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Newest Homes for Sale in Winchester, KY

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  • /52

    $269,000

    $6K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,417 Sq Ft

    104 Jackson Ferry Rd, Winchester, KY 40391

    Located in Winchester, this 4-bedroom, 2-bath home offers approximately 2,417 square feet of living space with room to spread out both indoors and out. The home features a spacious living room with a fireplace, providing a comfortable central gathering area. Multiple bedrooms offer flexibility for guests, home office space, or changing household needs. Recent updates include a renovated kitchen

    Bob Sophiea eXp Realty, LLC

    104 Jackson Ferry Rd, Winchester, KY 40391
  • /12

    $129,999

    $30K PRICE DROP
    • 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
  • /13

    $130,000

    $20K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,254 Sq Ft

    208 4th St, Winchester, KY 40391

    Discover the potential of this spacious 0.27-acre residential home nestled in a neighborhood community on clear and level land located in a Cul-de-sac of Lincoln Park Subdivision. This Property features 2-bedrooms, 1-Bathroom, a large family room with a fireplace. There is also a large versatile barn on the property as well. This could be an investment opportunity as well, for ideal savvy

    Anita McDermott Keller Williams Bluegrass Realty

    208 4th St, 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
  • /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
  • /24

    $225,000

    • Land
    • 24 Acres
    • $9,375 per Acre

    3934 Trapp-Goffs Corner Rd, Winchester, KY 40391

    Wonderful 24 acre retreat with gentle sloping land, and a creek bed running thru part of the front portion of the lots (6.1 acre parcel & 18.4 acre parcel at the rear). Build your dream home or just use as recreational or farm land until you do. 1 1/2 miles to the first exit on the Mountain Parkway exit #10. 12 miles to I-64 at Winchester. See attached pictures & plat/overhead pictures.

    Travis Emnett Top Ten Realty

    3934 Trapp-Goffs Corner Rd, Winchester, KY 40391
  • /76

    $139,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,360 Sq Ft

    404 Mount Vernon Dr, Winchester, KY 40391

    Ready to Stop Renting? Your Opportunity Is Here Step into the comfort and freedom of homeownership with this spacious, well maintained 2-bedroom, 2-bath modular home — and yes, the lot is included. An attached room addition provides even more flexibility, easily adaptable into a third bedroom, home office, hobby room, or bonus space to suit your lifestyle. --- Interior Highlights • 2 full

    Darrell Tackett Dream Maker Realty, LLC

    404 Mount Vernon Dr, Winchester, 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
  • /5

    $575,000

    • Land
    • 1.71 Acres
    • $336,257 per Acre

    1025 Colby Rd, Winchester, KY 40391

    This 1.7+/- acre parcel represents an excellent opportunity for almost any commercial application. The property has 397 feet of frontage along busy Colby Road (9,170 AADT, 2015) near its intersection with the Winchester Bypass (23,200 AADT, 2011). Located in the main shopping corridor of Clark County, this property receives tons of exposure and traffic from the adjacent Walmart Super-center,

    Jo Gawthrop Keller Williams Bluegrass Realty

    1025 Colby Rd, Winchester, KY 40391
  • /34

    $245,000

    $30K PRICE DROP
    • Land
    • 6.08 Acres
    • $40,296 per Acre

    190 Privacy Ln, Winchester, KY 40391

    6.08 acres settled in Clark County with access from both Privacy Ln and Little Stoner Rd. This property boasts a 30x56 with 10 foot wall Kentucky Steel Truss building with concrete floors, gas and wood burning heat, full bath, and a car lift. Additionally, there is a barn with a 3 bay shed attached.

    Jason Joseph Keller Williams Commonwealth

    190 Privacy Ln, Winchester, KY 40391
  • /12

    $269,500

    $76K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,072 Sq Ft

    1128 Dale Dr, Winchester, KY 40391

    Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

    Brian Hatfield Coldwell Banker McMahan

    1128 Dale Dr, Winchester, KY 40391
  • /52

    $369,900

    New Construction
    • 3 - 6 Beds
    • 2 Baths
    • 1,770 Sq Ft

    Barbara Plan at Boone's Crossing, Winchester, KY 40391

    Experience the true essence of homecoming with the Barbara floor plan, a beautifully designed new construction home available through one of the most trusted home builders in Central Kentucky. Thoughtfully crafted for modern living, this plan blends timeless exterior charm with a warm, open interior designed for comfort, flexibility, and everyday functionality.Step onto the inviting covered front

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824253, Winchester, KY 40391
  • /72

    $406,900

    New Construction
    • 3 - 6 Beds
    • 2.5 - 5.5 Baths
    • 2,570 Sq Ft

    Jackie Plan at Boone's Crossing, Winchester, KY 40391

    Unleash your creativity with the Jackie floor plan, a flexible and thoughtfully designed new construction home that empowers you to shape your ideal living space. Built by one of the most trusted home builders in Central Kentucky, the Jackie is a standout choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space, versatility, and modern

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824254, Winchester, KY 40391
  • /45

    $429,900

    New Construction
    • 3 - 5 Beds
    • 2.5 - 4.5 Baths
    • 2,722 Sq Ft

    Eleanor Plan at Boone's Crossing, Winchester, KY 40391

    Experience elevated living with the Eleanor floor plan, a thoughtfully designed new construction home available through one of the most trusted home builders in Central Kentucky. Created for today’s buyers seeking flexibility, luxury, and energy efficiency, the Eleanor blends timeless design with modern functionality for families looking for new construction homes in Lexington KY and surrounding

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824255, Winchester, KY 40391
  • /85

    $397,900

    New Construction
    • 3 - 5 Beds
    • 2.5 - 4.5 Baths
    • 2,263 Sq Ft

    Abigail Plan at Boone's Crossing, Winchester, KY 40391

    Step into the award-winning Abigail floor plan, a standout choice for buyers searching for new construction homes in Lexington, KY and Central Kentucky. Designed with today’s lifestyle in mind, this home offers the perfect blend of flexible floor plans, energy efficiency, and modern comfort—everything you expect from a trusted home builder in Lexington, KY.From the moment you arrive, the Abigail

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824251, Winchester, KY 40391
  • /41

    $343,900

    New Construction
    • 3 - 5 Beds
    • 2 - 4 Baths
    • 1,424 Sq Ft

    Lucy Plan at Boone's Crossing, Winchester, KY 40391

    Experience the Lucy floor plan, a versatile and thoughtfully designed new construction home that gives every member of the family the space they need to live, work, and thrive. Built by one of the most trusted home builders in Central Kentucky, the Lucy is a top choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want flexibility, comfort, and

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824256, Winchester, KY 40391
  • /37

    $378,900

    New Construction
    • 3 - 5 Beds
    • 2.5 - 3.5 Baths
    • 2,098 Sq Ft

    Nancy Plan at Boone's Crossing, Winchester, KY 40391

    Experience the Nancy floor plan, a masterfully designed two-story new construction home that blends smart functionality with open-concept living. Built by one of the most trusted home builders in Central Kentucky, the Nancy is an ideal choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want style, flexibility, and efficient use of space.From the

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824252, Winchester, KY 40391
  • /28

    $363,900

    New Construction
    • 4 - 5 Beds
    • 2.5 - 3.5 Baths
    • 2,100 Sq Ft

    Elizabeth Plan at Boone's Crossing, Winchester, KY 40391

    Experience the Elizabeth floor plan, a beautifully crafted new construction home designed for families who value open-concept living, thoughtful organization, and flexible bedroom space. Offered by one of the most trusted home builders in Central Kentucky, the Elizabeth is a standout option for buyers searching for new construction homes in Lexington KY and surrounding communities.From the moment

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824250, Winchester, KY 40391
  • /46

    $347,900

    New Construction
    • 3 - 6 Beds
    • 2 - 4 Baths
    • 1,580 Sq Ft

    Martha Plan at Boone's Crossing, Winchester, KY 40391

    The Martha floor plan is your canvas for creating a home that perfectly fits your lifestyle, offering unmatched flexibility, thoughtful design, and timeless appeal. Built by one of the leading home builders in Central Kentucky, the Martha is an excellent choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space that adapts to how they

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824258, Winchester, KY 40391
  • /35

    $360,900

    New Construction
    • 3 - 4 Beds
    • 2.5 - 3.5 Baths
    • 1,828 Sq Ft

    Grace Plan at Boone's Crossing, Winchester, KY 40391

    Discover the Grace floor plan, a thoughtfully designed new construction home that blends open-concept living with private, comfortable bedroom spaces. Built by one of the leading home builders in Central Kentucky, the Grace is a perfect fit for buyers searching for new construction homes in Lexington KY and nearby communities who want flexibility, style, and energy efficiency.From the moment you

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824257, Winchester, KY 40391
  • /55

    $324,900

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,222 Sq Ft

    1291 Muddy Creek Rd, Winchester, KY 40391

    Rare opportunity with TWO lots!! This cozy ranch home, originally built in 1952, but was completely remodeled down to the studs in 2023 (per Seller), offering the charm of an established home with the feel of modern construction. The open concept floor plan features a spacious family room flowing seamlessly into the kitchen, perfect for every day, living and entertaining. The layout provides

    Terri McGraw FC Tucker Bluegrass

    1291 Muddy Creek Rd, Winchester, KY 40391
  • /31

    $479,000

    $26K PRICE DROP
    • 8 Beds
    • 4 Baths
    • 5,058 Sq Ft

    265 S Highland St, Winchester, KY 40391

    Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8

    J Corey Griffo RE/MAX Elite Lexington

    265 S Highland St, Winchester, KY 40391
  • /15

    $284,900

    $12K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,693 Sq Ft

    327 Newcastle Ln, Winchester, KY 40391

    PRICE REDUCTION!!! Perfect for investment or primary residence. 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

    Huong Dunn Bluegrass Property Exchange

    327 Newcastle Ln, Winchester, KY 40391
  • /63

    $460,000

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

    1911 Trapp-Goffs Corner Rd, Winchester, KY 40391

    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 functional layout and a partially finished basement that

    Cheri Shaffer Lifstyl Real Estate

    1911 Trapp-Goffs Corner 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
  • /49

    $345,000

    $15K PRICE DROP
    • 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
  • /58

    $74,950

    $15K PRICE DROP
    • 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

    $398,000

    $66K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft

    104 Colby Hills Dr, Winchester, KY 40391

    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
  • /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

    $344,900

    $20K PRICE DROP
    • 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
  • /12

    $279,000

    $26K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,214 Sq Ft

    55 Hillcrest Dr, Winchester, KY 40391

    Open house 05/10 2-*4 pm **Don't miss this exciting opportunity to pick out the new flooring for the basement and kitchen with a full price offer.****New roof (6 months old), one year old AC and heating unit, new large storage shed, and one year old wooden fence All of the expensive upgrades have been done. Come make this home your own. All-brick ranch with a full walk-out basement! This charming

    Nina Vanetten RE/MAX Elite Lexington

    55 Hillcrest Dr, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 16,552 Sq Ft
    • $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

    $10K PRICE DROP
    • Land
    • 16,117 Sq Ft
    • $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

    $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
  • /2

    $110,000

    $10K PRICE INCREASE
    • Land
    • 15,246 Sq Ft
    • $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

    $324,900

    $45K PRICE DROP
    • 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

    $10K PRICE DROP
    • Land
    • 13,939 Sq Ft
    • $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

    $10K PRICE DROP
    • Land
    • 13,939 Sq Ft
    • $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

    $10K PRICE DROP
    • Land
    • 13,939 Sq Ft
    • $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

Showing Results 121 - 160, Page 4 of 6

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