Winchester, KY Homes for Sale with Pool

Spacious Ranch with Pool & Finished BasementOver 4,200 sq ft of versatile living space on a quiet cul-de-sac—perfect for large or multigenerational families!Main Features:• 3 bedrooms on the main floor, including a large primary suite• Ensuite with soaking tub, separate shower, double vanity & walk-in closet• Open living room with wood-burning fireplace & stone surround• Spacious kitchen with

Melodie Lincavage RE/MAX Elite Realty

HISTORIC PRESERVATION AWARD! This stately brick residence, was among the winners of the 2024 Historic Preservation Award by the Clark County-Winchester Heritage Board and the Winchester Historic Preservation Board. Great attention was given to preserving/replicating original features of the home while bringing it to modern day living. Features of this gorgeous home include original heart pine

Angie Conley Dixon Dixon Properties

Attention To Detail!!! Tastefully Renovated 4 Bedroom 4 1/2 Bath Home On College Street! Each Bedroom Has Its Own Private Bathroom! This Perfect Home Has Not Only Been Completely Renovated But An Addition Added To Modernize The Layout And Give You A First Floor Master Suite. The Uniqueness Of This Home Has Been Captured Through The Wooden Staircase and Wonderful Curb Appeal That Were Saved. If

Patrick Arvin Keller Williams Commonwealth

Beautiful Hampton Manor home offers easy access to all Winchester has to offer! Located right off Boone Ave, this home boasts tons of updates including an Entertaiment Kitchen with granite countertops, Bosch appliances and great storage, refinished hardwoods, new windows, Updated bathroom showers, a pool, covered front porch back porch and separate covered area outback to enjoy all summer long. 3

Whitney Ensor Ensor Real Estate LLC

Is it summer yet? This updated ranch is perfect entertaining, featuring an in-ground pool and walk-out basement. Just 10 minutes from Hamburg, enjoy all the perks of Lexington in a quiet neighborhood just over the county line. This all-brick ranch home features 3 bedrooms, 3 bathrooms and a backyard perfect for a summer BBQ. Seller has made numerous upgrades, including all-new vinyl flooring on

Ryan O'Gara Real Broker, LLC

STOP scrolling and LOOK! This charming and pristine home is clean as a whistle and just a short walk to active and historic downtown Winchester. Sit on the covered front porch in the summertime shade or on the deck/patio overlooking the spacious/private backyard. Move-in ready with lots of space inside and out (over 2800 sq.ft. finished!), 4 large bedrooms, 2 full baths (one upstairs and one

Jim Woodrum RE/MAX Creative, Winchester

More photos to come!!! Investment Opportunity! This is the Parent Listing. 2 Parcels listed for $339,500 (MLS listing #s 25005575 and 25005577). 2 Manufactured double-wide homes on permanent foundations sitting on ten acres in Clark County KY. Both properties, 374 and 360 N. Middletown Rd., are being offered together. (Child listing is 360 N. Middletown Rd). Mature garden and LOTS of

Danielle Haggard Keller Williams Commonwealth

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 Mgt

Discover this inviting 3-bedroom, 2-bath ranch-style home with a 2 car garage on a half acre lot! This well-maintained home offers comfort, convenience, and plenty of flexible space both inside and out. There are multiple rooms that can be used as a main living room, family room, home office, or kids playroom. Additional features include vinyl plank floors, a newer roof, a cozy gas fireplace, and

Chad Bowman The Brokerage

Step into this stunning home that seamlessly blends modern comfort with timeless charm. The spacious living room boasts an open-concept design, complemented by beautiful hardwood floors, an abundance of natural light, and a cozy fireplace. The large kitchen is a chef's dream, featuring ample shelving, stainless steel appliances, and breathtaking views. Step outside to a massive deck overlooking a

Jordan James Lifstyl Real Estate

Welcome to 439 Lynnway Drive, where a brand new roof was just installed April 2025. The main floor boasts a primary en-suite, office space, and laundry room, while the second floor offers additional bedrooms and a versatile bonus room. The basement offers private bed/bath, custom bar, home theater, and in-home gym. Step outside and prepare to be enchanted by an outdoor oasis. Outdoor kitchen

Reagan Rainey Dream Maker Realty, LLC

Beautiful large ranch completely remodeled manufactured home on 24 acres with large addition. large bedrooms, family room, dining room, formal living room, 4 Bedroom and 3 baths. 30 foot above ground pool multiple outbuildings, front porch large back patio and just minutes from downtown Winchester. All new Bathrooms, All new Kitchen, All new fixtures, All new flooring. All new paint. House

Tony Phillips RE/MAX Creative Realty

BIG Price Reduction!!! This is The one You Have Been Waiting For! Room For The Whole Family In The Country But Within 5 Minutes Of The Interstate. This 4 Bedroom 2 Bathroom Home With A Living Room And Family Room/Den With Open Kitchen Has It All. Property Includes An Above Ground Swimming Pool, TinyHome/Shed That Has Plumbing Already Ran And Electric At The Pole Right There. This Would Be

Patrick Arvin Keller Williams Commonwealth

Discover your own slice of paradise at this stunning colonial-style home nestled on 71 picturesque acres RIGHT on the Fayette County/Clark County line. 10 minutes to Hamburg. As you approach via a private, gated lane, you'll be captivated by the breathtaking views and tranquil surroundings.The residence offers a perfect blend of charm and modern comforts. With ample living space, the home

Maxine Reyburn Ro&Co Real Estate

*There is an accepted purchase agreement, with 36 Hour kick-out clause * This stately, split-level brick home is situated in the beautiful and desirable Hampton Manor subdivision, right in the heart of Winchester. On the main level, gleaming hardwood floors extend throughout, including the newly renovated kitchen with new granite countertops, new cabinets, all new appliances, new faucet and a

Josh Wood Freedom Realty & Property Mgt

WOW! Exceptional! Attention to detail was clearly taken in the building of this stunning home. Entrance foyer leads to the living rm w/stone gas log fireplace, kitchen and dining rm. Coffered ceiling w/ceiling fan, quartz countertops, backsplash, convection oven w/glass cook top, walk in pantry w/custom cabinets. Primary suite w/tray ceiling, split vanities, walk-in shower, spa-like tub, private

Edwin Burden McCormick Realty Inc.