Newest Homes for Sale in Winchester, KY

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  /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

  $79,950

  • 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

  $425,000

  • 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
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  /55

  $679,500 Open Sat 12:30PM - 2:30PM

  • 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

  $344,900

  • 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
• 

  

  /12

  $289,000

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

  55 Hillcrest Dr, Winchester, KY 40391

  **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 home offers excellent potential for the right buyer. The main level features three bedrooms, a full bath, a comfortable living room, and an

  Nina Vanetten RE/MAX Elite Lexington

  55 Hillcrest Dr, Winchester, KY 40391
• 

  

  /97

  $327,500

  • 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

  $329,000

  • 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
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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, and exceptional curb appeal and charm,

  

  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
• 

  

  /87

  $340,000

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

  215 Old Log Lick Rd, Winchester, KY 40391

  Seller will credit Buyer $1,000 for carpet repair/replacement. 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

  Kerry Ball Local First Realty, LLC

  215 Old Log Lick Rd, Winchester, KY 40391
• 

  

  /59

  $279,000

  • 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
• 

  

  /19

  $239,999

  • 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
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  /52

  $199,000

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

  334 S Burns Ave, Winchester, KY 40391

  Take a look at 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
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  /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
• 

  

  /34

  $899,000 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
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  /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

  $1,575,000

  • 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
• 

  

  /23

  $178,000

  • 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

  $165,000

  • 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

  $569,999

  • 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

  $259,900

  • 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
• 

  

  /60

  $279,950

  • 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? The sellers are

  Darrell Tackett Dream Maker Realty, LLC

  115 Watercrest Cir, Winchester, KY 40391

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