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Some houses have a little more personality than others. 108 First Street is one of them. Start your morning on the front porch with a cup of coffee and the sounds of Simpsonville waking up around you. Church bells across the street, a short walk to the farmers market, and Simpsonville Park just down the road give this home a location that is hard to duplicate. Inside, the character continues. This well-maintained older home has the details you hope to find, including beautiful original trim, solid-core doors, and a story-and-a-half layout that gives the home plenty of personality without sacrificing function. The kitchen has been renovated, the laundry is conveniently located on the main floor, and there are three bedrooms and two full bathrooms spread across approximately 1,788 square feet. The roughly .3-acre lot gives you just enough room to enjoy the outdoors without spending your weekends maintaining a huge yard. Garden, entertain, let the kids play, or simply sit on the porch and watch the neighborhood go by. And then there's the location. You're right in the heart of old-town Simpsonville, close enough to walk to some of the town's favorite spots while still being only minutes from I-64. If you like homes with character, a little history, and a location that lets you actually enjoy small-town living, 108 First Street deserves a look.

3 Beds ⋅ 2 Baths ⋅ 1729967 MLS

Some houses have a little more personality than others. 108 First Street is one of them. Start your morning on the front porch with a cup of coffee and the sounds of Simpsonville waking up around you. Church bells across the street, a short walk to the farmers market, and Simpsonville Park just down the road give this home a location that is hard to duplicate. Inside, the character continues. This well-maintained older home has the details you hope to find, including beautiful original trim, solid-core doors, and a story-and-a-half layout that gives the home plenty of personality without sacrificing function. The kitchen has been renovated, the laundry is conveniently located on the main floor, and there are three bedrooms and two full bathrooms spread across approximately 1,788 square feet. The roughly .3-acre lot gives you just enough room to enjoy the outdoors without spending your weekends maintaining a huge yard. Garden, entertain, let the kids play, or simply sit on the porch and watch the neighborhood go by. And then there's the location. You're right in the heart of old-town Simpsonville, close enough to walk to some of the town's favorite spots while still being only minutes from I-64. If you like homes with character, a little history, and a location that lets you actually enjoy small-town living, 108 First Street deserves a look.

108 1st St, Simpsonville

Listing courtesy of Torrey Smith Realty Co., LLC.

$399,500

Brand New Roof!! Looking for more room to spread out without giving up the spaces that bring everyone together? This 4-bedroom, 2.5-bath home in Todd's Station in Simpsonville offers a flexible layout, multiple living and entertaining spaces, a 2-car garage, and convenient access to I-64. A covered front porch welcomes you inside, where beautiful flooring carries through the main level. Just off the entry, the spacious dining room gives you room for holiday dinners, celebrations, or simply gathering around the table. At the heart of the home, the open great room brings the living room, kitchen, and dining area together, creating an easy flow for everyday life and entertaining. Just beyond, a vaulted sunroom adds the kind of flexible space that can change right along with you, whether it be a home office, playroom, game room, reading space, or additional place to relax. From the sunroom, step directly onto the large back deck, extending your living space outdoors with plenty of room for grilling, dining, entertaining, or unwinding at the end of the day. A half bath and laundry room conveniently located near the kitchen and 2-car garage complete your main level. Upstairs, the primary suite gives you a place to recharge with a spacious walk-in closet and ensuite bath featuring double sinks, a jetted tub, and separate shower. Three additional bedrooms and another full bath provide even more options for bedrooms, guests, hobbies, or work-from-home space. Located in Simpsonville's Todd's Station neighborhood, you're just minutes from I-64 and the Outlet Shoppes of the Bluegrass, making it easy to reach shopping, dining, and destinations throughout Shelby County and the Louisville area. If your next home needs to give you more space, more flexibility, and more ways to enjoy it, this one is ready to fit the way you live.

4 Beds ⋅ 3 Baths ⋅ 1728891 MLS

Brand New Roof!! Looking for more room to spread out without giving up the spaces that bring everyone together? This 4-bedroom, 2.5-bath home in Todd's Station in Simpsonville offers a flexible layout, multiple living and entertaining spaces, a 2-car garage, and convenient access to I-64. A covered front porch welcomes you inside, where beautiful flooring carries through the main level. Just off the entry, the spacious dining room gives you room for holiday dinners, celebrations, or simply gathering around the table. At the heart of the home, the open great room brings the living room, kitchen, and dining area together, creating an easy flow for everyday life and entertaining. Just beyond, a vaulted sunroom adds the kind of flexible space that can change right along with you, whether it be a home office, playroom, game room, reading space, or additional place to relax. From the sunroom, step directly onto the large back deck, extending your living space outdoors with plenty of room for grilling, dining, entertaining, or unwinding at the end of the day. A half bath and laundry room conveniently located near the kitchen and 2-car garage complete your main level. Upstairs, the primary suite gives you a place to recharge with a spacious walk-in closet and ensuite bath featuring double sinks, a jetted tub, and separate shower. Three additional bedrooms and another full bath provide even more options for bedrooms, guests, hobbies, or work-from-home space. Located in Simpsonville's Todd's Station neighborhood, you're just minutes from I-64 and the Outlet Shoppes of the Bluegrass, making it easy to reach shopping, dining, and destinations throughout Shelby County and the Louisville area. If your next home needs to give you more space, more flexibility, and more ways to enjoy it, this one is ready to fit the way you live.

140 Lincoln Station Dr, Simpsonville

Listing courtesy of Keller Williams Collective.

$220,000

Welcome home to this beautifully maintained patio home in the sought-after Gardens of Station Pointe community. Featuring a spacious family room with a cozy fireplace, a separate private living room, and you own private patio retreat. This home offers a lifestyle that's both comfortable and refined. Abundant storage throughout means this home lives much larger than its footprint. Low maintenance living is the theme - enjoy life while the HOA handles the exterior upkeep. Community amenities include a beautiful clubhouse for entertaining and a fully equipped exercise room, all just steps from your door. Located in charming Simpsonville - the heart of Kentucky's celebrated bluegrass horse country and just minutes the Outlets of the Bluegrass, where name-brand shopping and entertainment await!

2 Beds ⋅ 2 Baths ⋅ 1728532 MLS

Welcome home to this beautifully maintained patio home in the sought-after Gardens of Station Pointe community. Featuring a spacious family room with a cozy fireplace, a separate private living room, and you own private patio retreat. This home offers a lifestyle that's both comfortable and refined. Abundant storage throughout means this home lives much larger than its footprint. Low maintenance living is the theme - enjoy life while the HOA handles the exterior upkeep. Community amenities include a beautiful clubhouse for entertaining and a fully equipped exercise room, all just steps from your door. Located in charming Simpsonville - the heart of Kentucky's celebrated bluegrass horse country and just minutes the Outlets of the Bluegrass, where name-brand shopping and entertainment await!

828 Garden Pointe Dr, Simpsonville

Listing courtesy of Abbot Realty & Auction.

$329,900

Welcome to 220 Rolling Ridge Way, a Charming 2 Story Colonial-style home situated on a corner lot with a white picket fence surrounding the Backyard. This Beautiful home features 3 Bedrooms, 2 full bathrooms upstairs, and 1 half bath on the first floor; an amazing fenced-in backyard with a large, freshly stained deck; a 1 Car Attached garage; and a double-wide driveway. As you step inside, you will find New LVP Flooring installed throughout the entire first floor in August 2026, freshly painted walls & trim on the first floor, built-in bookshelves, and an entertainment center. There is a Formal Dining Room just off the Living Room, with a lovely Bay Window that flows into the Kitchen, which features a New Refrigerator, New Microwave, 2 New Ceiling Lights, and a Newer Backsplash. The Laundry Room is also located just off the Kitchen. Upstairs, you will find 3 Bedrooms that all have New Carpet installed in August 2026, New LVP flooring in the Hallway and Primary Bathroom, a New Ceiling Fan in the front bedroom, freshly painted trim throughout the upstairs, freshly painted hallway, a freshly painted vanity in the Primary Bathroom, a new light in the Primary Bathroom, and a New Light in the Full Hall Bathroom. Out back is your own outdoor Oasis with a Large Backyard, freshly stained deck, freshly painted white picket fence, mature trees, and an attached storage shed. There is plenty of space out back for a garden, a pool, and space for the kids and dogs to run around. This wonderful home is located only 1.5 miles from the Outlet Mall, only 1 mile from I-64, and 10 miles from the Gene Snyder. Also, Beckley Creek Park is only 10 miles away and features picnic areas, fishing lakes, farmers' markets, community gardens, and paved and natural-surface trails that wind along the creek. Come see this wonderful home today!

3 Beds ⋅ 3 Baths ⋅ 1727753 MLS

Welcome to 220 Rolling Ridge Way, a Charming 2 Story Colonial-style home situated on a corner lot with a white picket fence surrounding the Backyard. This Beautiful home features 3 Bedrooms, 2 full bathrooms upstairs, and 1 half bath on the first floor; an amazing fenced-in backyard with a large, freshly stained deck; a 1 Car Attached garage; and a double-wide driveway. As you step inside, you will find New LVP Flooring installed throughout the entire first floor in August 2026, freshly painted walls & trim on the first floor, built-in bookshelves, and an entertainment center. There is a Formal Dining Room just off the Living Room, with a lovely Bay Window that flows into the Kitchen, which features a New Refrigerator, New Microwave, 2 New Ceiling Lights, and a Newer Backsplash. The Laundry Room is also located just off the Kitchen. Upstairs, you will find 3 Bedrooms that all have New Carpet installed in August 2026, New LVP flooring in the Hallway and Primary Bathroom, a New Ceiling Fan in the front bedroom, freshly painted trim throughout the upstairs, freshly painted hallway, a freshly painted vanity in the Primary Bathroom, a new light in the Primary Bathroom, and a New Light in the Full Hall Bathroom. Out back is your own outdoor Oasis with a Large Backyard, freshly stained deck, freshly painted white picket fence, mature trees, and an attached storage shed. There is plenty of space out back for a garden, a pool, and space for the kids and dogs to run around. This wonderful home is located only 1.5 miles from the Outlet Mall, only 1 mile from I-64, and 10 miles from the Gene Snyder. Also, Beckley Creek Park is only 10 miles away and features picnic areas, fishing lakes, farmers' markets, community gardens, and paved and natural-surface trails that wind along the creek. Come see this wonderful home today!

220 Rolling Ridge Way, Simpsonville

Listing courtesy of United Real Estate Louisville.

$245,000

Welcome home to this beautifully updated 3-bedroom, 2-bath property situated on just over half an acre in Simpsonville, Kentucky. The refreshed kitchen and interior create a warm, move-in-ready atmosphere, while major recent improvements include a brand-new roof, brand-new water heater, and an oversized new deck that's perfect for entertaining, grilling, or relaxing outdoors. With generous yard space and plenty of parking, this home offers comfort, convenience, and room to enjoy both inside and out.

3 Beds ⋅ 2 Baths ⋅ 1725643 MLS

Welcome home to this beautifully updated 3-bedroom, 2-bath property situated on just over half an acre in Simpsonville, Kentucky. The refreshed kitchen and interior create a warm, move-in-ready atmosphere, while major recent improvements include a brand-new roof, brand-new water heater, and an oversized new deck that's perfect for entertaining, grilling, or relaxing outdoors. With generous yard space and plenty of parking, this home offers comfort, convenience, and room to enjoy both inside and out.

210 Montclair School Rd, Simpsonville

Listing courtesy of 3C Property Management LLC.

$228,500

Recently updated Cozy Cottage in the heart of horse country. Situated across from rolling pastures this two bedroom home is ready for its new owner to make memories as fond as the ones of the past family. Step inside to a large entry room which could double as office, reading nook, or dining space that flows into the living room. An updated kitchen invites you in with a large center island that has enough seating for 6 or more for those nights of entertaining. Beautiful brand new kitchen cabinets along with butcherblock countertops and shiplap backsplash, bring a cozy cottage feel while the brushed gold fixtures add a modern element. Follow the new LVP floors down the hall to find 2 bedrooms, 2 closets, and a fully updated full bathroom with marble vanity and gold fixtures. Don't miss out Schedule your showing today!

2 Beds ⋅ 1 Baths ⋅ 1723074 MLS

Recently updated Cozy Cottage in the heart of horse country. Situated across from rolling pastures this two bedroom home is ready for its new owner to make memories as fond as the ones of the past family. Step inside to a large entry room which could double as office, reading nook, or dining space that flows into the living room. An updated kitchen invites you in with a large center island that has enough seating for 6 or more for those nights of entertaining. Beautiful brand new kitchen cabinets along with butcherblock countertops and shiplap backsplash, bring a cozy cottage feel while the brushed gold fixtures add a modern element. Follow the new LVP floors down the hall to find 2 bedrooms, 2 closets, and a fully updated full bathroom with marble vanity and gold fixtures. Don't miss out Schedule your showing today!

3936 Aiken Rd, Simpsonville

Listing courtesy of EXP Realty LLC.

$459,900

Welcome to this exceptional 4 BEDROOM + 2 1/2 BATH NEW CONSTRUCTION home in the highly sought-after Villas at Cardinal Club. Offering 1,990 square feet of thoughtfully designed living space, this home delivers the perfect balance of style, comfort, and functionality. This home features a spacious first-floor primary suite, providing privacy and convenience, while three additional bedrooms upstairs offer beautiful views and share a generous full bath with a double vanity. The open-concept design seamlessly connects the kitchen, dining, and living areas, creating an inviting space for everyday living and effortless entertaining. A conveniently located powder room is tucked just off the hallway, thoughtfully positioned away from the kitchen--and you should see the premium appliances! Every detail has been carefully considered, from the smart layout to the quality finishes, making this home as practical as it is beautiful. Located in the coveted Villas at Cardinal Club community in Simpsonville, this home is nestled in one of the area's most desirable neighborhoods. This is your opportunity to own a brand-new home without a lengthy build timeline. Don't miss your chance to make this beautiful new home yours.

4 Beds ⋅ 3 Baths ⋅ 1722161 MLS

Welcome to this exceptional 4 BEDROOM + 2 1/2 BATH NEW CONSTRUCTION home in the highly sought-after Villas at Cardinal Club. Offering 1,990 square feet of thoughtfully designed living space, this home delivers the perfect balance of style, comfort, and functionality. This home features a spacious first-floor primary suite, providing privacy and convenience, while three additional bedrooms upstairs offer beautiful views and share a generous full bath with a double vanity. The open-concept design seamlessly connects the kitchen, dining, and living areas, creating an inviting space for everyday living and effortless entertaining. A conveniently located powder room is tucked just off the hallway, thoughtfully positioned away from the kitchen--and you should see the premium appliances! Every detail has been carefully considered, from the smart layout to the quality finishes, making this home as practical as it is beautiful. Located in the coveted Villas at Cardinal Club community in Simpsonville, this home is nestled in one of the area's most desirable neighborhoods. This is your opportunity to own a brand-new home without a lengthy build timeline. Don't miss your chance to make this beautiful new home yours.

1204 Divot Way, Simpsonville

Listing courtesy of Torrey Smith Realty Co., LLC.

$218,900

Per the development plan, this is the largest unit in the complex. Custom built as handicapped accessible but these modifications would benefit anyone- wider hallways and door openings, step-in primary tiled shower with very low barrier, no steps into unit, etc. This rear corner unit means privacy for the fenced patio that many units don't have. One owner since new. You will find a very livable floorplan with good closet space and large bedrooms. The kitchen and breakfast area are open with a nice laundry room off the kitchen. Trey ceilings and several builder upgrades. Being sold to settle an estate. Unit is in good condition but estate is selling as-is. There is a clubhouse and fitness room on site. Only 66 garden-style units here. Professionally managed.

2 Beds ⋅ 2 Baths ⋅ 1721255 MLS

Per the development plan, this is the largest unit in the complex. Custom built as handicapped accessible but these modifications would benefit anyone- wider hallways and door openings, step-in primary tiled shower with very low barrier, no steps into unit, etc. This rear corner unit means privacy for the fenced patio that many units don't have. One owner since new. You will find a very livable floorplan with good closet space and large bedrooms. The kitchen and breakfast area are open with a nice laundry room off the kitchen. Trey ceilings and several builder upgrades. Being sold to settle an estate. Unit is in good condition but estate is selling as-is. There is a clubhouse and fitness room on site. Only 66 garden-style units here. Professionally managed.

850 Garden Pointe Dr, Simpsonville

Listing courtesy of THINK Real Estate LLC.

$205,000

Nice 2 bedroom condo conveniently located in the desirable town of Simpsonville. This condo features 2 bedrooms, Family room with tray ceiling, eat-in Kitchen, laundry room and 1.5 baths. The buyer of this condo unit can enjoy time outside on the covered front porch or the private back yard.

2 Beds ⋅ 2 Baths ⋅ 1721151 MLS

Nice 2 bedroom condo conveniently located in the desirable town of Simpsonville. This condo features 2 bedrooms, Family room with tray ceiling, eat-in Kitchen, laundry room and 1.5 baths. The buyer of this condo unit can enjoy time outside on the covered front porch or the private back yard.

816 Garden Pointe Dr, Simpsonville

Listing courtesy of Coldwell Banker Larry Rogers.

$325,000

Built in 2022 in the heart of Simpsonville, this beautifully designed home sits on a quiet street with a wooded lot that offers both privacy and charm. This home is currently used as a furnished short term rental but would also be a great full time residence! Step inside to a completely open first floor where the living room, dining area, and kitchen flow seamlessly together - perfect for entertaining. The kitchen features custom wood cabinetry and granite countertops, while a half bath and mechanical closet complete the main level. Upstairs, you'll find two guest bedrooms, a full bathroom, convenient second-floor laundry, and a spacious primary suite with an en suite bath and two closets. Outside, enjoy a deck overlooking the backyard, creating the perfect space to relax or gather with friends and family.

3 Beds ⋅ 3 Baths ⋅ 1718653 MLS

Built in 2022 in the heart of Simpsonville, this beautifully designed home sits on a quiet street with a wooded lot that offers both privacy and charm. This home is currently used as a furnished short term rental but would also be a great full time residence! Step inside to a completely open first floor where the living room, dining area, and kitchen flow seamlessly together - perfect for entertaining. The kitchen features custom wood cabinetry and granite countertops, while a half bath and mechanical closet complete the main level. Upstairs, you'll find two guest bedrooms, a full bathroom, convenient second-floor laundry, and a spacious primary suite with an en suite bath and two closets. Outside, enjoy a deck overlooking the backyard, creating the perfect space to relax or gather with friends and family.

310 E Main St, Simpsonville

Listing courtesy of Lenihan Sotheby's Int'l Realty.