Winchester, KY Homes 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

Beautifully updated 3-bedroom, 2-bath home in the heart of Winchester! Brand-new siding and a welcoming front porch set the tone. Inside, you'll find a light-filled living room with a decorative fireplace and cozy reading nook, plus refinished hardwood floors throughout most of the main level. The first-floor bedroom has new carpet and easy access to a fully updated full bath. The remodeled

Austina Bruton The Howard Realty Co

This ranch style house is located minutes from Fayette County line and minutes from the I-64 and I-75 corridors. This house features 4 bedrooms and 2 full baths on a walk-out basement. The owners remodeled several years ago with new kitchen and primary suite. The house is situated on a .53 acre lot within a quiet residential neighborhood. Looking for a house to make your home? come see this

Craig Bridgewater Bridgewater Real Estate

This beautifully 4-bedroom, 2-bath home sits on a spacious corner lot on a peaceful street near Lexington Avenue. This brick ranch style home is move in ready, and waiting for you. This home offers a great location to downtown Winchester and for all your shopping needs. Multiple fruit trees located on the property! Call and schedule your showing today!

Travis Trimble Paragon Realty Partners

Nice 3 bedroom, 2 bath, all one level, ranch home! Convenient location! Nice patio to sit out back in the mostly privacy fenced in yard. Only needs a few panels to be completely fenced if desired. One car garage. Easy to maintain lot. Large kitchen. Good sized bedrooms. Windows, HVAC, and roof all replaced within the last 8 years. This will make someone a great home!

Jason Townsend Kentucky Residential Real Estate, LLC

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

E. Clark Toleman Real Estate Appraisal Services

Welcome to 17 Euclid Ave, a charming two-story home in the heart of Winchester! This beautifully maintained property features 3 bedrooms and 2 full baths, offering ample space and comfort. Enjoy the outdoors with a spacious deck perfect for relaxing or entertaining, surrounded by mature trees that provide shade and privacy. Convenient off-street parking ensures easy access, and the home's prime

Donna Thwaites Thwaites Realtors LLC

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

Welcome to this beautifully updated 3-bedroom, 1-bath home, perfectly situated in the vibrant heart of Winchester. Bursting with charm and character, this home offers the best of modern updates and classic appeal. Step inside to discover a bright, open living area with new flooring, fresh paint, and stylish finishes throughout. The updated kitchen features sleek cabinetry, granite countertops,

Jana Hooten Rock N' Realty LLC

Charming 3-Bedroom Home with Modern Upgrades & Outdoor Living!Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that offers both comfort and functionality. Step inside to discover a spacious open-concept living and dining area, perfect for entertaining or relaxing with family. The generous kitchen features ample counter space, a walk-in pantry, and plenty of room for the

Cathy Cornett-Wilson Rector Hayden Realtors

This charming 2 - story townhouse is in a prime location.. Welcome to this beautifully maintained 2 bedroom, 1.5 bath townhouse offering the perfect blend of comfort, style and convenience. Spread over two spacious levels, this home features an inviting living area, a modern kitchen with ample cabinetry and a cozy dining space-perfect for every day living or entertaining guests. Upstairs,

Kimberly Fugate Keller Williams Commonwealth

This brick ranch style home is located on a quiet cul-de-sac in the residential neighborhood of Forest Park. Enjoy leisurely living in this one level home featuring a 12 X 18 Florida room overlooking a private back yard. The location is minutes from Lexington Avenue and the family/fun Legacy Park. It is move in ready and if you are ready, you may be the next owner. Make an appointment today!

Craig Bridgewater Bridgewater Real Estate

Here's your chance to own a nice investment property. This duplex has a 2 bed 1 bath unit and a 2 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

Here's your chance to own a nice investment property. This duplex has a 3 bed 2 bath unit and a 3 bed 2 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

Here's your chance to own a nice investment property. This duplex has a 3 bed 1 bath unit and a 3 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

Here's your chance to own a nice investment property. This duplex has a 2 bed 1 bath unit and a 2 bed one bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

Here's your chance to own a nice investment property. This duplex has a 3 bed 2 bath unit and a 2 bed one bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

Relax in your private paradise! The fully privacy fenced backyard hides the pool and deck area along with the really cool hot tub room, huge dog kennel, and storage shed. 3 bedrooms, all one level, newer roof and HVAC system. Come see what sets this home apart from all the rest!

Jason Townsend Kentucky Residential Real Estate, LLC

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

This is the one you've been waiting for! Room for the whole family with country charm just five minutes from the interstate. This 4-bedroom, 2-bath home features both a living room and a cozy den/family room, plus an open kitchen perfect for entertaining. Outside, enjoy an above-ground pool and a versatile tiny home/shed with plumbing and electric nearby—ideal as a man cave, she shed, or

Patrick Arvin Keller Williams Commonwealth

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

Welcome Home - Comfortable Living or Smart Investment!Step into this inviting townhome, offering both spacious comfort and excellent investment potential. Featuring two bedrooms and two and a half bathrooms, this well-designed unit boasts a generous living area with a ventless fireplace, creating a warm, welcoming atmosphere.The home's layout connects the living room, dining area, and kitchen

Kim Dice EXP Realty, LLC

Welcome Home - Comfortable Living or Smart Investment!Step into this inviting townhome, offering both spacious comfort and excellent investment potential. Featuring two bedrooms and two and a half bathrooms, this well-designed unit boasts a generous living area with a ventless fireplace, creating a warm, welcoming atmosphere.The home's layout connects the living room, dining area, and kitchen

Kim Dice EXP Realty, LLC

Unique Setting... Unlike Any Other!Wake up to the beauty of the surrounding countryside — every single day. This 3-bedroom, 2.5-bath townhome is nestled in the desirable Royal Oaks Village, just one mile from I-64, making it a perfect location for both homeowners and renters alike.This low-maintenance property features tile flooring in the foyer, kitchen, and baths. The kitchen comes fully

Kim Dice EXP Realty, LLC

Completely remodeled 4 bedroom, 2.5 bath home located in the heart of downtown Winchester. This home features a spacious open floor plan, a first-floor primary suite and a lot of charm. The kitchen, living, and dining areas flow together seamlessly, offering ample space and natural light. Upstairs includes three additional bedrooms and a full bath. Outside, enjoy a large backyard with pool and

Erin Hurst Bluegrass Properties Group

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 offers ample parking with a rare 3-car garage—perfect for storage or a

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

** Seller is offering a $10,000 credit at close with an acceptable offer!**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

Zachary Otis HomeLand Real Estate Inc

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

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

Ernesto Martinez Berkshire Hathaway HomeServices Foster Realtors

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

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

Serena Cassidy Coldwell Banker McMahan