Winchester Kentucky homes for sale starting at Fifty Thousand Dollars

$430,000 - Winchester, KY

265 Evergreen Drive Winchester, KY - Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, walkout unfinished basement and thoughtful living spaces throughout. The spacious primary suite features a large walk-in closet and a private ensuite bath, providing a relaxing retreat at the end of the day. You'll love the kitchen's layout with a convenient pantry just steps away, as well as a separate utility room for added convenience. The bonus room or dedicated home office adds flexibility to fit your lifestyle needs. Enjoy morning coffee or evening sunsets from the large covered front and rear porches, and take advantage of the attached 2-car garage for extra storage. Set on a generous one-acre lot in a peaceful, rural setting, The Mulberry offers the charm of country living with the comfort of a well-crafted modern home. Don't miss your opportunity to build your dream home in Locust Hill Acres!

$427,900 - Winchester, KY

4732 Old Boonesboro Road Winchester, KY - NEW PRICE REDUCTION!!! This Is The One You Have Been Waiting For!!! This Completely Remodeled 4 Bedroom 3 Bathroom Home On An Unfinished Basement Has It All. Features Include An Open Floor Plan; Dining Room With Fireplace; Big Kitchen With Lots Of Cabinets; Granite Tops; Stainless Steel Appliances; Range Hood; Farmhouse Sink; Huge Laundry Room Off Kitchen/Master Bedroom; First Floor Master Bedroom With Fireplace And Master Suite With Soaker Tub And Full Tile Shower; Large Bedrooms; Lots Of Space And Loads Of Storage; Garage; Man-Cave/She-Shed; Absolutely Beautiful Lot And Diamond Location.

$425,000 - Winchester, KY

210 College Street Winchester, KY - HISTORIC PRESERVATION AWARD! This stately brick residence, was among the winners of the 2024 Historic Preservation Award by the Clark County-Winchester Heritage Board and the Winchester Historic Preservation Board. Great attention was given to preserving/replicating original features of the home while bringing it to modern day living. Features of this gorgeous home include original heart pine flooring, custom kitchen, 2 primary bedrooms (on 1 & 2 flrs), original curved staircase, 5 fireplaces (gas logs only), original pocket doors and coffered ceilings. The interior design allows for an in-law suite on the first floor for multi-generational living. Alley access directly across from College Park Gym. Owner/agent

$419,900 - Winchester, KY

136 College Street Winchester, KY - OPEN HOUSE This Sunday, May 25 From 1:00 PM - 3:00PM!! Attention To Detail!!! FOR SALE OR RENT Starting June 1, 2025! Tastefully Renovated 4 Bedroom 4 1/2 Bath Home On College Street! Each Bedroom Has Its Own Private Bathroom! This Home Has Not Only Been Completely Renovated But An Addition Added To Modernize The Layout And Give You A First Floor Master Suite. The Uniqueness Of This Home Has Been Captured Through The Wooden Staircase and Details Throughout. If You Are Looking For A Large And Open Living And Kitchen Layout This Is It! A Quaint Office/Storage Room/Bourbon Bar With Windows On First Floor Gives You Even More Flexibility! New Updates Include All New Electrical; Plumbing; Roof; Doors; Windows; High End Fixtures; Flooring; TrimWork; Doors; Paint; Porch; Concrete Drive And Sidewalk; Privacy Fencing; New Kitchen With Shaker Cabinets; Granite; Tile Backsplash; Undermount Sink; Upgraded New Stainless Steel Appliances And So Much More!!! Call Today For Your Private Showing!

$401,000 - Winchester, KY

520 Bailey Lane Winchester, KY - Beautiful large ranch completely remodeled manufactured home on 24 acres with large addition. large bedrooms, family room, dining room, formal living room, 4 Bedroom and 3 baths. 30 foot above ground pool multiple outbuildings, front porch large back patio and just minutes from downtown Winchester. All new Bathrooms, All new Kitchen, All new fixtures, All new flooring. All new paint. House is situated on a quiet dead end lane. 24 acres to use how you see fit. Pasture, hunting, off grid, just depends on what your are looking for. Fireplace is decorative only. Will need cash buyer or local bank with 'in house' loan. Because of lost HUD Tags can not finance with VA, Conv, or FHA) In house only! Seller is a licensed real estate agent in the state of Kentucky. under a 48 hour Kick Out contingency

$400,000 - Winchester, KY

1094 Ford Hampton Road Winchester, KY - Introducing 1094 Ford Hampton Road, a Nice, Updated Farmhouse On 5.015 Acres of Gently Rolling Hills. This Lovely Home Features an Updated Kitchen with Ample Counter and Cabinet Space with a Large Farm Sink and Quartz Countertops, a See-Through Gas Fireplace Between the Dining Area and Den, a 1st Floor Primary Bedroom/Bathroom, Plus a 1st Floor Laundry/Full Bathroom. Upstairs There is 2 Bedrooms. Outside, There is a 2-Stall Barn, Storage Shed and 1-Car Detached Garage. New Roof Installed April 2025 and New Gravel Driveway Installed Allowing Parking for RV, Boat, Extra Vehicles and/or ATV's. Check out the Photos Showing the Abundance of Wildlife On the Property. Accepted Offer with 48 Hour Kick-Out.

$399,900 - Winchester, KY

101 Dorset Lane Winchester, KY - ***Click on the Virtual Tour section to see the video walk through!*** Welcome to your perfect home retreat! This beautifully updated ranch home features a 2-car garage, spacious open layout, and large bedrooms. The backyard is a showstopper — relax under the covered patio or take a dip in the heated in-ground pool, newly installed in 2022 and surrounded by a sleek concrete patio. Inside, enjoy modern upgrades like granite kitchen countertops, resurfaced and painted cabinets, a new sink with a built-in bottle washer, and a whole-house paint refresh in 2022. Extras include a built-in camera system, surround sound TV setup, and unbeatable proximity to shopping and dining.

$394,900 - Winchester, KY

$384,700 - Winchester, KY

309 Gallahadion Court Winchester, KY - This beautiful home located in desirable Fairholme Estates is a must see!! Amazing open floor plan with kitchen granite countertops, a large island and upgraded Frigidaire Elite Stainless Appliances. The waterproof Pergo laminate flooring is throughout the home. Don't miss the primary bedrooms with walk in closet, double sinks and tile shower in the bathroom. The two car garage is located on the same level with plenty of on and off street parking. **Seller will pay up to $4000 toward buyers closing costs at closing, with an acceptable contract. (Must be written on final contract)**

$380,000 - Winchester, KY

200 Evergreen Drive Winchester, KY - 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 includes a convenient pantry and flows seamlessly into the living and dining areas, ideal for entertaining or everyday comfort. A separate utility room adds extra functionality, and the 2-car garage provides ample storage. Enjoy the outdoors from the inviting front porch or take advantage of the unfinished walkout basement, offering endless possibilities for future expansion. Located on a beautiful one-acre lot in a peaceful rural setting, this home blends comfort, style, and space — the perfect place to plant roots. Don't miss your chance to make it yours!

Winchester, Kentucky listings for sale

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