Courtesy: Freedom Realty & Property Management
859-771-0777
This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. Properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming laminate floors and a brick fireplace; the perfect place to settle in on a cold winter evening. The kitchen features stainless appliances including a double wall oven, ample cabinetry and abundant lighting with plenty of counterspace for cooking your favorite meals. In the primary bedroom is a cedar lined walk-in closet and a spacious and handicap accessible bathroom with a large walk-in shower. Other closets in the home are also cedar lined. Take a ride to the basement on the lift chair to access a second kitchen and additional bathroom. The previous owner had a movie room in the basement and used the custom platform to create tiered seating for movie viewing. The attached garage is spacious enough to hold up to 4 cars or create a workshop space and still have room to park. Other unique amenities include a tankless gas water heater and a backyard shed. Schedule your private showing today and see if this home might be right for you!
Courtesy: Thwaites Realtors LLC
859-987-9119
Welcome to 128 Cherokee Drive, a beautifully maintained home in a quiet and desirable neighborhood. With 5 bedrooms, two full bathrooms, and a second living room on the lower floor, there is plenty of room for the entire family and friends. A spacious backyard , many appealing updates since 2022 including a brand new furnace installed in February of 2026, and exceptional curb appeal and charm, this home is just waiting for its new owner!
Courtesy: Local First Realty, LLC
859-221-8462
Enjoy where you live! Zen like grounds will bring inner peace in this 1,450 sq foot home on over 3 private acres. Covered front and back porches span the width of the house. Get off the grid with the solar panels on the roof (25 yr warranty), six raised garden beds, and fenced chicken coop! Average utility bill $50 in 2025 and $35 in 2024! No worries for fast internet speed, tower is nearby! Sellers have made numerous improvements since purchasing and many warranties are still in place: HVAC (5 yrs left), West Shore windows, front door, bathroom renovation (shower and garden tub), Rennai tankless water heater, humidifier in crawl space, spray foam attic insulation, Gutter Guard and downspouts, Frigidaire Gallery appliances, Maytag Bravos XL washer/dryer, solar powered gate at the driveway with remote control, garage and carport are among the improvements. There's even a frog pond with an electric water pump! This slice of Heaven is 10 miles from downtown Winchester, 10 minutes from George Roger Clark Regional Hospital, a scenic and serene drive down Irvine Road! Sellers are relocating hence the numerous boxes in the photos. Buy now! Seller will provide a home warranty.
Courtesy: Wever Realty LLC
859-893-0036
A rare and refined retreat set on five unrestricted acres in Winchester. Privately positioned and surrounded by natural beauty, this renovated berm-style residence offers the perfect balance of seclusion and sophistication. Inside, you'll find thoughtfully curated updates including fresh designer paint, updated flooring, and a bright, inviting interior that feels both modern and timeless. The kitchen has been tastefully refreshed with contemporary appliances and stylish finishes, offering a functional and comfortable space for everyday living. Featuring three well-appointed bedrooms and an updated bath, the home delivers comfort with understated elegance. Energy-efficient berm construction enhances year-round efficiency and quiet living. Outdoors is where this property truly shines, five acres of unrestricted land create endless potential for recreation, gardening, animals, or simply enjoying unmatched privacy and open space. A covered carport adds convenience, while the setting provides the peaceful lifestyle buyers are seeking. A distinctive acreage property that combines modern updates, privacy, and opportunity all just minutes from town.
Courtesy: Keller Williams Commonwealth
859-721-2121
If you need space, this one delivers. Sitting on just over 8 acres, this brick ranch offers privacy, room to breathe, and a layout that actually makes sense for everyday living. On the main level, you'll find the primary suite, two additional bedrooms, and a formal dining room that works just as well for holidays as it does for weeknight dinners. The heated and cooled sunroom is the kind of spot you'll end up using year-round — morning coffee, evening wind-down, watching the seasons change. A brand-new geothermal heating and cooling system was recently installed, giving you efficient, reliable comfort for years to come. The finished walkout basement adds even more flexibility. There's a private bedroom and full bath, a wet bar, and two bonus rooms that could easily be an office, gym, playroom, or hobby space. There's also a secure fireproof den and direct access outside to a concrete patio area — ready for a hot tub or outdoor seating setup. Outside is where this property really stands apart. The saltwater in-ground pool is ready for summer, and the acreage gives you the privacy you just can't fake. An invisible fence is already in place for pets. Garage space? You've got it. In addition to the attached two-car garage, there's a detached heated and cooled building with multiple bays and finished space — including an upper-level loft — ideal for a workshop, studio, guest setup, or whatever you've been wishing you had room for. Major bonus: the home is priced below appraisal. If you've been looking for land, function, and flexibility — without giving up comfort — this one is it.
Courtesy: RE/MAX Creative, Winchester
859-422-2000
This Colby Ridge neighborhood townhome location is hard to beat as it is just minutes from Kroger, Walmart, the Bypass, interstate access, and a wide variety of restaurants and everyday conveniences. The main floor offers a convenient half bath, a welcoming living room that opens naturally into the dining area and kitchen, and a laundry room tucked just inside the one-car garage entry. Off the dining area, step out onto the back deck (built in 2023) overlooking a fully fenced yard which is a great spot to relax or let pets play. The unfinished walkout basement adds plenty of storage space with room to expand in the future. Upstairs, you'll find three bedrooms and a full bath, including a primary suite with double closets and a private bath with a shower. With a practical layout, inviting outdoor space, and an unbeatable location, this townhome is ready for its next owner.
Courtesy: Tru Life Real Estate
859-785-1986
This updated home offers easy access to I-64 and downtown Winchester. See ceiling fans in every room, upstairs bonus room, modern lighting in the kitchen and bath, and new appliances, countertops, and backsplash. Enjoy a peaceful, quiet neighborhood and a relaxing rural view from the backyard. A clean, comfortable, move-in-ready home with thoughtful upgrades throughout.
Courtesy: Rector Hayden Realtors
502-863-2424
Great opportunity to own this well loved home in a very convenient location in growing community of Winchester. Lots of character and charm upon entry into the entry foyer with nice staircase, opening to large living room with a lovely mantel. Spacious dining room with built in corner cabinet flows into kitchen with plenty of cabinetry and counter space. Large laundry room with access to rear yard. A partial bath completes main level. Upstairs has two spacious bedrooms and a full bath. Lots of closet space including a cedar closet. Most of the main floor has nice recently installed vinyl plank flooring. Large lot with trees and space for kids to roam and explore. Great location near public library, within walking distance of downtown and popular College Park Facility. Several recent large ticket replacements-roof, siding, water main from street, and water heater and refrigerator!
Courtesy: Freedom Realty & Property Management
859-771-0777
Welcome to 6 Hart Avenue in Winchester, Kentucky — a home that just feels right from the moment you pull up. This well-maintained tri-level offers 4 bedrooms, 1.5 baths, and a smart layout that gives everyone room to spread out while still feeling connected. The tri-level design creates natural separation of space — perfect for busy households, guests, or a dedicated home office. Rich hardwood floors bring warmth and timeless character, while the functional floor plan makes everyday living both comfortable and practical. Outside, you'll love the corner lot setting, fresh privacy fence, and the classic, low-maintenance brick and vinyl exterior. Situated on approximately .2 acres, this home offers just the right amount of yard without the overwhelming upkeep. And talk about convenience — you're just minutes from shopping in Winchester and quick access to I-64, making commuting a breeze. Well cared for, ideally located, and ready for its next chapter — this Hart Avenue home might just steal your heart!
Courtesy: Biederman Real Estate
859-277-2030
Nicely updated split-level home with a large, fenced backyard, located on a quiet cul-de-sac. This energy-efficient home boasts a brand-new HVAC system, a recently replaced roof, fresh paint and stylish new LVP flooring throughout the house. The large kitchen has updated countertops and cabinets, as well as brand-new stainless steel appliances with three-year warranties. Both bathrooms have been updated with new floors and vanities and the upstairs bathroom has a double vanity and fresh new tiles. There's plenty of room in this house, with three bedrooms and the option of a fourth downstairs. And get your cars out of the rain and snow in the large double garage. Many amenities like shops and restaurants are within walking distance and Lexington's Hamburg Pavilion is only 11 miles away! This home is move-in ready!
Courtesy: Kentucky Residential Real Estate, LLC
859-229-5974
Stunning new construction offering 5 bedrooms, 3.5 bathrooms, sitting on roughly 2.5 serene acres. This home is surrounded by picturesque farmland and panoramic views. 4 bedrooms are located on the main level for ultimate convenience. Offering the perfect blend of space, style, and serenity. Features include open concept layout, spacious kitchen with kitchen island, granite counter tops, hidden walk in pantry with custom cabinets and well appointed appliances. Hardwood floors and tile throughout. Primary bathroom is gorgeous with a freestanding soaker bathtub, tile shower, custom dual vanities and granite countertops. Unwind on the covered back porch. Cozy up by the stone fireplace in the great room. Enjoy the separate laundry room also with custom cabinets, folding space and granite. This home offers and abundance of sunlight and a side entry garage. Large walk-in storage room for all your extra items! Covered entry space for all your deliveries. Roughly 21 minutes to Hamburg in Lexington, 20 minutes to I-75 / I-64 interchange, with multiple drive options. Roughly 5 minutes to grocery options and variety stores. Don't wait to build, this one is move in ready, just add your decor and enjoy!
Courtesy: Ensor Real Estate, LLC
859-749-0892
Investors take note, tenant occupied home, 3 bedrooms, 1 bathroom, one level living! Flippers, downsizing, or First-time buyers get ready! Wood style floors, covered front porch, back yard with patio...Do not miss an opportunity to add to your rental portfolio investment, start your real estate adventure, or make this home your own! Home is occupied 24-hour notice is required to show.
Courtesy: Freedom Realty & Property Management
859-771-0777
Welcome to Woodbine Ct! Tucked away at the end of a quiet cul-de-sac, this adorable brick split-level home offers the perfect blend of charm, space, and flexibility. Featuring 4 bedrooms and 2 full bathrooms, this home is packed with possibilities including the option for two primary suites. Enjoy a traditional primary bedroom on the main level, plus a spacious downstairs retreat complete with a beautifully updated bathroom featuring an excellent shower, a comfortable sitting area, and the privacy ideal for guests, in-laws, or a true owner's suite escape. Step outside to a nice-sized, flat, fenced-in backyard perfect for kids, pets, entertaining, or simply relaxing in your own private space. With its desirable cul-de-sac location, versatile layout, and thoughtful features throughout, this Woodbine Ct home is one you won't want to miss!
Courtesy: Southern Legacy Realty
859-866-1040
Welcome home to this cozy brick charmer in the desirable Belair Subdivision of Winchester, KY! This inviting 4 bedroom, 1 bath home offers comfortable living with a warm electric fireplace perfect for relaxing evenings. The spacious layout provides flexibility for family, guests, or a home office. Step outside to a fully fenced backyard ideal for pets, play, or enjoying quiet mornings with your coffee. You'll also appreciate the added storage shed for tools and hobbies, plus a 1 car garage for convenience. Energy-efficient solar panels help keep utility costs down, adding even more value to this sweet home. Located just minutes from shopping, restaurants, and everyday conveniences, this property blends comfort, practicality, and location all in one. If you're looking for cozy living in a convenient Winchester neighborhood, this one is ready to welcome you home.
Courtesy: CENTURY 21 Advantage Realty
606-451-1021
SELLER is motivated to offers! Welcoming you to this lovely updated throughout 3 bedroom, 2 full bath ranch! As you step into the home with its cozy feeling, and spacious space in every room, including a full unfinished basement wonderful for storage or to finish that into living square footage, great size back yard with large back patio perfect for the family gatherings, also a partial fenced in yard. A large detached garage which is great for a man cave, or work shop area. Located in the heartland of Winchester, where you're close to schools, parks, downtown amenities. This property offers small-town charm. Minutes to I-75, and Lexington. Schedule your showing today before this one slips away!
Courtesy: Tom Goebel & Company
859-744-3637
This cozy 2-bedroom, 1.5-bath home is the perfect fit for first-time buyers or anyone looking to expand their investment portfolio. The inviting living room features a propane-operated fireplace that provides a reliable backup heat source. The spacious primary bedroom includes his-and-her closets, and both bedrooms are equipped with additional split units for personalized comfort. A full appliance package conveys with the property, including the stove, refrigerator, washer, dryer, dishwasher and garbage disposal—making this home truly move-in ready. Out back, a large deck extends your living space outdoors and creates the perfect setting for entertaining. Whether hosting summer cookouts, enjoying quiet evenings, or gathering with friends, this generous outdoor area adds tremendous value and versatility. Comfortable, efficient, and thoughtfully equipped, this property is ready to welcome its next owner. With close proximity to shopping, schools, and parks, the location simply can't be beat.
Courtesy: Tom Goebel & Company
859-744-3637
Begin the New Year in your own home! It's a new beginning...Make an appoint to look at this two bedroom, one bath ranch. It has new paint and updated flooring. Range refrigerator and dishwasher are included, There is a nice size laundry room. The kitchen has lots of cabinets and there is an additional pantry in the hall. The dining room is off the kitchen and overlooks the living room. The rear entrance is covered and can be used as a carport if needed. The back yard is large and beautiful in nice weather. Worth taking a look! Lock Box on back door. Come On By and BUY!
Courtesy: Marshall Lane Real Estate - Lexington
502-682-1226
Welcome to this charming river front house. Step out your back door and you are immediately at the river. Open floor plan with a wood burning fireplace. Metal cabinets and epoxy floors on the first level are designed to survive in case of a flood. First floor bedroom with enough room for a King sized bed. Upstairs you will find another bedroom and a half bath. Sip your morning coffee on your back patio area or deck over looking the Kentucky River. There is a large carport for your truck and enough room for a boat as well. The large lot will accommodate a fire pit where you can gather with friends and family. This property is in a flood zone. This property was used as a rental and an air b&b. Make it your own or rent it out, the possibilities are endless.
Courtesy: The Brokerage
859-983-7365
Welcome to 233 E. Washington Street, a charming ranch-style home offering comfort, space, and convenience in the heart of Winchester. The Roof, Windows and HVAC are updated. This 2-bedroom, 1-bath residence features an open-concept layout designed for easy living and everyday functionality. LVP flooring runs throughout the home, providing a clean, modern look that's both durable and low maintenance. The living room and both bedrooms boast tall ceilings, creating an airy, open feel and enhancing the sense of space throughout the home. Both bedrooms are generously sized, offering flexibility for comfortable living, a home office, or guest accommodations. Step outside to a large backyard that backs to Mack Alley, providing room to relax, entertain, or enjoy outdoor activities. Whether you're hosting friends, gardening, or simply unwinding, the outdoor space is a standout feature. Conveniently located just 4 minutes from I-64 and approximately 23 minutes from Hamburg in Lexington, this home offers easy access to major routes while still enjoying a neighborhood setting. *Interior photos have been virtually staged to showcase the home's layout and potential. Select exterior images utilize AI to illustrate the property's appearance without snow.
Courtesy: ERA Select Real Estate
859-296-1525
Charming, Move-In Ready Ranch with Updates & Fenced Yard! Welcome home to this super cute and well-maintained 3-bedroom, 2-bath ranch offering easy one-level living and a smart, functional layout. Close to shopping and the interstate for easy commutes. Recent improvements include a brand-new roof, fresh interior paint throughout, a new garage door and opener, and a new stainless-steel appliance package in the kitchen—so the big-ticket items are already done for you. The home features durable vinyl plank flooring throughout, providing a clean, modern look and easy maintenance. An attached one-car garage adds everyday convenience, while the fully fenced backyard is perfect for pets, play, or relaxing outdoors. Whether you're a first-time buyer, downsizing, or looking for a turnkey investment, this home checks all the boxes: updated, affordable, and truly move-in ready. Don't miss this one!
Courtesy: Woods Realty Group
859-644-5077
Be among the first to discover this exceptional property! This is a brand new listing, presenting a unique opportunity to own a home in a highly sought-after location. Imagine living in a neighborhood where everything you need is just a stone's throw away. This fabulous property boasts not only a full basement, offering endless possibilities for recreation, storage, or a home office, but also an ensuite bathroom in the primary bedroom. Enjoy privacy and convenience in your own personal sanctuary. DON'T MISS OUT!! This incredible property wont stay availabe long. Schedule a viewing and take the first step toward owning your dream home! This could be the one!!
Courtesy: Berkshire Hathaway de Movellan Properties
859-266-0451
Located in the Mallard Place subdivision, this ranch home offers 3 bedrooms, 2 full baths, and 1 half bath with approximately 2,652 square feet of finished living space. The home features new flooring in the main living area and a functional single-level layout. The kitchen includes an eat-in area, breakfast bar, double oven, cooktop, microwave, dishwasher, and refrigerator, with laundry conveniently located on the main level. The first floor primary bedroom has a spacious ensuite bath with walk in closet and soaking tub. A large glass-enclosed sunroom provides additional living space and overlooks the landscaped .47-acre lot. Conveniently located near Colby Road and McClure Road with easy access to Winchester amenities. This is a must see!
Courtesy: RE/MAX Creative, Winchester
859-422-2000
Courtesy: Bluegrass Properties Group
859-619-8888
Be the first to call this stunning new construction home! Perfectly situated in the heart of Winchester, this two-story residence offers a fresh, modern feel with convenience at your doorstep. Step inside to discover a bright and airy open-concept main level, featuring durable and stylish Luxury Vinyl Plank (LVP) flooring throughout. The kitchen is a true showstopper, boasting crisp white cabinetry, gleaming quartz countertops, stainless appliances, and a large center island that overlooks the spacious great room—ideal for entertaining guests or keeping an eye on the family. A convenient half bath rounds out the main floor. Upstairs, you will find three comfortable bedrooms and pristine bathrooms finished with elegant tile work. The primary bedroom features a vaulted ceiling, lots of natural light, walk-in closet and en-suite bathroom with tile flooring, dual sink vanity, and step in shower! The guest bedrooms are a lovely size with lot of natural light and a guest bathroom to share with dual sink vanity and a tub/shower combo with tile surround. If you are looking for low-maintenance luxury and a prime location, this is the one. You will love the expansive back yard while sitting on your lovely deck. Extra features include a combination of casement and traditional windows, a fully insulated garage and garage doors, 2x6 construction, and poured wall foundation crawl space (not block). Located on a quiet, established street, you will love it!
Courtesy: Keller Williams Legacy Group
859-544-6175
Country Living with Convenience — 5 Fenced Acres in Winchester, KY Enjoy the perfect blend of peaceful country living and easy access to town with this well-maintained home on 5 fully fenced acres in Winchester, KY. Conveniently located just 30 minutes to Lexington, 5 miles to I-64, 10 minutes to Mt. Sterling, and 15 minutes to Winchester, this property offers country living without sacrificing convenience. Step inside to a spacious, functional layout featuring 5 bedrooms and 2 full bathrooms, offering room for everyone—whether you need extra bedrooms, a home office, playroom, or guest space. The home provides comfortable everyday living, a welcoming main living area, and an open feel that makes it easy to entertain or relax. Outside, you'll love the gated entrance and fully fenced acreage, ready for cattle, livestock, or hobby farming. The chicken coop stays, making it easy to start your homestead lifestyle right away. Modern conveniences include Spectrum fiber-optic internet availability and an ADT security system that remains. If you've been searching for room to roam, a property set up for animals, and country charm close to town—this one checks every box. Schedule your showing today!
Winchester is located in Kentucky. Winchester, Kentucky 40391has a population of 18,993. Winchester 40391 is less family-centric than the surrounding county with 25.5% of the households containing married families with children. The county average for households married with children is 25.74%.
The median household income in Winchester, Kentucky 40391 is $47,034. The median household income for the surrounding county is $59,294 compared to the national median of $69,021. The median age of people living in Winchester 40391 is 36.9 years.
The average high temperature in July is 85.8 degrees, with an average low temperature in January of 22 degrees. The average rainfall is approximately 45.8 inches per year, with 9.4 inches of snow per year.
