201

Homes for Sale in 40391

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  • /51

    $775,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 3.5 Baths
    • 2,904 Sq Ft

    1783 Gay Evans Rd, Winchester, KY 40391

    Welcome to your dream homestead retreat! Tucked away on 7.27 beautiful acres, this stunning 5-bedroom, 4-bath home offers the perfect blend of comfort, function, and country living. From the inviting front porch sunsets to the resort-style outdoor space, this property has everything you've been searching for. Step inside to the two story foyer that leads to an open-concept main level featuring

    Lucy Martin Jenkins United Real Estate Bluegrass

    1783 Gay Evans Rd, Winchester, KY 40391
  • /100

    $1,789,000

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

    3166 Colby Rd, Winchester, KY 40391

    PRICE REDUCED and sellers are offering a 25,000 allowance at closing to spend as you wish!! Welcome to this beautiful 33± acre estate, offering the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, retains timeless character and can be registered with the Historical Home Society. Enjoy stunning mountain views — located at one of

    Alyssa M Boley Coldwell Banker McMahan

    3166 Colby Rd, Winchester, KY 40391
  • /2

    $1,200,000

    • 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
  • /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
  • /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
  • /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
  • /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
  • /30

    $234,900

    • 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
  • /2

    $150,000

    • Land
    • 2.77 Acres
    • $54,152 per Acre

    3385 Colby Rd, Winchester, KY 40391

    Small acreage lot on Colby Road! Accessed by easement from neighbors driveway.

    Steve Adams Steven D Adams Real Estate Services, LLC

    3385 Colby Rd, Winchester, KY 40391
  • /17

    $285,000

    • Land
    • 14.51 Acres
    • $19,642 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
  • /2

    $10,000

    • Land
    • 0.06 Acre
    • $166,667 per Acre

    75 4th St, Winchester, KY 40391

    Explore the opportunity to build your next home or investment property on this 0.06-acre residential lot located at 75 4th Street. Nestled in an established neighborhood, this lot offers convenient access to local amenities, schools, and nearby roadways. With public utilities available in the area, it's a great option for new construction or future development. Whether you're a builder, investor,

    Bob Sophiea eXp Realty, LLC

    75 4th St, Winchester, KY 40391
  • /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
  • /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
  • /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
  • /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
  • /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
  • /25

    $295,000

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

    398 Pine Ridge Rd, Winchester, KY 40391

    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 you walk in. Enjoy the outdoors from the

    Amie Hieneman ERA Select Real Estate

    398 Pine Ridge Rd, Winchester, KY 40391
  • /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
  • /87

    $3,100,000

    • 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
  • /33

    $354,900

    • 5 Beds
    • 2 Baths
    • 1,952 Sq Ft

    1270 Sewell Shop Rd, Winchester, KY 40391

    Country Living with Convenience — 5 Fenced Acres in Winchester, KY Enjoy the perfect blend of peaceful country living and easy access to town with this well-maintained home on 5 fully fenced acres in Winchester, KY. Conveniently located just 30 minutes to Lexington, 5 miles to I-64, 10 minutes to Mt. Sterling, and 15 minutes to Winchester, this property offers country living without sacrificing

    Meggan Batey Keller Williams Legacy Group

    1270 Sewell Shop Rd, Winchester, KY 40391
  • /3

    $70,000

    • Land
    • 2.04 Acres
    • $34,314 per Acre

    150 Spencer Ln, Winchester, KY 40391

    Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Or hold as investment property and let the land grow in value. This lot totaling 2.041 acres, offer 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 the beauty and tranquility. Don't miss your opportunity to own

    Kathryn Cheuvront Coldwell Banker McMahan

    150 Spencer Ln, Winchester, KY 40391
  • /31

    $205,000

    • 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
  • /10

    $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
  • /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
  • /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
  • /9

    $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
  • /4

    $137,500

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

    12569 Ironworks Rd, 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 gows 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

    12569 Ironworks Rd, Winchester, KY 40391
  • /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
  • /2

    $42,500

    • Land
    • 0.26 Acre
    • $163,462 per Acre

    105 Bella Ct, Winchester, KY 40391

    Jo Gawthrop Keller Williams Bluegrass Realty

    105 Bella Ct, Winchester, KY 40391
  • /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
  • /5

    $450,000

    5127 Combs Ferry Rd, Ford, KY 40391

    Scenic 14+ Acres of Prime Farmland in the Heart of the Bluegrass! Whether you're dreaming of starting a small farm, designing your ideal homestead, or simply building your custom country home with room to roam, this property offers the perfect blend of space, beauty, tranquility, and convenience. Enjoy peaceful rural living with open skies and scenic countryside views, surrounded by picturesque

    John Martin Exit Realty Crutcher Frankfort

    5127 Combs Ferry Rd, Ford, KY 40391
  • /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
  • /12

    $297,000

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

    327 Newcastle Ln, Winchester, KY 40391

    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 that overlooks the main floor. Upstairs are 3 additional bedrooms and a full bathroom. Fenced yard and covered patio to

    Huong Dunn Bluegrass Property Exchange

    327 Newcastle Ln, Winchester, KY 40391
  • /26

    $184,000

    • 2 Beds
    • 1.5 Baths
    • 1,102 Sq Ft

    356 Colby Ridge Blvd, Winchester, KY 40391

    This cozy 2-bedroom, 1.5-bath home is the perfect fit for first-time buyers or anyone looking to expand their investment portfolio. The inviting living room features a propane-operated fireplace that provides a reliable backup heat source. The spacious primary bedroom includes his-and-her closets, and both bedrooms are equipped with additional split units for personalized comfort. A full

    Nena Honaker Tom Goebel & Company

    356 Colby Ridge Blvd, Winchester, KY 40391
  • /43

    $269,000

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

    564 Trapp-Goffs Corner Rd, Winchester, KY 40391

    Private 12-Acre Property in Winchester, KY - Convenient to Lexington & Red River Gorge This 3-bedroom, 2-bath single-family home with an office/flex room is situated on 12 acres in Winchester, KY, offering a combination of open and primarily wooded land. The property is located less than 40 minutes from Lexington and approximately 30 minutes from Red River Gorge. The home offers 1,960 square feet

    Felicia Mayes The Real Estate Co.

    564 Trapp-Goffs Corner Rd, Winchester, KY 40391
  • /103

    $3,500,000

    • 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
  • /2

    $100,000

    • Land
    • 0.37 Acre
    • $270,270 per Acre

    225 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

    225 Jacob Ct, Winchester, KY 40391
  • /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
  • /100

    $429,900

    • 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

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