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A beautiful home waiting on you to come grab it. It has new kitchen cabinets. The owners hooked the gas back up to the home and everything is gas except the 3-year-old electric water heater. The heating and cooling system is less than 2 years old. They added canned lighting throughout the home to brighten up the home. It also has a brand-new garage that was built that is a 18x21 with electric.

4 Beds ⋅ 3 Baths ⋅ 26001286 MLS

A beautiful home waiting on you to come grab it. It has new kitchen cabinets. The owners hooked the gas back up to the home and everything is gas except the 3-year-old electric water heater. The heating and cooling system is less than 2 years old. They added canned lighting throughout the home to brighten up the home. It also has a brand-new garage that was built that is a 18x21 with electric.

313 Carolina Ave, Winchester

$260,000

This phenomenal property has had so many updates including the addition of a full bath on the second floor, an updated electric panel, new wiring throughout, added electrical outlets, all new plumbing, a heat pump for the second floor (there is gas heat on the first floor) and a walk-in closet in the primary bedroom on the first floor. The owners have given meticulous attention to every beautiful detail in this 3 bedroom, 2 bath home with a stunning front porch and a backyard that rivals an English garden. Within walking distance to the library, College Park ad historic downtown Winchester, this dream home can be yours.

3 Beds ⋅ 2 Baths ⋅ 25500165 MLS

This phenomenal property has had so many updates including the addition of a full bath on the second floor, an updated electric panel, new wiring throughout, added electrical outlets, all new plumbing, a heat pump for the second floor (there is gas heat on the first floor) and a walk-in closet in the primary bedroom on the first floor. The owners have given meticulous attention to every beautiful detail in this 3 bedroom, 2 bath home with a stunning front porch and a backyard that rivals an English garden. Within walking distance to the library, College Park ad historic downtown Winchester, this dream home can be yours.

113 Olde Potomac Ave, Winchester

$260,000

Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready property offers 4 bedrooms, an updated bathroom, a welcoming living room with a decorative (non-working) fireplace, and a cozy den featuring preserved French doors. The foyer leads to a beautifully painted staircase and second floor, while the spacious dining room and kitchen showcase custom painted cabinetry, stainless steel appliances, and a pantry. A large laundry room doubles as a walk-in closet for added convenience. Enjoy relaxing mornings on the wrap-around front porch with brick accents and composite steps, or unwind on the rear sunporch overlooking a vinyl-fenced yard complete with a patio area perfect for a fire pit and a 10X17 shed. The main bedroom is located on the first floor, with three additional bedrooms and a bonus room upstairs. Thoughtful touches like modern fixtures, fresh paint, exquisite wallpaper, and newly painted wood flooring elevate the entire home. With large rear parking and a prime location in the heart of downtown Winchester, you'll be within walking distance to local shops, dining, and upcoming festivals. The current owner will surely miss the convenience and wonderful neighbors and is confident the next owners will fall in love just as deeply. This is one you have to see! ONE year home warranty to buyer at closing.

4 Beds ⋅ 1 Baths ⋅ 26021028 MLS

Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready property offers 4 bedrooms, an updated bathroom, a welcoming living room with a decorative (non-working) fireplace, and a cozy den featuring preserved French doors. The foyer leads to a beautifully painted staircase and second floor, while the spacious dining room and kitchen showcase custom painted cabinetry, stainless steel appliances, and a pantry. A large laundry room doubles as a walk-in closet for added convenience. Enjoy relaxing mornings on the wrap-around front porch with brick accents and composite steps, or unwind on the rear sunporch overlooking a vinyl-fenced yard complete with a patio area perfect for a fire pit and a 10X17 shed. The main bedroom is located on the first floor, with three additional bedrooms and a bonus room upstairs. Thoughtful touches like modern fixtures, fresh paint, exquisite wallpaper, and newly painted wood flooring elevate the entire home. With large rear parking and a prime location in the heart of downtown Winchester, you'll be within walking distance to local shops, dining, and upcoming festivals. The current owner will surely miss the convenience and wonderful neighbors and is confident the next owners will fall in love just as deeply. This is one you have to see! ONE year home warranty to buyer at closing.

162 French Ave, Winchester

$260,000

Excellent investment opportunity featuring two income-producing buildings on one lot, offered together as a package deal. This unique multifamily property includes a triplex and a separate duplex, making it ideal for investors looking to expand their portfolio with multiple units in one purchase. The triplex (Building A) consists of three units: Unit A-1: 2 bedrooms, 1 bathroom Unit A-2: 1 bedroom, 1 bathroom Unit A-3: Office/studio-style apartment with 1 bedroom and 1 bathroom The duplex (Building B) offers two additional units: Unit B-1: 2 bedrooms, 1 bathroom Unit B-2: 2 bedrooms, 1 bathroom With five total units, this property provides strong income potential and flexibility for a variety of investment strategies. A recent appraisal came in at $320,000, and the property is priced below appraised value, creating built-in equity from day one.Great opportunity for investors seeking a solid multifamily asset with upside. Call today to schedule your private showing.

8 Beds ⋅ 5 Baths ⋅ 26002633 MLS

Excellent investment opportunity featuring two income-producing buildings on one lot, offered together as a package deal. This unique multifamily property includes a triplex and a separate duplex, making it ideal for investors looking to expand their portfolio with multiple units in one purchase. The triplex (Building A) consists of three units: Unit A-1: 2 bedrooms, 1 bathroom Unit A-2: 1 bedroom, 1 bathroom Unit A-3: Office/studio-style apartment with 1 bedroom and 1 bathroom The duplex (Building B) offers two additional units: Unit B-1: 2 bedrooms, 1 bathroom Unit B-2: 2 bedrooms, 1 bathroom With five total units, this property provides strong income potential and flexibility for a variety of investment strategies. A recent appraisal came in at $320,000, and the property is priced below appraised value, creating built-in equity from day one.Great opportunity for investors seeking a solid multifamily asset with upside. Call today to schedule your private showing.

144 Holly Ave, Winchester

$259,500

Location is key! Searching for your first home or thinking of downsizing? Priced right with stylish upgrades and style. This 3-bedroom 2 bath updated brick is ready for you to start enjoying home ownership. This gem has a new roof, new flooring throughout, new kitchen quartz countertop with a range backsplash, new doors, updated lighting, Shewin Williams paint throughout, updated bathrooms with a new shower, a floating vanity a new quartz vanity top. Located in an established neighborhood and you will enjoy the privacy of the fenced backyard. I would love to answer all of your new home ownership questions and schedule a home tour.

3 Beds ⋅ 2 Baths ⋅ 26022796 MLS

Location is key! Searching for your first home or thinking of downsizing? Priced right with stylish upgrades and style. This 3-bedroom 2 bath updated brick is ready for you to start enjoying home ownership. This gem has a new roof, new flooring throughout, new kitchen quartz countertop with a range backsplash, new doors, updated lighting, Shewin Williams paint throughout, updated bathrooms with a new shower, a floating vanity a new quartz vanity top. Located in an established neighborhood and you will enjoy the privacy of the fenced backyard. I would love to answer all of your new home ownership questions and schedule a home tour.

503 Kimberly Dr, Winchester

$259,000

Charming, Move-In Ready Ranch with Updates & Fenced Yard! Welcome home to this super cute and well-maintained 3-bedroom, 2-bath ranch offering easy one-level living and a smart, functional layout. Close to shopping and the interstate for easy commutes. Recent improvements include a brand-new roof, fresh interior paint throughout, a new garage door and opener, and a new stainless-steel appliance package in the kitchenâ€”so the big-ticket items are already done for you. The home features durable vinyl plank flooring throughout, providing a clean, modern look and easy maintenance. An attached one-car garage adds everyday convenience, while the fully fenced backyard is perfect for pets, play, or relaxing outdoors. Whether you're a first-time buyer, downsizing, or looking for a turnkey investment, this home checks all the boxes: updated, affordable, and truly move-in ready. Don't miss this one!

3 Beds ⋅ 2 Baths ⋅ 26002092 MLS

Charming, Move-In Ready Ranch with Updates & Fenced Yard! Welcome home to this super cute and well-maintained 3-bedroom, 2-bath ranch offering easy one-level living and a smart, functional layout. Close to shopping and the interstate for easy commutes. Recent improvements include a brand-new roof, fresh interior paint throughout, a new garage door and opener, and a new stainless-steel appliance package in the kitchenâ€”so the big-ticket items are already done for you. The home features durable vinyl plank flooring throughout, providing a clean, modern look and easy maintenance. An attached one-car garage adds everyday convenience, while the fully fenced backyard is perfect for pets, play, or relaxing outdoors. Whether you're a first-time buyer, downsizing, or looking for a turnkey investment, this home checks all the boxes: updated, affordable, and truly move-in ready. Don't miss this one!

414 Wellington Way, Winchester

$259,000

Welcome to this spacious 4-bedroom, 2 bath home offering plenty of room to grow and make your own. With generous living areas and a functional layout, this property is perfect for those seeking space, comfort and opportunity. The home features a 2-car attached garage along with an additional 676 SF detached 2-car garage, providing ample room for vehicles, storage or a workshop. Outside you will find a nice yard with plenty of space for outdoor activities. While the home does need some updating, it presents a fantastic opportunity for buyers to add their personal touch and build equity. With solid bones and great potential, this property is ideal for investors or homeowners ready to create their dream space. Inspections are welcome but home is being sold as is.

4 Beds ⋅ 2 Baths ⋅ 26009398 MLS

Welcome to this spacious 4-bedroom, 2 bath home offering plenty of room to grow and make your own. With generous living areas and a functional layout, this property is perfect for those seeking space, comfort and opportunity. The home features a 2-car attached garage along with an additional 676 SF detached 2-car garage, providing ample room for vehicles, storage or a workshop. Outside you will find a nice yard with plenty of space for outdoor activities. While the home does need some updating, it presents a fantastic opportunity for buyers to add their personal touch and build equity. With solid bones and great potential, this property is ideal for investors or homeowners ready to create their dream space. Inspections are welcome but home is being sold as is.

86 Bon-Haven Ave, Winchester

$257,400

A timeless brick ranch in one of Winchester's most established neighborhoods on a corner lot. This 3 bedroom, 2.5 bath home offers two living areas and a cozy fireplace. Spacious backyard, covered front porch, and a wrap-around driveway for a private entrance. All just minutes from downtown, schools, and I-64. The home combines classic comfort, location, and room to grow on a walk-out basement. As-Is, inspections welcomed.

3 Beds ⋅ 3 Baths ⋅ 25500099 MLS

A timeless brick ranch in one of Winchester's most established neighborhoods on a corner lot. This 3 bedroom, 2.5 bath home offers two living areas and a cozy fireplace. Spacious backyard, covered front porch, and a wrap-around driveway for a private entrance. All just minutes from downtown, schools, and I-64. The home combines classic comfort, location, and room to grow on a walk-out basement. As-Is, inspections welcomed.

103 Hampton Ave, Winchester

$256,000

Home is quietly nestled within the Wesleyan Park subdivision just off the Winchester Bypass. While convenient location is obvious this home boast many updates throughout. Including flooring, appliances, New roof, HVAC, Water heater and so much more. Schedule your showing while you can!

4 Beds ⋅ 2 Baths ⋅ 25016651 MLS

Home is quietly nestled within the Wesleyan Park subdivision just off the Winchester Bypass. While convenient location is obvious this home boast many updates throughout. Including flooring, appliances, New roof, HVAC, Water heater and so much more. Schedule your showing while you can!

306 Snowden Dr, Winchester

$255,580

Welcome to 108 Milwood Drive\! Nestled in one of Winchester's most desirable neighborhoods, this well\-maintained 3\-bedroom, 2\-bath ranch offers a functional floor plan and peaceful backyard setting\. The spacious living room features a gas log fireplace, while the primary suite includes a private en suite bath\. A cozy den opens to a wooden deck overlooking the fenced backyard and wooded views—perfect for relaxing or entertaining\. The semi\-finished walkout basement provides additional living space and a rear\-entry garage for added convenience\. Don't miss this opportunity to own a home that combines comfort, privacy, and a great location\!

3 Beds ⋅ 2 Baths ⋅ 26019908 MLS

Welcome to 108 Milwood Drive\! Nestled in one of Winchester's most desirable neighborhoods, this well\-maintained 3\-bedroom, 2\-bath ranch offers a functional floor plan and peaceful backyard setting\. The spacious living room features a gas log fireplace, while the primary suite includes a private en suite bath\. A cozy den opens to a wooden deck overlooking the fenced backyard and wooded views—perfect for relaxing or entertaining\. The semi\-finished walkout basement provides additional living space and a rear\-entry garage for added convenience\. Don't miss this opportunity to own a home that combines comfort, privacy, and a great location\!

108 Milwood Dr, Winchester

$255,000

Step into modern comfort just minutes from the heart of downtown Winchester. This nearly new home blends contemporary style with timeless charm. Featuring bright, open living spaces, and thoughtful upgrades throughout, it offers a move-in-ready opportunity in one of Winchester's most convenient locations.

3 Beds ⋅ 3 Baths ⋅ 25507377 MLS

Step into modern comfort just minutes from the heart of downtown Winchester. This nearly new home blends contemporary style with timeless charm. Featuring bright, open living spaces, and thoughtful upgrades throughout, it offers a move-in-ready opportunity in one of Winchester's most convenient locations.

120 Jackson St, Winchester

$255,000

Welcome to this charming 3-bedroom, 1.5-bath home situated on a lovely corner lot. Step inside to discover a well-maintained interior with a thoughtful layout that flows effortlessly from room to room. The cozy living area opens to the dining space. You'll also find two versatile flex spaces, each filled with natural light from large windows-perfect for a home office, playroom, or creative studio. The kitchen and adjoining butler's pantry showcase the home's timeless craftsmanship, featuring original built-in cabinetry that blends charm with functionality. A convenient first-floor laundry and mudroom add to the home's practicality. Outside, enjoy a private, fully fenced yard, perfect for pets, play, or simply relaxing outdoors. The unfinished basement with walk-out access provides ample storage. Combining historic charm with modern comfort, this home is ready to welcome its next owners!

3 Beds ⋅ 2 Baths ⋅ 25505142 MLS

Welcome to this charming 3-bedroom, 1.5-bath home situated on a lovely corner lot. Step inside to discover a well-maintained interior with a thoughtful layout that flows effortlessly from room to room. The cozy living area opens to the dining space. You'll also find two versatile flex spaces, each filled with natural light from large windows-perfect for a home office, playroom, or creative studio. The kitchen and adjoining butler's pantry showcase the home's timeless craftsmanship, featuring original built-in cabinetry that blends charm with functionality. A convenient first-floor laundry and mudroom add to the home's practicality. Outside, enjoy a private, fully fenced yard, perfect for pets, play, or simply relaxing outdoors. The unfinished basement with walk-out access provides ample storage. Combining historic charm with modern comfort, this home is ready to welcome its next owners!

357 Crescent Ave, Winchester

$255,000

Step into this 4-bedroom, 2 full bath split-foyer home, perfectly designed for comfortable everyday living. The upper level features three generously sized bedrooms, a full bath, a bright living room, kitchen, and dining area—ideal for gathering with family and friends. Just off the kitchen, enjoy easy access to the covered deck overlooking a spacious backyard. The lower level offers even more living space with a fourth bedroom, full bath, cozy family room with fireplace, and ample storage—perfect for guests, a home office or work out room. With a little personal TLC and your own creative touches, this home is ready to be transformed into a warm and welcoming family home. A wonderful opportunity to make it truly your own! Sold as is.

4 Beds ⋅ 2 Baths ⋅ 25508113 MLS

Step into this 4-bedroom, 2 full bath split-foyer home, perfectly designed for comfortable everyday living. The upper level features three generously sized bedrooms, a full bath, a bright living room, kitchen, and dining area—ideal for gathering with family and friends. Just off the kitchen, enjoy easy access to the covered deck overlooking a spacious backyard. The lower level offers even more living space with a fourth bedroom, full bath, cozy family room with fireplace, and ample storage—perfect for guests, a home office or work out room. With a little personal TLC and your own creative touches, this home is ready to be transformed into a warm and welcoming family home. A wonderful opportunity to make it truly your own! Sold as is.

35 Cherokee Ct, Winchester

$255,000

Located in Winchester, this 4-bedroom, 2-bath home offers approximately 2,417 square feet of living space with room to spread out both indoors and out. The home features a spacious living room with a fireplace, providing a comfortable central gathering area. Multiple bedrooms offer flexibility for guests, home office space, or changing household needs. Recent updates include a renovated kitchen and the addition of a bathroom with new plumbing (2021), along with a new HVAC system installed in 2020. The property also features a tall crawl space with walk-in access, offering additional usable storage or access space. Conveniently situated near local amenities, shopping, and dining, this property presents an opportunity for buyers seeking space, functionality, and a convenient Winchester location.

4 Beds ⋅ 2 Baths ⋅ 26005196 MLS

Located in Winchester, this 4-bedroom, 2-bath home offers approximately 2,417 square feet of living space with room to spread out both indoors and out. The home features a spacious living room with a fireplace, providing a comfortable central gathering area. Multiple bedrooms offer flexibility for guests, home office space, or changing household needs. Recent updates include a renovated kitchen and the addition of a bathroom with new plumbing (2021), along with a new HVAC system installed in 2020. The property also features a tall crawl space with walk-in access, offering additional usable storage or access space. Conveniently situated near local amenities, shopping, and dining, this property presents an opportunity for buyers seeking space, functionality, and a convenient Winchester location.

104 Jackson Ferry Rd, Winchester

$255,000

A spacious Ranch style home with many recent updates. With 4 bedrooms and 2 bath you'll find plenty of space for the everyone. With new laminate flooring, several new doors, and new paint throughout; this home is move in ready! Other updates include a new shower in the master bath, new microwave, new tile in the Utility room, new island top, new shelving in the walk in closet, and new gutters. Did I mention the owners are leaving all appliances including the washer and dryer? Come take a look at this beauty today! It could be your forever home.

4 Beds ⋅ 2 Baths ⋅ 26005860 MLS

A spacious Ranch style home with many recent updates. With 4 bedrooms and 2 bath you'll find plenty of space for the everyone. With new laminate flooring, several new doors, and new paint throughout; this home is move in ready! Other updates include a new shower in the master bath, new microwave, new tile in the Utility room, new island top, new shelving in the walk in closet, and new gutters. Did I mention the owners are leaving all appliances including the washer and dryer? Come take a look at this beauty today! It could be your forever home.

504 Harvard Dr, Winchester

$254,000

Welcome home to this beautifully remodeled 3 bedroom, 2 bathroom brick ranch in a well-established neighborhood. Nearly everything is new, including the roof, plumbing, and kitchen appliances. You'll love the refinished hardwood floors and stylish fixtures throughout. The kitchen features gorgeous granite countertops and an island with bar seating. One bathroom offers a tiled shower with a built-in niche, while the second bath includes a convenient stand-up shower. The primary bedroom has a large walk-in closet with custom shelving and drawers. The cozy den provides a second living area. Outside, enjoy the covered carport and good-sized back yard. Just steps from Legacy Grove Park with its walking trail, dog park, and playground, this home blends modern updates with timeless charm! Move-in ready and waiting for you!

3 Beds ⋅ 2 Baths ⋅ 25019205 MLS

Welcome home to this beautifully remodeled 3 bedroom, 2 bathroom brick ranch in a well-established neighborhood. Nearly everything is new, including the roof, plumbing, and kitchen appliances. You'll love the refinished hardwood floors and stylish fixtures throughout. The kitchen features gorgeous granite countertops and an island with bar seating. One bathroom offers a tiled shower with a built-in niche, while the second bath includes a convenient stand-up shower. The primary bedroom has a large walk-in closet with custom shelving and drawers. The cozy den provides a second living area. Outside, enjoy the covered carport and good-sized back yard. Just steps from Legacy Grove Park with its walking trail, dog park, and playground, this home blends modern updates with timeless charm! Move-in ready and waiting for you!

312 Forest Ave, Winchester

$253,000

Back on Market! Welcome to 363 South Main Street in the heart of downtown Winchester, KY—this spacious 3-bedroom, 2-bath home offers 2,142 square feet of character, updates, and convenience. Ideally located close to all local amenities and just 5 minutes from I-64, you'll enjoy easy access to shopping, dining, and commuting. The home features beautiful hardwood floors and an updated kitchen with plenty of cabinet space, perfect for everyday living and entertaining. Recent improvements include a new roof, soffit, and gutters, along with an updated HVAC system, fresh exterior paint, professional pressure washing, and refreshed landscaping—making this property truly move-in ready. A versatile loft space provides additional storage or future potential, while the covered front porch, back deck, and fenced backyard create the perfect setup for relaxing or hosting guests. This is a rare opportunity to own a well-updated home in a prime downtown location.

3 Beds ⋅ 2 Baths ⋅ 26009123 MLS

Back on Market! Welcome to 363 South Main Street in the heart of downtown Winchester, KY—this spacious 3-bedroom, 2-bath home offers 2,142 square feet of character, updates, and convenience. Ideally located close to all local amenities and just 5 minutes from I-64, you'll enjoy easy access to shopping, dining, and commuting. The home features beautiful hardwood floors and an updated kitchen with plenty of cabinet space, perfect for everyday living and entertaining. Recent improvements include a new roof, soffit, and gutters, along with an updated HVAC system, fresh exterior paint, professional pressure washing, and refreshed landscaping—making this property truly move-in ready. A versatile loft space provides additional storage or future potential, while the covered front porch, back deck, and fenced backyard create the perfect setup for relaxing or hosting guests. This is a rare opportunity to own a well-updated home in a prime downtown location.

363 S Main St, Winchester

$253,000

Private unrestricted 12-Acre Property in Winchester, KY - Convenient to Lexington & Red River Gorge This 3-bedroom, 2-bath single-family home with an office/flex room is situated on 12 acres in Winchester, KY, offering a combination of open and primarily wooded land. The property is located less than 40 minutes from Lexington and approximately 30 minutes from Red River Gorge. The home offers 1,960 square feet of living space Including a walk in pantry, A large Primary suite with a jetted tub. A functional layout suitable for a variety of living needs. The office/flex room provides additional usable space for a home office, hobby room, or guest area. Owners had High Speed Internet installed on the property in 2023. A 2-car garage provides vehicle and storage space. The acreage includes a mix of open and wooded land, blackberry bushes that produce summer berries, and a pear tree that produces fruit in the fall, along with established trails suitable for UTV riding or recreational use. The setting provides privacy and outdoor space while maintaining access to nearby amenities and recreational destinations. Schedule a showing to explore the home and land in person..

3 Beds ⋅ 2 Baths ⋅ 26000897 MLS

Private unrestricted 12-Acre Property in Winchester, KY - Convenient to Lexington & Red River Gorge This 3-bedroom, 2-bath single-family home with an office/flex room is situated on 12 acres in Winchester, KY, offering a combination of open and primarily wooded land. The property is located less than 40 minutes from Lexington and approximately 30 minutes from Red River Gorge. The home offers 1,960 square feet of living space Including a walk in pantry, A large Primary suite with a jetted tub. A functional layout suitable for a variety of living needs. The office/flex room provides additional usable space for a home office, hobby room, or guest area. Owners had High Speed Internet installed on the property in 2023. A 2-car garage provides vehicle and storage space. The acreage includes a mix of open and wooded land, blackberry bushes that produce summer berries, and a pear tree that produces fruit in the fall, along with established trails suitable for UTV riding or recreational use. The setting provides privacy and outdoor space while maintaining access to nearby amenities and recreational destinations. Schedule a showing to explore the home and land in person..

564 Trapp-Goffs Cor Rd, Winchester

$252,500

Lovely one level brick ranch on a corner lot conveniently located in the Meadows just off of McClure Rd. 3 bedroom, 2 full bath, attached garage, rear patio, beautiful yard with trees and a storage building out back.

3 Beds ⋅ 2 Baths ⋅ 25507197 MLS

Lovely one level brick ranch on a corner lot conveniently located in the Meadows just off of McClure Rd. 3 bedroom, 2 full bath, attached garage, rear patio, beautiful yard with trees and a storage building out back.

110 Albany Ln, Winchester

$252,000

Escape to your own slice of paradise on 4.06 private acres, complete with a peaceful pond perfect for relaxing or fishing. Discover this beautifully updated 3-bedroom, 2-bath home offering 1,356 sq. ft. of inviting, open-concept living. Built in 1973, this charming property features new flooring, a warm, welcoming fireplace, and a modern kitchen with stainless steel appliances. Enjoy added peace of mind with a security system, plus the convenience of a 1-car garage and private utility room. This home offers both comfort and convenience — the ideal blend of modern updates and serene country living.

3 Beds ⋅ 2 Baths ⋅ 25505744 MLS

Escape to your own slice of paradise on 4.06 private acres, complete with a peaceful pond perfect for relaxing or fishing. Discover this beautifully updated 3-bedroom, 2-bath home offering 1,356 sq. ft. of inviting, open-concept living. Built in 1973, this charming property features new flooring, a warm, welcoming fireplace, and a modern kitchen with stainless steel appliances. Enjoy added peace of mind with a security system, plus the convenience of a 1-car garage and private utility room. This home offers both comfort and convenience — the ideal blend of modern updates and serene country living.

4074 Ironworks Rd, Winchester

$250,000

Welcome home! This charming 3 bedroom, 2.5 bath property offers comfort and style with thoughtful updates, a 1-car garage, and a spacious fenced yard with covered deck. Enjoy a view of the large backyard from your eat-in kitchen that features a tiled backsplash and new appliances. Primary bedroom includes a new tiled shower and multiple closets. Second and third bedrooms conveniently share a full bath. Extensive updates include: Roof (2025), Dishwasher (2025), Microwave (2025), Deck (2025), Primary Bathroom Shower (2024), Flooring (Living Room and Kitchen 2021), 2 Car Driveway (2021), HVAC (2018), and Water Heater (2019).

3 Beds ⋅ 3 Baths ⋅ 25507056 MLS

Welcome home! This charming 3 bedroom, 2.5 bath property offers comfort and style with thoughtful updates, a 1-car garage, and a spacious fenced yard with covered deck. Enjoy a view of the large backyard from your eat-in kitchen that features a tiled backsplash and new appliances. Primary bedroom includes a new tiled shower and multiple closets. Second and third bedrooms conveniently share a full bath. Extensive updates include: Roof (2025), Dishwasher (2025), Microwave (2025), Deck (2025), Primary Bathroom Shower (2024), Flooring (Living Room and Kitchen 2021), 2 Car Driveway (2021), HVAC (2018), and Water Heater (2019).

208 Watercrest Way, Winchester

$250,000

Nicely updated and offering plenty of functional space, this home gives you flexibility and room to grow. The main living area flows into an updated kitchen featuring modern finishes, new appliances, butcher-block countertops, and convenient access to the sunroom. Enjoy your morning coffee in the oversized sunroom, then step out to the fully fenced backyard — great for chickens, kids, pets, gardening, or outdoor get-togethers. The partially finished basement adds even more usable space with a second living area and the potential for an additional bedroom, office, or hobby room. It's an ideal setup if you need versatility or plan to grow into the space over time. AI Pictures shown of unfinished area are virtually staged and with the storage closets removed. With several updates already completed, this home offers a solid opportunity to make it your own. Located close to schools, shopping, and Winchester conveniences, it's a great option for anyone looking for space and value!

3 Beds ⋅ 2 Baths ⋅ 25506127 MLS

Nicely updated and offering plenty of functional space, this home gives you flexibility and room to grow. The main living area flows into an updated kitchen featuring modern finishes, new appliances, butcher-block countertops, and convenient access to the sunroom. Enjoy your morning coffee in the oversized sunroom, then step out to the fully fenced backyard — great for chickens, kids, pets, gardening, or outdoor get-togethers. The partially finished basement adds even more usable space with a second living area and the potential for an additional bedroom, office, or hobby room. It's an ideal setup if you need versatility or plan to grow into the space over time. AI Pictures shown of unfinished area are virtually staged and with the storage closets removed. With several updates already completed, this home offers a solid opportunity to make it your own. Located close to schools, shopping, and Winchester conveniences, it's a great option for anyone looking for space and value!

21 Virginia Ave, Winchester

$250,000

Welcome home to your Kentucky River retreat! This freshly remodeled 2-bedroom, 2-bath charmer offers two inviting covered decks with beautiful river views, a fenced yard for pets or play and even a personal lift for easy access. Inside, enjoy warm, modern updates, with a bright open floor plan. All new flooring, kitchen, baths and much more! Perfect for full-time living or a peaceful getaway just minutes from town.

2 Beds ⋅ 2 Baths ⋅ 25504354 MLS

Welcome home to your Kentucky River retreat! This freshly remodeled 2-bedroom, 2-bath charmer offers two inviting covered decks with beautiful river views, a fenced yard for pets or play and even a personal lift for easy access. Inside, enjoy warm, modern updates, with a bright open floor plan. All new flooring, kitchen, baths and much more! Perfect for full-time living or a peaceful getaway just minutes from town.

174 Hidden Grove Ln, Winchester

$250,000

This updated and well-maintained property offers over 2,500 finished sq ft across two levels, ideal for a wide range of business opportunities. The main floor features 1,280 sq ft with a welcoming foyer/reception area, 4-5 private offices, a kitchen, and 2 half baths. The finished walkout basement adds another 1,280 sq ft of flexible space, complete with a large open area, half bath, storage room, and access to a secondary parking lot—perfect for hosting clients or separating business functions. Recent updates include resurfaced blacktop in the main parking lot (8 total spaces), exterior improvements, and clean, professional landscaping that enhances curb appeal. With its layout and two-story design, the property could easily accommodate a home office, daycare, dental or healthcare practice, professional services, or even two separate businesses. Move-in ready and full of potential—schedule your private tour today!

25018319 MLS

This updated and well-maintained property offers over 2,500 finished sq ft across two levels, ideal for a wide range of business opportunities. The main floor features 1,280 sq ft with a welcoming foyer/reception area, 4-5 private offices, a kitchen, and 2 half baths. The finished walkout basement adds another 1,280 sq ft of flexible space, complete with a large open area, half bath, storage room, and access to a secondary parking lot—perfect for hosting clients or separating business functions. Recent updates include resurfaced blacktop in the main parking lot (8 total spaces), exterior improvements, and clean, professional landscaping that enhances curb appeal. With its layout and two-story design, the property could easily accommodate a home office, daycare, dental or healthcare practice, professional services, or even two separate businesses. Move-in ready and full of potential—schedule your private tour today!

110 Vine St, Winchester

$250,000

Bring your vision to life on 12+ beautiful acres in Winchester! This 3-bedroom, 1-bath home offers the charm of a 1964 build and the opportunity to create your own private retreat. With plenty of room for gardens, animals, workshops, or expansion, this property is perfect for those dreaming of country living. Renovate the existing home or reimagine the space to fit your needs — the possibilities are wide open.

3 Beds ⋅ 1 Baths ⋅ 26004070 MLS

Bring your vision to life on 12+ beautiful acres in Winchester! This 3-bedroom, 1-bath home offers the charm of a 1964 build and the opportunity to create your own private retreat. With plenty of room for gardens, animals, workshops, or expansion, this property is perfect for those dreaming of country living. Renovate the existing home or reimagine the space to fit your needs — the possibilities are wide open.

280 Pine Ridge Rd, Winchester

$249,900

You will love the atmosphere of this remodeled 3 bedroom, 2 bath home located in a secluded location. The large privacy fenced back yard is perfect for the children or pets. Renovated kitchen includes granite countertops, new range, dishwasher , and refrigerator. Home has a full partially finished walk out basement. You will love the large outbuilding as well as storage closet off of carport.

3 Beds ⋅ 2 Baths ⋅ 26009360 MLS

You will love the atmosphere of this remodeled 3 bedroom, 2 bath home located in a secluded location. The large privacy fenced back yard is perfect for the children or pets. Renovated kitchen includes granite countertops, new range, dishwasher , and refrigerator. Home has a full partially finished walk out basement. You will love the large outbuilding as well as storage closet off of carport.

123 Sunset Hts, Winchester

$249,900

This classic brick ranch house is move-in ready and waiting for you to call it home! Take a step inside the front door to appreciate the gleaming laminate wood floors in the open concept living space. Around the corner, the beautiful kitchen cabinets and updated, stainless, kitchen appliances are ready for family meals and social gatherings around the dining table. In the full bath, you'll find a lovely tiled, walk-in shower with a rain shower head and new tile floors. Out the back door, you'll find an excellent outdoor living area on the back deck with space to grill out or relax on a quiet spring evening. With the oversized, detached 2 car garage, you can enjoy extra storage space as well as a hobby workspace. The exterior brick faÃƒÆ’Ã‚Â§ade, plus the newer roof, appliances, HVAC system, water heater and light fixtures make this home virtually maintenance free. Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ 26013480 MLS

This classic brick ranch house is move-in ready and waiting for you to call it home! Take a step inside the front door to appreciate the gleaming laminate wood floors in the open concept living space. Around the corner, the beautiful kitchen cabinets and updated, stainless, kitchen appliances are ready for family meals and social gatherings around the dining table. In the full bath, you'll find a lovely tiled, walk-in shower with a rain shower head and new tile floors. Out the back door, you'll find an excellent outdoor living area on the back deck with space to grill out or relax on a quiet spring evening. With the oversized, detached 2 car garage, you can enjoy extra storage space as well as a hobby workspace. The exterior brick faÃƒÆ’Ã‚Â§ade, plus the newer roof, appliances, HVAC system, water heater and light fixtures make this home virtually maintenance free. Schedule your private showing today!

17 Holiday Rd, Winchester

$249,900

Welcome to this beautifully remodeled 3 bedroom, 2 full bathroom home situated on a desirable corner lot. With 1,530 sq ft of living space, this home offers great combination of modern updates and comfortable living. Features Include 3 spacious bedrooms, 2 full bathrooms, Private master suite with ensuite bath, Fully remodeled interior, corner lot, Stainless appliances, full tiled showers and the list goes on. Schedule your showing today!

3 Beds ⋅ 2 Baths ⋅ 26004591 MLS

Welcome to this beautifully remodeled 3 bedroom, 2 full bathroom home situated on a desirable corner lot. With 1,530 sq ft of living space, this home offers great combination of modern updates and comfortable living. Features Include 3 spacious bedrooms, 2 full bathrooms, Private master suite with ensuite bath, Fully remodeled interior, corner lot, Stainless appliances, full tiled showers and the list goes on. Schedule your showing today!

1407 Ironworks Rd, Winchester

$249,900

Welcome home to this inviting 3 Bedroom 2 bath home situated on a spacious 0.41 Acre lot. This home offers the perfect blend of comfort and functionality that offers a well designed layout with ample living space. Step into the spacious living room where beautiful Hardwood floors add warmth, character,and timeless appeal. Perfect for relaxing with family or entertaining guests. The Master bedroom is also on the main floor complete with a spacious Bathroom. The heart of the home is the beautifully appointed kitchen featuring oak cabinets that provide both timeless charm and abundant storage. Equipped with All newer appliances, this kitchen offers the perfect combination of style and functionality. Adjacent to the kitchen the well appointed dining room creates an inviting space for family meals. Upstairs you will find two generously sized bedrooms that offer space for relaxation and storage. Serving the upper level is the huge bathroom featuring ample room to accommodate those busy mornings with ease. Step out on the brand-new back deck that creates an ideal space for taking in the beautiful views of the trees that line the back of the property. With Plenty of yard space this property Is perfect for enjoying family get together's or simply having the space for the kids to play. Combining classic charm, and a beautiful 0.41 Acre setting, this move-in-ready home is ready for its next owners!! Schedule your showing today and discover all it has to offer!

3 Beds ⋅ 2 Baths ⋅ 26014058 MLS

Welcome home to this inviting 3 Bedroom 2 bath home situated on a spacious 0.41 Acre lot. This home offers the perfect blend of comfort and functionality that offers a well designed layout with ample living space. Step into the spacious living room where beautiful Hardwood floors add warmth, character,and timeless appeal. Perfect for relaxing with family or entertaining guests. The Master bedroom is also on the main floor complete with a spacious Bathroom. The heart of the home is the beautifully appointed kitchen featuring oak cabinets that provide both timeless charm and abundant storage. Equipped with All newer appliances, this kitchen offers the perfect combination of style and functionality. Adjacent to the kitchen the well appointed dining room creates an inviting space for family meals. Upstairs you will find two generously sized bedrooms that offer space for relaxation and storage. Serving the upper level is the huge bathroom featuring ample room to accommodate those busy mornings with ease. Step out on the brand-new back deck that creates an ideal space for taking in the beautiful views of the trees that line the back of the property. With Plenty of yard space this property Is perfect for enjoying family get together's or simply having the space for the kids to play. Combining classic charm, and a beautiful 0.41 Acre setting, this move-in-ready home is ready for its next owners!! Schedule your showing today and discover all it has to offer!

312 Buffalo Trce, Winchester

$249,000

Welcome to 6 Hart Avenue in Winchester, Kentucky — a home that just feels right from the moment you pull up. This well-maintained tri-level offers 4 bedrooms, 1.5 baths, and a smart layout that gives everyone room to spread out while still feeling connected. The tri-level design creates natural separation of space — perfect for busy households, guests, or a dedicated home office. Rich hardwood floors bring warmth and timeless character, while the functional floor plan makes everyday living both comfortable and practical. Outside, you'll love the corner lot setting, fresh privacy fence, and the classic, low-maintenance brick and vinyl exterior. Situated on approximately .2 acres, this home offers just the right amount of yard without the overwhelming upkeep. And talk about convenience — you're just minutes from shopping in Winchester and quick access to I-64, making commuting a breeze. Well cared for, ideally located, and ready for its next chapter — this Hart Avenue home might just steal your heart!

4 Beds ⋅ 2 Baths ⋅ 26003316 MLS

Welcome to 6 Hart Avenue in Winchester, Kentucky — a home that just feels right from the moment you pull up. This well-maintained tri-level offers 4 bedrooms, 1.5 baths, and a smart layout that gives everyone room to spread out while still feeling connected. The tri-level design creates natural separation of space — perfect for busy households, guests, or a dedicated home office. Rich hardwood floors bring warmth and timeless character, while the functional floor plan makes everyday living both comfortable and practical. Outside, you'll love the corner lot setting, fresh privacy fence, and the classic, low-maintenance brick and vinyl exterior. Situated on approximately .2 acres, this home offers just the right amount of yard without the overwhelming upkeep. And talk about convenience — you're just minutes from shopping in Winchester and quick access to I-64, making commuting a breeze. Well cared for, ideally located, and ready for its next chapter — this Hart Avenue home might just steal your heart!

6 Hart Ave, Winchester

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