$1,695,000 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. 3 Beds ⋅ 3 Baths ⋅ 26011538 MLS 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. 3166 Colby Rd, Winchester
$78,500 NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build your New Kentucky Home. The developer is currently finalizing the restrictions so they are not available for distribution. New restrictions will incorporate the following: 80% brick/stone exterior, Roof pitch requirements, Minimum 1,600 sq ft for a ranch, 1800 for a One-Half Level, 2100 Two Story. Development lot sizes require minimum lot is 9000 sq ft and current development plan has the smallest lot at 9600 sqft. Positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 future single-family homes, and additional acreage available for 8 duplexes and 48 townhomes, meeting the region's demand for quality and attainable housing. Phase Two and Three begin in December with 34 buildable lots expected completion by Spring 2026 Approved development plan in place with Clark County. Additional Phases continuously following with additional buildable lots. Located within 20 miles to Lexington's Hamburg area, Deerlawn sits at the center of Clark County's growth corridor. With $100M in infrastructure improvements completed and the EPA Consent Decree lifted in 2024, the path is clear for accelerated residential and economic expansion. 26011488 MLS NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build your New Kentucky Home. The developer is currently finalizing the restrictions so they are not available for distribution. New restrictions will incorporate the following: 80% brick/stone exterior, Roof pitch requirements, Minimum 1,600 sq ft for a ranch, 1800 for a One-Half Level, 2100 Two Story. Development lot sizes require minimum lot is 9000 sq ft and current development plan has the smallest lot at 9600 sqft. Positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 future single-family homes, and additional acreage available for 8 duplexes and 48 townhomes, meeting the region's demand for quality and attainable housing. Phase Two and Three begin in December with 34 buildable lots expected completion by Spring 2026 Approved development plan in place with Clark County. Additional Phases continuously following with additional buildable lots. Located within 20 miles to Lexington's Hamburg area, Deerlawn sits at the center of Clark County's growth corridor. With $100M in infrastructure improvements completed and the EPA Consent Decree lifted in 2024, the path is clear for accelerated residential and economic expansion. Lot 4 Plantations, Winchester
$128,800 This exceptional 2.3 acre homesite offers the perfect canvas to bring your vision to life. With ample space, a prime cul-de-sac setting, and stunning surroundings, it's an ideal opportunity to create the custom home you've always wanted. Located in The Reserve, one of Winchester's premier subdivisions, this property boasts scenic daytime views and unforgettable sunsets each evening. Enjoy the perfect blend of privacy and convenience with quick access to shopping, dining, schools, and I-64. Don't miss your chance to own the largest lot in the neighborhood. Schedule your visit today! 26008587 MLS This exceptional 2.3 acre homesite offers the perfect canvas to bring your vision to life. With ample space, a prime cul-de-sac setting, and stunning surroundings, it's an ideal opportunity to create the custom home you've always wanted. Located in The Reserve, one of Winchester's premier subdivisions, this property boasts scenic daytime views and unforgettable sunsets each evening. Enjoy the perfect blend of privacy and convenience with quick access to shopping, dining, schools, and I-64. Don't miss your chance to own the largest lot in the neighborhood. Schedule your visit today! 110 Knox Ct, Winchester
$329,000 Don't let this charming brick ranch fool you—it's what's waiting out back that will absolutely steal the show! Nestled in the heart of Winchester, this 3BR/3BA home offers an incredible backyard oasis that's perfect for entertaining, relaxing, and making memories all summer long. The sparkling in-ground pool is the centerpiece of this private retreat, surrounded by expansive concrete decking and complemented by a covered pool bar with electricity. An additional freestanding deck provides even more room to relax, while the fixed outdoor movie screen creates unforgettable movie nights from the comfort of your pool float. Gather around the fire pit on cool evenings, shoot hoops on the spacious patio, relax in the hot tub, or enjoy hobbies and extra storage in the outbuilding complete with electricity. The fully fenced backyard truly feels like your own private staycation. Inside, the home offers a comfortable and flexible layout. The fully equipped eat-in kitchen features a breakfast bar with a cozy dining/sitting area with fireplace insert that's perfect for easy cooking and entertaining. The main level includes a private primary suite, an additional bedroom, and a second full bath. The finished walkout basement adds exceptional flexibility with a spacious family room that could easily serve as a third bedroom, a full bath, and a bonus room ideal for a home office, exercise room, hobby space, or even a potential fourth bedroom (no egress). A one-car basement garage provides additional storage and convenience. From the street, this home is modest and unassuming—but step into the backyard and you'll discover one of Winchester's best-kept secrets. If you've been dreaming of a home where every day feels like a vacation with an affordable price tag, this is one you won't want to miss! 3 Beds ⋅ 3 Baths ⋅ 26016008 MLS Don't let this charming brick ranch fool you—it's what's waiting out back that will absolutely steal the show! Nestled in the heart of Winchester, this 3BR/3BA home offers an incredible backyard oasis that's perfect for entertaining, relaxing, and making memories all summer long. The sparkling in-ground pool is the centerpiece of this private retreat, surrounded by expansive concrete decking and complemented by a covered pool bar with electricity. An additional freestanding deck provides even more room to relax, while the fixed outdoor movie screen creates unforgettable movie nights from the comfort of your pool float. Gather around the fire pit on cool evenings, shoot hoops on the spacious patio, relax in the hot tub, or enjoy hobbies and extra storage in the outbuilding complete with electricity. The fully fenced backyard truly feels like your own private staycation. Inside, the home offers a comfortable and flexible layout. The fully equipped eat-in kitchen features a breakfast bar with a cozy dining/sitting area with fireplace insert that's perfect for easy cooking and entertaining. The main level includes a private primary suite, an additional bedroom, and a second full bath. The finished walkout basement adds exceptional flexibility with a spacious family room that could easily serve as a third bedroom, a full bath, and a bonus room ideal for a home office, exercise room, hobby space, or even a potential fourth bedroom (no egress). A one-car basement garage provides additional storage and convenience. From the street, this home is modest and unassuming—but step into the backyard and you'll discover one of Winchester's best-kept secrets. If you've been dreaming of a home where every day feels like a vacation with an affordable price tag, this is one you won't want to miss! 13 Bel Air Dr, Winchester
$289,000 Opportunity awaits at 54 Locust Drive in Wesleyan Park subdivision. This all-brick ranch on a full unfinished basement offers 3 bedrooms, 2 baths, and 1,692 square feet of finished living space, along with an equally spacious basement ready for storage, hobbies, or future possibilities. Built in 1960, this home features hardwood flooring, a 2-car attached garage, and a fenced backyard with a covered patio. The home retains much of its original character and presents an excellent opportunity for a buyer with vision to update the kitchen, baths, and finishes to match their style. With its solid construction, functional layout, and room to make it your own, this property offers a great blend of value, space, and potential at $299,000. 3 Beds ⋅ 2 Baths ⋅ 26007779 MLS Opportunity awaits at 54 Locust Drive in Wesleyan Park subdivision. This all-brick ranch on a full unfinished basement offers 3 bedrooms, 2 baths, and 1,692 square feet of finished living space, along with an equally spacious basement ready for storage, hobbies, or future possibilities. Built in 1960, this home features hardwood flooring, a 2-car attached garage, and a fenced backyard with a covered patio. The home retains much of its original character and presents an excellent opportunity for a buyer with vision to update the kitchen, baths, and finishes to match their style. With its solid construction, functional layout, and room to make it your own, this property offers a great blend of value, space, and potential at $299,000. 54 Locust Dr, Winchester
$350,000 Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, high visibility commercial space with Lexington Avenue frontage and two apartments on the upper level! Each apartment has two bedrooms, one bath. One unit has been recently remodeled, the other has potential for value add. The flexible commercial space contains 3 half baths. Laundry hook-ups in all 3 units! Basement for extra storage room with freight elevator. Two new HVAC units and a new roof within the last 2 years! Approximately 16 parking spaces. All 3 units are currently occupied. 4 Beds ⋅ 5 Baths ⋅ 26010324 MLS Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, high visibility commercial space with Lexington Avenue frontage and two apartments on the upper level! Each apartment has two bedrooms, one bath. One unit has been recently remodeled, the other has potential for value add. The flexible commercial space contains 3 half baths. Laundry hook-ups in all 3 units! Basement for extra storage room with freight elevator. Two new HVAC units and a new roof within the last 2 years! Approximately 16 parking spaces. All 3 units are currently occupied. 502 W Lexington Ave, Winchester
$115,000 Welcome to 25 Oliver Street, an affordable 3 bedroom, 1 bathroom ranch home in Winchester offering a practical blend of charm and investment potential. With 900 sq ft of first-floor living space, this home features a comfortable layout with vinyl flooring and a manageable single-level design that works well for homeowners, renters, or buyers looking to build equity. The unfinished basement with interior and exterior access adds valuable storage, utility space, and future potential. With under-utilized *R-4 Zoning*, an intelligent investor may uncover additional return on investment. The front porch and rear deck create simple outdoor spaces to relax and enjoy. This property offers the everyday essentials buyers look for at an approachable price point. Whether you are searching for a personal home, a rental property, or your next value-add opportunity in Winchester, this Oliver Street home is worth a closer look. 3 Beds ⋅ 1 Baths ⋅ 26014899 MLS Welcome to 25 Oliver Street, an affordable 3 bedroom, 1 bathroom ranch home in Winchester offering a practical blend of charm and investment potential. With 900 sq ft of first-floor living space, this home features a comfortable layout with vinyl flooring and a manageable single-level design that works well for homeowners, renters, or buyers looking to build equity. The unfinished basement with interior and exterior access adds valuable storage, utility space, and future potential. With under-utilized *R-4 Zoning*, an intelligent investor may uncover additional return on investment. The front porch and rear deck create simple outdoor spaces to relax and enjoy. This property offers the everyday essentials buyers look for at an approachable price point. Whether you are searching for a personal home, a rental property, or your next value-add opportunity in Winchester, this Oliver Street home is worth a closer look. 25 Oliver St, Winchester
$329,900 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. 26014051 MLS 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. 410 W Lexington Ave, Winchester
$249,900 Welcome to 10 Chickadee Lane, Winchester, KY—a beautifully updated 3-bedroom, 1-bath ranch offering the perfect combination of modern upgrades, timeless character, and an unbeatable location. If you're searching for a move-in ready home in Winchester, Kentucky, this one deserves a spot at the top of your list. Extensively renovated in 2020, this home provides peace of mind with major improvements already completed, including new windows, exterior doors, roof, gutters, updated lighting, kitchen cabinetry, countertops, upgraded appliances, remodeled bathroom, electrical panel, HVAC system, water heater, and beautifully refinished hardwood floors. Every update was thoughtfully completed to create a home that is both stylish and functional. Since the renovation, the property has continued to improve with the addition of an 8' x 12' storage shed, a privacy fence enclosing the entire backyard, and additional measures taken to help maintain a dry crawlspace, reflecting the pride of ownership and ongoing maintenance throughout. Inside, you'll appreciate the warmth of the refinished hardwood floors, an updated kitchen designed for everyday living, and a bright, comfortable layout that makes this home feel welcoming from the moment you walk in. Outside, the fully fenced backyard provides plenty of space for entertaining, gardening, pets, or simply relaxing in your own private outdoor retreat. Conveniently located in an established neighborhood, 10 Chickadee Lane offers quick access to shopping, dining, schools, parks, and everything Winchester has to offer, while also providing an easy commute to Lexington and surrounding Central Kentucky communities. Natural gas is available at the property; however, the gas line is currently capped and no active meter is installed. Don't miss this opportunity to own a thoughtfully updated ranch home where the major improvements have already been completed for you. Schedule your private showing today! Buyer to verify all aspects of the property, including schools, square footage, utilities, and any information important to the purchase. 3 Beds ⋅ 1 Baths ⋅ 26016217 MLS Welcome to 10 Chickadee Lane, Winchester, KY—a beautifully updated 3-bedroom, 1-bath ranch offering the perfect combination of modern upgrades, timeless character, and an unbeatable location. If you're searching for a move-in ready home in Winchester, Kentucky, this one deserves a spot at the top of your list. Extensively renovated in 2020, this home provides peace of mind with major improvements already completed, including new windows, exterior doors, roof, gutters, updated lighting, kitchen cabinetry, countertops, upgraded appliances, remodeled bathroom, electrical panel, HVAC system, water heater, and beautifully refinished hardwood floors. Every update was thoughtfully completed to create a home that is both stylish and functional. Since the renovation, the property has continued to improve with the addition of an 8' x 12' storage shed, a privacy fence enclosing the entire backyard, and additional measures taken to help maintain a dry crawlspace, reflecting the pride of ownership and ongoing maintenance throughout. Inside, you'll appreciate the warmth of the refinished hardwood floors, an updated kitchen designed for everyday living, and a bright, comfortable layout that makes this home feel welcoming from the moment you walk in. Outside, the fully fenced backyard provides plenty of space for entertaining, gardening, pets, or simply relaxing in your own private outdoor retreat. Conveniently located in an established neighborhood, 10 Chickadee Lane offers quick access to shopping, dining, schools, parks, and everything Winchester has to offer, while also providing an easy commute to Lexington and surrounding Central Kentucky communities. Natural gas is available at the property; however, the gas line is currently capped and no active meter is installed. Don't miss this opportunity to own a thoughtfully updated ranch home where the major improvements have already been completed for you. Schedule your private showing today! Buyer to verify all aspects of the property, including schools, square footage, utilities, and any information important to the purchase. 10 Chickadee Ln, Winchester
$360,000 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. 1 Beds ⋅ 2 Baths ⋅ 26012322 MLS 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. 3359 Trapp-Goffs Corner Rd, Winchester
$169,000 Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is month to month so the tentant is aware they will need to vacate the property before close of sale. 3 Beds ⋅ 1 Baths ⋅ 26008759 MLS Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is month to month so the tentant is aware they will need to vacate the property before close of sale. 175 Magnolia St, Winchester
$550,000 Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy maintenance with luxury vinyl plank flooring throughout the home. The heart of the home is the spacious great room, complete with a cozy gas log fireplace, perfect for gathering with loved ones. The well-appointed kitchen features a large island, ideal for both cooking and entertaining. Additional features on the first floor include a full bathroom, a convenient half bath, and a separate laundry room for added convenience. Step outside onto the back patio and enjoy the fresh air and sunshine. Let's build your dream home and make the Winchester Floor Plan yours! 3 Beds ⋅ 3 Baths ⋅ 24025578 MLS Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy maintenance with luxury vinyl plank flooring throughout the home. The heart of the home is the spacious great room, complete with a cozy gas log fireplace, perfect for gathering with loved ones. The well-appointed kitchen features a large island, ideal for both cooking and entertaining. Additional features on the first floor include a full bathroom, a convenient half bath, and a separate laundry room for added convenience. Step outside onto the back patio and enjoy the fresh air and sunshine. Let's build your dream home and make the Winchester Floor Plan yours! 107 Bella Shae Way, Winchester
$264,900 Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready property offers 4 bedrooms, an updated bathroom, a welcoming living room with a decorative (non-working) fireplace, and a cozy den featuring preserved French doors. The foyer leads to a beautifully painted staircase and second floor, while the spacious dining room and kitchen showcase custom painted cabinetry, stainless steel appliances, and a pantry. A large laundry room doubles as a walk-in closet for added convenience. Enjoy relaxing mornings on the wrap-around front porch with brick accents and composite steps, or unwind on the rear sunporch overlooking a vinyl-fenced yard complete with a patio area perfect for a fire pit and a 10X17 shed. The main bedroom is located on the first floor, with three additional bedrooms and a bonus room upstairs. Thoughtful touches like modern fixtures, fresh paint, exquisite wallpaper, and newly painted wood flooring elevate the entire home. With large rear parking and a prime location in the heart of downtown Winchester, you'll be within walking distance to local shops, dining, and upcoming festivals. The current owner will surely miss the convenience and wonderful neighbors and is confident the next owners will fall in love just as deeply. This is one you have to see! ONE year home warranty to buyer at closing for peace of mind and dishwasher allowance! 4 Beds ⋅ 1 Baths ⋅ 26012319 MLS Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready property offers 4 bedrooms, an updated bathroom, a welcoming living room with a decorative (non-working) fireplace, and a cozy den featuring preserved French doors. The foyer leads to a beautifully painted staircase and second floor, while the spacious dining room and kitchen showcase custom painted cabinetry, stainless steel appliances, and a pantry. A large laundry room doubles as a walk-in closet for added convenience. Enjoy relaxing mornings on the wrap-around front porch with brick accents and composite steps, or unwind on the rear sunporch overlooking a vinyl-fenced yard complete with a patio area perfect for a fire pit and a 10X17 shed. The main bedroom is located on the first floor, with three additional bedrooms and a bonus room upstairs. Thoughtful touches like modern fixtures, fresh paint, exquisite wallpaper, and newly painted wood flooring elevate the entire home. With large rear parking and a prime location in the heart of downtown Winchester, you'll be within walking distance to local shops, dining, and upcoming festivals. The current owner will surely miss the convenience and wonderful neighbors and is confident the next owners will fall in love just as deeply. This is one you have to see! ONE year home warranty to buyer at closing for peace of mind and dishwasher allowance! 162 French Ave, Winchester
$1,149,000 Seller will need 48 Hours to show, This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths, loft/bedroom/full bath upstairs, separate very large kennel, puppy paradise, office, has all the upgrades for shelter & housing, grooming, dog run, this home is must see, call today! Selling ''AS IS'', inspections welcome, 48 hours notice to show this property is 30 minutes to Lexington and close to I-64 , Please do not pet dogs, 3 Beds ⋅ 4 Baths ⋅ 25018600 MLS Seller will need 48 Hours to show, This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths, loft/bedroom/full bath upstairs, separate very large kennel, puppy paradise, office, has all the upgrades for shelter & housing, grooming, dog run, this home is must see, call today! Selling ''AS IS'', inspections welcome, 48 hours notice to show this property is 30 minutes to Lexington and close to I-64 , Please do not pet dogs, 2100 Irvine Rd Unit 40391, Winchester
$699,000 Operated for over 20 years as a physician's office this two-story building features a "ready to go" office on the main floor with two large apartments on the second floor with walkup, outside entry. The entire structure is on an unfinished basement perfect for storage and access to the mechanical systems. There is also a detached 3-bay garage for parking and storage as well as an asphalt parking lot with more room for more than 25 vehicles. 26004697 MLS Operated for over 20 years as a physician's office this two-story building features a "ready to go" office on the main floor with two large apartments on the second floor with walkup, outside entry. The entire structure is on an unfinished basement perfect for storage and access to the mechanical systems. There is also a detached 3-bay garage for parking and storage as well as an asphalt parking lot with more room for more than 25 vehicles. 218 S Maple St, Winchester
$2,999,000 Some properties are special simply because of the story behind them. This 150 acre farm with 3,168 feet of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function to the farm, while four barns and two storage sheds make it ready for cattle, horses, or anyone wanting a true working farm. There are two homes on the property, offering flexibility for extended family, guests, or farm operations. Whether you dream of continuing its farming legacy, creating a private retreat, or investing in a truly special piece of Kentucky land, this is the kind of place that rarely becomes available. Opportunities like this don't come around often. This farm has been part of one family's story for over two centuries, now it's ready for its next chapter. 6 Beds ⋅ 5 Baths ⋅ 25507353 MLS Some properties are special simply because of the story behind them. This 150 acre farm with 3,168 feet of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function to the farm, while four barns and two storage sheds make it ready for cattle, horses, or anyone wanting a true working farm. There are two homes on the property, offering flexibility for extended family, guests, or farm operations. Whether you dream of continuing its farming legacy, creating a private retreat, or investing in a truly special piece of Kentucky land, this is the kind of place that rarely becomes available. Opportunities like this don't come around often. This farm has been part of one family's story for over two centuries, now it's ready for its next chapter. 3049 Ironworks Rd, Winchester
$78,500 NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build your New Kentucky Home. The developer is currently finalizing the restrictions so they are not available for distribution. New restrictions will incorporate the following: 80% brick/stone exterior, Roof pitch requirements, Minimum 1,600 sq ft for a ranch, 1800 for a One-Half Level, 2100 Two Story. Development lot sizes require minimum lot is 9000 sq ft and current development plan has the smallest lot at 9600 sqft. Positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 future single-family homes, and additional acreage available for 8 duplexes and 48 townhomes, meeting the region's demand for quality and attainable housing. Phase Two and Three begin in December with 34 buildable lots expected completion by Spring 2026 Approved development plan in place with Clark County. Additional Phases continuously following with additional buildable lots. Located within 20 miles to Lexington's Hamburg area, Deerlawn sits at the center of Clark County's growth corridor. With $100M in infrastructure improvements completed and the EPA Consent Decree lifted in 2024, the path is clear for accelerated residential and economic expansion. 26011487 MLS NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build your New Kentucky Home. The developer is currently finalizing the restrictions so they are not available for distribution. New restrictions will incorporate the following: 80% brick/stone exterior, Roof pitch requirements, Minimum 1,600 sq ft for a ranch, 1800 for a One-Half Level, 2100 Two Story. Development lot sizes require minimum lot is 9000 sq ft and current development plan has the smallest lot at 9600 sqft. Positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 future single-family homes, and additional acreage available for 8 duplexes and 48 townhomes, meeting the region's demand for quality and attainable housing. Phase Two and Three begin in December with 34 buildable lots expected completion by Spring 2026 Approved development plan in place with Clark County. Additional Phases continuously following with additional buildable lots. Located within 20 miles to Lexington's Hamburg area, Deerlawn sits at the center of Clark County's growth corridor. With $100M in infrastructure improvements completed and the EPA Consent Decree lifted in 2024, the path is clear for accelerated residential and economic expansion. Lot 3 Plantations, Winchester
$499,900 One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home! 4 Beds ⋅ 3 Baths ⋅ 26010312 MLS One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home! 16 Manor Dr, Winchester
$825,000 Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. The spacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a cozy breakfast nook. The luxurious primary suite offers a private retreat with an ensuite bathroom and a walk-in closet. Every bedroom in this home features a walk-in closet, providing ample storage space for the whole family. Additional features on the first floor include a formal dining room, a dedicated study perfect for working from home, a half bath for guests, and an additional full bathroom. This desirable lot also includes an unfinished walkout basement, offering endless possibilities for expansion or customization. Make the Park Place your dream home. Reach out today to schedule a consultation with our experienced team and bring your vision to life. 3 Beds ⋅ 3 Baths ⋅ 24025579 MLS Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. The spacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a cozy breakfast nook. The luxurious primary suite offers a private retreat with an ensuite bathroom and a walk-in closet. Every bedroom in this home features a walk-in closet, providing ample storage space for the whole family. Additional features on the first floor include a formal dining room, a dedicated study perfect for working from home, a half bath for guests, and an additional full bathroom. This desirable lot also includes an unfinished walkout basement, offering endless possibilities for expansion or customization. Make the Park Place your dream home. Reach out today to schedule a consultation with our experienced team and bring your vision to life. 111 Bella Shae Way, Winchester
$150,000 Parcel 4 in the photos. This 2.774 acre lot is available on Colby Road just 1.5 miles from the Winchester Bypass. No building restrictions other than no manufactured housing and a paved driveway must be completed within a year of finishing a residence. 26008075 MLS Parcel 4 in the photos. This 2.774 acre lot is available on Colby Road just 1.5 miles from the Winchester Bypass. No building restrictions other than no manufactured housing and a paved driveway must be completed within a year of finishing a residence. 3385 Colby Rd, Winchester
$670,000 Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen island, and a generous walk-in pantry, along with a convenient butler's pantry for added storage and prep space. Nine-foot ceilings and luxury vinyl plank flooring throughout add a touch of elegance, while the separate utility room offers practicality. The additional two bedrooms also include walk-in closets. With a formal dining room, unfinished walkout basement, and a two-car garage, this home combines stunning curb appeal with modern functionality. Come build your dream home in Mallard Cove neighborhood! 3 Beds ⋅ 2 Baths ⋅ 24025580 MLS Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen island, and a generous walk-in pantry, along with a convenient butler's pantry for added storage and prep space. Nine-foot ceilings and luxury vinyl plank flooring throughout add a touch of elegance, while the separate utility room offers practicality. The additional two bedrooms also include walk-in closets. With a formal dining room, unfinished walkout basement, and a two-car garage, this home combines stunning curb appeal with modern functionality. Come build your dream home in Mallard Cove neighborhood! 113 Bella Shae Way, Winchester
$110,000 Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home. 22024065 MLS Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home. 120 Duclair Dr, Winchester
$349,900 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! 4 Beds ⋅ 3 Baths ⋅ 26014834 MLS 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! 119 Gibson Way, Winchester
$137,500 Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it grows in value. Offering unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own prime land with unmatched potential 26006848 MLS Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it grows in value. Offering unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own prime land with unmatched potential 150 Spencer Ln, Winchester
$1,850,000 17.87 Acre farm available for sale. Ideal location for redevelopment. Gently rolling topography. Corner lot with excellent visibility. Water, electric, sewer, gas and telecommunications available. Conveniently located near RD Campbell Junior High School, George Rogers Clark High School & Winchester Country Club. Located 3 miles south of Interstate 64. Signalized corner lot at Boonesboro Rd. & Bypass Rd. Easily accessible to nearby retailers, restaurants & residential. Winchester is the county seat of Clark County, KY. This growing city is part of the Lexington-Fayette, KY MSA. Local employers include Amazon, Ale-8-One, and Alltech. 20101924 MLS 17.87 Acre farm available for sale. Ideal location for redevelopment. Gently rolling topography. Corner lot with excellent visibility. Water, electric, sewer, gas and telecommunications available. Conveniently located near RD Campbell Junior High School, George Rogers Clark High School & Winchester Country Club. Located 3 miles south of Interstate 64. Signalized corner lot at Boonesboro Rd. & Bypass Rd. Easily accessible to nearby retailers, restaurants & residential. Winchester is the county seat of Clark County, KY. This growing city is part of the Lexington-Fayette, KY MSA. Local employers include Amazon, Ale-8-One, and Alltech. 1509 Boonesboro Rd, Winchester
$1,200,000 You won't want to miss adding this income-producing apartment complex to your portfolio. This property is comprised of 16 one-bedroom/one-bathroom apartments with 100% occupancy. Complex is conveniently located in downtown Winchester and only 20 minutes from Lexington via easy highway access. The building sits on a 0.34 acre lot with 20+ parking spaces. Property has several updates including roof replacement in 2022, new siding in 2023, and 6 of the AC units were replaced in the last three years. The main electrical service mast was replaced in 2023, and all 100-amp breakers were replaced in 2025. Most units have been updated with LVP flooring. 16 Beds ⋅ 16 Baths ⋅ 26007993 MLS You won't want to miss adding this income-producing apartment complex to your portfolio. This property is comprised of 16 one-bedroom/one-bathroom apartments with 100% occupancy. Complex is conveniently located in downtown Winchester and only 20 minutes from Lexington via easy highway access. The building sits on a 0.34 acre lot with 20+ parking spaces. Property has several updates including roof replacement in 2022, new siding in 2023, and 6 of the AC units were replaced in the last three years. The main electrical service mast was replaced in 2023, and all 100-amp breakers were replaced in 2025. Most units have been updated with LVP flooring. 16 Linden Ave, Winchester
$110,000 Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home. 22024114 MLS Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home. 125 Jacob Ct, Winchester
$221,500 MOTIVATED SELLER!! Don't miss this wonderful home offering convenience, comfort, and value!! Ideally situated near shopping, dining, schools, churches and everyday amenities. This property is perfect for first-time buyers or downsizers. The backyard provides ample space for entertaining is completely fenced in for children and pets. Home also provides room to grow. The attic space has plenty of room to add another bedroom and full bath if desired. Current owner has a formal dining room, the area could be used for a 3rd bedroom in the main living area. In addition to all the potential this property has it also offers lots of updates: New Roof, New Heating & Cooling system, New Windows, and all New Plumbing. If you're looking for a place to call home this one is loaded with charm and busting with potential!! Schedule your showing today!! 2 Beds ⋅ 1 Baths ⋅ 26013551 MLS MOTIVATED SELLER!! Don't miss this wonderful home offering convenience, comfort, and value!! Ideally situated near shopping, dining, schools, churches and everyday amenities. This property is perfect for first-time buyers or downsizers. The backyard provides ample space for entertaining is completely fenced in for children and pets. Home also provides room to grow. The attic space has plenty of room to add another bedroom and full bath if desired. Current owner has a formal dining room, the area could be used for a 3rd bedroom in the main living area. In addition to all the potential this property has it also offers lots of updates: New Roof, New Heating & Cooling system, New Windows, and all New Plumbing. If you're looking for a place to call home this one is loaded with charm and busting with potential!! Schedule your showing today!! 2 Western Ave, Winchester
$139,900 3BR/1BA | Winchester, KY Affordable single-family homes are hard to come by at this price — here's your chance. This cozy 3-bedroom, 1-bath home in Winchester sits on a generous lot with a large backyard, long driveway with plenty of parking, a welcoming covered front porch, and accessible front entry with both steps and a ramp. it's efficient and easy to maintain — and don't let the square footage fool you. A huge walk-in crawl space underneath the home offers exceptional storage that most homes twice the size don't have. The big-ticket items are handled: a brand new roof was installed in 2024, giving you peace of mind for years to come. Currently tenant occupied — ideal for an investor looking for immediate cash flow, or a future owner-occupant planning ahead. 3 Beds ⋅ 1 Baths ⋅ 26007798 MLS 3BR/1BA | Winchester, KY Affordable single-family homes are hard to come by at this price — here's your chance. This cozy 3-bedroom, 1-bath home in Winchester sits on a generous lot with a large backyard, long driveway with plenty of parking, a welcoming covered front porch, and accessible front entry with both steps and a ramp. it's efficient and easy to maintain — and don't let the square footage fool you. A huge walk-in crawl space underneath the home offers exceptional storage that most homes twice the size don't have. The big-ticket items are handled: a brand new roof was installed in 2024, giving you peace of mind for years to come. Currently tenant occupied — ideal for an investor looking for immediate cash flow, or a future owner-occupant planning ahead. 19 3rd St, Winchester
$1,750,000 101 S. Main Street is a fully-restored historic Opera House in the heart of Downtown Winchester. Now functioning in a multiple use capacity, including gallery space, 7-years-running successful restaurant space, wedding event and reception space, and office space. No detail was overlooked in this extensive renovation, now inclusive of multiple commercial kitchens, interior elevator, gracious entertainment spaces, and an abundance of old-world charm through hardwood floors, large windows, exposed brick, and functioning fireplaces. In fact, the Opera House renovations earned the Clyde Carpenter Adaptive Reuse Award from the Bluegrass Trust Historic Preservation Comm. This offering is extremely flexible in that a new owner can step in and operate the same uses already in place, including Lease Back potential from Loma's which is owner occupied, or use the flexible layouts for its own preferences. It is also in the Opportunity Zone, and Downtown Winchester KY offers numerous grants for both renovations and business development should a buyer wish to participate. *Business purchase is not included in the real estate offering. Property Highlights: -Home of the successful and delicious Loma's at the Opera House restaurant and bar, and The Winchester Opera House Ballroom -Ideally located in the heart of Downtown Winchester -The property benefits from the City of Winchester's investment in neighboring High Side Improvement Project with included $5.5 million invested in new angled parking, new sidewalks and added ramps, making the downtown area more accessible as well as 13 new high-end apartments with 10 more in development. 23021742 MLS 101 S. Main Street is a fully-restored historic Opera House in the heart of Downtown Winchester. Now functioning in a multiple use capacity, including gallery space, 7-years-running successful restaurant space, wedding event and reception space, and office space. No detail was overlooked in this extensive renovation, now inclusive of multiple commercial kitchens, interior elevator, gracious entertainment spaces, and an abundance of old-world charm through hardwood floors, large windows, exposed brick, and functioning fireplaces. In fact, the Opera House renovations earned the Clyde Carpenter Adaptive Reuse Award from the Bluegrass Trust Historic Preservation Comm. This offering is extremely flexible in that a new owner can step in and operate the same uses already in place, including Lease Back potential from Loma's which is owner occupied, or use the flexible layouts for its own preferences. It is also in the Opportunity Zone, and Downtown Winchester KY offers numerous grants for both renovations and business development should a buyer wish to participate. *Business purchase is not included in the real estate offering. Property Highlights: -Home of the successful and delicious Loma's at the Opera House restaurant and bar, and The Winchester Opera House Ballroom -Ideally located in the heart of Downtown Winchester -The property benefits from the City of Winchester's investment in neighboring High Side Improvement Project with included $5.5 million invested in new angled parking, new sidewalks and added ramps, making the downtown area more accessible as well as 13 new high-end apartments with 10 more in development. 101 S Main, Winchester