Winchester, KY Homes for Sale under $500,000

Rare find! Gorgeous 25 acres of gently rolling land with a barn and creek is perfect for building your dream home and creating your homestead! Don't miss this opportunity! This is farm is conveniently located 20 miles from Hamburg and 5 miles from the Winchester bypass. No city sewage. Deed restrictions apply. Relax and enjoy the spectacular views. Get ready to enjoy life! Land consists of 2

Lura Justice Rector Hayden Realtors

Welcome to Fairholme Estates—where luxury meets comfort! This brand-new ranch-style home offers 4 bedrooms, 3 full baths, and 9' ceilings throughout for a spacious, airy feel. The designer kitchen features a huge island, beautiful finishes, and flows seamlessly into the vaulted great room filled with natural light from large windows. A Jack and Jill bath with separate sinks provides convenience,

Kristin Ray Lifstyl Real Estate

Unique opportunity to own a ranch with partly finished basement in a well established neighborhood! Stoneybrook subdivision is very convenient to schools, shopping, and dining. Ranch has been updated (including roof and windows) and in very good condition with lots of space. Three bedrooms, two baths, large spacious kitchen, extensive bar, huge pantry, laundry, dining, and great room are on the

Sam Watkins COLOR Real Estate

(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

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

Some homes are just houses—but this one was built for connection, creativity, and meaningful moments. Located in the desirable Oak Hill neighborhood, just minutes from GRC High School, this meticulously maintained 4-bedroom, 2.5-bath home offers the space and flexibility today's families are looking for. Formerly home to the beloved "2 Momma's Cooking for You," the property features a fully

Craig Bridgewater Bridgewater Real Estate

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

Entertaining the idea of entertaining family and friends? Looking for space for living the good life in a fun house in a great neighborhood? Then look no further. This house is ready for you to make it your new home. Located in the desirable neighborhood of Earlymeade, this house is minutes from the Winchester Bypass, I- 64 corridor and the Hamburg area of Lexington. Along with 5 bedrooms and 3.5

Craig Bridgewater Bridgewater Real Estate

PRICE IMPROVEMENT PLUS SELLERS ARE OFFERING UP TO $7,500 TOWARD BUYERS CLOSING COSTS, PREPAIDS OR RATE BUYDOWN. Welcome to an extraordinary residence where luxury, craftsmanship, and natural beauty come together. This house has been taken down to the studs, and thoughtfully rebuilt. This two story home with a walk-out basement sits on 8 acres, adjoining the Lower Howard Creek Preserve, offering

Lucy Martin Jenkins United Real Estate Bluegrass

Prime land located on the outskirts of Winchester ready for possible development. Parcel has frontage on both East Broadway and Washington Street. Land is currently zoned A-1. Utilities available. The future awaits!!!

Keith Wilson Coldwell Banker McMahan

Do you ever wonder what it would be like to live in the days of "Gone with the Wind"? Well, here is your chance to own your own personal "Tara". Spacious country home with acreage suitable for children, pets, and livestock. This home is perfect for escaping city life and crowds. Home consists of 5 bedrooms, 3 full bathrooms, Living Room, Dining Room, large Kitchen, room for an office or craft

Keith Wilson Coldwell Banker McMahan

Located in the Mallard Place subdivision, this ranch home offers 3 bedrooms, 2 full baths, and 1 half bath with approximately 2,652 square feet of finished living space. The home features new flooring in the main living area and a functional single-level layout. The kitchen includes an eat-in area, breakfast bar, double oven, cooktop, microwave, dishwasher, and refrigerator, with laundry

Laura Eaves Berkshire Hathaway de Movellan Properties