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Beautifully updated Craftsman-style ranch offering over 2,000 square feet of comfortable living space in a desirable Winchester location. Walking distance to downtown, the library, College park gym and pool. This move-in-ready home blends timeless character with extensive modern updates, including a new roof, new 6" gutters, new HVAC system, new water heater, fresh interior paint, updated windows, lighting, switches, and outlets throughout. The renovated kitchen is the heart of the home, featuring granite countertops, a center island, and appliances replaced in 2025. Major improvements provide added peace of mind, including the plumbing drain lines replaced from the home to the road, bathroom walk-in shower and new toilets. Enjoy the convenience of a carport, off-street parking, and a welcoming covered front porch that enhances the home's Craftsman charm. The backyard offers a highly usable outdoor space perfect for entertaining, gardening, pets, or simply relaxing. With extensive updates already completed, this well-maintained home is ready for its next owner to enjoy.

3 Beds ⋅ 2 Baths ⋅ 26025290 MLS

Beautifully updated Craftsman-style ranch offering over 2,000 square feet of comfortable living space in a desirable Winchester location. Walking distance to downtown, the library, College park gym and pool. This move-in-ready home blends timeless character with extensive modern updates, including a new roof, new 6" gutters, new HVAC system, new water heater, fresh interior paint, updated windows, lighting, switches, and outlets throughout. The renovated kitchen is the heart of the home, featuring granite countertops, a center island, and appliances replaced in 2025. Major improvements provide added peace of mind, including the plumbing drain lines replaced from the home to the road, bathroom walk-in shower and new toilets. Enjoy the convenience of a carport, off-street parking, and a welcoming covered front porch that enhances the home's Craftsman charm. The backyard offers a highly usable outdoor space perfect for entertaining, gardening, pets, or simply relaxing. With extensive updates already completed, this well-maintained home is ready for its next owner to enjoy.

118 College St, Winchester

$307,900

Enjoy rest, relaxation and all the outdoor activities you can dream up with this home. Cozy, 3-bedroom, 2-bathroom home ranch with attached one car garage in a well-established neighborhood. Home features new gas stove & range hood, new bathroom updates, hardwood floors, pocket doors, updated finishes, ventless gas fireplace, sunroom and professionally maintained in-ground pool with concrete patio and so much more. This home keeps going with additional fencing and more yard with storage shed. Inspections welcome. Come take a look and make this home yours. Warranties to pass to new owner for stove, hood range, existing dishwasher and refrigerator.

3 Beds ⋅ 2 Baths ⋅ 26006695 MLS

Enjoy rest, relaxation and all the outdoor activities you can dream up with this home. Cozy, 3-bedroom, 2-bathroom home ranch with attached one car garage in a well-established neighborhood. Home features new gas stove & range hood, new bathroom updates, hardwood floors, pocket doors, updated finishes, ventless gas fireplace, sunroom and professionally maintained in-ground pool with concrete patio and so much more. This home keeps going with additional fencing and more yard with storage shed. Inspections welcome. Come take a look and make this home yours. Warranties to pass to new owner for stove, hood range, existing dishwasher and refrigerator.

118 Windridge Dr, Winchester

$305,000

***Motivated Sellers*** Beautifully updated ranch on a new, fully finished walk out basement. 5 bedrooms, 2 being primary suites, one on the main level and one in the basement. This house is perfect for multigenerational living. New paint, floors, back splash, kitchen cabinets and granite counter tops. The fully finished basement has a newly added primary bedroom and bath. The updated bathroom has a double vanity with his and her's walk in closets. You will find the other primary and 2 additional bedrooms and 2 bathrooms on the main level. The front porch invites you into the cozy living room that effortlessly flows into the dining area and updated kitchen. Out back is a deck where you can keep your grill. Perfect for entertaining the deck has stairs to the lower patio where you will find a large backyard equipped with a fire pit, storage shed and is fully fenced. The family room, laundry room and one additional bedroom are also in the basement. Two year old roof. This house has been well maintained and is perfect for the first time home buyer or those needing more space and bedrooms.

5 Beds ⋅ 3 Baths ⋅ 26008797 MLS

***Motivated Sellers*** Beautifully updated ranch on a new, fully finished walk out basement. 5 bedrooms, 2 being primary suites, one on the main level and one in the basement. This house is perfect for multigenerational living. New paint, floors, back splash, kitchen cabinets and granite counter tops. The fully finished basement has a newly added primary bedroom and bath. The updated bathroom has a double vanity with his and her's walk in closets. You will find the other primary and 2 additional bedrooms and 2 bathrooms on the main level. The front porch invites you into the cozy living room that effortlessly flows into the dining area and updated kitchen. Out back is a deck where you can keep your grill. Perfect for entertaining the deck has stairs to the lower patio where you will find a large backyard equipped with a fire pit, storage shed and is fully fenced. The family room, laundry room and one additional bedroom are also in the basement. Two year old roof. This house has been well maintained and is perfect for the first time home buyer or those needing more space and bedrooms.

28 Churchill Dr, Winchester

$300,000

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

3 Beds ⋅ 2 Baths ⋅ 26013010 MLS

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

23 Windridge Dr, Winchester

$299,900

This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. With recently installed vinyl siding, gutters and gutter guard properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming laminate floors and a brick fireplace; the perfect place to settle in on a cold winter evening. The kitchen features stainless appliances including a double wall oven, ample cabinetry and abundant lighting with plenty of counterspace for cooking your favorite meals as well as two recessed sky-light windows providing natural lighting. From the kitchen you can access the back deck which must be seen to be appreciated! Multiple levels of decking surround the backyard providing an amazing area for outdoor living, including a cement patio that would be an excellent location for a hot tub. The privacy fencing and backing up to a natural greenspace make the back yard feel like your own private oasis. In the primary suite, a vaulted ceiling provides a feeling of spaciousness beside the generous bathroom with a handicap accessible, tiled, walk-in shower and a large, cedar-lined, walk-in closet. Other closets in the home are also cedar lined. Take a ride to the basement on the lift chair to access a partially finished basement including a kitchenette and additional full bathroom. The previous owner had a movie room in the basement and used the custom platform to create tiered seating for movie viewing. The attached garage is spacious enough to hold up to 4 cars or create a workshop space and still have room to park. Schedule your private showing today and see if this home might be right for you!

3 Beds ⋅ 3 Baths ⋅ 26012206 MLS

This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. With recently installed vinyl siding, gutters and gutter guard properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming laminate floors and a brick fireplace; the perfect place to settle in on a cold winter evening. The kitchen features stainless appliances including a double wall oven, ample cabinetry and abundant lighting with plenty of counterspace for cooking your favorite meals as well as two recessed sky-light windows providing natural lighting. From the kitchen you can access the back deck which must be seen to be appreciated! Multiple levels of decking surround the backyard providing an amazing area for outdoor living, including a cement patio that would be an excellent location for a hot tub. The privacy fencing and backing up to a natural greenspace make the back yard feel like your own private oasis. In the primary suite, a vaulted ceiling provides a feeling of spaciousness beside the generous bathroom with a handicap accessible, tiled, walk-in shower and a large, cedar-lined, walk-in closet. Other closets in the home are also cedar lined. Take a ride to the basement on the lift chair to access a partially finished basement including a kitchenette and additional full bathroom. The previous owner had a movie room in the basement and used the custom platform to create tiered seating for movie viewing. The attached garage is spacious enough to hold up to 4 cars or create a workshop space and still have room to park. Schedule your private showing today and see if this home might be right for you!

3622 Stamper Dr, Winchester

$299,900

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

4 Beds ⋅ 3 Baths ⋅ 26015653 MLS

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

209 Connie Ln, Winchester

$293,000

Welcome home to this adorable 2 bedroom, 1 bathroom farmhouse on 5 peaceful acres. Inside, the layout is open and inviting with LVP and hardwood flooring throughout with a tiled bath. The kitchen and family room flow together and feature beautiful exposed wood beams that are hundreds of years old and reclaimed from an old church. A wood-burning stove in the family room adds warmth and character on cozy days, and the kitchen feels straight out of an HGTV show with a new island and a layout designed for cooking, gathering, and entertaining. The bedrooms offer multiple closets, and the full bath includes a convenient laundry space. A formal living room at the front of the home provides extra flexibility for a home office or sitting area. Outside, a large multi-level deck wraps from the side of the home around to the back, creating the perfect setting for outdoor dining or quiet mornings with coffee. The 5 acre property has a large clearing behind the house, offering space for a pool, garden, or play area, while the rest of the land is wooded and gently sloped, offering privacy and a scenic backdrop. There are already two raised garden beds and a spot for a fire pit in the side yard, plus a detached garage, chicken coop, and storage shed. The HVAC system is brand new, and the roof is only two years old. This property has been well cared for and thoughtfully upgraded over the years. Come see why this farmhouse could be your perfect country retreat!

2 Beds ⋅ 1 Baths ⋅ 25503339 MLS

Welcome home to this adorable 2 bedroom, 1 bathroom farmhouse on 5 peaceful acres. Inside, the layout is open and inviting with LVP and hardwood flooring throughout with a tiled bath. The kitchen and family room flow together and feature beautiful exposed wood beams that are hundreds of years old and reclaimed from an old church. A wood-burning stove in the family room adds warmth and character on cozy days, and the kitchen feels straight out of an HGTV show with a new island and a layout designed for cooking, gathering, and entertaining. The bedrooms offer multiple closets, and the full bath includes a convenient laundry space. A formal living room at the front of the home provides extra flexibility for a home office or sitting area. Outside, a large multi-level deck wraps from the side of the home around to the back, creating the perfect setting for outdoor dining or quiet mornings with coffee. The 5 acre property has a large clearing behind the house, offering space for a pool, garden, or play area, while the rest of the land is wooded and gently sloped, offering privacy and a scenic backdrop. There are already two raised garden beds and a spot for a fire pit in the side yard, plus a detached garage, chicken coop, and storage shed. The HVAC system is brand new, and the roof is only two years old. This property has been well cared for and thoughtfully upgraded over the years. Come see why this farmhouse could be your perfect country retreat!

1508 Ford Hampton Rd, Winchester

$292,500

Beautiful Four Bedroom 2 Bathroom Ranch Home On A Finished Basement With Over 2 Acres!! Bring Your Family, Toys, Animals And Enjoy Country Living Close To Mountain Parkway And Close To Two Country Restaurants! Sellers Have Finished Basement To Add An Additional Bedroom, Bathroom And Lots Of Storage!! And Dont Miss The Large Deck With a View!

4 Beds ⋅ 2 Baths ⋅ 26008462 MLS

Beautiful Four Bedroom 2 Bathroom Ranch Home On A Finished Basement With Over 2 Acres!! Bring Your Family, Toys, Animals And Enjoy Country Living Close To Mountain Parkway And Close To Two Country Restaurants! Sellers Have Finished Basement To Add An Additional Bedroom, Bathroom And Lots Of Storage!! And Dont Miss The Large Deck With a View!

306 Trapp-Goffs Cor Rd, Winchester

$292,000

Welcome home to this well-maintained, one-owner split-level offering space, comfort, and endless possibilities! Featuring 4 bedrooms and 2 full baths, this home provides room for everyone. Enjoy both a spacious living room and cozy family room wih a fireplace, perfect for relaxing or entertaining. The functional floor plan offers flexibility for today's lifestyle. New carpet and fresh paint throughout the house! Don't miss this opportunity to make this cherished home your own!

4 Beds ⋅ 2 Baths ⋅ 26014681 MLS

Welcome home to this well-maintained, one-owner split-level offering space, comfort, and endless possibilities! Featuring 4 bedrooms and 2 full baths, this home provides room for everyone. Enjoy both a spacious living room and cozy family room wih a fireplace, perfect for relaxing or entertaining. The functional floor plan offers flexibility for today's lifestyle. New carpet and fresh paint throughout the house! Don't miss this opportunity to make this cherished home your own!

872 Stratton Ln, Winchester

$290,000

If you've been looking for an amazing "light" renovation opportunity, this is it! Over 3300 sq ft w tons of character situated on an acre of land w gorgeous mature trees. *Seller's are contributing $5,000 towards buyer's prepaids/closing costs.* Flooring, roof, HVAC heat pumps are under 6 years old. New windows & gutters installed May 2026. Under 5 minutes to 64. Don't let this one pass you by. Come check this property out for yourself!

5 Beds ⋅ 3 Baths ⋅ 26018116 MLS

If you've been looking for an amazing "light" renovation opportunity, this is it! Over 3300 sq ft w tons of character situated on an acre of land w gorgeous mature trees. *Seller's are contributing $5,000 towards buyer's prepaids/closing costs.* Flooring, roof, HVAC heat pumps are under 6 years old. New windows & gutters installed May 2026. Under 5 minutes to 64. Don't let this one pass you by. Come check this property out for yourself!

4603 Paris Rd, Winchester

$290,000

**Click on the Virtual Tour section to see the video walk through!** Discover your own slice of country paradise in southern Clark County. This 51+ acre property blends open pasture with mature woodland, offering endless possibilities—raise cattle, plant crops, keep horses, enjoy outdoor recreation, or build the homestead you've always imagined. Currently used as a private family retreat, the land already has electricity on-site and includes a cistern at an old home location, with public water available at the road. The gently rolling and hilly terrain provides beautiful views, natural seclusion, and plenty of space to explore. A gravel drive leads to a classic tobacco barn, and beyond that, the land opens into areas best navigated by 4WD—perfect for adventurers and nature lovers. Whether you're dreaming of a peaceful getaway, a working farm, or a future home, this property is full of potential. Start imagining what you could create on 51+ stunning Kentucky acres. The land is private and gated, and showings are available by appointment only. (Drone Photos on 4/2)

26006323 MLS

**Click on the Virtual Tour section to see the video walk through!** Discover your own slice of country paradise in southern Clark County. This 51+ acre property blends open pasture with mature woodland, offering endless possibilities—raise cattle, plant crops, keep horses, enjoy outdoor recreation, or build the homestead you've always imagined. Currently used as a private family retreat, the land already has electricity on-site and includes a cistern at an old home location, with public water available at the road. The gently rolling and hilly terrain provides beautiful views, natural seclusion, and plenty of space to explore. A gravel drive leads to a classic tobacco barn, and beyond that, the land opens into areas best navigated by 4WD—perfect for adventurers and nature lovers. Whether you're dreaming of a peaceful getaway, a working farm, or a future home, this property is full of potential. Start imagining what you could create on 51+ stunning Kentucky acres. The land is private and gated, and showings are available by appointment only. (Drone Photos on 4/2)

750 Providence Ln, Winchester

$290,000

The original buyer's plans changed, and their loss may be your second chance. This beautiful Winchester ranch is the kind of home buyers walk into and immediately feel good about. From the vaulted ceilings and incredibly beautiful luxury vinyl plank flooring to the updated bathrooms, well-maintained systems, epoxied garage floor, and easy one-level layout, this home is truly move-in ready and built to be enjoyed for years to come. The charm continues outside with a covered front porch, a beautiful back wood deck, a relaxing pergola area, and a nice-sized backyard with a well-maintained vegetable garden ready for its next owner to enjoy. It has that rare "cute house" feeling that is hard to fake and even harder to find. In fact, agents who showed it the first time around said it best: "Wow, that was a cute house. We really enjoyed it." Homes like this do not come around often. This one hit the market a month and a half ago, received multiple offers, and now it is unexpectedly available again. Everything about this home feels like a little fairy tale that came true. Now is your chance. Do not miss out this time. Schedule your private showing today.

3 Beds ⋅ 2 Baths ⋅ 26014133 MLS

The original buyer's plans changed, and their loss may be your second chance. This beautiful Winchester ranch is the kind of home buyers walk into and immediately feel good about. From the vaulted ceilings and incredibly beautiful luxury vinyl plank flooring to the updated bathrooms, well-maintained systems, epoxied garage floor, and easy one-level layout, this home is truly move-in ready and built to be enjoyed for years to come. The charm continues outside with a covered front porch, a beautiful back wood deck, a relaxing pergola area, and a nice-sized backyard with a well-maintained vegetable garden ready for its next owner to enjoy. It has that rare "cute house" feeling that is hard to fake and even harder to find. In fact, agents who showed it the first time around said it best: "Wow, that was a cute house. We really enjoyed it." Homes like this do not come around often. This one hit the market a month and a half ago, received multiple offers, and now it is unexpectedly available again. Everything about this home feels like a little fairy tale that came true. Now is your chance. Do not miss out this time. Schedule your private showing today.

110 Buckingham Ln, Winchester

$290,000

This charming 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and potential! On a large corner lot in a cute, established neighborhood, this property features a spacious detached garage ideal for storage, hobbies, or workshop space. Inside, you'll find a functional layout with plenty of natural light and room to make it your own. The large partially unfinished basement provides endless possibilities for additional living space, recreation, storage, or future expansion. Step outside to enjoy the oversized covered patio — the perfect spot for relaxing, entertaining, or enjoying quiet evenings outdoors. Conveniently located with a welcoming neighborhood feel, this home is full of opportunity and ready for its next owner!

3 Beds ⋅ 2 Baths ⋅ 26011009 MLS

This charming 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and potential! On a large corner lot in a cute, established neighborhood, this property features a spacious detached garage ideal for storage, hobbies, or workshop space. Inside, you'll find a functional layout with plenty of natural light and room to make it your own. The large partially unfinished basement provides endless possibilities for additional living space, recreation, storage, or future expansion. Step outside to enjoy the oversized covered patio — the perfect spot for relaxing, entertaining, or enjoying quiet evenings outdoors. Conveniently located with a welcoming neighborhood feel, this home is full of opportunity and ready for its next owner!

147 Sunset Hts, Winchester

$290,000

This beautiful 1.5-story home offers all the charm of downtown in a small town, with a library, park, and restaurants nearby. Plus, just minutes to Lexington when the city is calling your name. This home has been remodeled for modern living, featuring an open floor plan. There is plenty of room for entertaining with a beautiful, well-equipped kitchen and a large island open to both the dining space and the living room. The first floor features all the luxuries, including a primary suite with an ensuite bathroom and a large walk-in closet, a dedicated laundry/mud room, and a powder room. Upstairs, you'll find two spacious bedrooms and an additional bathroom. The entertaining doesn't have to stop inside, as there is also a covered patio and a large fenced-in backyard ready for play. There's so much to this charmer, including a covered parking spot and an unfinished basement for additional storage.

3 Beds ⋅ 3 Baths ⋅ 26004053 MLS

This beautiful 1.5-story home offers all the charm of downtown in a small town, with a library, park, and restaurants nearby. Plus, just minutes to Lexington when the city is calling your name. This home has been remodeled for modern living, featuring an open floor plan. There is plenty of room for entertaining with a beautiful, well-equipped kitchen and a large island open to both the dining space and the living room. The first floor features all the luxuries, including a primary suite with an ensuite bathroom and a large walk-in closet, a dedicated laundry/mud room, and a powder room. Upstairs, you'll find two spacious bedrooms and an additional bathroom. The entertaining doesn't have to stop inside, as there is also a covered patio and a large fenced-in backyard ready for play. There's so much to this charmer, including a covered parking spot and an unfinished basement for additional storage.

322 S Burns Ave, Winchester

$287,000

This 3 bedroom, 2.5 bath home offers an incredible chance to build equity in a fantastic Winchester location close to shopping, dining, schools, and everyday conveniences. Big-ticket updates are already handled, including a new roof (2025), new water heater (2025), HVAC replaced in 2016, and updated doors/windows (2018)—giving buyers peace of mind where it matters most. Inside, the home is priced to reflect cosmetic updates needed, including paint and flooring, making this the perfect opportunity for buyers who want to personalize a home and gain instant value rather than pay premium pricing for cosmetic finishes they may change anyway. Whether you're a first-time buyer, investor, or someone looking for a smart opportunity in a desirable neighborhood, this one is worth a look.

3 Beds ⋅ 3 Baths ⋅ 26011852 MLS

This 3 bedroom, 2.5 bath home offers an incredible chance to build equity in a fantastic Winchester location close to shopping, dining, schools, and everyday conveniences. Big-ticket updates are already handled, including a new roof (2025), new water heater (2025), HVAC replaced in 2016, and updated doors/windows (2018)—giving buyers peace of mind where it matters most. Inside, the home is priced to reflect cosmetic updates needed, including paint and flooring, making this the perfect opportunity for buyers who want to personalize a home and gain instant value rather than pay premium pricing for cosmetic finishes they may change anyway. Whether you're a first-time buyer, investor, or someone looking for a smart opportunity in a desirable neighborhood, this one is worth a look.

207 Abbeywood Dr, Winchester

$286,000

Watch the sunrise from your own Winchester oasis. This 3 bed, 2 bath ranch blends warmth and comfort with a bright, open layout filled with natural light. Step outside to a large, private backyard with healthy fruit trees, a garden, entertaining deck, and covered paver patio, perfect for morning coffee or evening unwind. Located in a great neighborhood, walkable to Kroger and just 20 minutes to Lexington, this move in ready home offers the ideal mix of space, charm, and convenience.

3 Beds ⋅ 2 Baths ⋅ 26008814 MLS

Watch the sunrise from your own Winchester oasis. This 3 bed, 2 bath ranch blends warmth and comfort with a bright, open layout filled with natural light. Step outside to a large, private backyard with healthy fruit trees, a garden, entertaining deck, and covered paver patio, perfect for morning coffee or evening unwind. Located in a great neighborhood, walkable to Kroger and just 20 minutes to Lexington, this move in ready home offers the ideal mix of space, charm, and convenience.

110 Buckingham Ln, Winchester

$285,000

Welcome to this lovely move in ready gem. Perfectly positioned just off the Winchester Bypass. Whether you are commuting or looking for quick access to local shopping and dining, this location offers the perfect balance of connectivity and suburban quiet. Step through the front door and you will love the grandeur of the two-story living room and stairway and the additional accents of the beautiful custom moldings. The seamless flow between the kitchen, dining area, and living room makes it an ideal space for hosting guests or enjoying a quiet Sunday morning. The abundant cabinetry in the kitchen means you will be hard pressed to run out of storage space. The breakfast bar is perfect for casual meals or your morning coffee. The pantry will help keep your counters clear and your essentials organized. Upstairs there are three spacious bedrooms including the primary suite that acts as your own private sanctuary that offers the comfort you deserve. Love the outdoors? This home has you covered. With a covered front patio for you to sit and greet your neighbors or the rear deck to entertain or eat your meals alfresco. Fun fact... The wrought iron decorations on the siding of the outside entryway are from the Kentucky Castle. One of the previous owners, who made all the window boxes and detailed crown moldings at this home, did some of that type of work at the Kentucky Castle. The current owner planted beautiful wildflowers on the backyard hillside for you to enjoy while looking out your rear windows or sitting on your expansive rear deck. An oversized two car garage completes this lovely home that you would be proud to call your own.

3 Beds ⋅ 3 Baths ⋅ 26005798 MLS

Welcome to this lovely move in ready gem. Perfectly positioned just off the Winchester Bypass. Whether you are commuting or looking for quick access to local shopping and dining, this location offers the perfect balance of connectivity and suburban quiet. Step through the front door and you will love the grandeur of the two-story living room and stairway and the additional accents of the beautiful custom moldings. The seamless flow between the kitchen, dining area, and living room makes it an ideal space for hosting guests or enjoying a quiet Sunday morning. The abundant cabinetry in the kitchen means you will be hard pressed to run out of storage space. The breakfast bar is perfect for casual meals or your morning coffee. The pantry will help keep your counters clear and your essentials organized. Upstairs there are three spacious bedrooms including the primary suite that acts as your own private sanctuary that offers the comfort you deserve. Love the outdoors? This home has you covered. With a covered front patio for you to sit and greet your neighbors or the rear deck to entertain or eat your meals alfresco. Fun fact... The wrought iron decorations on the siding of the outside entryway are from the Kentucky Castle. One of the previous owners, who made all the window boxes and detailed crown moldings at this home, did some of that type of work at the Kentucky Castle. The current owner planted beautiful wildflowers on the backyard hillside for you to enjoy while looking out your rear windows or sitting on your expansive rear deck. An oversized two car garage completes this lovely home that you would be proud to call your own.

192 Prescott Ln, Winchester

$285,000

Conveniently located, this charming well kept home features a functional floor plan offering space that can be tailored for those who love to entertain or the growing family. On the main level you'll find the living room, an eat in kitchen, 3 bedrooms and a full bathroom. Off of the kitchen is a large deck that's perfect for get togethers with family or friends. Downstairs has a second living area/flex space as well as an additional bedroom and bathroom. The fenced in backyard features plenty of shade and a 12'x24' storage shed. Don't miss out on this great move in ready home! Seller is offering $3,000 BUYER CREDIT!

4 Beds ⋅ 2 Baths ⋅ 26009371 MLS

Conveniently located, this charming well kept home features a functional floor plan offering space that can be tailored for those who love to entertain or the growing family. On the main level you'll find the living room, an eat in kitchen, 3 bedrooms and a full bathroom. Off of the kitchen is a large deck that's perfect for get togethers with family or friends. Downstairs has a second living area/flex space as well as an additional bedroom and bathroom. The fenced in backyard features plenty of shade and a 12'x24' storage shed. Don't miss out on this great move in ready home! Seller is offering $3,000 BUYER CREDIT!

618 Westmeade Dr, Winchester

$285,000

PRICE DROP and a MOTIVATED SELLER!! Currently priced below 2026 Clark County Department of Revenue Property Assessment valuation. Turn-key, dialed-in, and ready to impress! This Craftsman-style stunner delivers the space, flow, and finishes today's buyers are chasing. With 3 oversized bedrooms, 2.5 baths, and a fully finished walk-out basement, this home lives large and shows even better. The main level hits immediately with an open, airy layout that connects living, dining, and kitchen into one seamless entertaining hub anchored by sleek stainless steel appliances and clean, modern finishes. Upstairs, the primary suite feels like a true retreat with a full bath and walk-in closet, while two additional bedrooms, a second full bath, and a dedicated laundry room keep everyday living effortless. From top to bottom, you'll love the cohesive design; neutral tones, plush carpet, and durable hardwood-look LVP that's as stylish as it is practical. And then there's the backyard! Fully fenced, private, and backing to scenic farmland for wide-open views you rarely find. Quiet, peaceful, and a perfect place to unwind or entertain. Homes with this combination of layout, finish, and setting don't sit. Schedule your showing and bring your buyers before it's gone. Seller is related to Listing Agent.

3 Beds ⋅ 3 Baths ⋅ 26008330 MLS

PRICE DROP and a MOTIVATED SELLER!! Currently priced below 2026 Clark County Department of Revenue Property Assessment valuation. Turn-key, dialed-in, and ready to impress! This Craftsman-style stunner delivers the space, flow, and finishes today's buyers are chasing. With 3 oversized bedrooms, 2.5 baths, and a fully finished walk-out basement, this home lives large and shows even better. The main level hits immediately with an open, airy layout that connects living, dining, and kitchen into one seamless entertaining hub anchored by sleek stainless steel appliances and clean, modern finishes. Upstairs, the primary suite feels like a true retreat with a full bath and walk-in closet, while two additional bedrooms, a second full bath, and a dedicated laundry room keep everyday living effortless. From top to bottom, you'll love the cohesive design; neutral tones, plush carpet, and durable hardwood-look LVP that's as stylish as it is practical. And then there's the backyard! Fully fenced, private, and backing to scenic farmland for wide-open views you rarely find. Quiet, peaceful, and a perfect place to unwind or entertain. Homes with this combination of layout, finish, and setting don't sit. Schedule your showing and bring your buyers before it's gone. Seller is related to Listing Agent.

414 Pueblo Ct, Winchester

$285,000

Welcome home to this beautifully reimagined property in Winchester! Originally built in 1945, this 1.5-story home has been completely transformed from the ground up, offering the perfect blend of classic charm and modern peace of mind. With approximately 1,838 square feet, this home has been fully gutted to the studs and thoughtfully rebuilt—featuring all-new electrical, plumbing, HVAC system, water heater, roof, drywall, and updated electric panel. Even the appliances are brand new, giving buyers the confidence of truly move-in ready living. The inviting exterior showcases a welcoming covered front porch, perfect for relaxing evenings, while inside you'll find a fresh, clean slate ready to make your own. The unfinished basement provides excellent storage or future expansion potential and includes a convenient one-car garage. Ideally located near schools and with easy access to the interstate, this home offers both comfort and convenience. If you've been searching for a property where all the hard work has already been done—this could be the one.

5 Beds ⋅ 2 Baths ⋅ 26007906 MLS

Welcome home to this beautifully reimagined property in Winchester! Originally built in 1945, this 1.5-story home has been completely transformed from the ground up, offering the perfect blend of classic charm and modern peace of mind. With approximately 1,838 square feet, this home has been fully gutted to the studs and thoughtfully rebuilt—featuring all-new electrical, plumbing, HVAC system, water heater, roof, drywall, and updated electric panel. Even the appliances are brand new, giving buyers the confidence of truly move-in ready living. The inviting exterior showcases a welcoming covered front porch, perfect for relaxing evenings, while inside you'll find a fresh, clean slate ready to make your own. The unfinished basement provides excellent storage or future expansion potential and includes a convenient one-car garage. Ideally located near schools and with easy access to the interstate, this home offers both comfort and convenience. If you've been searching for a property where all the hard work has already been done—this could be the one.

426 E Broadway St, Winchester

$280,000

Outstanding opportunity for investors or owner-occupants! This beautifully updated duplex is located in Winchester's desirable Stuarts Addition and offers two spacious units, each featuring approximately 1,545 square feet with 3 bedrooms and 2 full bathrooms. Both units have been thoughtfully renovated and feature hardwood flooring throughout the main living areas with tile in the wet areas for style and durability. Major improvements include newer HVAC systems, roof, stainless steel appliances, windows, doors, vinyl siding, and fresh interior paint, providing true move-in-ready convenience and low-maintenance ownership. Ideally located within walking distance of College Park and historic downtown Winchester, this property also offers quick access to I-64, shopping, restaurants, schools, and everyday amenities. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other, this well-maintained duplex offers the perfect combination of modern updates, strong income potential, and an exceptional location.

6 Beds ⋅ 4 Baths ⋅ 26019498 MLS

Outstanding opportunity for investors or owner-occupants! This beautifully updated duplex is located in Winchester's desirable Stuarts Addition and offers two spacious units, each featuring approximately 1,545 square feet with 3 bedrooms and 2 full bathrooms. Both units have been thoughtfully renovated and feature hardwood flooring throughout the main living areas with tile in the wet areas for style and durability. Major improvements include newer HVAC systems, roof, stainless steel appliances, windows, doors, vinyl siding, and fresh interior paint, providing true move-in-ready convenience and low-maintenance ownership. Ideally located within walking distance of College Park and historic downtown Winchester, this property also offers quick access to I-64, shopping, restaurants, schools, and everyday amenities. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other, this well-maintained duplex offers the perfect combination of modern updates, strong income potential, and an exceptional location.

21 Beckner St, Winchester

$280,000

PRICE REDUCTION!!! Perfect for investment or primary residence. Welcome home to this cozy cute FOUR bedroom house with 2 full bath/ 1 half bath! Rare to find- Primary bedroom and full bath on first floor. Large living area with plenty of sunlight through insulated windows and skylights. This open floorpan also showcases a nice open staircase that overlooks the main floor. Upstairs are 3 additional bedrooms and a full bathroom. Fenced yard and covered patio to enjoy. Extra wide driveway to accommodate 2 vehicles leading to a 1-car garage. **Selling house as is but inspections are welcome

4 Beds ⋅ 3 Baths ⋅ 26004861 MLS

PRICE REDUCTION!!! Perfect for investment or primary residence. Welcome home to this cozy cute FOUR bedroom house with 2 full bath/ 1 half bath! Rare to find- Primary bedroom and full bath on first floor. Large living area with plenty of sunlight through insulated windows and skylights. This open floorpan also showcases a nice open staircase that overlooks the main floor. Upstairs are 3 additional bedrooms and a full bathroom. Fenced yard and covered patio to enjoy. Extra wide driveway to accommodate 2 vehicles leading to a 1-car garage. **Selling house as is but inspections are welcome

327 Newcastle Ln, Winchester

$278,000

Welcome to 304 Sandra Drive. This 4 bedroom, 2 bath ranch is quietly nestled within the desirable Westmeade subdivision. While location is obvious, this property features many updates that can be seen throughout. Multiple primary bedroom with on-suites, large backyard, new HVAC and water heater, including duct work, and so much more. Schedule your showing today!

4 Beds ⋅ 3 Baths ⋅ 26016975 MLS

Welcome to 304 Sandra Drive. This 4 bedroom, 2 bath ranch is quietly nestled within the desirable Westmeade subdivision. While location is obvious, this property features many updates that can be seen throughout. Multiple primary bedroom with on-suites, large backyard, new HVAC and water heater, including duct work, and so much more. Schedule your showing today!

304 Sandra Dr, Winchester

$277,500

Built in 2020, this well-maintained Craftsman-style ranch offers the benefits of newer construction without the wait or added cost. Located in Winchester, KY, this home combines comfort, functionality, and convenience in one clean package. Featuring 3 bedrooms and 2 full baths, the layout is designed for everyday living with an open feel and thoughtful flow throughout. The kitchen includes stainless steel appliances, while the main living areas showcase durable laminate plank flooring with carpeted bedrooms for added comfort. Enjoy both a covered front porch and covered rear patio, perfect for relaxing and taking in the surrounding views. A 2-car garage adds additional storage and practicality. Conveniently located just minutes from downtown Winchester, shopping, restaurants, and with easy access to Hamburg in Lexington, this home offers the ideal balance of small-town living with nearby amenities.

3 Beds ⋅ 2 Baths ⋅ 26010021 MLS

Built in 2020, this well-maintained Craftsman-style ranch offers the benefits of newer construction without the wait or added cost. Located in Winchester, KY, this home combines comfort, functionality, and convenience in one clean package. Featuring 3 bedrooms and 2 full baths, the layout is designed for everyday living with an open feel and thoughtful flow throughout. The kitchen includes stainless steel appliances, while the main living areas showcase durable laminate plank flooring with carpeted bedrooms for added comfort. Enjoy both a covered front porch and covered rear patio, perfect for relaxing and taking in the surrounding views. A 2-car garage adds additional storage and practicality. Conveniently located just minutes from downtown Winchester, shopping, restaurants, and with easy access to Hamburg in Lexington, this home offers the ideal balance of small-town living with nearby amenities.

403 Pueblo Ct, Winchester

$277,000

Welcome to 20 Bon Haven Avenue, a beautifully renovated 4-bedroom, 3 full bathroom home ideally located directly across from the new Legacy Grove Park in Winchester, KY. This spacious residence blends modern upgrades with timeless charm, offering the perfect retreat for families and entertainers alike. Step inside to find a bright and airy open floor plan, highlighted by brand-new plumbing and electrical systems for peace of mind. The heart of the home features a sleek, contemporary kitchen with gorgeous quartz countertops, cabinetry, and stainless steel appliances - ideal for cooking and gathering. The primary bedroom is on the first floor. With three additional bedrooms upstairs. Each of the four generously sized bedrooms provides ample space and natural light, while the three fully updated bathrooms showcase stylish fixtures and finishes. With every detail thoughtfully upgraded, this home offers move-in-ready convenience in a prime location. Enjoy the benefits of being just steps away from walking trails, playgrounds, and green space at Legacy Grove Park, while also being minutes from local shops, restaurants, and schools. Don't miss your chance to own this rare gem in one of Winchester's most desirable neighborhoods!

4 Beds ⋅ 3 Baths ⋅ 26011883 MLS

Welcome to 20 Bon Haven Avenue, a beautifully renovated 4-bedroom, 3 full bathroom home ideally located directly across from the new Legacy Grove Park in Winchester, KY. This spacious residence blends modern upgrades with timeless charm, offering the perfect retreat for families and entertainers alike. Step inside to find a bright and airy open floor plan, highlighted by brand-new plumbing and electrical systems for peace of mind. The heart of the home features a sleek, contemporary kitchen with gorgeous quartz countertops, cabinetry, and stainless steel appliances - ideal for cooking and gathering. The primary bedroom is on the first floor. With three additional bedrooms upstairs. Each of the four generously sized bedrooms provides ample space and natural light, while the three fully updated bathrooms showcase stylish fixtures and finishes. With every detail thoughtfully upgraded, this home offers move-in-ready convenience in a prime location. Enjoy the benefits of being just steps away from walking trails, playgrounds, and green space at Legacy Grove Park, while also being minutes from local shops, restaurants, and schools. Don't miss your chance to own this rare gem in one of Winchester's most desirable neighborhoods!

20 Bon Haven Ave, Winchester

$275,000

Nicely updated split-level home with a large, fenced backyard, located on a quiet cul-de-sac. This energy-efficient home boasts a brand-new HVAC system, a recently replaced roof, fresh paint and stylish new LVP flooring throughout the house. The large kitchen has updated countertops and cabinets, as well as brand-new stainless steel appliances with three-year warranties. Both bathrooms have been updated with new floors and vanities and the upstairs bathroom has a double vanity and fresh new tiles. There's plenty of room in this house, with three bedrooms and the option of a fourth downstairs. And get your cars out of the rain and snow in the large double garage. Many amenities like shops and restaurants are within walking distance and Lexington's Hamburg Pavilion is only 11 miles away. This home is move-in ready! Property currently under contingency with 48-hour kick-out clause but welcomes showings.

3 Beds ⋅ 2 Baths ⋅ 26003170 MLS

Nicely updated split-level home with a large, fenced backyard, located on a quiet cul-de-sac. This energy-efficient home boasts a brand-new HVAC system, a recently replaced roof, fresh paint and stylish new LVP flooring throughout the house. The large kitchen has updated countertops and cabinets, as well as brand-new stainless steel appliances with three-year warranties. Both bathrooms have been updated with new floors and vanities and the upstairs bathroom has a double vanity and fresh new tiles. There's plenty of room in this house, with three bedrooms and the option of a fourth downstairs. And get your cars out of the rain and snow in the large double garage. Many amenities like shops and restaurants are within walking distance and Lexington's Hamburg Pavilion is only 11 miles away. This home is move-in ready! Property currently under contingency with 48-hour kick-out clause but welcomes showings.

211 Lindsey Ct, Winchester

$275,000

This well-kept split-level home in the Westmeade neighborhood offers a practical layout in a location that's close to the bypass, restaurants, and shopping. Upstairs, you'll find a roomy living area with a freestanding electric fireplace, along with an open kitchen and dining space. There are also three bedrooms and a full shared bathroom on this level. Downstairs, you'll find a finished basement that works well as a family room or den, along with a half bath and laundry area. It also offers direct access to the one-car garage, which leads out to the backyard for added convenience. The home includes tile flooring in the bathrooms, laminate throughout the main living spaces, and carpet in the bedrooms and basement. The HVAC system is about four years old per the seller. Outside, there's a backyard fire pit and swing that will stay, along with an extra parking pad next to the garage.

3 Beds ⋅ 2 Baths ⋅ 26007559 MLS

This well-kept split-level home in the Westmeade neighborhood offers a practical layout in a location that's close to the bypass, restaurants, and shopping. Upstairs, you'll find a roomy living area with a freestanding electric fireplace, along with an open kitchen and dining space. There are also three bedrooms and a full shared bathroom on this level. Downstairs, you'll find a finished basement that works well as a family room or den, along with a half bath and laundry area. It also offers direct access to the one-car garage, which leads out to the backyard for added convenience. The home includes tile flooring in the bathrooms, laminate throughout the main living spaces, and carpet in the bedrooms and basement. The HVAC system is about four years old per the seller. Outside, there's a backyard fire pit and swing that will stay, along with an extra parking pad next to the garage.

402 Harney Dr, Winchester

$274,900

Good things absolutely do come in affordable packages! This well maintained 3 bed 2.5 bath home on the Lexington side of Winchester has a beautiful back yard with a deck and built-in porch swing. It is privacy fenced and ready for you to enjoy, but not at the expense of access to town! With shopping right around the corner, and access to the highway not far off, this home would be great for someone who already loves Winchester, or a commuter from Lexington who is looking for more bang for their buck. This home is competitively priced per square foot and boasts a young roof, fault free systems, and easy to manage layout. The generous primary bedroom has an oversized walk in closet, and one of the additional bedrooms has a walk in closet, assuring storage is no issue. Enjoy your peace and quiet, or bring the kids and dogs- this set up is turnkey for everyone!

3 Beds ⋅ 3 Baths ⋅ 26015181 MLS

Good things absolutely do come in affordable packages! This well maintained 3 bed 2.5 bath home on the Lexington side of Winchester has a beautiful back yard with a deck and built-in porch swing. It is privacy fenced and ready for you to enjoy, but not at the expense of access to town! With shopping right around the corner, and access to the highway not far off, this home would be great for someone who already loves Winchester, or a commuter from Lexington who is looking for more bang for their buck. This home is competitively priced per square foot and boasts a young roof, fault free systems, and easy to manage layout. The generous primary bedroom has an oversized walk in closet, and one of the additional bedrooms has a walk in closet, assuring storage is no issue. Enjoy your peace and quiet, or bring the kids and dogs- this set up is turnkey for everyone!

136 Sturbridge Ln, Winchester

$274,000

Welcome to 158 Cabin Creek Heights, where comfortable one-level living meets a peaceful country setting just minutes from Winchester! This 3-bedroom, 2-bath ranch offers 1,580 square feet with a functional, easy-flowing layout and plenty of natural light throughout. The spacious primary suite features a walk-in closet and private bath, while the additional bedrooms offer flexibility for guests, a home office, or growing needs. Outside, enjoy nearly half an acre with room to relax, entertain, garden, or simply take in the surrounding rural views. An attached garage adds everyday convenience, and the location offers the quiet feel of country living while keeping Winchester amenities and I-64 within easy reach. A great opportunity for buyers looking for space, simplicity, and a little breathing room!

3 Beds ⋅ 2 Baths ⋅ 26022065 MLS

Welcome to 158 Cabin Creek Heights, where comfortable one-level living meets a peaceful country setting just minutes from Winchester! This 3-bedroom, 2-bath ranch offers 1,580 square feet with a functional, easy-flowing layout and plenty of natural light throughout. The spacious primary suite features a walk-in closet and private bath, while the additional bedrooms offer flexibility for guests, a home office, or growing needs. Outside, enjoy nearly half an acre with room to relax, entertain, garden, or simply take in the surrounding rural views. An attached garage adds everyday convenience, and the location offers the quiet feel of country living while keeping Winchester amenities and I-64 within easy reach. A great opportunity for buyers looking for space, simplicity, and a little breathing room!

158 Cabin Creek Hts, Winchester

$273,750

The ranch home at 116 Sturbridge Lane in Winchester, KY has 3 bedrooms, 2 full bathrooms, an eat-in kitchen, large living room, laundry room and 2 car garage. The home has been lovingly cared for and features multiple upgrades. Situated behind Lowe's, it offers easy access to dining, shopping, the by-pass, and medical & educational facilities.

3 Beds ⋅ 2 Baths ⋅ 26011782 MLS

The ranch home at 116 Sturbridge Lane in Winchester, KY has 3 bedrooms, 2 full bathrooms, an eat-in kitchen, large living room, laundry room and 2 car garage. The home has been lovingly cared for and features multiple upgrades. Situated behind Lowe's, it offers easy access to dining, shopping, the by-pass, and medical & educational facilities.

116 Sturbridge Ln, Winchester

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