Winchester KY Real Estate & Homes for Sale

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Open House:

Sunday, 8/23 2:00-4:00PM

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Beds:
4
Baths:
3.00
Sq.Ft.:
1,978
Status:
Active
MLS#:
26015608
Type:
Single Family
Subdivision:
Hibiscus Terrace
Lot size:
0.23 Acres
Year built:
1999
A broker reciprocity listing Courtesy: Keller Williams Commonwealth 859-721-2121
View additional info

ADDITIONAL INFORMATION

Welcome to 107 Hibiscus, where thoughtful updates, quality craftsmanship, and exceptional maintenance come together in this spacious 4-bedroom, 2.5-bath home. Offering a versatile floor plan with generous living spaces, this move-in-ready property has benefited from approximately nearly $70,000 in improvements over the past several years, providing peace of mind and modern finishes throughout. Major mechanical updates include replacement heat pumps (downstairs in 2020 and upstairs in August 2024), all new energy-efficient windows installed in 2025 with a transferable 10-year warranty, a new three-panel sliding back door, recently cleaned ductwork, spray-foam insulated crawl space, additional attic insulation, a roof replaced approximately 8-10 years ago, and garage doors replaced approximately two years ago. Inside, you'll appreciate the beautiful ¾-inch solid oak hardwood flooring throughout the main level, fresh interior paint, updated light fixtures, ceiling fans, new door hardware, elegant crown molding, a cozy gas log fireplace, and renovated bathrooms featuring updated tile, mirrors, lighting, faucets, and refreshed cabinetry. The beautifully updated kitchen is designed for both everyday living and entertaining, offering new granite countertops, freshly painted cabinetry, all-new stainless steel appliances including a gas range, dishwasher, microwave, and refrigerator, plus a convenient coffee bar that adds both style and functionality. Outdoor living is just as impressive with a large deck, a freshly painted front porch, and a high-quality custom-built storage shed constructed with 12-inch studs for exceptional durability. If you're searching for a meticulously maintained home where many of the major updates have already been completed, 107 Hibiscus deserves a place at the top of your list. Buyer to verify all aspects of the property, including but not limited to square footage, schools, boundaries, and any information deemed important to the purchase. Schedule your showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
1,840
Status:
Active
MLS#:
26015653
Type:
Single Family
Subdivision:
Bradley Place
Lot size:
0.28 Acres
Year built:
2012
A broker reciprocity listing Courtesy: Ensor Real Estate, LLC 859-749-0892
View additional info

ADDITIONAL INFORMATION

Very motivated sellers, Get here first, make an offer on this 4 bedroom, 3 bath, 1 1/2 story home, 2 car garage, showroom fresh condition, vaulted ceiling, hardwood floors, tile, carpet, deck, nice back yard, call today to view.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,381
Status:
Active
MLS#:
26022505
Type:
Single Family
Subdivision:
Fairholme Estates
Lot size:
0.4 Acres
Year built:
2026
A broker reciprocity listing Courtesy: The Brokerage 859-983-7365
View additional info

ADDITIONAL INFORMATION

Modern luxury meets everyday living in this beautiful new construction ranch home in Winchester's Fairholme Estates- where thoughtful details, timeless finishes, and incredible golf course view sunsets come together effortlessly. Inside, an inviting open-concept layout features vaulted ceilings and a fireplace anchoring the spacious living room. The timeless kitchen is designed to be both beautiful and functional, with quartz countertops, a charming nook perfect for a coffee bar, a spacious walk-in pantry with floating shelves, and a wine cooler. Just off the kitchen, a dedicated dining space with a vaulted ceiling creates the perfect setting for everything from nightly dinners to effortless entertaining. The private primary suite is a true retreat, featuring a spa-like en-suite with a soaking tub, tiled walk-in shower, dual vanities, and a spacious custom closet. A split-bedroom design provides added privacy, with three additional bedrooms and two full bathrooms offering plenty of space for family, guests, or a home office. Step outside to enjoy the covered back patio to relax or entertain with friends and family. And the location? Hard to beat. Just outside charming downtown Winchester, you're minutes from local shops, restaurants, and everything the community has to offer, with quick access to I-64 for an easy commute. The tall garage provides the perfect solution for vertical storage, adding even more functionality to this thoughtfully designed home.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,496
Status:
Active
MLS#:
26019848
Type:
Single Family
Subdivision:
Pilot View
Lot size:
5.58 Acres
Year built:
1984
A broker reciprocity listing Courtesy: Dream Maker Realty, LLC 859-404-3384
View additional info

ADDITIONAL INFORMATION

Discover the perfect blend of privacy, comfort, and country elegance on nearly 6 acres of beautiful Kentucky land. This stunning 4 bedroom, 2.5 bath home offers the lifestyle buyers dream of — complete with a sparkling inground pool, generous outdoor space, and thoughtful updates throughout. Set in a peaceful rural setting yet conveniently located just 8 minutes from the Winchester Bypass and 15 minutes from Mt. Sterling, this property delivers the best of both worlds: tranquility and accessibility. From the inviting living spaces to the expansive grounds ideal for relaxing, entertaining, or simply enjoying the view, this home is truly one of a kind. Opportunities like this don't come often — this one will move fast. Don't miss your chance. Call today to schedule your private showing.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,204
Status:
Active
MLS#:
26019133
Type:
Single Family
Subdivision:
Calmes Estates
Lot size:
0.25 Acres
Year built:
1989
A broker reciprocity listing Courtesy: Dream Maker Realty, LLC 859-404-3384
View additional info

ADDITIONAL INFORMATION

Welcome to this superbly maintained home located in one of the area's most desirable neighborhoods. Offering 11 spacious rooms, this property delivers exceptional comfort, versatility, and charm. A beautiful front wrap around covered porch creates an inviting first impression, perfect for relaxing or greeting guests. The rear of the home features a covered back porch and an adjoining open deck, ideal for outdoor dining, entertaining, or enjoying peaceful evenings. An outbuilding provides valuable additional storage or workspace. Convenience is unmatched—you're just a few minutes from shopping, restaurants, golf courses, and the bypass, making daily living effortless while still enjoying the tranquility of a well established community. This home truly has so much to offer and is a must see for buyers seeking comfort, location, and lifestyle.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,325
Status:
Active
MLS#:
26014834
Type:
Single Family
Subdivision:
Oakmont
Lot size:
0.14 Acres
Year built:
2020
A broker reciprocity listing Courtesy: Ensor Real Estate, LLC 859-749-0892
View additional info

ADDITIONAL INFORMATION

Updated Price, below Apprisal value...Space, Location, and Great Finishes....4 bedrooms, 2.5 bathrooms, walk in sit down and relax...Dining Room/Living Room or Office welcomes you as you enter from the covered front porch. Guests can use the 1/2 bathroom on the main level...Open Kitchen and Family Room with granite counter tops, breakfast bar, and large pantry making cooking easy, 10 ft ceilings on the mail level offer a more open feel. Upstairs you will find a large laundry room 3 bedrooms a guest bathroom with double vanity! The primary bedroom offers plenty of room, double vanity bathroom, and custom walk-in closet. Outside the yard is fenced with vinyl style fencing, a patio for grilling and 2 car attached garage for your vehicles and storage. This home has all the space and it's priced to sell!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,444
Status:
Active
MLS#:
26014053
Type:
Single Family
Subdivision:
Victory Heights
Lot size:
0.15 Acres
Year built:
1999
A broker reciprocity listing Courtesy: Freedom Realty & Property Management 859-771-0777
View additional info

ADDITIONAL INFORMATION

If you love to entertain and are looking for a cozy home that is move in ready, you don't want to let the one pass you by! Includes 3 bedrooms and two full baths this home has it all. Equipped with a primary bedroom suite with spacious bathroom and walk in closet. This home has beautiful hardwood floors in kitchen living and dining areas. In the gallery kitchen you will find granite countertops, new stainless steel dishwasher,refrigerator and stove. Great curb appeal, covered back porch, with privacy fencing, two storage sheds, large driveway, lots of updates throughout and more.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,904
Status:
Active
MLS#:
26014026
Type:
Single Family
Subdivision:
Oakmont
Lot size:
0.09 Acres
Year built:
2009
A broker reciprocity listing Courtesy: Freedom Realty & Property Management 859-771-0777
View additional info

ADDITIONAL INFORMATION

Welcome to this well-maintained home located in a quiet, established neighborhood with convenient access to everything Winchester has to offer. The first floor features an open and inviting layout, creating a comfortable space for everyday living and entertaining alike. Upstairs, you'll find a traditional three-bedroom floor plan with generously sized bedrooms, including a spacious primary suite. Recent updates include a brand-new roof, along with manufactured hardwood flooring installed in the living area, foyer, and primary bedroom. Conveniently located near the Winchester Bypass, this home offers quick access to shopping, dining, and everyday amenities, while also providing easy access to I-64, I-75, Lexington, and the Mountain Parkway for commuters and travelers. Offering a desirable combination of space, updates, and location, this home is ready for its next owner to enjoy. Schedule your private showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,680
Status:
Active
MLS#:
26013935
Type:
Single Family
Subdivision:
Stuarts Addition
Lot size:
0.1 Acres
Year built:
1937
A broker reciprocity listing Courtesy: Ensor Real Estate, LLC 859-749-0892
View additional info

ADDITIONAL INFORMATION

Lovely older home, located witin waking distance to collage park whice offers Pickle Ball, Pool, Tennis, play gound and Walking Trail, also walking distance to Historic Downtown Winchester, with a little love house brings large rooms and a nostlogic atmosphire, take a look, view today, this a a great price for 3 bedrooms, 1 1/2 baths, nice back yard, with parking, call today! Selling "AS IS", inspections welcome, the are no utilties on at the present, Estate Please make sure all doors are locked when you leave, buyer to verifye size of home & Lot

Beds:
3
Baths:
3.00
Sq.Ft.:
1,945
Status:
Active
MLS#:
26013780
Type:
Single Family
Subdivision:
Fairholme Estates
Lot size:
0.11 Acres
Year built:
2024
A broker reciprocity listing Courtesy: RE/MAX Creative, Winchester 859-422-2000
View additional info

ADDITIONAL INFORMATION

Just a 20-second golf cart ride to the Winchester Country Club driving range! Built in 2024 and upgraded throughout, this beautiful 3-bedroom, 2.5-bath home offers modern style, functional living space, and a prime location. The open-concept main level features a spacious living room, kitchen, and dining area designed for both everyday living and entertaining, complete with granite countertops in the kitchen and baths, a deep farmhouse sink, pantry, and stainless appliances. Upstairs, you'll find a generous primary suite with a private bath and walk-in closet, along with two additional bedrooms and a full guest bath. Luxury vinyl plank flooring runs throughout the home, while accent wallpaper in multiple rooms adds warmth, personality, and a custom feel. Recent owner upgrades include a privacy fence, landscape lighting and new shrubs, upgraded stair treads, a concrete sidewalk, and additional attic flooring with a folding attic ladder for convenient storage. The home's attractive exterior combines clean modern lines with shake-style architectural accents, creating great curb appeal. Enjoy nearby golf course views and the convenience of country club living without being directly on the course. Additional features include a 2-car attached garage, crawlspace foundation, and no HOA. With modern construction, quality finishes, and numerous owner-added improvements, this move-in ready home is ready for its next owners to enjoy.

Beds:
4
Baths:
1.00
Sq.Ft.:
1,609
Status:
Active
MLS#:
26013563
Type:
Single Family
Subdivision:
Belair
Lot size:
0.22 Acres
Year built:
1958
A broker reciprocity listing Courtesy: Keller Williams Commonwealth 859-721-2121
View additional info

ADDITIONAL INFORMATION

Nestled in a well-established neighborhood filled with charm and character, this inviting all-brick home offers the warmth and comfort you've been looking for. Featuring 4 bedrooms and 1 bath, the thoughtfully designed layout includes a primary bedroom and second bedroom on the main floor, with two additional bedrooms upstairs, providing flexibility for family, guests, or a home office. Beautiful hardwood floors add timeless character throughout much of the home, while the kitchen is equipped with stainless steel appliances and plenty of space for preparing meals and gathering with loved ones. The solar panels help keep utility costs low, making this home as efficient as it is welcoming. Outside, you'll find a wonderful fenced backyard that feels like a private retreat, complete with a chicken coop, storage shed, and plenty of room for gardening, pets, play, or relaxing evenings outdoors. A 1-car garage provides additional storage and convenience. With its classic all-brick construction, cozy atmosphere, mature surroundings, and practical updates, this home offers a perfect blend of comfort, character, and everyday living in one of Winchester's quaint established neighborhoods.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,050
Status:
Active
MLS#:
26013434
Type:
Single Family
Subdivision:
Forest Park
Lot size:
0.18 Acres
Year built:
1962
A broker reciprocity listing Courtesy: WEICHERT REALTORS - ABG Properties 859-333-7271
View additional info

ADDITIONAL INFORMATION

Welcome to a well maintained 3 bedroom 1 full bath home that has been lovingly cared for by only two owners since 1962. Recent updates include new flooring and completed repairs, makiing this property ready for a new owner, while preserving its timeless character. Beautiful hardwood floors add warmth and charm throughout the home. Enjoy relaxing or entertaining on the comfortable spacious patio perfectly sized for gatherings. The brick fireplace with gas logs, located in the living room, adds a cozy ambience on cool evenings. One of the property's standout features is its prime location backing directly to Legacy Grove Park complete with a private gate providing conveninent park access. This unique setting offers addttiional outdoor space, scenic views and a peaceful atmosphere right in your own backyard. . This is a wonderful opportunity to call a well cared for property with an abundance of charm your very own.

Beds:
4
Baths:
5.00
Sq.Ft.:
4,173
Status:
Active
MLS#:
26013378
Type:
Single Family
Subdivision:
Thomson Addition
Lot size:
0.9 Acres
Year built:
1920
A broker reciprocity listing Courtesy: The Agency 859-285-0614
View additional info

ADDITIONAL INFORMATION

Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the tone for the elegance that flows throughout the home. The formal living room exudes Southern charm, featuring intricate moldings, and large windows that bathe the space in natural light. The formal dining room is perfect for hosting memorable gatherings, with ample space for entertaining in style. Designed for both beauty and function, this home seamlessly blends historic inspiration with modern amenities, creating a warm and inviting atmosphere. Whether you're enjoying a quiet evening on the spacious screened in porch or hosting lavish celebrations, this extraordinary estate is a true embodiment of Southern grace and hospitality. Owner/Agent

Beds:
3
Baths:
2.00
Sq.Ft.:
1,533
Status:
Active
MLS#:
26013350
Type:
Single Family
Subdivision:
Downtown
Lot size:
0.19 Acres
Year built:
1940
A broker reciprocity listing Courtesy: Joyce Marcum Realty 859-624-0088
View additional info

ADDITIONAL INFORMATION

"Motivated sellers—bring your offers!" Step into this charming 3-bedroom, 2-bath home that's full of character and timeless appeal. From the beautiful hardwood floors to the inviting living spaces, this older home offers warmth and personality you simply don't find in newer construction. The spacious living room provides plenty of room to relax or entertain, while the separate dining room is perfect for family meals and special gatherings. The large kitchen offers abundant space for cooking, storage, and everyday living. Outside, you'll enjoy a fully fenced backyard that's ideal for children, pets, gardening, or outdoor entertaining. Sip your morning coffee on the welcoming covered front porch or unwind on the back deck overlooking the private yard. This home offers the perfect combination of classic charm, generous living space, and inviting outdoor areas. All this in a great location, just minutes from Lexington, the horse capital of the world, with beautiful Kentucky horse farms! And just 45 minutes from the famous Red River Gorge! This home is right in the center of it all, city life and the beautiful outdoors! Don't miss this wonderful opportunity to make this charming home your own!

Beds:
2
Baths:
1.00
Sq.Ft.:
849
Status:
Active
MLS#:
26013194
Type:
Single Family
Subdivision:
Rural
Lot size:
5 Acres
Year built:
1996
A broker reciprocity listing Courtesy: WTC Realty LLC 606-344-6560
View additional info

ADDITIONAL INFORMATION

Newly renovated Cabin sitting on +- 5 acres. Renovations began in 2024 and were completed in 2026. An ideal property for a first-time home buyer or anyone looking for a remote quiet location located within 20 minutes of downtown Winchester.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,858
Status:
Active
MLS#:
26013010
Type:
Single Family
Subdivision:
Windridge
Lot size:
0.47 Acres
Year built:
1970
A broker reciprocity listing Courtesy: The Agency 859-285-0614
View additional info

ADDITIONAL INFORMATION

Welcome home to Windridge!!! This beautifully updated all-brick ranch that perfectly blends charm and modern upgrades in a well established, desirable neighborhood is sure to please. Step inside to a bright open-concept living space featuring luxury vinyl flooring, a stunning wood-burning fireplace, and exposed wood ceiling beams that create a warm, inviting atmosphere in the spacious family room. The completely renovated kitchen boasts new cabinetry, gorgeous granite countertops, and new stainless appliances, making it perfect for cooking, entertaining, and everyday living. Enjoy mornings on the covered front porch and evenings in the fenced backyard with a deck, ideal for relaxing or hosting friends and family. If you are looking for low maintenance property, one level living and a home ready to move straight into, look no further! Stylish updates, great outdoor spaces, and a classic all-brick construction, situated on a large corner lot......Don't miss this one!

Beds:
5
Baths:
4.00
Sq.Ft.:
4,456
Status:
Active
MLS#:
26012369
Type:
Single Family
Subdivision:
Downtown
Lot size:
0.52 Acres
Year built:
1945
A broker reciprocity listing Courtesy: Bluegrass Home Group 859-687-1010
View additional info

ADDITIONAL INFORMATION

Whether you're looking for a large residential home, investment opportunity, business potential, or a combination of uses, this property is ready to fit your vision. Featuring 5 bedrooms, 4 baths, soaring 10 foot ceilings, and a welcoming front porch, this unique property blends character, space and versatility. Generous room sizes, timeless charm, and flexible living spaces make it ideal for multi-generational living, rental income opportunities, or for a great work setup. Opportunity with unlimited potential.

Beds:
1
Baths:
2.00
Sq.Ft.:
2,179
Status:
Active
MLS#:
26012322
Type:
Single Family
Subdivision:
Rural
Lot size:
2.5 Acres
Year built:
2020
A broker reciprocity listing Courtesy: RE/MAX Creative Realty 859-422-2000
View additional info

ADDITIONAL INFORMATION

Home listed as one bedroom while unofficially has 3 but 2 of them are interior rooms without windows. ( Owners Now Offering to pay up to $5,000 in closing cost and pre-paids on behalf of buyers). Tired of the honking horns , congested traffic, sirens of town living and dreaming of country living, your own slice of paradise? Maybe raising your own garden , owning chickens , goats, horses , whatever you always dreamed of. Maybe just kicking back on the wrap around porch watching the chickens peck. This really is an amazing property and you will fall in love with all the bells and whistles like the beautiful soaking tub, 2 walk in showers, huge kitchen island, large primary bedroom and bath, stainless steel appliances. It practically a new house , the front portion of the house where the living room , hall, primary bedroom were all built new in 2020 . All the wiring , plumbing , insulation, flooring , drywall has been replaced since 2020. Home is also very conveniently placed just minutes from exit 10 on the Mountain Parkway between, Winchester and Clay City. Dont let anyone beat you to it , this is a real jewel. Porch swing belonged to owners great grandmother and does not convey.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,261
Status:
Active
MLS#:
26011961
Type:
Single Family
Subdivision:
Downtown
Lot size:
0.14 Acres
Year built:
1940
A broker reciprocity listing Courtesy: United Real Estate Bluegrass 859-800-7355
View additional info

ADDITIONAL INFORMATION

Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a beautifully updated kitchen featuring stainless steel appliances, a gas range, pantry, and plenty of space for cooking and entertaining. The home offers a primary suite, two additional bedrooms, an additional full bath, and a large utility room with extra storage and functionality. Outside, the 20x24 detached garage with electric is a rare bonus and ideal for carpentry projects, woodworking, hobbies, a workshop, home gym, storage for recreational equipment, or even the perfect space for car enthusiasts and DIYers. Enjoy small-town charm with quick access to shopping, dining, and interstate travel in this thoughtfully updated property ready for its next owner!

Beds:
3
Baths:
2.00
Sq.Ft.:
915
Status:
Active
MLS#:
26011564
Type:
Single Family
Subdivision:
Buffalo Trace
Lot size:
0.16 Acres
Year built:
1999
A broker reciprocity listing Courtesy: The Brokerage 859-983-7365
View additional info

ADDITIONAL INFORMATION

This move in ready ranch home offering 3 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!

Beds:
3
Baths:
3.00
Sq.Ft.:
4,518
Status:
Active
MLS#:
26011538
Type:
Single Family
Subdivision:
Rural
Lot size:
32.87 Acres
Year built:
1919
A broker reciprocity listing Courtesy: Coldwell Banker McMahan 859-744-1400
View additional info

ADDITIONAL INFORMATION

Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points in Clark County, where you can see the panoramic views stretching all the way to the dormitories at EKU in Richmond and the mountains near Berea, KY. Relax by the newly lined in-ground pool with a new cover, and unwind in the hot tub while taking in the beautiful sunrise and sunset views — perfect for family gatherings or quiet evenings under the stars. The property features a two-level barn with horse stalls, a tack room, and a spacious open arena — ideal for equestrian enthusiasts. The upper level of the barn provides versatile space for auto storage or a workshop, while the fenced pastures and horse ring make it ready for boarding or training horses. This property also includes a stocked pond, adding to the tranquil landscape, and 2 gated driveways with a security system for peace of mind. The land features mature trees, including fig, pear, and apple. This is the first property on Colby Road out of Winchester with agricultural zoning, a very private estate, and the first time in 40 years this remarkable property has been for sale. Conveniently located just one mile to Kroger, Lowe's, and Walmart, and approximately 20 min. from Man O War via Todds Rd. Lexington. This property offers both peaceful seclusion and easy access to amenities. With potential for income from horse boarding and a rental home on the property, this exceptional farm is more than a home- it's a lifestyle, an investment, and a place to create lasting memories for generations to come.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,420
Status:
Active
MLS#:
26011465
Type:
Single Family
Subdivision:
Ash Pointe
Lot size:
0.16 Acres
Year built:
1999
A broker reciprocity listing Courtesy: Coldwell Banker McMahan 859-744-1400
View additional info

ADDITIONAL INFORMATION

Welcome to this delightful 1.5-story home perfectly situated on a spacious corner lot just off the Eastern Bypass and only minutes from I-64. Convenience meets comfort in this beautifully maintained property offering 3 bedrooms, 2 full baths, and an inviting layout designed for everyday living. Step inside to an open living area ideal for entertaining, a spacious kitchen and dining space, and plenty of room for family and friends to gather. Natural light fills the home, creating a warm and welcoming atmosphere throughout. Outside, enjoy an oversized backyard complete with a charming white picket fence — perfect for children, pets, gardening, or hosting outdoor entertaining. Whether you're a first time buyer or searching for your forever home, this property offers comfort, convenience, and character all in one. Call today for more information or to schedule your private showing. Note: Offer to Purchase with Contingency and Kick-out Clause. Buyer cannot perform without the sale of current property.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,680
Status:
Active
MLS#:
26011126
Type:
Single Family
Subdivision:
Rural
Lot size:
10.02 Acres
Year built:
1998
A broker reciprocity listing Courtesy: Dream Maker Realty, LLC 859-404-3384
View additional info

ADDITIONAL INFORMATION

This 3 bedroom 2 bath ranch home is tucked away in a beautiful wooded area of Clark County. It is sitting on over 10 acres of land that would be great for livestock or hunting. It is just minutes from historic downtown Winchester. The property is also a short drive to retail shops, restaurants, and other amenities. Come take a look at the beautiful view from the front porch of this home in the country.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,260
Status:
Active
MLS#:
26011097
Type:
Single Family
Subdivision:
Witherspoon
Lot size:
0.23 Acres
Year built:
1910
A broker reciprocity listing Courtesy: Lois Ann Disponett Real Est 502-839-7409
View additional info

ADDITIONAL INFORMATION

Space, updates, and charm all come together in this spacious 2,260 square foot 1.5-story home located in the heart of Winchester! Recently updated and full of character, this property offers a flexible layout with room for everyone. The main level offers a welcoming living room, large family room, dining area, kitchen, laundry room, full guest bath, and a spacious primary suite complete with a private bath. Upstairs you'll find two additional generously sized bedrooms along with a convenient half bath. Enjoy relaxing mornings on the covered front porch made for rocking chairs or unwind on the covered rear porch overlooking the backyard. Additional features include two carports, storage building, rear drive access, fresh paint, some new flooring, central heat and air, and much more! Don't miss your opportunity to own this move-in ready home with space, updates, and charm throughout. Schedule your showing today! This is a Fannie Mae HomePath property.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,860
Status:
Active
MLS#:
26022399
Type:
Single Family
Subdivision:
Rural
Lot size:
59.1 Acres
Year built:
2015
A broker reciprocity listing Courtesy: The Agency 859-285-0614
View additional info

ADDITIONAL INFORMATION

Welcome to your own slice of Kentucky countryside! Situated on 59.104 picturesque acres, this beautifully maintained 3 bedroom, 2 bath home offers the perfect blend of modern comfort and functional farm living. Built in 2015 with 1,860 sq ft of open-concept living space, the home features soaring ceilings, abundant natural light, a spacious kitchen with oversized island, and a warm, inviting living area ideal for entertaining or relaxing after a day outdoors. The property is thoughtfully equipped for livestock and equestrian use with a horse shed, automatic waterers, multiple fenced areas, 5 additional sheds, and a barn with lean-to for extra storage and shelter. A massive 2,040 sq ft attached garage provides ample room for vehicles, equipment, workshop space, or recreational storage. Whether you're looking for a working farm, horse property, hunting retreat, or peaceful country escape, this property offers endless opportunities with wide-open acreage and beautiful rural views, all while still being conveniently located near town amenities. 4578 Combs Ferry Rd is country living done right.

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51–75 of 110 properties displayed
Andrea D. Conner, License 221773, Xome Inc., License 239054, [email protected], 844-400-XOME (9663), 1795 Alysheba Way, Suite 102, Lexington, KY 40509


The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Lexington Bluegrass Multiple Listing Service. The Broker providing this data believes them to be correct but advises interested parties to confirm them before relying on them in a purchase decision. Copyright 2026 Lexington Bluegrass Multiple Listing Service. All rights reserved.



Winchester Real Estate

Winchester is located in Kentucky. Winchester, Kentucky has a population of 18,993. Winchester is less family-centric than the surrounding county with 25.63% 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 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 is 36.9 years.

Winchester Weather

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.

Winchester Map

Winchester Real Estate Market Conditions

  • Median sales price

    $291,000
    19.3%
    change since last quarter
  • # Active listings

    218
    30-day change

Winchester Schools and Demographics

Education near Winchester, KY

City County
High School Graduates 86.63 89.23
College Degree - 2 year 8.6 9.97
College Degree - 4 year 19.04 20.05
Graduate Degree 4.07 5.81
Expenditures per Student 14,536 14,536
Students per Teacher 13.6 13.6

Elementary Schools near Winchester, KY

Grades Students P/T Ratio ZIP
Athens-Chilesburg Elementary School KG - 05 745 14.9 40509
Camargo Elementary School PK - 04 612 13.2 40353
Clark County Preschool PK - PK 296 24.7 40391
Clay City Elementary School PK - 05 535 16.7 40312
Mapleton Elementary School KG - 04 674 14.7 40353
Montgomery County Early Learning Center PK - PK 109 18.2 40353
Mount Sterling Elementary School KG - 04 635 15.1 40353
North Middletown Elementary School KG - 05 155 14.8 40357
Shearer Elementary School KG - 04 423 12 40391
Strode Station Elementary School KG - 04 613 12.4 40391
William G. Conkwright Elementary KG - 04 563 20 40391
Willis H. Justice Elementary School KG - 04 491 16.2 40391

Middle Schools near Winchester, KY

Grades Students P/T Ratio ZIP
Edythe Jones Hayes Middle School 06 - 08 1,095 15.6 40509
McNabb Middle School 07 - 08 718 16.2 40353
Mercer County 9th Grade Academy 09 - 09 224 16.2 40391
Montgomery County Intermediate School 05 - 06 712 15.6 40353
Rev. Henry E. Baker SR. Interm. School 05 - 06 858 19.5 40391
Robert D. Campbell Jr. High 07 - 08 801 18.2 40391
Willis H. Justice Elementary School KG - 05 0 13.7 40391

High Schools near Winchester, KY

Grades Students P/T Ratio ZIP
George Rogers Clark High School 09 - 12 1,672 18.2 40391
Montgomery County High School 09 - 12 1,338 18.4 40353

Ungraded Schools near Winchester, KY

Grades Students P/T Ratio ZIP
* Gateway Children's Services 07 - 12 18 9 40353
* Hillcrest Hall Treatment Center 09 - 12 12 12 40353
* Phoenix Academy 07 - 12 22 4.4 40391
* The Sterling School 09 - 12 51 11.3 40353
Clark County Area Technology Center UG - UG 0 40392
Hayes Pre-School UG - UG 93 30.5 40509
Montgomery County Accelerated Academy UG - UG 0 40353
Montgomery County Area Technology Center UG - UG 0 40353

Demographics near Winchester, KY

City County
Neighborhood Type Suburban
Population 18,993 36,716
Population Density 2,078 145
Median Age 36.9 41.5
People per Household 2.3 2.5
Median Household Income 47,034 59,294
Average Income per Capita 28,337 33,205

Real estate near Winchester