Winchester, KY Homes for Sale

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  $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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  /2

  $110,000

  • Land
  • 0.38 Acre
  • $289,474 per Acre

  200 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

  200 Duclair Dr, Winchester, KY 40391
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  /29

  $289,000

  • 5 Beds
  • 2 Baths
  • 1,838 Sq Ft

  426 E Broadway St, Winchester, KY 40391

  Welcome home to this beautifully reimagined property in Winchester! Originally built in 1945, this 1.5-story home has been completely transformed from the ground up, offering the perfect blend of classic charm and modern peace of mind. With approximately 1,838 square feet, this home has been fully gutted to the studs and thoughtfully rebuilt—featuring all-new electrical, plumbing, HVAC system,

  Alyssa M Boley Coldwell Banker McMahan

  426 E Broadway St, Winchester, KY 40391
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  /16

  $174,900

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  47 Buckner St, Winchester, KY 40391

  This 3-bedroom, 2 full bath home is nestled in a convenient location and ready for new owners. Updates can be admired throughout. Property boats spacious bedrooms including primary bedroom with on-suite, large back yard with garage and so much more. Schedule your showing today!

  Michael Hilario The Agency

  47 Buckner St, Winchester, KY 40391
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  /25

  $425,000

  • Land
  • 25.87 Acres
  • $16,426 per Acre

  2996/3056 Irvine Rd, Winchester, KY 40391

  Rare opportunity to own over 25 acres of beautiful Kentucky countryside on Irvine Road, combining two adjoining tracts into one exceptional offering. With gently rolling hills and multiple ideal building sites, this property provides the perfect setting to create your dream home, private estate, or mini-farm. The land offers a wonderful balance of usability and natural beauty, featuring a scenic

  Christa Joynt Keller Williams Commonwealth

  2996/3056 Irvine Rd, Winchester, KY 40391
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  /94

  $795,000

  • 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 Acres Nestled 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 homemade

  Julie Wiggington RE/MAX Creative, Winchester

  4040 Muddy Creek Rd, Winchester, KY 40391
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  /18

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,190 Sq Ft

  7 Hiawatha Trail, Winchester, KY 40391

  Welcome to 7 Hiawatha Trail in Winchester—a beautifully updated brick ranch that blends timeless character with modern conveniences. Built in 1968, this home has been thoughtfully improved by its current owners, offering a move-in-ready space with stylish upgrades throughout. Inside, you'll find refinished original hardwood floors that bring warmth and charm, complemented by fresh paint and

  Serena Cassidy Coldwell Banker McMahan

  7 Hiawatha Trail, Winchester, KY 40391
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  /103

  $2,650,000

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

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 10-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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  $209,000

  • 4 Beds
  • 2 Baths
  • 2,683 Sq Ft

  217 S Highland St, Winchester, KY 40391

  This Spacious investment property is ready for its new owner. The home features fresh updates throughout, large living spaces and endless possibilities. Schedule your showing while you can!

  Michael Hilario The Agency

  217 S Highland St, Winchester, KY 40391
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  /2

  $110,000

  • Land
  • 0.47 Acre
  • $234,043 per Acre

  139 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

  139 Jacob Ct, Winchester, KY 40391
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  /32

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  528 Estes Dr, Winchester, KY 40391

  Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
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  /2

  $882,000

  • Land
  • 3.93 Acres
  • $224,427 per Acre

  Lot 1 - 12 Plantations Dr, Winchester, KY 40391

  NOW SELLING 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 you to build your New

  Melia Hord Keller Williams Legacy Group

  Lot 1 - 12 Plantations Dr, Winchester, KY 40391
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  /2

  $150,000

  • Land
  • 2.11 Acres
  • $71,090 per Acre

  125 Knox 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

  125 Knox Ct, Winchester, KY 40391
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  /19

  $300,000

  • Land
  • 15.27 Acres
  • $19,652 per Acre

  4025 Jackson Ferry Rd, Winchester, KY 40391

  Opportunities like this are incredibly rare—15.266 combined acres backing to the Kentucky River, offering the ultimate private retreat. Located at the end of a scenic drive, these two tracts are being offered together, creating an expansive recreational property with unmatched access to the water. Ideal for camping, family getaways, or creating a multi-use outdoor haven, this land provides

  Christa Joynt Keller Williams Commonwealth

  4025 Jackson Ferry Rd, Winchester, KY 40391
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  /17

  $129,900

  • 2 Beds
  • 1 Bath
  • 876 Sq Ft

  122 Calloway St, Winchester, KY 40391

  Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless

  Darrell Tackett Dream Maker Realty, LLC

  122 Calloway St, Winchester, KY 40391
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  /25

  $295,000

  • Land
  • 10 Acres
  • $29,500 per Acre

  398 Pine Ridge Rd, Winchester, KY 40391

  **** CONTRACT ACCEPTED WITH 48 KICK OUT***Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment

  Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
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  $1,500,000

  1015 Old Stone Church Rd, Winchester, KY 40391

  Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights

  Walker Mack Bluegrass Property Exchange

  1015 Old Stone Church Rd, Winchester, KY 40391
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  /87

  $2,999,000

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

  3049 Ironworks Rd, Winchester, KY 40391

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

  Zova Rothchild Keller Williams Legacy Group

  3049 Ironworks Rd, Winchester, KY 40391
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  /20

  $180,000

  • Land
  • 10.05 Acres
  • $17,919 per Acre

  3925 Jackson Ferry Rd, Winchester, KY 40391

  This 10.045-acre tract offers the total package...scenic surroundings, river access, and improvements already in place. Situated along a quiet, picturesque drive, the property features a solid barn that has recently been painted and structurally reinforced, adding both character and functionality. With a picturesque build site available, this land is ready for your dream home, hobby farm, and

  Christa Joynt Keller Williams Commonwealth

  3925 Jackson Ferry Rd, Winchester, KY 40391
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  /16

  $1,200,000

  • 16 Beds
  • 16 Baths
  • 7,480 Sq Ft

  16 Linden Ave, Winchester, KY 40391

  You won't want to miss adding this income-producing apartment complex to your portfolio. This property is comprised of 16 one-bedroom/one-bathroom apartments with 100% occupancy. Complex is conveniently located in downtown Winchester and only 20 minutes from Lexington via easy highway access. The building sits on a 0.34 acre lot with 20+ parking spaces. Property has several updates including roof

  Kevin Bradley KB Realty Group

  16 Linden Ave, Winchester, KY 40391
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  /31

  $195,000

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  5434 Pine Ridge Rd, Winchester, KY 40391

  Jim Woodrum RE/MAX Creative, Winchester

  5434 Pine Ridge Rd, Winchester, KY 40391
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  /12

  $160,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  471 Goose Creek Rd, Winchester, KY 40391

  CASH BUYERS! This 3-bedroom, 2-bath manufactured home on 1.49 acres offers strong potential for those looking to renovate, rent, or resell. Property is being sold as-is and will require repairs, making it best suited for cash buyers. Located just minutes from I-64 and convenient to Lexington, this property combines rural privacy with accessibility — a desirable combination for future resale or

  Shari Frasure Keller Williams Commonwealth

  471 Goose Creek Rd, Winchester, KY 40391
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  $775,000

  • Land
  • 2.6 Acres
  • $298,077 per Acre

  529 Bullion Blvd Unit 3B, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided.Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One,

  Greg Leveridge Block + Lot Real Estate

  529 Bullion Blvd Unit 3B, 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 Legacy Group

  308 Duclair Dr, 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 Legacy Group

  2395 Paris Rd, Winchester, KY 40391
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  $785,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft

  425 Alexis Way, Winchester, KY 40391

  Introducing the Highland, an elegant all-brick ranch home offering 4 bedrooms and 2.5 full baths in a thoughtfully designed split-bedroom layout. The spacious primary suite is a true highlight, featuring a luxurious tile shower, separate soaking tub, double vanities, and a large walk-in closet. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for

  Shane Underwood Keller Williams Commonwealth

  425 Alexis Way, Winchester, KY 40391
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  /27

  $388,000

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

  17 W Lexington Ave, Winchester, KY 40391

  Great investment opportunity right in heart Downtown Winchester!!! Welcome to this income producing apartment complex of 8 studio apartments. Two levels of apartments, 4 on the first floor and 4 on the second. Each unit features a living area, full kitchen, and full bathroom. 5 units are currently rented out. The roof was put on 2 years ago. The basement has 2 entrances and could easily be

  Libby VanMeter Marshall Lane Real Estate - Lexington

  17 W Lexington Ave, Winchester, KY 40391
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  /21

  $244,900

  • 3 Beds
  • 1.5 Baths
  • 1,494 Sq Ft

  720 Estes Dr, Winchester, KY 40391

  This charming brick ranch is truly move-in ready. Offering 3 bedrooms, 1.5 baths, a welcoming living room, a cozy den, and kitchen with appliances, this home blends comfort and convenience with ease. Enjoy the natural light and peaceful views from the screened-in sunporch, perfect for relaxing. Updates include new kitchen flooring, refinished hardwood floors, and updated trim that gives the home

  Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  720 Estes Dr, Winchester, KY 40391
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  /13

  $239,900

  • 5 Beds
  • 3 Baths
  • 3,007 Sq Ft

  221 S Highland St, Winchester, KY 40391

  INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered

  Joshua Lynch The Brokerage

  221 S Highland St, Winchester, KY 40391
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  /19

  $125,000

  • Land
  • 4.01 Acres
  • $31,172 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 from the

  Laura Sizemore Kentucky Land and Home

  1940 Athens Boonesboro Rd, Winchester, KY 40391
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  /4

  $137,500

  • Land
  • 3.94 Acres
  • $34,898 per Acre

  150 Spencer Ln, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it grows in value. Offering 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

  Kathryn Cheuvront Coldwell Banker McMahan

  150 Spencer Ln, Winchester, KY 40391
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  /17

  $420,000

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft

  104 Colby Hills Dr, Winchester, KY 40391

  (Reducted 50,000) for fast sell. 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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  /63

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Property is under contract with a 72 hour kickout clause. Enjoy peaceful country living on 17 beautiful acres in Clark County! This 3-bedroom, 2-bath ranch home sits on a scenic stretch of Trapp-Goffs Corner Road and offers the perfect blend of privacy, space, and convenience just minutes from Winchester and an easy drive to Lexington. The home features comfortable main-level living with a

  Cheri Shaffer Lifstyl Real Estate

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  /3

  $84,900

  • Land
  • 3.39 Acres
  • $25,044 per Acre

  160 Rector Ln, Winchester, KY 40391

  UNIQUE Opportunity - 3.39 acres with a small pond - tucked away on a private lane, flat land and totally surrounded by trees. What a unique setting!! Convenience is the key to this property. Water is available at the main road. Internet has been extended down Rector Lane, electricity is accessible for connection. Deed Restrictions apply. Do Not Miss Your Chance to own this SPECIAL piece of land.

  M Gail Cleaver United Real Estate Bluegrass

  160 Rector Ln, Winchester, KY 40391
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  /2

  $299,900

  • 4 Beds
  • 2 Baths
  • 1,960 Sq Ft

  306 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Beautiful Four Bedroom 2 Bathroom Ranch Home On A Finished Basement With Over 2 Acres!! Bring Your Family, Toys, Animals And Enjoy Country Living Close To Mountain Parkway And Close To Two Country Restaurants! Sellers Have Finished Basement To Add An Additional Bedroom, Bathroom And Lots Of Storage!! And Dont Miss The Large Deck With a View!

  Patrick Arvin Keller Williams Commonwealth

  306 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  /2

  $110,000

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

  250 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

  250 Duclair Dr, Winchester, KY 40391
• 

  

  /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 approval,

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
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  /2

  $188,500

  • Land
  • 12.1 Acres
  • $15,579 per Acre

  155 Spring Ridge Way, Winchester, KY 40391

  Great opportunity to develop/ build on 12+ acres. The property has three street stubs adjoining it. Three different concepts are included under documents. They are- R-1E, 4000 sq. Ft lots for 80 lots R-4- 14 Duplexes and 6 4plexes for 52 units R-1D - 6000 sq. Ft. Lots for 41 lots. Utilities are to the property and sewer availability should not be an issue. Please feel free to call the listing

  Jo Gawthrop Keller Williams Bluegrass Realty

  155 Spring Ridge Way, Winchester, KY 40391
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  /12

  $294,900

  • 4 Beds
  • 2.5 Baths
  • 1,693 Sq Ft

  327 Newcastle Ln, Winchester, KY 40391

  Seller is offering $2000 total towards buyers concession (can be used for downpayment, prepaids and closing cost)!! Welcome home to this cozy cute FOUR bedroom house with 2 full bath/ 1 half bath! Rare to find- Primary bedroom and full bath on first floor. Large living area with plenty of sunlight through insulated windows and skylights. This open floorpan also showcases a nice open staircase

  Huong Dunn Bluegrass Property Exchange

  327 Newcastle Ln, Winchester, KY 40391
• 

  /2

  $1,800,000

  • Land
  • 4.36 Acres
  • $412,844 per Acre

  722 Colby Rd Unit 1, Winchester, KY 40391

  Discover an exceptional opportunity for retail investment in the thriving Winchester area. Zoned B-4, this versatile property offers a wide array of possibilities for retail development, providing a strategic location for businesses seeking to establish a prominent presence. With its prime zoning and desirable position within the Winchester area, this property presents a compelling prospect for

  Cheryl Johnston CMI Properties

  722 Colby Rd Unit 1, Winchester, KY 40391

Showing Results 41 - 80, Page 2 of 6