Winchester, KY Homes for Sale with Pool

Visitors to the farm are greeted by a substantial stone entry before traveling a gently winding path to the circular drive. There rests the grand residence, offering an ideal setting for entertaining family & friends. Ten minutes from Hamburg, the farm is located on the convenient Lexington/Winchester Road. Lovely views abound and the property retains remarkable privacy. The 13,500 square foot

Zach Davis Kirkpatrick & Company

Discover timeless elegance and modern luxury in this newly constructed residence, perfectly situated on over 2.5 acres in Winchester. With 2,670 sq ft of custom designed living space, this 4-bedroom, 2.5-bath home offers craftsmanship, high-end finishes, and exceptional outdoor living. White oak engineered hardwood flooring, moulding throughout, and exquisite details. The spacious great room

Michael Hilario The Agency

Beautiful 1.5-story brick home on a cul-de-sac with in-ground pool and walkout basement! The main level features hardwood floors, office, formal dining room, and spacious family room with gas fireplace. The kitchen includes stainless appliances (all convey), double oven, gas cooktop, island, eat-in area, and large pantry. Oversized mudroom/laundry adds great storage. First-floor primary suite

Terri McGraw FC Tucker Bluegrass

Step into timeless elegance with this breathtaking modern Victorian-style masterpiece, perfectly positioned on 4.39 acres with panoramic views of sunrises, sunsets, and distant mountains. Designed and built by Tom Padgett, this home is rich in character and detail—from hand-hewn wood beam ceilings to Waterford crystal chandeliers. The grand 2-story foyer welcomes you into a flowing layout that

Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

Escape to your own private retreat with this beautiful brick ranch set on 8 plus acres. This home boasts a bright and airy sunroom, perfect for enjoying morning coffee watching the sunrise or unwinding with the nature views. The fully finished basement offers extra living space, while the in-ground pool is ready for summer fun. This property offers a two-car attached garage as well as a

Kathryn Cheuvront Coldwell Banker McMahan

Spacious 3-Bedroom Home on Nearly 5 Acres in Winchester, KY!Discover country living at its finest with this beautiful 3-bedroom, 3-bathroom home set on nearly 5 acres of picturesque land. Featuring beautiful hardwood floors, a finished basement, and plenty of space for entertaining and friends, this property is designed for comfort and social gatherings. Enjoy the in-ground pool, pole barn,

Terry Billiter Premier Property Consultants

--Contingent Offer w/ 72hr Kick-Out in place--Welcome to 439 Lynnway, an expansive 5,000+ sq ft home, where every inch was designed for comfort, style, and entertainment. The main floor features a primary en-suite, office space, and laundry area. As you make your way upstairs, you will find spacious bedrooms throughout. New roof placed early 2025.The finished basement is a standout,

Reagan Rainey Dream Maker Realty, LLC

Check out 420 Alexis Way in Winchester! This stunning home features a beautiful great room, fully equipped kitchen, extra garage and an inground pool. The primary suite is a luxurious retreat with a spa-like bathroom. With three additional bedrooms and a bonus room, there is plenty of space. The outdoor area is perfect for relaxing by the heated pool. Extra touches include crown molding and

Edwin Burden McCormick Realty Inc.

Situated on 1.5 acres along a sought after country road, this one level home features a split bedroom layout with a primary suite that includes an en suite bath and walk in closet. The living room offers vaulted ceilings, hardwood floors, and a gas log fireplace, opening to a dining area and an eat in kitchen. A sunroom provides additional living space with skylights and views of the backyard.

Shane Underwood Keller Williams Commonwealth

*Seller has accepted an offer with a 24 hour kickout clause.* Located in the Windridge neighborhood with easy access to both Bypass Rd and Boone Ave, this charming brick ranch offers 3 bedrooms, 2 full baths, and character throughout. Inside, you'll find hardwood and tile floors (no carpet!), a spacious kitchen with plenty of cabinet space that opens into the dining area and living room, complete

Michelle Blackburn RE/MAX Creative, Winchester

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

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

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

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

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