Winchester, KY Homes for Sale with Acreage

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  /18

  $515,000

  $41K PRICE DROP

  • 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

  110 White Conkwright Rd, Winchester, KY 40391
• Explore Winchester

• 

  

  

  /74

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  2725 Goshen Rd, Winchester, KY 40391

  Welcome to this one-owner home offering the perfect combination of space, thoughtful updates, and country living! Built in 1996 and situated on 1.67 beautiful acres, this well-maintained 3-bedroom, 2-bath home features 1,344 square feet of comfortable living space with numerous improvements already completed for its next owner. Inside, you'll find updated interior paint, durable LifeProof

  

  Christa Joynt

  Keller Williams Commonwealth

  2725 Goshen Rd, Winchester, KY 40391
• 

  

  /2

  $882,000

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

  Lot 1 - 7 Plantations Dr, Winchester, KY 40391

  NOW SELLING PHASE ONE: 7 of the 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

  

  Melia Hord

  MELIA Realty LLC

  Lot 1 - 7 Plantations Dr, Winchester, KY 40391
• 

  

  

  /23

  $250,000

  • Land
  • 14.51 Acres
  • $17,228 per Acre

  3056 Irvine Rd, Winchester, KY 40391

  Discover the perfect blend of beauty, privacy, and opportunity with this stunning 14.511-acre tract on Irvine Road. Featuring gently rolling hills, this property offers multiple ideal building sites to bring your dream home to life, whether you're envisioning a modern farmhouse, barndominium, or private country retreat. A barn is already in place, adding immediate functionality for storage,

  

  Christa Joynt

  Keller Williams Commonwealth

  3056 Irvine Rd, Winchester, KY 40391
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  /21

  $175,000

  • Land
  • 11.36 Acres
  • $15,402 per Acre

  2996 Irvine Rd, Winchester, KY 40391

  Discover the perfect blend of convenience and countryside charm with this beautiful 11+ acre tract located just outside of Winchester in Clark County. Offering gently rolling terrain and multiple potential building sites, this property provides an ideal setting for your dream home, mini-farm, or private retreat.Enjoy the peace and privacy of rural living without sacrificing accessibility and just

  

  Christa Joynt

  Keller Williams Commonwealth

  2996 Irvine Rd, Winchester, KY 40391
• 

  

  /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
• 

  

  /46

  $749,900

  • 3 Beds
  • 2.5 Baths
  • 2,735 Sq Ft

  2180 Big Stoner Rd, Winchester, KY 40391

  Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides

  

  Ashley Barreto

  Indigo & Co

  2180 Big Stoner Rd, Winchester, KY 40391
• 

  /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 homes, and

  

  Melia Hord

  MELIA Realty LLC

  2395 Paris Rd, Winchester, KY 40391
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  /127

  $3,450,000

  • 2 Beds
  • 2.5 Baths
  • 2,725 Sq Ft

  510 - 612 Quisenberry Ln, Winchester, KY 40391

  Adjoining the banks of the Lower Howard's Creek in Clark County lies a very special 145.6± acre farm. With some of the oldest settlements in the county, this region near the Old Stone Church (or Old Providence Church) is immensely historic. Daniel Boone's first eleven surveys in Kentucky were conducted for the Bush family, early inhabitants of the area and farm. With gated stone entrances and

  Zach Davis Kirkpatrick & Company

  510 - 612 Quisenberry Ln, Winchester, KY 40391
• 

  

  /19

  $189,000

  $20K PRICE DROP

  • Land
  • 41.69 Acres
  • $4,534 per Acre

  2697 Pine Ridge Rd, Winchester, KY 40391

  Escape to your own private retreat with this stunning 41.6± acre wooded tract nestled in the scenic countryside of Winchester, Kentucky. This expansive property offers a rare opportunity to own a secluded slice of nature, perfect for a private estate, recreational getaway, or hunting retreat. With rich with mature timber, this land presents a lot of natural beauty. A network of cleared trails and

  Derek Blankenship Keller Williams Commonwealth

  2697 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /17

  $260,000

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  280 Pine Ridge Rd, Winchester, KY 40391

  This listing includes 3 lots in total, 251, 270 and 280 Pine Ridge Rd. All total 12.04 Acres per the PVA. The home is being sold as is.Public Remarks: Bring your vision to life on 12+ beautiful acres in Winchester! This 3-bedroom, 1-bath home offers the charm of a 1964 build and the opportunity to create your own private retreat. With plenty of room for gardens, animals, workshops, or

  Derek Blankenship Overland Properties Group @ KW Commonwealth

  280 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /19

  $460,000

  $39K PRICE DROP

  • Land
  • 36.94 Acres
  • $12,453 per Acre

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391

  Don't miss this rare chance to own 36.45 premium acres on the outskirts of Winchesteran unbeatable blend of open farmland, development potential, and a truly top-tier location. Just minutes from I-64 and a quick drive to Lexington, this tract offers the convenience buyers want with the space and freedom they rarely find. The gorgeous rolling fields make this property ideal for farming, hay

  Greg Meade Whitetail Properties Real Estate

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391
• 

  /2

  $1,200,000

  $596K PRICE INCREASE

  • Land
  • 24.15 Acres
  • $49,689 per Acre

  1395 Two Mile Rd, Winchester, KY 40391

  PLANNED DEVELOPMENT INVESTMENT INVESTMENT OPPORTUNITY! Already zoned Planned Development! There is an approximately 24 acre tract zoned for all forms of Residential use. (In addition there is an approximately 21 acre Residential tract that adjoins the Winchester Country Club. The two Residential tracts have access to gravity flow sewer. Sewer maps available. The remaining

  Garnett Davis Tom Goebel & Company

  1395 Two Mile Rd, Winchester, KY 40391
• 

  

  /3

  $399,000

  • Land
  • 11.3 Acres
  • $35,310 per Acre

  0 Fairholme Way, Winchester, KY 40391

  11 acres of golf course adjacent land with development plan. Owner/Broker. Road and utility estimates available upon request. A list of individuals interested in lots available upon contract.

  Steve Adams Steven D Adams Real Estate Services, LLC

  0 Fairholme Way, Winchester, KY 40391
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  /15

  $128,800

  • Land
  • 2.3 Acres
  • $56,000 per Acre

  110 Knox Ct, Winchester, KY 40391

  This exceptional 2.3 acre homesite offers the perfect canvas to bring your vision to life. With ample space, a prime cul-de-sac setting, and stunning surroundings, it's an ideal opportunity to create the custom home you've always wanted. Located in The Reserve, one of Winchester's premier subdivisions, this property boasts scenic daytime views and unforgettable sunsets each evening. Enjoy the

  Jarran Thomas The Agency

  110 Knox Ct, Winchester, KY 40391
• 

  /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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  /8

  $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

  $101K PRICE DROP

  • 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 with 3,168 ft of road frontage 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

  Zova Rothchild Keller Williams Legacy Group

  3049 Ironworks Rd, Winchester, KY 40391
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  /40

  $498,000

  Open House 9/13

  • 4 Beds
  • 2.5 Baths
  • 2,496 Sq Ft

  1780 Stoner Ephesus Rd, Winchester, KY 40391

  Discover the perfect blend of privacy, comfort, and country elegance on nearly 6 acres of beautiful Kentucky land. This stunning 4 bedroom, 2.5 bath home offers the lifestyle buyers dream of — complete with a sparkling inground pool, generous outdoor space, and thoughtful updates throughout. Set in a peaceful rural setting yet conveniently located just 8 minutes from the Winchester Bypass and 15

  Darrell Tackett Dream Maker Realty, LLC

  1780 Stoner Ephesus Rd, Winchester, KY 40391
• 

  

  /3

  $350,000

  $50K PRICE DROP

  • Land
  • 7.31 Acres
  • $47,880 per Acre

  4095 Basin Springs Rd, Winchester, KY 40391

  Looking for land to build your dream home that is private, but convenient? This 7+ acre beautiful lot is located in Clark County, just 15 minutes from Costco, Hamburg and I-75. No HOA or deed restrictions. The perfect place to build or have a small farm. City water and electricity available at the street. No city sewer.

  Peggy Baldridge HomeFirst Real Estate

  4095 Basin Springs Rd, Winchester, KY 40391
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  /10

  $575,000

  $75K PRICE DROP

  • Land
  • 2.6 Acres
  • $221,154 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, and

  Greg Leveridge Block + Lot Homes

  529 Bullion Blvd Unit 3B, Winchester, KY 40391
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  /38

  $355,000

  $25K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 2,179 Sq Ft

  3359 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Home listed as one bedroom while unofficially has 3 but 2 of them are interior rooms without windows. ( Owners Now Offering to pay up to $5,000 in closing cost and pre-paids on behalf of buyers). Tired of the honking horns , congested traffic, sirens of town living and dreaming of country living, your own slice of paradise? Maybe raising your own garden , owning chickens , goats, horses ,

  Wayne Elkins RE/MAX Creative Realty

  3359 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  

  /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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  /84

  $1,500,000

  • 4 Beds
  • 3 Baths
  • 7,172 Sq Ft

  351 Benton Rd, Winchester, KY 40391

  Welcome to a truly one-of-a-kind Kentucky estate where luxury, craftsmanship, and country living come together on 27 breathtaking acres in Clark County—just 10 minutes from the interstate for an easy commute while still enjoying complete privacy. Built with exceptional quality and thoughtfully designed by its original owner, this custom home offers over 7,000 square feet of living space with 4

  Darienne Hensley Keller Williams Legacy Group

  351 Benton Rd, Winchester, KY 40391
• 

  /2

  $1,800,000

  $2M PRICE INCREASE

  • 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
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  /2

  $195,000

  $2M PRICE DROP

  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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  /50

  $419,900

  $10K PRICE DROP

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

  240 Athens Boonesboro Rd, Winchester, KY 40391

  Rare Investment Opportunity on the Kentucky River! Two incredible homes on 3 beautiful acres — endless potential awaits. Live in the charming log cabin and let the second home pay the mortgage with its long term, reliable tenant already in place. This property offers room to dream: -Build a future campground -Create a private riverside retreat -Expand for additional rentals -Or simply enjoy your

  Darrell Tackett Dream Maker Realty, LLC

  240 Athens Boonesboro Rd, Winchester, KY 40391
• 

  /2

  $100,000

  $10K PRICE INCREASE

  • Land
  • 1.1 Acres
  • $90,909 per Acre

  270 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

  270 Duclair Dr, Winchester, KY 40391
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  /9

  $500,000

  $100K PRICE DROP

  • Land
  • 1.52 Acres
  • $328,947 per Acre

  1005 Early Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

  Whitney Ensor Ensor Real Estate, LLC

  1005 Early Dr, Winchester, KY 40391
• 

  

  /14

  $650,000

  • Land
  • 3 Acres
  • $216,667 per Acre

  205 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 Clean Sweeps and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Homes

  205 Codella Dr, Winchester, KY 40391
• 

  /2

  $67,500

  • Land
  • 1.89 Acres
  • $35,695 per Acre

  250 Spencer Ln, Winchester, KY 40391

  Unique triangular shaped lot in a wooded rural setting, interesting opportunities for privacy in a beautiful area of Clark County where you can enjoy the outdoors and create memories galore.

  Craig Bridgewater Bridgewater Real Estate

  250 Spencer Ln, Winchester, KY 40391
• 

  

  /6

  $110,000

  • Land
  • 2.06 Acres
  • $53,398 per Acre

  1185 Craig Crossing Rd, Winchester, KY 40391

  Lot # 30 contains 2.058 acres of gently rolling land 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

  1185 Craig Crossing Rd, Winchester, KY 40391
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  /120

  $1,595,000

  $100K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 4,518 Sq Ft

  3166 Colby Rd, Winchester, KY 40391

  NEW PRICE!!! Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points

  Alyssa M Boley Coldwell Banker McMahan

  3166 Colby Rd, Winchester, KY 40391
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  /52

  $429,000

  $36K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,942 Sq Ft

  1024 Flanagan Station Rd, Winchester, KY 40391

  Nestled on 8.9 picturesque acres just off Boonesboro Road, this one-of-a-kind property offers the perfect blend of character, privacy, and endless potential. Whether you're dreaming of a horse farm, hobby farm, or simply room to roam, this beautiful property provides plenty of space for horses, livestock, gardening, or enjoying peaceful country living. Inside, you'll find a spacious open-concept

  Brooke Martin RO&CO Real Estate

  1024 Flanagan Station Rd, Winchester, KY 40391
• 

  /2

  $490,000

  $60K PRICE DROP

  • Land
  • 1.53 Acres
  • $320,261 per Acre

  33-41 Winn Ave, Winchester, KY 40391

  Discover a rare opportunity in downtown Winchester with this assemblage of four vacant lots being sold together as a single offering. Zoned L1 and totaling approximately 1.53 acres, this property presents exceptional potential for redevelopment, infill housing, multiunit residential, mixeduse, or commercial concepts in a central location. Situated just steps from local shops, restaurants,

  Bob Sophiea eXp Realty, LLC

  33-41 Winn Ave, Winchester, KY 40391
• 

  /2

  $150,000

  • Land
  • 2.16 Acres
  • $69,444 per Acre

  120 Knox Ct, Winchester, KY 40391

  Looking for a place to build a Upscale home in 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

  120 Knox Ct, Winchester, KY 40391
• 

  

  /29

  $219,900

  • Land
  • 23.83 Acres
  • $9,228 per Acre

  3686 Crowe Ridge Rd, Winchester, KY 40391

  Discover the possibilities with this unique dual-property offering at 3686 & 3688 Crowe Ridge Road. Enjoy the peace and privacy of a beautiful country setting with room to spread out and endless potential. Whether you're looking for a primary residence with additional living space, an investment opportunity, or housing for extended family, this property offers versatility that's hard to find.

  Josh Wood Freedom Realty & Property Management

  3686 Crowe Ridge Rd, Winchester, KY 40391
• 

  

  /63

  $785,000

  • 5 Beds
  • 2.5 Baths
  • 4,676 Sq Ft

  217 Wades Mill Rd, Winchester, KY 40391

  Escape to the peace and privacy of country living with this spacious brick one-and-a-half story home situated on just over 5 acres. With plenty of room to spread out, the main level offers a welcoming foyer, formal dining room, living room with a wood-burning fireplace, kitchen featuring granite countertops, tile backsplash, breakfast nook, and laundry room, along with the primary suite, three

  Michelle Blackburn RE/MAX Creative, Winchester

  217 Wades Mill Rd, Winchester, KY 40391
• 

  

  /15

  $120,000

  • Land
  • 4.14 Acres
  • $28,986 per Acre

  3999 Bybee Rd, Winchester, KY 40391

  Discover the perfect setting for your dream home on this beautiful 4.14-acre tract at 3999 Bybee Road, Winchester, KY 40391. Nestled among the rolling hills of Kentucky's Bluegrass region, this picturesque property offers stunning panoramic countryside views and the peace and privacy you've been searching for. The gently rolling terrain provides multiple potential building sites, giving you the

  Kristey Wood eXp Realty, LLC

  3999 Bybee Rd, Winchester, KY 40391
• 

  

  /55

  $515,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,563 Sq Ft

  935 Stoner-Ephesus Rd, Winchester, KY 40391

  Picture this: over five acres of Kentucky countryside, a handsome ranch-style home, and enough elbow room to finally breathe. This stunning 2,563 square foot retreat delivers the rare combination of refined interior finishes and genuine rural charm, all without sacrificing modern convenience. Inside, discover a generous family room anchored by a striking stone fireplace — the kind of space that

  Timothy Saylor Threshold Real Estate Services

  935 Stoner-Ephesus Rd, Winchester, KY 40391

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