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This extraordinary three-story brick residence is a rare offering in one of Louisville's most coveted neighborhoods, moments from the scenic beauty of Cherokee Park. Masterfully blending timeless architecture with refined, modern updates, this home delivers an elevated living experience defined by scale, craftsmanship, and thoughtful design. Spanning over 4,100 finished square feet across three levels, with an additional 1,650 square feet ready to be customized in the lower level, the home offers remarkable versatility. Two primary suites, including a main level option, six fireplaces, and a four-car garage with a dedicated workshop create a level of functionality rarely found in homes of this scale and character. A stately front porch with classic columns, a charming swing, and striking leaded glass double doors sets an elegant tone upon arrival. Inside, the grand foyer showcases a beautifully restored staircase, soaring ceilings, intricate millwork, and rich hardwood floors that seamlessly carry throughout the home. Formal living and dining spaces exude sophistication, each anchored by one of the home's fireplaces and enhanced by custom built-ins. The gourmet kitchen is both stunning and functional, featuring extensive custom cabinetry, generous prep space, a statement hood, granite countertops, tiled backsplash, six-burner gas cooktop, and premium stainless steel appliances. Designed for both everyday living and entertaining, the kitchen opens effortlessly to one of two outdoor living spaces. The backyard is a true private retreat. Thoughtfully designed and impeccably maintained, it features lush landscaping, a paved firepit area, an 8-foot privacy fence, a separately metered irrigation system, and a grilling station with a dedicated gas line. The detached four-car garage has been architecturally integrated to complement the home, creating a cohesive and elevated outdoor setting ideal for entertaining or quiet evenings at home. The main level primary suite offers a luxurious escape, complete with an updated bath featuring a jetted soaking tub and a custom walk-in closet. A powder room completes the first level. Upstairs, four additional bedrooms provide generous accommodations, along with a beautifully updated full bath. The second primary suite on this level is a standout, offering a spa-like bathroom with heated floors. One bedroom enjoys direct access to the second-level deck and features dual walk-in closets. A secondary laundry hookup adds convenience and flexibility. The third level presents an exceptional bonus space, perfect for a private lounge, media room, or guest retreat, complete with a wet bar, built-in shelving, and a half bath. Extensive updates further enhance the home's appeal, including updated HVAC systems, whole house electric generator, restored windows and doors preserving original character, custom iron railings, refreshed hardscaping, and a gas fireplace addition. Perfectly positioned near the vibrant dining, shopping, and lifestyle amenities of Bardstown Road, this remarkable property offers the best of historic charm and modern luxury in one of Louisville's most iconic settings.

5 Beds ⋅ 5 Baths ⋅ 1720182 MLS

This extraordinary three-story brick residence is a rare offering in one of Louisville's most coveted neighborhoods, moments from the scenic beauty of Cherokee Park. Masterfully blending timeless architecture with refined, modern updates, this home delivers an elevated living experience defined by scale, craftsmanship, and thoughtful design. Spanning over 4,100 finished square feet across three levels, with an additional 1,650 square feet ready to be customized in the lower level, the home offers remarkable versatility. Two primary suites, including a main level option, six fireplaces, and a four-car garage with a dedicated workshop create a level of functionality rarely found in homes of this scale and character. A stately front porch with classic columns, a charming swing, and striking leaded glass double doors sets an elegant tone upon arrival. Inside, the grand foyer showcases a beautifully restored staircase, soaring ceilings, intricate millwork, and rich hardwood floors that seamlessly carry throughout the home. Formal living and dining spaces exude sophistication, each anchored by one of the home's fireplaces and enhanced by custom built-ins. The gourmet kitchen is both stunning and functional, featuring extensive custom cabinetry, generous prep space, a statement hood, granite countertops, tiled backsplash, six-burner gas cooktop, and premium stainless steel appliances. Designed for both everyday living and entertaining, the kitchen opens effortlessly to one of two outdoor living spaces. The backyard is a true private retreat. Thoughtfully designed and impeccably maintained, it features lush landscaping, a paved firepit area, an 8-foot privacy fence, a separately metered irrigation system, and a grilling station with a dedicated gas line. The detached four-car garage has been architecturally integrated to complement the home, creating a cohesive and elevated outdoor setting ideal for entertaining or quiet evenings at home. The main level primary suite offers a luxurious escape, complete with an updated bath featuring a jetted soaking tub and a custom walk-in closet. A powder room completes the first level. Upstairs, four additional bedrooms provide generous accommodations, along with a beautifully updated full bath. The second primary suite on this level is a standout, offering a spa-like bathroom with heated floors. One bedroom enjoys direct access to the second-level deck and features dual walk-in closets. A secondary laundry hookup adds convenience and flexibility. The third level presents an exceptional bonus space, perfect for a private lounge, media room, or guest retreat, complete with a wet bar, built-in shelving, and a half bath. Extensive updates further enhance the home's appeal, including updated HVAC systems, whole house electric generator, restored windows and doors preserving original character, custom iron railings, refreshed hardscaping, and a gas fireplace addition. Perfectly positioned near the vibrant dining, shopping, and lifestyle amenities of Bardstown Road, this remarkable property offers the best of historic charm and modern luxury in one of Louisville's most iconic settings.

2110 Bonnycastle Ave, Louisville

Listing courtesy of Lenihan Sotheby's Int'l Realty. Selling Office: .

$499,000

For the first time in over 40 years, this beloved 1920s Craftsman bungalow is being offered to the market by only the second owner. This is a rare opportunity to own a piece of the Highlands' architectural history. Set behind a classic covered wrap around front porch and framed by mature trees, the home welcomes you through its stained-glass entry door, hand-set with a striking tulip motif, a beautiful showpiece. Inside, the living room is anchored by a fireplace flanked by matching built-in glass-front bookcases and crowned with a coordinating stained-glass windows. Enjoy wide baseboards, and hardwood floors with inlaid detail borders flow throughout the main living areas, offering original details that is hard to find. A butler's pantry connects the dining room to the kitchen, showcasing built-in glass-front cabinetry and a vintage stained-glass pendant light overhead. The kitchen itself retains its period charm with tile flooring and Mackintosh tile accents, and a period-style back door opening onto a screened-in porch overlooking the private backyard. Two bedrooms on the main level feature picture-rail molding and original wood doors and trim. Hall bathroom with mosaic black and white tile, with cast iron bathtub and a separate water closet. The upper level offers a peaceful primary retreat with vaulted ceilings, dormer windows, and two spacious walk-in closets with primary ensuite. Full basement with garage and alley-way access round out the house. Just moments from Cherokee Park and the shops and restaurants of Bardstown Road, this home allows a rare chance to own a fully intact Craftsman original in one of Louisville's most sought-after neighborhoods.

4 Beds ⋅ 3 Baths ⋅ 1723274 MLS

For the first time in over 40 years, this beloved 1920s Craftsman bungalow is being offered to the market by only the second owner. This is a rare opportunity to own a piece of the Highlands' architectural history. Set behind a classic covered wrap around front porch and framed by mature trees, the home welcomes you through its stained-glass entry door, hand-set with a striking tulip motif, a beautiful showpiece. Inside, the living room is anchored by a fireplace flanked by matching built-in glass-front bookcases and crowned with a coordinating stained-glass windows. Enjoy wide baseboards, and hardwood floors with inlaid detail borders flow throughout the main living areas, offering original details that is hard to find. A butler's pantry connects the dining room to the kitchen, showcasing built-in glass-front cabinetry and a vintage stained-glass pendant light overhead. The kitchen itself retains its period charm with tile flooring and Mackintosh tile accents, and a period-style back door opening onto a screened-in porch overlooking the private backyard. Two bedrooms on the main level feature picture-rail molding and original wood doors and trim. Hall bathroom with mosaic black and white tile, with cast iron bathtub and a separate water closet. The upper level offers a peaceful primary retreat with vaulted ceilings, dormer windows, and two spacious walk-in closets with primary ensuite. Full basement with garage and alley-way access round out the house. Just moments from Cherokee Park and the shops and restaurants of Bardstown Road, this home allows a rare chance to own a fully intact Craftsman original in one of Louisville's most sought-after neighborhoods.

2221 Bonnycastle Ave, Louisville

Listing courtesy of White Picket Real Estate. Selling Office: .

$495,000

Welcome to 2018 Sherwood Avenue, a classic Parkside Highlands home filled with character, charm, and beautiful original details. Perfectly situated in one of Louisville's most desirable neighborhoods, this 4 bedroom, 1.5 bath home offers 2,235 square feet of living space in a highly sought after location. A large inviting front porch sets the tone before stepping inside to a gracious foyer with an impressive staircase, gorgeous millwork, and timeless architectural details. The first floor features 10-foot ceilings, beautiful hardwood floors, oversized windows, and an abundance of natural light throughout. The spacious living room offers a decorative fireplace, inlaid hardwood floors, and French doors that open into the formal dining room, creating a wonderful flow for everyday living and entertaining. A convenient half bath completes the first floor. The second level offers four bedrooms and hardwood floors throughout. A former rear porch has been thoughtfully transformed into a bright and functional second-floor laundry area, office, or art studio, complete with newer windows and a natural wood beadboard ceiling. The home also features 23 replaced efficiency windows, adding comfort while preserving the home's historic feel. The partially finished third floor offers approximately 300 square feet of additional flexible space that could be used as a playroom, office, studio, or extra storage. With its Parkside Highlands location, original character, generous square footage, and thoughtful updates, this home is a rare opportunity in one of Louisville's most beloved neighborhoods.

4 Beds ⋅ 2 Baths ⋅ 1726956 MLS

Welcome to 2018 Sherwood Avenue, a classic Parkside Highlands home filled with character, charm, and beautiful original details. Perfectly situated in one of Louisville's most desirable neighborhoods, this 4 bedroom, 1.5 bath home offers 2,235 square feet of living space in a highly sought after location. A large inviting front porch sets the tone before stepping inside to a gracious foyer with an impressive staircase, gorgeous millwork, and timeless architectural details. The first floor features 10-foot ceilings, beautiful hardwood floors, oversized windows, and an abundance of natural light throughout. The spacious living room offers a decorative fireplace, inlaid hardwood floors, and French doors that open into the formal dining room, creating a wonderful flow for everyday living and entertaining. A convenient half bath completes the first floor. The second level offers four bedrooms and hardwood floors throughout. A former rear porch has been thoughtfully transformed into a bright and functional second-floor laundry area, office, or art studio, complete with newer windows and a natural wood beadboard ceiling. The home also features 23 replaced efficiency windows, adding comfort while preserving the home's historic feel. The partially finished third floor offers approximately 300 square feet of additional flexible space that could be used as a playroom, office, studio, or extra storage. With its Parkside Highlands location, original character, generous square footage, and thoughtful updates, this home is a rare opportunity in one of Louisville's most beloved neighborhoods.

2018 Sherwood Ave, Louisville

Listing courtesy of BERKSHIRE HATHAWAY HomeServices, Parks & Weisberg Realtors. Selling Office: .

$495,000

Back on market due to no fault of sellers. Beautifully renovated brick 2-story in the heart of St. Matthews, offering a perfect blend of classic charm, modern updates & walkability. The inviting foyer and staircase create a welcoming first impression, leading into a spacious living room featuring charming built-ins and a fireplace. Thoughtful renovations have opened the kitchen and dining areas, creating a seamless flow ideal for everyday living and entertaining. A convenient half bath completes the main level. Just off the kitchen, enjoy a large deck overlooking a beautifully landscaped backyard, along with an oversized one-car garage for added functionality. Upstairs, you'll find three generously sized bedrooms and a well-appointed full bathroom, with an additional third-floor bonus space perfect for a home office, playroom, or flex space. The fully finished walk-up basement offers even more living space, including a second living area, bonus room, and full bathroom with direct access to the backyard. Recent updates include a newer roof (2023). Ideally located with easy access to local shops, restaurants, parks, and everyday conveniences that make St. Matthews so desirable.

3 Beds ⋅ 3 Baths ⋅ 1714454 MLS

Back on market due to no fault of sellers. Beautifully renovated brick 2-story in the heart of St. Matthews, offering a perfect blend of classic charm, modern updates & walkability. The inviting foyer and staircase create a welcoming first impression, leading into a spacious living room featuring charming built-ins and a fireplace. Thoughtful renovations have opened the kitchen and dining areas, creating a seamless flow ideal for everyday living and entertaining. A convenient half bath completes the main level. Just off the kitchen, enjoy a large deck overlooking a beautifully landscaped backyard, along with an oversized one-car garage for added functionality. Upstairs, you'll find three generously sized bedrooms and a well-appointed full bathroom, with an additional third-floor bonus space perfect for a home office, playroom, or flex space. The fully finished walk-up basement offers even more living space, including a second living area, bonus room, and full bathroom with direct access to the backyard. Recent updates include a newer roof (2023). Ideally located with easy access to local shops, restaurants, parks, and everyday conveniences that make St. Matthews so desirable.

219 Norbourne Blvd, Louisville

Listing courtesy of Keller Williams Collective. Selling Office: .

$443,000

Welcome to 233 Monohan Drive. Located in the heart of St.Matthews. This great home comes with 4 bedrooms and 3 and a half bathrooms and over 2,000 finished square feet of stylish and functional living space. Recently renovated throughout, the first floor primary suite provides convenience and privacy, while the spacious layout is perfect for both everyday living and entertaining. Enjoy your morning coffee and relaxing evenings on the back deck overlooking the yard. With so many updated finishes throughout and unbeatable location close to shopping, great dining, fantastic schools, and parks just minutes away, this move in ready home is one you won't want to miss. Schedule your private showing today!

4 Beds ⋅ 4 Baths ⋅ 1723466 MLS

Welcome to 233 Monohan Drive. Located in the heart of St.Matthews. This great home comes with 4 bedrooms and 3 and a half bathrooms and over 2,000 finished square feet of stylish and functional living space. Recently renovated throughout, the first floor primary suite provides convenience and privacy, while the spacious layout is perfect for both everyday living and entertaining. Enjoy your morning coffee and relaxing evenings on the back deck overlooking the yard. With so many updated finishes throughout and unbeatable location close to shopping, great dining, fantastic schools, and parks just minutes away, this move in ready home is one you won't want to miss. Schedule your private showing today!

233 Monohan Dr, Louisville

Listing courtesy of RE/MAX Premier Properties. Selling Office: .

$390,000

Welcome to 231 S Hubbards Ln in the desirable St. Matthews area, a well-maintained 3-bedroom, 2-bath home offering thoughtful updates and highly functional living spaces. This home blends warm character with everyday practicality, featuring a welcoming living room with a fireplace that serves as a natural focal point. The dining area opens seamlessly into a bright sunroom, creating an inviting space filled with natural light and versatile use. The kitchen, previously remodeled, is equipped with white cabinetry, granite countertops, and stainless steel appliances, delivering both style and efficiency. The main level includes two bedrooms and a full bath, offering convenience and accessibility. The second level is dedicated to a truly expansive primary bedroom, featuring updated flooring (installed approximately two years ago), three closets, and independent climate control with an almost new mini-split system for personalized comfort. The en-suite bath has been thoughtfully remodeled and includes a double vanity and a standing shower, creating a well-appointed and functional retreat. Additional features include an unfinished basement with ample storage potential and washer/dryer hookups. Exterior highlights include a fully fenced backyard with mature trees and a deck, providing a private outdoor setting. A recently added blacktop driveway enhances both functionality and curb appeal. The one-car detached garage has had its roof and select decking boards replaced and is being sold as-is. Ideally located near Baptist Health Louisville, with convenient access to the dining and retail corridors along Breckenridge Lane and Shelbyville Road, this location offers proximity to a variety of restaurants, coffee shops, and everyday amenities, as well as quick access to Mall St. Matthews and Oxmoor Center. Impeccably maintained, this home offers a compelling combination of updates, space, and location. I almost forgot, the Seller says she has quiet neighbors! Schedule your private showing today. (Showings begin Thursday Morning the 7th at 9AM.

3 Beds ⋅ 2 Baths ⋅ 1716399 MLS

Welcome to 231 S Hubbards Ln in the desirable St. Matthews area, a well-maintained 3-bedroom, 2-bath home offering thoughtful updates and highly functional living spaces. This home blends warm character with everyday practicality, featuring a welcoming living room with a fireplace that serves as a natural focal point. The dining area opens seamlessly into a bright sunroom, creating an inviting space filled with natural light and versatile use. The kitchen, previously remodeled, is equipped with white cabinetry, granite countertops, and stainless steel appliances, delivering both style and efficiency. The main level includes two bedrooms and a full bath, offering convenience and accessibility. The second level is dedicated to a truly expansive primary bedroom, featuring updated flooring (installed approximately two years ago), three closets, and independent climate control with an almost new mini-split system for personalized comfort. The en-suite bath has been thoughtfully remodeled and includes a double vanity and a standing shower, creating a well-appointed and functional retreat. Additional features include an unfinished basement with ample storage potential and washer/dryer hookups. Exterior highlights include a fully fenced backyard with mature trees and a deck, providing a private outdoor setting. A recently added blacktop driveway enhances both functionality and curb appeal. The one-car detached garage has had its roof and select decking boards replaced and is being sold as-is. Ideally located near Baptist Health Louisville, with convenient access to the dining and retail corridors along Breckenridge Lane and Shelbyville Road, this location offers proximity to a variety of restaurants, coffee shops, and everyday amenities, as well as quick access to Mall St. Matthews and Oxmoor Center. Impeccably maintained, this home offers a compelling combination of updates, space, and location. I almost forgot, the Seller says she has quiet neighbors! Schedule your private showing today. (Showings begin Thursday Morning the 7th at 9AM.

231 S Hubbards Ln, Louisville

Listing courtesy of simpler.realestate. Selling Office: .

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