Keystokentucky.com Search Results

Welcome to this beautifully designed 3-bedroom, 2.5-bath ranch in the highly sought-after Earlymeade subdivision, where comfort, style, and exceptional efficiency come together. This spacious one-story home offers an open, inviting floor plan highlighted by a stunning floor-to-ceiling stone fireplace that anchors the expansive great room. The well-appointed kitchen features granite countertops, abundant workspace, and flows seamlessly into the living area—perfect for everyday living and entertaining. Throughout the home, you'll appreciate having no carpet, providing a clean, modern look that's both stylish and easy to maintain. What truly sets this home apart is its impressive investment in energy efficiency. Enjoy year-round comfort with a geothermal heating and cooling system, while solar panels paired with a Tesla battery backup help reduce energy costs and provide added peace of mind during power outages. Start your mornings on the covered front porch and relax in the evenings on the covered back porch, overlooking a beautiful greenspace with no rear neighbors directly behind you. Offering the perfect blend of quality construction, modern finishes, and cutting-edge energy-saving technology, this exceptional ranch is a rare opportunity in one of Winchesters most desirable neighborhoods.

4 Beds ⋅ 3 Baths ⋅ 26019672 MLS

Welcome to this beautifully designed 3-bedroom, 2.5-bath ranch in the highly sought-after Earlymeade subdivision, where comfort, style, and exceptional efficiency come together. This spacious one-story home offers an open, inviting floor plan highlighted by a stunning floor-to-ceiling stone fireplace that anchors the expansive great room. The well-appointed kitchen features granite countertops, abundant workspace, and flows seamlessly into the living area—perfect for everyday living and entertaining. Throughout the home, you'll appreciate having no carpet, providing a clean, modern look that's both stylish and easy to maintain. What truly sets this home apart is its impressive investment in energy efficiency. Enjoy year-round comfort with a geothermal heating and cooling system, while solar panels paired with a Tesla battery backup help reduce energy costs and provide added peace of mind during power outages. Start your mornings on the covered front porch and relax in the evenings on the covered back porch, overlooking a beautiful greenspace with no rear neighbors directly behind you. Offering the perfect blend of quality construction, modern finishes, and cutting-edge energy-saving technology, this exceptional ranch is a rare opportunity in one of Winchesters most desirable neighborhoods.

267 Runnymeade Dr, Winchester

$385,000

Welcome to this one-owner home offering the perfect combination of space, thoughtful updates, and country living! Built in 1996 and situated on 1.67 beautiful acres, this well-maintained 3-bedroom, 2-bath home features 1,344 square feet of comfortable living space with numerous improvements already completed for its next owner. Inside, you'll find updated interior paint, durable LifeProof laminate flooring, beautiful hardwood flooring, and replacement windows (house windows installed in 2021). Pride of ownership is evident throughout, and the home has never had indoor pets. One of the standout features is the impressive 896-square-foot attached garage. With insulated walls, an oversized 8-foot-tall by 18-foot-wide garage door, and a freshly painted interior (2026), this space offers endless possibilities. Whether you need room for oversized vehicles, a workshop, hobbies, or even future finished living space, this garage provides exceptional flexibility. Outside, enjoy the spacious 1.67-acre lot from the newer concrete front porch with handrails and thoughtful landscaping with plenty of shade trees or relax on the concrete back patio added in 2024. The detached 330-square-foot tool shed is equipped with water, electricity, and a 220-volt RV hookup, making it ideal for projects, storage, or RV owners. Major improvements include: • New HVAC system (2009) • Roof replaced (2015) • Vinyl siding and new concrete front porch with handrails (2016) • Garage door opener replaced (2018) • New garage door springs (2020) • Replacement house windows (2021; garage windows excluded) • Updated interior paint and LifeProof laminate flooring (2023) • HVAC professionally serviced (2023) • New concrete back patio (2024) • Garage interior repainted (2026) • Termite treatment maintained and updated • Updated most of the exterior hardware If you've been searching for a move-in-ready home with acreage, a massive insulated garage, an equipped workshop, and a long history of meticulous maintenance by its original owner, this property deserves a place at the top of your list. Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ 26020495 MLS

Welcome to this one-owner home offering the perfect combination of space, thoughtful updates, and country living! Built in 1996 and situated on 1.67 beautiful acres, this well-maintained 3-bedroom, 2-bath home features 1,344 square feet of comfortable living space with numerous improvements already completed for its next owner. Inside, you'll find updated interior paint, durable LifeProof laminate flooring, beautiful hardwood flooring, and replacement windows (house windows installed in 2021). Pride of ownership is evident throughout, and the home has never had indoor pets. One of the standout features is the impressive 896-square-foot attached garage. With insulated walls, an oversized 8-foot-tall by 18-foot-wide garage door, and a freshly painted interior (2026), this space offers endless possibilities. Whether you need room for oversized vehicles, a workshop, hobbies, or even future finished living space, this garage provides exceptional flexibility. Outside, enjoy the spacious 1.67-acre lot from the newer concrete front porch with handrails and thoughtful landscaping with plenty of shade trees or relax on the concrete back patio added in 2024. The detached 330-square-foot tool shed is equipped with water, electricity, and a 220-volt RV hookup, making it ideal for projects, storage, or RV owners. Major improvements include: • New HVAC system (2009) • Roof replaced (2015) • Vinyl siding and new concrete front porch with handrails (2016) • Garage door opener replaced (2018) • New garage door springs (2020) • Replacement house windows (2021; garage windows excluded) • Updated interior paint and LifeProof laminate flooring (2023) • HVAC professionally serviced (2023) • New concrete back patio (2024) • Garage interior repainted (2026) • Termite treatment maintained and updated • Updated most of the exterior hardware If you've been searching for a move-in-ready home with acreage, a massive insulated garage, an equipped workshop, and a long history of meticulous maintenance by its original owner, this property deserves a place at the top of your list. Schedule your private showing today!

2725 Goshen Rd, Winchester

$475,000

Back on the market at no fault of the sellers. Beautiful all brick ranch home on 4.1 acres that has 3 bedrooms, 2 bathrooms, open concept floor plan, large stone fireplace with wood burning stove & blower. Kitchen has butcher block countertops, garbage disposal, pot filler, range hood, ample cabinets with large pantry cabinet & island. Large primary suite that includes a walk-in tiled shower, with 2 shower heads, has a place for soaking tub with easy access for hooking up, 2 vanities, toilet closet and large closet with lots of built-in shelving. Easy access to laundry room which is right off of the garage and connects to primary suite. Family room has bar sink and overlooks a beautiful view of the secluded wooded backyard and has 3 French doors and 2 atrium doors to access back deck. Home has Pella windows and doors that are triple lock and Bryant Smart Home Wi-Fi thermostat & MyQ garage door opener app opens and closes garage door from anywhere. Large 2 car garage with mechanical room. Only 5 minutes from Mountain Parkway and 45 minutes to Toyota in Georgetown. Schedule your showing today!

3 Beds ⋅ 2 Baths ⋅ 26020298 MLS

Back on the market at no fault of the sellers. Beautiful all brick ranch home on 4.1 acres that has 3 bedrooms, 2 bathrooms, open concept floor plan, large stone fireplace with wood burning stove & blower. Kitchen has butcher block countertops, garbage disposal, pot filler, range hood, ample cabinets with large pantry cabinet & island. Large primary suite that includes a walk-in tiled shower, with 2 shower heads, has a place for soaking tub with easy access for hooking up, 2 vanities, toilet closet and large closet with lots of built-in shelving. Easy access to laundry room which is right off of the garage and connects to primary suite. Family room has bar sink and overlooks a beautiful view of the secluded wooded backyard and has 3 French doors and 2 atrium doors to access back deck. Home has Pella windows and doors that are triple lock and Bryant Smart Home Wi-Fi thermostat & MyQ garage door opener app opens and closes garage door from anywhere. Large 2 car garage with mechanical room. Only 5 minutes from Mountain Parkway and 45 minutes to Toyota in Georgetown. Schedule your showing today!

625 Pine Ridge Rd, Winchester

$349,000

This three bedroom home has been updated, new painting interior and exterior, new flooring, new light fixtures, new bath vanities, new granite in kitchen plus much more. Owner/Broker

3 Beds ⋅ 2 Baths ⋅ 26019263 MLS

This three bedroom home has been updated, new painting interior and exterior, new flooring, new light fixtures, new bath vanities, new granite in kitchen plus much more. Owner/Broker

11 Stoney Brook Dr Unit 1, Winchester

$379,000

Welcome to this superbly maintained home located in one of the area's most desirable neighborhoods. Offering 11 spacious rooms, this property delivers exceptional comfort, versatility, and charm. A beautiful front wrap around covered porch creates an inviting first impression, perfect for relaxing or greeting guests. The rear of the home features a covered back porch and an adjoining open deck, ideal for outdoor dining, entertaining, or enjoying peaceful evenings. An outbuilding provides valuable additional storage or workspace. Convenience is unmatched—you're just a few minutes from shopping, restaurants, golf courses, and the bypass, making daily living effortless while still enjoying the tranquility of a well established community. This home truly has so much to offer and is a must see for buyers seeking comfort, location, and lifestyle.

3 Beds ⋅ 3 Baths ⋅ 26019133 MLS

Welcome to this superbly maintained home located in one of the area's most desirable neighborhoods. Offering 11 spacious rooms, this property delivers exceptional comfort, versatility, and charm. A beautiful front wrap around covered porch creates an inviting first impression, perfect for relaxing or greeting guests. The rear of the home features a covered back porch and an adjoining open deck, ideal for outdoor dining, entertaining, or enjoying peaceful evenings. An outbuilding provides valuable additional storage or workspace. Convenience is unmatched—you're just a few minutes from shopping, restaurants, golf courses, and the bypass, making daily living effortless while still enjoying the tranquility of a well established community. This home truly has so much to offer and is a must see for buyers seeking comfort, location, and lifestyle.

322 Calmes Blvd, Winchester

$219,900

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

3 Beds ⋅ 2 Baths ⋅ 26018492 MLS

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

528 Estes Dr, Winchester

$524,900

OK! WOW!!! Location is yes, yes, yes! This house is located in a quiet residential neighborhood and in minutes you can be at the I-64 or I-75 interstate corridors. OK enough about location. This house is pristine! The owners have improved the property with new dimensional style roof shingles in 2025 along with new gutters. They have freshly painted the interior. They have added a new refrigerator, stove, microwave and a washer and dryer. The owners have meticulously maintained this house throughout. From the entrance foyer note the gleaming wood flooring and the fresh paint on the 9' foot ceiling walls, the vaulted great room and the crown molding. The split bedroom concept is great for guests or a home office. And above the garage is a bonus room measuring 420 sq ft. Entertaining or relaxing on the covered back patio that overlooks the beautiful Kentucky Bluegrass is a must. And bonus, the property is adjacent to a church property that is mowed for a walking path. Make an appointment to see this house today, it may be your new home.

3 Beds ⋅ 3 Baths ⋅ 26018460 MLS

OK! WOW!!! Location is yes, yes, yes! This house is located in a quiet residential neighborhood and in minutes you can be at the I-64 or I-75 interstate corridors. OK enough about location. This house is pristine! The owners have improved the property with new dimensional style roof shingles in 2025 along with new gutters. They have freshly painted the interior. They have added a new refrigerator, stove, microwave and a washer and dryer. The owners have meticulously maintained this house throughout. From the entrance foyer note the gleaming wood flooring and the fresh paint on the 9' foot ceiling walls, the vaulted great room and the crown molding. The split bedroom concept is great for guests or a home office. And above the garage is a bonus room measuring 420 sq ft. Entertaining or relaxing on the covered back patio that overlooks the beautiful Kentucky Bluegrass is a must. And bonus, the property is adjacent to a church property that is mowed for a walking path. Make an appointment to see this house today, it may be your new home.

275 Runnymeade Dr, Winchester

$749,900

Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides privacy, while the primary suite offers a spa-like bath and walk-in closet. Enjoy scenic views from the covered porch and the convenience of an attached two-car garage, all while being just a short drive to Winchester, Paris, and Lexington. This is the perfect blend of modern comfort and peaceful country living. Schedule your showing today!

3 Beds ⋅ 3 Baths ⋅ 26017698 MLS

Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides privacy, while the primary suite offers a spa-like bath and walk-in closet. Enjoy scenic views from the covered porch and the convenience of an attached two-car garage, all while being just a short drive to Winchester, Paris, and Lexington. This is the perfect blend of modern comfort and peaceful country living. Schedule your showing today!

2180 Big Stoner Rd, Winchester

122 Callaway Street Se Callaway Street, Winchester

$124,500

Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless possibilities! Property is AS IS! Bring me a offer.

2 Beds ⋅ 1 Baths ⋅ 26000228 MLS

Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless possibilities! Property is AS IS! Bring me a offer.

122 Callaway Street Se Callaway Street, Winchester

$160,000

Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.

4 Beds ⋅ 3 Baths ⋅ 26008701 MLS

Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.

229 S Highland St, Winchester

$1,595,000

NEW PRICE!!! Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points in Clark County, where you can see the panoramic views stretching all the way to the dormitories at EKU in Richmond and the mountains near Berea, KY. Relax by the newly lined in-ground pool with a new cover, and unwind in the hot tub while taking in the beautiful sunrise and sunset views — perfect for family gatherings or quiet evenings under the stars. The property features a two-level barn with horse stalls, a tack room, and a spacious open arena — ideal for equestrian enthusiasts. The upper level of the barn provides versatile space for auto storage or a workshop, while the fenced pastures and horse ring make it ready for boarding or training horses. This property also includes a stocked pond, adding to the tranquil landscape, and 2 gated driveways with a security system for peace of mind. The land features mature trees, including fig, pear, and apple. This is the first property on Colby Road out of Winchester with agricultural zoning, a very private estate, and the first time in 40 years this remarkable property has been for sale. Conveniently located just one mile to Kroger, Lowe's, and Walmart, and approximately 20 min. from Man O War via Todds Rd. Lexington. This property offers both peaceful seclusion and easy access to amenities. With potential for income from horse boarding and a rental home on the property, this exceptional farm is more than a home- it's a lifestyle, an investment, and a place to create lasting memories for generations to come.

3 Beds ⋅ 3 Baths ⋅ 26011538 MLS

NEW PRICE!!! Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points in Clark County, where you can see the panoramic views stretching all the way to the dormitories at EKU in Richmond and the mountains near Berea, KY. Relax by the newly lined in-ground pool with a new cover, and unwind in the hot tub while taking in the beautiful sunrise and sunset views — perfect for family gatherings or quiet evenings under the stars. The property features a two-level barn with horse stalls, a tack room, and a spacious open arena — ideal for equestrian enthusiasts. The upper level of the barn provides versatile space for auto storage or a workshop, while the fenced pastures and horse ring make it ready for boarding or training horses. This property also includes a stocked pond, adding to the tranquil landscape, and 2 gated driveways with a security system for peace of mind. The land features mature trees, including fig, pear, and apple. This is the first property on Colby Road out of Winchester with agricultural zoning, a very private estate, and the first time in 40 years this remarkable property has been for sale. Conveniently located just one mile to Kroger, Lowe's, and Walmart, and approximately 20 min. from Man O War via Todds Rd. Lexington. This property offers both peaceful seclusion and easy access to amenities. With potential for income from horse boarding and a rental home on the property, this exceptional farm is more than a home- it's a lifestyle, an investment, and a place to create lasting memories for generations to come.

3166 Colby Rd, Winchester

$209,000

Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a beautifully updated kitchen featuring stainless steel appliances, a gas range, pantry, and plenty of space for cooking and entertaining. The home offers a primary suite, two additional bedrooms, an additional full bath, and a large utility room with extra storage and functionality. Outside, the 20x24 detached garage with electric is a rare bonus and ideal for carpentry projects, woodworking, hobbies, a workshop, home gym, storage for recreational equipment, or even the perfect space for car enthusiasts and DIYers. Enjoy small-town charm with quick access to shopping, dining, and interstate travel in this thoughtfully updated property ready for its next owner!

3 Beds ⋅ 2 Baths ⋅ 26011961 MLS

Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a beautifully updated kitchen featuring stainless steel appliances, a gas range, pantry, and plenty of space for cooking and entertaining. The home offers a primary suite, two additional bedrooms, an additional full bath, and a large utility room with extra storage and functionality. Outside, the 20x24 detached garage with electric is a rare bonus and ideal for carpentry projects, woodworking, hobbies, a workshop, home gym, storage for recreational equipment, or even the perfect space for car enthusiasts and DIYers. Enjoy small-town charm with quick access to shopping, dining, and interstate travel in this thoughtfully updated property ready for its next owner!

14 Cook Ave, Winchester

$349,000

Just a 20-second golf cart ride to the Winchester Country Club driving range! Built in 2024 and upgraded throughout, this beautiful 3-bedroom, 2.5-bath home offers modern style, functional living space, and a prime location. The open-concept main level features a spacious living room, kitchen, and dining area designed for both everyday living and entertaining, complete with granite countertops in the kitchen and baths, a deep farmhouse sink, pantry, and stainless appliances. Upstairs, you'll find a generous primary suite with a private bath and walk-in closet, along with two additional bedrooms and a full guest bath. Luxury vinyl plank flooring runs throughout the home, while accent wallpaper in multiple rooms adds warmth, personality, and a custom feel. Recent owner upgrades include a privacy fence, landscape lighting and new shrubs, upgraded stair treads, a concrete sidewalk, and additional attic flooring with a folding attic ladder for convenient storage. The home's attractive exterior combines clean modern lines with shake-style architectural accents, creating great curb appeal. Enjoy nearby golf course views and the convenience of country club living without being directly on the course. Additional features include a 2-car attached garage, crawlspace foundation, and no HOA. With modern construction, quality finishes, and numerous owner-added improvements, this move-in ready home is ready for its next owners to enjoy.

3 Beds ⋅ 3 Baths ⋅ 26013780 MLS

Just a 20-second golf cart ride to the Winchester Country Club driving range! Built in 2024 and upgraded throughout, this beautiful 3-bedroom, 2.5-bath home offers modern style, functional living space, and a prime location. The open-concept main level features a spacious living room, kitchen, and dining area designed for both everyday living and entertaining, complete with granite countertops in the kitchen and baths, a deep farmhouse sink, pantry, and stainless appliances. Upstairs, you'll find a generous primary suite with a private bath and walk-in closet, along with two additional bedrooms and a full guest bath. Luxury vinyl plank flooring runs throughout the home, while accent wallpaper in multiple rooms adds warmth, personality, and a custom feel. Recent owner upgrades include a privacy fence, landscape lighting and new shrubs, upgraded stair treads, a concrete sidewalk, and additional attic flooring with a folding attic ladder for convenient storage. The home's attractive exterior combines clean modern lines with shake-style architectural accents, creating great curb appeal. Enjoy nearby golf course views and the convenience of country club living without being directly on the course. Additional features include a 2-car attached garage, crawlspace foundation, and no HOA. With modern construction, quality finishes, and numerous owner-added improvements, this move-in ready home is ready for its next owners to enjoy.

309 Gallahadion Ct, Winchester

$130,000

Affordable and move in ready! This home will qualify for FHA, VA &/or Rural Housing Loan. This charming 3 bedroom, 1 bath home offers the perfect opportunity for first-time buyers, down-sizers, or investors. With a welcoming layout, comfortable living spaces, and a great location in Winchester, this property is an excellent value in today's market. Enjoy the convenience of nearby shopping, dining, and easy access to I-64 while still tucked away on a quiet street. Homes at this price point are hard to find...don't miss your chance to make this one yours!

3 Beds ⋅ 1 Baths ⋅ 25500573 MLS

Affordable and move in ready! This home will qualify for FHA, VA &/or Rural Housing Loan. This charming 3 bedroom, 1 bath home offers the perfect opportunity for first-time buyers, down-sizers, or investors. With a welcoming layout, comfortable living spaces, and a great location in Winchester, this property is an excellent value in today's market. Enjoy the convenience of nearby shopping, dining, and easy access to I-64 while still tucked away on a quiet street. Homes at this price point are hard to find...don't miss your chance to make this one yours!

103 Yorktowne Ct, Winchester

$435,000

This 3 bedroom 2 bath ranch home is tucked away in a beautiful wooded area of Clark County. It is sitting on over 10 acres of land that would be great for livestock or hunting. It is just minutes from historic downtown Winchester. The property is also a short drive to retail shops, restaurants, and other amenities. Come take a look at the beautiful view from the front porch of this home in the country.

3 Beds ⋅ 2 Baths ⋅ 26011126 MLS

This 3 bedroom 2 bath ranch home is tucked away in a beautiful wooded area of Clark County. It is sitting on over 10 acres of land that would be great for livestock or hunting. It is just minutes from historic downtown Winchester. The property is also a short drive to retail shops, restaurants, and other amenities. Come take a look at the beautiful view from the front porch of this home in the country.

287 Logan Lick Rd, Winchester

$229,000

Welcome to a well maintained 3 bedroom 1 full bath home that has been lovingly cared for by only two owners since 1962. Recent updates include new flooring and completed repairs, makiing this property ready for a new owner, while preserving its timeless character. Beautiful hardwood floors add warmth and charm throughout the home. Enjoy relaxing or entertaining on the comfortable spacious patio perfectly sized for gatherings. The brick fireplace with gas logs, located in the living room, adds a cozy ambience on cool evenings. One of the property's standout features is its prime location backing directly to Legacy Grove Park complete with a private gate providing conveninent park access. This unique setting offers addttiional outdoor space, scenic views and a peaceful atmosphere right in your own backyard. . This is a wonderful opportunity to call a well cared for property with an abundance of charm your very own.

3 Beds ⋅ 1 Baths ⋅ 26013434 MLS

Welcome to a well maintained 3 bedroom 1 full bath home that has been lovingly cared for by only two owners since 1962. Recent updates include new flooring and completed repairs, makiing this property ready for a new owner, while preserving its timeless character. Beautiful hardwood floors add warmth and charm throughout the home. Enjoy relaxing or entertaining on the comfortable spacious patio perfectly sized for gatherings. The brick fireplace with gas logs, located in the living room, adds a cozy ambience on cool evenings. One of the property's standout features is its prime location backing directly to Legacy Grove Park complete with a private gate providing conveninent park access. This unique setting offers addttiional outdoor space, scenic views and a peaceful atmosphere right in your own backyard. . This is a wonderful opportunity to call a well cared for property with an abundance of charm your very own.

30 Virginia Ave, Winchester

$99,500

Affordable housing! Check out this newly remodeled and updated home! 2 bedroom, 2 full bath! All new flooring, cabinets, vanities, and so much more! No lot rent here! You will own the lot as well, making this a great option for starter, downsizing, investment property (previously rented for $925), or just an affordable home. Nice covered porch, 2 storage sheds, brand new metal roof! $150 per month HOA fee covers your water, sewer, trash, and common area maintenance. Property is under a contingent contract with kick out clause.

2 Beds ⋅ 2 Baths ⋅ 26012893 MLS

Affordable housing! Check out this newly remodeled and updated home! 2 bedroom, 2 full bath! All new flooring, cabinets, vanities, and so much more! No lot rent here! You will own the lot as well, making this a great option for starter, downsizing, investment property (previously rented for $925), or just an affordable home. Nice covered porch, 2 storage sheds, brand new metal roof! $150 per month HOA fee covers your water, sewer, trash, and common area maintenance. Property is under a contingent contract with kick out clause.

563 Constitution Dr, Winchester

$204,900

Ranch with covered porch, new roof, new appliances and countertops, new bath vanity, new professional paint job. Vaulted ceiling in the living room. Clean and ready for occupancy.

3 Beds ⋅ 2 Baths ⋅ 26004000 MLS

Ranch with covered porch, new roof, new appliances and countertops, new bath vanity, new professional paint job. Vaulted ceiling in the living room. Clean and ready for occupancy.

500 Hidden Hills Way, Winchester

$369,900

Welcome to 107 Hibiscus, where thoughtful updates, quality craftsmanship, and exceptional maintenance come together in this spacious 4-bedroom, 2.5-bath home. Offering a versatile floor plan with generous living spaces, this move-in-ready property has benefited from approximately nearly $70,000 in improvements over the past several years, providing peace of mind and modern finishes throughout. Major mechanical updates include replacement heat pumps (downstairs in 2020 and upstairs in August 2024), all new energy-efficient windows installed in 2025 with a transferable 10-year warranty, a new three-panel sliding back door, recently cleaned ductwork, spray-foam insulated crawl space, additional attic insulation, a roof replaced approximately 8-10 years ago, and garage doors replaced approximately two years ago. Inside, you'll appreciate the beautiful ¾-inch solid oak hardwood flooring throughout the main level, fresh interior paint, updated light fixtures, ceiling fans, new door hardware, elegant crown molding, a cozy gas log fireplace, and renovated bathrooms featuring updated tile, mirrors, lighting, faucets, and refreshed cabinetry. The beautifully updated kitchen is designed for both everyday living and entertaining, offering new granite countertops, freshly painted cabinetry, all-new stainless steel appliances including a gas range, dishwasher, microwave, and refrigerator, plus a convenient coffee bar that adds both style and functionality. Outdoor living is just as impressive with a large deck, a freshly painted front porch, and a high-quality custom-built storage shed constructed with 12-inch studs for exceptional durability. If you're searching for a meticulously maintained home where many of the major updates have already been completed, 107 Hibiscus deserves a place at the top of your list. Buyer to verify all aspects of the property, including but not limited to square footage, schools, boundaries, and any information deemed important to the purchase. Schedule your showing today!

4 Beds ⋅ 3 Baths ⋅ 26015608 MLS

Welcome to 107 Hibiscus, where thoughtful updates, quality craftsmanship, and exceptional maintenance come together in this spacious 4-bedroom, 2.5-bath home. Offering a versatile floor plan with generous living spaces, this move-in-ready property has benefited from approximately nearly $70,000 in improvements over the past several years, providing peace of mind and modern finishes throughout. Major mechanical updates include replacement heat pumps (downstairs in 2020 and upstairs in August 2024), all new energy-efficient windows installed in 2025 with a transferable 10-year warranty, a new three-panel sliding back door, recently cleaned ductwork, spray-foam insulated crawl space, additional attic insulation, a roof replaced approximately 8-10 years ago, and garage doors replaced approximately two years ago. Inside, you'll appreciate the beautiful ¾-inch solid oak hardwood flooring throughout the main level, fresh interior paint, updated light fixtures, ceiling fans, new door hardware, elegant crown molding, a cozy gas log fireplace, and renovated bathrooms featuring updated tile, mirrors, lighting, faucets, and refreshed cabinetry. The beautifully updated kitchen is designed for both everyday living and entertaining, offering new granite countertops, freshly painted cabinetry, all-new stainless steel appliances including a gas range, dishwasher, microwave, and refrigerator, plus a convenient coffee bar that adds both style and functionality. Outdoor living is just as impressive with a large deck, a freshly painted front porch, and a high-quality custom-built storage shed constructed with 12-inch studs for exceptional durability. If you're searching for a meticulously maintained home where many of the major updates have already been completed, 107 Hibiscus deserves a place at the top of your list. Buyer to verify all aspects of the property, including but not limited to square footage, schools, boundaries, and any information deemed important to the purchase. Schedule your showing today!

107 Hibiscus Ln, Winchester

$155,900

Step back in time and discover the possibilities in this classic 1930-built home full of character and opportunity! With solid bones and vintage details, this property is the perfect canvas for investors, renovators, or anyone dreaming of restoring a piece of history. Featuring spacious rooms, original architectrual touches, and a layout just waiting to be reimagined. This home offers incredible potential to create something truly special. While its in good condition it is ready for some TLC, the price reflects the opportunity to build equity and customize to your taste. Whether you're looking to flip, rent, or make this your forever home, this property is packed with promise. Bring your vision and make it shine again! Opportunities like this don't come around often, so schedule your showing today!!!

1 Beds ⋅ 2 Baths ⋅ 26007407 MLS

Step back in time and discover the possibilities in this classic 1930-built home full of character and opportunity! With solid bones and vintage details, this property is the perfect canvas for investors, renovators, or anyone dreaming of restoring a piece of history. Featuring spacious rooms, original architectrual touches, and a layout just waiting to be reimagined. This home offers incredible potential to create something truly special. While its in good condition it is ready for some TLC, the price reflects the opportunity to build equity and customize to your taste. Whether you're looking to flip, rent, or make this your forever home, this property is packed with promise. Bring your vision and make it shine again! Opportunities like this don't come around often, so schedule your showing today!!!

101 Alabama St, Winchester

$255,000

Space, updates, and charm all come together in this spacious 2,260 square foot 1.5-story home located in the heart of Winchester! Recently updated and full of character, this property offers a flexible layout with room for everyone. The main level offers a welcoming living room, large family room, dining area, kitchen, laundry room, full guest bath, and a spacious primary suite complete with a private bath. Upstairs you'll find two additional generously sized bedrooms along with a convenient half bath. Enjoy relaxing mornings on the covered front porch made for rocking chairs or unwind on the covered rear porch overlooking the backyard. Additional features include two carports, storage building, rear drive access, fresh paint, some new flooring, central heat and air, and much more! Don't miss your opportunity to own this move-in ready home with space, updates, and charm throughout. Schedule your showing today! This is a Fannie Mae HomePath property.

3 Beds ⋅ 3 Baths ⋅ 26011097 MLS

Space, updates, and charm all come together in this spacious 2,260 square foot 1.5-story home located in the heart of Winchester! Recently updated and full of character, this property offers a flexible layout with room for everyone. The main level offers a welcoming living room, large family room, dining area, kitchen, laundry room, full guest bath, and a spacious primary suite complete with a private bath. Upstairs you'll find two additional generously sized bedrooms along with a convenient half bath. Enjoy relaxing mornings on the covered front porch made for rocking chairs or unwind on the covered rear porch overlooking the backyard. Additional features include two carports, storage building, rear drive access, fresh paint, some new flooring, central heat and air, and much more! Don't miss your opportunity to own this move-in ready home with space, updates, and charm throughout. Schedule your showing today! This is a Fannie Mae HomePath property.

209 Boone Ave, Winchester

$269,900

You Wont Find A More Beautiful And Private Setting!!! This Home Features 3 Bedrooms And 1 Bath And Sits On 5.05 Acres; Two Front Porches; Large Rear Porch; A Separate Room Downstairs That Would Make A Great Master Bedroom/Suite Potentially; Huge Mudroom/Flex Space! Possibilities Are Endless With This Property. This Home Has Replacement Vinyl Clad Windows, Roof And HVAC All Replaced In Last 10 Years Approximately, But Needs Whole House Remodel. Could Use Floor Plan Rework As Well To Make It Flow. Great Opportunity!!

3 Beds ⋅ 1 Baths ⋅ 26010776 MLS

You Wont Find A More Beautiful And Private Setting!!! This Home Features 3 Bedrooms And 1 Bath And Sits On 5.05 Acres; Two Front Porches; Large Rear Porch; A Separate Room Downstairs That Would Make A Great Master Bedroom/Suite Potentially; Huge Mudroom/Flex Space! Possibilities Are Endless With This Property. This Home Has Replacement Vinyl Clad Windows, Roof And HVAC All Replaced In Last 10 Years Approximately, But Needs Whole House Remodel. Could Use Floor Plan Rework As Well To Make It Flow. Great Opportunity!!

205 Providence Ln, Winchester

$139,900

Lovely older home, located witin waking distance to collage park whice offers Pickle Ball, Pool, Tennis, play gound and Walking Trail, also walking distance to Historic Downtown Winchester, with a little love house brings large rooms and a nostlogic atmosphire, take a look, view today, this a a great price for 3 bedrooms, 1 1/2 baths, nice back yard, with parking, call today! Selling "AS IS", inspections welcome, the are no utilties on at the present, Estate Please make sure all doors are locked when you leave, buyer to verifye size of home & Lot

3 Beds ⋅ 2 Baths ⋅ 26013935 MLS

Lovely older home, located witin waking distance to collage park whice offers Pickle Ball, Pool, Tennis, play gound and Walking Trail, also walking distance to Historic Downtown Winchester, with a little love house brings large rooms and a nostlogic atmosphire, take a look, view today, this a a great price for 3 bedrooms, 1 1/2 baths, nice back yard, with parking, call today! Selling "AS IS", inspections welcome, the are no utilties on at the present, Estate Please make sure all doors are locked when you leave, buyer to verifye size of home & Lot

65 Fitch Ave, Winchester

$155,000

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

2 Beds ⋅ 1 Baths ⋅ 26008307 MLS

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

13 Maryland Ave, Winchester

$415,000

Welcome to 187 Hawthorne Drive, a beautifully maintained brick home in one of Winchester's most sought-after neighborhoods. Offering convenient one-level living, this 3-bedroom, 2-bath home features an inviting open floor plan that's perfect for everyday living and entertaining. The spacious living room is anchored by a cozy natural gas fireplace with gas logs, creating a warm and welcoming gathering space. The eat-in kitchen features a breakfast bar and includes a brand-new refrigerator and a quiet new garbage disposal. Recent updates throughout the home provide both style and peace of mind. Gorgeous hardwood flooring has been added to all three bedrooms, and tile flooring has been installed to replace the previous vinyl in the laundry room, pantry, and hallway. The private primary suite is thoughtfully situated on its own side of the home and features an updated shower insert. Enjoy relaxing mornings with coffee or peaceful summer evenings on the screened-in back porch, where you can take advantage of the outdoors without the bugs. Plenty of storage is available with an extra garage closet, pull-down attic storage, and an extra-high crawl space that's ideal for storing lawn equipment, seasonal items, or outdoor tools. The sellers have also invested in ensuring the crawl space remains dry and well protected. Additional upgrades include an HVAC system, updated closet shelving throughout the home, and natural gas service installation. If you're searching for a move-in ready home in Winchester, KY with one-level living, modern updates, excellent storage, and a desirable location close to shopping, dining, schools, and everyday conveniences, 187 Hawthorne Drive is one you won't want to miss.

3 Beds ⋅ 2 Baths ⋅ 26015824 MLS

Welcome to 187 Hawthorne Drive, a beautifully maintained brick home in one of Winchester's most sought-after neighborhoods. Offering convenient one-level living, this 3-bedroom, 2-bath home features an inviting open floor plan that's perfect for everyday living and entertaining. The spacious living room is anchored by a cozy natural gas fireplace with gas logs, creating a warm and welcoming gathering space. The eat-in kitchen features a breakfast bar and includes a brand-new refrigerator and a quiet new garbage disposal. Recent updates throughout the home provide both style and peace of mind. Gorgeous hardwood flooring has been added to all three bedrooms, and tile flooring has been installed to replace the previous vinyl in the laundry room, pantry, and hallway. The private primary suite is thoughtfully situated on its own side of the home and features an updated shower insert. Enjoy relaxing mornings with coffee or peaceful summer evenings on the screened-in back porch, where you can take advantage of the outdoors without the bugs. Plenty of storage is available with an extra garage closet, pull-down attic storage, and an extra-high crawl space that's ideal for storing lawn equipment, seasonal items, or outdoor tools. The sellers have also invested in ensuring the crawl space remains dry and well protected. Additional upgrades include an HVAC system, updated closet shelving throughout the home, and natural gas service installation. If you're searching for a move-in ready home in Winchester, KY with one-level living, modern updates, excellent storage, and a desirable location close to shopping, dining, schools, and everyday conveniences, 187 Hawthorne Drive is one you won't want to miss.

187 Hawthorne Dr, Winchester

How much is your home worth?

How much is your home worth?