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Convenient, comfortable, and ready for its next owner! This 3-bedroom, 1-bath ranch home is located in the heart of Winchester and offers easy one-level living with a low-maintenance floor plan. Inside, you'll find comfortable living spaces with freshly cleaned carpets and a home that's ready to move into and make your own. A newer roof provides added peace of mind, while the fenced backyard offers plenty of space for pets, kids, entertaining, or simply enjoying the outdoors. One of the property's best features is the detached 2-car garage with electric, providing excellent space for parking, storage, a workshop, or hobbies. With its central Winchester location, fenced backyard, oversized garage space, and manageable one-level layout, 26 Holiday Road is a great opportunity for a first-time buyer, someone looking to downsize, or anyone searching for an affordable, low-maintenance home. Schedule your private showing today!

3 Beds ⋅ 1 Baths ⋅ 26028523 MLS

Convenient, comfortable, and ready for its next owner! This 3-bedroom, 1-bath ranch home is located in the heart of Winchester and offers easy one-level living with a low-maintenance floor plan. Inside, you'll find comfortable living spaces with freshly cleaned carpets and a home that's ready to move into and make your own. A newer roof provides added peace of mind, while the fenced backyard offers plenty of space for pets, kids, entertaining, or simply enjoying the outdoors. One of the property's best features is the detached 2-car garage with electric, providing excellent space for parking, storage, a workshop, or hobbies. With its central Winchester location, fenced backyard, oversized garage space, and manageable one-level layout, 26 Holiday Road is a great opportunity for a first-time buyer, someone looking to downsize, or anyone searching for an affordable, low-maintenance home. Schedule your private showing today!

26 Holiday Rd, Winchester

$255,000

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.

3 Beds ⋅ 3 Baths ⋅ 26011097 MLS

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.

209 Boone Ave, Winchester

$250,000

Welcome to 13 Euclid, a rare find that keeps the original charm of an older downtown home without the upkeep that usually comes with one. This beautiful one-level, 3-bedroom, 2-bath home still has its character, including soaring 12-foot ceilings and original features. Both full bathrooms have been updated, and a fresh neutral color palette runs throughout. Most importantly, the systems and functional items have been updated, allowing for a more maintenance-free lifestyle, which is truly rare in an older home. The home has a dimensional shingle roof, HVAC, water heater, and sewer line that have all been updated within the past five years. The crawlspace vapor barrier and extra attic insulation were updated as well. Low-maintenance white vinyl siding and 200-amp electrical service complete the impressive improvements. A covered front porch welcomes you into the formal foyer, which is flanked by two bedrooms. One is currently used as a sitting area. From the foyer, you'll flow into the living room and adjacent dining room. Just off the dining space, the primary bedroom has a large closet and a private bath. The spacious kitchen is the heart of the home, equipped with all appliances, and a perfect setting for holiday meals. A home office is ready for working from home, and a mudroom and a large laundry room/pantry add everyday convenience. Step outside to the park-like backyard, which is fully fenced with large mature trees, a wide gate, and a parking pad. It's a gardener's dream, with daffodils, tulips, hyacinths, daylilies, and more blooming through the seasons. Park off the rear lane behind the home or on the street out front for easy access. Please note: All updates per seller, and there are 3 beautiful fireplaces in the home for aesthetic purposes only (non-functional).

3 Beds ⋅ 2 Baths ⋅ 26028494 MLS

Welcome to 13 Euclid, a rare find that keeps the original charm of an older downtown home without the upkeep that usually comes with one. This beautiful one-level, 3-bedroom, 2-bath home still has its character, including soaring 12-foot ceilings and original features. Both full bathrooms have been updated, and a fresh neutral color palette runs throughout. Most importantly, the systems and functional items have been updated, allowing for a more maintenance-free lifestyle, which is truly rare in an older home. The home has a dimensional shingle roof, HVAC, water heater, and sewer line that have all been updated within the past five years. The crawlspace vapor barrier and extra attic insulation were updated as well. Low-maintenance white vinyl siding and 200-amp electrical service complete the impressive improvements. A covered front porch welcomes you into the formal foyer, which is flanked by two bedrooms. One is currently used as a sitting area. From the foyer, you'll flow into the living room and adjacent dining room. Just off the dining space, the primary bedroom has a large closet and a private bath. The spacious kitchen is the heart of the home, equipped with all appliances, and a perfect setting for holiday meals. A home office is ready for working from home, and a mudroom and a large laundry room/pantry add everyday convenience. Step outside to the park-like backyard, which is fully fenced with large mature trees, a wide gate, and a parking pad. It's a gardener's dream, with daffodils, tulips, hyacinths, daylilies, and more blooming through the seasons. Park off the rear lane behind the home or on the street out front for easy access. Please note: All updates per seller, and there are 3 beautiful fireplaces in the home for aesthetic purposes only (non-functional).

13 Euclid Ave, Winchester

$249,900

UPDATE: ADDITIONAL PARCEL ADDED. Along with the description below, seller is including 513 N Main which has some buildings in need of repair (thus they were not added to the total square footage). Buy and repair the buildings, or demo the buildings and create additional parking. Has your small business officially outgrown the garage, basement, spare bedroom- or possibly all three? It might be time for a space of its own! This versatile property offers approximately 550 square feet of finished office space plus approximately 1100 square feet of shop/warehouse space. The office area gives you plenty of flexibility for a private office, reception/waiting area, additional workspace or storage, plus one restroom. Out back, the shop/warehouse is ready to work with a gas heater, new LED lighting and two 14' x 14' overhead doors with openers- perfect for vehicles, equipment, inventory or whatever your business needs to keep moving. Most of the work has already been done for you! You'll find fresh paint inside and out, new flooring throughout, and a brand-new blacktop parking lot. Convenient to I-64, Lexington and surrounding Central Kentucky communities, this could be a great fit for a contractor, service-based business or small business owner who simply needs more room to work, store, and grow. Because eventually, your kitchen table would probably like to go back to just being a kitchen table. Listing agent is related to seller.

26027255 MLS

UPDATE: ADDITIONAL PARCEL ADDED. Along with the description below, seller is including 513 N Main which has some buildings in need of repair (thus they were not added to the total square footage). Buy and repair the buildings, or demo the buildings and create additional parking. Has your small business officially outgrown the garage, basement, spare bedroom- or possibly all three? It might be time for a space of its own! This versatile property offers approximately 550 square feet of finished office space plus approximately 1100 square feet of shop/warehouse space. The office area gives you plenty of flexibility for a private office, reception/waiting area, additional workspace or storage, plus one restroom. Out back, the shop/warehouse is ready to work with a gas heater, new LED lighting and two 14' x 14' overhead doors with openers- perfect for vehicles, equipment, inventory or whatever your business needs to keep moving. Most of the work has already been done for you! You'll find fresh paint inside and out, new flooring throughout, and a brand-new blacktop parking lot. Convenient to I-64, Lexington and surrounding Central Kentucky communities, this could be a great fit for a contractor, service-based business or small business owner who simply needs more room to work, store, and grow. Because eventually, your kitchen table would probably like to go back to just being a kitchen table. Listing agent is related to seller.

506-513 N Main St, Winchester

$249,900

Welcome to 317 Vanover Way! This beautiful, well-maintained 3-bedroom, 2-bath home is move-in ready and waiting for its next owner. Step inside to a spacious living room with the bedrooms conveniently located just off the main living area. Coming in from the garage, you'll find a functional mudroom and laundry area that leads directly into the kitchen. Outside, enjoy a nice-sized fenced backyard and a deck that's perfect for entertaining, relaxing, or enjoying time outdoors. A comfortable, well-care-for home with a layout that makes everyday living easy!

3 Beds ⋅ 2 Baths ⋅ 26025070 MLS

Welcome to 317 Vanover Way! This beautiful, well-maintained 3-bedroom, 2-bath home is move-in ready and waiting for its next owner. Step inside to a spacious living room with the bedrooms conveniently located just off the main living area. Coming in from the garage, you'll find a functional mudroom and laundry area that leads directly into the kitchen. Outside, enjoy a nice-sized fenced backyard and a deck that's perfect for entertaining, relaxing, or enjoying time outdoors. A comfortable, well-care-for home with a layout that makes everyday living easy!

317 Vanover Way, Winchester

$249,000

This charming Cape Cod home is tucked away in an established Winchester neighborhood only 14 miles to Hamburg and less than 5 minutes to I64. You will love the short walk to Legacy Park! Yes, it does have a 1st floor Primary bedroom. This cute home has lots of character throughout with a spacious living room and an inviting dining room. The roof is only 2 years old; the heating and cooling has been well maintained, and the exterior of the home has been recently painted. The upstairs area offers 2 additional bedrooms and a full bathroom. The basement has additional storage space and a laundry area. There is so much private outdoor space to enjoy! The huge backyard is fenced and backs up to greenspace. There is a large patio perfect for friends and family gatherings. If you need extra storage space, you will enjoy the detached 2 car garage for all your outdoor toys. For convenience the property also has two separate driveways. Don't wait on this one! Schedule your private tour today.

3 Beds ⋅ 2 Baths ⋅ 26029418 MLS

This charming Cape Cod home is tucked away in an established Winchester neighborhood only 14 miles to Hamburg and less than 5 minutes to I64. You will love the short walk to Legacy Park! Yes, it does have a 1st floor Primary bedroom. This cute home has lots of character throughout with a spacious living room and an inviting dining room. The roof is only 2 years old; the heating and cooling has been well maintained, and the exterior of the home has been recently painted. The upstairs area offers 2 additional bedrooms and a full bathroom. The basement has additional storage space and a laundry area. There is so much private outdoor space to enjoy! The huge backyard is fenced and backs up to greenspace. There is a large patio perfect for friends and family gatherings. If you need extra storage space, you will enjoy the detached 2 car garage for all your outdoor toys. For convenience the property also has two separate driveways. Don't wait on this one! Schedule your private tour today.

48 Bon-Haven Ave, Winchester

$249,000

Welcome home to this spacious, low-maintenance townhome offering 3 levels of living space in a well established neighborhood. Thoughtfully maintained, a 3 year old roof, with recently replaced windows. This home offers plenty of room to spread out while keeping everyday living comfortable and convenient. The main level features a generously sized kitchen and family room with plenty of space for entertaining or gathering with family and friends. The lower level adds even more flexibility with a bonus room that could serve as a home office, recreation room, workout space, or additional living area. Upstairs you'll find 3 bedrooms, 2 full bathrooms, and ample closet space throughout. Outside, enjoy a large backyard backing to green space, along with the convenience of a rear-facing garage and a neighborhood walking trail. Ideally located with quick access to I-64 and approximately 20 minutes from Lexington's Hamburg area, this home combines space, updates, low-maintenance living, and a convenient location in one inviting package. Schedule your private showing today!

3 Beds ⋅ 3 Baths ⋅ 26022409 MLS

Welcome home to this spacious, low-maintenance townhome offering 3 levels of living space in a well established neighborhood. Thoughtfully maintained, a 3 year old roof, with recently replaced windows. This home offers plenty of room to spread out while keeping everyday living comfortable and convenient. The main level features a generously sized kitchen and family room with plenty of space for entertaining or gathering with family and friends. The lower level adds even more flexibility with a bonus room that could serve as a home office, recreation room, workout space, or additional living area. Upstairs you'll find 3 bedrooms, 2 full bathrooms, and ample closet space throughout. Outside, enjoy a large backyard backing to green space, along with the convenience of a rear-facing garage and a neighborhood walking trail. Ideally located with quick access to I-64 and approximately 20 minutes from Lexington's Hamburg area, this home combines space, updates, low-maintenance living, and a convenient location in one inviting package. Schedule your private showing today!

127 Bay Hill Dr, Winchester

$249,000

PRICED TO SELL! Highly Motivated Seller! 59 Hillcrest Dr, Winchester, KY 40391 3 Beds | 2 Baths | ~2,066 Total Sq Ft | Full Basement | Large Lot Attention buyers, DIYers, and investors: Don't miss this incredible value! The seller is highly motivated and ready to entertain offers, making this attractive ranch home priced to sell immediately with the oppurtunity to unlock instant equity! Key Highlights: Potential Mother-in-Law Suite: The fully finished, remodeled lower level includes a full bath, separate living area, dedicated laundry, its own entrance, and a non-conforming 4th bedroom (or ideal home office/hobby room)—offering the perfect layout for a mother-in-law suite, guest quarters, or independent living space. New HVAC! Original Hardwood Floors: Character and potential await! Classic original hardwood flooring runs through the main level, begging to be refinished to showcase its natural warmth and beauty. Expansive Yard Space: Enjoy outdoor freedom on a huge lot! Featuring a spacious, fully fenced back yard with endless possibilities for play, pets, or entertaining. Versatile Layout: Upstairs main-level living area combined with a versatile basement setup to suit any household's needs. Walk out basement provides seperate entrances to each level. Location & Value: Nestled in an established neighborhood in winchester, moments from GRC, and quick access to Lexington and Richmond! Opportunities with this much space, flexible living arrangements, and upside don't last long—bring all reasonable offers! Agent is owner.

4 Beds ⋅ 2 Baths ⋅ 26020680 MLS

PRICED TO SELL! Highly Motivated Seller! 59 Hillcrest Dr, Winchester, KY 40391 3 Beds | 2 Baths | ~2,066 Total Sq Ft | Full Basement | Large Lot Attention buyers, DIYers, and investors: Don't miss this incredible value! The seller is highly motivated and ready to entertain offers, making this attractive ranch home priced to sell immediately with the oppurtunity to unlock instant equity! Key Highlights: Potential Mother-in-Law Suite: The fully finished, remodeled lower level includes a full bath, separate living area, dedicated laundry, its own entrance, and a non-conforming 4th bedroom (or ideal home office/hobby room)—offering the perfect layout for a mother-in-law suite, guest quarters, or independent living space. New HVAC! Original Hardwood Floors: Character and potential await! Classic original hardwood flooring runs through the main level, begging to be refinished to showcase its natural warmth and beauty. Expansive Yard Space: Enjoy outdoor freedom on a huge lot! Featuring a spacious, fully fenced back yard with endless possibilities for play, pets, or entertaining. Versatile Layout: Upstairs main-level living area combined with a versatile basement setup to suit any household's needs. Walk out basement provides seperate entrances to each level. Location & Value: Nestled in an established neighborhood in winchester, moments from GRC, and quick access to Lexington and Richmond! Opportunities with this much space, flexible living arrangements, and upside don't last long—bring all reasonable offers! Agent is owner.

59 Hillcrest Dr, Winchester

$244,000

SHORT SALE OPPORTUNITY! 54 Locust Dr. is an all-brick ranch in Westland Park offering 3 bedrooms, 2 baths and 1,692 sq. ft. of finished living space, plus a full unfinished basement. The home features hardwood flooring, a 2-car attached garage, fenced backyard and covered patio. Previous owners completed structural work in the basement that includes a transferable lifetime warranty. The home retains much of its original character and offers an opportunity for a buyer to update the kitchen, baths and finishes to their own style. This property is being offered as a short sale, meaning the seller's lender must review and approve the purchase price and terms. Please allow approximately 30-45 days for lender review and approval of any offer. Property is being sold AS-IS; inspections are welcome.

3 Beds ⋅ 2 Baths ⋅ 26023633 MLS

SHORT SALE OPPORTUNITY! 54 Locust Dr. is an all-brick ranch in Westland Park offering 3 bedrooms, 2 baths and 1,692 sq. ft. of finished living space, plus a full unfinished basement. The home features hardwood flooring, a 2-car attached garage, fenced backyard and covered patio. Previous owners completed structural work in the basement that includes a transferable lifetime warranty. The home retains much of its original character and offers an opportunity for a buyer to update the kitchen, baths and finishes to their own style. This property is being offered as a short sale, meaning the seller's lender must review and approve the purchase price and terms. Please allow approximately 30-45 days for lender review and approval of any offer. Property is being sold AS-IS; inspections are welcome.

54 Locust Dr, Winchester

$239,000

This move-in ready townhome is located in Greenfield subdivision and sits on a quiet street with no through traffic. On the main level you will find 2 nicely sized bedrooms , 2 full baths, laundry closet along with a fully closed in sun-porch. The living room is spacious and the kitchen is equipped with top notch appliances. Below you will find the walkout basement where there is another bedroom, nice storage area with a half bath and a nice living or office area. Roof replaced this year, hot water heater replaced in 2025 and air replaced in 2023. Great location!! Close to schools, restaurants and shopping with I-64 only 2 miles away! Approximately 20 minutes from Hamburg. There is a very friendly cat that will be closed in the sun porch please don't let him out.

3 Beds ⋅ 3 Baths ⋅ 26025942 MLS

This move-in ready townhome is located in Greenfield subdivision and sits on a quiet street with no through traffic. On the main level you will find 2 nicely sized bedrooms , 2 full baths, laundry closet along with a fully closed in sun-porch. The living room is spacious and the kitchen is equipped with top notch appliances. Below you will find the walkout basement where there is another bedroom, nice storage area with a half bath and a nice living or office area. Roof replaced this year, hot water heater replaced in 2025 and air replaced in 2023. Great location!! Close to schools, restaurants and shopping with I-64 only 2 miles away! Approximately 20 minutes from Hamburg. There is a very friendly cat that will be closed in the sun porch please don't let him out.

102 Quail Ridge 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

$229,900

Looking for the perfect place to build your dream home, spread out, or simply own a beautiful piece of Kentucky? This 6-acre tract on Kiddville Road in Clark County offers the space, setting, and flexibility to make your vision a reality! The gently rolling landscape, minimal trees, and open acreage create multiple potential homesites, allowing you to choose the setting that feels just right for your future home. With utilities available, you can start envisioning everything from a peaceful country retreat to a beautiful forever home with plenty of room to enjoy the outdoors. There is even potential to add a pond if desired, creating an additional feature to enjoy and making the property even more picturesque. Whether you dream of a spacious yard, room for a garden, outdoor entertaining, a mini homestead, or simply having plenty of land around you, there is room here to make it your own. Plus, the location gives you the best of both worlds! Enjoy the privacy and open space of 6 acres while being just minutes from the Mountain Parkway and Winchester. It's not every day you find this much land in such a convenient location with so many possibilities. Walk the property, take in the views, and start imagining what you could create here!

26027224 MLS

Looking for the perfect place to build your dream home, spread out, or simply own a beautiful piece of Kentucky? This 6-acre tract on Kiddville Road in Clark County offers the space, setting, and flexibility to make your vision a reality! The gently rolling landscape, minimal trees, and open acreage create multiple potential homesites, allowing you to choose the setting that feels just right for your future home. With utilities available, you can start envisioning everything from a peaceful country retreat to a beautiful forever home with plenty of room to enjoy the outdoors. There is even potential to add a pond if desired, creating an additional feature to enjoy and making the property even more picturesque. Whether you dream of a spacious yard, room for a garden, outdoor entertaining, a mini homestead, or simply having plenty of land around you, there is room here to make it your own. Plus, the location gives you the best of both worlds! Enjoy the privacy and open space of 6 acres while being just minutes from the Mountain Parkway and Winchester. It's not every day you find this much land in such a convenient location with so many possibilities. Walk the property, take in the views, and start imagining what you could create here!

9999 Kiddville 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

$225,000

Looking for low-maintenance living without giving up space? This Winchester townhouse offers three bedrooms, 2.5 baths and a comfortable two-story layout with room to spread out. The main level features a spacious living room with a fireplace, dining area, kitchen and half bath. Just off the dining area, the back deck gives you a nice spot to relax or enjoy some time outside. Upstairs, the primary bedroom has its own private bath and large walk-in closet, along with two additional bedrooms, another full bath and laundry. There's also an attached garage and plenty of closet space throughout. A great option for anyone looking for an easy-to-maintain home with the space and storage you don't always find in a townhouse.

3 Beds ⋅ 3 Baths ⋅ 26025201 MLS

Looking for low-maintenance living without giving up space? This Winchester townhouse offers three bedrooms, 2.5 baths and a comfortable two-story layout with room to spread out. The main level features a spacious living room with a fireplace, dining area, kitchen and half bath. Just off the dining area, the back deck gives you a nice spot to relax or enjoy some time outside. Upstairs, the primary bedroom has its own private bath and large walk-in closet, along with two additional bedrooms, another full bath and laundry. There's also an attached garage and plenty of closet space throughout. A great option for anyone looking for an easy-to-maintain home with the space and storage you don't always find in a townhouse.

115 Quail Ridge Rd, Winchester

$225,000

Located on the very visible corner of Lexington Avenue and Main Street, this property has recently been updated. Wonderful tenants in both the upstairs and downstairs unit makes this a great investment property. The historic Leeds Center for the Arts, numerous other restaurants and shops are in walking distance. This is an ideal location for an investment property or bring your business here. This property is also located in the Opportunity Zone. Lots of options! Winchester, KY is conveniently situated just 18 miles east of Lexington and, with proximity to I-64, provides quick access to the larger city's amenities. Downtown Winchester is home to a variety of beloved local establishments, including the historic Leeds Center for the Arts, La Trattoria, Loma's, The Hall Coffee & Social Club, and several small shops. Over 30 new, high-end apartments are coming to Downtown Winchester - residents and tourists want to be Downtown! Property Highlights: -Excellent investment property with Tenants in place -Ideal location in Downtown Winchester -Located in the Opportunity Zone

26019968 MLS

Located on the very visible corner of Lexington Avenue and Main Street, this property has recently been updated. Wonderful tenants in both the upstairs and downstairs unit makes this a great investment property. The historic Leeds Center for the Arts, numerous other restaurants and shops are in walking distance. This is an ideal location for an investment property or bring your business here. This property is also located in the Opportunity Zone. Lots of options! Winchester, KY is conveniently situated just 18 miles east of Lexington and, with proximity to I-64, provides quick access to the larger city's amenities. Downtown Winchester is home to a variety of beloved local establishments, including the historic Leeds Center for the Arts, La Trattoria, Loma's, The Hall Coffee & Social Club, and several small shops. Over 30 new, high-end apartments are coming to Downtown Winchester - residents and tourists want to be Downtown! Property Highlights: -Excellent investment property with Tenants in place -Ideal location in Downtown Winchester -Located in the Opportunity Zone

1 N Main St, Winchester

$221,000

Motivated Seller, just lowered the price, seller if offering $2000 for concessions, This is great space for the price, walk into a great room with firepalce, hardwood floors, dining area leads to enclosed sunporch, master suite with full bath on first floor, nice kitchen , large back yard, 2 bedrooms up with fill bath, semi finished basement, 1 car garage, don't miss out on this townhome in a great location

3 Beds ⋅ 2 Baths ⋅ 26028482 MLS

Motivated Seller, just lowered the price, seller if offering $2000 for concessions, This is great space for the price, walk into a great room with firepalce, hardwood floors, dining area leads to enclosed sunporch, master suite with full bath on first floor, nice kitchen , large back yard, 2 bedrooms up with fill bath, semi finished basement, 1 car garage, don't miss out on this townhome in a great location

106 Quail Ridge Rd, Winchester

$220,000

Charming, move in ready 3-bedroom home just minutes from downtown Winchester! This inviting home features LVP flooring throughout, beautiful granite countertops, and a practical layout that makes everyday living easy. With three bedrooms and a full bath, there's plenty of space to make it your own. Enjoy the convenience of being close to downtown Winchester, local dining, shopping, and everything the community has to offer. Come see all this place has to offer and discover your next place to call home!

3 Beds ⋅ 1 Baths ⋅ 26027559 MLS

Charming, move in ready 3-bedroom home just minutes from downtown Winchester! This inviting home features LVP flooring throughout, beautiful granite countertops, and a practical layout that makes everyday living easy. With three bedrooms and a full bath, there's plenty of space to make it your own. Enjoy the convenience of being close to downtown Winchester, local dining, shopping, and everything the community has to offer. Come see all this place has to offer and discover your next place to call home!

15 Maryland Ave, Winchester

$219,900

Charming ranch home featuring 3 bedrooms, 1 full bath with a spacious layout and inviting curb appeal. Enjoy relaxing or entertaining on the covered back patio overlooking the large backyard with plenty of room for pets, play, or gardening. The kitchen offers beautiful granite countertops, ample cabinet space, and all appliances stay for added convenience. A wonderful opportunity for comfortable one-level living.

3 Beds ⋅ 1 Baths ⋅ 26023054 MLS

Charming ranch home featuring 3 bedrooms, 1 full bath with a spacious layout and inviting curb appeal. Enjoy relaxing or entertaining on the covered back patio overlooking the large backyard with plenty of room for pets, play, or gardening. The kitchen offers beautiful granite countertops, ample cabinet space, and all appliances stay for added convenience. A wonderful opportunity for comfortable one-level living.

125 Kittison Dr, Winchester

$219,900

PRIME COMMERCIAL PROPERTY!!!! High traffic, high visibilty, with a ton of potential! Exceptional commercial property located in an excellent location with outstanding exposure for your business. Positioned on a busy roadway, this property offers maximum visibility to thousands of passing vehicles each day, making it an ideal location for retail, office space, a restaurant, medical practice, or service-based business. With easy access, excellent frontage, and endless potential, this is a rare opportunity to establish or expand your business in one of the area's most sought-after commercial corridors. Don't miss your chance to invest in a location where your business can thrive. Located within close proximity to the planned Publix and new shopping center. Agent/owner

26020972 MLS

PRIME COMMERCIAL PROPERTY!!!! High traffic, high visibilty, with a ton of potential! Exceptional commercial property located in an excellent location with outstanding exposure for your business. Positioned on a busy roadway, this property offers maximum visibility to thousands of passing vehicles each day, making it an ideal location for retail, office space, a restaurant, medical practice, or service-based business. With easy access, excellent frontage, and endless potential, this is a rare opportunity to establish or expand your business in one of the area's most sought-after commercial corridors. Don't miss your chance to invest in a location where your business can thrive. Located within close proximity to the planned Publix and new shopping center. Agent/owner

106 Mcclure Rd, Winchester

$219,900

*NEW ROOF!* Welcome home to this well-established 3-bedroom, 2-bath coveted brick ranch offering easy one-level ranch living in a wonderful location close to all the conveniences that Winchester has to offer, including a community pool and gym just a couple turns away. The spacious open family room features a gas fireplace and flows into the spacious kitchen, featuring bamboo wood flooring, a large granite island, newer stainless steel appliances, and a gas range. Step outside and enjoy your own Aurora above-ground pool perfect for family entertaining. The partially fenced backyard also includes an oversized storage/tool shed, providing plenty of room for hobbies and extra storage. Enjoy peace of mind with major updates including a newer HVAC system, water heater, Window World windows (approximately 5 years old), and a new roof with a 5-year warranty. This solidly built home is full of potential and has served the current owners well as they transition to their next chapter in life. It is ready and waiting for a new family to come and breathe life and make it a home once again.

3 Beds ⋅ 2 Baths ⋅ 26018492 MLS

*NEW ROOF!* Welcome home to this well-established 3-bedroom, 2-bath coveted brick ranch offering easy one-level ranch living in a wonderful location close to all the conveniences that Winchester has to offer, including a community pool and gym just a couple turns away. The spacious open family room features a gas fireplace and flows into the spacious kitchen, featuring bamboo wood flooring, a large granite island, newer stainless steel appliances, and a gas range. Step outside and enjoy your own Aurora above-ground pool perfect for family entertaining. The partially fenced backyard also includes an oversized storage/tool shed, providing plenty of room for hobbies and extra storage. Enjoy peace of mind with major updates including a newer HVAC system, water heater, Window World windows (approximately 5 years old), and a new roof with a 5-year warranty. This solidly built home is full of potential and has served the current owners well as they transition to their next chapter in life. It is ready and waiting for a new family to come and breathe life and make it a home once again.

528 Estes Dr, Winchester

$219,900

Discover the possibilities with this unique dual-property offering at 3686 & 3688 Crowe Ridge Road. Enjoy the peace and privacy of a beautiful country setting with room to spread out and endless potential. Whether you're looking for a primary residence with additional living space, an investment opportunity, or housing for extended family, this property offers versatility that's hard to find. Conveniently located just minutes from Winchester off the Mountain Parkway, exit 10, and an easy commute to Lexington.

26016689 MLS

Discover the possibilities with this unique dual-property offering at 3686 & 3688 Crowe Ridge Road. Enjoy the peace and privacy of a beautiful country setting with room to spread out and endless potential. Whether you're looking for a primary residence with additional living space, an investment opportunity, or housing for extended family, this property offers versatility that's hard to find. Conveniently located just minutes from Winchester off the Mountain Parkway, exit 10, and an easy commute to Lexington.

3686 Crowe Ridge Rd, Winchester

$219,000

Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviting covered front porch, perfect for morning coffee or evening unwinding. Inside, you'll find a spacious living room and dining room featuring beautiful hardwood floors that add warmth and character. The generous yard offers plenty of space for outdoor entertaining, gardening, play or future possibilities. Don't miss the opportunity to make this delightful property your new home! SOLD AS-Is

3 Beds ⋅ 2 Baths ⋅ 26019206 MLS

Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviting covered front porch, perfect for morning coffee or evening unwinding. Inside, you'll find a spacious living room and dining room featuring beautiful hardwood floors that add warmth and character. The generous yard offers plenty of space for outdoor entertaining, gardening, play or future possibilities. Don't miss the opportunity to make this delightful property your new home! SOLD AS-Is

13 Long Ave, Winchester

$215,000

Welcome to 600 College Street! Offering over 1,700 square feet, this versatile Winchester home features 3 bedrooms, 2 full bathrooms, plus an additional room ideal for a 4th bedroom, home office, or flex space. Inside, you'll find a spacious living room and a dining room with plenty of room to create additional living or entertaining space. The kitchen offers a walk-in pantry and conveniently located laundry area. An unfinished basement provides ample storage and walkout access, while the attached one-car garage adds everyday convenience. Outside, enjoy a covered front porch and a peaceful back porch surrounded by mature trees for added privacy. Conveniently located near Downtown Winchester, College Park, Legacy Grove, local shopping, dining, and everyday amenities, with easy access to I-64 for a straightforward commute toward Lexington. Improvements, including a roof replacement, LVP flooring, renovated kitchen and baths, and updated plumbing all done in 2024. Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ 26026485 MLS

Welcome to 600 College Street! Offering over 1,700 square feet, this versatile Winchester home features 3 bedrooms, 2 full bathrooms, plus an additional room ideal for a 4th bedroom, home office, or flex space. Inside, you'll find a spacious living room and a dining room with plenty of room to create additional living or entertaining space. The kitchen offers a walk-in pantry and conveniently located laundry area. An unfinished basement provides ample storage and walkout access, while the attached one-car garage adds everyday convenience. Outside, enjoy a covered front porch and a peaceful back porch surrounded by mature trees for added privacy. Conveniently located near Downtown Winchester, College Park, Legacy Grove, local shopping, dining, and everyday amenities, with easy access to I-64 for a straightforward commute toward Lexington. Improvements, including a roof replacement, LVP flooring, renovated kitchen and baths, and updated plumbing all done in 2024. Schedule your private showing today!

600 College St, Winchester

$209,000

Really Nice all Brick 3 bedroom, 1 Bath Ranch with large garage and a fully enclosed covered back patio in desireable Colonial Valley Neighborhood. Low Electric bills, HVAC 2 years old, Water Heater 3 years. Most comparable homes in this neighborhood don't have a garage or enclosed porch. Picture of Range and refrigerator are for illustration only. Seller will give a $1,000 allowance for appliances

3 Beds ⋅ 1 Baths ⋅ 26029492 MLS

Really Nice all Brick 3 bedroom, 1 Bath Ranch with large garage and a fully enclosed covered back patio in desireable Colonial Valley Neighborhood. Low Electric bills, HVAC 2 years old, Water Heater 3 years. Most comparable homes in this neighborhood don't have a garage or enclosed porch. Picture of Range and refrigerator are for illustration only. Seller will give a $1,000 allowance for appliances

117 Colonial Park Dr, Winchester

$209,000

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

$205,000

Price Improvement! FHA and USDA Loan Eligible! Welcome to this charming 3-bedroom, 2-bathroom home offers comfortable living with several important updates already in place. Featuring a newer HVAC system and newer roof, this home provides peace of mind for its next owner while offering plenty of opportunity to make the space your own. Inside, you'll find a bright, inviting layout with fresh, neutral finishes, updated flooring, and plenty of natural light. The spacious living area features a classic brick fireplace, creating a warm focal point for relaxing or entertaining. The updated kitchen offers new white cabinetry, stainless steel appliances, subway tile backsplash, ample counter space, and new granite countertops. Both bathrooms have been updated with clean, modern finishes, including attractive tile work and contemporary fixtures. The home's three bedrooms provide flexibility for family, guests, a home office, or additional living space. Outside, enjoy a covered front porch and established, tree-lined surroundings that provide a private and welcoming setting. The rear of the property offers additional outdoor space and a detached storage/outbuilding area. Conveniently located in Winchester, this home combines a comfortable residential setting with easy access to local shopping, dining, schools, and major roadways. Whether you're looking for a primary residence or an investment opportunity, this well-maintained home is worth a look! Motivated Sellers!

3 Beds ⋅ 2 Baths ⋅ 26022771 MLS

Price Improvement! FHA and USDA Loan Eligible! Welcome to this charming 3-bedroom, 2-bathroom home offers comfortable living with several important updates already in place. Featuring a newer HVAC system and newer roof, this home provides peace of mind for its next owner while offering plenty of opportunity to make the space your own. Inside, you'll find a bright, inviting layout with fresh, neutral finishes, updated flooring, and plenty of natural light. The spacious living area features a classic brick fireplace, creating a warm focal point for relaxing or entertaining. The updated kitchen offers new white cabinetry, stainless steel appliances, subway tile backsplash, ample counter space, and new granite countertops. Both bathrooms have been updated with clean, modern finishes, including attractive tile work and contemporary fixtures. The home's three bedrooms provide flexibility for family, guests, a home office, or additional living space. Outside, enjoy a covered front porch and established, tree-lined surroundings that provide a private and welcoming setting. The rear of the property offers additional outdoor space and a detached storage/outbuilding area. Conveniently located in Winchester, this home combines a comfortable residential setting with easy access to local shopping, dining, schools, and major roadways. Whether you're looking for a primary residence or an investment opportunity, this well-maintained home is worth a look! Motivated Sellers!

3 Nunnelly Ct, Winchester

$204,900

Beautiful 3-bedroom, 1-bath home located at the end of a quiet, well established neighborhood within walking distance to downtown Winchester. This home features hardwood floors, a versatile in home office or bonus room, and several recent upgrades including a new stove, microwave, refrigerator, cabinets, and HVAC (1 year old). The property offers a backyard with a storage shed, providing convenient space for tools and outdoor equipment. Its desirable location combines privacy with easy access to local shops, dining, and downtown community events. Call today for your private showing. Owner/Agent

3 Beds ⋅ 1 Baths ⋅ 26021864 MLS

Beautiful 3-bedroom, 1-bath home located at the end of a quiet, well established neighborhood within walking distance to downtown Winchester. This home features hardwood floors, a versatile in home office or bonus room, and several recent upgrades including a new stove, microwave, refrigerator, cabinets, and HVAC (1 year old). The property offers a backyard with a storage shed, providing convenient space for tools and outdoor equipment. Its desirable location combines privacy with easy access to local shops, dining, and downtown community events. Call today for your private showing. Owner/Agent

38 Mackay Ave, Winchester

$200,000

3 Beds ⋅ 1 Baths ⋅ 26027397 MLS

213 E Broadway St, Winchester

$200,000

Exciting opportunity for congregations, investors, or visionaries seeking a one-of-a-kind property! This spacious one-level property offers over 2,500 sq ft with 2 bathrooms, a roof that is approximately 6 years old, and endless possibilities for renovation or repurposing. Situated on a quiet street, this unique space provides the perfect canvas to bring your vision to life. Property is being sold as-is. Buyers to verify square footage and lot size.

26013923 MLS

Exciting opportunity for congregations, investors, or visionaries seeking a one-of-a-kind property! This spacious one-level property offers over 2,500 sq ft with 2 bathrooms, a roof that is approximately 6 years old, and endless possibilities for renovation or repurposing. Situated on a quiet street, this unique space provides the perfect canvas to bring your vision to life. Property is being sold as-is. Buyers to verify square footage and lot size.

3150 Waterworks Rd, Winchester

$199,900

606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom faucets were all added in 2025. The living room fireplace and original trim add so much character, while the enclosed laundry and mudroom gives you useful extra space. Downstairs, the full unfinished walk-up basement offers more than 1,000 square feet for storage, hobbies, or future possibilities. Outside, you'll find a fenced backyard, detached one-car garage, storage shed, and welcoming front porch. The seller reports the roof and HVAC are both under six years old. A wonderful home with charm, practical space, and a great Winchester location!

2 Beds ⋅ 1 Baths ⋅ 26021605 MLS

606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom faucets were all added in 2025. The living room fireplace and original trim add so much character, while the enclosed laundry and mudroom gives you useful extra space. Downstairs, the full unfinished walk-up basement offers more than 1,000 square feet for storage, hobbies, or future possibilities. Outside, you'll find a fenced backyard, detached one-car garage, storage shed, and welcoming front porch. The seller reports the roof and HVAC are both under six years old. A wonderful home with charm, practical space, and a great Winchester location!

606 College St, Winchester

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