Winchester Homes under $400,000

Winchester Homes under $400,000

Welcome to Winchester, Kentucky, a charming city nestled in Clark County that beautifully blends small-town warmth with modern conveniences. Known for its rich history and vibrant community spirit, Winchester offers a delightful mix of scenic landscapes, local parks, and a bustling downtown area filled with unique shops and eateries.

As you stroll through the historic streets, you’ll encounter stunning architecture that reflects the city’s heritage, alongside contemporary developments that cater to today’s lifestyle. Winchester is not just a place to live; it’s a community where neighbors become friends and families thrive.

For those seeking an affordable yet charming place to call home, Winchester boasts an impressive selection of homes priced under $400,000. Whether you’re a first-time buyer, a growing family, or looking to downsize, you’ll find a variety of options that cater to your needs. From cozy bungalows to spacious family homes, each property offers its own unique charm and character, often accompanied by beautiful yards and welcoming neighborhoods.

The city is also conveniently located near major highways, making commuting to Lexington and surrounding areas a breeze. With a strong sense of community, excellent schools, and numerous recreational opportunities, Winchester is a perfect place to settle down and create lasting memories.

Explore the possibilities in Winchester, where your dream home awaits at an affordable price. Discover the warmth of this lovely city and find your place in a community that truly feels like home.

Newest Winchester Homes under $400,000

444 Wellington Way, Winchester
$314,900
4 Beds ⋅ 3 Baths ⋅ 26027910 MLS
This 4 bedroom, 3 bath home is quietly nestled within the Colby Ridge subdivision just off Bypass road. Updates can be seen throughout. Spacious great room, open living/ kitchen areas, large master bedroom with on-suite and walk-in closet, fully fenced yard and so much more. Schedule your showing today!

444 Wellington Way, Winchester
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
107 S Burns Ave, Winchester
$367,700
4 Beds ⋅ 2 Baths ⋅ 26027372 MLS
Timeless character, thoughtful updates, and a walkable downtown location define this distinctive Winchester residence. From the original front door to the beautifully preserved architectural details within, 107 S Burns Avenue reflects the craftsmanship of an earlier era, with original hardwood floors, cherry wood wainscoting, coffered ceilings, custom brick fireplaces and mantels, and original built-ins throughout. Offering four bedrooms and two full baths, the home has been carefully updated while preserving the details that make it unique. The fully renovated upper level provides a private fourth bedroom, full bath, built-in workspace, generous knee-wall storage, and a dedicated heating and cooling system. In the kitchen, custom cabinetry complements an original double-drainboard cast-iron sink, while the main-level bath retains a beautifully reglazed original clawfoot tub. Outdoors, an eight-foot privacy fence creates a secluded backyard setting with an above-ground pool and ample space for relaxing and entertaining. An original carriage-door garage adds another layer of historic character, complemented by off-street parking for up to three vehicles. Located just two blocks from Main Street, the home offers convenient access to downtown Winchester's locally owned restaurants, boutiques, theater, festivals, and community events. College Park and the public library are also just a few blocks away. Beautifully maintained and rich with architectural detail, 107 S Burns Avenue offers an uncommon combination of historic craftsmanship, modern updates, and downtown convenience in the heart of Winchester.

107 S Burns Ave, 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
609 W Barlow Dr, Winchester
$375,000
4 Beds ⋅ 2 Baths ⋅ 26026446 MLS
Welcome to your new home. Move-in ready inside and out, this 4-bedroom, 2-full-bath home offers comfortable living, plenty of finished space, and a backyard that truly feels like your own private retreat! The home has been well cared for and thoughtfully updated, including new flooring throughout the entire finished portion of the basement, new toilets, and a new dishwasher and stove. Step outside and you'll quickly see what makes this property special. The in-ground pool and surrounding outdoor living space are an absolute dream, with extensive improvements completed to make it ready for years of enjoyment. All-new concrete was installed around the pool in 2025, along with a new pool liner and gas pool heater, plus a newer pool pump. A new privacy fence installed in 2023 creates a secluded setting, while the gazebo—complete with electricity—provides the perfect spot to relax, entertain, or spend summer evenings by the pool. The improvements continue with a brand-new back porch completed in May 2026 and a new concrete driveway in 2026, adding even more value and curb appeal. Whether you're entertaining friends around the pool, enjoying a quiet evening under the gazebo, or taking advantage of the additional finished basement space, this home offers a lifestyle that's hard to duplicate. Move in, unpack, and start enjoying it from day one!

609 W Barlow Dr, 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
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