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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!

3 Beds ⋅ 2 Baths ⋅ 26011961 MLS

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!

14 Cook Ave, Winchester

$357,000

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.

3 Beds ⋅ 3 Baths ⋅ 26013780 MLS

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.

309 Gallahadion Ct, Winchester

$399,900

Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a wooded area. The 2 car garage is right off the kitchen allowing for easy accessibility to bring your groceries in. The primary is on the first floor and has an en-suite with a separate sink area from the shower and toilet. There are two other bedrooms and another full bath on the first floor for guests. In the basement you will find the family room and another gas fireplace. There is enough room to have one corner of the basement be an office if needed. You will also find another half bath and utility room on the lower level. The back side of the basement has a large unfinished area with tons of possibilities. The basement family room has walk up/walk out access to the back yard patio where you will find an above ground pool, greenhouse, play set and trampoline (all can be conveyed if needed).

3 Beds ⋅ 3 Baths ⋅ 26009517 MLS

Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a wooded area. The 2 car garage is right off the kitchen allowing for easy accessibility to bring your groceries in. The primary is on the first floor and has an en-suite with a separate sink area from the shower and toilet. There are two other bedrooms and another full bath on the first floor for guests. In the basement you will find the family room and another gas fireplace. There is enough room to have one corner of the basement be an office if needed. You will also find another half bath and utility room on the lower level. The back side of the basement has a large unfinished area with tons of possibilities. The basement family room has walk up/walk out access to the back yard patio where you will find an above ground pool, greenhouse, play set and trampoline (all can be conveyed if needed).

20 Edgewood Dr, Winchester

$165,000

Welcome to this charming river front house. Step out your back door and you are immediately at the river. Open floor plan with a wood burning fireplace. Metal cabinets and epoxy floors on the first level are designed to survive in case of a flood. First floor bedroom with enough room for a King sized bed. Upstairs you will find another bedroom and a half bath. Sip your morning coffee on your back patio area or deck over looking the Kentucky River. There is a large carport for your truck and enough room for a boat as well. The large lot will accommodate a fire pit where you can gather with friends and family. This property is in a flood zone. This property was used as a rental and an air b&b. Make it your own or rent it out, the possibilities are endless.

2 Beds ⋅ 2 Baths ⋅ 26001738 MLS

Welcome to this charming river front house. Step out your back door and you are immediately at the river. Open floor plan with a wood burning fireplace. Metal cabinets and epoxy floors on the first level are designed to survive in case of a flood. First floor bedroom with enough room for a King sized bed. Upstairs you will find another bedroom and a half bath. Sip your morning coffee on your back patio area or deck over looking the Kentucky River. There is a large carport for your truck and enough room for a boat as well. The large lot will accommodate a fire pit where you can gather with friends and family. This property is in a flood zone. This property was used as a rental and an air b&b. Make it your own or rent it out, the possibilities are endless.

1494 Amster Grove Rd Rd, Winchester

$229,000

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.

3 Beds ⋅ 1 Baths ⋅ 26013434 MLS

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.

30 Virginia Ave, Winchester

$189,900

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!

3 Beds ⋅ 2 Baths ⋅ 26011564 MLS

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!

225 Buffalo Trce, Winchester

$74,950

Freshly cleaned and ready for its next owner, this property offers exceptional potential. The spacious 1,800 sq. ft. block garage provides a solid foundation for countless uses — from a workshop or storage facility to a future business or hobby space. An older trailer is also located on the property. It will require a full renovation or removal, giving you the freedom to redesign the space exactly as you envision. Whether you're looking for a project, investment opportunity, or a versatile property with room to grow, this location delivers endless possibilities.

2 Beds ⋅ 1 Baths ⋅ 26004497 MLS

Freshly cleaned and ready for its next owner, this property offers exceptional potential. The spacious 1,800 sq. ft. block garage provides a solid foundation for countless uses — from a workshop or storage facility to a future business or hobby space. An older trailer is also located on the property. It will require a full renovation or removal, giving you the freedom to redesign the space exactly as you envision. Whether you're looking for a project, investment opportunity, or a versatile property with room to grow, this location delivers endless possibilities.

1860 Ford Rd, Winchester

$379,000

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!

4 Beds ⋅ 3 Baths ⋅ 26015608 MLS

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!

107 Hibiscus Ln, Winchester

$325,000

Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make a house a home. Out back, the large, lush yard provides a peaceful setting with plenty of space to gather, garden, or unwind. Inside, the main level offers generous and flexible living space, including a first-floor bedroom, formal living room, den, dining room, kitchen, full bath, and utility area. The standout sunroom is a bright and airy retreat, heated and cooled, with vaulted ceilings, skylights, and beautiful views of the backyard year-round. Upstairs features three bedrooms and a full bath, continuing the home's classic layout (note: no central heat and air on the second floor). An oversized one-car attached garage and ample driveway parking add everyday practicality, something not often found in homes of this era. Being offered as an estate sale, this home has been lovingly cared for over the years and reflects a lifetime of memories. It now awaits its next chapter, someone who will appreciate its history, honor its character, and bring new vision to what it can become.

4 Beds ⋅ 2 Baths ⋅ 26008225 MLS

Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make a house a home. Out back, the large, lush yard provides a peaceful setting with plenty of space to gather, garden, or unwind. Inside, the main level offers generous and flexible living space, including a first-floor bedroom, formal living room, den, dining room, kitchen, full bath, and utility area. The standout sunroom is a bright and airy retreat, heated and cooled, with vaulted ceilings, skylights, and beautiful views of the backyard year-round. Upstairs features three bedrooms and a full bath, continuing the home's classic layout (note: no central heat and air on the second floor). An oversized one-car attached garage and ample driveway parking add everyday practicality, something not often found in homes of this era. Being offered as an estate sale, this home has been lovingly cared for over the years and reflects a lifetime of memories. It now awaits its next chapter, someone who will appreciate its history, honor its character, and bring new vision to what it can become.

443 S Maple St, Winchester

$258,900

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.

2 Beds ⋅ 1 Baths ⋅ 26013194 MLS

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.

955 Right Angle Rd, Winchester

$239,000

Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

4 Beds ⋅ 4 Baths ⋅ 26000922 MLS

Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

1128-1130 Dale Dr, Winchester

$310,000

Welcome to this beautiful BRAND NEW HOME in downtown Winchester! The open-concept design flows into a gorgeous kitchen w/granite countertops, gas stove, stainless appliances, and lots of cabinets. A first-floor bedroom w/private bath offers convenience flexibility. Upstairs, you'll find three generously sized bedrooms, each w/large closets, plus motion-activated hallway lighting. A covered back porch is the perfect spot to relax or entertain.

4 Beds ⋅ 3 Baths ⋅ 26009835 MLS

Welcome to this beautiful BRAND NEW HOME in downtown Winchester! The open-concept design flows into a gorgeous kitchen w/granite countertops, gas stove, stainless appliances, and lots of cabinets. A first-floor bedroom w/private bath offers convenience flexibility. Upstairs, you'll find three generously sized bedrooms, each w/large closets, plus motion-activated hallway lighting. A covered back porch is the perfect spot to relax or entertain.

38 N Burns Ave, Winchester

$275,000

Simply the Best! 3 Bedroom, 1 1/2 bath All Brick ranch home located within walking distance to historic downtown Winchester, Country Club, Middle School, great place to live, you will spend most of your time on the Sunporch off the Kitchen, large lot, many updates, floor, bathrooms, new furnace, fresh paint, don't miss looking at this jewel, call today

3 Beds ⋅ 2 Baths ⋅ 26007260 MLS

Simply the Best! 3 Bedroom, 1 1/2 bath All Brick ranch home located within walking distance to historic downtown Winchester, Country Club, Middle School, great place to live, you will spend most of your time on the Sunporch off the Kitchen, large lot, many updates, floor, bathrooms, new furnace, fresh paint, don't miss looking at this jewel, call today

103 Southern Ct, Winchester

$143,900

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

3 Beds ⋅ 2 Baths ⋅ 26013935 MLS

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

65 Fitch Ave, Winchester

$155,000

Welcome Home! Located across the street from a park with walking trails and 2 dog runs, this home is ready for a new owner. Featuring 2 bedrooms on the first floor and an optional 3rd bedroom or bonus room in the partially finished attic space. The original hardwood floors are located throughout the home. Home features a newer roof and gutters as well as a large fenced backyard. Schedule your private tour today!

2 Beds ⋅ 1 Baths ⋅ 26008307 MLS

Welcome Home! Located across the street from a park with walking trails and 2 dog runs, this home is ready for a new owner. Featuring 2 bedrooms on the first floor and an optional 3rd bedroom or bonus room in the partially finished attic space. The original hardwood floors are located throughout the home. Home features a newer roof and gutters as well as a large fenced backyard. Schedule your private tour today!

13 Maryland Ave, Winchester

$264,900

**Don't miss this exciting opportunity to pick out the new flooring for the basement and kitchen with a full price offer.****New roof (8 months old), one year old AC and heating unit, new large storage shed, and one year old wooden fence All of the expensive upgrades have been done. Come make this home your own. All-brick ranch with a full walk-out basement! This charming home offers excellent potential for the right buyer. The main level features three bedrooms, a full bath, a comfortable living room, and an eat-in kitchen. The walk-out basement expands the living space with two additional bedrooms, full bath, family room with a kitchenette area, utility room, and ample storage with built-in shelving. Step outside to a spacious backyard, fully enclosed with a wooden fence, perfect for pets, play, or outdoor enjoyment.

5 Beds ⋅ 2 Baths ⋅ 26004166 MLS

**Don't miss this exciting opportunity to pick out the new flooring for the basement and kitchen with a full price offer.****New roof (8 months old), one year old AC and heating unit, new large storage shed, and one year old wooden fence All of the expensive upgrades have been done. Come make this home your own. All-brick ranch with a full walk-out basement! This charming home offers excellent potential for the right buyer. The main level features three bedrooms, a full bath, a comfortable living room, and an eat-in kitchen. The walk-out basement expands the living space with two additional bedrooms, full bath, family room with a kitchenette area, utility room, and ample storage with built-in shelving. Step outside to a spacious backyard, fully enclosed with a wooden fence, perfect for pets, play, or outdoor enjoyment.

55 Hillcrest Dr, Winchester