3 - Brownsboro Rd / Crescent Hill / St Matthews Homes with Bungalow Style

3 - Brownsboro Rd / Crescent Hill / St Matthews Homes with Bungalow Style

Welcome to the charming neighborhoods of Brownsboro Road, Crescent Hill, and St. Matthews, nestled in the heart of Louisville, Kentucky. This vibrant region is a delightful blend of suburban tranquility and urban convenience, making it one of the most sought-after areas in Jefferson County.

Brownsboro Road is known for its scenic views and lush greenery, offering residents a peaceful retreat while still being just a stone's throw away from the bustling city center. Crescent Hill, with its historic architecture and quaint shops, exudes a unique character that draws visitors and locals alike. Meanwhile, St. Matthews boasts a vibrant community atmosphere, complete with parks, restaurants, and shopping options that cater to every taste.

One of the standout features of this region is the abundance of charming bungalow-style homes. These delightful residences, characterized by their low-pitched roofs, wide front porches, and cozy interiors, embody a sense of warmth and character that is hard to resist. Perfect for families, young professionals, or retirees, these bungalows often come with beautiful gardens and ample outdoor space, making them ideal for both relaxation and entertaining.

Living in Brownsboro Road, Crescent Hill, or St. Matthews means embracing a community that values both history and modern living. With excellent schools, friendly neighbors, and a rich tapestry of cultural offerings, this area is not just a place to live; it’s a place to thrive. Whether you're looking to buy your first home or searching for a charming bungalow to call your own, this region has something special waiting for you. Come and discover the enchanting lifestyle that awaits you in Louisville!

Newest 3 - Brownsboro Rd / Crescent Hill / St Matthews Homes with Bungalow Style

4 Beds ⋅ 3 Baths ⋅ 1724361 MLS

Tucked into the heart of Crescent Hill, Winton Avenue is one Louisville's hidden gems. Quietly removed from the pace of the city, it sits just minutes from Frankfort Ave, Cherokee Park, Cliffton, St Matthews, and neighboring Mockingbird Valley, yet feels a world apart. The kind of neighborhood where neighbors know one another, front porches are well used, and coming home is something to look forward to. Built in 1913, this Craftsman has evolved over more than a century with care and intention. Each renovation has built upon the homes architectural character, creating spaces that feel true to the house while embracing the way people live today. Every decision was made with the belief that a home like this should continue to evolve without losing the qualities that made it worth preserving. The result a home that feels collected over time rather than created all at once. The kitchen flows into the living and dining rooms, making it just as well suited to everyday dinners as celebrations. The family room, front porch, screened porch, and backyard each offer a place to relax, connect, or simply enjoy the moment where conversations easily find their own place. Whether entertaining or enjoying a quiet evening at home, each space feels as natural to everyday life as it does to special occasions. More than a century after it was built, this Craftsman reflects care with which it has evolved, and the respect shown for its history along the way. It's the kind of home that feels like it has always been yours.

327 Winton Ave, Louisville

2 Beds ⋅ 1 Baths ⋅ 1724303 MLS

Welcome to Clifton Heights! Tucked away on a quiet street, this charming 2-bedroom, 1-bath home is full of character and timeless appeal. Original hardwood floors, fresh interior paint, and abundant natural light create a warm, inviting atmosphere. The updated kitchen features new appliances, while recent improvements—including a newer roof and HVAC—provide added peace of mind. The finished basement offers flexible living space ideal for a family room, game room, home office, art studio, workout area, or hobby space. Outside, enjoy a fully fenced backyard perfect for entertaining, gardening, or pets, along with the convenience of a detached 2-car garage. Combining classic charm, thoughtful updates, and a desirable Clifton Heights location just minutes from local dining, shopping, parks and downtown Louisville, this home is ready for its next chapter

2903 Lindsay Ave, Louisville

4 Beds ⋅ 2 Baths ⋅ 1722962 MLS

419 Iola Rd, Louisville

3 Beds ⋅ 2 Baths ⋅ 1721630 MLS

Welcome home to the heart of Saint Matthews and this fantastic three bedroom, two bath home! Within walking distance of Seneca Park and a multitude of shops and restaurants, here is your private oasis. You're greeted with a beautiful blend of classic elements and modern amenities in the cozy living room, large dining (or activity) room, wood floors, and kitchen with granite countertops. Enjoy a coffee on the lovely screened in porch overlooking your new backyard. Upstairs you'll find 3 bedrooms with a walk in closet in the primary and a second bathroom along with a second HVAC unit for better upstairs temperature control. Complete with a full unfinished basement that has been professionally waterproofed for plenty of storage and a detached garage, this house has everything you need.

208 Oxford Pl, Louisville

2 Beds ⋅ 2 Baths ⋅ 1718615 MLS

New roof July, 2026! 2 yr workmanship warranty. This 1922 Craftsman-style bungalow was built from the Sears & Roebuck catalog as the "The Osborn" model. It blends traditional American craftsman home style with subtle Japanese influences and sits in the desirable St. Matthews / Crescent Hill corridor. The inviting front porch with swing offers a perfect spot to relax. Inside, you'll find classic Craftsman details including rich woodworking, handsome trim, original doors, and golden oak hardwood flooring throughout. The layout features a large living room with fireplace, dining room, kitchen, two spacious bedrooms, and two offices—ideal for work or hobbies. Upstairs, a large bonus attic provides excellent space for future expansion or storage. The partially finished basement is oversized and includes a full bath, offering flexible options for a guest area, gym, or rec room. Outside, a large covered deck off of the first floor office space you will find paver sidewalk ways & patio, which is surrounded by your private, 6-foot fenced and gated backyard. The landscaping includes a Japanese maple, a cherry blossom tree, and 2 large cherry crepe myrtles. Your detached garage with paver walkway is sized like a two-car—provides ample room for one vehicle and additional storage. This well-built Sears kit home delivers historic character, practical living space, and a convenient location in one of Louisville's most sought-after corridors. Ready for your updates and enjoyment. Please note, court approval required as this is an estate home. Call your favorite Realtor today for a showing.

115 Cannons Ln, Louisville

4 Beds ⋅ 2 Baths ⋅ 1717962 MLS

Charming home in Cresent Hill with easy walking access to restaurants, shopping, parks and downtown. The inviting covered front porch is the perfect spot to sit in the swing and relax. As you enter the home thru the front door you will find a wonderful living room that's open to the dinning area and kitchen there is also a cozy sunroom just off the kitchen. Newer kitchen cabinets and stainless steel appliances along with butcher block counter tops and lots of natural light complete the open floor plan. Just off the kitchen is a wood deck for relaxing and the steps lead down to a completed fenced yard with plenty of shade that backs up to a wooded area with a beautiful natural rock wall. Hardwood floors thru out the home. There are 3 nice size bedrooms and one smaller. Come see for yourself

2611 Grinstead Dr, Louisville

2 Beds ⋅ 2 Baths ⋅ 1715677 MLS

Charming and full of character, this classic 2-story home offers style and everyday convenience. Inside, you'll find beautiful inlaid hardwood floors, abundant natural light, and living and dining rooms that feel warm and inviting. The enclosed front porch adds the perfect bonus space for morning coffee, reading, or just relaxing year-round. The kitchen features ample cabinetry and connects to a cozy breakfast nook/flex space. A convenient half bath is located off the kitchen. Upstairs offers generously sized bedrooms, including a spacious primary suite and a sitting room that could serve as a home office, dressing room, or private retreat. The basement offers additional storage space. The 3 car detached garage offers space for cars, bikes, lawn equipment and potential for a workshop. A rare opportunity to own a character-filled home in an unbeatable location where parks, restaurants, and Crescent Hill conveniences are just minutes away.

170 McCready Ave, Louisville

2 Beds ⋅ 2 Baths ⋅ 1715560 MLS

Stunning! Whether looking for a place to call home or your next investment opportunity, you'll want to check out 2041 Payne Street. This property was fully overhauled in 2022 including an all-new kitchen (including granite countertops, new appliances, custom built-ins and open shelving), 2 new full bathrooms and a new hallway laundry room. You'll love the gorgeous and low maintenance hardwood floors throughout. 2022 updates include: roof on house and garage, upgraded HVAC systems with additional ductwork, all new electrical and upgraded plumbing with a 50-gallon electric hot water heater, all new interior trim, a new front porch including newly poured porch pad and trim work, as well as a new side porch entrance. This house has a 4-car garage (yes, a 4-car garage!) and is situated on a double lot. Zoned R-4, expansion and development opportunities await. This house has most recently been used as an executive / traveling healthcare professional rental generating consistent income.

2041 Payne St, Louisville

4 Beds ⋅ 2 Baths ⋅ 1694192 MLS

Charming Updated Duplex in Clifton/Crescent Hill - Income-Producing Opportunity & Just Appraised Excellent investment opportunity in one of Louisville's most desirable neighborhoods! This well-maintained duplex offers two spacious units and is currently generating income with Unit 1 operating as a successful Airbnb. Features include numerous updates throughout, a large unfinished basement perfect for storage or expansion potential, and a detached 2-car garage. Located in the heart of Clifton/Crescent Hill, this property offers unbeatable access to local shops, restaurants, parks, and downtown Louisville. Whether you're looking to continue as a short-term rental, house-hack by living in one unit and renting the other, or build your long-term portfolio, this duplex checks all the boxe Additional Highlights: " Updated kitchens and baths " Private entrances for each unit " Ample off-street parking " Spacious backyard " Flexible layout with strong rental history Don't miss your chance to own a turn-key property in a prime location! Per seller, roof has lifetime transferable warranty.

153 N Bellaire Ave, Louisville

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