23

Winchester, KY Homes for Sale under $400,000

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  • /47

    $372,900

    • 4 Beds
    • 3 Baths
    • 2,105 Sq Ft

    114 Mallard Ln, Winchester, KY 40391

    Nestled in a quiet cul-de-sac just minutes from shopping, dining, and the interstate, this unique ranch-style home offers a space, flexibility, and convenience. Originally designed as a duplex, the property has been thoughtfully renovated and modernized for an easy lifestyle. The main living area welcomes you with a light-filled, open concept layout featuring beautiful hardwood floors, a

    Agent Photo

    Robin Jones

    Keller Williams Legacy Group

    (859) 809-3100

    114 Mallard Ln, Winchester, KY 40391
  • /36

    $319,900

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

    128 Cherokee Dr, Winchester, KY 40391

    **Open House Sunday 11/16 1-3PM** 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, and exceptional curb appeal and charm, this home is just waiting

    Agent Photo

    Tyler Hurst

    Thwaites Realtors LLC

    (859) 681-9697

    128 Cherokee Dr, Winchester, KY 40391
  • /24

    $369,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,635 Sq Ft

    206 Jett Dr, Winchester, KY 40391

    New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

    Mila Ensor Ensor Real Estate, LLC

    206 Jett Dr, Winchester, KY 40391
  • /33

    $365,000

    • 5 Beds
    • 2 Baths
    • 1,952 Sq Ft

    1270 Sewell Shop Rd, Winchester, KY 40391

    Country Living with Convenience — 5 Fenced Acres in Winchester, KY Enjoy the perfect blend of peaceful country living and easy access to town with this well-maintained home on 5 fully fenced acres in Winchester, KY. Conveniently located just 30 minutes to Lexington, 5 miles to I-64, 10 minutes to Mt. Sterling, and 15 minutes to Winchester, this property offers country living without sacrificing

    Meggan Batey Keller Williams Legacy Group

    1270 Sewell Shop Rd, Winchester, KY 40391
  • /3

    $380,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    230 Evergreen Dr, Winchester, KY 40391

    Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

    Rex Hall United Real Estate Bluegrass

    230 Evergreen Dr, Winchester, KY 40391
  • /36

    $379,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    133 Shala-Mar Rue, Winchester, KY 40391

    Welcome to your next home in one of Clark County's most desirable neighborhoods—Shala Mar Estates! This beautifully updated 3-bedroom, 2-bathroom home offers the perfect blend of comfort, space, and modern convenience. Step into the expansive primary bedroom, a true retreat, complete with a stunning ensuite bathroom featuring a brand-new soaking tub and a separate tiled shower. The additional

    Nena Honaker Tom Goebel & Company

    133 Shala-Mar Rue, Winchester, KY 40391
  • /38

    $389,900

    • 4 Beds
    • 2 Baths
    • 2,659 Sq Ft

    6239 Old Boonesboro Rd, Winchester, KY 40391

    Welcome Home to the beautiful country! If you've been looking for quiet, space, and a place that truly feels like home, this charming Cape Cod on nearly 2 acres in Clark County checks all the boxes. Tucked into a peaceful rural setting yet conveniently located near I-75, I-64 and the Winchester Bypass, this property offers the best of country living with easy access to town. With over 2,600

    Kenya Woods United Real Estate Bluegrass

    6239 Old Boonesboro Rd, Winchester, KY 40391
  • /2

    $369,900 New Construction

    • 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
  • /25

    $310,000

    • 2 Beds
    • 1 Bath
    • 1,170 Sq Ft

    398 Pine Ridge Rd, Winchester, KY 40391

    Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment you walk in. Enjoy the outdoors from the

    Amie Hieneman ERA Select Real Estate

    398 Pine Ridge Rd, Winchester, KY 40391
  • /31

    $379,717

    • 3 Beds
    • 2.5 Baths
    • 2,636 Sq Ft

    300 Calmes Blvd, Winchester, KY 40391

    Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates . Welcome to your dream home in the highly sought-after Calmes Estates neighborhood! This beautifully maintained 3-bedroom, 2.5-bath residence offers generous living space and a layout perfect for families or entertaining guests. Highlights: *Expansive open-concept living areas *three spacious bedrooms with ample closet space *Two and a half

    Darrell Tackett Dream Maker Realty, LLC

    300 Calmes Blvd, Winchester, KY 40391
  • /23

    $343,900

    • 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

    $345,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    215 Evergreen Dr, Winchester, KY 40391

    Welcome to Triple Crown - a stunning proposed construction home nestled in the beautiful Locust Hill Acres community. Thoughtfully designed with an open-concept layout, this home offers 3 comfortable bedrooms, 2 full bathrooms, and versatile living spaces perfect for today's lifestyle.The expansive primary suite serves as a private sanctuary, complete with a spacious walk-in closet and a

    Rex Hall United Real Estate Bluegrass

    215 Evergreen Dr, Winchester, KY 40391
  • /42

    $349,900

    • 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. 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 laminate floors and a brick fireplace; the perfect place to

    Josh Wood Freedom Realty & Property Management

    3622 Stamper Dr, Winchester, KY 40391
  • /29

    $399,900

    • 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
  • /3

    $380,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    200 Evergreen Dr, Winchester, KY 40391

    Introducing the Run For The Roses - Proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms. The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite bathroom. The kitchen

    Rex Hall United Real Estate Bluegrass

    200 Evergreen Dr, Winchester, KY 40391
  • /12

    $355,000

    • 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.

    Brian Hatfield Coldwell Banker McMahan

    1128 Dale Dr, Winchester, KY 40391
  • /32

    $359,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,628 Sq Ft

    538 S Maple St, Winchester, KY 40391

    24 hour kickout in place. Be the first to call this stunning new construction home! Perfectly situated in the heart of Winchester, this two-story residence offers a fresh, modern feel with convenience at your doorstep. Step inside to discover a bright and airy open-concept main level, featuring durable and stylish Luxury Vinyl Plank (LVP) flooring throughout. The kitchen is a true showstopper,

    Heather Kuykendoll Bluegrass Properties Group

    538 S Maple St, Winchester, KY 40391
  • /70

    $335,000

    • 6 Beds
    • 4 Baths
    • 3,544 Sq Ft

    297 S Main St, Winchester, KY 40391

    Completely remodeled duplex offering over 3,400 sq. ft. of living space! Featuring 6 bedrooms and 4 bathrooms, this property has been fully updated with granite countertops, new appliances, fresh flooring, and paint throughout. The layout is bright and inviting with plenty of natural light. Enjoy the covered front porch, separate utility room, and unfinished basement for extra storage or future

    Silvia Torres Tru Life Real Estate

    297 S Main St, Winchester, KY 40391
  • /3

    $345,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    225 Evergreen Dr, Winchester, KY 40391

    Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

    Rex Hall United Real Estate Bluegrass

    225 Evergreen Dr, Winchester, KY 40391
  • /38

    $384,900 New Construction

    • 4 Beds
    • 4.5 Baths

    3600 Crowe Ridge Rd, Winchester, KY 40391

    Newly constructed unfinished multigenerational home located on 4 acres. Separate level living with 2 kitchens, 2 laundry rooms, and an en-suite for every bedroom. The main floor features 20' cathedral ceilings, 8' doors and 15 3'x6' windows creating a spacious home boasting panoramic views. Includes an additional 20'x24' loft space and 2 flex rooms with ANSI standard windows. Secondary living

    Maggie Napier Napier Realtors

    3600 Crowe Ridge Rd, Winchester, KY 40391
  • /13

    $400,000

    • Land
    • 2.19 Acres
    • $182,648 per Acre

    145 Codella Dr, Winchester, KY 40391

    Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

    Greg Leveridge Block + Lot Real Estate

    145 Codella Dr, Winchester, KY 40391
  • /6

    $388,000

    • 5 Beds
    • 3 Baths
    • 2,762 Sq Ft

    101 E Lexington Ave, Winchester, KY 40391

    Here's your chance to own a nice investment property. This triplex has a 2 bed 1 bath unit, 2 bed 1 bath unit, and a 1 bed 1 bath unit. 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

    101 E Lexington Ave, Winchester, KY 40391
  • /34

    $315,000

    • 2 Beds
    • 1 Bath
    • 1,531 Sq Ft

    1508 Ford Hampton Rd, Winchester, KY 40391

    Welcome home to this adorable 2 bedroom, 1 bathroom farmhouse on 5 peaceful acres. Inside, the layout is open and inviting with LVP and hardwood flooring throughout with a tiled bath. The kitchen and family room flow together and feature beautiful exposed wood beams that are hundreds of years old and reclaimed from an old church. A wood-burning stove in the family room adds warmth and character

    Michelle Blackburn RE/MAX Creative, Winchester

    1508 Ford Hampton Rd, Winchester, KY 40391

Home Trends in Winchester, KY

Housing Trends

Median Sale Price
$249,950
Median Single Family Sale Price
$259,900
Median Townhouse Sale Price
$194,000
Average Price Per Sq Ft
$161
Number of Homes for Sale
83
Last 12 months Home Sales
328
Months of Supply
3.00
Median List Price
$264,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
5%
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