Winchester, KY Homes for Sale under $300,000

Home is quietly nestled within the Wesleyan Park subdivision just off the Winchester Bypass. While convenient location is obvious this home boast many updates throughout. Including flooring, appliances, New roof, HVAC, Water heater and so much more. Schedule your showing while you can!

Michael Hilario The Agency

The country house you have been looking for! 3 bed, 2 bath with an amazing front porch where you can sit and view the small stream in the front yard! Sitting on 3.17 acres with approximately 735 feet of road frontage which should allow for division for a second lot / home. 565 sq ft all metal detached garage, a livestock barn with 3 stalls, and a back deck with farm views. High speed internet

Jason Townsend Kentucky Residential Real Estate, LLC

This phenomenal property has had so many updates including the addition of a full bath on the second floor, an updated electric panel, new wiring throughout, added electrical outlets, all new plumbing, a heat pump for the second floor (there is gas heat on the first floor) and a walk-in closet in the primary bedroom on the first floor. The owners have given meticulous attention to every

Susan Colwell Colwell Realty Professionals, Inc.

A timeless brick ranch in one of Winchester's most established neighborhoods on a corner lot. This 3 bedroom, 2.5 bath home offers two living areas and a cozy fireplace. Spacious backyard, covered front porch, and a wrap-around driveway for a private entrance. All just minutes from downtown, schools, and I-64. The home combines classic comfort, location, and room to grow on a walk-out basement.

Brett Bussell Turf Town Properties

Welcome home to this beautifully remodeled 3 bedroom, 2 bathroom brick ranch in a well-established neighborhood. Nearly everything is new, including the roof, plumbing, and kitchen appliances. You'll love the refinished hardwood floors and stylish fixtures throughout. The kitchen features gorgeous granite countertops and an island with bar seating. One bathroom offers a tiled shower with a

Michelle Blackburn RE/MAX Creative, Winchester

Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

Darrell Tackett Dream Maker Realty, LLC

Modern Ranch residence full un-finished basement, large lot.

E. Clark Toleman Real Estate Appraisal Services

Beautiful remodeled move-in ready four bedroom, 2 full bath split foyer. Here are some of the updates: New LVP floors throughout entire home. New carpet on the stairs. New paint throughout home. New fan with remote in living room. Range dishwasher, & new refrigerator stay. New mirrors and lights above them in both baths. New garage door and garage door opener (with 2-year warranty). One side of

Joyce Ratliff Tom Goebel & Company

This cozy three-bedroom ranch on a basement is only minutes to downtown and the Veterans Memorial Bypass. This meticulously maintained home is full of natural light. The partially finished basement offers lots of potential for customization. The fenced backyard includes a deck and patio perfect for entertaining and a nice-sized storage building. Perfect for a first-time homebuyer or someone

Sarah Hess Keller Williams Commonwealth

Built in the 1940s, this 3-bedroom, 2-bath home blends timeless character with thoughtful updates. Enjoy original wood floors, a spiral staircase, a gorgeous fireplace, and an updated kitchen with ample storage. Flexible nooks, a huge master closet, and mudroom add convenience. Outdoor living shines with a covered front porch, oversized back deck, and private backyard. Walk to downtown shops,

Zachary Otis HomeLand Real Estate Inc

Beautiful, Old-World style in the heart of Winchester! From the red, domed porch roof to the arched doorways and multiple fireplaces, this home is full of character and class. Being sold as-is, but with many renovations and updates already done to maintain and restore the charm of this old beauty including a new shingle roof (2024), replaced porch boards, and a fresh coat of interior paint. The

Josh Wood Freedom Realty & Property Management

Back on market due to buyer financing, no fault of the seller! Situated on 5 scenic acres along a highly sought-after country road, this 3-bedroom, 2-bath property presents an excellent opportunity to create your dream rural retreat. The home features a functional layout with a spacious living area, an eat-in kitchen, and a primary suite with its own bath. Two additional bedrooms offer

Michelle Blackburn RE/MAX Creative, Winchester

Here is the Blank Canvas to build your Dream Home in the Plantation Subdivision. This two story brick building, formerly the Sales Office for the Subdivision, has been gutted to offer the unique opportunity to build a 3118 Sq Ft Home consisting of Four Bedrooms, Two and Half Baths, an open concept on the main level with the addition of a two car garage. Contact listing agent to discuss current

Melia Hord Keller Williams Bluegrass Realty

Wonderful investment opportunity! Cash flowing triplex located in the heart of Winchester. One unit has just been renovated and is ready for a new tenant. The other two have longstanding tenants who pay every month. Great price for the rent potential!

Andrew Jarvis Lifstyl Real Estate

Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

Andrew Fugitt Coldwell Banker McMahan

Need to see inside of this one! Seller bought in May 2021. Remodeled kitchen. Removed one wall between kitchen and living room. Installed a granite bar/island and countertops. Installed all new kitchen cabinets. Installed all new stainless steel appliances (including a top-of-the-line Kitchen Aid dishwasher). Put in deep sink and garbage disposal. Pantry cabinet beside refrigerator.

Joyce Ratliff Tom Goebel & Company

Welcome to 20 Bon Haven Avenue, a beautifully renovated 4-bedroom, 3 full bathroom home ideally located directly across from the new Legacy Grove Park in Winchester, KY. This spacious residence blends modern upgrades with timeless charm, offering the perfect retreat for families and entertainers alike.Step inside to find a bright and airy open floor plan, highlighted by brand-new plumbing and

Jacqueline Marchildon Lifstyl Real Estate

Incredible value in the highly desirable Oakmont subdivision! This completely remodeled 3 bedroom, 2.5 bath home is truly move-in ready with all new paint, flooring, and granite countertops in every bathroom and kitchen. The stylish kitchen shines with an abundance of cabinetry, updated appliances and tile backsplash, flowing into the dining area that overlooks the deck and oversized

Jennifer Parsons RE/MAX Elite Lexington

This charming mid-century home was completely renovated in 2022 and has been beautifully maintained. Step inside and enjoy the warmth of a cozy living room complete with a wood burning fireplace to keep warm on cool fall evenings. Around the corner, the kitchen gleams with stainless appliances, white cabinets and granite countertops. New tile flooring and new carpet completed the renovation

Josh Wood Freedom Realty & Property Management

This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

Tyler I Back The Brokerage

NEW PRICE! With limited inventory on the market, don't wait too long to view this brick ranch that offers comfort, updates, and a spacious outdoor area—all at an affordable price!This home features 3 bedrooms and 1 full bath, with fresh interior paint and newer laminate flooring for a clean, modern feel. The living spaces are filled with natural light, making the home feel warm and

Kathy Burton Coldwell Banker McMahan

*Seller offering up to $5,000.00 toward buyer's closing costs!!* Charming & Updated Home in College Park! This beautifully renovated 3-bedroom, 1-bath home in Winchester blends timeless charm with modern updates. Featuring new roof electrical, plumbing, kitchen, flooring, bathroom, fresh paint, and brand-new appliances, this home is truly move-in ready. Situated on a spacious corner lot, it

Chaney Hughes Guide Realty, Inc.

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

Josh Wood Freedom Realty & Property Management

Lovely one level brick ranch on a corner lot conveniently located in the Meadows just off of McClure Rd. 3 bedroom, 2 full bath with a beautiful yard and a storage building out back.

Jason Townsend Kentucky Residential Real Estate, LLC

Brand new 4 Bedroom 2 bath home on an acre lot. Home features Master Bedroom suite, separate utility room, new front and back decks to enjoy your peace and quiet. Other features are new fencing and new septic tank. Move-in ready. Close to shopping and restaurants, less than 4 miles. 13 miles to I-75 and 6 miles to I-64. Within 30 minutes to Richmond and Hamburg area of Lexington.

Robin Horn Keller Williams Commonwealth

Great location close t o down town Winchester, shopping, school, recreation areas, I 64 ,in beautiful Winchester,nice 3 bedroom ,1 bath , all brick home, with all appliances, including washer and dryer roof 1 year old, fenced yard, storage building private drive. nice back yard and more.

Sophia Herald Herald Real Estate

Mendel Tipton Natural Bridge Realty

New Construction! Modern 3 Bedroom, 2 Bath Home Near Downtown Winchester!Step into this beautiful new construction 3 bedroom, 2 full bath home featuring an open concept layout, granite countertops, stainless steel appliances, and stylish finishes throughout.The large backyard boasts a generous deck perfect for entertaining, gardening, or relaxing. Whether you're hosting a summer

Nena Honaker Tom Goebel & Company

Absolute Auction - October 11 at 10:00 AM!Bidding will be live and online at Malloryauctionco.com.Open Houses: Sept 25 from 5 to 7 and Oct 5 from 1-3This charming brick ranch offers the perfect blend of comfort and convenience. Featuring 3 bedrooms and 2.5 baths, this home boasts a fully finished basement—ideal for additional living space, a home office, recreation, or storage.

Donna Thwaites Thwaites Realtors LLC