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Charming Cape Cod in a desirable Highlands-area location, just minutes from Bardstown Road, the Douglass Loop, Cherokee Park, and an abundance of local dining and shopping! A welcoming covered front porch invites you inside, where hardwood floors flow throughout the first floor. The living room features a fireplace flanked by beautiful built-in bookcases, while the adjoining dining room offers its own special charm with dual corner built-in cabinets. Beyond, the kitchen opens to a spacious, vaulted family room filled with natural light from an abundance of windows and glass doors overlooking the backyard. This inviting, open-concept gathering space is ideal for both everyday living and entertaining. Two bedrooms and a full bath complete the first floor, while the expansive upper level offers a private bedroom suite with a walk-in closet and full bath. With bedrooms and full baths on both levels, the versatile layout provides the option of a first- or second-floor primary suite. The unfinished basement houses the laundry and offers abundant storage space. Outside, a multi-tier deck overlooks the partially privacy-fenced backyard, where mature trees provide a lovely backdrop of shade and greenery. A detached 2.5-car garage adds convenience and additional storage. Recent improvements include a new water heater (2025), replacement living room windows (2025), and roof (2023). See Seller Disclosure for additional updates. Enjoy the character of a classic Cape Cod with the space and flexibility to suit today's lifestyle! Seller is offering a one-year America's Preferred Home Warranty for added peace of mind.

3 Beds ⋅ 2 Baths ⋅ 1733352 MLS

Charming Cape Cod in a desirable Highlands-area location, just minutes from Bardstown Road, the Douglass Loop, Cherokee Park, and an abundance of local dining and shopping! A welcoming covered front porch invites you inside, where hardwood floors flow throughout the first floor. The living room features a fireplace flanked by beautiful built-in bookcases, while the adjoining dining room offers its own special charm with dual corner built-in cabinets. Beyond, the kitchen opens to a spacious, vaulted family room filled with natural light from an abundance of windows and glass doors overlooking the backyard. This inviting, open-concept gathering space is ideal for both everyday living and entertaining. Two bedrooms and a full bath complete the first floor, while the expansive upper level offers a private bedroom suite with a walk-in closet and full bath. With bedrooms and full baths on both levels, the versatile layout provides the option of a first- or second-floor primary suite. The unfinished basement houses the laundry and offers abundant storage space. Outside, a multi-tier deck overlooks the partially privacy-fenced backyard, where mature trees provide a lovely backdrop of shade and greenery. A detached 2.5-car garage adds convenience and additional storage. Recent improvements include a new water heater (2025), replacement living room windows (2025), and roof (2023). See Seller Disclosure for additional updates. Enjoy the character of a classic Cape Cod with the space and flexibility to suit today's lifestyle! Seller is offering a one-year America's Preferred Home Warranty for added peace of mind.

2006 Winston Ave, Louisville

Listing courtesy of simpler.realestate.

$449,000

3 Beds ⋅ 3 Baths ⋅ 1732339 MLS

2124 Winston Ave, Louisville

Listing courtesy of Keller Williams Collective.

$389,900

Welcome to 2021 Winston Avenue, a charming 3-bedroom, 2-bath Cape Cod located in the heart of the Highlands! Surrounded by beautiful homes and ideally located in one of Louisville's most beloved neighborhoods, this inviting home blends classic character with thoughtful updates and a wonderfully livable floor plan. Inside you'll find a warm and welcoming living room featuring a fireplace, built-in cabinetry, beautiful hardwood floors, and an abundance of natural light. Hardwood floors flow throughout the entire first floor, adding warmth and timeless character to the home. The spacious dining room flows effortlessly into the family room, where built-in bookcases and plentiful windows create a comfortable gathering space. The adjacent informal dining area and thoughtfully designed kitchen make everyday living and entertaining feel effortless, with the kitchen opening directly to the family room with a high ceiling. Two bedrooms are conveniently located on the first floor, including one with a large walk-in closet. A nicely renovated hall bathroom features beautiful marble tile and a low-threshold shower, adding a fresh, stylish touch. Upstairs, discover a spacious open bedroom retreat with new paint and new carpet, generous closet space, including a cedar-lined closet, and a full bathroom. This private and versatile space is perfect for a primary suite, guest retreat, home office, or whatever best suits your lifestyle. The large unfinished basement offers exciting potential for future expansion, recreation, storage, or additional living space. Outside, enjoy a deck overlooking the partially fenced yard, perfect for relaxing, entertaining, or enjoying a quiet evening. A convenient one-car garage provides additional parking and storage. Recent updates include a newer roof and gutters, along with the freshly painted and newly carpeted upstairs, providing added appeal and peace of mind. With its inviting spaces, classic Cape Cod charm, hardwood floors throughout the first floor, built-ins, flexible living areas, and fantastic Highlands location, 2021 Winston Avenue is a home you'll be excited to make your own. Come see all the character and possibilities this special property has to offer!

3 Beds ⋅ 2 Baths ⋅ 1730036 MLS

Welcome to 2021 Winston Avenue, a charming 3-bedroom, 2-bath Cape Cod located in the heart of the Highlands! Surrounded by beautiful homes and ideally located in one of Louisville's most beloved neighborhoods, this inviting home blends classic character with thoughtful updates and a wonderfully livable floor plan. Inside you'll find a warm and welcoming living room featuring a fireplace, built-in cabinetry, beautiful hardwood floors, and an abundance of natural light. Hardwood floors flow throughout the entire first floor, adding warmth and timeless character to the home. The spacious dining room flows effortlessly into the family room, where built-in bookcases and plentiful windows create a comfortable gathering space. The adjacent informal dining area and thoughtfully designed kitchen make everyday living and entertaining feel effortless, with the kitchen opening directly to the family room with a high ceiling. Two bedrooms are conveniently located on the first floor, including one with a large walk-in closet. A nicely renovated hall bathroom features beautiful marble tile and a low-threshold shower, adding a fresh, stylish touch. Upstairs, discover a spacious open bedroom retreat with new paint and new carpet, generous closet space, including a cedar-lined closet, and a full bathroom. This private and versatile space is perfect for a primary suite, guest retreat, home office, or whatever best suits your lifestyle. The large unfinished basement offers exciting potential for future expansion, recreation, storage, or additional living space. Outside, enjoy a deck overlooking the partially fenced yard, perfect for relaxing, entertaining, or enjoying a quiet evening. A convenient one-car garage provides additional parking and storage. Recent updates include a newer roof and gutters, along with the freshly painted and newly carpeted upstairs, providing added appeal and peace of mind. With its inviting spaces, classic Cape Cod charm, hardwood floors throughout the first floor, built-ins, flexible living areas, and fantastic Highlands location, 2021 Winston Avenue is a home you'll be excited to make your own. Come see all the character and possibilities this special property has to offer!

2021 Winston Ave, Louisville

Listing courtesy of Rainey Allen Shaw East.

$600,000

Nestled in the heart of the highly sought-after Strathmoor Manor neighborhood, this classic Highlands Cape Cod perfectly blends timeless charm with modern comfort. Just minutes from the restaurants, coffee shops, and local boutiques lining Bardstown Road, this location also offers easy access to some of Louisville's most beloved parks, the Louisville Zoo, Bellarmine University, and is only a couple blocks from Atherton High School and Assumption High School. From the moment you step inside, this home absolutely oozes charm with gorgeous hardwood floors, detailed molding, beautiful windows, spacious rooms, and a cozy fireplace anchoring the living room. The main floor offers a wonderful flow with a large living room, dedicated dining room, and an updated eat-in kitchen featuring plenty of modern touches while still honoring the character of the home. Three bedrooms and two full bathrooms complete the first floor. Just beyond the living spaces, a screened-in porch overlooks what truly feels like a private garden oasis. The beautifully landscaped yard offers exceptional privacy and the perfect setting for relaxing mornings, entertaining friends, or simply enjoying nature. Upstairs, the fully renovated second floor is spectacular with soaring high ceilings and oversized windows that flood the space with natural light. Whether used as an incredible primary suite with walk-in closet, a second family room, art studio, or dual home offices, the possibilities are endless. This is the kind of home that rarely comes along — full of warmth, personality, and classic Highlands character in one of Louisville's most beloved neighborhoods.

3 Beds ⋅ 2 Baths ⋅ 1716997 MLS

Nestled in the heart of the highly sought-after Strathmoor Manor neighborhood, this classic Highlands Cape Cod perfectly blends timeless charm with modern comfort. Just minutes from the restaurants, coffee shops, and local boutiques lining Bardstown Road, this location also offers easy access to some of Louisville's most beloved parks, the Louisville Zoo, Bellarmine University, and is only a couple blocks from Atherton High School and Assumption High School. From the moment you step inside, this home absolutely oozes charm with gorgeous hardwood floors, detailed molding, beautiful windows, spacious rooms, and a cozy fireplace anchoring the living room. The main floor offers a wonderful flow with a large living room, dedicated dining room, and an updated eat-in kitchen featuring plenty of modern touches while still honoring the character of the home. Three bedrooms and two full bathrooms complete the first floor. Just beyond the living spaces, a screened-in porch overlooks what truly feels like a private garden oasis. The beautifully landscaped yard offers exceptional privacy and the perfect setting for relaxing mornings, entertaining friends, or simply enjoying nature. Upstairs, the fully renovated second floor is spectacular with soaring high ceilings and oversized windows that flood the space with natural light. Whether used as an incredible primary suite with walk-in closet, a second family room, art studio, or dual home offices, the possibilities are endless. This is the kind of home that rarely comes along — full of warmth, personality, and classic Highlands character in one of Louisville's most beloved neighborhoods.

2020 Winston Ave, Louisville

Listing courtesy of Keller Williams Collective.

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