Homes for Sale near George Rogers Clark High School

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  $45,000

  1559 Amster Grove Rd, Winchester, KY 40391

  Looking for your next investment or weekend escape? This unique property offers two dwellings on one lot, right along the KY River. While it needs a full restoration, the possibilities are endless—whether you're dreaming of a private vacation retreat, a charming getaway spot, or a high-income short-term rental, this is a diamond in the rough ready to shine. Key Highlights: Two dwellings on one

  Erin Lewis Christies International Real Estate Bluegrass

  1559 Amster Grove Rd, Winchester, KY 40391
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  /34

  $265,000

  • Land
  • 6.08 Acres
  • $43,586 per Acre

  190 Privacy Ln, Winchester, KY 40391

  6.08 acres settled in Clark County with access from both Privacy Ln and Little Stoner Rd. This property boasts a 30x56 with 10 foot wall Kentucky Steel Truss building with concrete floors, gas and wood burning heat, full bath, and a car lift. Additionally, there is a barn with a 3 bay shed attached.

  Jason Joseph Keller Williams Commonwealth

  190 Privacy Ln, Winchester, KY 40391
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  /26

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,295 Sq Ft

  175 Waterworks Rd, Winchester, KY 40391

  The country house you have been looking for! 3 bed, 2 bath with an amazing front porch where you can sit and view the small stream in the front yard! Sitting on 3.17 acres with approximately 735 feet of road frontage which should allow for division for a second lot / home. 565 sq ft all metal detached garage, a livestock barn with 3 stalls, and a back deck with farm views. High speed internet

  Jason Townsend Kentucky Residential Real Estate, LLC

  175 Waterworks Rd, Winchester, KY 40391
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  /4

  $25,000

  • Land
  • 0.17 Acre
  • $147,059 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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  /24

  $199,900

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

  27 Ashland Ave, Winchester, KY 40391

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

  Robin Mobley-Mosher Marshall Lane Real Estate - Lexington

  27 Ashland Ave, Winchester, KY 40391
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  /13

  $150,000

  • 2 Beds
  • 1 Bath
  • 1 Sq Ft

  208 4th St, Winchester, KY 40391

  Discover the potential of this spacious 0.27-acre residential home nestled in a neighborhood community on clear and level land located in a Cul-de-sac of Lincoln Park Subdivision. This Property features 2-bedrooms, 1-Bathroom, a large family room with a fireplace. There is also a large versatile barn on the property as well. This could be an investment opportunity as well, for ideal savvy

  Anita McDermott Keller Williams Bluegrass Realty

  208 4th St, Winchester, KY 40391
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  /21

  $139,000

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft

  9 Linden Ave, Winchester, KY 40391

  Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
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  /47

  $375,000

  • 8 Beds
  • 4 Baths
  • 3,706 Sq Ft

  23 1/2 Wheeler Ave, Winchester, KY 40391

  Prime investment opportunity in Winchester! This 4-plex offers four unique 2-bedroom, 1-bath units, each approximately 900 sqft, with washer/dryer hookups and kitchen appliances included. Tenants enjoy a quiet neighborhood setting just steps from College Park, close to the Public Library and downtown. Alley access for parking makes it feel private and secluded. Units feature wide hallways,

  Michelle Blackburn RE/MAX Creative, Winchester

  23 1/2 Wheeler Ave, Winchester, KY 40391
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  /20

  $149,900

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  103 Yorktowne Ct, Winchester, KY 40391

  Affordable and move-in ready! This home will qualify for FHA, VA &/or Rural Housing Loan. This charming 3 bedroom, 1 bath home offers the perfect opportunity for first-time buyers, down-sizers, or investors. With a welcoming layout, comfortable living spaces, and a great location in Winchester, this property is an excellent value in today's market. Enjoy the convenience of nearby shopping,

  Susy Esquivel Allied Realty

  103 Yorktowne Ct, Winchester, KY 40391
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  /67

  $499,000

  • 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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  /34

  $289,000

  • 4 Beds
  • 3 Baths
  • 1,850 Sq Ft

  20 Bon-Haven Ave, Winchester, KY 40391

  Welcome to 20 Bon Haven Avenue, a beautifully renovated 4-bedroom, 3 full bathroom home ideally located directly across from the new Legacy Grove Park in Winchester, KY. This spacious residence blends modern upgrades with timeless charm, offering the perfect retreat for families and entertainers alike.Step inside to find a bright and airy open floor plan, highlighted by brand-new plumbing and

  Jacqueline Marchildon Lifstyl Real Estate

  20 Bon-Haven Ave, Winchester, KY 40391
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  /4

  $235,000

  • Land
  • 8.09 Acres
  • $29,048 per Acre

  2110 Athens Boonesboro Rd, Ford, KY 40391

  Prime building lot - 8.092 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). 2110 approved for its own 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

  2110 Athens Boonesboro Rd, Ford, KY 40391
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  /53

  $449,000

  • 4 Beds
  • 3 Baths
  • 2,844 Sq Ft

  129 Lana Ln, Winchester, KY 40391

  Check out the price adjustment! Stunning renovated 4-BR,3BA brick ranch with walkout basement, in-ground pool & pool house! The pool will be winterized this week! See it before the cover goes on! This home has undergone extensive remodeling to improve traffic flow while preserving distinct living spaces. These updates create a seamless and intuitive flow through, enhancing both functionality

  Jo Gawthrop Keller Williams Bluegrass Realty

  129 Lana Ln, Winchester, KY 40391
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  /59

  $580,000

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

  670 Lillies Ferry Rd, Winchester, KY 40391

  Escape to this serene and private 12+ acre property, boasting a 3BR/2BA home sitting on a partially finished walkout basement, that provides ample space for 2 more bedrooms, playroom, or additional living area. This charming home has lots of recent upgrades, including a brand new HVAC system. The exterior of the home has been upgraded with new energy-efficient windows and exterior doors, along

  Jennifer Helton EXP Realty, LLC

  670 Lillies Ferry Rd, Winchester, KY 40391
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  /25

  $309,000

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

  202 Dubuy Dr, Winchester, KY 40391

  Welcome to this move-in ready 3-bedroom, 2.5-bath home built in 2022. With 1,745 sq. ft., a finished walk-out basement, and thoughtful upgrades, it's designed for comfort with a modern touch.The kitchen features upgraded high-gloss cabinetry, custom granite countertops, and stainless steel appliances. Inside, waterproof luxury vinyl plank (LVP) flooring runs throughout the whole home,

  Donna Mink Mink Realty

  202 Dubuy Dr, Winchester, KY 40391
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  /94

  $849,900

  • 4 Beds
  • 3.5 Baths
  • 4,584 Sq Ft

  4040 Muddy Creek Rd, Winchester, KY 40391

  A Farmhouse Retreat with Timeless Craftsmanship on 13.6 AcresNestled on 13.6 rolling acres in Clark County, this custom built farmhouse captivates with soaring tongue-and-groove ceilings, rich woodwork, and thoughtful craftsmanship that sets this home apart. Oversized doors, custom cabinetry, and detailed finishes showcase the quality throughout, while two wood-burning fireplaces with

  Julie Wiggington RE/MAX Creative, Winchester

  4040 Muddy Creek Rd, Winchester, KY 40391
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  /63

  $1,149,000

  • 3 Beds
  • 3.5 Baths
  • 3,672 Sq Ft

  2100 Irvine Rd Unit 40391, Winchester, KY 40391

  This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths, loft/bedroom/full bath upstairs,

  Mila Ensor Ensor Real Estate, LLC

  2100 Irvine Rd Unit 40391, Winchester, KY 40391
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  /10

  $100,000

  • Land
  • 3.91 Acres
  • $25,575 per Acre

  6345 Muddy Creek Rd, Winchester, KY 40391

  Beautiful lot in Clark County with just under four acres. Owner/ Agent property. Deed restrictions apply

  Chase Parrish Taylor Real Estate, LLC

  6345 Muddy Creek Rd, Winchester, KY 40391
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  /11

  $100,000

  • Land
  • 3.91 Acres
  • $25,575 per Acre

  6413 Muddy Creek Rd, Winchester, KY 40391

  Beautiful lot in Clark County with just under four acres. Septic tank and utilities already on site. Buyer to confirm condition. Owner/ Agent property. Deed restrictions apply. Link to 3D model of lot:

  Chase Parrish Taylor Real Estate, LLC

  6413 Muddy Creek Rd, Winchester, KY 40391
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  /6

  $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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  /39

  $612,900

  • 4 Beds
  • 5 Baths
  • 4,374 Sq Ft

  600 Boone Ave, Winchester, KY 40391

  Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the

  Holly Goeing The Agency

  600 Boone Ave, Winchester, KY 40391
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  /11

  $50,000

  • Land
  • 0.41 Acre
  • $121,951 per Acre

  308 Duclair Dr, Winchester, KY 40391

  Tucked away on a quiet cul-de-sac in Mallard Place, this .41-acre lot is ready for your vision. Imagine your dream home in a neighborhood known for its charm and convenience. Bring your house plans—your future starts here!

  Joseph Miller Keller Williams Commonwealth

  308 Duclair Dr, Winchester, KY 40391
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  /84

  $879,900

  • 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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  /37

  $1,595,000

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

  2 N Main St, Winchester, KY 40391

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

  Blanca Cheung Tsubaki Group, LLC

  2 N Main St, Winchester, KY 40391
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  /6

  $171,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  102 W Hickman St, Winchester, KY 40391

  102 W Hickman St, Winchester, KY 40391Cozy and full of potential! This 11⁄2-story home offers 2 bedrooms and 1 bathroom, making it a great fit for a small household or as part of a rental investment portfolio. Currently used as a rental, the property features a functional layout with living spaces on the main floor and additional space upstairs. Located on a quiet street yet close to downtown

  David Espinosa Bluegrass Realty Pros, Inc

  102 W Hickman St, Winchester, KY 40391
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  /103

  $3,330,000

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 78-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
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  /17

  $299,000

  • Land
  • 14.51 Acres
  • $20,606 per Acre

  3056 Irvine Rd, Winchester, KY 40391

  Own a genuine piece of Kentucky splendor! Beautiful 14.5 acres of gently rolling land is ideal for building your custom home! The property offers creek access and a barn with electric and water. Don't miss this opportunity to own a farm only 20 miles to Hamburg and 5 miles to Winchester Bypass. No city sewage. Deed restrictions apply. Additional parcel with 11.36 acres is also available. Perfect

  Lura Justice Rector Hayden Realtors

  3056 Irvine Rd, Winchester, KY 40391
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  /4

  $199,900

  • Land
  • 11.36 Acres
  • $17,597 per Acre

  2996 Irvine Rd, Winchester, KY 40391

  Are you looking to build your dream home in a quiet country setting with easy access to the Interstate? Look no further! This property offers it all! Gorgeous setting with the best views and creek access. This lovely farm is 11.36 acres of gently rolling country land, in a highly desirable area with easy access to interstate 64, the Mountain Parkway and Hamburg. No city sewage. Deed restrictions

  Lura Justice Rector Hayden Realtors

  2996 Irvine Rd, Winchester, KY 40391
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  /22

  $225,000

  • 4 Beds
  • 2 Baths
  • 1,370 Sq Ft

  521 Acadia Way, Winchester, KY 40391

  This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

  Tyler I Back The Brokerage

  521 Acadia Way, Winchester, KY 40391
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  /62

  $259,500

  • 3 Beds
  • 2 Baths
  • 1,247 Sq Ft

  3614 Stamper Dr, Winchester, KY 40391

  Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

  Darrell Tackett Dream Maker Realty, LLC

  3614 Stamper Dr, Winchester, KY 40391
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  /85

  $609,900

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

  180 Casa Landa Way, Winchester, KY 40391

  This stately yet inviting residence in the highly desirable Stoney Brook subdivision offers the perfect blend of elegance and comfort. Thoughtfully designed for everyday living and entertaining, the home features generously sized rooms throughout.The main level includes formal living and dining spaces, a convenient half bath, and a beautifully appointed kitchen with granite countertops,

  Janna Smith United Real Estate Bluegrass

  180 Casa Landa Way, Winchester, KY 40391
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  /25

  $186,500

  • 3 Beds
  • 1 Bath
  • 1,443 Sq Ft

  31 Vine St, Winchester, KY 40391

  Welcome to this beautifully updated 3-bedroom, 1-bath home, perfectly situated in the vibrant heart of Winchester. Bursting with charm and character, this home offers the best of modern updates and classic appeal. Step inside to discover a bright, open living area with new flooring, fresh paint, and stylish finishes throughout. The updated kitchen features sleek cabinetry, granite countertops,

  Jana Hooten Rock N' Realty LLC

  31 Vine St, Winchester, KY 40391
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  /99

  $749,000

  • 4 Beds
  • 4 Baths
  • 4,644 Sq Ft

  110 Camelot Dr, Winchester, KY 40391

  Don't miss this rare opportunity to abide in one of Winchester's finest locations, Camelot Drive. A hidden gem tucked away in the back of Hampton Manor, this home boasts space and privacy on an idyllic cul-de-sac just off Boone Avenue. Details such as crown molding, built-in cabinetry, high ceilings, 2 fireplaces, transom windows, and hardwood floors fill this home with character and charm.

  Joyce Ratliff Tom Goebel & Company

  110 Camelot Dr, Winchester, KY 40391
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  /58

  $525,000

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

  808 Bypass Rd, Winchester, KY 40391

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

  Diana C Brooker Lifstyl Real Estate

  808 Bypass Rd, Winchester, KY 40391
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  /2

  $195,000

  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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  /4

  $100,000

  • Land
  • 2.62 Acres
  • $38,168 per Acre

  100 Spencer Ln, Winchester, KY 40391

  Eskippakithiki overlooks development. Has a 2.615 acre lot (parcel #8) available for sale waiting for you to build your dream home with beautiful views of serene countryside.

  Priscila Hale FC Tucker Bluegrass

  100 Spencer Ln, Winchester, KY 40391
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  /32

  $399,500

  750 Providence Ln, Winchester, KY 40391

  Welcome to your own slice of country paradise tucked away in southern Clark County! This 51+ acre tract offers a mixture of cleared pasture and mature woods, ideal for a variety of uses including cattle, crops, horses, recreation, or even your dream home site. Currently enjoyed as a private recreational family farm, the property already has electricity in place and features a cistern at an old

  Michelle Blackburn RE/MAX Creative, Winchester

  750 Providence Ln, Winchester, KY 40391
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  /2

  $14,100,000

  • Land
  • 274.52 Acres
  • $51,362 per Acre

  2395 Paris Rd, Winchester, KY 40391

  NOW PRE-SELLING: Deerlawn Development is Winchester, Ky's most anticipated residential development—an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods.
 Located at 2395 Paris Road, and positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 single-family

  Melia Hord Keller Williams Bluegrass Realty

  2395 Paris Rd, Winchester, KY 40391
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  /6

  $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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  /9

  $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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