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 modern living. Known for its rich history and vibrant community, Winchester offers a delightful blend of small-town charm and contemporary conveniences. With its picturesque landscapes, friendly neighborhoods, and a strong sense of community, it's no wonder that many are choosing to call this lovely city home.

Winchester boasts a variety of amenities, including local parks, schools, and shopping centers, making it an ideal place for families, professionals, and retirees alike. The city's historic downtown area is a treasure trove of unique boutiques, cozy cafes, and delightful eateries, perfect for leisurely strolls or weekend outings. Outdoor enthusiasts will appreciate the nearby parks and recreational facilities, providing ample opportunities for hiking, fishing, and enjoying nature.

For those seeking affordable housing options, Winchester is a gem. With a range of homes available for under $350,000, you can find the perfect residence that fits your budget and lifestyle. Whether you're looking for a charming single-family home, a cozy cottage, or a modern townhouse, Winchester has something to suit every taste and preference. The real estate market here is thriving, offering a wonderful opportunity for first-time homebuyers and seasoned investors alike.

Come discover why Winchester, KY, is not just a place to live, but a place to thrive. With its welcoming community, beautiful surroundings, and affordable homes, you might just find your dream home in this enchanting city!

Newest Winchester Homes under $350,000

15 Maryland Ave, Winchester
$220,000
3 Beds ⋅ 1 Baths ⋅ 26027559 MLS
Charming, move in ready 3-bedroom home just minutes from downtown Winchester! This inviting home features LVP flooring throughout, beautiful granite countertops, and a practical layout that makes everyday living easy. With three bedrooms and a full bath, there's plenty of space to make it your own. Enjoy the convenience of being close to downtown Winchester, local dining, shopping, and everything the community has to offer. Come see all this place has to offer and discover your next place to call home!

15 Maryland Ave, Winchester
109 5th St, Winchester
$265,000
5 Beds ⋅ 4 Baths ⋅ 26027497 MLS
Welcome home to this spacious two-story residence offering plenty of room for family and guests. Featuring 5 bedrooms and 3 bathrooms, this home provides a comfortable and versatile layout with generous living space throughout. Beautiful wood floors add warmth and character, while the tile bathrooms offer durability and easy maintenance. Enjoy the charm of the front porch and inviting sunroom, perfect for relaxing or enjoying your morning coffee. The home also features new concrete patios in both the front and back, providing great outdoor spaces for entertaining, relaxing, or enjoying time with family. Conveniently located near Main Street, with easy access to local shops, restaurants, and amenities. A spacious home with character, comfort, and plenty of room to make it your own! Buyer to verify all aspects of the home, including exact square footage and schools!

109 5th St, Winchester
213 E Broadway St, Winchester
$200,000
3 Beds ⋅ 1 Baths ⋅ 26027397 MLS

213 E Broadway St, Winchester
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
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
$220,000
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
6 French Ave, Winchester
$296,000
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
115 Quail Ridge Rd, Winchester
$225,000
3 Beds ⋅ 3 Baths ⋅ 26025201 MLS
Looking for low-maintenance living without giving up space? This Winchester townhouse offers three bedrooms, 2.5 baths and a comfortable two-story layout with room to spread out. The main level features a spacious living room with a fireplace, dining area, kitchen and half bath. Just off the dining area, the back deck gives you a nice spot to relax or enjoy some time outside. Upstairs, the primary bedroom has its own private bath and large walk-in closet, along with two additional bedrooms, another full bath and laundry. There's also an attached garage and plenty of closet space throughout. A great option for anyone looking for an easy-to-maintain home with the space and storage you don't always find in a townhouse.

115 Quail Ridge Rd, Winchester
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