184

Winchester, KY Homes for Sale

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  • /86

    $530,000

    • 4 Beds
    • 3.5 Baths
    • 3,848 Sq Ft

    125 Casa Landa Way, Winchester, KY 40391

    Stoney Brook Subdivision! Second time ever offered for sale. Beautiful two story brick home with first and second floor en-suites. Each of the 4 bedrooms has its own walk in closet. Formal family room and dinning rooms, great room with fireplace, breakfast area, all season room with natural lighting, and large flex space located on second floor. All of this setting on .40 of an acre lot with side

    Maggie Napier Napier Realtors

    125 Casa Landa Way, Winchester, KY 40391
  • /27

    $269,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    916 Stratton Ln, Winchester, KY 40391

    Welcome to 916 Stratton Lane, a beautifully updated 3 bedroom, 2 bath home offering 1,400 square feet of comfortable living space in the highly desired Westmeade area. This charming brick home features a warm and inviting interior with stylish updates throughout. The spacious living room showcases rich dark flooring, a stunning stone fireplace, and abundant natural light, creating the perfect

    Joshua Davis The Agency

    916 Stratton Ln, Winchester, KY 40391
  • /39

    $579,900

    • 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

    $550,000

    • Land
    • 1.53 Acres
    • $359,477 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
  • /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
  • /63

    $1,149,000

    • 3 Beds
    • 3.5 Baths
    • 3,672 Sq Ft

    2100 Irvine Rd Unit 40391, Winchester, KY 40391

    Seller will need 48 Hours to show, This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths,

    Mila Ensor Ensor Real Estate, LLC

    2100 Irvine Rd Unit 40391, Winchester, KY 40391
  • /47

    $452,500

    • 3 Beds
    • 2.5 Baths
    • 2,961 Sq Ft

    42 Mockingbird Valley Rd, Winchester, KY 40391

    This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons

    Markus Cross McCallie Real Estate

    42 Mockingbird Valley Rd, 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
  • /22

    $221,500

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft

    443 Jameson Way, Winchester, KY 40391

    This move in ready ranch home offering 4 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

    443 Jameson Way, Winchester, KY 40391
  • /29

    $234,900

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    11 Shelley Dr, Winchester, KY 40391

    SELLER is motivated to offers! Welcoming you to this lovely updated throughout 3 bedroom, 2 full bath ranch! As you step into the home with its cozy feeling, and spacious space in every room, including a full unfinished basement wonderful for storage or to finish that into living square footage, great size back yard with large back patio perfect for the family gatherings, also a partial fenced in

    Nichole Bingham CENTURY 21 Advantage Realty

    11 Shelley Dr, Winchester, KY 40391
  • /27

    $198,000

    • 2 Beds
    • 1 Bath
    • 1,223 Sq Ft

    616 Boone Ave, Winchester, KY 40391

    Begin the New Year in your own home! It's a new beginning...Make an appoint to look at this two bedroom, one bath ranch. It has new paint and updated flooring. Range refrigerator and dishwasher are included, There is a nice size laundry room. The kitchen has lots of cabinets and there is an additional pantry in the hall. The dining room is off the kitchen and overlooks the living room. The rear

    Garnett Davis Tom Goebel & Company

    616 Boone Ave, Winchester, KY 40391
  • /23

    $270,000

    • 4 Beds
    • 2 Baths
    • 1,984 Sq Ft

    108 Ashley Dr, Winchester, KY 40391

    Be among the first to discover this exceptional property! This is a brand new listing, presenting a unique opportunity to own a home in a highly sought-after location. Imagine living in a neighborhood where everything you need is just a stone's throw away. This fabulous property boasts not only a full basement, offering endless possibilities for recreation, storage, or a home office, but also an

    A. Rebecca Woods Woods Realty Group

    108 Ashley 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
  • /23

    $180,000

    • 2 Beds
    • 1 Bath

    220 Jackson St, Winchester, KY 40391

    Welcome to 3769 Winthrop Drive in Lexington, KY 40514 - a fantastic opportunity to own a home in one of South Lexington's most convenient and sought-after areas. Tucked into an established neighborhood, this property offers the perfect combination of comfort, accessibility, and everyday functionality. Step inside to discover a welcoming layout designed for both relaxing and entertaining. The

    Hunter Miller GSP Homes

    220 Jackson St, Winchester, KY 40391
  • /14

    $129,300

    • Land
    • 2.3 Acres
    • $56,217 per Acre

    110 Knox Ct, Winchester, KY 40391

    The largest and most desirable lot in The Reserve is now available! Nestled in a cul-de-sac, this 2.3 acre tract offers exceptional views of Bluegrass farmland. Build your custom dream home and watch the sun set over the pond, right from your porch. Located in one of Winchester's newest luxury subdivisions, featuring carefully crafted guidelines to preserve the community's character. All of this

    Amanda Thomas The Agency

    110 Knox Ct, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.34 Acre
    • $323,529 per Acre

    230 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

    230 Duclair Dr, 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
  • /16

    $169,900

    • 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
  • /4

    $625,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,405 Sq Ft

    424 Alexis Way, Winchester, KY 40391

    Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard Cove neighborhood. This exquisite floor plan features a side-turned garage and captivating curb appeal with double front entry doors. Inside, you'll find a thoughtfully designed split-bedroom layout with a spacious primary suite that includes a luxurious ensuite with a walk-in closet, double vanity, tile

    Shane Underwood Keller Williams Commonwealth

    424 Alexis Way, 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
  • /44

    $850,000

    • Land
    • 83.71 Acres
    • $10,154 per Acre

    7075 Ecton Rd, Winchester, KY 40391

    ABSOLUTE AUCTION — SELLS TO THE HIGHEST BIDDER REGARDLESS OF PRICE! Offered at Live On-Site Absolute Auction with Simulcast Internet Bidding, this exceptional 83.714± acre Clark County farm will sell on Saturday, March 7, 2026 at 10:30 AM (EST) at 7075 Ecton Rd, Winchester, KY 40391. Tract One: 36.825Acres, Tract Two: 5.196 Acres, Tract Three: 5.022 Acres Tract Four: 36.671 Acres The property

    Jonathan Noel Noel Auctioneers and Real Estate Advisors

    7075 Ecton Rd, Winchester, KY 40391
  • /15

    $925,000

    • Land
    • 3.77 Acres
    • $245,358 per Acre

    300 Rolling Hills Ln, Winchester, KY 40391

    Great location just off exit 96 on I-64 and easy access to the Mountain Parkway. Only 15 minutes from I-75. Located near the entrance to the Winchester Kentucky Industrial Park. 3.774 flat acres to build your next business location.

    Josh Wood Freedom Realty & Property Management

    300 Rolling Hills Ln, Winchester, KY 40391
  • /58

    $525,000

    • 2 Beds
    • 1.5 Baths
    • 5,054 Sq Ft

    808 Bypass Rd, Winchester, KY 40391

    Unique Mixed-Use Opportunity! This versatile property offers prime potential for a restaurant, café, or retail space in a high-visibility location. The commercial space is turn key for a culinary venture or boutique business. Attached is a separate rental unit with private entrance, offering additional income or an ideal live/work setup. Additional space available for potential 2nd Apartment.

    Diana C Brooker Lifstyl Real Estate

    808 Bypass Rd, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.27 Acre
    • $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
  • /8

    $175,000

    • Land
    • 6.59 Acres
    • $26,555 per Acre

    990 Craig Crossing Rd, Winchester, KY 40391

    Lot # 13 contains 6.588 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

    990 Craig Crossing Rd, 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
  • /2

    $78,500

    • Land
    • 0.22 Acre
    • $356,818 per Acre

    Lot 5 Plantations Dr, Winchester, KY 40391

    NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

    Melia Hord Keller Williams Legacy Group

    Lot 5 Plantations Dr, Winchester, KY 40391
  • /12

    $269,900

    • 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
  • /29

    $389,900

    • 8 Beds
    • 8 Baths
    • 4,000 Sq Ft

    17 W Lexington Ave, Winchester, KY 40391

    Investment Opportunity in the Heart of Downtown Winchester! Discover 17 W. Lexington Ave, a converted commercial building now featuring 8 studio/one-bedroom apartments. Each unit includes a full kitchen and private bath, offering the perfect blend of comfort and convenience for tenants. This multifamily property is ideally situated in historic downtown Winchester, within walking distance to

    Joshua Lynch The Brokerage

    17 W Lexington Ave, Winchester, KY 40391
  • /6

    $49,500

    • Land
    • 0.98 Acre
    • $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
  • /34

    $260,000

    • Land
    • 6.08 Acres
    • $42,763 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
  • /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
  • /24

    $286,000

    • 12 Beds
    • 4 Baths
    • 4,010 Sq Ft

    149 Winn Ave, Winchester, KY 40391

    Welcome to this quad plex income producing property. It is a large lot and the property sits back on the lot away from the road. There are 4 units, each with 3 beds and 1 bath. The whole building has a total of bedrooms of 12 beds and 4 baths. Each unit has its own kitchen. The pictures are of the only vacant unit on the bottom left. The two lower units rent for $950 and $925. The upper units

    Libby VanMeter Marshall Lane Real Estate - Lexington

    149 Winn Ave, Winchester, KY 40391
  • /39

    $429,900 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,258 Sq Ft

    233 Cunningham Ln, Winchester, KY 40391

    Welcome to 233 Cunningham Lane in Winchester, KY — a versatile mini farm offering 6.7 acres, multiple outbuildings, and a functional one-level ranch floor plan designed for comfort and flexibility. Conveniently located less than two miles from the Mountain Parkway, this property combines rural space with easy accessibility for commuting and everyday travel. The ranch-style home features 3

    Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

    233 Cunningham Ln, Winchester, KY 40391
  • /28

    $89,900

    • 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, kitchen, and dining area, making it ideal for both everyday living and

    Christa Joynt Keller Williams Commonwealth

    300 Aspen Ln, 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
  • /18

    $99,000

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft

    114 Magnolia St, Winchester, KY 40391

    Great opportunity for investors, flippers, or anyone looking for a project with tons of potential! This 2 bedroom, 1 bath home features a 2 year old roof, giving you a solid head start on future updates. With its convenient location and plenty of possibilities, this property is ready for someone to bring their vision! Selling as is. Cash or conventional financing only.

    Michelle Blackburn RE/MAX Creative, Winchester

    114 Magnolia St, Winchester, KY 40391
  • /4

    $199,900

    • Land
    • 11.36 Acres
    • $17,597 per Acre

    2996 Irvine Rd, Winchester, KY 40391

    Are you looking to build your dream home in a quiet country setting with easy access to the Interstate? Look no further! This property offers it all! Gorgeous setting with the best views and creek access. This lovely farm is 11.36 acres of gently rolling country land, in a highly desirable area with easy access to interstate 64, the Mountain Parkway and Hamburg. No city sewage. Deed restrictions

    Lura Justice Rector Hayden Realtors

    2996 Irvine Rd, Winchester, KY 40391
  • /9

    $1,350,000

    • Land
    • 3.02 Acres
    • $447,020 per Acre

    155 April Way, Winchester, KY 40391

    Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided.Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One,

    Greg Leveridge Block + Lot Real Estate

    155 April Way, 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

Showing Results 81 - 120, Page 3 of 5

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