47

Homes for Sale near Shearer Elementary School

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  • /71

    $799,999

    • 4 Beds
    • 2.5 Baths
    • 5,290 Sq Ft

    186 Chardonnay Ct, Winchester, KY 40391

    Step into a world of both comfort and convenience with this beautiful 3/4 bedroom, two and one half bath, perfectly designed for relaxation and entertainment. Key features of this property include outdoor spaces to enjoy morning coffee or quiet evening chats. The cozy back porch extends your living space, ideal for dining and enjoying the tranquil surroundings, The beautifully designed patio

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    (859) 813-4308

    186 Chardonnay Ct, Winchester, KY 40391
  • /36

    $319,900

    • 5 Beds
    • 2 Baths
    • 2,082 Sq Ft

    128 Cherokee Dr, Winchester, KY 40391

    **Open House Sunday 11/16 1-3PM** Welcome to 128 Cherokee Drive, a beautifully maintained home in a quiet and desirable neighborhood. With 5 bedrooms, two full bathrooms, and a second living room on the lower floor, there is plenty of room for the entire family and friends. A spacious backyard , many appealing updates since 2022, and exceptional curb appeal and charm, this home is just waiting

    Agent Photo

    Tyler Hurst

    Thwaites Realtors LLC

    (859) 681-9697

    128 Cherokee Dr, Winchester, KY 40391
  • /22

    $147,000

    • 2 Beds
    • 1 Bath
    • 807 Sq Ft

    3208 Ford Hampton Rd, Winchester, KY 40391

    Escape to a lifestyle defined by the peace and natural beauty of this delightful two bedroom property just steps away from the majestic Kentucky River, this home isn't just a place to iive, it is a dedicated sanctuary whether you are seeking a cozy year round residence or a recreational retreat. One of the standout features is the exceptioal connection to the outdoors with generous porches on

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    (859) 765-6889

    3208 Ford Hampton 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
  • /18

    $499,900 New Construction

    • 4 Beds
    • 3 Baths
    • 2,300 Sq Ft

    414 Fairholme Way, Winchester, KY 40391

    Welcome to Fairholme Estates—where luxury meets comfort! This brand-new ranch-style home offers 4 bedrooms, 3 full baths, and 9' ceilings throughout for a spacious, airy feel. The designer kitchen features a huge island, beautiful finishes, and flows seamlessly into the vaulted great room filled with natural light from large windows. A Jack and Jill bath with separate sinks provides convenience,

    Kristin Ray Lifstyl Real Estate

    414 Fairholme Way, Winchester, KY 40391
  • /30

    $259,900

    • 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
  • /92

    $1,200,000

    • 5 Beds
    • 7 Baths
    • 8,236 Sq Ft

    6237 Bybee Rd, Winchester, KY 40391

    Step into timeless elegance with this breathtaking modern Victorian-style masterpiece, perfectly positioned on 4.39 acres with panoramic views of sunrises, sunsets, and distant mountains. Designed and built by Tom Padgett, this home is rich in character and detail—from hand-hewn wood beam ceilings to Waterford crystal chandeliers. The grand 2-story foyer welcomes you into a flowing layout that

    Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

    6237 Bybee 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
  • /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
  • /22

    $270,000

    • 4 Beds
    • 2 Baths
    • 2,332 Sq Ft

    35 Cherokee Ct, Winchester, KY 40391

    Step into this 4-bedroom, 2 full bath split-foyer home, perfectly designed for comfortable everyday living. The upper level features three generously sized bedrooms, a full bath, a bright living room, kitchen, and dining area—ideal for gathering with family and friends. Just off the kitchen, enjoy easy access to the covered deck overlooking a spacious backyard. The lower level offers even more

    Brenda Rue Keller Williams Bluegrass Realty

    35 Cherokee Ct, Winchester, KY 40391
  • /38

    $389,900

    • 4 Beds
    • 2 Baths
    • 2,659 Sq Ft

    6239 Old Boonesboro Rd, Winchester, KY 40391

    Welcome Home to the beautiful country! If you've been looking for quiet, space, and a place that truly feels like home, this charming Cape Cod on nearly 2 acres in Clark County checks all the boxes. Tucked into a peaceful rural setting yet conveniently located near I-75, I-64 and the Winchester Bypass, this property offers the best of country living with easy access to town. With over 2,600

    Kenya Woods United Real Estate Bluegrass

    6239 Old Boonesboro Rd, 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
  • /19

    $199,900

    • 3 Beds
    • 2 Baths
    • 1,072 Sq Ft

    117 Buffalo Trace, Winchester, KY 40391

    Move-In Ready! 3 bedrooms, 2 bath, brand new kitchen cabinets with stylish butcher block counter tops, fresh light fixtures throughout, and durable, sleek laminate flooring. This home combines comfort and style with updates that make it truly shine. Perfect for families or first-time home buyers! Conveniently located in a great neighborhood. Owner/Agent

    Nena Honaker Tom Goebel & Company

    117 Buffalo Trace, Winchester, KY 40391
  • /31

    $379,717

    • 3 Beds
    • 2.5 Baths
    • 2,636 Sq Ft

    300 Calmes Blvd, Winchester, KY 40391

    Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates . Welcome to your dream home in the highly sought-after Calmes Estates neighborhood! This beautifully maintained 3-bedroom, 2.5-bath residence offers generous living space and a layout perfect for families or entertaining guests. Highlights: *Expansive open-concept living areas *three spacious bedrooms with ample closet space *Two and a half

    Darrell Tackett Dream Maker Realty, LLC

    300 Calmes Blvd, 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
  • /24

    $188,900

    • 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
  • /33

    $225,000

    • 4 Beds
    • 1 Bath
    • 1,743 Sq Ft

    218 E Washington St, Winchester, KY 40391

    Four Bedroom home in Winchester, Ky which includes a bonus room ready for a makeover for whatever you would like to make it. Enjoy a good sized backyard that is fenced in, along with a detached garage.

    Fernando Andrade Rector Hayden Realtors

    218 E Washington St, Winchester, KY 40391
  • /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
  • /2

    $168,000

    • Land
    • 11.34 Acres
    • $14,815 per Acre

    4590 Four Mile Rd, Ford, KY 40391

    **Significant Price Change** Check It Out! Nature lovers property. There is a rock wall at the top with the Four Mile Creek which runs into the Kentucky River across the road. Nearby are restaurants, boat landings, kayaks and historical sights. The trees will keep it private.

    Garnett Davis Tom Goebel & Company

    4590 Four Mile Rd, Ford, KY 40391
  • /36

    $434,500

    • 4 Beds
    • 2.5 Baths
    • 2,747 Sq Ft

    134 Fontaine Blvd, Winchester, KY 40391

    Some homes are just houses—but this one was built for connection, creativity, and meaningful moments. Located in the desirable Oak Hill neighborhood, just minutes from GRC High School, this meticulously maintained 4-bedroom, 2.5-bath home offers the space and flexibility today's families are looking for. Formerly home to the beloved "2 Momma's Cooking for You," the property features a fully

    Craig Bridgewater Bridgewater Real Estate

    134 Fontaine Blvd, Winchester, KY 40391
  • /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
  • /13

    $252,500

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

    221 S Highland St, Winchester, KY 40391

    INVESTOR SPECIAL, could be a great option for an end of year cost seg study and bonus depreciation. 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

    Joshua Lynch The Brokerage

    221 S Highland St, Winchester, KY 40391
  • /13

    $1,300,000

    345 Providence Ln, Winchester, KY 40391

    120 Acres of Scenic Farmland in Winchester, KY. Discover the beauty and tranquility of country living on this remarkable 120-acre farm nestled in the heart of Clark County, Kentucky. Featuring a picturesque mix of rolling pastureland, mature woodlands, and pond, this property offers endless possibilities for farming, livestock, recreation, or building your dream home. Conveniently located just

    Megan McCoy Keller Williams Legacy Group

    345 Providence Ln, Winchester, KY 40391
  • /36

    $345,000

    • 2 Beds
    • 2 Baths
    • 1,568 Sq Ft

    208 Citation Ct, Winchester, KY 40391

    One owner, all electric, 2 BR/2Ba ranch with a bonus room that could be an office or a third bedroom. Great for downsizing or first time homeowner! The open floor great room with ample windows to brighten it supports the handicapped features of the primary bedroom, primary bathroom, garage and more. Enjoy the large pantry off the kitchen area and the island that has room to slide a chair under.

    Garnett Davis Tom Goebel & Company

    208 Citation Ct, Winchester, KY 40391
  • /3

    $146,000

    • 3 Beds
    • 1 Bath
    • 1,020 Sq Ft

    228 Jackson St, Winchester, KY 40391

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

    228 Jackson St, Winchester, KY 40391
  • /4

    $124,900

    • 4 Beds
    • 2.5 Baths
    • 2,131 Sq Ft

    205 E Washington St, Winchester, KY 40391

    PRICE DROP!!! FLIP This House! Seller Has Added A Large Primary Addition And Front Porch. This 4 Bedroom 2 1/1 Bath Home Is Ready For Your Finishes And Has A Fantastic Floor Plan With Large Loft (Whole Home At Stud Level). Finish This Home It Will Be A Showstopper Better Than New Construction With Large Sq Ft What Many Buyers Are Looking For. Great Opportunity To Make Money Or Live In This

    W Patrick Arvin Keller Williams Commonwealth

    205 E Washington St, Winchester, KY 40391
  • /68

    $2,495,000

    • 5 Beds
    • 5 Baths
    • 6,284 Sq Ft

    5039 Combs Ferry Rd, Ford, KY 40391

    This 5 Bedroom, 5 Bathroom home is quietly located in the highly desired Combs Ferry area of Clark County. Location is evident as you are approximately an 8-minute drive to Hamburg as well as 8-minute drive to downtown Winchester. This complete custom home was constructed in 2022. The 6284 sqft boasts custom features including built in appliances, in-ground oversized heated pool with outdoor

    Michael Hilario The Agency

    5039 Combs Ferry Rd, Ford, KY 40391
  • /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
  • /5

    $29,000

    • Land
    • 0.46 Acre
    • $63,043 per Acre

    102 Augusta Dr, Winchester, KY 40391

    This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

    Dale Hatton Dream Maker Realty, LLC

    102 Augusta Dr, Winchester, KY 40391
  • /55

    $425,000

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

    6504 Combs Ferry Rd, Winchester, KY 40391

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

    Lucy Martin Jenkins United Real Estate Bluegrass

    6504 Combs Ferry Rd, Winchester, KY 40391
  • /53

    $265,000

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

    174 Hidden Grove Ln, Winchester, KY 40391

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

    Kathryn Cheuvront Coldwell Banker McMahan

    174 Hidden Grove Ln, Winchester, KY 40391
  • /7

    $180,000

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

    1030 Craig Crossing Rd, Winchester, KY 40391

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

    Keith Wilson Coldwell Banker McMahan

    1030 Craig Crossing Rd, Winchester, KY 40391
  • /14

    $159,900

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

    590 Craig Crossing, Winchester, KY 40391

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

    Keith Wilson Coldwell Banker McMahan

    590 Craig Crossing, Winchester, KY 40391
  • /25

    $248,000

    • 3 Beds
    • 2.5 Baths
    • 1,342 Sq Ft

    120 Jackson St, Winchester, KY 40391

    Step into modern comfort just minutes from the heart of downtown Winchester. This nearly new home blends contemporary style with timeless charm. Featuring bright, open living spaces, and thoughtful upgrades throughout, it offers a move-in-ready opportunity in one of Winchester's most convenient locations.

    Hannah Toole Coldwell Banker McMahan

    120 Jackson St, Winchester, KY 40391
  • /33

    $255,000

    • 3 Beds
    • 1.5 Baths
    • 2,188 Sq Ft

    357 Crescent Ave, Winchester, KY 40391

    Welcome to this charming 3-bedroom, 1.5-bath home situated on a lovely corner lot. Step inside to discover a well-maintained interior with a thoughtful layout that flows effortlessly from room to room. The cozy living area opens to the dining space. You'll also find two versatile flex spaces, each filled with natural light from large windows-perfect for a home office, playroom, or creative

    Samantha Gray National Real Estate

    357 Crescent Ave, Winchester, KY 40391
  • /9

    $206,000

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

    368 Flanagan Station Rd, Winchester, KY 40391

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

    Shari Frasure Keller Williams Commonwealth

    368 Flanagan Station Rd, Winchester, KY 40391
  • /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
  • /34

    $330,000

    • 4 Beds
    • 3 Baths
    • 1,776 Sq Ft

    213 Orchid Ct, Winchester, KY 40391

    Kasey McCarty 5.23 Real Estate

    213 Orchid Ct, Winchester, KY 40391
  • /13

    $245,000

    • 5 Beds
    • 3 Baths
    • 2,445 Sq Ft

    130 E Broadway St, Winchester, KY 40391

    Wonderful investment opportunity! Cash flowing triplex located in the heart of Winchester. One unit has just been renovated and is ready for a new tenant. The other two have longstanding tenants who pay every month. Great price for the rent potential!

    Andrew Jarvis Lifstyl Real Estate

    130 E Broadway St, Winchester, KY 40391
  • /2

    $59,500

    • Land
    • 5 Acres
    • $11,900 per Acre

    4700 Four Mile Rd, Ford, KY 40391

    Nature lovers property. Four Mile Creek which runs into the Kentucky River is across the road. Nearby are restaurants, boat landings, kayak rentals, and historical sights.

    Garnett Davis Tom Goebel & Company

    4700 Four Mile Rd, Ford, KY 40391

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