verna Hills S/D located between Winchester and Lexington . Owner/Agent

  Garry Milton Milton and Associates Real Estate

  646 Laura Dr, Winchester, KY 40391
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  /7

  $190,000

  • 3 Beds
  • 2 Baths
  • 1,116 Sq Ft

  41 7th St, Winchester, KY 40391

  Welcome to 41 7th Street! This all-brick ranch features 3 bedrooms, 2 full baths, and beautiful hardwood floors throughout the living room, hallway, and bedrooms. Tucked at the end of the street, the property offers added privacy and peaceful farm views behind the home. Enjoy newer windows, a new HVAC system, and a new water heater for added comfort and efficiency. The attached garage provides

  Austina Bruton Re/Max Elite Realty - Hamburg

  41 7th St, Winchester, KY 40391
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  $234,000

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  209 Allan Place, Winchester, KY 40391

  Charming 3 Bedroom Home with Vaulted Ceilings and Wooded Views Welcome to this inviting 3-bedroom, 2-bath home offering an open-concept layout filled with natural light and soaring vaulted ceilings. The spacious living area flows seamlessly into the kitchen and dining spaces—perfect for both everyday living and entertaining. Enjoy peace of mind with a brand-new HVAC system, Gutter guards and

  Julie Wiggington RE/MAX Creative, Winchester

  209 Allan Place, Winchester, KY 40391
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  $110,000

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  400 Wexford Dr, Winchester, KY 40391

  Welcome! This home offers a practical layout with 3 bedrooms and 2 baths on a manageable 0.2-acre lot. The interior has been well maintained, and fenced backyard creates a private outdoor space ideal for gatherings, pets, or future improvements. A detached 2-car garage provides secure parking and storage. Approximately 5 minutes to downtown Winchester and 15 minutes to Lexington, positioning the

  Katie Allen Keller Williams Legacy Group

  400 Wexford Dr, Winchester, KY 40391
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  $230,000

  • 2 Beds
  • 1 Bath
  • 1,484 Sq Ft

  605 College St, Winchester, KY 40391

  Brick ranch in the College Park neighborhood. Large living area and kitchen with updated appliances and mechanicals (water heater and heat pump). The previous owner water proofed the basement and a new garage door has been installed. Bonus room could be utilized as an additional living room or bedroom.

  Steve Adams Steven D Adams Real Estate Services, LLC

  605 College St, Winchester, KY 40391
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  $102,000

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft

  39 S Highland St, Winchester, KY 40391

  Here's your chance to own a nice investment property. This Single Family home has 2 bedrooms and 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

  39 S Highland St, Winchester, KY 40391
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  /12

  $144,000

  • 3 Beds
  • 1 Bath
  • 805 Sq Ft

  150 Cook Ave, Winchester, KY 40391

  Here's your chance to own a nice investment property. This has a single family has 3 bedrooms and 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

  150 Cook Ave, Winchester, KY 40391
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  $405,000

  • 8 Beds
  • 8 Baths
  • 4,000 Sq Ft

  17 W Lexington Ave, Winchester, KY 40391

  Investment Opportunity in the Heart of Downtown Winchester! Discover 17 W. Lexington Avenue — a converted commercial building now featuring 8 studio/one-bedroom apartments. Each unit includes a full kitchen and private bath, offering the perfect blend of comfort and convenience for tenants. This turn-key multifamily property is ideally situated in historic downtown Winchester, within walking

  Joshua Lynch The Brokerage

  17 W Lexington Ave, Winchester, KY 40391
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  $450,000

  550 E Broadway St, Winchester, KY 40391

  Prime land located on the outskirts of Winchester ready for possible development. Parcel has frontage on both East Broadway and Washington Street. Land is currently zoned A-1. Utilities available. The future awaits!!!

  Keith Wilson Coldwell Banker McMahan

  550 E Broadway St, Winchester, KY 40391
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  /12

  $194,900

  • 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. Main home has been completely remodeled but guest home will require major renevations. 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 month to

  A. Rebecca Woods Woods Realty Group

  175 Magnolia St, Winchester, KY 40391
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  $450,000

  • 5 Beds
  • 3 Baths
  • 3,718 Sq Ft

  1503 Schollsville Rd, Winchester, KY 40391

  Do you ever wonder what it would be like to live in the days of "Gone with the Wind"? Well, here is your chance to own your own personal "Tara". Spacious country home with acreage suitable for children, pets, and livestock. This home is perfect for escaping city life and crowds. Home consists of 5 bedrooms, 3 full bathrooms, Living Room, Dining Room, large Kitchen, room for an office or craft

  Keith Wilson Coldwell Banker McMahan

  1503 Schollsville Rd, Winchester, KY 40391

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