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Homes for Sale in 40391

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  • /49

    $355,000

    • 3 Beds
    • 2.5 Baths
    • 2,628 Sq Ft

    221 Moundale Ave, Winchester, KY 40391

    Step back in time as you walk up the stone steps into this beautiful 3 bed 2.5 bath house. This house has been very well maintained and offers many updates. You get the best of both worlds the craftsmanship of an older home with all the newer amenities. Hardwood, tile and brick floors throughout the house with Granite countertops, This house sits on a lot and a half. The owners have recently

    Andrew Fugitt Coldwell Banker McMahan

    221 Moundale Ave, Winchester, KY 40391
  • /24

    $209,900

    • 3 Beds
    • 2 Baths
    • 915 Sq Ft

    225 Buffalo Trace, Winchester, KY 40391

    This move in ready ranch home offering 3 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

    Tyler I Back The Brokerage

    225 Buffalo Trace, Winchester, KY 40391
  • /25

    $259,900

    • 3 Beds
    • 2 Baths
    • 1,530 Sq Ft

    1407 Ironworks Rd, Winchester, KY 40391

    Welcome to this beautifully remodeled 3 bedroom, 2 full bathroom home situated on a desirable corner lot. With 1,530 sq ft of living space, this home offers great combination of modern updates and comfortable living. Features Include 3 spacious bedrooms, 2 full bathrooms, Private master suite with ensuite bath, Fully remodeled interior, corner lot, Stainless appliances, full tiled showers and the

    Michael Hilario The Agency

    1407 Ironworks Rd, Winchester, KY 40391
  • /58

    $89,900

    • 2 Beds
    • 1 Bath
    • 825 Sq Ft

    1860 Ford Rd, Winchester, KY 40391

    Freshly cleaned and ready for its next owner, this property offers exceptional potential. The spacious 1,800 sq. ft. block garage provides a solid foundation for countless uses — from a workshop or storage facility to a future business or hobby space. An older trailer is also located on the property. It will require a full renovation or removal, giving you the freedom to redesign the space

    Darrell Tackett Dream Maker Realty, LLC

    1860 Ford Rd, Winchester, KY 40391
  • /17

    $429,000

    • 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
  • /55

    $679,500 Open Sat 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 3,431 Sq Ft

    7919 Mount Sterling Rd, Winchester, KY 40391

    Don't let this stunning, 3,431sqft home featuring 4 bed rooms and 3 full baths, sitting on 3 acres, slip through your hands! Custom built brick home nestled in a serene, park like setting overlooking Stoner Creek. Step into to the dramatic two story entryway welcoming you with custom cabinetry and detailed finishes throughout. One of the most captivating features is the sunroom, overlooking the

    Hannah Toole Coldwell Banker McMahan

    7919 Mount Sterling Rd, Winchester, KY 40391
  • /19

    $265,000

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

    130 E Broadway St, Winchester, KY 40391

    Turnkey downtown triplex with tenants already in place. An excellent addition to any investor's portfolio. Two units have been recently updated, while the third features a long-term tenant with future value-add potential. Property includes two 1BD/1BA units and one 2BD/1BA unit. Tenants pay all utilities directly except water, which is on a RUB system, keeping operating costs low. Strong income

    Sarah May Mayca Property Solutions

    130 E Broadway St, Winchester, KY 40391
  • /29

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,858 Sq Ft

    23 Windridge Dr, Winchester, KY 40391

    Welcome home!!! This beautifully updated all-brick ranch that perfectly blends charm and modern upgrades in a well established, desirable neighborhood is sure to please. Step inside to a bright open-concept living space featuring luxury vinyl flooring, a stunning wood-burning fireplace, and exposed wood ceiling beams that create a warm, inviting atmosphere in the spacious family room. The

    Holly Goeing The Agency

    23 Windridge Dr, Winchester, KY 40391
  • /18

    $260,000

    • 3 Beds
    • 1 Bath
    • 1,296 Sq Ft

    280 Pine Ridge Rd, Winchester, KY 40391

    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 expansion, this property is perfect for those dreaming of country living. Renovate the existing home or reimagine the space to fit your needs — the possibilities

    Derek Blankenship Keller Williams Commonwealth

    280 Pine Ridge Rd, Winchester, KY 40391
  • /33

    $209,900

    • 3 Beds
    • 1 Bath
    • 1,050 Sq Ft

    59 Holiday Rd, Winchester, KY 40391

    Don't Wait - this home is priced to Sell! All one level brick ranch features 3 Bedrooms, 1-bath. Newer updates include interior paint and laminate flooring giving the home a clean modern feel. The living spaces are filled with natural light, making the home feel warm and inviting. Step out to a spacious deck and large backyard - great for entertaining or just enjoying the outdoor space. Need

    Kathy Burton Coldwell Banker McMahan

    59 Holiday Rd, Winchester, KY 40391
  • /12

    $296,000

    • 5 Beds
    • 2 Baths
    • 2,214 Sq Ft

    55 Hillcrest Dr, Winchester, KY 40391

    All-brick ranch with a full walk-out basement! This charming home offers excellent potential for the right buyer. The main level features three bedrooms, a full bath, a comfortable living room, and an eat-in kitchen. The walk-out basement expands the living space with two additional bedrooms, full bath, family room with a kitchenette area, utility room, and ample storage with built-in shelving.

    Nina Vanetten RE/MAX Elite Lexington

    55 Hillcrest Dr, Winchester, KY 40391
  • /97

    $339,900

    • 3 Beds
    • 2.5 Baths
    • 1,794 Sq Ft

    322 S Burns Ave, Winchester, KY 40391

    This beautiful 1.5-story home offers all the charm of downtown in a small town, with a library, park, and restaurants nearby. Plus, just minutes to Lexington when the city is calling your name. This home has been remodeled for modern living, featuring an open floor plan. There is plenty of room for entertaining with a beautiful, well-equipped kitchen and a large island open to both the dining

    Nancy Hibbitts CENTURY 21 Advantage Realty

    322 S Burns Ave, 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
  • /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

    $100,000

    • 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
  • /2

    $110,000

    • Land
    • 0.35 Acre
    • $314,286 per Acre

    150 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

    150 Duclair Dr, Winchester, KY 40391
  • /23

    $329,900

    • 3 Beds
    • 2.5 Baths
    • 3,868 Sq Ft

    225 Plantations Dr, Winchester, KY 40391

    Welcome to 225 Plantations Drive, a beautifully maintained home in the desirable Royal Oaks Subdivision. This charming three-bedroom, two-and-a-half-bath residence is in wonderful condition and move-in ready! This is home comes with a wonderful floorplan that has a primary bedroom with built-in's on the first floor, Kitchen with granite and stainless appliances and deck has been updated with Trex

    John Wilson Bluegrass Properties Group

    225 Plantations Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    111 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

    111 Jacob Ct, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    169 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

    169 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    115 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

    115 Duclair Dr, Winchester, KY 40391
  • /36

    $319,900

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

    128 Cherokee Dr, Winchester, KY 40391

    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 including a brand new furnace installed in February of 2026, and exceptional curb appeal and charm,

    Agent Photo

    Tyler Hurst

    Thwaites Realtors LLC

    (859) 927-8049

    128 Cherokee Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.31 Acre
    • $322,581 per Acre

    215 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

    215 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    155 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

    155 Duclair Dr, Winchester, KY 40391
  • /2

    $110,000

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

    135 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

    135 Jacob Ct, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.29 Acre
    • $379,310 per Acre

    160 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

    160 Duclair Dr, Winchester, KY 40391
  • /2

    $110,000

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

    120 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

    120 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    141 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

    141 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    129 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

    129 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    165 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

    165 Duclair Dr, Winchester, KY 40391
  • /67

    $325,000

    • 3 Beds
    • 3 Baths
    • 2,821 Sq Ft

    3622 Stamper Dr, Winchester, KY 40391

    This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. With recently installed vinyl siding, gutters and gutter guard properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming

    Josh Wood Freedom Realty & Property Management

    3622 Stamper Dr, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.59 Acre
    • $186,441 per Acre

    255 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

    255 Duclair Dr, Winchester, KY 40391
  • /62

    $259,500

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

    3614 Stamper Dr, Winchester, KY 40391

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

    Darrell Tackett Dream Maker Realty, LLC

    3614 Stamper Dr, Winchester, KY 40391
  • /84

    $343,000

    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft

    215 Old Log Lick Rd, Winchester, KY 40391

    Enjoy where you live! Zen like grounds will bring inner peace in this 1,450 sq foot home on over 3 private acres. Covered front and back porches span the width of the house. Get off the grid with the solar panels on the roof (25 yr warranty), six raised garden beds, and fenced chicken coop! Average utility bill $50 in 2025 and $35 in 2024! (Solar panels paid for by Seller). No worries for fast

    Kerry Ball Local First Realty, LLC

    215 Old Log Lick Rd, Winchester, KY 40391
  • /59

    $294,000

    • 3 Beds
    • 1 Bath
    • 1,273 Sq Ft

    119 Tower Ln, Winchester, KY 40391

    A rare and refined retreat set on five unrestricted acres in Winchester. Privately positioned and surrounded by natural beauty, this renovated berm-style residence offers the perfect balance of seclusion and sophistication. Inside, you'll find thoughtfully curated updates including fresh designer paint, updated flooring, and a bright, inviting interior that feels both modern and timeless. The

    Shawna Wever Wever Realty LLC

    119 Tower Ln, Winchester, KY 40391
  • /18

    $243,000

    • 3 Beds
    • 2 Baths
    • 1,502 Sq Ft

    357 Silverton Way, Winchester, KY 40391

    This updated home offers easy access to I-64 and downtown Winchester. See ceiling fans in every room, upstairs bonus room, modern lighting in the kitchen and bath, and new appliances, countertops, and backsplash. Enjoy a peaceful, quiet neighborhood and a relaxing rural view from the backyard. A clean, comfortable, move-in-ready home with thoughtful upgrades throughout.

    Frank Mulder Tru Life Real Estate

    357 Silverton Way, Winchester, KY 40391
  • /52

    $209,000

    • 3 Beds
    • 1.5 Baths
    • 1,636 Sq Ft

    334 S Burns Ave, Winchester, KY 40391

    Check out the nice price adjustment on this one!!! Great opportunity to own this well loved home in a very convenient location in growing community of Winchester. Lots of character and charm upon entry into the entry foyer with nice staircase, opening to large living room with a lovely mantel. Spacious dining room with built in corner cabinet flows into kitchen with plenty of cabinetry and

    Jeanne Beaven Rector Hayden Realtors

    334 S Burns Ave, Winchester, KY 40391
  • /33

    $285,000

    • 3 Beds
    • 2 Baths
    • 1,790 Sq Ft

    211 Lindsey Ct, Winchester, KY 40391

    Nicely updated split-level home with a large, fenced backyard, located on a quiet cul-de-sac. This energy-efficient home boasts a brand-new HVAC system, a recently replaced roof, fresh paint and stylish new LVP flooring throughout the house. The large kitchen has updated countertops and cabinets, as well as brand-new stainless steel appliances with three-year warranties. Both bathrooms have been

    Lesley Ward Biederman Real Estate

    211 Lindsey Ct, Winchester, KY 40391
  • /61

    $925,000 New Construction

    • 5 Beds
    • 3.5 Baths
    • 2,842 Sq Ft

    1150 Craig Crossing, Winchester, KY 40391

    Stunning new construction offering 5 bedrooms, 3.5 bathrooms, sitting on roughly 2.5 serene acres. This home is surrounded by picturesque farmland and panoramic views. 4 bedrooms are located on the main level for ultimate convenience. Offering the perfect blend of space, style, and serenity. Features include open concept layout, spacious kitchen with kitchen island, granite counter tops, hidden

    Stephanie Hacker Kentucky Residential Real Estate, LLC

    1150 Craig Crossing, Winchester, KY 40391
  • /62

    $319,500

    • 8 Beds
    • 5 Baths
    • 3,637 Sq Ft

    144 Holly Ave, Winchester, KY 40391

    Excellent investment opportunity featuring two income-producing buildings on one lot, offered together as a package deal. This unique multifamily property includes a triplex and a separate duplex, making it ideal for investors looking to expand their portfolio with multiple units in one purchase. The triplex (Building A) consists of three units: Unit A-1: 2 bedrooms, 1 bathroom Unit A-2: 1

    Shane Underwood Keller Williams Commonwealth

    144 Holly Ave, 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

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