8 - Douglas Hills / Hurstbourne / Middletown / Anchorage Homes with Entry Side Parking

8 - Douglas Hills / Hurstbourne / Middletown / Anchorage Homes with Entry Side Parking

Welcome to the charming neighborhoods of Douglas Hills, Hurstbourne, Middletown, and Anchorage, nestled in the heart of Jefferson County, Kentucky. This vibrant region, part of the bustling city of Louisville, offers a unique blend of suburban tranquility and urban convenience, making it an ideal location for families, professionals, and retirees alike.

Each neighborhood boasts its own distinctive character, with tree-lined streets, beautifully maintained parks, and a strong sense of community. Douglas Hills is known for its spacious homes and friendly atmosphere, while Hurstbourne features elegant properties and upscale amenities. Middletown, with its rich history and quaint downtown area, offers a delightful mix of local shops and restaurants. Anchorage stands out for its picturesque scenery and top-rated schools, providing a serene setting for families.

For those seeking homes with entry side parking, this region has plenty to offer. Many properties in Douglas Hills, Hurstbourne, Middletown, and Anchorage come equipped with convenient side-entry garages, enhancing curb appeal while providing easy access to your home. This thoughtful design not only maximizes space but also allows for additional parking options for guests, making entertaining a breeze.

Living in this area means enjoying a harmonious lifestyle, where the charm of suburban living meets the excitement of nearby Louisville. With a variety of homes that cater to diverse tastes and needs, you’re sure to find the perfect place to call home in Douglas Hills, Hurstbourne, Middletown, or Anchorage. Come explore this welcoming community and discover the ideal balance of comfort, convenience, and charm!

Newest 8 - Douglas Hills / Hurstbourne / Middletown / Anchorage Homes with Entry Side Parking

$934,900
5 Beds ⋅ 4 Baths ⋅ 1724440 MLS
Nestled on 5 breathtaking private acres just off desirable Aiken Road, this extraordinary custom home offers the perfect blend of peaceful country living and modern convenience, just minutes from Middletown, Crestwood, the Gene Snyder, parks, family activities, and the new Publix and all the Old Henry Road exit amenities. Impeccably maintained and thoughtfully engineered, this one-of-a-kind property showcases exceptional craftsmanship, countless upgrades, and features rarely found in today's market. Originally built by a fire chief, safety and preparedness were at the forefront of the home's design. The residence incorporates multiple easily accessible exit routes on every level and is equipped with a heat-activated fire sprinkler system throughout the home, screened porch, and garage. This premium safety feature not only provides incredible peace of mind but also reduces homeowner's insurance costs by approximately 30% annually. A manual electrical transfer switch allows a portable generator (not supplied) to power key areas of the home during outages, while a 4,000-gallon cistern supplies exterior water and can be set to capture rainwater or automatically fill with city water for irrigation. Inside, you'll immediately appreciate the grand foyer, soaring ceilings, and stunning floor-to-ceiling creek stone fireplace anchoring the spacious living room. Rich hardwood flooring flows throughout the main living areas, complemented by custom cabinetry, a kitchen with granite countertops, stainless steel appliances, updated lighting, and beautiful solid wood interior doors. A central vacuum system adds everyday convenience. The luxurious first-floor primary suite serves as a private retreat, featuring heated tile floors, a beautifully renovated spa-inspired bath with a large walk-in shower, soaking tub, double vanity, and oversized walk-in closets. Every bathroom and the laundry room have been professionally remodeled with quality finishes. The finished lower level was designed for entertaining and everyday living, complete with custom cabinetry, a wet bar, recreation area, entertainment space, office or guest bedroom, abundant custom storage, luxury vinyl plank flooring, and sound-reduction insulation between floors for enhanced comfort. Additional highlights include a spacious laundry room with utility sink, oversized 2½-car garage with direct stair access to the lower level, generous storage throughout the home, and a screened porch overlooking the incredibly private backyard. Outside, the property is equally impressive. Extensive professional landscaping surrounds the home, while a large open yard transitions into a peaceful wooded area perfect for children to explore, outdoor recreation, or simply enjoying nature. A shallow creek borders the northern property line, attracting abundant wildlife and creating a truly serene setting. The impressive 30' x 40' pole barn/workshop offers endless possibilities for hobbies, equipment storage, indoor sports, or recreational vehicles. Featuring an insulated roofline and 220-volt electrical service, it's ready for nearly any project. A professionally engineered asphalt driveway, built to accommodate frequent heavy truck traffic, includes multiple underground conduits for future water or electrical expansion, just another example of the incredible foresight invested in this property. Additional features include a newer roof, spray foam insulated roofline for outstanding energy efficiency, a low-maintenance aeration septic system, upgraded mechanical systems, and an exterior designed for years of worry-free ownership. Properties offering this level of privacy, craftsmanship, engineering, and thoughtful design are exceptionally rare. If you've been searching for a home where quality construction, modern convenience, safety, and peaceful acreage come together in one remarkable package, this is the one you've been waiting for.

16812 Aiken Rd, Louisville
$650,000
4 Beds ⋅ 4 Baths ⋅ 1724417 MLS
Opportunities in Sterling Springs Estates are rare. 609 Berwyn Dr, lovingly maintained for 26yrs is now available...so buyers "Start. Your. Engines!" Located on a large corner lot just past the inviting subdivision entry, this 4 bedroom, 3.5 bath 2-story is landscaped with a lush assembly of flowering bushes, trees, and perennials. Pull in the extra-wide driveway to your side-entry 3-car garage...take the front lawn walkway along thoughtfully landscaped beds to your covered front porch that easily accommodates outdoor furnishings. Enter the front door to a welcoming foyer with coat closet and powder room. The foyer opens to a large great room with soaring ceilings, elaborate built-ins, fireplace, graceful trim, built-ins, loads of natural light from windows, and french doors that lead to the back deck. The kitchen and breakfast room are host to loads of cabinets and a work island with ceiling potholder. The laundry room just off the kitchen leads to the super spacious 3-car garage. Also off the kitchen and the great room is a dedicated formal dining room that looks out to the Eden-like backyard. The spacious deck is accessed from both the great room and the 1st floor primary bedroom suite. The primary suite bath has dual vanities, a soaking tub, separate shower, and water closet. The bedroom has 2 large closets and loads of space for a sitting area by the oversized front window. Upstairs are 3 bedrooms and a full bath separated by a catwalk overlooking the greatroom. The Jack n Jill bath opens to the hallway also, and there is loads of upstairs closet space as well as a darling study nook in one of the bedrooms. The finished lower level offers a large family room with plenty of space for the game table, an exercise room, a full bath, and an additional finished space great for a home office or housing an additional bed! 4000+ square feet of space to roam, and an additional 460sqft for storage in the basement! Add to this the beautifully landscaped corner lot, the mature trees, the water features and stonework at the subdivision entrance, the wide streets and sidewalks...this home is fantastic and a pleasure to show!

609 Berwyn Dr, Louisville
$405,000
3 Beds ⋅ 3 Baths ⋅ 1724212 MLS
Fall in love with this immaculate, move-in-ready home on a prime corner lot in Polo Fields! Step inside to fresh, brand-new flooring across the entire main level and a striking vaulted great room illuminated by a stunning palladium window. The spacious kitchen features premium stainless steel appliances, endless counter space, and a perfect view of your private, fully fenced backyard oasis—boasting a gazebo and a custom stamped concrete patio ideal for outdoor entertaining. A formal dining room, a flexible home office, and a half bath round out the first floor. Upstairs, a beautiful open-to-below landing connects a convenient laundry room, two bedrooms with a shared Jack-and-Jill bath, and a luxurious primary suite featuring a double vanity and an enormous walk-in closet. An attached side-entry 2-car garage finishes this spectacular property. This gem will not last—call to book your viewing today!

17449 Curry Branch Rd, Louisville
$1,395,000
4 Beds ⋅ 4 Baths ⋅ 1724207 MLS
Offered for the first time by its original owners, this distinctive residence is situated on approximately one-half acre in the Oxmoor Woods Estate Section of Hurstbourne. The home offers 4,000 + square feet of finished living space, excluding the unfinished basement, with four bedrooms, three full bathrooms, and one half bathroom.. Exceptional craftsmanship is evident throughout, including three-quarter-inch solid hardwood flooring with herringbone detailing, solid custom wood doors, marble flooring, extensive crown molding, chair rails, wood paneling, and custom trim. The main level includes formal living and dining rooms, a private study with a large adjacent alcove, a spacious family room, kitchen and breakfast room, butler's pantry, laundry room, and a light-filled sunroom with floor-to-ceiling windows. The living room features a gas fireplace, and the family room includes a wood-burning fireplace. The kitchen has beautiful custom cabinetry, granite countertops and upgraded finishes, and the sunroom has black-and-white marble flooring. Outdoor features include mature trees, landscaped front and rear yards, a separately metered irrigation system, and a recently refurbished deck. Recent improvements include replacement air-conditioning systems and coils, two gas water heaters, two new garage doors, exterior painting, substantial roof replacement, new carpeting in three bedrooms, and an additional basement sump pump and drain. The home offers convenient access to Hurstbourne Lane, Shelbyville Road, Interstate 64, and the Watterson Expressway, as well as nearby shopping, dining, schools, and Hurstbourne Country Club.

1316 Leighton Cir, Louisville
$2,695,000
6 Beds ⋅ 7 Baths ⋅ 1723954 MLS
Set within the exclusive Enclave of Lake Forest, this extraordinary estate is positioned on 1.4 private acres surrounded by protected woodlands and thoughtfully curated landscaping. Encompassing more than 8,000 square feet, the residence reflects a refined balance of timeless architecture, advanced technology, and meticulously crafted interiors designed for both grand-scale entertaining and everyday living. A circular drive and brick knee wall introduce the property, leading to stately iron entry doors that open into a dramatic foyer defined by barrel-vaulted ceilings, intricate millwork, and custom finishes. Throughout the home, rich hardwood and Appalachian maple flooring, detailed ceiling treatments, arched openings, and bespoke cabinetry create a layered sense of sophistication. The first-floor primary suite offers a private retreat with vaulted ceilings, custom silver maple cabinetry and marble finshes, a walk-in rain shower with water massage, and expansive dual dressing closets. Formal living spaces include a magazine-featured dining room, a richly paneled office with custom built-ins, and an inviting great room anchored by a stone fireplace and coffered ceilings. Designed as the heart of the home, the kitchen is exceptionally appointed with premium appliances, granite surfaces, custom maple and cherry cabinetry, a warming drawer, and a substantial stone-clad island overlooking the hearth room and breakfast area. Vaulted wood-beamed ceilings and a fireplace create warmth and intimacy within the adjoining gathering spaces. French doors throughout the main level open to expansive covered patios framed by white columns, seamlessly extending the living experience outdoors. Multiple fireplaces and generous entertaining areas create an ideal setting while capturing serene woodland views. The upper level offers four spacious bedroom suites, each with walk-in closets and direct bath access, in addition to a multimedia lounge overlooking the foyer. The walkout lower level was designed for entertaining on every scale, featuring a full wine bar, gaming and billiards areas, fitness room, speakeasy style bourbon room with custom bourbon stave wall, guest suite, sitting room with dual sided fireplace, and a dedicated home theater complete with tiered seating, star-lit ceiling panels, and a 120-inch projection screen. Additional highlights include whole-home Crestron audio and video distribution, integrated security and camera systems, invisible speakers within select formal spaces, an oversized attached garage, a secondary two-car garage connected by a breezeway, and unfinished guest quarters offering future expansion opportunities. A rare offering within one of Louisville's most sought-after communities, this residence presents an exceptional combination of privacy, craftsmanship, and modern luxury

3021 Long Creek Way, Louisville
$635,000
4 Beds ⋅ 3 Baths ⋅ 1723902 MLS
Welcome to 18701 Foxbough Glen Place, featuring one of the best backyards you will find under $700K! The outdoor space is truly exceptional, highlighted by a heated saltwater pool with a spillover spa, professionally designed landscaping and landscape lighting, and a covered patio with a beautiful tongue-and-groove vaulted ceiling. The backyard is even prepped for a future outdoor kitchen with gas, electric, and water already roughed in. Located in the desirable Notting Hill neighborhood just off Shelbyville Road, this home offers four bedrooms and three full bathrooms with the primary suite and two additional bedrooms on the second level. The main level includes an ADA accessible suite with a bedroom and full bathroom with an accessible walk-in shower, offering flexibility for guests or multigenerational living. The open living and kitchen area is filled with natural light and beautiful views of the private backyard oasis. Additional upgrades include luxury vinyl plank flooring throughout the living areas and bedrooms, plantation shutters throughout the home, upgraded appliances, an updated 80-gallon water heater, a hardwired security system with exterior cameras, irrigation, and a premium insulated garage door with a quiet belt-drive opener. Built in 2012 and situated on nearly four tenths of an acre, this beautifully upgraded home, delivers exceptional indoor living and a backyard designed to be enjoyed all year long! Homes offering this combination of space, upgrades, location, and versatility are difficult to find at this price point, making this a rare opportunity in Notting Hill.

18701 Foxbough Glen Pl, Louisville
$695,000
5 Beds ⋅ 3 Baths ⋅ 1723747 MLS
Sterling Springs Estates! Homearama showcase home, beautiful all-brick ranch designed and built with upgraded features throughout. An open floor plan with a 1st floor Primary bedroom & laundry & garage with circular drive. A spectacular great room with 14' soaring ceiling heights, Dbl trey ceiling, cam lights, entertainment center and gas fireplace with mantle. Full finished walkout lower — including 2 bedrooms, a full bathroom, full eat-in kitchen, 23' game room and family room with fireplace and a 21.9 x 16.9 garage, perfect for today's lifestyle living . Three full bathrooms total, including an en-suite Lux primary bath. Recent updates include a new roof, new gutters with guards, sealed driveway, updated primary bathroom and a freshly painted — truly move-in ready. Side-entry, first-floor attached garage another a 3rd garage in the lower level adds everyday convenience. Located on one of the neighborhood's most desirable. A beautiful subdivision, landscaped water way median and signature entrance. The properties in the neighborhood of only 92 homes are rare and enjoy a very well maintained community. Quick easy access to any place you want to go to. Schedule personal preview it ASAP !

10316 Carriage House Ct, Louisville
$679,000
6 Beds ⋅ 3 Baths ⋅ 1723617 MLS
Welcome home to 17120 Mallet Hill Dr! Located in the desirable Polo Fields community, this beautifully updated walk-out ranch offers an open, inviting layout with stylish finishes and thoughtful updates throughout. The light-filled great room features soaring ceilings, a stunning fireplace, and custom built-ins, creating the perfect gathering space. The updated kitchen features white cabinetry, stone countertops, stainless steel appliances, bar seating, and an adjoining dining area. The spacious primary bedroom is a relaxing retreat, featuring a large ensuite bathroom with a double vanity, soaking tub, walk-in shower, and generous walk-in closet. Two additional bedrooms, a full bath, a conveniently located laundry room, and an attached two-car garage complete the main level. The finished walk-out basement provides exceptional flexibility with a large family room, game area, three additional bedrooms, a full bath, and abundant storage. Step outside to enjoy the brand-new deck overlooking the fully fenced backyard, or relax on the lower-level patio. Additional updates include a brand-new HVAC and water heater, a two-year-old roof, fresh paint throughout, and a newly paved driveway, offering peace of mind for years to come. Combining modern updates, generous living space, and a sought-after location, this home is ready to welcome its next owners.

17120 Mallet Hill Dr, Louisville
$675,000
4 Beds ⋅ 3 Baths ⋅ 1723354 MLS
Tucked away on a quiet cul-de-sac in one of the area's most desirable neighborhoods, this beautifully updated 4,800 finished square foot home offers the perfect blend of comfort, functionality, and convenience. Featuring four bedrooms and three full bathrooms, the home has been thoughtfully enhanced with fresh paint throughout the main level, updated lighting fixtures, and custom garage shelving designed to maximize storage and organization. Designed for both everyday living and entertaining, the home features inviting indoor and outdoor gathering spaces. A covered back porch creates a true extension of the home, complete with built-in speakers and a television mounted on a hydraulic hinge, making it easy to enjoy game days, movie nights, or relaxing evenings outdoors in comfort. The heart of the home extends beyond the main living spaces into a fully finished lower level, creating an exceptional environment for entertaining, relaxing, and everyday living. The basement features a full kitchen, dedicated wellness bar, spacious billiards room, a 2nd laundry and storage area, and flexible gathering spaces that make hosting family and friends effortless. Perfect for multi-generational living as well! Outside, enjoy professionally maintained, low-maintenance landscaping that allows more time to enjoy the things that matter most. The setting is equally appealing, with friendly neighbors, and minimal traffic thanks to the home's peaceful cul-de-sac location. Conveniently situated just minutes from Publix and I-265, this home provides easy access to shopping, dining, and commuting while maintaining the privacy and tranquility of a neighborhood retreat. This is more than a house. It's a place designed for gathering, entertaining, and creating lasting memories.

507 Standwick Way, Louisville
$830,000
5 Beds ⋅ 4 Baths ⋅ 1723268 MLS
Welcome Home to timeless sophistication in the prestigious Owl Creek Estates neighborhood. Situated on a coveted corner lot, this beautifully maintained traditional home offers an elevated blend of classic architecture and gracious living spaces, all wrapped in pristine, move-in-ready condition. A dramatic two-story foyer sets the tone upon entry, framed by soaring ceilings and an abundance of natural light. The great room anchors the main level with a striking brick fireplace, custom built-ins, and a wet bar — an ideal setting for both relaxed evenings and elegant entertaining. The chef's kitchen is equally impressive, featuring granite countertops, stainless steel appliances, and a gas cooktop, all flowing effortlessly into a sunlit breakfast area, formal dining room, and living room beyond. The main-level primary suite offers a private retreat with its own en suite bath, complemented by two additional first-floor bedrooms, a full bathroom, a powder room for guests, and the convenience of first-floor laundry. Upstairs, two more generously sized bedrooms share a full bath, with unfinished space offering excellent additional storage. The unfinished walkout basement presents a blank canvas, ready for a future recreation room, home gym, or additional living space, tailored entirely to your vision. Outside, a spacious deck overlooks mature trees and lush landscaping, offering a peaceful backdrop for outdoor enjoyment. Timeless character, thoughtful updates, and an unbeatable Owl Creek Estates address, this is a home built to last.

718 Talon Pl, Louisville
$625,000
4 Beds ⋅ 3 Baths ⋅ 1723046 MLS
Perfectly positioned in the serene Midland Meadows community, this sprawling ranch offers the ideal combination of effortless one-floor living and incredible multi-generational flexibility. Spanning an impressive 3,646 above-grade finished square feet, the residence lives significantly larger than its traditional ranch profile suggests, offering a sophisticated floor plan designed for both quiet daily life and large-scale entertaining. The heart of the home is centered on the main level, where the primary living quarters provide the convenience and accessibility of true ranch architecture. Unlike many homes in the area, this property features a massive upper-level recreational space accessed by a permanent staircase. This expansive bonus room serves as a private getaway, recreational oom, or executive home office, kept perfectly comfortable year-round by its own high-efficiency independent mini-split HVAC system. The sheer scale of this home is truly realized in the vast 2,591-square-foot unfinished basement. A rare find for the neighborhood, this lower level is already equipped with a functional commode and utility sink on a dedicated tiled footprint. Because the essential plumbing is already integrated into the foundation, the path to a fully finished lower level is exceptionally clear—offering the potential for over 6,200 total square feet of finished living space. The lifestyle at 305 Gablewood Circle extends beyond the front door. Located just 25 minutes from the Louisville city center, you are surrounded by the lush landscapes of the Midland Meadows golf course and mere minutes from the world-class greens of Valhalla. Whether enjoying the nearby upscale dining and shopping in Middletown or retreating to your quiet corner of the East End, this home delivers a premier Louisville experience with room to grow.

305 Gablewood Cir, Louisville
$475,000
4 Beds ⋅ 3 Baths ⋅ 1723042 MLS
First time on the market since 1978! This immaculate 2 story, traditional home, has been loved for 47 years by the same family. Located in the highly sought after neighborhood of Douglass Hills, this 4 bedroom 2.5 bath home is ready for their next chapter of owners. From the moment you pull up to this charming home, you'll notice the meticulously manicured landscaping and beautifully redone driveway. Once you step inside you'll notice the charm of the traditional home, with a quaint back porch to relax on with friends. This one won't last long!

705 Bell Rock Pl, Louisville
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