Winchester Homes under $350,000

Winchester Homes under $350,000

Welcome to Winchester, Kentucky – a charming city nestled in the heart of Clark County, where Southern hospitality meets small-town charm. Known for its rich history and vibrant community, Winchester offers a delightful blend of picturesque landscapes and modern conveniences. With its historic downtown, beautiful parks, and a variety of local shops and eateries, it's no wonder that Winchester is becoming a sought-after destination for homebuyers.

For those seeking affordable housing options, Winchester boasts an impressive selection of homes under $350,000. Whether you're a first-time buyer, a growing family, or looking to downsize, the city features diverse properties that cater to various lifestyles. From cozy single-family homes with spacious yards to charming bungalows with vintage character, there’s something for everyone.

The real estate market in Winchester is thriving, making it an ideal time to invest in this welcoming community. Residents enjoy easy access to local amenities, including schools, healthcare facilities, and recreational opportunities, all while being surrounded by the natural beauty of Kentucky's rolling hills.

Imagine sipping your morning coffee on a front porch overlooking tree-lined streets or hosting family gatherings in your backyard oasis. With homes under $350,000, you can turn that dream into reality. Explore the hidden gems of Winchester and discover the perfect property that fits your needs and budget.

Come experience the warmth of Winchester, where community spirit and affordability create the perfect backdrop for your next chapter. Your dream home awaits!

Newest Winchester Homes under $350,000

2550 Kiddville Rd, Winchester
$335,000
3 Beds ⋅ 2 Baths ⋅ 26027363 MLS
Country living without being far from where you need to be! Situated on approximately 4 beautiful, flat and usable acres, this property is just minutes from Mt. Sterling, approximately 12 minutes from downtown Winchester, and a short drive to Lexington—giving you the peace and space of the countryside while keeping shopping, dining and everyday conveniences within easy reach. Built in 2023, this beautiful manufactured home offers 1,860 sq. ft., 3 bedrooms and 2 full baths with a comfortable, welcoming layout. The cozy yet generously sized living room features a beautiful fireplace with built-in shelving, creating a warm and inviting space to relax, gather and feel right at home. The kitchen is a home chef's dream, offering an abundance of cabinetry, a large center island, farmhouse-style sink, stainless appliances and statement range hood, along with an adjoining dining area filled with natural light. A generously sized laundry/utility room adds even more functionality with a utility sink, additional cabinetry and pantry/storage space. The primary suite provides a relaxing retreat with a walk-in closet and private bath featuring a large walk-in tiled shower and separate soaking tub. Two additional nicely sized bedrooms provide comfortable, welcoming spaces for family or overnight guests, with a second full bath conveniently located nearby. Outside is where this property really sets itself apart. The enclosed garage/workshop provides valuable space for your side-by-side, lawn equipment, tools and more. If you've been dreaming of having your own workshop space at home, this one is ready for you. Attached to the garage is an expansive covered entertaining area, complete with a fireplace and bar-style island. From cookouts and game days to movie nights, birthday parties, gatherings or cozy evenings around the fire, there are so many ways to enjoy this space. The outdoor living continues with a covered front porch and screened-in porch, perfect for sitting back and taking in the peaceful scenery. And when warmer weather returns, the above-ground pool with its large surrounding deck is ready to enjoy. Four flat acres, plenty of room inside and out, and country living with town still close by this is a property you'll want to experience in person. Come take a look!

2550 Kiddville Rd, Winchester
8 Monroe Ave, Winchester
$299,900
3 Beds ⋅ 2 Baths ⋅ 26027106 MLS
Welcome to one of Winchester's best-kept secrets! This beautifully updated 3-bedroom home is truly move-in ready and packed with upgrades inside and out. From the moment you arrive, the beautifully landscaped yard sets the tone for what's waiting inside. Thoughtful updates throughout give the home a fresh, modern feel, while a new roof provides added peace of mind. Step outside and enjoy the large fenced backyard, offering plenty of room for entertaining, pets, play, or relaxing in your own private outdoor space. And it's the little extras that make this home stand out—even the bathroom features Bluetooth connectivity for an added touch of modern convenience! With upgrades around every corner and all the work already done, this is the kind of home you can simply move into and enjoy. Stylish, updated, and full of unexpected extras—this Winchester gem may not stay a secret for long!

8 Monroe Ave, Winchester
19 Victory Ave, Winchester
$285,000
3 Beds ⋅ 2 Baths ⋅ 26026938 MLS
Welcome home to 19 Victory Ave in Winchester's! This single-family residence offers 1,780 sq ft of flexible living space, featuring 3 bedrooms, 2 bathrooms, and handsome hardwood flooring. Enjoy cooking and entertaining with the included kitchen appliances, and take advantage of the detached garage and off-street parking. Situated on a spacious lot under half an acre, this property provides convenient access to local Winchester dining, shopping, and everything this city has to offer!

19 Victory Ave, Winchester
326 W Lexington Ave, Winchester
$225,000
3 Beds ⋅ 1 Baths ⋅ 26026771 MLS
ABSOLUTE AUCTION — SELLS TO THE HIGHEST BIDDER REGARDLESS OF PRICE! Offered at Live On-Site Absolute Auction with Simulcast Internet Bidding. Auction is on Thursday, October 15, 2026 at 6:00 PM (EST). Buyers premium will be added to the final bid price and non-refundable earnest money required. Property sells AS-IS, WHERE-IS with no contingencies. 3 Bedrooms, 1 Bathroom with separate dining room, standalone kitchen, and living room featuring a fireplace. Full unfinished basement with ample potential for storage or expansion. Investment Potential: Major DIY/fixer-upper opportunity—ideal for investors or buyers looking to customize and add value

326 W Lexington Ave, Winchester
14 Shelley Dr, Winchester
$215,000
3 Beds ⋅ 1 Baths ⋅ 26026596 MLS
This brick ranch offers three bedrooms, a full bath and luxury vinyl flooring throughout. The spacious living room opens into the kitchen, and the unfinished basement gives you plenty of extra room for storage with space to use however you need it. Sitting on a corner lot, this home is a great option for anyone looking for an affordable home with room to make it their own. Plus, you're close to shopping and restaurants and just a few minutes from I-64 for an easy commute.

14 Shelley Dr, Winchester
600 College St, Winchester
$225,000
3 Beds ⋅ 2 Baths ⋅ 26026485 MLS
Welcome to 600 College Street! Offering over 1,700 square feet, this versatile Winchester home features 3 bedrooms, 2 full bathrooms, plus an additional room ideal for a 4th bedroom, home office, or flex space. Inside, you'll find a spacious living room and a dining room with plenty of room to create additional living or entertaining space. The kitchen offers a walk-in pantry and conveniently located laundry area. An unfinished basement provides ample storage and walkout access, while the attached one-car garage adds everyday convenience. Outside, enjoy a covered front porch and a peaceful back porch surrounded by mature trees for added privacy. Conveniently located near Downtown Winchester, College Park, Legacy Grove, local shopping, dining, and everyday amenities, with easy access to I-64 for a straightforward commute toward Lexington. Improvements, including a roof replacement, LVP flooring, renovated kitchen and baths, and updated plumbing all done in 2024. Schedule your private showing today!

600 College St, Winchester
335 Newcastle Ln, Winchester
$304,900
3 Beds ⋅ 3 Baths ⋅ 26026107 MLS
Welcome to this well-maintained home located in a quiet, established neighborhood with convenient access to everything Winchester has to offer. The first floor features an open and inviting layout, creating a comfortable space for everyday living and entertaining alike. Upstairs, you'll find a traditional three-bedroom floor plan with generously sized bedrooms, including a spacious primary suite. Recent updates include a brand-new roof, along with manufactured hardwood flooring installed in the living area, foyer, and primary bedroom. Conveniently located near the Winchester Bypass, this home offers quick access to shopping, dining, and everyday amenities, while also providing easy access to I-64, I-75, Lexington, and the Mountain Parkway for commuters and travelers. Offering a desirable combination of space, updates, and location, this home is ready for its next owner to enjoy. Schedule your private showing today!

335 Newcastle Ln, Winchester
102 Quail Ridge Rd, Winchester
$243,500
3 Beds ⋅ 3 Baths ⋅ 26025942 MLS
This move-in ready townhome is located in Greenfield subdivision and sits on a quiet street with no through traffic. On the main level you will find 2 nicely sized bedrooms , 2 full baths, laundry closet along with a fully closed in sun-porch. The living room is spacious and the kitchen is equipped with top notch appliances. Below you will find the walkout basement where there is another bedroom, nice storage area with a half bath and a nice living or office area. Roof replaced this year, hot water heater replaced in 2025 and air replaced in 2023. Great location!! Close to schools, restaurants and shopping with I-64 only 2 miles away! Approximately 20 minutes from Hamburg. There is a very friendly cat that will be closed in the sun porch please don't let him out.

102 Quail Ridge Rd, Winchester
6590 Ironworks Rd, Winchester
$125,000
1 Beds ⋅ 1 Baths ⋅ 26025849 MLS
A truely country/rustic feel to this starter home on more than a 1/2 acre. Open concept main area with newer appliances and LVP flooring. Above ground pool and firepit allow for outdoor fun... complete with a shed for extra storage. A garden spot ready to go with several fruit trees, allow for another level of true country living. If you are looking for an affordable place to start or retire, this one could be for you!

6590 Ironworks Rd, Winchester
611 College St, Winchester
$199,900
2 Beds ⋅ 2 Baths ⋅ 26025674 MLS
This updated ranch is an easy walk to College Park and College Gym. You will love the huge backyard with a 2-car detached garage for storage or possibly a workshop plus extra storage in the storage building. No steps in the house! New flooring has recently been installed with fresh paint and updated lighting. Each bedroom is very spacious. The roof is only 3 years old. This cutie has a spacious open concept living area. The home checks all the boxes for the perfect first-time home buyer. It would also be perfect for someone wanting to downsize. 611 College St. is your reason to stop renting and start owning.

611 College St, Winchester
6 French Ave, Winchester
$319,900
4 Beds ⋅ 2 Baths ⋅ 26025571 MLS
SPACE, CHARACTER & LOCATION—THIS HOME HAS IT ALL! Step inside and discover a home filled with charm, character, and plenty of room to make your own. Featuring 4 generously sized bedrooms and 2 bathrooms, this home offers space for everyone to spread out. Beautiful original wood floors throughout the home add warmth and timeless character you just can't recreate. Enjoy the charm of the beautiful front porch, perfect for morning coffee or relaxing at the end of the day. Out back, the privacy-fenced yard provides a wonderful space for entertaining, pets, play, or simply enjoying the outdoors. Add in the convenience of a great location, and this home has so much to offer. Spacious rooms, original character, and a location you'll love—this is one you'll want to see in person!

6 French Ave, Winchester
118 College St, Winchester
$309,900
3 Beds ⋅ 2 Baths ⋅ 26025290 MLS
Beautifully updated Craftsman-style ranch offering over 2,000 square feet of comfortable living space in a desirable Winchester location. Walking distance to downtown, the library, College park gym and pool. This move-in-ready home blends timeless character with extensive modern updates, including a new roof, new 6" gutters, new HVAC system, new water heater, fresh interior paint, updated windows, lighting, switches, and outlets throughout. The renovated kitchen is the heart of the home, featuring granite countertops, a center island, and appliances replaced in 2025. Major improvements provide added peace of mind, including the plumbing drain lines replaced from the home to the road, bathroom walk-in shower and new toilets. Enjoy the convenience of a carport, off-street parking, and a welcoming covered front porch that enhances the home's Craftsman charm. The backyard offers a highly usable outdoor space perfect for entertaining, gardening, pets, or simply relaxing. With extensive updates already completed, this well-maintained home is ready for its next owner to enjoy.

118 College St, Winchester
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