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Newest Homes for Sale in Winchester, KY

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  • /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, new insulation and baffling, and

    Agent Photo

    Tyler Hurst

    Oak & Acre

    (859) 927-8049

    128 Cherokee Dr, Winchester, KY 40391
  • /2

    $100,000

    $10K PRICE DROP
    • Land
    • 13,503 Sq Ft
    • $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

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

    $10K PRICE INCREASE
    • Land
    • 12,632 Sq Ft
    • $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

    $10K PRICE INCREASE
    • Land
    • 16,552 Sq Ft
    • $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

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

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

    $10K PRICE DROP
    • Land
    • 13,939 Sq Ft
    • $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
  • /2

    $110,000

    • Land
    • 25,700 Sq Ft
    • $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
  • /60

    $229,000

    $70K PRICE DROP
    • 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
  • /37

    $1,575,000

    $20K PRICE DROP
    • 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
  • /23

    $175,000

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,228 Sq Ft

    220 Jackson St, Winchester, KY 40391

    Welcome to 220 Jackson Street in Winchester, KY 40391 - a great opportunity to own a home full of character in a convenient location. Whether you're a first-time buyer, investor, or looking to downsize, this property offers both comfort and potential. Inside, you'll find a functional layout with inviting living spaces that make everyday living easy. The home provides a warm and welcoming feel,

    Hunter Miller GSP Homes

    220 Jackson St, Winchester, KY 40391
  • /16

    $160,000

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,097 Sq Ft

    220 E Washington St, Winchester, KY 40391

    Investors take note, tenant occupied home, 3 bedrooms, 1 bathroom, one level living! Flippers, downsizing, or First-time buyers get ready! Wood style floors, covered front porch, back yard with patio...Do not miss an opportunity to add to your rental portfolio investment, start your real estate adventure, or make this home your own! Home is occupied 24-hour notice is required to show.

    Whitney Ensor Ensor Real Estate, LLC

    220 E Washington St, Winchester, KY 40391
  • /39

    $559,999

    $70K PRICE DROP
    • 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
  • /21

    $249,900

    $20K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,610 Sq Ft

    120 Windsor Dr, Winchester, KY 40391

    Welcome home to this cozy brick charmer in the desirable Belair Subdivision of Winchester, KY! This inviting 4 bedroom, 1 bath home offers comfortable living with a warm electric fireplace perfect for relaxing evenings. The spacious layout provides flexibility for family, guests, or a home office. Step outside to a fully fenced backyard ideal for pets, play, or enjoying quiet mornings with your

    Team Farthing - Mitch Farthing Southern Legacy Realty

    120 Windsor Dr, Winchester, KY 40391
  • /90

    $269,900

    Open Sat 11AM - 1PM $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,112 Sq Ft

    115 Watercrest Cir, Winchester, KY 40391

    Stunning Home in One of the Area's Most Coveted Neighborhoods!Experience spacious living with 3 generous bedrooms and 2 full baths on the main level, designed for comfort and everyday convenience. The walkout basement offers even more space with a large bedroom and an additional full bath, ideal for guests, extended family, or a private retreat. What truly sets this home apart? This standout

    Darrell Tackett Dream Maker Realty, LLC

    115 Watercrest Cir, Winchester, KY 40391
  • /49

    $175,000

    • 2 Beds
    • 1.5 Baths
    • 1,202 Sq Ft

    1494 Amster Grove Rd, Winchester, KY 40391

    Welcome to this charming river front house. Step out your back door and you are immediately at the river. Open floor plan with a wood burning fireplace. Metal cabinets and epoxy floors on the first level are designed to survive in case of a flood. First floor bedroom with enough room for a King sized bed. Upstairs you will find another bedroom and a half bath. Sip your morning coffee on your back

    Libby VanMeter Marshall Lane Real Estate - Lexington

    1494 Amster Grove Rd, Winchester, KY 40391
  • /28

    $84,900

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,946 Sq Ft

    300 Aspen Ln, Winchester, KY 40391

    Welcome home to this well-maintained 3 bedroom, 2 bathroom double wide manufactured home in Treehaven, offering close to 2,000 square feet of comfortable living space...a rare find for buyers looking for room, functionality, and flexibility. Inside, you'll love the open-concept layout that connects the large living room, a large den, a large kitchen, and dining area, making it ideal for both

    Agent Photo

    Christa Joynt

    Keller Williams Commonwealth

    (859) 903-5711

    300 Aspen Ln, Winchester, KY 40391
  • /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
  • /29

    $70,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 750 Sq Ft

    113 Mimosa Dr, Winchester, KY 40391

    Discover the perfect balance between home ownership, affordability, and rural tranquility in this charming 3-bedroom two bath home. Conveniently located near shopping areas and interstates providing easy access to Lexington, Winchester and many central Kentucky cities. The interior features freshly updated flooring, offering a cohesive feel to living spaces. The true highlight of this property is

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    (859) 328-1402

    113 Mimosa Dr, Winchester, KY 40391
  • /32

    $325,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    4305 Old Boonesboro Rd, Winchester, KY 40391

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    (859) 549-3072

    4305 Old Boonesboro Rd, Winchester, KY 40391
  • /16

    $124,500

    $5K PRICE DROP
    • 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
  • /2

    $110,000

    • Land
    • 20,473 Sq Ft
    • $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
  • /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
  • /2

    $110,000

    • Land
    • 13,939 Sq Ft
    • $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
  • /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
  • /2

    $110,000

    • Land
    • 11,761 Sq Ft
    • $407,407 per Acre

    125 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

    125 Jacob Ct, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 13,939 Sq Ft
    • $343,750 per Acre

    115 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

    115 Jacob Ct, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 21,780 Sq Ft
    • $220,000 per Acre

    260 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

    260 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 29,620 Sq Ft
    • $147,059 per Acre

    100 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

    100 Duclair Dr, 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
  • /65

    $759,000

    $66K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,361 Sq Ft

    455 Davis Ln, Winchester, KY 40391

    Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of

    Dale Hatton Dream Maker Realty, LLC

    455 Davis Ln, Winchester, KY 40391
  • /5

    $365,900

    New Construction $4K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,558 Sq Ft

    204 Jett Dr, Winchester, KY 40391

    New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

    Mila Ensor Ensor Real Estate, LLC

    204 Jett Dr, Winchester, KY 40391
  • /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
  • /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
  • /5

    $29,000

    $4K PRICE DROP
    • Land
    • 20,037 Sq Ft
    • $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
  • /22

    $139,000

    $8K PRICE DROP
    • 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
  • /5

    $70,000

    • Land
    • 1.72 Acres
    • $40,698 per Acre

    12541 Ironworks Rd, Winchester, KY 40391

    Discover the perfect place to build your dream home in Eskippakithiki Overlooks. This beautiful 1.72 acre parcel offers ample space, peaceful surroundings, and stunning natural views. Enjoy the serenity of country living, this land provides an ideal canvas for a custom home or family getaway. Don't miss this opportunity to secure your own piece of paradise.

    Daniela Virguez National Real Estate

    12541 Ironworks Rd, Winchester, KY 40391
  • /6

    $49,500

    • Land
    • 42,688 Sq Ft
    • $50,510 per Acre

    204 Wigeon Ct, Winchester, KY 40391

    Choose your preferred builder to construct your dream home in Mallard Place. Located in a quiet cul-de-sac at the rear of the subdivision. Only a 20 minute drive to Hamburg/Lexington and only a 5 minute drive to the Winchester Bypass. Enjoy the serenity of living in a private setting AND the convenience of being close to schools, shopping and I-64 and I-75.

    Jim Woodrum RE/MAX Creative, Winchester

    204 Wigeon Ct, Winchester, KY 40391

Showing Results 161 - 200, Page 5 of 6

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