Winchester, Kentucky listings for sale

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$285,000 - Winchester, KY
10 Upper Street Winchester, KY - Modern Ranch residence full un-finished basement, large lot.
1980 | 3 | 2 | 2,380 sqft.
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$285,000 - Winchester, KY
217 Morris Road Winchester, KY - NEW Price Reduction!!! This is The one You Have Been Waiting For! Room For The Whole Family In The Country But Within 5 Minutes Of The Interstate. This 4 Bedroom 2 Bathroom Home With A Living Room And Family Room/Den With Open Kitchen Has It All. Property Includes An Above Ground Swimming Pool, TinyHome/Shed That Has Plumbing Already Ran And Electric At The Pole Right There. This Would Be The Perfect ManCave/SheShed Or Mother In Law Quarters! The Area Has Beautiful Views and And A Nice Porch And Deck For Passing Time. In The Spring You Will Get A Beautiful Surprise When All The Plants And Trees Start To Bloom. Don't Let This One Pass You By. There Is An Opportunity To Buy More Land Too! Home is Under A 48 Hour Kickout Contingency.
2004 | 4 | 2 | 1,924 sqft.
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$277,000 - Winchester, KY
151 Hilltop Drive Winchester, KY - Lovely ranch on a basement home in a small rural neighborhood. This location is the perfect blend of rural living but very convenient to everything! Less than 1 mile from the eastern bypass that provides fast access to I-64, downtown Winchester, parks, and shopping. Large half acre lot with fenced in backyard and a chicken coop! Large deck on the back for entertaining or just relaxing while enjoying the peaceful country views. 4 bedrooms on the main level. The basement offers plenty of flexible space with rooms previously used as bedrooms, a den, and storage areas. Home is sold As-Is with inspections welcomed. Buyer to verify all information. Seller is willing to give a 3,000 dollar concession toward appliances.
1960 | 4 | 2 | 1,873 sqft.
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$275,950 - Winchester, KY
3614 Stamper Drive Winchester, KY - 'Fully renovated to perfection, this property features brand-new upgrades throughout. Highlights include newly installed windows, doors, and flooring, complemented by modern appliances and updated cabinetry. A new deck provides an ideal space for outdoor enjoyment, while contemporary fixtures add a touch of elegance. This home is truly a remarkable opportunity and an absolute must-see.'
1987 | 3 | 2 | 1,247 sqft.
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$275,000 - Winchester, KY
16 Taylor Avenue Winchester, KY - STOP scrolling and LOOK! This charming and pristine home is clean as a whistle and just a short walk to active and historic downtown Winchester. Sit on the covered front porch in the summertime shade or on the deck/patio overlooking the spacious/private backyard. Move-in ready with lots of space inside and out (over 2800 sq.ft. finished!), 4 large bedrooms, 2 full baths (one upstairs and one downstairs), HUGE kitchen with stainless appliances (and tons of cabinet space) and a formal dining room. HVAC system is less than two years old and the downstairs water heater is less than one year old. One of my favorite things about this home is out back! Multiple MAN CAVES!! A 20' x 30' detached garage and a fairly new metal 25 x 22' garage/shop. Great location! Convenient to shopping, downtown and Winchester Bypass and schools. Only 5 minutes to I-64, approximately 20 minutes to Hamburg/Lexington and 20 minutes to Mt. Sterling. Call and make an appointment to see this beautiful home today!
1947 | 4 | 2 | 2,808 sqft.
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$274,900 - Winchester, KY
528 Estes Drive Winchester, KY - Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden vegetables that will be ready for backyard entertaining. There is an oversized storage/tool shed, and a partially fenced back yard. The HVAC, water heater and Window World windows are less than 5 years old. Don't miss this one level home complete with an American Flag and Pole ready for the July 4th celebrating!
1960 | 3 | 2 | 1,904 sqft.
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$269,900 - Winchester, KY
400 Verna Drive Winchester, KY - Spacious Brick Ranch with Dual Master Suites & Investor Potential! This charming 5-bedroom, 3-bath brick ranch is nestled in a well-established neighborhood and offers a rare opportunity for customization and value-add. With some renovation projects already started, this home is ideal for an investor or handy homeowner ready to build instant equity. Enjoy the flexibility of two master suites, including a newer addition featuring a private entrance, spacious living area, luxurious walk-in tiled shower, and plumbing for a potential kitchenette or bar—perfect for guests, in-laws, or even short-term rental potential. Key features include: Large covered front porch Massive laundry/utility room RV hookup and gray water port on-site Subdivision with its own water treatment plant Great floor plan offering 5 bedrooms and 3 full bathrooms Mostly cosmetic updates remain—paint, fixtures, and finishing touches—making this the perfect canvas for your vision. Whether you're looking to invest, flip, or make it your dream home, this property delivers the space and potential you've been searching for.
1980 | 5 | 3 | 2,617 sqft.
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$265,000 - Winchester, KY
40 North Burns Avenue Winchester, KY - This stunning fully remodeled 3-bedroom, 2-bathroom home is move-in ready with top-to-bottom updates. Every detail has been thoughtfully upgraded, from the modern lighting in every room to the brand-new flooring and fresh paint throughout. The kitchen is a standout with granite countertops, new cabinetry, and brand-new appliances, while the bathrooms boast quartz countertops and elegant tiled showers. A new roof and HVAC system offer energy efficiency and long-term peace of mind, and the all-electric setup—including the water heater—keeps utility costs low. Ideally located just a few blocks from downtown and shopping, this home offers both style and convenience. Don't wait—schedule a private tour today! --
? | 3 | 2 | 1,256 sqft.
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$259,900 - Winchester, KY
302 April Way Winchester, KY - This 3-bedroom, 2 full bath home is quietly located just off the Winchester Bypass. While convenient location may be obvious, updates can be seen throughout. Including stainless appliances, LVP flooring, new roof less than 1 year. With spacious yard, family room and sizeable master on-suite, this home may be what you have been waiting for. Schedule your showing today!
2002 | 3 | 2 | 1,321 sqft.
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$259,000 - Winchester, KY
363 South Main Street Winchester, KY - Welcome to 363 South Main Street in the heart of Winchester, Kentucky! This charming 3-bedroom, 2-bath home offers the perfect blend of timeless character and modern convenience. Built in 1940, the home exudes classic appeal with thoughtful updates that meet today's lifestyle. With 2,142 square feet of living space, there's plenty of room for a growing family to spread out and feel right at home. You'll love the inviting layout, featuring a cozy loft area ideal for relaxing with a good book or creating a quiet retreat. Located just minutes from local schools, shops, and restaurants, this home provides unbeatable convenience in a welcoming community. Don't miss your chance to tour this beautifully maintained gem—schedule your showing today and see why 363 South Main Street could be your perfect next home!
1940 | 3 | 2 | 2,142 sqft.